CEO retired. How do you politely say "no" without burning a bridge?

Posted by oaomcg@reddit | sysadmin | View on Reddit | 2436 comments

The president/CEO of my company retired about 2 months ago. He's called me at least once a week since for help with his iPad, computer, personal email, etc. and now I feel like I might be personal tech support for life. This guy founded the company I work for. His name is literally on the building. I feel like I owe the guy a lot. He's always been extremely appreciative of my work which I value more than almost anything else because it hasn't always been the case in my career. The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures). He's friends with all the other execs (some of whom I have done some side work for) and I will be seeing him at company social events for as long as I'm here. Do I just bite the bullet, and accept that I'll have to help him with his shit occasionally? Or is there a point to set some boundaries? If so, how do I do so without offending him or burning any other bridges.

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2436 Comments

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zipcad@reddit

If he helped you out, you help him out. Since it sounds like he’s been really good to you, be good to him.

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Poulito@reddit

Totally agree. Sounds like he’s scratched your back for 5 years. What’s it cost you to scratch his a bit? Aside from that, if his name is on it, chances are that he’s still invested in the company as a shareholder or maybe even on the board still.

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No_Investigator3369@reddit

I agree with this. There's some circles that are hard to break into. This is one of those.

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Tutunkommon@reddit

Overlooked by most. You have direct, first-name, "hey, can you do me a favor" access to a circle of proven, successful executives. Never underestimate the power of friendship and networking. Need a reference for a side job or career move? Done. Launching your own business and want some help that isn't either an idiot or full of ulterior motives? All for the cost of helping reset a wifi password or fix an email login? We should all be that lucky.

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uramnich@reddit

This comment needs to be further up. Most CEOs end up on boards post retirement, what if one of those companies needs an executive and he says “oh hey u/oaomcg would be GREAT”

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ColdStockSweat@reddit

[u/oaomcg](https://www.reddit.com/user/oaomcg/) would suck. The fact that this guy even asked this question shows me he's not executive material. A good executive lifts, as he was lifted. This guy forgot awfully fast, where his bread (and butter) came from.

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ColdStockSweat@reddit

[u/oaomcg](https://www.reddit.com/user/oaomcg/) would suck.

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Decent-Park-6681@reddit

The inner circle of the CEO/other top execs are the ones that become the future CEOs and top execs. Do not blow this chance up, even if you don't want to eventually move up that high. You'll be able to essentially dictate the rest of your career.

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DanielTrebuchet@reddit

I've been an entrepreneur for two decades. There is no currency more valuable than social currency, or the power of networking. If you offered me a fantastic network connection or $100k, I'd take the connection every day of the week. "Teach a man to fish" vs "give a man a fish" type of mentality. I understand the frustration of doing ongoing mundane work like this, but the value in maintaining that relationship is worth more than your time will ever be. If nothing else, look at all those bonuses he signed off, put that dollar amount into terms of working hours, and justify the help by saying to yourself than those bonuses were pre-paid tech visits. If he signed off on $50k worth of bonuses and he asks for your help 15 times, just view it as "I'm making over $3k for this tech visit." Over time, someone like that is likely to repay you for your time in the form of a check slipped into a Christmas card. And even if that doesn't happen, again, the value of a good networking relationship like that is truly priceless.

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mikeyfireman@reddit

Also, CEO/Business starters don’t ever retire. So OP will be on the ground floor of whatever he does next.

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mrman08@reddit

Never underestimate *who* they know too. Networking and maintaining relationships is crucial to a successful career even if that means providing free tech support every so often.

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zootered@reddit

This is the type of thing that can honestly change your life. It sounds like this retired CEO *depends* on his help in one way or another, and also that he’s the type of guy to recommend you when their buddy is in dire need of “a guy”. It makes us sound like poor shmucks but being “the guy” that a successful executive recommends to his peer group is game changing. Especially if you can shmooze a bit too.

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Situational_Hagun@reddit

This is what I hate about business. He didn't "scratch OP's back". OP did good work. They got paid appropriately. OP was never done any favors. They showed up, did a good job, got promoted as should be, got pay raises as they should. At no point did the former CEO "help them out". This is the disease deep at the heart of corporate culture. The idea that a company is somehow "doing you a favor" by functioning properly and retaining quality employees.

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renegadecanuck@reddit

Five figure bonuses, without hesitation "large" raise approvals and promotions? I think he absolutely did OP some favours with his career. I'm not sure where you work, but I'm lucky to get a bonus at all, never mind a five figure bonus.

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Situational_Hagun@reddit

How much is that CEO making? Yeah I don't give a crap if they got five finger bonuses. That's paying them what they're worth.

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renegadecanuck@reddit

Does it suck? Yes. Is it a shitty way to run things? Absolutely. If there were a general strike, would I participate? Probably. But the counter point of that is that I'm going to treat a CEO or business owner that treats their staff well better. There are so many executives that will happily exploit their workers, that I'm okay with being nice to the executive that treats their staff well. If being treated well doesn't result in me trying to be a good worker, what's the point in them treating me well? Kindness of their own heart? Not in a capitalist system.

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Any_Dream2835@reddit

Spoken like someone who truly doesn’t understand how things work. Explaining things to these types usually doesn’t solve anything. It’s always the boss’s fault, or “management”. Classic attitude of someone who’s never sat on the other side of the table

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Situational_Hagun@reddit

If an employee does a good job and gets a raise so that they don't leave the company, that is not being a benevolent ruler handing out gold to the peasants. That's called doing what a company is supposed to do. The amount of corporate fellatio going on this thread is sickening.

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Any_Dream2835@reddit

I understand what you’re saying. You don’t have to explain it like I’m five. I used to think that way too. Have you ever been in management? What you’re doing is conflating how the law says things are supposed to work vs how they work. Everyone thinks it’s a meritocracy until one actually gets implemented. A company can just as easily extract all the available energy from you in two years and let you go. Perfectly legal. Amazon openly admits to it. Would you be quoting the same stance? Bezos is worth hundreds of billions because of a some words written to favor him when creating the company. Legally, he’s entitled to those billions. So you agree? You can’t have it both ways. If you’re a stickler for legality, you’re also a supporter of Bezos. Or you can acknowledge that social dynamics exist and some companies help out employees (even if they’re not just handing them free money) while others exploit even if they’re paying the posted wage.

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Any_Dream2835@reddit

I am also a manager of multiple teams. I hire and fire often (more so when I take in a struggling team). I get all kinds of responses from promotions, but the most common is “thanks for making this happen” because of the months-long process it takes to happen. Usually the people are confident, not like a promo is a lottery ticket they didn’t earn, but they’re also aware that others met the bar as well. They may have been one step ahead, but not two. The gratefulness comes from the recognition that it’s often difficult to get a manager to see all the work you do and agree it’s as important as you think it is. If someone has far outstripped everyone else on the team, then yea, no gratitude, just acknowledgement. We both knew what was going to happen. This is of course the best situation to be in for both manager and promo candidate.

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Situational_Hagun@reddit

I am in management. If anyone told me that they felt like a promotion was me doing them a bennie I'd want to vomit.

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Hangryfrodo@reddit

Networking

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SeemedReasonableThen@reddit

> chances are that he’s still invested in the company as a shareholder or maybe even on the board still. Yep, OP might consider having the retired guy bring in his iPad or whatever to work >He's friends with all the other execs "Hey, why don't you swing by the office at around 11 and I can look at that for you. Then we can grab lunch after. If you want, we can also invite [a few other execs] or anyone else you want and catch up on things" Great way to rub shoulders with the other execs

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theFIREMindset@reddit

This is it. Do it on company time. Let the company tell you when you can't. Keep a great friend.

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Tax_Evasion_Savant@reddit

> What’s it cost you to scratch his a bit? It would cost me self respect personally, I don't feel like a rich retired CEO needs or deserves free tech support. Also, a CEO understands better than anyone that he is asking for and receiving free labor. The only thing OP gets out of is not having his reputation ruined, so its the same old power dynamic as when this guy was still CEO. This interaction is not as innocent as it seems, in my opinion.

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Vesper-Martinis@reddit

I appreciate a good boss, but don’t forget that boss makes money from your work. You’ve already done a lot of scratching for him in 5 years.

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damscomp@reddit

Maybe I’m an asshole, but I completely disagree with this notion. He didn’t “scratch his back” for 5 years. He paid OP for his work. He wasn’t paying OP out of the kindness of his heart. Now, can/should OP help someone out occasionally because it’s the nice thing to do? Sure, but that’s up to OP. But OP doesn’t owe this former CEO anything.

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SiliconAutomaton@reddit

“It’s a big club and you ain’t in it” but OP has a foot in the door here. I’ve never regretted staying on good terms with anybody but I have regretted burning bridges.

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renegadecanuck@reddit

If OP got cost of living raises, I'd agree with you. But it sounds like the old CEO went out of their way to give OP raises above and beyond industry standard, as well as some very nice sounding bonuses. That goes a bit beyond just paying the employee for their worth.

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YumYumSweet@reddit

It sounds like he was a good boss. Approved raises, promotions, bonuses, and gave good feedback. Not everyone gets a boss like this. I would try to pay him back for that, especially if he is still influential in the business/industry.

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damscomp@reddit

He was “paid” by the work OP did. I’m going to assume OP isn’t working as a non-profit.

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The_Mad_Titan_Thanos@reddit

If he wants to keep paying him on the side sure but who the fuck wants to give away free labour to some retired rich dude because he gave you a job once and paid you what you were worth to do said job. No chance I’d keep doing him solids unless we were buddies.

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independent__rabbit@reddit

This CEO is never fully retiring. He may have stepped back from the day to day operations, but he will always be in the loop and have a ton of pull at the company. Exactly the type of person you want to have owing you a favor or two.

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Any-Virus7755@reddit

The guy that founded my company is like this. No longer CEO, but still on the board, still has company email, probably a computer, etc. and when he needs something we all know to roll out the red carpet because complaints will get to the c-suite if he has a bad experience.

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Zwarbyt@reddit

How is this even a question? Multiple raises and you can’t take 10 minutes to help him setup an iPad, just do it on company time and be decent

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Klutzy_Scheme_9871@reddit

It’s sad that it has to even be a question, really.

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jetblakc@reddit

I agree. This is such a no-brainer to me but I'm sure op is at least a decade younger than me. And my cultural background emphasizes helping elders even if you're getting nothing in return. It's so reflexive for me that I don't even think about it until someone says something.

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InternationalMany6@reddit

But at the same time, employees are constantly told to set boundaries and that their employers are not their friends. I think this is a pretty clear exception though!

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jetblakc@reddit

he's not his employer. And people "constantly" say lots of shit. Grown ups use their own judgement and values.

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WellHung67@reddit

Could be like “hmm am I being taken advantage of?” And just not knowing

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boddidle@reddit

Tbh, I know we don't want to flame people for asking questions and there's a need to establish boundaries but this post somewhat calls their character into question

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TuunDx@reddit

Not necessarily sad but certainly interesting. This person has to be like super introverted and very individualistic American...

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MIKE___JORDAN23@reddit

I am 100% in favor of work boundaries and the idea that they pay you to work between 9-5 and any time outside of that they have zero right to your time. But the people screaming “YOU DONT OWE HIM SHIT” are so obnoxious

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FruitOrchards@reddit

And people wonder why some bosses act like "assholes"

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DeputyDomeshot@reddit

The question pissed me off a little ngl. You’re the whiz kid in the eyes of this ceo boomer who’s been nothing but good too you. Just fucking help the dude with his fucking iPad.

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Caterpillar89@reddit

I was going to comment the exact same thing. This is a no brainer.

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Pandamonium98@reddit

Did OP say it was just 10 mins somewhere? If that’s the case, I 100% agree. If it’s hours long favors though (migrating everything over to a new PC, etc…) then I think that could change the situation a bit

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calm_hero_9804@reddit

This. Is not about the past anymore. You’re gaining a valuable mentor and a potential springboard into senior roles for about 10 minutes a week? I’d say go all in with the help and try educate him to self resolve these issues. He’ll appreciate the knowledge transfer and your protectiveness in helping him learn tech.

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Whatever5588@reddit

Exactly, OP is an ungrateful low level person who can’t think beyond a task.

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rubyhardflames@reddit

Hyperindividualism and a transactional view on relationships I suppose. I see those going hand-in-hand with a lot of newer perspectives nowadays.

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Ok_Mechanic8704@reddit

Here’s a legitimate question for OP: Are you stupid?

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redtiber@reddit

seriously, the tasks op mentioned are so trivial. when i read the headline i was thinking it was going to be something crazy like his old ceo wants him to setup a brand new company backend for free, or calling him at 3am and being demanding.

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40ozCurls@reddit

Raises are not supposed to be personal favors. Helping set up an iPad off the clock is.

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StinkyKyle@reddit

Im really confused about this mentality. You get a raise for working hard, its not a favor by your boss, right? You dont owe him for getting raises, its something they earned with hard work

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Handplanes@reddit

I’d take an opportunity to acknowledge how much he’s done for you. “Hey I can’t afford to do free tech support for all my friends, but I can absolutely help you out when you need it. You’ve done so much for me over the years, I appreciate our time working together & you really helped set me up for success”. Then fix his iPad, drink a beer together & reminisce for a bit.

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Ok-Strength-5297@reddit

multiple raises is expected? i'm hoping you don't still earn the same as a couple years ago

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MadKian@reddit

AND 5 figure bonuses. I’d even say that CEO earned the help.

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ethnicman1971@reddit

hell, even if it is on your own time help the dude out. If it is something that is too large for you to help him with, explain why it is above your ability and offer to help him find someone who can help him.

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apb2718@reddit

I want to see OP commit to this response

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AlexCail@reddit

Without question the morally correct answer. I’d feel bad not helping tbh.

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nick_storm@reddit

It doesn't hurt to have friends in high places.

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occasional_cynic@reddit

Even if he is no longer in a decision makers role, I just always try to be good to people who are good to me. OTOH I had a manager years back who regularly put me down, ignored my achievements, and refused to promote me. He later contacted me asking for a reference. I never responded.

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Culero@reddit

> OTOH I had a manager years back who regularly put me down, ignored my achievements, and refused to promote me. He later contacted me asking for a reference. I never responded. Same here. I'm out here ever so slightly envious of OP's position. I swear all my last boss ever did was tear me down, despite me being the top performer and well liked by the clients (or because of?).

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occasional_cynic@reddit

In my case he simply did not respect our work. He had a project management background, and looking back that was the type of work he valued/concentrated on. Heck, we had four PM's out of a department of thirteen by the time he left.

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jackmusick@reddit

It’s kind of implied, but these people have connections even after they retire. It’s good to network with good people. They’ll help you, you’ll help them.

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willyam3b@reddit

Me too. I genuinely miss some of my old bosses and hope they are really well, and would jump at any chance if they needed me. Those mentors and cheerleaders for you come few and far between, and they are so missed. Man, I wish I'd lived my life making the right moves to see five-figure bonuses lol. Respect. There are also two that I regularly deny contact attempts with on social media. True bullies both of them. One of them had the hots for a female employee, and told her he would fire me and put her in my seat so she would stay and not take an internal offer to move. She was a good enough coworker to warn me. The other offered to move me out of my cube (in front of me) and put the female coworker he had a thing for into that chair as well next to her friend. What a weird pattern.

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MudderFuffer@reddit

I totally agree with this. Cause I got friends in low places

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xamboozi@reddit

Yea he likely has connections. Be good to him and schmooze with him for more opps. He might have other friends that are interested in side work. Maybe he could help you build something of your own. As a general life lesson, surround yourself with people that make things happen and things will happen for you.

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Scrimps@reddit

I have been in Comp Engineering for 20 years. OP literally has the best connection he could ever hope for. Suck it up and help him like he helped you. This is not the same as a friend who just asks for help but provides none, or a friend of a friend. 99 percent of people who work in tech will never get on the inside circle. I was involved with Bitcoin and Crypto in general from the beginning. I worked for ATI when AMD bought them in 05, I quit and used my pay package to buy $21,000 in Nvidia stock (half my package). Which I have today. The only reason I was ever even approached for an executive level job with my current firm is because I had more money than most of the people working there, and I was always a good person to be around. Unless your company is having major problems, all the "inside circle" looks for is people they can get along with and trust.

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IamtheBiscuit@reddit

Don't you have an intern or assistant to run interference? He gets more attentive help, your intern gets face time with the founder and whatever perks come with it, and you don't look like a dick. Or he is lonely in retirement and genuinely enjoyed seeing you every day

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vstrong50@reddit

Exactly this. Normally I would probably say to have a polite conversation with them, ending the tech support. But this man was extraordinarily generous it sounds, and just a generally good and supportive person to OP. I'd continue to help with whatever the CEO needed, within reason.

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absbabs1@reddit

It also sounds like the ceo misses him

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ProcedureHopeful7538@reddit

Agreed. I’d like to add if he’s a cool guy which it sounds like he is. Needle him a little bit if he keeps calling for the same/similar problems. Maybe he’ll think about the problem before picking up the phone and calling you. I’ve done my share of tech support for older co-workers and that tactic has helped…sometimes. Be respectful though. Some of these older retired execs are just bored immediately after retirement and this guy could be calling you just cause he’s bored and likes you.

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Mr-Blah@reddit

Strong community ties requires inconvenience. I agree with you, helping him out is the good move at least to stay in good terms etc... One, my wife worked for a C suite and one of their fprmer employees was in a jam in another country and the first call they made was to that exec. Within hours he was out of jail and on a plane home. And that was for a former employee (of several years...) Reset the password and keep his number OP.

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netman67@reddit

I’d also add that he may not be done helping you out. How many of us would like a connection like a CEO, with a network of people in positions to help your growth even further? This is the very definition of growing your professional network.

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snarky_witch@reddit

This! I was an executive assistant to the founder partner. I treated the same after he retired. He would often leave me cash as a thank you. He took such good care of me when he was in charge it was the least I could do for him in retirement. We became friends after he retired. He made me cry as a boss but became my favorite person in retirement. Bastard had the nerve to die on me last year.

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ibanezerscrooge@reddit

Second this. I know it can be annoying to be "The Guy" sometimes, especially when it becomes more personal, but if this guy has been the springboard for your career and success I think you suck it up and be grateful.

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StinkyKyle@reddit

But giving promotions and bonuses isnt helping them out, it was a reward for hard work, right? It feels like everything they mentioned they got through hard work, not a favor by the CEO

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vgullotta@reddit

Yeah I agree, he's just going through a change in his life right now and is going to have to rely on personal email and what not and get used to it. The calls will subside soon enough and OP can feel good about themselves for keeping their end of the good will bargain. Never burn a good bridge, only the ones that are beyond repair.

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MoparRob@reddit

Exactly! If he’s treated you well, you treat him well. This sounds like one of those people who can be a great asset to your career beyond just the current scope. Nothing wrong with saying I can’t help at this immediate moment, but schedule the follow up during that call. Likely this guy has many contacts and could be a great help if you ever decide to make a change.

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stickytack@reddit

THIS IS THE ANSWER.

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PrimaryAverage@reddit

Exactly and while you're fixing stuff for him, teach him along the way. Maybe he'll bother you less and less over time because he knows how to do it himself. Worked with my mom lol.

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trippedonatater@reddit

Plus, having that one rich friend is usually a good thing.

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trdush1994@reddit

I love my rich friend, i get all his hand me downs 😂

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desquished@reddit

Having a rich friend with a kid who is one year older than my kid has saved me thousands of dollars, easy.

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fragilewicked@reddit

Hand me downs = budget‑sysadmin life 🤣

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Redfugitive20@reddit

My one rich friend saved my son and I when leaving an abusive marriage. Always treat others the way you want to be treated. No matter who they are.

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MichaSound@reddit

Plus, he may be officially reaching out for tech support, but maybe what he really wants is to maintain the friendship.

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yournamehere10bucks@reddit

Might be one of the few friends he has that arent either sycophants or people asking for favors.

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Live-Ad-2354@reddit

Honestly just tell them if you have time or not.. and when you can help. I see all these memes about how people get upset when their family ask IT stuff on holidays or whatever. I love helping them have the knowledge they need to survive in todays world. I've helped repair computers for friends of friends etc. just because. If it's not some week-long wiring configuration and home security setup, I got a little free time.. I'm here for it.

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robvas@reddit

You never know he might throw you some cash etc

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gordonv@reddit

Nah. But lets say you get fired. His word and influence will get you a job. This is better than Indeed.com.

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Short-Sound-4190@reddit

Agreed - in a time where so many industries are shedding even their qualified employees and unemployment is up across the board, the FASTEST WAY to find the BEST place for future employment is having relationships with people who have connections and will for both your sake and even their own personal aplumb recommend you to their connections - I've literally watched it happen three times this year in my spouse's company: 100% of their new hires were personal recommendations. If course that's not to say you wouldn't still have to interview and be right for the position but networking and maintaining those relationships can get your foot in even a closed door. My spouse still reaches out/gets reached out to, in order to go out to lunch with their coworkers and mentors who are still in the general field from 10+ years ago - it's a sign you've done something right if you're able to network because trust me someone who does a legitimately bad job, poor work ethic, hard to work with, etc is the kind of person who doesn't get "catching up" calls/emails and only reaches out at most when they lose their job and usually doesn't get helpful if any replies back.

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Unexpected_Muffin@reddit

Yeah this is the reason right here. I’ve gotten more jobs because of the recommendation from people I’ve worked with than cold calling. Getting a recommendation from a CEO that retired (meaning the company is still going strong) would have significant weight. Plus a 5 figure bonus… we used to say “$20 bucks is $20 bucks” when it came to some outlandish things, but for 5 figures I’d tell my wife “Honey we’re about to pay off some bills, but you can’t ask what happened.”

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robvas@reddit

I have definitely been recruited by former CEO's at their new gigs

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ethnicman1971@reddit

the cash that may be thrown may not be in the form of a check or zelle. It more likely be in the form of a good reference for that next job. Having a successful founder/CEO as a reference carries a lot of weight especially if he is known and respected in the field.

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Whereami259@reddit

Or if you ever decide to venture into solo career, its a connection that helps immensely.

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DeifniteProfessional@reddit

I feel like the offer should be there. There's plenty of people I've done tech support for who used to work at my company and they're always buy me a token gift and it's always appreciated. But also it sounds like this dude has just been a really good boss, and whilst that's not required, maybe he helped OP have a sexy new truck, but that's kinda the point of having a job. In return, OP helped this man retire with a comfortable wad of cash in his pension

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Yharnam_Blunderbuss@reddit

OP comes across grateful in his words but ungrateful in his thoughts. "Multiple promotions... mutiple large raises"... how difficult or time consuming can IPad support be FFS.

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MarleysGhost2024@reddit

This^^^

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NewsPeach@reddit

>If he helped you out, you help him out. This! Having a long memory in a world where having a short memory is common will help you go far.

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weaponsgradepotatoes@reddit

And you never know if he’s going to build another company or talk to with someone in a similar line of business who needs OPs help. Obviously, protect your time OP and make sure you aren’t being taken advantage of, but it never hurts to have connections.

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diwhychuck@reddit

This my guy is good to keep in your network. I’m sure he knows more ceos in the business world if they decide to jump ship.

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IntelligentTeam6290@reddit

I'm in the same position as OP and go above and beyond for those that help created this life where i can comfortably provide for my family.

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chewbaccashotlast@reddit

1000%. I read the post and really can’t come up with a legit reason why you shouldn’t help him. People ask for help as friends all the time. You may not consider him a friend but maybe he considers you one!

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jmeador42@reddit

But to what end? This CEO was simply doing a good job as CEO. I don't believe merely doing a good job means he is now magically entitled to another person's free time.

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theprodigalslouch@reddit

Its not about entitlement. It’s about thanking the people who made your life better. Being kind for the sake of showing appreciation.

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my_name_isnt_clever@reddit

My employers thank me with my salary. Once he's retired he's not part of my job any more. I feel like I'm taking crazy pills in this thread, OP owes this man nothing.

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theprodigalslouch@reddit

You’re not crazy. It’s just a difference in views. You see the employee/employer dynamic as nothing more than a professional relationship. There’s nothing wrong with that. That’s a perfectly fine way to handle things. Clean, professional and by the book. Some of us probably have experiences where employers have not been as generous as OPs old boss. So we value that greatly. It’s not just a professional relationship. Not necessarily a friendship but a friendly relationship. And sometimes you just do things for your friends because you like them. For some in this thread it’s about showing appreciation for someone who added a great deal of value to their lives. For others it’s about maintaining a useful connection. The latter see this as networking. There are at least 3 camps in this thread if we want to categorize. I keep in touch with old colleagues because they made my work life better. Not because of some contractual obligation.

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my_name_isnt_clever@reddit

I see it as strictly professional because that's the only option they give us. A decade ago I would have thought this was sweet, I worked for a kind CEO like this. But since then I got fired from that job with no warning, and the dude didn't even recognize me a few months later running into him in town. I was just another business transaction to him. I'm too jaded for this shit now. Corporations chew us up and spit us out for nothing more than improving some numbers this quarter, we owe them *nothing*.

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jmeador42@reddit

I agree with simply being a good friend, but if he's asking for copious amounts of help outside of work hours then it absolutely *is* entitlement.

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SuperMundaneHero@reddit

Because he is still connected and influential, and if you need a favor you can ask for his help. Not everything needs to be about that though: sometimes it’s good to be nice to the guy that helped your career progress just because. It’s nice to be nice, you know?

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nope-its@reddit

Also he was CEO of a company - he’s got connections. This is not a bridge to be burned.

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Apprehensive_Ear7309@reddit

Agreed

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Shazam1269@reddit

I was all set to say, "aw, hell no!", but after reading how well OP was treated by the former CEO I reversed my decision. Once a week is a little excessive, so OP may be justified in giving him a recommendation for support assistance that could reduce the frequency. It sounds like the CEO is a good guy, and would be understanding if OP is too busy from time to time.

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Loong_Road@reddit

Yes this 👆Please help him out and you will be rewarded further

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mrdeadsniper@reddit

I was really worried I was going to see a bunch of scorched earth nonsense in here. This guy is owed several favors, if it gets to a point of interrupting business or the like then yeah maybe mention it. But if its only 2 months since they left the place maybe just bite the bullet a little while longer.

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henrystandinggoat@reddit

They helped the CEO out by exchanging his labor for pay. The CEO benefited greatly from all the people who did this and isn’t owed anything more.

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JohnnyRa1nbow@reddit

Yeah. Just sort the dude out jfc. This is engagement bait surely?

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sparklyfluff@reddit

i’m right here as well

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DazzlingRutabega@reddit

Don't be afraid to set some sort of boundaries however. In your time outside of work, your family should take precedence and he should be willing to understand this.

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PumpkinCarvingisFun@reddit

Definitely. Just be his friend, man. Seems like he was looking out for you.

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Mysterious-Ant6005@reddit

Yes. You should always pay your debts. I am going to add though, sadly, there might still be something in this for you. Like you said he still knows the current execs and everything at the company. Maybe if they go to him for a name for someone to pull up? Oh! Hey! How about the guy that’s been helping me for the past year despite not having to. Not saying it’s a guarantee. But it’s a possibility? Anyway. Good luck. If you have to drive to his place for stuff? Make sure you’re punched in.

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shatterdaymorn@reddit

This... but make an effort to ENJOY helping them. If you insist on viewing it as "payback" or a "debt to be discharged", you'll just grow to resent it. Nip that in the bud and try to create something new with your former CEO. Maybe he just wants a friend and is socially clueless since WORK was his social life.

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Yamr3@reddit

Exactly this. I was the favorite of the IT team I was in at my last job. He'd always call me over the others. He was so nice to me too and what for me into the job when I was there years ago. I will always answer the call from him; because if it wasn't for him, I wouldn't be where I am today. Always return the favor to people who are good, and nice, to you. You don't have to do that to people who are not good, or nice.

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sybrwookie@reddit

I would say, as long as he's calling during business hours, go for it. If it's off-hours when you're not working....you need to not pick up that phone call.

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jetblakc@reddit

I mean I don't pick up any phone call I don't have time for

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Inner-Copy9764@reddit

I also agree with this.

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oswaldcopperpot@reddit

How did he manage to write all that out without a bit of self-realization?

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JamesArget@reddit

Once a week can be a lot. If it's on company time, and the management is good with extending this as a service, great. But if this is cutting to personal time, that's a different story.

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t53deletion@reddit

100% this. If it becomes more than a simple fix, openly talk about a modest fee for your time. Otherwise, this is networking when discussed outside of the IEEE definition.

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dropthehandle@reddit

I’ll second this. Even retired, a person that was in that position can still continue to help you in your career moving forward. A CEO that I had worked for almost 10 years ago still calls for help a few times a year, but he has continued to help me over the years as well by using his connections to get me into new roles. It sounds like he trusts and respects you. No harm keeping that bridge built and adding some reinforcements.

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mr_lab_rat@reddit

This can become tedious. Supporting older people is no joke. I do it but I make sure I get paid a lot for my patience.

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DeerOnARoof@reddit

Once a week for 2 months though? That's way too often

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The-BruteSquad@reddit

I agree. I do this too for the guy who founded the company I work for. He called and asked for a lot of help when he first retired, but it got less and less as time went on. Now I rarely heard from him. Old habits die hard.

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TreborG2@reddit

While I agree with the idea behind all of this, OP needs to start off with simple ground rules. If you're not the manager, make sure you talk it over with your manager. When you go to talk to your manager have a simple plan in place... Ask the CEO to either send the request in email, or to make sure you have a way of getting credit, that you have the ability to create a ticket attached to the CEOs personal email address. Make sure any updates Go into the ticket as well, and when you've finished a task, and can close out the ticket use the same kind of logic that you would at any other ticket, mention to the x CEO that he'll be receiving a email survey, etc so you get the kudos or whatever else documented as well, asking the CEO to fill out the survey.. Anything that requires more time, or materials, then just a phone call or so, again make sure you track this very carefully and make sure management knows you're doing these things. This is time that the company is paying for, during normal business hours, and anything after hours has to be reported as work so the company knows you're still doing something for the retired CEO ... Treating it just like anyone else inside the company helps things stay accountable, trackable, so that if necessary someone in the committee can say hey this is costing us money to support our CEO and remind the x CEO of this... Even if it's in a friendly conversation it's just a reminder that they're still putting resources available to them.

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typo180@reddit

I agree, but also don't be afraid to set some reasonable boundaries. If you're busy, with family, on vacation, etc, you can say that you can't help right away, but will get back to him. You can tell him if the requests are becoming too frequent or too large (often people who need tech help don't have a good sense for how big a request is). "Hey, I'm happy to help you out a little and I'm glad we're keeping in touch, but that's a pretty big ask..." etc.

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Bucolicwoods@reddit

Yeah, seems to be the right answer.

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brontide@reddit

He was a good boss, but now he is retired. I would totally give them a grace period. Once that grace period is up ( 3-6 months ) he needs to make sure that the time spent is properly accounted for with his supervisors. I like to say "I work for my boss, not the customers", so as long as the supervisors continue to be find with the work then why not? I just worry that this becomes an unaccounted for 20% of his time or the defacto home IT support person for the old CEO without it being reflected properly in his scope of work and compensation, especially if it's "on call" work.

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drummerboy-98012@reddit

This, 💯. After all of the pieces of garbage I’ve had to work for over my 30 year career, I would HAPPILY help this guy out without hesitation. Question, though: Is this all during company hours, or are you having to make house-calls and/or help him on the weekends?

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Blue_Line@reddit

Bingo.

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cascajal@reddit

Also, hwile formally retired, seems he owns or partially owns the company you work for, so, seems you still report to him in some way.

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rt58killer10@reddit

This. Personally I love helping people out with tech, seems like a small sacrifice for someone who's been so generous to you

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theolentangy@reddit

I hate to agree with this on some level, but you’re right. This isn’t the usual boss/employee relationship, at least not the way it was presented. Clearly OP actually does feel a real and seemingly justified sense of loyalty to this person, and it’s perfectly OK to choose to help them.

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Previous_File2943@reddit

Yeah, this is good. You have to reciprocate to the people who have been good to you in your life. Especially in this society. Those kind of people are few and far between my friend.

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countsachot@reddit

This guy sounds almost like a friend of sorts. If he's helped you out that much, it's your call, but he seems worthy.

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MisterMarsupial@reddit

For sure. If I was in OP's position and the CEO was a chill person (which is sounds like they are) I'd suggest them shouting lunch sometime. That's what I charge friends and family. It's also a nice reason to catch up for an hour or two.

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Gutter-Snipe@reddit

Exactly. Gives a good opportunity to have conversations outside of work too. Maybe drop a mention that you started growing your bourbon collection or whatever and next time he’ll have a nice bottle for you!

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wow___just_wow@reddit

LOL! Did this very thing and I am now a non-drinker with boxes of bourbon!

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wow___just_wow@reddit

Wow - I get downvoted for having boxes of bourbon. I love Reddit!

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ReMapper@reddit

Also, mentoring.

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ElephantBingo@reddit

Also, bourbon.

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amazing_spyman@reddit

Yup OP should def look into mentoring baboons

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Urban_Heretic@reddit

Unfortunately, not much money in meditating bourbon these days.

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joe_s1171@reddit

i bed to differ, there is a lot of monkey in baboons that can mediate.

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AlternativeNewtDuck@reddit

Why not mediating both?

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joe_s1171@reddit

levitating both money and monkees? are you out of your damn mind!!

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rugbyj@reddit

I'm modulating bonbons as we speak.

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Lucius-Halthier@reddit

Mechanizing some boobs right now archmagos, in a little bit the nipples will fire radioactive lasers!

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joe_s1171@reddit

This is exactly what I was looking for! update me!

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skiwith@reddit

Monkey shoulder is a great whiskey for meditating on mentoring old French Nobility (the Bourbons).

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BatemansChainsaw@reddit

Are we talking about BSD now or is this still people? ;)

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Engine_Sweet@reddit

No murdering baboons! We still haven't gotten over Harambe

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macsmith230@reddit

There’s always monkeys in the bourbon stand.

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chimichan9a@reddit

Instructions unclear, dick stuck in baboon

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LibrarianFlaky951@reddit

You too? Shit.

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osmiumblue66@reddit

I have been accused of being a baboon and always appreciate mentoring.

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katet_of_19@reddit

If he doesn't, I'm going to. OP, please don't do this, I wanna mentor the baboons.

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isaiddgooddaysir@reddit

Or scotch….

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Cautious_Buffalo6563@reddit

![gif](giphy|3o7TKF1fSIs1R19B8k)

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nphare@reddit

Mentoring would be worth more than time or money.

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unbelievablygeneric@reddit

This

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Acrobatic-Factor1941@reddit

Also, he sounds like a good guy to give you a good reference and leads on other jobs, should you ever need one.

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bindermichi@reddit

and getting into a good position with the other Execs

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Sindaan@reddit

This is the very thing I was thinking. OP next time he needs help, see if he would offer some mentoring to help your progression in the company.

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Decent-Park-6681@reddit

Yeah, not for nothing man but you're looking at this all wrong. This is such a small price to pay for the networking alone.

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Gutter-Snipe@reddit

I agree with a lot of these comments as an approach to move up in the career. I was just trying to help get past the “working for free” mindset. Also I like a good bourbon lol

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MikeyRidesABikey@reddit

The guy that owned the company that I used to work for buys brunch for me, my wife and my daughter every month or so, whether I help him out with any IT things or not, and will happily throw a couple of bottles of expensive wine my way when I do help him out.

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Sobriquet-acushla@reddit

It sounds like CEO is an appreciative guy, not an advantage-taker. He may have a big surprise for you.

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jethrothegamer@reddit

Or maybe he figures being helped, post-retirement, is a reward for his positive treatment of the OP as an employee in previous years.

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HonkHonkItsMe@reddit

This.

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Cake-Over@reddit

*You know I recently got into Fabergé Egg collecting*

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Unhappy-Week-8781@reddit

I collect bricks of solid gold…

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Commercial-Co@reddit

Y’all approaching this all wrong. He could become buddies with a C Suite (altho retired) founder that can help him climb the ladder. Using that for a bottle of bourbon just cements that you will be an underling. Use it to become equals and push for a c suite position like cto or a step under cto. Or use it to push for a job elsewhere. C suite founders know other c suite founders. Get into the club

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DrWildIndigo@reddit

Abso-Fycking-lutely! I just said same-same up above... Wasn't an opportunity to change his Life over feeling like a lackey rather than a Baller... Get a Baller mindset... Talk to this man every day‼️

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Commercial-Co@reddit

Yup my business exploded when i got into the club. Now my income is 7 figures annually and it continues to grow

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beer_curmudgeon@reddit

Im with you. Now that he isnt the boss, a genuine friendship may start to blossom.

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CircadianPolemic@reddit

Love this. Great networking opportunity, OP. No reason to burn a bridge; if anything, it’s a testament to your abilities.

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goorlando1@reddit

Love this. Ty

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LoneWolf_890@reddit

This is a smart move!

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Advanced-Skill6308@reddit

CEOs go onto start / found other business’. I’d suggest you lend a hand on his iPad. When he inevitably goes onto start something new - he will remember your generosity and likely support you in some way - a job for you, a family member. Support with your own plans. Innovators & entrepreneurs never stop. Stay friends with them. “Hi, welcome to the Genius Bar, how can I help you” - this is now you. 🍏🤓

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LegitChew@reddit

That's probably the best response. "I'll fix your iPad, but it'll cost you lunch. Taco Tuesday??"

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Soft_Yellow1757@reddit

i refuse to do work for friends and family. they never understand the amount of work i am doing or the value of my time- so there is no amount of discount i can give that makes everyone happy. They also do not understand that as a lawyer i cannot win every case by simply doing more work.

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JulianRSC@reddit

But he is somebody extremely appreciative of he work, not a friend who don't know the effort back that.

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tacocarteleventeen@reddit

Plus the guy likely has serious connections and could keep helping your career

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Tricky_Orange_4526@reddit

this is what i came here to say. if he's got connections, use it as a networking opportunity.

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EanBvasion@reddit

He even mentions in the post he’s still friendly with all the execs. This is a no brainer. This is the kind of relationship that pays you back ten fold, and it seems like he already knows it by listing all things he’s done for him. Sure, it’s possible this becomes more trouble than it’s worth and he may have to reevaluate but going to lunch with this guy once a month is probably the most lucrative thing he could do for his career

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DrWildIndigo@reddit

Exactly 💯 🧠🧠🧠🧠🧠🧠

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plasticbug@reddit

Hell yeh. That sounds like an amazing insurance policy in case OP gets mistreated at work.

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Worldly_Stop_175@reddit

Truly this, and you have to really consider how this person will respond if you refuse to help. One complaint to the new CEO or Head of HR may be enough to cut the bonus in half. There is really no option here except get a new job if you don’t like it.

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Quinctilianus@reddit

Ya, like you above said. I get how helping someone could be tedious, but if you have some sort of friendship and he's helped you a lot I don't see the harm in biting the bullet, as you said. You never know when, if you keep at it, he either gives you something or gives you a few pointers on furthering the career.

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FloMoore@reddit

OP is retired.

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sorbet_babe@reddit

The CEO is retired, not OP

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FloMoore@reddit

Oops! Sorry.

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munistadium@reddit

He could also blacklist him. It's in OPs interest to help and use him as a mentor.

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CodeNCats@reddit

The amount of knowledge you can gain from a person like this

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DragonflyMean1224@reddit

Yup. I agree. Ask for lunch time with him. Networking is literally the best way to get promoted int better paying jobs. He can probably still work his magic. Maybe he might talk you up at future social events.

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EVERYONESTOPSHOUTING@reddit

Yeah this is lovely, just say "why don't we grab lunch and catch up, and then afterwards I can sort your ipad out"

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FunctionOk2835@reddit

Agreed. I get the not working for free bit, even with friends that's not cool all the time. So drop some hints about your beverage of choice, recent hobbies, what have you. He probably is just so used to you helping him out, he doesn't realize he's kinda taking advantage of you, and if he's as good of a guy as you say he is, I'm sure he'll figure something out.

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TwoToesToni@reddit

Agreed, if the guys trusts you enough to come fix his tech issues (even if they are stupid things like ipads) then you should have a good relationship with him. Basically just saying to get lunch or a couple of bottles is good enough as well as avoid any potential issues if someone reports you the IRS for running a from home business (it might sound stupid but ive heard it happen).

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Tlacuache552@reddit

This is the way. And then, if I were OP, I’d talk about my career goals and ask for advice. He’ll prolly offer to directly help

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theantig@reddit

Dude could just be lonely too. This would be a double help. Stopping work could make him bored

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Hyperdyne-120-A2@reddit

100% this!

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neznetwork@reddit

I was gonna say I knew you were Australian because of your use of "shouting", but then I saw your username and found myself a little oblivious for not noticing in through the more... Obvious means

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cavscout43@reddit

Also if they're never available for "friendly" stuff yet keep calling on OP for help when it's their convenience...well that's pretty telling on if there's a relationship or not.

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Invspam@reddit

this is the way to do it. keep growing your network.

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but_good@reddit

LUNCH!

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BicentenialDude@reddit

Exactly and who knows… op might end up as CEO of he works his way up. Founders will always have a large influence in the company and when it’s time for a new CEO, OP’s got a chance. OP, why not message him up once in a while to check if he needs help with anything tech. Don’t wait for him to call you. Invite him for lunch where you can help him with his phone or iPad. Nurture it right and you got a good future in that company.

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1kn0wn0thing@reddit

100%. Just because he’s retired doesn’t mean he’s no longer golfs and hangs out with other CEO’s and executives. If he’s chatting with someone who’s looking for a person to fill a role, having him say “I know a guy that would be perfect” is much better than you applying for the role and saying “I’m perfect for this role.” 🤷‍♂️

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yousirnaime@reddit

“I can help you today - Bring your iPad this restaurant at noon”

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WellHung67@reddit

What’s shouting lunch? Do they both meet up and go “LUNCH” and then fuck off back to where they were? If so I am so intrigued, IT culture is fascinating

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vanquishedfoe@reddit

Just adding to this; if op needs a selfish reason for meeting up with the guy, you can think of it as a mentorship now.

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1Oaktree@reddit

What's a shouting lunch?

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NeemOilFilter@reddit

I’m a big fan of the food/drinks in exchange for a little favor like helping with some IT

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MisterMarsupial@reddit

It's a great divider too! Lot's of people I'lll do blanket sysadmin support in exchange for dinner but there's also a whole ton who get my consulting rate, haha :p

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sir_mrej@reddit

LUNCH!

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glittermacaroni@reddit

You did it!

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manda-rino@reddit

Agree, that’s the best you can do

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countsachot@reddit

Great idea!

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CaptainReginaldLong@reddit

My thoughts exactly. He's not just a boss, he's a friend at this point who's given OP a lot. If it were me, I'd be glad to help. But I also wouldn't fault OP for wanting to set some boundaries.

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AlertOwl3691@reddit

I agree. He sounds like he’s earned some tech support and it sounds like very lightweight support. iPad support can’t be that bad- usually it’s an information issue. Not much can be done otherwise, configs and user info I would guess. I’d tell him that he owes me a beer or lunch and we can catch up. A successful guy probably could teach us a thing or two also and be a great asset when we want to move up or on.

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AveenaLandon@reddit

Being friends or at least friendly with him and staying in contact with him can potentially help you build up your own professional network and land more lucrative job opportunities. I think having to help him with his computer issues is a small price to pay for all that.

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j2thebees@reddit

Yes. And it’s likely the tech support needs will wane over time. Strictly from a career perspective, someone who has retired out of a business not only has contacts, but knowledge that you may benefit from.

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LeiraLaw@reddit

This.. but you do it only until you are at a point where you can delegate to someone trusted beneath you in the chain of command.

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deadzol@reddit

Yeah this guy might be able to continue to pull strings in OPs favor. I’d prolly bite the bullet professionally. If the dude is valuing the relationship as a friendship, then ya just treat him like any other friend.

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gpuyy@reddit

This is the way ^ Don’t burn that bridge as it may lead you to better pastures

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uniform_foxtrot@reddit

Even without any prospects of future returns I'd say it is well worth spending some time a week on that man, all things considered.

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HugsyMalone@reddit

Yeah sounds like CEO really bent over backwards for the guy. It'd be a shame if the favor suddenly wasn't returned. I'm sure he'd be devastated. I know it can feel annoying at times since it feels like he's taking precious time away from OPs job and causing undue stress but sometimes you have to bite your tongue and grin-and-bear it for somebody who went out of their way for you. Go into it knowing it won't always be this way. He just retired 2 months ago and misses his job and the people and the camaraderie. As more time passes he'll likely fade away and will keep in contact less and less. It'll get easier.

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rkthehermit@reddit

And hey if it starts to feel like he's taking advantage later it's not like the bridge will be less flammable then.

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the_lost_carrot@reddit

Plus there is a good chance if the guys name is on the building he may still be a part owner. I’d just treat it as part of the job and provide the support.

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Typical-Banana3343@reddit

Exactly

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1917he@reddit

Where do you get that shit from? All he did was act like a decent boss according to OP. They didn't share meals or hangout. OP just thinks this guy is some god because he paid on time.

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erbmike@reddit

Yeah, that sounds like a guy who has been very generous. I’d bite the bullet, of sorts. I’m sure there’s a good way to go about this, but I don’t know how. Maybe have a visit where you can set up a time, like once a week, where you can answer questions and troubleshoot? Since the founder is buds with his successors, bring it up with them and see if it can wrap into a small part of a workday? I don’t know. I’m sure there’s a happy medium somewhere.

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S-Lover98@reddit

You help your friends. Period. >I owe the guy a lot Sounds like a friend to me. I say help him.

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tomtomclubthumb@reddit

It also sounds like this might just be a pretext to stay in touch.

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MuttleyDastardly@reddit

I’d call him to go out for a beer or to my place to watch a game and see how he reacts. That’s how I’d figure it out

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Intelligent-Kale-877@reddit

Like others have mentioned, this guy is in a position to help you or your children (as a mentor). You should stay grow this friendship.

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DrWildIndigo@reddit

Understand that that kind of power persists whether he is in an Office building or at home or the Golf ⛳️ course... You are not just cutting your nose off, but burning your whole damn head off because of a few favors that take less than an hour??? How old are you⁉️ Never, never, ever do this!‼️‼️ He likes you! That has already translated to money 💰 in your Life.. Personally, if it were me (Boomer) I would be going to his house, Golf Course & making sure to be introduced to as many folks as possible... This right here can change your freaking life many times over.. Please, please ask somebody you respect.. I am stopping just short of calling you out your name, because this is so unbelievable ‼️ I just hope you listen to good sense...

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_commenter@reddit

this is exactly my thinking as well... he's kind of an elderly friend. my thinking would be "would I do this for an elderly friend"? I'm not going to do your taxes but I'll set the font on your iPad to extra large... given that I would NOT feel as though it was a task assigned to me, I'd work out a time to do it around my schedule.

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NoFlounder1566@reddit

Damn, wish I had that for a boss. Our bonus this year was half of last year, our bosses got 10x the bonus we did, we havent received raises but the company saw about 60% increase in profits. I still get calls/texts when I am off the clock/on PTO for a "quick question", of which I now ignore.

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re10pect@reddit

Sounds like at least the former CEO considers the OP something of a friend, but the OP sees it differently. If it’s just the occasional small ask, I would almost certainly keep doing it, first for the good things it seems like the ex-CEO has done for them in the past, but also because that kind of person probably has a massive network of people they have influence with, and continuing to be in their orbit may yet yield positive things going forward for the OP.

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RealVenom_@reddit

I feel like this sub has the best take based on all the top replies. Every time I read a post like this anywhere else the top comments are like "babe, know your worth, cut him off". Whereas here we are with legitimately good advice.

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Thundernco@reddit

If he was successful and well liked, his sphere of influence doesn’t end just because he retired. In some cases it actually increases as they join boards, and do other things to keep them busy. You never know when a friendship like that will pay large dividends. I would continue to help as much as possible. Sounds like a good person, and a good person to have in your corner.

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yoho808@reddit

It almost sounds like OP owes him a lot and that they're in a friend/family level relationship. OP should do the right thing and do these small favors. It's paltry compared to what his ex-boss has done for him.

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GypsyBl0od@reddit

Agree 200%

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CHANGO_UNCHAINED@reddit

He doesn’t owe him anything. They had a contractual relationship. OP did his job and the CEO approved salary and raises for this service. They could still be friends. But that’s a separate matter. And by the fact OP is asking for advice on how to shake him off, it doesn’t sound like they’re actually friends. Still, In terms of advice. OP should probably bite the bullet. Because that’s the kind of world we live in.

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BicentenialDude@reddit

Look at this ungrateful asswipe. That’s why your life sucks and you are a bitter person. 🤣🤣🤣

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Diedead666@reddit

maybe help his ceo FRIEND find a worthy person to hire for tech support that he can vet/vouch for before hand. Could even get a younger person in the door to said company.

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PM_ME_UR_BEST_1LINER@reddit

Maybe remove the randomness by asking him to have a few of his tech things for you to assist with the next time you're at his place. Set it up so you watch a football game at his place and do it while you hang out

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st0k3r_@reddit

I had a similar thing happen to me. I got out of college with a CS degree and a cybersecurity minor. Couldn't find a job anywhere, but for some reason this couple who owned a software company 3 hours away from my hometown really took a liking to me and gave me a tech support job. I worked internal IT and also did software support for the products they sold. I was always treated fairly, promotions and raises even when the company was struggling. They were the best owners I've ever had to this day. Anyway, they sold the company when they were preparing to retire, but I occasionally still got texts from them asking for help with their at-home tech. After all they'd done for me, I couldn't say no to them. Not to mention that retirement can be lonely, I think that was partly the reason too.

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Loony_BoB@reddit

The last sentence was my first thought, honestly. A lot of people have been talking about the benefit OP will gain by continuing to do things for the retired CEO, but I would focus on whether the retired CEO is lonely or needing more than just an IT hand. Maybe it's time to visit when he *doesn't* need something from you, OP.

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Quick-Bird-2183@reddit

You sound like a good person, appreciate for what others have done for you!

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BicentenialDude@reddit

You’re a good person to do that and deserve all the good you’ve gotten and will get.

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GoGetThatThing@reddit

This, help them out.. you will never know good deeds will payoff.

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mh1ultramarine@reddit

Does OP spend time with them outside of work other than fixing stuff?

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sufferableknowitall@reddit

maybe OP should try talking to the dude abt more than tech support. retirement can be lonely & boring for someone whose whole life was work.

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Ok_Discount_9727@reddit

This, sounds a good person and one to keep in touch/good terms with. Not that setting boundaries can’t be maintained but sounds like he’s come to expect it. I suppose if it gets out on hands (overnights/weekends) that’s when you need to weigh setting the boundary

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vikinick@reddit

Yeah, for a lot of family/friends that ask for tech help they usually give me a few beers or make me/pay for my dinner. In this case, you could exchange the favor for mentorship on how to be a better people manager/learn more about business in general. I'm sure even though he's retired, he'd be willing to mentor you a bit.

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amk1377@reddit

Agree. No polite way out of this and he does sound worth it.

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AcrobaticLadder4959@reddit

Agree he trust you enough to ask questions.

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krazylingo@reddit

lol yeah, I guess he didn’t wake to the fact they are friends not just coworkers

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i_do_graffiti@reddit

Seriously, I wonder if OP is autistic, or slightly autistic? Kind of a buzz word in the tech community but...

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UniqueIndividual3579@reddit

It's also great from a networking perspective, you might want a reference someday.

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hustlekrackenn@reddit

I agree. Also men like this know lots and lots of people inside and outside your industry. For a couple minutes you’d cut off your nose to spite your face. This is an invaluable reference

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AwsumO2000@reddit

this 100% .. work is about networking. Gotto deal with stuff like that

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Nomad556@reddit

Be helpful and keep a friend.

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Western_Objective209@reddit

Pretty heartening that the top comments are so positive. Helping the guy with IT issues once a week is not much, and it probably has a lot to do with the guy transitioning his gear over to personal from corporate

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AllOfTheFeels@reddit

100% this. Not saying this is OP, but people spout about having community and bringing back a village network, but what they’ve forgotten is that community takes effort and will mean that you’ll have to show up. Even when you don’t want to or aren’t obligated to. I’d 100% help their mentor when I’d be able to. Obviously it’s up to them to put up boundaries and indicate when they’re busy, but if I’m not and I see the person as a friend then why not.

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LickyPusser@reddit

I wouldn’t say they were friends, but OP makes it clear the guy has valued him and taken care of him as a boss, which is great. Regardless, the founder retiring doesn’t mean the guy isn’t still the owner of the company given OPs description. He may have just stepped down to enjoy the fruits of his labor while handing the day to day operations off. If so, OP technically may still work for him, and if thats the case, I would have no problem continuing to field these kinds of requests unless the guy was being unreasonable with the frequency or intensity of what he needs.

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taewongun1895@reddit

The retired CEO certainly has connections with the people currently running the company. Having a simple connection like that, in exchange for an hour here and there, would be worth it.

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ThomCook@reddit

Yeah this once a week with tech support is the same relationship I have with my great aunt. We are close but this is kind of how we stay in touch nowadays. I literally think this ceo guy might just want to keep the relationship up because it helps him stay close to people he has known for a while. There are limits to this, and sometime people take advantage of you but the most telling thing is, do they hang out with you while you are doing the tech support. If you swing by and just do work for them alone thats wierd but if they make a cup of coffee or something and chit chat, yeah they are just trying to stay in touch.

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vt2022cam@reddit

What if the new company leadership doesn’t reward you the same way? Or you get let go? Is this guy going to be a future reference? How much time is it really? For a few hours once in a while, it doesn’t seem worth nickel and diming him over it.

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neverincompliance@reddit

also you don't know if this relationship will do you some good down the road-networking, references, etc.

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mjones8004@reddit

You received "multiple" five figure bonuses and you are on *Reddit* asking this hot garbage??

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Longjumping_Lynx_972@reddit

I think he thinks of you as a bit of a friend. Maybe feel it out my dude, he sounds like a great guy.

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CC_206@reddit

100% agreed, if OP can’t do something right away, reschedule or whatever, but I would help this guy out long-term no problem.

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RedOceanofthewest@reddit

This. If you enjoy his company, then spend some time with him. It seems like he always treated you fairly. You only want to say no when it's unfair but it sounds like that isn't the case.

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UnArgentoPorElMundo@reddit

100% agree.

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handsomeowl92@reddit

I agree with this. See if he wants to hang out next time. Maybe bring over a bottle of scotch and morph it into a fulfilling friendship. He’s not your boss anymore, now he’s a guy you (from the sound of it) and can get to know. I’m sure he is super interesting.

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dont_shoot_jr@reddit

I’m sorry I annoyed you with my friendship and employment -the CEO probably

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AncientPCGuy@reddit

I’d say so. But it would also be okay to ask for a time that’s mutually convenient, not IT on demand.

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gandalfthegru@reddit

He's also not the OPs boss anymore. Mistaking business/work relationship with real friendship is a mistake way to many people make. Unless the OP was hanging out with the CEO, going to events and parties he's no friend, barely an acquaintance. The OP owes him nothing. Business is business. Bill the ex CEO enough to make it wotg your while or politely say you don't have time with other priorities in life and send him to some local computer repair person. That's how I've gotten out of being personal support for people and its worked and I still have a good relationship with them.

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CruxOfTheIssue@reddit

I mean if he's that rich shouldn't he be paying for OPs time?

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rexmons@reddit

I agree. I'll add that if he's going to go ahead and continue to help the guy he should do it pleasantly. If you're going to act irritated or annoyed when doing a favor for someone then you might as well not do it at all. You're already doing the hard work, don't make them regret it by ruining it with an attitude. If it gets to a point where you feel like you're going to do that then politely tell them you can't, that you have too much on your plate right now.

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Select-Sale2279@reddit

He's put food on your table, he helped you buy your truck, he has signed hefty bonuses! What more could he have done not to deserve a little help once in a while. Fuck, I would do that his entire life if somebody did that for me. There is No "No" in this situation. You tuck your tail in between your legs and help him out! Don't grow that tail going forward!

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freebowlofsoup4u@reddit

Yes this 100% OP. Consider this a transition to mentorship. Suggesting you do lunch would be a good one. Use it as an opportunity to let him tell his story. It may evolve into one of the best relationships of your life.

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Marthaandthe@reddit

Don’t burn that bridge. People like your CEO are hard allies to find.

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PlumtasticPlums@reddit

I had this VP of IT at my first job who was a wonderful man. Like a genuinely good and decent human being. One word to describe him is "sweetheart". He'd ask me for help after they sold the company, and I was still there. I'd always help him. He did a lot of out integration and he retained a lot of our customers as customers in regard to maintaining and developing their integration. I helped him with that here and there so he would reach out for info or odds and ends.

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Firefighter55@reddit

Yep guy seems like a solid boss who helped OP a lot and he seems like someone asking a friend who knows things about stuff for help.

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Corgipantaloonss@reddit

Also like why wouldnt you want to be as friendly as possible to the guy with the name on the building? Just from a workplace standpoint. Like that guy sounds like hes still going to be in the ecosystem of this company even if hes taking a step back from the hot steat.

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KorunaCorgi@reddit

Ex-CEO thinks they're friends but op doesn't. From one pov it's kind of sad but on the other hand the op would obviously be friendly to his boss.

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Multi_Grain_Cheerios@reddit

You can always change perspectives. The guy is retired now he's probably bored and a little lonely if work has been his all for so long. Just be friends with him?

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PartTime_Crusader@reddit

If he's freshly retired also this behavior might ease off naturally after awhile, too. I'm at an age now where a number of my peers gave retired and some percentage keep up contact in the first few months. Almost all of them end up scaling back after that, though. They end up getting busy with other things eventually. If I was in OPs shoes I'd just give it some time to play out

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DonAsiago@reddit

Exactly. OP, stop being an ungrateful bitch.

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x01660@reddit

There's all sorts of currency. Monetary currency, knowledge currency.... And social currency. You've got a literal CEO who likes you for your skill and charisma, in your pocket. All he's asking for is some help with his tech. That's one of those "I know I'm benefiting more from this agreement, but let's roll with it" kind of situations. What CEO dude provides in social currency I think is worth your time fixing his shit. Of course, its my opinion, and opinions are like....

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MayorPirkIe@reddit

It's not social currency, it's social blackmail. Any career help he could give OP, he should already give him based on the quality of his work. It shouldn't be dependent on whether OP does free IT work for him. His relationship with the retired dude is being weaponized and used as leverage in case one day the connection can prove valuable, so OP needs to work for free to make sure he doesn't fuck it up? That's social blackmail.

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BeginningFederal5663@reddit

Go outside.

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MayorPirkIe@reddit

Why? Is that where my CEO master is, waiting for me to come shovel his driveway and be grateful for it?

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Theachillesheel@reddit

No, because you’re pessimistic and think like someone that spends way too much time online lmao.

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MayorPirkIe@reddit

Because I don't believe in working for free in the hopes I may one day get a cookie crumb, I spend too much time online? That doesn't make a lick of fucking sense

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A_Herd_Of_Ferrets@reddit

OP already stated that he has received way more than just crumbs from this person. This is not some fantasy, he knows that this is a person both willing and capable of advancing other people.

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MayorPirkIe@reddit

Yeah, when that person was executing the functions of CEO. I was friends with my current boss before we worked where we're at. I don't suck him off every time I get a raise or promotion because I earned them. OP doesn't owe this guy shit, he earned everything the former CEO "gave" him.

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A_Herd_Of_Ferrets@reddit

You fail to understand. This is not about "owing" something. It's about leveraging and maintaining a good relationship with someone who is capable of lifting you up.

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Theachillesheel@reddit

Bro stop being intentionally dense to prove a point. People help each other all the time. With that attitude of yours, you’d probably never be helped considering you don’t like helping others

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MayorPirkIe@reddit

Helping others is fine. This is a former CEO hitting up a former employee for help with his job functions for free. Does he cease to know the ex-CEO and no longer merits a reference if he doesn't provide free IT services? What the fuck is wrong with you people? Please tell me y'all are bots, this is insane

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Theachillesheel@reddit

Bro you need to ask yourself that and why good things don’t happen to you. You are speaking from a jaded point of view and are accusing others of being bots when some of us have helped others and have been rewarded plenty because of it.

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MayorPirkIe@reddit

Good things don't happen to me? Lol what the hell are you mumbling about?

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Theachillesheel@reddit

Then why are you asking if others are bots just because they don’t see shit from your perspective or agree with your approach? Like do you even read the shit you type? Cause you clearly don’t.

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MayorPirkIe@reddit

I was asking if you're all bots because you're not reading what I'm saying. You're just defaulting to "lol go outside" like children

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Theachillesheel@reddit

And you didn’t ask yourself why people say that to you?

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MayorPirkIe@reddit

Why would I? I've seen the way you guys think, why would your opinions matter one iota to me? Especially since "Go outside" is an absolutely moronic response to disagreeing with someone.

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Theachillesheel@reddit

No no no.. See that’s your problem. You spoke with absolute certainty. When others have had that social currency experience, you only view it as social blackmail. That’s why I asked if you even read what you write, because if your reply was already dickish, why would you expect others to treat you with respect? That just makes no damn sense.

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MayorPirkIe@reddit

Huh? I have no idea what this word salad is supposed to mean, but let me take a crack. OP posts his situation. People tell OP to continue providing free work to his former CEO as it is "social currency" and may come in handy in the future. Enter me, who tries to get you all to understand OP ALREADY HAS THIS SOCIAL CURRENCY WITH THE GODDAMN CEO FROM HAVING WORKED THERE FOR 5 GODDAMN YEARS. And that if the CEO were to withdraw this "social currency" if OP stops doing free work for him, then that's social blackmail. You're all treating the situation as 1 of 2 things. Some of you are saying OP should help the dude because "connections" and if OP ever loses his job, or if the CEO joins the board of another company, it could be an opportunity for OP. This is nonsense because OP didn't meet this CEO dude through the free IT work, they have a prior relationship. OP is already in with this dude. The others are viewing it as if this dude did OP favours while acting as CEO and OP owes him, which... well, lol. Hopefully that clears it up.

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Theachillesheel@reddit

You’re so close to getting it, but at the same time you’re not. Lmao. Almost /r/selfawarewolves material.

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MayorPirkIe@reddit

This is just more words that don't mean anything

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Unable-Surprise9412@reddit

I’ll help you out since I’ve been reading the context of all the comments. He’s saying you’re a dickhead and you’ve been a dickhead the entire time but somehow it’s lost on you why now other people are being dicks to you and you still don’t understand why for some reason. Hope that helps.

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yourbuttismydonut@reddit

Love how you just revealed your prejudices with this comment. I have issues with capitalism too but not all CEOs are evil. From OP’s description he sounds like one of the good ones.

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MayorPirkIe@reddit

LOL what prejudices? What the fuck are you talking about?

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Packet_Sniffer_@reddit

You know what rich old retirees do? They fund new business ventures. OP could very easily turn this into his own IT consulting firm and be the one paying 5 figure bonuses. Social currency is extremely valuable. Get off Reddit. Hell, get off social media. Your brain has been rotted by extremist rhetoric.

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MayorPirkIe@reddit

It's like you morons don't even know how to read. I'm not going to explain it again, have fun sucking up to your bosses in the hopes of one day getting ahead, maybe. You believe in trickle down economics, too?

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Life_Alternative35@reddit

yea the nepo promotions definitely aren’t going to the random dude he calls when he’s bored to fix his ipad. People are delusional

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Ok_Concentrate_1634@reddit

People help who they like, life is not a pure meritocracy and, to be frank, probably shouldn't be if that's your perspective on simple favors. The same kind of soft skills that make this a no-brainer to just do rather than ask reddit make you a better person and team member.

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x01660@reddit

So now in the real world, nepotism is a thing, whether you like it or not. Getting positions, opportunities, etc, based off of "who you know" is a huge deal. Now, if we're talking about whether or not that's "right", that's completely different discussion. But here, we're talking about what "IS". And what "IS" right now is the OP having a prime opportunity for some social/professional advancement. They'd be a fool to not take advantage. That's how the world works.

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MayorPirkIe@reddit

Why is this opportunity dependent on OP continuing to do free work, and not on what he's proven over the 5 years he's been there? Because it's social blackmail. I didn't say OP should tell the CEO to go fuck himself. But let's not pretend this is anything other than what it is, the CEO taking advantage of OP, dangling some potential future advancement that may or may not ever see the light of day.

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x01660@reddit

Let me give you a scenario: OP is out at a bar. Chatting with some friends. The topic of IT comes up. OP mentions to their friends that he still does the IT for CEO dude, on the side. Helps him out. At the same bar is the personal assistant to some high roller who just happens to need some IT help. Or the CIO of a tech company overhears that convo, and realizes that OP must not only have technical aptitude, but also social aptitude if the CEO is going to this guy for help with IT. Then all of a sudden, OP is getting a tap on the shoulder and a business card with the opportunity of a lifetime. It happens WAY more often then you think. Its calculated risk. Sure, it may never "pay off", but the effort involved is so low as to make it worth it. Plus, its ALWAYS good to know people that are/were in positions of power. Again, that's how the world works.

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Maxamillion-X72@reddit

Careers are made based on who you know. It's how you go from just another job applicant to a standout. Some people are born into the right circles, the rest of us have to work at it. If the former CEO called me up for tech help, I would jump at it. If the opportunity arises, I'd look for opportunities to just shoot the shit with them, like lunch or just delivering their tech back. The amount of insight one would gain would far exceed the effort required.

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MonoDede@reddit

This is true, but I also have to point out to anyone doing this that you gotta have the balls to ask for what you want when a real opportunity arises and the social connection can help.

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BigOs4All@reddit

Absolutely! It's pretty much a requirement. It shows those old rich dudes you have initiative. They're still the "firm handshake" sort of people.

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Tax_Evasion_Savant@reddit

> social currency which unfortunately has no value until it does. This is risk management. Do I do a bunch of free labor in the hopes of a pay off? Impossible to know.

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MountainTwo3845@reddit

People vastly underestimate how much social currency is worth. I try to help people out which leaves a lot of people owing me favors. I know a guy is my worth. It's gotten me some great jobs with great pay. My wife's friends don't understand what I do or how it works. She says it's like the Mafia without the crime.

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x01660@reddit

I'm in DC; this place EXISTS off of social currency. And that goes both ways; its a SMALL ASS town here. You ruin your reputation and you're DONE done.... Not gonna lie; its exhilarating having to be on ones toes all the time. 😎

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WhichWitch9402@reddit

I work for a Fortune 50 company and did a stint in the executive support team. Former CEOs that still have capacity even for just the charity type thing or honorary positions had company laptop/rablet and were entitled to support. Perhaps ask head of IT, current CEO or COO, and ask what the policy is. Or your direct manager. If he’s calling you during work it is a matter of taking up your time. If it’s on;y personal stuff, you might just need to say that you cannot help during working hours, but you could allot an hour a week to help out.

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jojames100@reddit

What's your position in the company might I ask?

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WhichWitch9402@reddit

I’m a systems analyst.

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jojames100@reddit

Sounds like he could use a personal IT on hand.

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THEscootscootboy@reddit

He’s your friend. Tell him to buy a 6 pack of beers and you’ll be over to help

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BlackPineGeneticsLLC@reddit

Dude made you, you owe him.

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sexyshingle@reddit

> Dude made you, you owe him. Geez a lot of ya sound like CEO bootlicking corpo-pets... **hard**... I'm not saying it's bad for OP to help the ex-CEO out, esp. if the guy was a decent human being, OP def should. But worshiping the guy CEO like a god and being a devoted little free IT slave forever because OP grew in his career there at that company is kinda nuts... OP has to feel things out and draw the line somewhere, somehow. As someone who's been in the "IT guy" in my circles, people (esp. very rich ones) tend to push boundaries and abuse you if you bill yourself as "free" and never say "no" or "I can't" ... ask me how I know...

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SalzigHund@reddit

I, personally, would likely help as you are now, however, you need to understand that it's perfectly acceptable to set boundaries. If he's taking up company time, talk to someone who's friends with him and can maybe bring it up or see if the company even thinks it's acceptable (anecdotally, they often do). If it's constantly after hours, then you say "Hey Mr. Bossman, I greatly appreciate all that you've done for me, but please understand that I have a family and a lot of obligations outside of the office and may not always be available--especially immediately."

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Phaedrus5@reddit

A lot depends on how he’s asking for help. If he’s always demanding you drop everything to help him, absolutely push back on that. But if he’s more like, “Can you help me with this?” you can say, “Sure, I’ve got some things on my plate right now, but I can check it out in a day or two.” Or whatever time frame. Is it usually something in his home environment that you could remote into? Setting up a remote access solution would make it easier on you. Or if it’s something with a phone or laptop that you need to put hands on, say “Sure. Let’s meet for lunch and I’ll take a look.” The implication being that he owes you lunch for helping him. But if he doesn’t offer to pay for lunch, let it go.

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Klutzy_Scheme_9871@reddit

Do you really think he’s going to be demanding?

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Phaedrus5@reddit

I have no idea. I've never met the guy.

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kirashi3@reddit

It doesn't matter what we think. The only thing that matters are the facts, which can only come from OP or their former boss's mouths...

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carrotstix@reddit

What's too much for you? I think that's a vital question to ask yourself. It is pissin annoying to be It tech support, especially for older folks as they can't be bothered to learn and just pass it on to you and I get that. I think it's best to come out and say there's things you can't do or uncomfortable to help with but if it's not too much of an inconvenience, do what you can to help. If it is, try to find him a solution that will work.

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Normal_Tour6998@reddit

If this is real, you’re being an asshole. This guy was good to you for years. Helped you afford the life you have today. Tell him how to connect to the WiFi every once in a while.

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hmtk1976@reddit

Pretty rude to call OP an asshole. Why?

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Normal_Tour6998@reddit

Read the rest of what I said.

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hmtk1976@reddit

The rest of your edited comment? Sure....

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Normal_Tour6998@reddit

Same words, but since you were having a hard time parsing out my point, I reformatted for you.

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swissarmychainsaw@reddit

"Sure, let's grab some lunch!" Also have a tech support contact handy "in case I'm not around". (that you have vetted)

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AccordingBathroom484@reddit

How is this even a question. Pretty selfish to not help someone who helped you so much.

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jmeador42@reddit

You can help him out, just as long as your current boss says it's OK, and it's on company time. Do not help this guy out on your personal time. You owe him nothing.

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Sensitive_Region_250@reddit

While this is true, it's sort of naive.

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jmeador42@reddit

I'm sorry, but no. In no industry should a former CEO should be soliciting free labor from any former team member. I don't care if it's IT, plumbing, or dog walking. It's out of line.

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Sensitive_Region_250@reddit

Great, hold the principle for yourself, but don't be shocked when when people start to treat you differently.

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nothingtotype@reddit

What exactly is naive about this, dude? You're just being passive-aggresive without explaining yourself. Childish.

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spacedman_spiff@reddit

You should sort by "Top" and see why people think this is a good idea to maintain a personal relationship with a former founder/CEO of the company where one is employed. From there, you can draw inferences why setting a hard boundary and the notion that "you owe him nothing" is naive.

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nothingtotype@reddit

Where Is your argument? Yours , not someone else's, or did you really just search the "top" comments to not have to think for yourself.

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spacedman_spiff@reddit

I see someone didn't resolve to not be an internet dickhead in the new year. My argument is similar to the ones to which I was directing you. But since you require redundancy, I will oblige. OP is effusive in their praise for a boss who was professionally supportive and to whom "I feel like I owe the guy a lot". >He's always been extremely appreciative of my work **which I value more than almost anything else** because **it hasn't always been the case in my career**. This person has their name on the building and clearly is very influential: >"He's friends with all the other execs (some of whom I have done some side work for) and I will be seeing him at company social events for as long as I'm here." So we have a CEO/founder who has taken a personal interest in OP and their development, who has been appreciative of their work beyond just simple renumerartion (which was ample), and seems to like OP personally. This goes beyond professional relationship; this is a mentor who perhaps has more to offer in retirement. From a personal or professional POV, you don't burn this bridge. If the trade off for personal fulfillment, financial security, and professional development is "accept\[ing\] that I'll have to help him with his shit occasionally", my vote would be "yes". HTH!

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rxs126@reddit

I’m surprised to see how many bad answers have been here. Just because this guy is retired doesn’t mean he doesn’t hold any influence or sway with the company or other companies. Do some minor tech stuff for this guy along the way, leverage the relationship for personal or professional gain another time. Want a promotion, ask him to put in a good word. Applying elsewhere? A letter from a this guy might secure a job. People on Reddit constantly seem like they have no relationship skills or knowledge. If this guy is really invested in OP, then his network can become OP’s network, and that’s worth some minor tech help. Saying things like you dont owe him anything is naive and immature. No one is 100% self made. Everyone gets help along the way from someone.

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spacedman_spiff@reddit

\> People on Reddit constantly seem like they have no relationship skills or knowledge Fucking nailed it.

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Sensitive_Region_250@reddit

Exactly. You might say they are....naive.

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Sensitive_Region_250@reddit

Huh? You ever consider I have other things to do than read Reddit? Weirdo.

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NecroGi@reddit

Why do you think it's naive?

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CarpetReady8739@reddit

$95/hr

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Bigassnipples@reddit

This guy sounds amazing. Dont cut ties with him, just slowly detach from tech talking and do more friend stuff

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Illustrious_Plant581@reddit

Help him with his shit, but set yourself reasonable limits.

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TurbulentNectarine94@reddit

Do NOT say no. Show your gratitude for what he has done for you and your family. I agree with another post about letting your boss know. You never know where this could lead for you

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Chief-_-Wiggum@reddit

Sounds like low effort help for continued bonuses at the company.

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narcissisadmin@reddit

I have the exact same situation as you, except I no longer work for that company. He touched so many lives with his generosity that I will always answer his phone calls.

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setsunasensei@reddit

How often does he ask you to help him?

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chefboiortiz@reddit

Wow I’m not sure how this is a question. I help my older family members with this stuff just so they can turn around and say that my generation is lazy and hates working lmao. This guy has lots of power, has helped you out and wants to keep in touch essentially? This is a no brainer

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hotonpot@reddit

Sounds like a small price to pay for an excellent contact . Plus, he seems to have taken care of you for years . Put yourself in his shoes. How would you feel if an employee/friend cut you off after all you’ve done for him? Even though it sounds like he could break you with a phone call, maybe you could see him as a person first and former boss second . TLDR: stop being an ass

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Free-Atmosphere6714@reddit

If a friend needs help, you help them.

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Regular-Lack6101@reddit

This is definitely him trying to be friendly, Invite him out for a beer or something. Wouldn’t hurt to have a retired wealthy dude as a friend either.

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Shoose@reddit

Fuck me 5 figured bonuses and your questioning a couple of quick calls, my bro, don't bite the hand that feeds you.

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Mammoth_Ambassador85@reddit

I say boss man is worthy of the help once in a while. He’s seemed to truly appreciate you. Give it back to him.

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drew2f@reddit

Absolutely help him. The more you can do for him the better. It sounds like he did a lot for you. His ability to help you did not dimmish completely when he stopped being CEO. Ask him for some pointers, ask him how he would solve certain problems, maybe he can be your mentor or put in a good word with the execs that are still there. Don't burn that bridge, built it bigger!!!

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Aliens_Are_Real978@reddit

There's only so many questions he can ask. Shifting into retirement can be really difficult for people. Maybe staying in contact with you is helping to ease the transition. I say give it time. I think it'll fade.

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Hot-Apricot-6408@reddit

Are you retarded? Don't bite the hand that feeds you, fool.

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Distinct_Science_854@reddit

Like this "no"

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NefariousnessNeat679@reddit

Dude. He wants to be friends and this is the main way he knows how to interact with you. Retired guys struggle with social stuff.

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Additional_One_6178@reddit

I don't even know why you're questioning helping them out. He's done so much for you - the fact that you're even wondering whether you should help them out or not shows type of person you are. Some people are just so selfish. Jesus Christ.

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tsardonicpseudonomi@reddit

>I feel like I owe the guy a lot. You owed him your labor. He paid you for it. What the fuck are you talking about?

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solen-skiner@reddit

maybe find some guy whos great at that kind of jobs, and link them up

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needGuidance792087@reddit

Don’t burn this bridge. If you need to put him on hold and not respond immediately, okay, let him know. Otherwise help him out.

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MaisonValoryn@reddit

Sounds like youre ungrateful.

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Think_Judge2685@reddit

Isn't this guy your friend? If not, maybe be honest and tell him he's not.

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vincentsigmafreeman@reddit

Just do it

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Usual_Category5687@reddit

I believe you can do what you think you should do in this situation that youre involved in

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Atrium-Complex@reddit

At my last company, we continued to provide private IT support for our founders and some of their family for years after they retired. To include a last minute flight down to Florida to get their condo tech all setup. You aren't so much doing them a favor personally, as it is the company offering a favor to the individual who gave you all a reason to be there in the first place. Just make sure your manager/management is aware of it. If they do not want their IT resources taken away from business focus, they should communicate that to the CEO, not you.

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dzfast@reddit

This is the best answer.

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deedsnance@reddit

Also, from a purely transactional nature and just ignoring that it’s a nice thing to do, this is someone I would absolutely want in my corner. You ever lose that job who do you think is gonna notice? Never mind all the potential other social connections and political capital that this guy potentially has. I would likely provide IT support to this guy on my own time if it came down to it. Depends on the frequency and time commitment but I might just lump him in the with “close friends and family personal-SLA.” Not everyone has personal access to execs with extensive professional networks. Worth keeping around😉

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pollywirl@reddit

Right, chances are if the CEO was this good to OP, he was good to many other employees, including OP’s superiors. If this is the case, the superiors will likely understand and support this work on company time.

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PandaLaw@reddit

Agreed, this is relatively common practice at small companies. But there's no reason it shouldn't be an official part of your job, especially since the founder is still so plugged in.

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SweatyFLMan1130@reddit

For real. OP it sure sounds like this guy did a lot more for you than I'd expect from *any* CEO. And I've been involved with exec teams from multiple Fortune 500s. Don't fuck this up by cutting him off. Log the work and let your leadership know what you're doing and why, but telling him to bugger off yourself is just shooting yourself in the foot. And to be clear: boundaries are important. Good communication and healthy rapport are essential to relationships. Supporting others *does* have its limits for each person, and it can depend a lot on what your capacity is. *All that said*, we still live in a capitalist hellscape and being courteous to someone who has done all that to keep your job and status is insanely good fortune. I'm a data professional and developer in HR functions in the US. *You do not want to be gambling with your career right now*. I suggest finding the silver linings and building on this relationship. If you want to set hard boundaries, though, make sure you fully understand what that can cost you.

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Personal_Win_4127@reddit

This is way more valuable than anything else I've seen, "log the work".

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WhyLater@reddit

Yeah I almost wonder if OP would want to put ex-CEO's devices in their RMM or something to semi-manage them. Not domain-joined or otherwise having direct access to the network, of course. Might just be the best play.

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Shirohitsuji@reddit

This is the way.

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stupid_pun@reddit

That's a great idea, actually.

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Atrium-Complex@reddit

We did this for a very long time as well. Gave them their own separate policies and configurations so it's overall less invasive BUT they still got antivirus/EDR and we could easily remote in for quick fixes.

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Elistic-E@reddit

It’s honestly a good idea - if the ceo gets compromised an internal phishing email from him, his credentials, etc is going to be quite successful to exploit

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AlienDragonWizard@reddit

I would figure out what kind of situation it is before making the decision to bring it up with the company. Could cause problems if this is an off the books type thing. Wouldn't want to unintentionally offend the retired CEO.

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Natural-Gur40@reddit

I worked at a company which provided It services to several sub sets of related businesses (professional sports team owner had associations with businesses of retired professional players and their business interests). We did work for many former executives, related businesses units who had spun off into separate companies, work for private projects of the owner family, and so on. None of these were unknowns to the CIO, most were easy and non intrusive, only two were massive pains in the ass but were part of the game. I’d personally use the contact as a way to talk about start ups you want to create and see if he can get you into circles of other entrepreneurs.

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trick_m0nkey@reddit

This is it. My first company the semi retired Owner/Founder pulled me away multiple times to do various jobs that were of a personal nature. For example, one time I was requested to set up a home office for him in his brand new condo on the beach. I got to stay a Thursday and Friday at his new condo right on the beach in exchange for what was not much more than a regular business day's work. There was a 5 hour drive involved too, but the company mileage policy was something like .50/mile, more than enough to cover gas and put a bit of extra money in my pocket. And I got to comp my meals. The bosses were fully aware and onboard. And I got to get away from the constant office IT crap, and forward emails/requests to the rest of the team. As long as the bosses know, they can set the boundaries. If you feel boundaries are being crossed, talk to the bosses.

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BelowXpectations@reddit

This is true as long as he's doing it on company time and pay. If it's in his spare time it's a personal situation, not company.

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ISLITASHEET@reddit

>This is true as long as he's doing it on company time and pay. Little nitpick: Flying to a personal residence to do non-business work on the company dime is potentially fraud (dependent on the business and how they classify that expense). Can't just use business funds as personal slush funds. This is not really a personal issue for the workers unless they are in finance misclassifying the expenses or personally making the decision to misclassify the expenses that are reported to finance. >If it's in his spare time it's a personal situation, not company. And this is how you maintain a good business network. Friends in your network are 1000% better than business-only connections.

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HarveysBackupAccount@reddit

> You aren't so much doing them a favor personally, as it is the company offering a favor to the individual who gave you all a reason to be there in the first place. Just make sure your manager/management is aware of it. If they do not want their IT resources taken away from business focus, they should communicate that to the CEO, not you. This is the big thing. It's a bigger ask if this is happening on OP's free time, but if it's during work hours then hell yeah keep supporting him until current management says not to

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ArcticFlamingoDisco@reddit

This is the way. Let management know and let them be bad cop if the company doesn't want to be supportive. In mean time, good connections are worth their weight in gold.

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sir_mrej@reddit

Maybe the CEO is asking for help after hours, which would mean your comment isn’t as relevant

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Klutzy_Scheme_9871@reddit

Even off hours I’d help him.

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Intrepid_Speech_1157@reddit

Do it for him, it's hard to step out . Also sounds like he likes you.

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jou-lea@reddit

He treated you pretty well when you were his employee; I’d return the favor now that he’s retired. You never know what good comes from a little generosity with your time. Bite the bullet with a smile on your face.

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SaskrotchBMC@reddit

Do you like the guy? Seems like it. He’s probably bored af and lonely potentially. Set a time to help him out and chill with him for a bit.

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HeldNoBags@reddit

what do people need to ask reddit about basic rudimentary human experiences help him, asswipe

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headrush46n2@reddit

You're stuck.

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2beatenup@reddit

He trusts you!!! You can’t put a price on trust. And also do it for ole times sake… don’t let old rich friends or colleagues fade away or put barriers.

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SSgtWindBag@reddit

I'd help him out. He sounds like a good guy to work for.

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Profil3r@reddit

Give him a decent referral. Find someone online who does these kinds of services for seniors and pass the name along. Hopefully he’ll get the hint.

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qqererer@reddit

Add friction and sludge. Most of the resentment usually comes from the expectation of immediate and unscheduled interaction and resolution of whatever issue at hand. Don't answer the phone immediately. Let it hang up then call back immediately. Later, let it go to voicemail, get a notification, then call back immediately without listening to the voicemail. Later let it go to voicemail, and call back a minute later without listening to the voicemail. Later, wait 5 minutes. Later wait 10 minutes Amongst all these calls, the expectation is that the issue is resolved on the call, so now introduce scheduling. "I just wanted to call you back [right away, 5 minutes, 10 minutes] after your call just to get in touch, but I can't deal with it now, can I call you back to resolve this when I'm free from what I'm dealing with right now?" Text follows the same script, of course, without voicemail. Add email. "If I don't get back to you soon enough, try me on email, because I might have put my phone down but email is on computer and I might get back to you faster. Occasionally, on any of these, answer immediately. Occasionally add: "This sounds like something I can address, but you owe me lunch. Let's save up a couple of things, and we'll meet up on x and fix these things, then you take me out for lunch. Always lunch after so that you fix things fast, then after restaurant, you can split without doing the awkward leaving home ritual.

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DelAustin@reddit

Send human invoice for your time, then you will know!

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gfraud@reddit

Little computer help and he'll recommend you to paying clients.

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shred_til_im_dead@reddit

Start calling and asking him for stuff.

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blue_rip@reddit

May the bridges I burn light my way. This is a unique case, I would at least entertain a visit or two and see it where it leads. If you determine he is truly using you and doesn’t expect to compensate for your time revisit the relationship but based off your previous interactions I have a feeling you will be rewarded.

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Feeling-Being9038@reddit

Do it, you can throw up barriers later, and I’m sure he isn’t an island out there, and may open up future opportunity.

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milezero313@reddit

I think without a doubt I would just help the guy, he sounds like he has been a great person in your life and it's probably a pretty cool friendship anyway, continue to help the guy and make sure you manage your time like don't let this take up a bunch of time and cause problems in your life but a few minutes here and there is great!

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iDestroyedYoMama@reddit

Just help him out. I’ve done this in the past with CEO’s where I’ve quit or they retired. They’ve always hooked me up one way or another because of the help. They know your time isn’t free. Trust me, don’t burn that bridge. And what better reference than a CEO on your resume. It’s annoying sometimes but always pays off.

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DeputyDomeshot@reddit

Uhh based on what you just wrote here- help him fix his fucking iPad dingus

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dlongwing@reddit

The top comments are all like "Help him out! Whatever! He's a buddy!" but I completely understand your frustration. Whether or not you like the guy, he's asking you to do work for him effectively for free and likely after-hours. That screws with work-life balance and makes it feel like you're on call 24/7. Since it sounds like you've got a good relationship with the guy and he left on good terms, I'd make a suggestion: Have him contact you at your work contacts (work cell or extension, work email), and respond to his requests during business hours. Talk to him about it, and try to coach him to contact you while you're at work. That way, you can treat his requests like helpdesk tickets from a VIP without it eating into your free time or sanity. He gets the support he's looking for, you keep the relationship in good standing, and you don't feel like your evenings and weekends are being eaten by helpdesk requests. Basically treat it like he hasn't left, but set limits on when you'll respond to him.

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suzenah38@reddit

OP, I counsel do not do this. If it’s something that you can’t do right then tell him when you can. You do NOT want him to stop calling. Fwiw he sounds like a friend.

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dlongwing@reddit

When did I say to tell him he's a pain or a chore? Just steer him into calling you during office hours for IT-related issues. "It's when I have all my tools and utilities so it's easier for me to address the issue" done. If this guy really is a friend, he'll understand. If he's the kind of "friend" that's only friendly when you're doing something for him, then it's time to set some boundaries.

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No_Kangaroo_5883@reddit

Your post answers your own question.

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cheech712@reddit

Noooooooooope. Tell him, "this is the last free work, all other requests will come with a quote and invoice."

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PhatVibez@reddit

This is such a fucking pathetic attitude lmao

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Zkrump@reddit

Right lmao people have this weird mindset then get confused when they have no friends. They always have to make everything a transaction.

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niagara-nature@reddit

Reddit is weird in many ways. You have people who’ll advocate so strongly for really strong, definitive work-life boundaries and they’ll upvote each other when they say stuff like “I don’t socialize, I’m not at work to make friends, I don’t do overtime, I mute my phone at 5pm every day, etc” Yes, boundaries are important. But I also think — if you got a flat, and needed a ride to work, what do you do? If you need to leave 20 minutes early, what do you do? Are you working in a place where nobody knows anyone else, nobody has anyone’s back, nobody cares if you’re there or not? That seems sad to me. I imagine places like that have high turnover. I’m friendly with two of my most recent past bosses and would gladly help them out for free because they’re friends, and they are also still connected and throw networking opportunities or actual work my way from time to time. Of my eight current colleagues, I’ve worked with four of them for about a decade. We’re a good, cohesive team. My supervisor went to my *wedding*. We all frequently have after work drinks and stuff like that. When someone’s *pet* dies it’s not even a question if they need to take time off. Give me that kind of workplace a million times over one where I clock out and never think of my coworkers again. They’re not adversaries, they’re friends. And I’m glad for that.

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spacedman_spiff@reddit

Also monumentally stupid considering the influence he has over OP's current employment.

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SalamanderCapable183@reddit

Help him. And every time you go help him, ask for more advice. Something you don't understand, something you're just curious about. It goes from being one-sided, to genuinely beneficial for you. He has the connections, the knowledge, and the ability to help you in your career. This might actually be one of the most important relationships you can develop for the next decade.

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Express_Meeting_9553@reddit

Seems like you're a selfish asshole tbh

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Jswazy@reddit

You should probably just help. Sounds like you like the guy anyway so why not

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Techie4evr@reddit

Your call. I know i would. I mean with his connections, you could still get far in life. I call it "tit for tat" so i wouldnt feel guilty about it.

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edwardsanders2808@reddit

Just help the nice old man with his tech stuff ffs.

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VarthDaderSG@reddit

Be grateful dude

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InconsistentEffort2@reddit

Wow, of all the times to not be anti-work. Dude helped you, boosted you, fostered your growth, used action to show he valued you, groomed your career... Fucking do it dummy. Or give him my handle, I'll do it for a modest fee and some contacts at your company...

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AdRecent7021@reddit

To approach this pragmatically, I think it's worth it to keep helping him. Sounds like a good connection to maintain. To approach this emotionally, it sounds like you two have maintained a good relationship, so probably not worth losing that either.

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ssreye@reddit

Sometimes you need to be a friend to someone who you appreciate. OP, maybe check a therapist to see if you’re a narcissist.

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mlang7769@reddit

He sounds like a good guy who treated you well. I'd help him out. The single most important thing in business is your connections. He sounds like the type of person you'd want to be on their good side. You never know who he knows or what connections he could set you up with in the future. That line about trying your best and blah blah will follow, it's complete BS. Connections and luck are what make people wildly successful. Of course you have to know what you're doing to some degree.

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YankeeDog2525@reddit

It all pays the same.

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wearyshoes@reddit

This man helped you your entire career. is a five minute conversation twice a week so much?

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3xlduck@reddit

if it's only once a week, then yes.

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Many-Wasabi9141@reddit

I'd keep helping him. You never know when you might need a letter of recommendation or some help in a tight bind. Some networking for a new job? Sounds like good contact to have.

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mike-foley@reddit

If your boss has no problem with it then continue. I guarantee that the ex CEO has better networking connection than you. Should you need a job in the future he could help. If your boss has an issue with you helping then tell him to deal with the CEO.

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cec263@reddit

You owe him nothing. Block him. He’ll think he’s just bad with technology and can’t work his phone.

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Weird_Collection_256@reddit

Just to peddle another idea: What is this guy doing now, after retiring? Could it be that he’s feeling a bit bored? Needs an informal connection to his old stomping ground but knows that his immediate successors are too busy for a chat once a week? TBH, from what you store in your post, he seems to like you and your work. Don’t burn that bridge, give back a little, and help him out. Maybe ask for a lunch once in a while as the “friends and family” rate for IT support. I had an ex-boss like that a while ago. He “paid” me in Vodka. 😅

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Corporate-Scum@reddit

CEOs are useful people to know. Can’t hurt to keep him on good terms.

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Sad_Scallion7315@reddit

Keep him In your corner

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Fit_Willingness_560@reddit

Don't answer your phone

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theitguy52@reddit

I've had this happen to me more than once. My advice is to help out. Over time, the calls will become less and less frequent, and itll circle right back around to being nice to hear from him. Its gonna be a lot of calls initially. Its a transition period for both of you. He doesnt know how to be retired yet, and doesnt know how to work without an IT staff, but he will learn in due time

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castle411@reddit

He didn’t do you any favors. He paid you to do a job. You don’t owe him anything. Help him if you want to but don’t feel obligated. If anything, he owes you for your ongoing help.

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HealthNo4265@reddit

If the guy founded the company, are you sure he doesn’t still own it? A lot of founders retire from day to day activity but still own the company that others are running for them. There seem to be other reasons to keep helping the guy, but if he still owns the place, telling him to bug off would be more than just burning bridges.

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Joshallister@reddit

He’ll be gone eventually. Just enjoy offering him support until he doesn’t need it anymore. Sounds like a solid guy

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Joshallister@reddit

Teach him how to fix stuff, don’t just do it for him though! Utilize every interaction as a learning opportunity

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lumberjack_jeff@reddit

Is this guy a friend? If so, answer the phone.

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Beam_Me__Up_Scotty@reddit

That's a no brainer

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simpaholic@reddit

"this guy changed my life and could continue to do so, should I help him out with a menial task 4x a month"

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HeyItsJustDave@reddit

If it were me, and: - he’s not being disrespectful or demanding - I have the capacity / free time - boundaries are respected I would bite the bullet. But try making it less like a bullet and more like pizza. No matter how bad it is, it’s still pizza.

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HectorCruzSuarez@reddit

He’s really calling that often? I even think he does not need help with anything, he just wants to chat with you since he must be bored and missing you. Take him out for coffee.

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Cautious-Flatworm-@reddit

sounds like he trusts you, honestly if I were him and I read this - I'd be disappointed and embarrassed by how you feel and are talking about him. It feels like you are where you are in life and the way you describe it as that you owe a lot of that to him directly. Doing minor "tech support" feels low stakes, and something you'd help any friend with. not every transaction needs to be dissected, and it sounds like he values your input and company. definitely "bite the bullet" though phrasing it that way both internally and externally may lead to a negative mindset. just be nice brother, sounds like he has been to you.

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yaderkuvboloto@reddit

if this dude helped you so much and he's the founder and you even still see him at events, just help him out lol, it would be really silly not to

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Spicyg00se@reddit

Man, I really appreciate some of the lasting relationships I’ve made through work. Like, really important people who have done great things and I sometimes feel honored that they even give me the time of day. This is a relationship that personally I would keep and be very honored to have.

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ryan__joe@reddit

Take it a step further, and while you’re fixing his stuff, casually mention you desire to continue to climb the administrative ladder.

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jl2352@reddit

If he’s calling you, he’s probably calling the other execs. Ideally I would strongly advise helping him. But it depends on the time involved. If it’s a lot then I’d make that point to him, it’s a lot of time, and that you can’t spend that much to help him in your own time for free. That feels like something reasonable he would understand.

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IsadorCZ@reddit

Become a friend and then be a IT guy on call for life.

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Miserable_Potato283@reddit

My dude - be a friend, he sounds like someone who you want - and is - in your corner. And I will promise you he still has political currency in the org since he's retired.

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tankerkiller125real@reddit

And there's always the chance he gets on the board of some other company and can use political capital there to get you an amazing new job potentially.

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twilighttwister@reddit

He's probably still the owner and on the board of the current company, just in a non-executive function.

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NotAComplete@reddit

Almost certainly, op said they retired rather than sold the business. Unless they misspoke, he still owns the business. He doesn't want to deal with the day to day issues is all.

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RevolutionaryHumor27@reddit

dude probably doesn't even need help. He has people for that, he just likes OP and wants to connect.

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11hydroxymetabokite@reddit

He is effectively the CEOs boss

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industrysaurus@reddit

Not saying this for interest But keep the friendship, it’s going to be worth it

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Tunelowplayslow@reddit

There's a lot of possibilities leaving that door open and walking through it A heck of a lot more than closing it and walking passed (in your mind), thinking: "what if?"

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FlurgenBurger@reddit

OP must be high on the autism scale.

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rads2riches@reddit

Yeah I was ready to say heck no way you should you put up with that then I kept reading. CEO seems like he helped you in every way possible so return the favor.

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Ok-Librarian6629@reddit

The networking capital of having a former CEO on your side is a gift. If OP ever needs a new job or a good word having the CEO in his back pocket in invaluable.

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Phluxed@reddit

He retired 2 months ago! He's still half running the company with the new CEO calling him probably multiple times a week still.

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gsmitheidw1@reddit

Somebody at that level is probably going to struggle to fully retire in the short term. I think it can be a difficult transition for some going from such a busy position to doing nothing. Without a good support programme from HR to settle people into a fulfilling retirement, he could get bored or even a bit lonely. It depends on the person, some people would have plenty of hobbies and maybe work in a different field altogether at a slower pace. I'd certainly not mind doing a bit of remote tech help for somebody I got on well with at any level of a workplace. Sure you go to work for money but it's human nature to make some friendships along the way.

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zhannacr@reddit

Yeah, for sure. I've met a lot of men who were all raring to get into retirement and the I talk to them six months later and they're bored as fuck, spinning up and LLC for something to amuse themselves. This guy sounds pretty solid and he's been good to OP. I wouldn't be surprised if the owner has a genuine interest in mentorship and is partially keeping the line open for when he's a bit more settled into retirement and has real time to devote to helping OP develop.

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Miserable_Potato283@reddit

Don't forget that professional dynamic has now changed, he's no longer your boss but might see something in you that you don't yet see in yourself (if you're young!) Learn and be in the moment.

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ouchmythumbs@reddit

I would capitalize on this and ask him for advice and guidance in setting up an LLC for a side business in the most sincerest of ways. He’ll prob be pleased with your ambition and enthused to get you going by being your first client.

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Sharp-Okra-54@reddit

Exactly what I thought. He’ll think you’re a lot like me and want to invest in you.

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ethnicman1971@reddit

this is a good point. OP can see if he would be willing to mentor him in his career. He doesn't have to specifically say it is a quid pro quo but if he agrees to mentor him then doing some occasional tech support will be worth it long term.

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mahsab@reddit

Nah, probably set everything up long before that. People plan for retirement months or years ahead.

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actingSmart@reddit

This, and therefore helping him with his email, phone, etc could still be ~related to him interacting with your company. So maybe his email + email security might be something of import to you, as it relates to the business. Maybe!

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Puzzleheaded_Fold466@reddit

And the customers when they’re not getting what they want from the current CEO …

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Doyouevenyugioh@reddit

Your network is your net worth. I understand that there is likely more “bad and or abusive” working situations than good ones, but the internet has rotted a lot of people brains with “CEO bad”. Not everyone who has started a company, or is the chief exec in one, is a robber baron. This former exec sounds like a good person to maintain in positive network standings with.

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Whatever5588@reddit

This type of thinking is transactional & frankly pathetic! A good man will do what is right & take care of leaders who mentored you.

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Redman2010@reddit

You’re right. He most certainly does still have political currency. Smaller companies still consult , trust the opinion and sometimes even go to for who to hire when it comes to top level staff

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EyeCorrect3300@reddit

Political currency lol it’s called Social Capital.

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throwaway_t6788@reddit

he was in OPs corner . but he is retired. not suggesting op shouldnt help him because of ceos past stuff but doubt ceo will be helpful in future

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b1ack1323@reddit

If anything negotiate a dinner or two out of it to keep the connection tight. I still text my last 3 CEOs monthly and go to a company party for a place I left 7 years ago. If I lose my job I am not worried in the least, I have a network of connected individuals who will pick me up in a heartbeat.

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MRRRRCK@reddit

This is a great comment. I feel like a lot of guys in the IT field lack this kind of long term strategic thinking.

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Kingflamingohogwarts@reddit

Important to mention that OP said retired, which is different than "sold his ownership shares". He can absolutely be retired, but still own 100% of the company.

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Barachan_Isles@reddit

This so much. All he did was transition from boss, to acquaintance/friend. Always good to have someone like this in your corner. Fix whatever he needs and one day it'll come right back around for you when you least expect it. That's how life works.

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Ok-Strength-5297@reddit

changed to guy he texts when he has a problem, there's no friendship

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elevntoes@reddit

Definitely agree with someone you want in your corner. This might actually be a good thing because you won't lose touch and you can probably call on him for favours in the future.

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pngbrianb@reddit

Yeah, my first instinct is always "fuck bosses," but this relationship sounds like it's worth keeping. A little tech support help doesn't sound that bad, and if it's a way to keep in touch great! This boss is probably keeping in touch with others in the company too, so might even still be helpful on a practical level

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juciydriver@reddit

Agreed. I supported a former owner for several months after the business was sold. When he bought into a new co he recommended me to lead IT. Partners liked me and I got the job. Much better money.

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mrdeadsniper@reddit

Yeah that's what I was thinking reading this.. You should WANT this guy to keep you in his rolodex as even if he is retired, his circle is likely to invite other opportunities later. Setting up an ipad/phone a few times year is pretty cheap networking time investment to keep your name on a CEO / Board level list of contacts.

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Valdaraak@reddit

I'm with this guy. OP, that ex-CEO is *absolutely* someone you want to stay on good terms with, and maybe even try to build a friendship with. Guy like that has connections and weight. Most of us would kill for that stuff.

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Puzzleheaded_Fold466@reddit

Not only in *this* org either. Chances are he can help them find their next job too, in another org. These folks have solid networks.

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VeryRealHuman23@reddit

Yeah OP has a mentor...and a well connected one. Next time he calls you for help, say "hey, happy to help - how about i come over on Saturday and we drink a couple beers and get this sorted out"

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libertyprivate@reddit

So much this. This guy has been great to you; be great to him! You should not need to be told this.

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darcon12@reddit

Yeah, I'm all about helping people who help me. What irks me is when I help someone, then they are nowhere to be found when I need it. That's how my help blacklist was formed.

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kerosene31@reddit

Exactly. Honestly I see this a lot. They are probably "semi-retired" but if their name is still on the building, they are still a useful person to have in your corner, all for a few quick tech questions.

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tsaico@reddit

It is also possible he is bored and is looking for some of the interaction he used to get. It was a big change for him... We all dream of when we have nothing on our docket to get done for the day, but that is only because usually we have so much going on. He went from being the most important guy in the place, to being the "B Team" at home (stereotypically guys will work, but the household is ran by spouse). He might be just looking for some semblance of still being important.

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eggmonster@reddit

I’m 50/50 on this. Are they getting paid? I was in a very similar position long time ago. I had wonderful rapport with a lady who was one of the OGs who started the company who retired. She approached me and asked if I’d be willing to help set up some things at her new house while so she could work on some new projects and some light consulting with the company she just left. In my case thing, a private equity firm came in and gutted 90% of the C suite and other executive leadership. Any pull was largely gone. And when time at this company came for me to put in for a promotion when push came to shove, her clout was never going to matter anymore. In my case though she reimbursed me nicely though so I was happy to make some side cash from it. I think OP would know best if they think anything could realistically come from it, but at a minimum I’d make sure I was getting paid first.

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73tada@reddit

Pull at that one company was gone. ...But not at the 10 other companies where she knows someone. At that is exactly how your resume gets put in the good pile of 1-5 candidates.

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shadowpawn@reddit

Never hurts to have an ex CEO in your corner.

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mattmawsh@reddit

Well said, tbh I read this post with a different attitude on the situation than I had after reading your comment

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Rhylanor-Downport@reddit

Help him. He’s a colleague and a friend.

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bit_shuffle@reddit

You are saying yourself you don't want to say no. You like this person because they've been kind to you. So how about you say "Can help you at a scheduled time? I have pressing work issues/family event/personal time off I'm trying to pin down/use right now." Or "you've caught me running some personal errands, can we schedule a session to look at it?" Then schedule a session to support. Make it clear you have a "time box" with a "hard stop time" that you need to maintain. Also, it is not out of line to ask him to come to you or a convenient meeting place with the iPad/laptop/phone to eliminate commute time, especially since you're still working and he is not. A CEO should understand structuring one's schedule and commute, so he should respect that. That's a civil way to control your schedule (which is your real objective) while maintaining the pleasant and useful social connection.

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STAAAAAAALE@reddit

You're a bitch

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somedelightfulmoron@reddit

Dude this is one connection you do NOT want to burn. Career wise, he could still influence or play a major role in whatever you plan for the future. You want a stellar reference? You want more promotion? You want to branch off and start a new business? You will need to keep this connection. It might sound annoying but as someone who needs this type of social backing to move up, DO NOT put a hard boundary.

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terribilus@reddit

I've been a tech consultant for my first boss for over 20 years. He's long since retired and I left that job before 2008. I consider him a friend but I've considered cutting him loose from IT topics over the years. I'm just honest with him... Sometimes I'm too busy and will say as much. Others I'll send some quick advice via email. Sometimes I'll rebuild sometime of his to spend quality time together when we didn't catch up for ages. My role now is many levels above his role when I worked for him, so he gets it when I'm busy, but it's nice to have a common ground to reconnect us from time to time.

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PracticalLecture5637@reddit

He might just be lonely or something now that he's retired also. Invite him over for dinner or something to establish an actual friendship.

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bleedtension@reddit

He’ll learn, just help him a couple times and make sure he understands how things are done

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mrdavidrt@reddit

Damn so is this a what have you done for me lately type of thing or what? Sounds like a great guy. Sucks that you only want to help him because it would continue to help your career and not just to help the guy out.

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Red_Sleeve33@reddit

Dude, that's a good friend to have.

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Waldoatticus@reddit

I have a friend like this. I would never think of charging him or his family, all of whom I help.

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Vladamir_pootinn@reddit

Thats called ‘a friend’ You can tell him to fuck off if you want.. but if you’re the ‘tech guy’ then helping someone with an iPad or email is hardly going to take you much time

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my_name_isnt_clever@reddit

I never expected so many bootlickers in /r/sysadmin. Why is every other thread "it's a job, don't get invested, don't work for free, know what you're worth" but here it's "you owe him man don't be rude" like what?? I provide my labor for money, once someone leaves the org I don't work for him anymore and as far as I'm concerned we're even. He can probably afford to pay you and should, if you're that good.

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my_name_isnt_clever@reddit

Imagine if he called up a senior accountant and asked for them to balance his checkbook this month. Imagine asking his best PM "hey can you just manage this personal vacation for my family" or asked to borrow a sales guy to get the best deal on a new car. All of that sounds insane, but you all will work for free? Have some self respect for your career and your skills.

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englishinseconds@reddit

Presuming he treated the senior accountant as well as he seems to have treated this sysadmin, I’d guess the accountant would be happy to help, especially with something simple. He’s free to not do it, but this sounds like someone who treated him right, paid him well, and is just looking for some help getting set up for the next phase of life. It’s only been a couple months. Someone like that is valuable to keep in your corner, and I’m guessing he still has equity in the company, but it’s still a good connection to have even if he doesn’t. My gut tells me he’s a good guy, and probably starts offering to pay him if he keeps needing help. I’ve got a former boss like that, I usually just tell him to buy me lunch and continue being a reference if I ever need it.

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GoodhartMusic@reddit

Would probably be because of framing. This post is effusive in listing the ways. OP feels like somebody went out of their way for them. They even seem to phrase the job itself as a privilege. And at the same time, the depth of the tech-support request requested is not elaborated on at all. It sounds like it could be something that takes minutes. This former CEO is referred to as a guy, so he has an almost jocular framing, and he’s asking for help with stuff like iPads, which is neither complex nor indicative of somebody who is in a coercive position of power, rather sort of a bumbling, friendly know nothing. Who has given him five figures as a bonus. So all we have is a person who seems like they’ve only given OP good experiences and valued their labor / personhood. I don’t see why anyone would feel vehemently against providing minutes of support for someone every now and then especially because that person seems Like a connection that is more asset than liability.

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my_name_isnt_clever@reddit

There is no such thing as being the CEO of a for-profit business and not exploiting your workforce. It's just what happens when you voluntarily take up the highest position of power in a broken system and do nothing to fix it because "that's just how it is" or whatever excuse this guy uses. It's *possible* this guy is different, but he'd be one in a million. Anything that takes more effort than responding to a friendly text should be invoiced. The least this guy can do is pay OP for his time. And I truly mean that is the least he can do.

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GoodhartMusic@reddit

Personally, I’m always going to withhold judgment from people I haven’t met and know nothing about, but my disagreement with you isn’t relevant. The point I tried to make was that the framing of the anecdote is what positioned the comments to be overwhelmingly in favor of providing the support.

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Agent7619@reddit

You are severely misguided in life and career. Loyalty to a corporation is vastly different from friendship and recognition to a person of influence who has been supportive and appreciative of your efforts. At worst, this is "repaying the favor", at best it is cultivating a potential future opportunity. Successful people like that do not typically go quietly into the night.

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my_name_isnt_clever@reddit

There is no favor. OP was employed to do work and get paid for it, that's not a favor it's just the bare minimum to survive in our society. Cool he was a good dude, I still don't work for free. If corporate culture wasn't so cutthroat about employees and treating us like numbers in a checkbook, maybe I'd feel differently. But if he isn't a personal friend, he can find someone else to work for free.

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bencanfield@reddit

Friends pay going rate to support their friends.

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Legitimate_Put_1653@reddit

It has been my experience that when you need a job, an introduction or even seed financing for your own venture, it’s a hell of a lot easier to have a contact like this guy than it is to start from scratch. Besides, he sounds like a genuine good guy. The world needs way more of those, especially in tech.

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FortheredditLOLz@reddit

Dude gave you a career. Soft drop grabbing lunch while fixing it or your struggling liquor collection. Treat him like a friend imho.

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hmtk1976@reddit

I´m curious about the geographical distribution of the comments. The number of Europeans must be vanishingly low.

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NoPlaceForTheDead@reddit

Why is your first response to say "No" to someone asking for help?

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RickyMEME@reddit

You owe him. Keep helping him.

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lolligaggins@reddit

Personally I’d just do it, but the way I’d handle this if it was being abused is help out a few times and then toss in a “joke” saying “man, I’m gonna have to start charging you for these tech support calls!” Gauge the reaction, go from there.

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mothertrucker2017@reddit

You are his “IT guy” for life.

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bastardoperator@reddit

Bite the bullet, this person trusts you and is good for your wallet. If anything, treat them as friend and see where it takes you, I can only image the clout points you must be earning knowing the main head calls you when he has a problem.

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Quick_Comparison3516@reddit

Yes you absolutely bite the bullet and continue helping him. Life's not about what you know, but who you know. He sounds like a great guy to know.

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chrome-exe@reddit

For everything he has done for you these seem like minor requests. Think about everything that you have in your life right now, that you can attribute to him in some way. Did the raises get you a place to live? Or did they provide a better place or more stability in your life. Did him being so accommodating reduce the stress at the workplace? Did those bonuses buy you anything good? A trip, gifts for loved ones for Christmas or something? It seems like this guy has given you a lot and at the first request to return a favor you say no? But you didnt say no to the raises or promotion. If this post is true, you are a user and very selfish. Bite the bullet? Man for this guy you should be taking the bullet.

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oh_no_its_the_cups@reddit

5 figure bonuses would be all I need to do IT help for somebody forever lol congrats, this guy sounds like a great guy to keep in your life.

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cmoked@reddit

One day, you're gonna need a favor from the guy, and he's not going to hesitate.

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RagingMassif@reddit

He's also probably the majority shareholder. Of course you help him with everything, until youre told not to.

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SonilaZ@reddit

He’s the guy you want to continue helping out!!

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NoPlaceForTheDead@reddit

dude, just help your friend do his stuff.

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Particular_Set_5698@reddit

it's like stowing money away for the long run.

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Golbeza@reddit

You sound like an ungrateful little shit. I hope someone at your company sees this.

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Master-Potential-364@reddit

Do not burn the bridge. It is worth the effort - you simply don't know what the long term payback will be.

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PeachLower5901@reddit

you should help him. he probably considers you a friend. if he was my old CEO, I would help him out.

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birdieinanest@reddit

i WISH i had this "problem" bro what the hell

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goldaar@reddit

If his names on the building, he’s probably still on the board, so I’d just be nice and do what you can.

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655e228th@reddit

Bet you he’s on the Board of directors. So yes, kiss up

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GraniteGeekNH@reddit

The way you describe it, I think if you stop you'll feel so bad about it that you'll wish you hadn't stopped.

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Impressive-Bit-4496@reddit

how often do we use internal guilt abt what we imagine we owe someone to dictate how well we treat our own selves, i wonder?

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lastfreerangekid@reddit

I would keep it going. Maybe even find something he can help you with, as a kind of exchange.

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nighthawkndemontron@reddit

I would do it for the networking component. He most likely still has strong relationships with the rest of the c-suite and senior leaders. You absolutely want to continue that relationship in a shitty job market.

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pdxgod@reddit

Tell him to put in a trouble ticket

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realmozzarella22@reddit

I have had some bad bosses in the past. I wouldn’t have a problem helping a good one.

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Fantastic_Fan6895@reddit

This relationship will only continue to benefit you. Nurture it!

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Suspicious_Steak_696@reddit

I’d be helping him. Good people help good people

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Heisenberg-63@reddit

Bro, you think someone with a status like that would struggle to find someone other than you to help him out with basic tech support? I'd say it's an opportunity to keep nurturing a useful relationship with minimal effort. Use it well or someone else will.

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BeanBagKing@reddit

I'll play devils advocate on this one. I don't think it's fair to keep asking someone to provide free support indefinitely outside of work (I'm assuming it is, and I'm assuming some of these problems have to be taken care of "on site"). Yes, he took care of your career for a long time at your company, but in return you took care of the company. That's a business arrangement. I can't promote one of my team members and then expect them to come to my house and hook up my modem, however nice it was of me and thankful they are. Now, I said it's not fair, but not that you shouldn't do it. Personally I wouldn't mind the occasional call because it does sound like he went above and beyond (e.g. Christmas bonuses). While he shouldn't -expect- me to do him favors for that, I'm also not the type of person that's going to ignore someone that takes care of me. Nor would I pass up the network opportunities. However, 8(+?) times in 2 months is going a bit overboard. If this is during work hours, I wouldn't have a problem (companies dime). If it's during personal, it might be a good idea to take him aside and let him know how thankful you are, and how you'll always be there to help, but maybe you can set aside time once a month (every 2 weeks? every week?) to drop by and have a beer (if he's that kind of a person, someone mentioned retirement can be lonely) and fix everything that's come up at once. A scheduled event is much easier to plan for than unscheduled calls. If he digs or needs and excuse let him know it's eating into family time, but if you can plan ahead that isn't an issue. It's not about the money or even the amount of time, but the intangible things in life that you might miss (walks with the kids, or whatever you case may be).

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damnrith@reddit

Some of you are thinking like typical IT behind a cube people. 1) OP, does he ask how your doing? how the family is? things that shows he cares about you and not just as a IT ticket 2) He's retired not dead, who do you think he's playing golf with? having lunch with? other well connected CEO/CTO's. My old semi owner has retired and pretty much almost fully cashed out of the company but I still support him. Why because that man is a people person and his network of connections if vast. If I called him and said I'm looking for a so and so person to help me with, within 2 days I'll have some C level person or owner of a company texting or emailing me asking how they can help

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moffetts9001@reddit

Exactly. Crusty, socially inept IT workers are only holding themselves back by poo-pooing a relationship like this.

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r0ndr4s@reddit

Not a single one of you has a better job because you went out to help a c-level guy at his home. I had 0 relationship with my CTO (i''m a "socially inept IT") and he still recomended me for another job. I had one coworker that thinks like you, he was hanging out with the c-levels all day, doing most of their tickets,they had his personal number,etc And its true, he built a relationship with them. You want to know where he is now? He's fired and working as a secretary boy in a laboratory because he doesnt have any kind of IT studies outside of your basic level 1 support stuff. Him wasting time sucking the C-levels dick was worth nothing. When he was fired they did try to undo it, until the actual boss hoped on a call with them and told them the contract would be inmediately terminated with them if they kept medling into our affairs. End of the call, and he was fully fired afterwards. His idea was to be in that position forever, become the on-site manager and do nothing until retirement. Again, now he is fired, his other buddy that was the on-site manager was also fired, and you know who is the manager now... oh wait, the social inept IT guy writing this that has 0 contact with the C-levels. Weird... its like your logic makes no fuckin sense.

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moffetts9001@reddit

He got fired because he thought that schmoozing with the CTO was a replacement for being an effective employee. That is not what is happening with the OP. Clearly OP has a lot of respect for the former boss, and as long as that work is not overly burdensome, then I don't see the issue in helping him out.

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Wastedplaytime@reddit

Was he your employer or your friend? What is he now? Don't feel indebted for receiving a paycheck as he got his off yours already. You owe him nothing than what you already gave him.

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bodhasattva@reddit

Get him setup on EVERYTHING, there will come a point he cant possibly need more help & youll have a valuable friend

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Curious_Matter_3358@reddit

Never close a door that you might need to go through someday

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MrExCEO@reddit

I mean do it if u can and have the time. It’s actually more interesting listening to folks like him than others. Just set boundaries, anything coming from him is no longer a sev1 😂. He could probably help u more down the road and ur kids.

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WesternExotic8802@reddit

Why does this bother you? Does ten minutes of helping him takeaway that much from your doomscrolling?

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Impressive-Bit-4496@reddit

You can always and absolutely set boundaries with him, and you can even choose to just say no if you like. Chatgpt is a good resource for helping draft a kind but firm response, or a few different responses that you can use and edit to suit your own purposes. Based on your description of him, it doesn't sound like he would be petty if you did choose to set a boundary, which, if true, is great! But also, if he was petty or something, it'd be even more necessary for you to have a boundary anyway. Bottomline is, it's uncomfortable setting boundaries, especially when you've spent a lot of life being customer service-y. Its helpful to note that just in general, you can't completely avoid discomfort when it comes to having/maintaining healthy relationships with others. You do have to communicate things that could result in one or both of you having upset feelings, and just having upset feelings is a normal human emotion that is sometimes just a situational thing and not the result of someone trying to harm someone else. Someone pointed out once that when it comes to setting boundaries, that you are ultimately choosing WHICH discomfort feels more acceptable to you. Is it the discomfort of setting a boundary and possibly upsetting someone by doing so... even tho doing establishes parameters of engagement that you know work better for you and your time/capacity? Or is it the discomfort of doing nothing, but suffering in silence and ignoring your own needs while you continue to give your time, mental capacity, and energy to someone who is a grown up, and thus likely capable enough to figure out other ways or means to help themselves when you are not around or available? In some instances, it might be better to say nothing. But in my personal experience, not setting boundaries can lead to burnout and illness, and once that happens, the boundary gets set by your own nervous system.

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yellowbeard2015@reddit

My advice: install TeamViewer on everything and give him help remotely. It's been a lifesaver - well, not a life, but a time and sanity saver - for me in similar situations.

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Direct-Ad2561@reddit

Don’t bite the hands which feed you. Seems like this guy has vouched for you and helped you grow in this career. Just because he left doesn’t mean you should turn your back on him when he’s done a lot for you. If you ever need a reference you can still call on him. If you want to advance further in your career you can still utilize him as a resource. Don’t throw this partnership away in the name of “that’s not my job.”

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Cali_Keto_Dad@reddit

Definitely NOT a bridge you want to burn. Take another look at the list of things he enabled you to get. Then look at what he’s asking for help with. He trusts you. Take this man’s call at any hour of the day.

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Handbag_Lady@reddit

Ah, these are the golden gems and I would do all I could to keep helping and making sure their things are all updated.

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Frosty_Grass_660@reddit

Give back

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marmaduke-treblecock@reddit

He didn’t get to be CEO without knowing how the game is played. So this is a relationship worth nurturing, and certainly worth keeping. What’s likely simple for you (sys admin) is probably difficult for him, and it’s something he silently recognizes. Keeping this relationship alive is worth the potential for future career dividends.

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Technical_Proof7150@reddit

Definitely just help him out

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DependentOnIt@reddit

Yep this post is engagement bait Hm guys should I go hang out with my CEO? He's kinda a bro but idk why he's calling me teehee

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Rabbit-Hole-Quest@reddit

The dude could just be on the spectrum and not sure how to genuinely handle this situation.

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throwaway098764567@reddit

gotta be, op ain't replied to anything

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Relative-Chain73@reddit

It is unclear from the post that how much urgency is being requested from OP (i have not read all the comments). If i were you everytime the CEO asks for some help, you're expected to drop everything and do that, that'd be a boundary crossed for me. If i could " get to that in a couple of hrs because I'm busy with sth else", that'd be fine for me, like as friends. If the request is sth that'll take a lot of my time, I'd say that clearly "hmm, that'd take around xx hrs for me, okay if i do it on the weekend" etc. If the request is like how to reset a password ( which i assume isn't), then like no problem

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rico_of_borg@reddit

I’m so what in the same position. It’s a no brainer bro. Help your friend out and keep the door open. He seems like someone who isn’t going to abuse your free time. All jobs are about connections unfortunately.

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fonduelovertx@reddit

If his name in on the building, do it. Success in your career is often not about the quality of your work, it's about the connections you make along the way.

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shimy007@reddit

he helped you so you help him!!!!! its easy - but just say no SOMETIMES

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fore___@reddit

Don’t set boundaries. In fact, tell him you’re happy to help and that he should reach out with absolutely any tech questions. He may be retired, but it’s unlikely he’s actually stepping away from work. He will be on a board somewhere, and he’s gonna have you front of mind every time an opportunity comes up.

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PurpleAnalysis5581@reddit

Hell him. Accept it.

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NecroGi@reddit

You're not their butler or child, you're an IT professional. You DO NOT HAVE TO REPLY. You feel indebted to them because you most likely WANT to help people, but you're not. You don't owe them anything, you're paid to do a job, you're good at your job and since they retired they're abusing that feeling to get free professional services. Just stop replying or send it to junk mail or setup an auto reply for just them. People try to do this shit all the time throughout my career and as soon as you can recognize that they're just trying to take advantage of you being useful and good at your job, the easier it becomes to just ignore it. But seriously, who cares whose name is on the building or if they signed your checks. You get paid to do the job and you did it, that doesn't mean you're an indentured servant. Have they paid you at all for your services? Have they sent you any gift cards or have they just said thanks until the next thing they have issues with?

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flexibu@reddit

I hope I never work with you lol

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NecroGi@reddit

People are more than able to disagree, I don't think this says anything about me or my work ethic, lol. I treat everyone as nice and to the best of my abilities, I've just had a lot of people throughout my career treat me pretty terrible and then as soon as they leave or retire instantly expect me to continue to assist them. I'm just giving advice (whether people agree or decide to take it is another thing) based off my personal experience, and while I still help friends I've made along the way I've just been burned too many times by those who act/expect the same level of support as on the job.

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flexibu@reddit

That’s fair, I didn’t mean to sound like an ass. The way OP wrote about his boss makes it seem like it’s a great person to work with so in my mind, it’s automatic to help for free. What takes us 5 minutes could take them 5 hours. But your point is fair too.

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NecroGi@reddit

Oh you're good! I deleted my original comment because I went back and read more details added about their boss and treating their employees good and then came to the same conclusion as others in the post.

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JimJimmery@reddit

This is terrible advice. Some relationships are worth more than money. He had your back in the past and still has major pull over the company you work at and he owns, at least in part. Corporate careers advance more based on who you know than what you know. Plus, it feels good to be able to help people.

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NecroGi@reddit

I agree (for the most part), I'm actually going to delete my original comment because learning more about it seems like the CEO was actually really good to their employees which definitely warrants the additional support. While I agree that some relationships are worth more than the money, I guess I'm just about jaded from a lot of people taking that additional kindness for granted.

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spezisagiantdouche@reddit

I've always helped those who helped me. Don't be selfish.

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garbles0808@reddit

It's not selfish to wonder if your time is being taken advantage of, even if accidentally - it's okay to ask for advice.

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B0797S458W@reddit

If the OP had previously had nothing from the guy this would be a valid point. But it isn’t a valid point.

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r0ndr4s@reddit

But OP didnt have anything from the guy. The guy he wants to help all day, was just doing his job. You're all claiming the guy was helping him, but its literally his freakin job to give him a raise for his work and treat him as a human... You all have/had so much toxic workplaces that you think someone doing their job is them doing you a favor...

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B0797S458W@reddit

You’re just as bad as the OP and you sound just as selfish too.

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sporadicjesus@reddit

100% yes, this guy changed your life.

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MyKettleIsNotBlack@reddit

You don't have to think about this emotionally. In quantifiable terms (hours of your life back or money most obviously), has what he provided to you greater than or equal to what you have provided in return? Minus anything you did while officially working and he was still the boss, only consider the 'favors' or favoritism on both sides. Doesn't sound like a bad thing, and you never know when a successful retiree is going to refer you or start a new business when they get bored (and it'd be nice to be the first thought when it comes to IT/tech roles). I find most adults, even the wildly successful ones, can feel lost when it comes to technology and it goes a long way to be helpful under any circumstances.

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yaboicassrocks@reddit

You can look at this practically or emotionally. Practically, the man has your back. Having his back is only gonna deepen his support for you. Emotionally? The man’s been through a lot with you and trusts you. It sounds like you’re someone he enjoys being around, so you can be around him if that’s a boundary you’re ok with.

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didact@reddit

Retired doesn't mean he's got no interest in the company. You mention he's friends with other executives, but in fact he's probably an active owner - likely serving in a board of director capacity even if you don't see all the evidence. So yes, keep helping him. Buy him whiskey, get to know the guy. Network... See if he sits on boards, who his contacts are. Ask him for a mentorship - tell him you want to connect business and technolgy, that's always a winner. What I'm saying is, put the effort in and squeeze him for a little bit.

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spootieho@reddit

I've been in this boat. I would help at $50 per hour, which was a good discounted rate considering if he got help elsewhere it would have been at least $100 per hour. Also he trusted me way more to do the job right than the $100/hr people. I would also normally charge $100+/hr for such services to any clients. At the $50/hr rate it likely limited his requests, while keeping good terms with him. Eventually the requests slowed down and died off, after a few years. Until I never heard from him. One day I wondered about him, and so I ran a search on him to see what he was doing lately and found out he passed away (which explains why I lost contact with him)

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kr44ng@reddit

Past benefits from this relationship shouldn’t mean much if anything at all; the question to ask yourself is what do you gain and what do you lose from continuing to be nice to a potential relationship asset, eg networking, referrals, inclusion in his estate planning, etc vs your pro bono time.

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strifer_43@reddit

I became my bosses tech guy, he’s helped me a lot , when I needed a promotion or raise he would back me, invited me to his family cabinet and other places . He’s 72 and doesn’t like tech or good with it so I help him out , he’s a mentor and a friend so I sometimes do get frustrated with having to help especially since it seems easy to me but then I remember how much he’s helped me out and when I needed help I would call him on stuff I don’t know and to him it was probably the same I see him with tech . Sooo long story short I say help him out if he’s helped you out so much , he’s basically a friend.

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SikhGamer@reddit

This makes me sad. Dude does/did a lot for you. I think he see's you as a friend. You clearly don't see him as a friend. How awful for him.

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CantaloupeMaximum660@reddit

You don't even need to look at it like biting the bullet. You're being of service to someone who you know is a good person and who has your back. Those people are rare. You keep being of service to him and you'll likely be rewarded ten fold in some way.

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LexHokata@reddit

Best bet is to teach them how to do those tech tasks. If it's easy stuff then it doesn't hurt to help.

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freebiscuit2002@reddit

It sounds to me like you could decide to be kind and help the guy out. It's not like he's never helped you, is it - so why decide to be a dick about it now? Plus, he's still friends with all the other execs, so I would argue it is in your interest to keep him on your side, even in retirement.

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Business_Nothing5722@reddit

Just help the man unless he's calling you multiple times everyday

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Real_Entertainment46@reddit

You could always lend a help but if you want to not spend so much time on it you could try sending him tutorial videos too which you think would be most helpful for. Of course the basics should already be instilled with your former boss maybe also seek help from their family members if you know one.

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Sufficient_Fan3660@reddit

Why would you say no? You get paid the same no matter the work you are doing. Until someone above you tells you to not help him, then you help him.

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njrnow7859@reddit

Wow, so, grateful much?

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ccwilson84@reddit

I'm helping him if I was you. He sounds like he helped you more and there would be fallout if you don't.

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RedditClout@reddit

This is a case by case basis. Anyone in tech knows this feeling and knows how to act appropriately. You already know the answer regardless of what your professional organization has to say within the boundaries of Security protocols and the like.   IE - I've helped previous employees, executes and such in the passed and I've also had to tell some others I simply don't have the time. The benefit of being in this trade is that you can easily build networks (no pun intended) if you want. Any decent person is worth helping and they're generally pretty grateful for your service in return. Its kind-of an overlooked part of this field.   Sounds to me like this is one of those cases where having this network in your pocket is worth keeping. Doesn't seem to invasive and there is certainly mutual respect across both parties (gave good raises, so on).

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angelliu@reddit

I was in your position when my former boss sold the company. I did step back doing many of the things I used to do and for the most part, he’s respectful of my time. I have helped him on the occasions he’s asked and after his retirement, usually have dinner with him and another boss 2 to 3x a year. Considering we spend so much of our working lives with bosses and colleagues, I think it’s good to maintain the relationships that are worthy (and he sounds like one). We all genuinely like each other and have great conversations. After the pandemic when I was looking for a new job, they both made sure to refer me to someone and while that didn’t pan out, you never know what will. I never asked them to do that, they just wanted to help. Given how this guy has been solid for you, if I were you I’d usher this into a more personal relationship. He seems like an ok person to have around.

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Black_Magic_M-66@reddit

OP Make up excuses but try and get to his needs maybe once a month. You'll want to maintain that relationship to some degree.

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1917he@reddit

OP you seem completely lost. The way you describe this guy is like a friend but all you've done is describe basic management responsibilities. You've fallen in love with your manager and now you're doing free work for him. You need to understand that paying bonuses and having a business doesn't mean you owe him anything. It's honestly cringe to read someone this head over heals for a guy that hasn't done anything. You're seriously thanking him for starting a business that you worked for simply because you got to make money. Why are you working as his bitch? Is he a friend or are you just incapable of thinking for yourself and being your own man? Your love letter tells me it's the later so you should just prep your asshole for him and get ready for others to do the same since you have no boundaries.

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Professional_Fox_749@reddit

Look at this differently. In lieu of the tedium you currently see you must acknowledge the unique opportunity it is to be closely engaged with the founder: tremendous experience that can help you, closeness with execs that can help you, industry connections that can help you. It’s definitely not a burden, it’s a gift. - from a needy but appreciative founder/ceo myself

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willzyx01@reddit

Being so close to a CEO of most companies will give you better connections than any LinkedIn ever will. I’d be a free on-call support for someone like that.

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Raa03842@reddit

Yea. If he treated you that well you need to reciprocate as long as it’s needed. Lark is not something you want to mess with

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FearlessVegetable30@reddit

\>The business he built helped put a new truck in my driveway and food on my family's table for 5 years. \>He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. \>He's signed his name to hefty bonus checks every Christmas (some 5 figures). and you cant help him 1 time a week with a computer? after hes been gone for two months? you sound pretty selfish

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Hendo52@reddit

Eat this cost. Hope it’s in your selfish interests and if it’s not, you could accidentally do a new nice thing.

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BeenisHat@reddit

If there's one thing that LOTS of us IT trolls lose sight of in our data center dungeons, it's that personal connections can be very useful in advancing our careers. Networking opens doors, and not just the OSI model. If the old CEO is still calling, help the guy out. You can probably add him to the RMM setup you already have and address a bunch of his issues without leaving your desk. But don't forget to stop by for a long lunch from time to time. Older guys, especially boomers, appreciate the face to face and handshake approach.

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Dr_Solfeggio@reddit

Based on how you describe the job and what this opportunity has done for you and your family, it's sad that this is even a question. Where's your gratitude and loyalty? I know you worked for it, and it's not like your paycheck was charity, but come one dude... be a friend. But let's go totally capitalist on it... What if, 5 years ago, you were told... here's the job, here are your hefty bonus checks, plus tech support for our CEO once a week into his retirement? Would you turn it down? I doubt it.

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ImTalking2U2@reddit

You're sitting on a gold mine dude. Listen to everyone here and take their advice. Sounds like someone you always want to keep in touch with.

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LAMarie2020@reddit

Bite the bullet as you said. There are worse things.

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Specialist_Low1861@reddit

I have people like this in my life, including my parents. I help them, but I also leave them written instructions on how to fix the same issue in the future, ensure that I clearly communicate sustainable habits that will prevent their issues in the future (replacing complex AVR sound system with a sound bar, telling them to use a password manager etc.) such that they feel empowered to start fixing things themselves and perhaps a little embarrassed to call me since I set them up so well for success. I also strategically will ignore their calls and get back to them in 24-48 hours sometimes. Recent case of this was them asking for help with their sound system for the 4th time, at 7pm at night, while drinkjng with friends, after I had already told them to replace the "complicated" AVR with a soundbar. The result was them messaging me 48 hours later saying they were ready to make the switch to a soundbar. I helped them install it and now I'll never have to help with that again. Yes it's annoying at times, but they have done so much for me, and do more for me because of what I do for them. It's worth it. This guy sounds like someone in your corner, who has helped you make your entire life what it is. I'd keep helping him, with strategic boundaries.

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Duggerdean@reddit

Founded the company and still wants to talk with you. You’d be a fool to not assist if you have any plans to stay there’s He’s retired now and likely misses the grind. Throw him a bone.

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RedundantPundant@reddit

Even retired, he wields power and control. You should consider this networking. All of the executives respect and communicate with the CEO. So him knowing and counting on you means your name will be mentioned to all of them. Learn all you can from him, pick his brain. Your career will be that much better for it.

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henryguy@reddit

Also maybe he wants to spend time with you and this is the only way he knows how. Retirement gets lonely fast, even with a family.

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SaltyElephants@reddit

Used to be an EA, and one of my old CEOs retired and he occasionally texts me pictures of his pets lmao. He hasn't done it in years now, and I heard he's started carpooling his former employees to their jobs and back each day. Basically a free taxi, haha. He is definitely bored.

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mcon96@reddit

Well OP isn’t this guy’s therapist, so I’m not sure why that matters

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perthguppy@reddit

Successful, retired, entrepreneurs are some amazing people to maintain connections with. They get bored, and have a fucktonne of money. It may be they have an idea for another company to start and they want you to “set it up the right way” or they may want “the best home wifi you can get” which means spending $20k. I once knew a retired broker who dropped $100k on a netapp san for his house because he wanted something fast, reliable, with 24/7 support to store his photos on. Another retired finance exec who only used his laptop for internet and email, but had a standing order to always have the best Microsoft Surface device available at any point in time, which meant he got a new laptop once or twice a year, once he got some dirt under a key so changed it to having 2 of the laptops at any point so he always had a spare.

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QuarantinedBean115@reddit

exactly. blows my mind OP somehow clearly has the smarts to get to where he is, but is for whatever reason completely misunderstanding this friendship that could continue to benefit him and his family. and again on a human level, he acknowledged this boss did a lot for him, as another IT worker i get the help can be mundane, but this is a scenario im sure most people would do it with a smile knowing what he’s given to him in return. I certainly would be so happy to gladly provide that support if my boss made my families life better.

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possumcounty@reddit

He’s reading the situation as an employee rather than a human. Which makes sense given the world we’re in, people don’t want to work for free for someone who is no longer their employer… except OP’s missing the mark. I don’t think he’s realised he’s made a friend, lol. He seems nice, and you (and other commenters) are right that he’s an excellent connection to have.

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Crunchwich@reddit

This mentality is the difference between entrepreneurs and employees. Employees are taught that their time is worth $x.xx /hour and they act accordingly. Entrepreneurs understand that their time is a valuable asset and it can be invested into something without an immediate ROI. I regularly give free consultations, attend social events with the intent to network, and even offer my (normally expensive) services to friends that I know have the ear of a community I am trying to break into. If I was only taking on engagements that paid upfront, I would miss out on some incredible business opportunities.

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OnTheEveOfWar@reddit

That’s what I was thinking. Sound like he thinks OP as a friend. Nothing wrong with helping someone out who helped OP with his career. He also might gift him some money at a point. A retired CEO probably has some cash lying around.

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Ok-Strength-5297@reddit

maybe he wants to give OP 50% of his networth? Maybe he's interested in taking the relationship further? You never know, could be so many things. Definitely not abusing his status to continue to get tech support for basic shit.

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msavage960@reddit

This is also a great point. My father is retired and we have to push him to get out and about, though he does have two shihtzus at home who’re basically his “new” kids lol

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AlarmFamiliar385@reddit

Yeah man. I think you need to change how you view this - how many people in the company would kill for this opportunity to have a direct connection to one of the most powerful people in the company. This is networking. Brown-nosing is part of the game.

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entropic@reddit

Important distinction: Are you doing this on the clock? Or in your free time? Because it may be possible that your employer is perfectly happy to let you continue doing personal tech support for their founder/ex-president/ex-founder. We have former executives/board members/other "VIP"s that my leadership is happy to have us help as part of our work time...

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ChestOther@reddit

Im a tile contractor and this sounds like my first client. He's an older retired guy, and I did 3-4 jobs for him over a couple year span, and we became somewhat like friends in that time. He calls me every once in a while for help with random things because he has a bad back, no family in the area, and nobody else to call. He's called and asked for help with a variety of things like moving furniture, unloading a hot tub in his driveway, and even being a witness to a will signing lol. When I did projects for him he never batted an eye at me for pricing, he just wrote the check. Him and his wife would constantly do nice things as well, like give me thc edibles, and gourmet dog treats to take home, and even invited my ex and I over for Thanksgiving one year. Overall he is always very pleasent to be around, and I enjoy the friendship we have, so I'd like to keep him around. I dont mind doing those things.

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anjoradioativo@reddit

Become his personal friend.

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AnEyeElation@reddit

Just because he’s not part of your company any more doesn’t mean that keeping that connection may not lead to future professional stuff. Like what if one of his business contacts asks him for a reference to hire someone into a big job somewhere? If he always treated you well I’d personally help him out.

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castlite@reddit

You help him out. You have a good life. Don’t make an enemy of him.

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r2d3x9@reddit

Keep helping him

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sho21na@reddit

Depends if you are a nice guy or not

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jiggly_bitz@reddit

By the way you painted this story and your relationship/interaction with this person, I feel you would be foolish to squander the opportunity continuing a relationship with this individual. Sounds like you have a positive experience with this individual. Helping them out occasionally isn't the worst thing considering they're successful, likely connected (at minimum within your company), and sound like a decent person. If "helping out occasionally" is the worst thing you'll have to do as "biting the bullet", then you'll probably be ok.

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MrHodgeToo@reddit

He’s taken very good care of you and while he has retired as your official boss he still maintains an amount of potential influence over your job due to his ongoing connections. I’d say consider these good deeds an investment in your own professional network.

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_TakeMyUpvote_@reddit

tell them you'll continue the tech help relationship on one condition: lunch once a month. could be anywhere, mcdonald's, doesn't matter. the point is for the two of you to spend a little time together, trade stories, maybe ask each other questions. and for that, you'll still continue to be "on-call" for their help. They will continue to give you _their_ time by meeting you for lunch, the relationship will feel real, and they'll continue to get their tech help from you. it does sound like this is an actual friendship, albeit a 'work' one. and often the CEO types think of people who do this type of tech work as 'The Guy" like 'i got a guy for that', they seek out specialists and place high value in them. take that for what it's worth, i don't know much about your situation. if any of it feels not right, by all means, you're not required to help this person anymore. don't feel obligated!

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Mundane-Nothing-3294@reddit

It shouldn’t cost to be kind, good deeds will always be seen.

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Professional_Fox_749@reddit

Bite the bullet

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_stream_line_@reddit

Is it really that much effort for you? Genuine question. From what you wrote and sounds like he did a lot for you.

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TheFIREnanceGuy@reddit

Ask him for a consulting fee. You already work a full time hours so jts unfair

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Sucramfatsgaw@reddit

Do it to be nice to someone who has helped you grow, not because you want something in return.

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Significant-River684@reddit

I would help. My old ceo used to have me help him. And when I needed a reference I would give his personal phone number out. That recommendation is worth it's weight in gold.

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Rostrow416@reddit

Sounds like that’s a bridge you don’t want to burn. He treated you well, and if his requests aren’t outlandish or inconvenient, it would be a nice way to keep him as a resource or just a friend for the long haul.

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FloatIntoTheFinite@reddit

One call a week is not that much man. Just treat him like a friend

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Rexpower@reddit

If he was good to you at work, more than likely he will be good to your outside of work. I did something similar with an old boss who retired. I think it took him a hot minute to realize what he was doing and he started giving me cash or souvenirs from his vacations (like actual good ones)

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Which_Ear_2399@reddit

Why are you even asking this question?

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darksquallz@reddit

Connections like this are priceless. You never know when you will need to call in that favor.

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AdagioBig5474@reddit

A man that has mentored me for most of my career has told me that sometimes people give you a rope to see if you pull it. If you do, they keep giving you opportunities, if you don't, they stop relying on you. What I mean is: while not everyone is testing each other all the time, he's given you plenty of opportunity so far. You should give back, because you never know how many other opportunities will come. Maybe set boundaries, like others said, by asking for non-monetary giving back, like an occasional lunch. I'd love to have someone like that myself, someone that trusts me, still has career-influence and can lookout for you. Someone who can even mentor you if you treat your connection nicely.

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morningisbad@reddit

Might not be a bad idea to ask for a written recommendation. "I'm obviously not looking right now, but I wanted to see if I could get a recommendation from you for any future opportunities". I've got one from years ago that I still include.

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TrickyResort7033@reddit

I truthfully don't understand why you would. Even if you get nothing out of it, you arr extending a kindness.

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_Junx_@reddit

dude changed your life and you want to complain about a once a week call? yikes

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CharacterActor@reddit

Cut him off, and the next day he’ll be speaking to the companies currency CEO about who can help him with his Tech Support. Because you won’t anymore. He may not even volunteer your name. But the current CEO is gonna ask questions that lead to your name being given up. Think of those five figure bonuses this guy handed out so many of to you as his cashing in future tech support now. There’s no upside to you stopping. There’s a job and life-saving downside if you do cut them off

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Ob1wanatoki@reddit

Tell him you've awarded him X number of weeks/months or whatever your comfortable with of free tech support but after you'll need to charge your usual rate of $X per hour for support in the future.

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gooeymac_fl@reddit

You never know how his connections can benefit you someday. Be a good human and help him out

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Low_Break_1547@reddit

My CEO was just forced out. If he called me and asked to help with anything, not work related, I'd be there ASAP. He always treated me and other employees with respect. He went out of his way to ask about my wife when she was seriously sick in the hospital, and I think actually made some calls and pulled some strings to help get her into our preferred rehab. I would be there and want nothing in return.

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DirkDeadeye@reddit

I mean, if he wanted to have me pinch hit while he hides in the closet wearing a superhero costume I think I’d do it for him given the love and dollars he’s personally provided. IT help? That’s not asking much.

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FacelessCougar69@reddit

Ask him to help you move

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r0ndr4s@reddit

I swear some of you here have no life at all and its all about networking, jobs,etc He's not a friend, he's literally refused to learn any kind of tech for decades and is now using you, because he knows you will answer, to solve all his issues that he can literally pay for or like I said, he could've have learned by now. People here are suggesting that you should totally help him, not even just for him but because he's still in contact with the higher-ups... wich means what? extorsion? If you dont help him, he's gonna ruin your career? When you just keep helping someone again and again, they will keep calling you and they own you basically. I had a professor that went trough the same shit, his family, friends,coworkers,etc all asked for IT support, for everything, until he basically said to them that if they wanted help they needed to pay a fee for his work. They all stopped asking basically, and not a single relationship was broken. Learn work-life balance people. And being someones IT support 24/7 because he did his job as CTO, isn't balance.

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Aggravating_Tale1368@reddit

Suck it up.. but of course ensure it works on your time. Also do not hesitate to ask for advice or ask for more recommendations for more side work in his inner circle of friends. Ask about the corporate structure and how can you move up the ladder. He will either give you want you need or will no longer call you.. my team has always supported the C suite teams at home but they were always taken care of.. $$

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creative_usr_name@reddit

Can you try to do most of your help when "on the clock"?

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h2vhacker@reddit

If you need the extra cash don't cut ties. A ex CEO can be a client. Cuz if times get hard I'm not saying they will at least he is one other source of income.

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Open_Entrepreneur_58@reddit

My question is...why wouldn't you? If the dude has been as good to you as you say he has, why in the hell wouldn't you?

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rikemomo@reddit

Sounds like a great opportunity to keep in touch with someone who can be a terrific reference and potential advisor as you navigate the years ahead. I bet he really appreciates the help (and might even feel vaguely embarrassed to keep asking), but you know what you are doing so it sounds like the requests will slow down as you hook him up with working systems. If it gets too much you can always recommend a more formal solution but for the time being it seems like not too big a deal to help him — and keep the relationship positive.

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H-A-T-C-H@reddit

Just do it on company time, the new execs will understand, and if they don't then bring that up with the dude during regular conversation. I bet you'll be able to get away with a lot after that

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auntwewe@reddit

Reference for life. Help that dude out!

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Intrepid-hobbycoder@reddit

Looks like the answer is in your question. Your contributions to him seem mundane and miscellaneous compared to the life altering support and respect you got from him. In your position I would do the service with gratitude and without question. You will find contentment in selfless service.

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LionBig1760@reddit

Just do it on company time. Is he still on the board of directors for the company?

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MeasurementFormer186@reddit

Sounds like you are friends and he has helped you out immensely. You sound ungrateful. Why not help him

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throwawayorsmthn12@reddit

No bigshot ceo who has helped me in a transactional way is entitled to my personal autonomy, sorry, if you feel coerced it is because you are right.

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bucdotcom@reddit

This isnt the bridge to burn, IMO. Work out a fair rate and continue the relationship. He obviously trusts you and is comfortable enough with you to let you work on his stuff. Even after his departure, he still thinks highly enough of you to call on you.

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Salty-Assumption5392@reddit

Bite the bullet on all the questions you can answer. The assistance will taper off over time. Have a phone number of a person or company you can recommend for issues you can't solve. Call in advance to that company so they know the name of the retired executive. Don't burn the bridge for two reasons first being most important. He's been good to you and you should in turn demonstrate loyalty. Rare and unusual. Second he will likely help you somewhere along your career. A very good reference for example. Don't screw it up by telling where to go.

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CalmBeneathCastles@reddit

With all due respect; you ungrateful kneebiter! If someone gave me a *single* 5-figure bonus, they could call me in the middle of the night to come reset their router or make them a cup of warm milk, let alone *multiple* bonuses. All you have to do is *occasionally* walk them through it from wherever you are. For shame!!

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Minimum-Function1312@reddit

Yes help him. It’s also his way of staying in touch with you and what’s going on with the business, let him enjoy it.

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x534n@reddit

I'm in a similar situation but it's possible the old CEO has some arrangement with the new one and as he was good to me for so long, I help him regardless when he needs it. He is still close to the new CEO, so you probably don't want to piss him off if yours is as well.

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SFmodscensorship@reddit

you are crazy. he did so much for you. Jesus

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AvogadroAvocado@reddit

Im sure a retired CEO like him can afford to pay you a small consulting fee to have on call. Alternatively have you tried making friends with the guy? Sounds like the kind of guy who’d be happy to pay you back in kind with dinner or something such as that.

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UJ_Reddit@reddit

Be a friend and ask him for a beer, see how it plays out

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bwoah07_gp2@reddit

"If you're gonna keep asking me to troubleshoot, you should pay me." If he's rich enough, see where that takes you 😉

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AgreeableSale8505@reddit

This person did so much for you. It’s the least you can do.

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secretsecretson@reddit

Most modern phones offer choices to what you want to answer. Personally I often use the silent mode (Iphone) which makes it sound busy for callers and tells texters I've turned off notifs. And sometimes I "forget" I turned that on (it doesn't affect your alarm). Everyone knows everyone is lying, but if they can't prove it they're just gonna have to live with you having your own time. But, if this guy was that good to you I would consider trying to be good back. WIth boundaries, but don't be cheap if an elderly person that helped you needs you now. That's bad form and kinda self serving/egotistical/other choice words. If you don't burn him I think your bridges will be ok.

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OkEstimate8596@reddit

I mean, what's the question? This guy was so awesome to you, if he needs tech help once in a blue moon, help the guy out. He also 100% still has pull at the company, other than just being a friend to someone that clearly was a friend to you it is just a good career move to remain friends if your cynical about it.

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kyle46@reddit

My rules for everyone who I would call a friend is simple, make sure there's food and beverage, the works never guaranteed, and this is a time for us to hang out where we get something done but the hang comes first. To me, it doesn't matter if we need to build a shed, repair a fence, clean-out a garage or someone needs tech support.

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popanonymous@reddit

Answering random questions or consulting, easy peasy. Running cables in a 120° attic for his third home might be a stretch without some extra scratch.

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Wise-Novel-1595@reddit

Just bite the bullet. Go back and read what you wrote. The guy’s done well by you. Return the favor and don’t risk it.

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Nightenridge@reddit

This is an ally that you want to have. The menial tasks are worth the symbiotic relationship.

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Splunge-@reddit

You don’t say no. It’s both a “thank you” for all he’s done, and a potential investment in the future. He’ll talk nice about you to other CEOs, who might want to offer you something better.

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NaturalSelecty@reddit

Bite the bullet man, this guy is a connection you don’t want to lose. Sounds like he’s also earned the tech support based on the bonuses, promotions and raises.

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Cautious-Ring7063@reddit

Take the truck and the money and all the other good worker gets appropriate rewards instead of getting shafted bits out of the equation. If you count him a friend, be a friend. Would you invite him to the movies or lunch? Would he/has he done similar? The urge to Elevate people to kings in the hope to ride their coattails is very clearly real and has lots of logic behind it, but is so damn toxic to everyone in that relationship on the long term. Any ex-CEO is now a private citizen and has the money to buy his own tech support.

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KnowledgeSiphon916@reddit

Should be a no brainer

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FitMatch7966@reddit

Unless you are about to retire yourself, I would keep this guy happy. He could get you your next job and the one after. Also, he could keep you from getting them. Suck it up

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Practical_Gas9193@reddit

Help when you can and are up for it. Don’t when you’re not.

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KUUUUUUUUUUUUUUUUUUZ@reddit

just bite the fucking bullet my guy. thats someone you want in our corner for life. Doubt helping him occasionally with ipad troubles is worth even the chance of burning the bridge, no matter how low it is

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noddin_off@reddit

Charge it to the game. Nothing he has can be that time consuming and consider it an investment in your and your families futures at the bare minimum. He may not be active daily anymore, but he's still swinging heavy in your company culture as well as the industry. Don't make it weird and it won't be weird.

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InvadedRS@reddit

Now hear me out…. Help him because without him you wouldn’t of gotten those shots to me that’s a friend for life no matter what’s happening

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younglad420@reddit

Bro you a bad friend lmao. I'm kidding but damn

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Natty-Splatties@reddit

A former CEO of a company that appreciated and valued your work is something to keep in your back pocket. Could unlock a lot of doors professionally.

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Kindly_Cockroach_810@reddit

what i would do is read your second paragraph again and then just help the guy out...

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Adorable_Cat1767@reddit

You should be his friend. Who knows what else he may have for you in the end? He helped you, so you should help him with friendship. Kindness is so hard to give for "free," yet he gave you the same with "money.

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Party_Unit_5006@reddit

I've seen plenty of horror stories on Reddit asking similar questions but with terrible CEO/boss. Let's throw your situation on the opposite end of the spectrum. (1) He's always been extremely appreciative of my work -CEO always questioned/criticized your hard work (2) business he built helped put a new truck//approved multiple large raises -stagnant wage/salary prevented you from buying a much needed car/truck (3) said "absolutely" without hesitation when I asked for a promotion -stuck in same position for past handful of years with little or no potential for upward mobility (4) He's signed his name to hefty bonus checks every Christmas (some 5 figures) -no bonuses or "slap in the face" double digit Christmas bonus I think just two out of these four things you listed about your CEO would make me feel eternally grateful to him. From what you posted, i feel like he's asking for initial help setting up his devices post-retirement. My parents also asked for a lot of help initially with their devices but only reach out once in a blue moon for help specifically with their devices. I wouldnt even call it weathering the storm but a way to show your appreciation for what sounds like a wonderful CEO who supported your career and will likely fight for you even under new management.

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hcvc@reddit

I’d just help lol

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WhyToHide@reddit

Honestly, sometimes I read posts like that and it just surprises me how some people lack basic skills such as kindness, respect, and self-awareness. My dude, he helped you; he's been kind to you; he's asking for your help - why do you even have to question this through reddit posts...

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Marcx1080@reddit

Stop being a cuck and help the guy who helped you

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TheVog@reddit

I've been and am still there. You absolutely keep doing it. Especially if he's still a part owner. If it REALLY bugs you, clear it *tactfully* with someone above you. Simple as that.

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IFuckBlackGuys@reddit

Seems worth. Put up with it and pitch that you guys should get dinner. Either he gets awkward and stops or probably buys you dinner 🤷‍♀️

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edcculus@reddit

I’d probably keep doing it. Not out of any sense of obligation really. But he seems like a great person to have in your social circle, even if it’s just menial IT tasks at the moment. I assume he’s well off in retirement. It’s quite possible little perks like “use my vacation home at the beach” might come up. Not that I’d expect that out of hand, but it never hurts to keep up good relations with people like that.

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Backstabbinghoe@reddit

Sounds like someone you should help for sure, there is no way for you to say no without burning a bridge.

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BuzzardInTheAir@reddit

fake AI story

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dutchbasterd@reddit

Ask 200 dollars per hour. Win/win.

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WillHuntingthe3rd@reddit

I would keep helping him. He may open a new door for you or may not. He did a lot for you.

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gOldMcDonald@reddit

Of course help him out. Do it as a friend. A man who built a company like that is a good friend to have

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MontyBoomslang@reddit

You know, it can be really nice to have a generous, rich friend. They don't come along that often. Try to get more chummy with the guy when he calls. Especially if it's during work time, it can't hurt in the long run.

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Chazzwell50@reddit

Sounds like he was very good to you so I see nothing wrong with helping him out and it will slow down eventually he's probably going through a bit of an identity crisis and doesn't even know it happens to a lot of people who retire after a long career

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Duel_Option@reddit

Dude has contacts and can connect you to places you don’t even realize you may need The answer is to pick up the phone and be his friend, when the time comes and you need a favor, he will remember

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wittylotus828@reddit

Does he still have a stake in the company?

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lX1Vl@reddit

1. Start a new LLc. Your vision is to teach new companies and people how to maximize online efficiency and taking the sting out of the daunting task of the coming AI world. (Front facing answer) “This is your side hustle to raise money for xYz. (Find an area of his passion; like clean water… 2. Create a menu of services that directly correlate to all his needs; set prices. 3. Send a BCC email to potential customers (namely him). Invite clients to utilize your new hustle. Include an invitation for all recipients of this new venture’s email to share with family and friends. 4. Wait for the next call… Then say, this is great bc it’s boosting his company and helping out bc 10% of all net profits go to (CEO’s Passion Cause) Then provide an estimate of time, and cost. To your ex boss, stamp the invoice with (-25% Off for Family and Friends) A) he will stop calling B) keep calling C) you make money on every pestering Entire build out is 2 hours. You can be selective and build a lucrative side hustle

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offroadadv@reddit

I would continue giving support if I were in your shoes. My retired boss was great to work for, and he promoted me several times before he retired. It was his strong recommendation that helped me to secure a CEO position in another organization when I needed to move up and out. That could be your story someday. One never knows what the future will hold.

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Tricky_Orange_4526@reddit

honestly depends on the level of CEO he is. anyone who starts a business is technically a CEO, but does he have connections. to me this seems like an opportunity to help him and get help in return advancing your career.

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L42Kong@reddit

Just a thought, as a guy, who often feels the need to find an excuse to socialise with other guys, maybe his calls for tech support are actually a call for a chat and a coffee, maybe he just wants to remain mates, which is valuable in my book

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GrandSpinale@reddit

You say you feel like you owe the guy a lot but now you don't want to help him? Brother you answered your own question.

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gusto_44@reddit

He just needs a friend. Keep him close. I guess the rate at which he's requesting things will decrease in time, this is what usually happens. Unless your friendship will go beyond occasional tech help, you get invited to dinner, fishing or what not. Good luck.

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Lena_aveline@reddit

Purée sacrée dilem... mhh en vrai je dirai fixe lui une limite de 1 fois par semaine

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Metabolical@reddit

In his book Influence, author Robert Cialdini talks about how there are favor based relationships and transactional relationships, and how they feel and the associated expectations differ in each. It sounds to me like you are experiencing the discomfort of somebody with whom you had a transactional relationship who has started treating it like a favor based relationship. My recommendation is explore whether you and he want a favor based relationship, also known as friendship. Is he using you, or is he actually up for being a bro? See if he ever wants to hang out, give you advice, help you progress your career, etc. He might not, in which case you have to decide whether you will let him use you while you hold out for the day where he will return the favor with career help, or want to cut it off. Like most people have said, seems like it might be worth it, but up to you.

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fractal_disarray@reddit

You're in a good position, don't screw this up.

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xyzszso@reddit

Others have stated already, but I can only reinforce. This is a great social connection, the guy sounds like a genuinely good guy, and one that will remember that he could count on you, and will return the favor if need be. Would I interrupt family dinner, to solve a problem? No. But I’d call him back the same evening.

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Today_i_might_wait@reddit

I’m with others here, are you missing any other cues? How many friends does CEO actually have?

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NaughtyRenoCouple@reddit

Tell you what, I'll take the burden of helping him off your hands, lemme get his contact info.

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ExcitementRelative33@reddit

Depends if you want to be typecast as only the IT go 'fer or do you aspire for something more which will never materialize. Of course if his relatives/family is still running the show, it will be tough to break away cleanly.

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No-Delay-6791@reddit

I suspect he has been used to asking and receiving help with tasks for a long time and the line between business and life blurred even longer ago. If you can help with some minor stuff, I'd do it. He's likely in a transitional period of his life and learning new things daily. The requests will probably reduce in frequency and eventually stop once he's setup into a new normal. Obviously if it's turning into a serious piece of labour, say something to him "happy to help with the little things but sorry, that's too much for me to easily fit into my schedule. Have you tried contacting *insert name of local IT firm*? "

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Notnow12123@reddit

A lot of people seem to believe that if you don’t get paid for something you do you are a fool or allowing yourself to be exploited. They don’t need the money necessarily but what the recognition that being paid, and well paid confers. If this guy who helped you believed that you wouldn’t been where you are today in your career.

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No_Union_3231@reddit

Setup a monthly lunch with him, preferably during work day or even in the office (he can bring takeout) and when he needs something just say “let me think about it and I will trouble shoot next time I see you” he may be lonely and looking for excuses to chat with you.

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jethro1999@reddit

This sounds like he’s your friend. Is there a reason you don’t feel the same?

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DevilCass@reddit

Wow I would not even think about saying anything to a guy like that who occasionally wanted my help with something. I hope you didnt say anything yet and that you can look at this from a different light, because thats someone who I would be happy to help for life with things here and there when he asks

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fcvfj@reddit

wow, is this a serieus question? according to your own words, he's given you so much and may continue to do so, and you're bitching about helping him with small simple stuff?

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Deep_Guava9414@reddit

Invest in this relationship! It will pay in long run. You owe him clearly, and he’ll keep you in mind when ideas, mentoring, opportunities come up. My husband keeps these kinds of relationships going, and before you know it, your kids are getting great opportunities. Suck it up.

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Zachisawinner@reddit

What the fuck is wrong with you people? This guy doesn't work for the company anymore. You don't get paid to help him with his personal tech shit. Fuck him. Fuck.

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funggitivitti@reddit

Kind of sad how people have become so ungrateful and selfish.

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Responsible-Bid1064@reddit

How can we expect the world to be a better place unless we help those who live in it?

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KayskolA@reddit

Reminds me of the more recent saying, "community requires inconvience." He probably wouldnt be reaching out if he didnt view you favorably/friendly. And it sounds like you have a lot of positive feelings towards him. A healthy boundary might be asking questions to encourage him to figure a problem out himself first before coming to the rescue. Might help with a repreive.

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CarltonCatalina@reddit

Yeah I'd hate to do the wealthy guy a favor by helping him with occasional support so he can type out his will..../s

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Unusual_Swan200@reddit

Sounds like he has been good to you, above and beyond. Someone who is appreciative of both you and your work is a rare gem. Why not help him out . Be good back at him. Besides , there is no need to keep score , no need to tit-for-tat. Help the guy out . Help make the world a better place. And if it gets irritating, put a smile on your face and do the right thing. Be a good guy and feel good about being helpful.

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Rude_Strawberry@reddit

What sysadmin job pays you 5 figure bonuses?

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Trawling_@reddit

100% what the guy in comments said. Charge him lunch every now and then if you otherwise get along. Make it a social thing.

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YinzerInEurope@reddit

My man. Sometimes you have to do things you don’t want to do. Especially if that person more than looked out for you previously.

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Tb1969@reddit

He’s worthy of your time. Don’t just begrudgingly help him, be motivated to help him.

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dumb__fucker@reddit

This is called a "friend". I mean, is it killing you to help the guy out? I'd run through hell with my friends if they asked me to, and I would lead them through hell if I needed to. Are you on the spectrum or not comfortable in social interactions with others?

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Tight-Bath-6817@reddit

When can I get a CEO like this? XD I do they mind helping him 5 times a week instead of once a week lol

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Confident-Variety124@reddit

You are an employee at the company he founded, YES you are his tech for life (as long as you work for that company). He may be retired, but his connections are not.

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GothamKnight1981@reddit

These kinda CEO types almost always have season tickets to spare for one sport or another.

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BeKindBabies@reddit

Worth it.

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theRealStichery@reddit

He’s scratched your back plenty. Time to scratch back.

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Ghost-Writer@reddit

I mean he maybe retired, but that doesn't mean he stopped having connections and influence. I'd still try to help

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DisneyDale@reddit

You have direct access to the ceo and your not wanting to be a guy in his corner? 😂

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East-Top-8709@reddit

While he was possibly may need the help….it may just be a situation where he is feeling lonely maybe and a bit lost without having the structure of the day to day of his business….? Also he rly may value ur input, knowing will know the answer, or possibly he just is looking for and needs a friend? Idk it’s a tough spot. Def is. Eventually u cld just say, u aren’t sure what the solution is n see if he turns elsewhere for help? IMHO I wld say, if it’s a couple calls a week….i think it’s the right thing to continue helping. I do believe it will get better n is most likely his struggle at the change in his life. Good luck

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Fire_Mission@reddit

You do whatever he asks. Forever. Beyond what he's done for you, "retired" doesn't mean dead. He still knows people, still has "soft power". Someday you may need him again. Think about it.

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JeffIsHere2@reddit

Help him BIG TIME! You’re very fortunate. He may no longer be the CEO but it’s likely he’s a good future possible resource. Consider it an investment in building your network and future.

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Mikeseddit@reddit

One option would be to come up short with solving a problem here and there and then refer him to the Apple Store/geek squad to finish the job now and then.

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Key_Shine3895@reddit

I’d just help the guy out. Valuable relationship.

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metsjets86@reddit

Not to mention you can ask him for career advice. Say you don't get the bonus you want. "Hey Bill how would you handle this?" "Perhaps OP you maxed out and the only way to make more is to move on." "These conversations we get to have are a big help. To see things from the other side. If i took your advice would you be willing to be a reference or point me in the right direction."

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ReadingAndThinking@reddit

"I feel like I might be personal tech support for life." Yes this is what young people do for old people. It's the deal.

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NoPublic513493@reddit

I’d help him. You seem to have answered your own question in terms of having some gratitude of what he has done for you. And while you should in no way expect it, I have a feeling you’ll be rewarded again by him in the long term.

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FerricFryingPan@reddit

Are you sure it's tech support and not "a friend to talk to" support?

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amazing_spyman@reddit

dude, he's lonely probably. listen if you want ~~bitchez and lambo~~ life a good life, take him out for a drink and ask him what he's reading and interests. ask him "what would it take for you to mentor me to become as successful as you did". even if he doesn't answer he'll think about you at 4a.m. You do want an ex CEO to think about you at 4 am. you could be on the path ~~to getting bitchez and lambo~~ to be a great person just by being close to this dude. water him like a flower, and if you need help, i help businesses all over US and EU to relate with Executives

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shantyfah@reddit

Hook the dude up.

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mxhc1312@reddit

I think he well earned your help

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tbohrer@reddit

Buddy.... hear me out.... this isn't just an old boss. This is a good friend and life long relationship that you happened upon while working for his company.

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RevampedZebra@reddit

Be good to your friends man

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HybridAthlete98@reddit

My dude, sounds like you're "in" a CEO's (whose been very good to you, your own words) circle and you're his go-to guy for minor IT issues? Hit him up all he needs, shoot the shit, get some lunches or dinners, maybe try get some mentoring or coaching. He's "retired" but still in your company and still has significant influence in management rounds. You're buddies with this guy, many of us wish to be in your shoes ;)

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Elegant_Click07@reddit

Are they doing this with expected urgency on your part or because you're someone they respect and appreciate that you are a person they trust. Some people do this because they feel a loss of power over others and this is a way to keep people under them. Then you need to set boundaries. If this is because he just likes having a reason to talk maybe turn this into a family friend thing. Invite him and his partner to go to see the nutcracker with you and your kids or to the art museum with your partner on a saturday afternoon. Stuff like that is what people dream about. If he is very wealthy and generous he may even foot the bill or invite you to bigger ticket items like sports seats or golf days. (It seems like these niceties should exist between a mentor and mentee.) Consider if he is still investing personal time in you. Or is trying to keep you in mind by referring to you with benign aid requests. If each time he asks some benign aid of you you offer an invitation to something personal he may catch on that being friends requires effort on his end.

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BigMax@reddit

You should be nice and return the favor. If you want you can start to “fade out” the support. Let some calls go to voicemail, answer texts a little slower. Don’t just cut him off, but start to lower response times and immediacy.

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xland44@reddit

YTA man, the guy gave you a career and helped you take care of a family Oopa, wrong sub...

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Cielak1234@reddit

set his ipad and whatever he wants for the rest of his life.

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relditor@reddit

Bite the bullet, Hope Bad could it be. Setup some sort of remote system to save you time.

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sscorpaeniformes@reddit

Keep helping if it’s not ruining your life. It could be rewarding and if not, you’ve helped someone who helped you.

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angrydad007@reddit

You will need his help in the future, nurture the relationship, don’t be lazy. He helped you

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gopro_2027@reddit

What's the deal with IT guys always being all high and mighty when a friend or family asks for help with their computer? I can't believe you're even asking this question man.

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Proper-Tradition-553@reddit

All time reddit post. OP discovers friendship

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Ill_Reason_3322@reddit

You already know the answer…

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eugenedebitcard@reddit

Bite the bullet and help out. He still has a lot of sway. Could be your next promotion.

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Icy-Two-6378@reddit

Just do it, just because he is not the ceo anymore doesnt mean he dont have any influence whatsoever, its still a valuable networking contact

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_losdesperados_@reddit

He sees you as a friend. He could figure that stuff out on his own. Maybe grab dinner with him sometime in a friendly capacity.

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irequirec0ffee@reddit

I wouldn’t burn that bridge.

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steevp@reddit

Do it during working hours, but clear it with whoever you report to, that way when they don't let you go you aren't the asshole.

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AmIBeingObtuse-@reddit

Personally I think you should continue to assist. Because according to your post, he has a great deal of influence. That said, I would reduce the availability of myself. Take longer and longer to get back to him over time. It'll either become once in a blue moon request at that point or he might just stop asking. And if he does ever mention it, you can always say juggling work and personal life is hard enough. Sorry I can't be any more help. Type of thing.

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Optimal_Ad_7593@reddit

Try and offload to an official source of help. An exec bought a laptop for her when she retired. She bought it online. I was the IT guy when she left. She realized the disk space was too small and wanted me to replace it, came by the office a few times to discuss it. She didn’t want just a disk of course. She wanted an OS, her apps, her data, etc. And I guess I would also have been responsible for getting her an antivirus. She just didn’t realize how much work that would be for me to provide this outside of the company context and systems. The real, rational solution would have been for her to buy a new laptop and give that one to a nephew or niece or something. But it couldn’t really say that. So I directed and helped her go to the one place in town that was the official dealership for that brand, and request a disk upgrade. Citing voiding warranty if she didn’t do it through that channel. She wasn’t super happy but it was a solution, it made sense and it got her off my back.

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IKEtheIT@reddit

bro... rich guy needs a IT guy still... help him and i bet he throws you cash after jobs are done

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funktasticdog@reddit

"This extremely nice person who has brought me further than anyone else and given me tons of money ocassionally wants my help? How do I tell him to fuck off?" Its the mindset like that that's why people find it so hard to trust people now. Just be a good person and not a selfish asshole?

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MeBeEric@reddit

He seems like one of the few dream bosses out there. Frankly keeping him in your good graces might open you up to his network more and, in turn, directly help your career. If anything try using the time y’all have over the phone to get to know each other. Seems like a good guy to have around.

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lyreluna@reddit

Why do you want to cut off your nose to spite your face?

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yubsidiangwa@reddit

Sounds like a bridge you want to keep and nurture

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drstrngelve@reddit

I'm in that exact situation and it's been 5 years since the founder retired. I happily answer every one of his and his wife's calls for help. I even call once or twice a month to see how he's doing. He's been very good to me over the years and is still a board member of the private company that I work for. Over the years I've bought two luxury cars from him that were two to three years old and had maybe 10,000 miles on them for a lot less than what they are worth. I have a deal with them where he talks to me before he sells her trades in one of his cars. Unfortunately, the last four cars he's bought aren't anything that I would like or would want to own after the one or two years of warranty they would have left. I make damn sure that I'm still in his radar.

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666forguidance@reddit

CEOs like that don't exist anywhere outside your fairytale life. If you don't help that man, I hope you get all the bad karma.

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Dr_Bendova420@reddit

Your net worth is your network!

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pallladin@reddit

"Sorry, I don't know how to fix this one". You could slowly try to make yourself useless.

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BigGaggy222@reddit

You help this guy out when he asks. One bonus check would cover his asks. How is this a question.

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KingHiggins92@reddit

You sound like an arsehole.

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HorrorMarketing2164@reddit

Bite the bullet, don’t burn this bridge.

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ComprehensiveBee5350@reddit

He seems like a good guy I would help him until it gets annoying. Then just saying “I don’t know or I am not sure” whenever works preety well. Eventually he will stop asking and find someone “who knows”

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RollUpLights@reddit

I wouldn't say no to them, but I would suggest that they owe you some small gift like beer, wine, or a lunch/dinner with them from time to time. Those are pretty inexpensive in the scheme of things for IT work, but still not free. If a friend of mine needs work done on their computer, they owe me a 12 pack or a bottle of whiskey depending on how much work it is. That's my "standard" rate.

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iareeric@reddit

Yeah, sounds like you’ve answered your own question. This guy sounds like he’s been with you for quite a few milestones that he even helped facilitate. I would continue helping him out, it sounds like that is a relationship that you should probably continue to nurture.

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FantasticBumblebee69@reddit

send him a contract for your service at 3x your salary. Make it hoyrly and he jas to buy 10 hours as a retainer.

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caninessharp@reddit

His names on the building, he’s helped you financially and career wise. I can guarantee if you get in a pinch at that place in the future, he’d be one phone call away from taking your side. Yeah I’d do his tech support for free. This is networking, it’s gonna pay off.

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KlatuuBaradaFickto@reddit

You maintain this relationship like your life depends on it. You're worried about *money* when you have this guy with extensive *connections* who remains connected to you by *choice* ... What's more, this person was so good to you in the past .. Listen, be like a son if he doesn't have a son. Be like a friend if he needs a friend. Don't expect a payout, but don't be surprised when you benefit from this connection, and the ones that this connection will lead to.

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Oldandslow62@reddit

If you’re not being asked to come on the daily is it really that much of an inconvenience? If not then showing this man your appreciation for what he has done for your family is good karma. But on the other hand if it is becoming a chore then a good conversation about how much help you’re willing to give would be helpful.

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Odd_Category2186@reddit

That ceo is worth every second keeping his tech working, if the shit hits the fan I imagine he will be first in line to help you out, don't burn that bridge. If it makes ya feel better tell him he owes ya dinner after a fix

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cyrusm_az@reddit

Sounds like he did a lot for you. Maybe you can help him with some free tech support since your career advanced so much with him

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Centuurion@reddit

Sometimes just be "busy" and unable to help, when you need it. He sounds like a good dude and I'd put up with it as much as I could, all things considered.

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NoteSuccessful1690@reddit

Bite the bullet, and please tell me where to send my resumé.

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Due_Goat_7584@reddit

Just help a guy out it's not like you're mowing his lawn

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Extension_Radish_139@reddit

You can’t help this guy out once a week?😭

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Democrazies@reddit

bite the bullet

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L0veToReddit@reddit

Euh yes obviously, people has endured so WAY WORSE lmao.

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Faltenin@reddit

Consider also that maybe these are just excuses to hang out. He’s probably bored and lonely. Turn this into a friendship. Fox the iPad over a glass of his expensive bourbon and have a good time.

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macrowe777@reddit

Sounds like he deserves it, give him a fair few free and casually offer to setup a retainer for him when it's getting regular

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No-one-is-watching@reddit

Take the call as an opportunity. Get advice from him on career moves you’re making. Continue to build your friendship. I’m sure they have a good network to help you in any potential career moves you’re making.

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69FireChicken@reddit

Help during work hours when you can. Tell your current boss, "hey, cutting out early, gotta run to Old Ceo's place on my way home to help him out" . It's loosely part of work, let it be part of work! Sounds like a cool guy, worth going out of your way a bit. If it gets to be too much you'll have to find ways to politely decline.

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LoopyMercutio@reddit

While there’s a limit to how much gratitude versus “help owed” there may be, it’s only been 2 months. You may want to wait before cutting off the help for a while, and also show him how to deal with the things himself (PowerPoint slides, step by step instructions) for when you “aren’t available” or “out of contact.”

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Remarkable-Owl-5712@reddit

Yeah dude, he sounds like he earned it. Just help him out every once in a while.

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LowCompetitive1888@reddit

No reason to burn bridges. I'd keep helping him.

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vze2pn5b@reddit

My best advice is seek the counsel of your boss. That way you have "permission" to help or not help. It's always possible as one of the CEO's retirement incentive/perks the company is obligated to support him for a year or more with administrative/tech support, office space, etc. He may not realize you don't understand his requests are "normal" and you're supposed to help him.

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BVirtual@reddit

You are a good person to help him out. At some point you will be right to think of your time as valuable and desire some type of remuneration for visiting his home. I would not draw the line in an arbitrary way. Nor is cutting him off cold turkey a good thing for you. Does he still appear at the office to advise others? Is he getting paid for those appearances? Or is he offering and providing phone meetings with existing staff, and being paid for it? What is your plan for your future? Continue to work at this one company until you retire? Or work at 3 or 4 other companies, increasing your pay each time, so when you retire you collect from 3 or 4 pensions/retirement accounts, not just one? You can triple your retirement fixed money income that way. You must now make plans for your retirement? Right? Which means planning your future, in 2 year increments. And 5 year and 10 year. Where do you want to be in 10 years? Start with that. Work backwards to in 5 years? In 2 years? How will this guy help you achieve these goals? Ask him, once you have a one page plan for each of 2, 5 and 10 years. Ask him if you are thinking straight on this. Get a mentor out of him for your retirement, and your future??? I would. He sounds like he succeeded, right? Can he aid you? Is he of that mind? Ask if you should start a moonlighting company providing tech support? If you want to hint you will at some time in the future need some type of compensation. His advice, 1 hour a week... would that be valuable to you? Here is what I would ask him. Who is his financial advisor and will that advisor who invests his funds into diversified stocks, bonds and ETFs, start you going at just 10K? Where does he invest his money each year, like in a housing development that doubles the money in 2 years? What is the minimum to buy into such? Can he introduce you to other future earning and retirement potentials? Hope this helps. Good luck in achieving his degree of success when you retire. (hint hint...)

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Patillas-Inc@reddit

What is your issue? Not liking your job? Ask yourself why you shouldn’t.

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bhambrewer@reddit

The CEO retired. This is not OP's job any more.

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Patillas-Inc@reddit

Ex-CEO asking you for help? You should be honored! Period.

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my_name_isnt_clever@reddit

Does the honor convert to USD in my bank account? Since that's what I'm here for and that's the only thing every CEO cares about while they're in charge.

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Patillas-Inc@reddit

It does not convert at the moment but it will in the long run, exponentially. How? Promotions, business partnerships or just a good reference that translate into a much higher position, it’s just business ethics. I get a lot of you don’t understand it’s okay 👌

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my_name_isnt_clever@reddit

He's retired man. He doesn't work there anymore. Also "business ethics" is an oxymoron.

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Patillas-Inc@reddit

I get it man, pretty sure you wouldn’t help him unless there’s money in table. I wouldn’t ask you either for sure, best of luck 🤞

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Ok-Strength-5297@reddit

what a boomer take

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Hugh_G_Rectshun@reddit

My friend, you have an executive caliber friend you can use to network and use as a referral. Don’t burn this bridge. How much time is he truly eating up if he’s inadequate with basic technology and it’s your specialty?

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Early-Journalist-14@reddit

Find out if: a) continued association is something you want and/or benefit from b) if yes, how much time that is worth to you Then spend the appropriate time for whatever reason you deem relevant. If the demand outweighs your ability or willingness to provide, i'd recommend this: Turn down one of a few requests, saying you're busy in some way. start turning down every 3-4 requests, slowly escalate. At some point he'll stop asking.

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Rhinoseri0us@reddit

Trust is a valuable thing. Seems like the type of guy who’s corner you may want to be in. Just my $.02

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reactor4@reddit

It's good karma, just help him out. He'll call less and less.

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imranhere2@reddit

You answered yourself. Christ

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TheIthatisWe@reddit

It’s not biting the bullet. You invest in the people that invest in you. Also mentoring like everyone else said. He’s not a rung on a ladder.

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BubbleSlapper@reddit

In today's climate, in this fucking shithole the USA has become, in this economy, and all he does is ask you for some help with some tech at least once a week? The fact he said yes to your promotion and approved raises? The only currency he asks in return from you is some socialization and some help with some tech shit. You be a huge moron to say no or burn the bridge. Dude probably even sees you as a friend at this point.

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PlntWifeTrphyHusband@reddit

Not many people get to maintain a friendship with someone who has connections like this. Stay in his network. It will pay off in the future even more.

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killjoy1991@reddit

Just accept it. Sounds like a bad bridge to burn.

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Impressionist_Canary@reddit

Damn man, not what I was expecting based on the headline. Just help the guy, even if only out of self interest sheesh.

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myersdr1@reddit

At this point this is networking, your little "inconveniences" could lead you to a better position at some point. This is not just someone you brush aside. This is someone you keep around, you help them, they WILL help you.

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PayAgreeable2161@reddit

This guy has given me "5 figures bonuses" Do i need to do level 1 tech support? Why don't you go over for a beer and be his friend jesus

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G0G28G91Z0@reddit

I would do everything that he asked ( I’m sure he asks very nicely), and would be grateful to do it. You never know, even though he is retired, those favors could lead to something big for you and your family one day.

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Absolute_Bob@reddit

Sounds like tolerating it for a bit might not be the worst idea. Who knows what kind of connections that kind of relationship might open up for you down the road. He's probably just struggling through the transitional period, see if it does down after a bit but maybe say no or not yet a few times if it doesn't.

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One_Animator_1835@reddit

You start asking for favors in return!

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Bed_Worship@reddit

Sometimes it’s good to be kind, and this seems like the right person to be kind to given your life trajectory under him.

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Hefty_Economics_2414@reddit

Guys is this not sarcasm

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askanaccountant@reddit

I worked 11 years for 11 different CFOs, ownership bonuses paid out on growth of the comapny which ballooned, never once did I ever receive a bonus even close to 5 figures, and I carried a department on my back for years. You have a connection for life and if that means sometimes you gotta help him out, fuck it.

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bobo_1111@reddit

I agree with everyone saying it’s a great networking opportunity and he was awesome to you and hence your family so I would continue. Side questions…. Is it just phone support? How long are the calls? Do you visit his house? Does he pay you? Does he give you gifts? Do you do the work on company time or after hours? I guess I’m asking because if you spend 15 mins a week on the phone it’s all good but if you are spending 8 hours every Saturday at his house working on stuff that could be a different conversation.

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Craic-Den@reddit

If you say no, he might say no to other ways he could be willing to help you out. He's got ties to the company still, he can put in a good word to help you climb the ladder even more. Fuck it invite him over for dinner and straight up ask him what you need to do to get to a more desirable position within the company. It's always good to keep these people close.

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jara76@reddit

I will keep helping him… it seems like he helped you for a long time.

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Ghostribe77@reddit

I say seal his driveway if you have to. This seems like a good dude to know

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n_o_t_d_o_g@reddit

Turn this into your advantage. If he founded his company he is probably rich. Charge him for your services. He used to sign your paychecks, he knows how much you are worth.

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FriendlyBee94@reddit

OP got promotions and raises from this guy but want to burn bridge because the guy retired (not directly affect OP working conditions). Grateful much, OP?

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thedevillivesinside@reddit

He signs your 5 figure bonus checks? Jesus. Help the motherfucker with his email

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Lucreth2@reddit

I didn't scroll all the way down but one comment I didn't see is that a lot of this stuff also sounds like part of the adjustment phase to retired life on his own. I doubt the requests continue with such consistency for long and he's ABSOLUTELY someone you would love having in your corner. Just help him out and, if possible, try to stay personal friends with him. It's definitely worth it!

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johnmichael956@reddit

I've been in this exact position twice, and n this case, I would help out. Sounds like he's been in your corner numerous times, and probably a good friend/connect to continue to have.

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PopperChopper@reddit

I couldn’t make a good argument not to help him.

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1968Bladerunner@reddit

I stepped away from IT 7.5 years ago when I semi-retired, but still get the occasional "Help" call. Few go beyond 5-10 minutes, & it's only ever from prior clients. I figure I owe them enough, for 25ish years of help keeping me in business, to justify a few of them a 5-10 minute call now & then. A small inconvenience for me, but a lot of goodwill too... & the occasional bottle of something nice dropped off at my house! If your ex-CEO still has high-up friends within then I'd say it's a small price to pay to keep the waters smooth.

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VinylJones@reddit

You do the following: say “no”. This is easy math.

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Justan0therthrow4way@reddit

It sounds like he has taken care of you as an employee of his and been a great friend. As long as this continues with the new CEO, I wouldn’t mind helping him out with a bit of tech support. It also sounds like he realises shit ain’t free so he may well ask “what do I owe you” and just tell him to buy a round of beers or shout some lunch.

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tdmoney@reddit

You know how many people would kill to have that kind of access to an executive? Even at a small company, it’s all about building relationships and making yourself useful.

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CamGoldenGun@reddit

sounds like this dude changed your life... don't be a "but what have you done for me lately" kind of guy. Your once-a-week of support to hand hold him through tech issues is miniscule. You never know if you get laid off and he has a CEO friend that would hire you on elsewhere or he bought a computer with a 5090 in it but doesn't need it anymore and is going to give it to you, etc. I'd be calling him up once a month for lunch.

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stevrose@reddit

You should be fine. Thankfully office politics isn’t a thing and everyone is just professional and fair all the time. Nothing bad will come from pissing off your extremely influential former CEO.

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Ok_Koala315@reddit

Lol this is the problem with people nowadays. You’ve mentioned all the good he did for you (including multiple five figure bonuses). And you’re complaining about a transition period? He retired two months ago man. So let me get this straight. He was a great boss, both culture wise and fiscally. He just retired. Hes asking u for little bits of help here and there. He has connections clearly. And you’re complaining about helping him out? Excuse my language, but you sound like an ungrateful little chit. Lord if you were my child I’d be so disappointed in you. Since you’re so ungrateful, look at it strategically. Help him out. He has a lot of connections and can still use them to help u out in your career despite him being retired. My lord, you’re so shortsighted as well.

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funk-of-ages@reddit

help him. have a boundary in terms of time or effort. such help generally leads to opportunites in the future

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blastmanager@reddit

Given that he is the founder and long time president of the company, his words will likely mean a lot in the board room and among senior management for years to come. He's also probably a somewhat important person in the industry and in your area. If he's not too old, there's a good chance he will continue working on some other projects, albeit "part time" and not necessarily immediately. Keep a good status with him and it might continue to affect your career positively.

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janacek1854@reddit

Keep in mind that people are lonely and sometimes older people do not know how to communicate. It sounds like he wants to keep in touch and doesn't know how to do it without an excuse.

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Same-Shoe-7576@reddit

to chat the comment said is not the comment being appropriate

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fa11ax@reddit

Just let him know that he knows you don’t get paid enough to offer free tech support for life and it’s $100 per hour from now on.

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Just_a_n00b_to_pi@reddit

Definitely keep doing this and if somehow he becomes self sufficient then put an annual reminder on your calendar to check in with him. You might be in a good spot right now but you never know what’s around the corner. Always good to have a strong network and that’s hard to do if you cut ties with everyone as soon as you’re not really obligated

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neverdoneneverready@reddit

He sounds like he misses you.

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mojo20010@reddit

If he is only calling you for help and is not a friend he is kind of using you. Use him back ask him to drop hints to the new ceo that you need a promotion and really become his friend. Friends help each other out for sure.

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fillswitch@reddit

Yeah like everyone said, help him. It would be annoying if the frequency of his requests get out of hand, even for a friend, so also implement some boundaries for how quick you get to his task. In my experience, this shows a person "He's willing to help, but isnt always immediately available". This can cause them to look for help elsewhere in the meantime or will set their expectations appropriately, and allow you to breath a bit. But yeah, help him out some.

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Consistent_Ad7426@reddit

What difference does it make the fact that he has retired? has this happened before? would you be asking the same if he was still in officially in charge? unless helping the boss with personal home tech stuff is part of your job, it really shouldn't make a difference whether he's active or retired. It sounds to me like you really don't appreciate him as much as you claim, and are just worried that if you refuse, he will either pull some strings against you or won't be willing to pull strings to your advantage (hence your fear of "burning the bridge").... my point is, be honest to yourself: if you saw him as a mentor and a friend, the question is easy, you do what you can to help your friends, you're not under any obligation to say yes to everything, but it probably takes many calls and zero reciprocity before you're afraid of becoming your buddy's tech support. If you instead see him as social capital or an authority, it's just a matter of how much time and effort are you willing to invest in keeping yourself on his good side and adjusting your response accordingly (eg. maybe you're not willing to go to his home, but can try to help him on the phone, or offer him to pass by your place instead)

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EmptyBasil1481@reddit

Yep in the same boat. It will get better and best to just do it. Maybe after six months you can address it with HR if still happening.

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Codplay@reddit

So a few questions to think about: - how long is it taking to help with his requests? Are these 5-10 minute fixes, or usually take an hour? - Is this happening on work time, and your current higher-ups are okay with it? Or is it on your personal time? - Obviously these are his personal devices, but are they set up in a way that makes it easy for you to support them? From my quick take, I agree with everyone else that the guy has done a lot to help your career and set you up where you are. That kind of social connection is invaluable. The guy whose name is on the building thinks highly of you and wants your help specially?? That’s priceless. But if this support is time consuming, on your personal time, and frustrating without decent tools, then I could see needing to discuss some boundaries. Obviously very different, but my brother-in-law and I are tech support for his whole family, and his grandmother keeps a list of small annoyances or things on her computer or iPhone/iPad. Once that list either gets to ~6 items, or one of the items is security related or an error she can’t ignore and stops her using the device at all, she calls one of us and we go over to fix that issue and the other list items, and have dinner. Conceptually that kind of arrangement could work as well IF you were finding that it was taking up too much personal time, or current management says it can’t be done on work time. However, if the current c-suite is more than happy to let you spend some time once or twice a week to help the retired CEO with his tech… well, sounds like a GREAT way to keep in touch and build a stronger social connection with a guy who has had a huge impact on your industry (at minimum in your area).

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HardWork4Life@reddit

Don't be shortsighted. This the kind of CEO you would like to get connected. It's an investment too. You are lucky to have this kind of opportunity. He has helped you a lot. He will probably continue to do so.

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Better_Peaches666@reddit

He's given you multiple Christmas bonuses in the 5 figure range? Bro, he clearly did his part, now it's time for you to do yours. #Help him out!

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chicagoan987@reddit

I say keep helping him for awhile.

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TotalResearcher4308@reddit

I used to side gig IT for my old CEO and his elderly mother. Maybe negotiate a deal with him for some side gig Pay after hours, etc..

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torque1912@reddit

Bite the bullet and help the old man. He sounds like the type where this bullet biting and whiskey drunk baboon meditation is gonna help you in a big way down the road. And maybe not all the far down the road either.

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landon_masters@reddit

Yes. He might not even need the help, just wants to maintain a relationship & check in on you. I have a mentor that I would do anything for, even if he leaves our company, no matter what. Loyalty goes a long way, and both ways.

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MarfanoidDroid@reddit

"Hey everyone, this guy changed my life and I owe everything to him, but he can't help me anymore and he still asks for help with simple things on rare occasions. How do I get out of this?" You're selfish as fuck and didn't deserve what he did for you

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Whatever5588@reddit

Seems like he has been a generous mentor for years. The fact that you are asking this question 2 months after his retirement tells us a lot about the type of person you are. People like you cause good bosses to become transactional.

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Talex1995@reddit

Guy seems genuine and the fact he’s been that kind and supportive when he was CEO just shows he’s human, Id honestly help him. Maybe be more restrictive depending on the problem to draw a line but basic shit then screw it

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Cyberspots156@reddit

I get it because I’m retired and I had my own business. You are a connection for him to the company he built. He obviously considers you to be important. You are in a unique position that few people outside the C suite ever experience. You said he did a lot for you for five years. He put food on the table for five years. That’s not a little thing. It’s up to you, but don’t you think that you might owe him a little more than two months? You have a wonderful opportunity and it’s entirely up to you whether you take advantage of it or walk away. My feeling is that if you walk away, then the time will come that you will regret it.

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Safe_Ant7561@reddit

you help him a reasonable amount and be grateful for the opportunities he has given you and just look at it as growing the relationship.

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molsonoilers@reddit

Business and personal should be kept separate. Him approving raises and giving bonuses is a business decision, nothing more. You giving your time is a personal decision. It's only you that can decide if it's worth it.

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SLAPUSlLLY@reddit

Had a client who is a high court judge ask for a rush job before Xmas. Done, and done well, and sent a zero charge invoice with seasons greetings. Networking. I would keep that relationship ticking personally. Test it out by asking a small favour, see where it goes.

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SaberToothGerbil@reddit

If you can, help him on the clock. Let the company pay you for it. If it becomes an issue, blame the company for telling you not to help.

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23523543@reddit

don't burn that bridge it will cost you

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Goosexi6566@reddit

No, Honestly it seems like a chore but I would keep someone like this in my good graces as it’s a step up from your normal clientele and it’s more beneficial for you than it is for him as he could go to many others with his issue… but he trusts you. I deal with affluent and higher end clientele and in most cases it’s worth it. If he doesn’t have a super inflated ego he will most likely put in good words about you if his consideration is still used at your company and if not most of these people give very lavishly so I wouldn’t say no.

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lemme_just_say@reddit

I would help him.

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ItsaHardNo@reddit

The subtle thing to do is start asking him for favors in return. Escalate the return favors to be of greater value. If his favors increase, so do yours. Just make sure he delivers first.

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throwawayorsmthn12@reddit

If this is personal time their is no way I would do this, more work? U have to be kidding. He's not even a friend too. Yea no way man, do it for a bit but set boundaries.

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ItsaHardNo@reddit

The subtle thing to do is start asking him for favors in return. Escalate the return favors to be of greater value. If his favors increase, so do yours. Just make sure he delivers first.

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busbybob@reddit

Of course you carry on doing it, long shot chance your in his will

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ImyForgotName@reddit

Help him with his shit.

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This-Obligation1633@reddit

what advice would you give to your son or daughter in this position?. would you tell them to start telling him no. ? Or would you push them to do the right thing? We can’t justify this decision for you to make you feel better. Just do the right thing. You’re the one who has to live with it.

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SLWoodster@reddit

Seems worthy. Help him. Ask for short cut to the top to help your family.

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Tiredofrepost@reddit

You're an A hole just to even consider in not helping him.

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larentquestion@reddit

Go help him, he helped you

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Kwerby@reddit

I think even though he’s retired this fella is still a winning ticket into bigger and better things.

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BattleSensitive3467@reddit

Sounds like he gave you everything you wanted, just help him out. And if the task is too exhaustive let him know you're too busy with work things

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pick_up_a_brick@reddit

Keep this relationship. It will continue to benefit you in years to come. Doing minor occasional tasks will end up earning you 4-5 figure salary increases in the future.

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old_school_tech@reddit

Keep helping them. Just not straight away. He's helped you over the last 5 years. Sometimes relationships are worth it. Dont forget those who helped you.

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deputy_dawg6531@reddit

Seems like he's helped you out a lot. Take ten minutes to help the guy, you'll be fine.

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n8bdk@reddit

If it doesn’t produce accolades in 2 years I’d start kindly rejecting every other question and eventually all of the requests maybe in 3 years. Who knows, he may have a “bonus” check for his personal IT guy next year. If the bonus checks keep coming from him personally, the “favors” keep coming. One hand washes the other.

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loowig@reddit

Is this rage bait? Fix that man's laptop ffs. And if he regularly bothers you after another couple of months mention it to him.

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Pizza_Witch_@reddit

I would not say no in this situation. This is a person I would want as a friend. And if they are calling you for help outside of work, then that is a two way bridge and you never know when you may need to cross it for help. I'd keep helping them. But if this isn't your cup of tea maybe just don't answer the call. See if they can fix it themselves or find someone else to fix it in time. I personally wouldn't directly say no but you might make yourself less available if that is really what you want.

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Jokkitch@reddit

It depends on how much he’s calling you. Couple times a year? Once a month? Week? Everyday? There’s a limit for everything.

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Rolling_Kimura@reddit

Everyone all says, "yell out if you need a hand", but it becomes too much for people.

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hospicedoc@reddit

My guess is that he still owns the company and he is still your boss in a roundabout way. I would continue to help him in any way I could, and let your boss know that you're doing it.

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clearedmycookies@reddit

Either this is a friendship thing now, or you got a nice side gig for extra cash. Either way, the answer isn't "no"

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Kind_Paper6367@reddit

He gave you raises, promotions, 5 figure bonuses, and your debating on continuing to help him with his iPad and email?? Help that man and tell him to call you if he needs anything else.

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Respacious@reddit

Bruh, from what you said it seems like he went way above and beyond what would be expected from an employer employee relationship. Should be a no brainer...

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frosted_talons@reddit

Seems like an invaluable mentor - and everyone should have friends that aren’t their age — especially older retirement age men. Please put up with him, it’s a huge adjustment for some people to retire and especially for men, to be social

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D3moknight@reddit

It sounds like you've gotten a lot out of a very positive relationship with him. Someone like that I would definitely be willing to help out outside of work. In my opinion, that's a good resource to keep happy.

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Best-Ad9099@reddit

Bite the bullet

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ScalyPig@reddit

If you’re on the clock when this happens then quit whining. If you aren’t, don’t answer if you’re busy

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Mateos75@reddit

Take calls during work hours

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Ricky_Rocket_@reddit

I wouldn't say you owe him anything, but he was good to you and he didn't have to be, it's rare to find a good boss these days, especially a generous one that isn't just looking at the bottom line. He also likely carries a lot of political clout and will for a while. He can make you disappear with a snap of his fingers, i'm not saying it is right, but it's the world we live in. Continue helping but place some boundaries. Figure out what those boundaries are and how you want to present it. Be gentle. He probably doesn't know what he's doing to the point he thinks you're even friends and he is asking a friend for help. Something like, "hey I have no problem helping you out with your tech stuff, but i'm very busy with work and family life. Would you be okay meeting up for lunch (or dinner) once or twice a month and getting these issues addressed? then see how long these meetings are taking and go from there. I would hope he would offer to pay but I would let that develop organically. These may turn into catch up with a friend sessions and address some quick tech things, who knows.

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therankin@reddit

Yea. I had a similar things happen early in my career, but the ceo and his wife would pay me separately for support calls. I even helped his Mom a few times.

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Ok_Bus_3528@reddit

Of course help him. Wtf dude

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Zookeeper69xo@reddit

I don’t care if that guy calls me at 1 in the morning for help replying to an email, I’m helping him. Is it annoying? Absolutely, but it seems very much like his help is worth the inconvenience.

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Ex-zaviera@reddit

This sounds like a great Dear Alison question (ask a manager). I know she points out your family upbringing to personalize resolutions.

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EroticTragedy@reddit

It's okay to set boundaries. This is a colleague, albeit one that you have a relationship with, it still falls in the realm of inappropriate contact and if you don't set a boundary now, yes, you could become forever obligated and saying no becomes increasingly difficult, frustrating, and more likely to burn that bridge due to your feelings on the matter being disregarded. The polite thing to do is, for the last time you see him for this sort of thing, is say "I don't mind helping, but I still work for the company. I suggest you ask xyz (intern, freelancer, someone you know that can give this person the time you don't have for it)," He will respect this if he respects you at all, which it seems like he may be an understanding type of guy but no one knows. This is better (or at least some form of hard no) than waiting until you get emotional about it / fed up

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003E003@reddit

Yes you bite the bullet. Call it being a friend or call it "networking". You have NO IDEA how this contact might help you in the future or what kind of favor you might be able to call in. Or you can just consider it being nice to someone who has been nice to you. Not EVERYTHING has to be transactional.

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Live-Ball-1627@reddit

This sounds like a friend. Take care of friends that consistently go to bat for you.

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itsmequintino@reddit

If this were on AITH I would say: YES! Help that old man, he probably misses you and work!

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Dis_engaged23@reddit

Address the businessman in him. Politely inform him that you cannot continue to do the work for free. For a small retainer you might continue to help, but he should understand such help has value.

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oichie_uk@reddit

Ive been where you are.. I had so much respect for the guy that I just carried on like he was still with the company. It was like that for about 4 years until I left the area for a new role.

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nickjacoblemay@reddit

Ohhhh my dude. What you should be asking is how do I lean FARTHER into this relationship, not away. He's a retired exec, who knows lots of other execs, who contacts you weekly. That is an incredibly invaluable relationship that a lot of people work very hard to get. Obviously he likes you enough to keep calling. Tell him he can take you out to lunch for the help. On top of all of this it sounds like he's been very good to you. Congrats on never having to worry about getting a high level job ever again.

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Then_Version9768@reddit

I agree with others here. He's essentially become a friend of yours. Treat him like one. He did a lot for you, and now you'll be doing a lot for him. You take care of your parents in old age as they took care of you. That's how our lives work. Make time when it's at all possible. And do it in a cheery way.

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NoodlesSpicyHot@reddit

Could you offer him a support contract with you on retainer: 2, 5, or 10 hours a month, as needed? Now he has his own personal Genius Bar, and he can ask as many questions as he wants about anything tech-related for himself or anyone in his family.

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WorldWideNickle@reddit

Buddy, even if you dont like him as a friend and you feel like he's taking advantage of your time... just play the politics game. You'll be happy you did.

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Aggravating_Key1353@reddit

It can feel like all you are is tech support to them, if all you think you are is tech support to them. To some, that's true. But the way this man made you feel should prove that He's not asking for money. Just some time. And I'm sure there's small talk. Ask him to lunch sometime. He may have some good advice to offer. Sage to sage.

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thewispo@reddit

It sounds like you're pushing all the reasons why you should continue. However, from personal experience, end it. It is for life and has zero benefit other than the person asking. That's how these people become CEO. But they no longer are, are they?

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acf6b@reddit

Talk to your current leadership, if it is a company like I used to work for, you still worked for the retired ceo/founder as he still owned the company just had someone else running it. Just make sure it’s company time/paid type thing.

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Imanextra@reddit

He's clearly got the money, you should establish him as a client of your new side hustle.

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troutman2425@reddit

as a former ceo, multiple times, I'd suggest you address it candidly - expressing gratitude, and suggesting he utilize the company resources as he likely has access based on his "retirement" agreement. At a minimum, share that you'll address as you have time.

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GypsyBl0od@reddit

He’s done all that and you can’t help in a few simple things?

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musajoemo@reddit

Help him out on company time. Figure out how to do this—then help him out.

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tha_vali@reddit

Is it too much for you for being the IT guy ocasionally ? Doensn\`t matter who it is if he is not abusing your kindness. After all, if it was the cleaning lady askiing you your help, you wouldn\`t helped her ?

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ACasualRead@reddit

I still do IT for people in jobs I worked at over 10 years ago. They have been valuable connects and got me a few gigs. Totally worth helping him out especially if it’s only here and there support.

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velwein@reddit

With how much he’s helped you? You don’t. Especially if he’s still friends with those who run the company.

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GorgieGoergie@reddit

help but on the clock

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First-Bother-3766@reddit

These comments are insane. You don't owe him anything. You were his employee, and clearly a good one given his bonuses / promotion. You're the one that provided his business with value. Politely explain that you can't spare time in your personal life to provide him with tech support. Do it sooner rather than later. Make sure to be clear and firm. Cut him off.

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johninwnynew@reddit

If he's been as generous and good to you as he has, I think you really should help him out. I mean it's not every day I'm sure. It's the least you can do. He sounds like a good person. Gave you bonuses, raises etc without question. Cmon. He was decent to you, I think you show some gratitude and help out in return. You asked for an opinion, that's mine.

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Candid-Crazy2542@reddit

Just help the old fart. Be his tech dude. It’ll benefit you in the long run.

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Beneficial-Spot-4429@reddit

Don't be petty, sometimes those relationships are testing but sounds like he's done more than enough to help you in life.

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Internal_Set_6564@reddit

You help him. It’s not like the guy is an asshole. If he calls you at 3am because his porn won’t load, sure, ignore him. During business hours help him. He still has influence

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SlightlyShyOne@reddit

Don't answer until enough time has passed that he figured it out. Or jokingly ask if wants to hire you as a consultant and see what he says.

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ViscidPlague78@reddit

For all the karma he's given you, I say eat some shit it will eventually come back around to you in a good way as it already has with his treatment of you. He's someone that if shit gets bad can be a networker for you. So keep doing the good karma stuff it will come back to you in a good way.

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oodex@reddit

How you feel about it is your thing, but a change of view can sometimes help a lot. Right now you view him as you being his servent, but what you describe that you help him with is nothing short of - drumroll - a friendship. So not using someone, but needing the help of a friend to understand something one can't do on their own. Or, also possible, could achieve on their own but the social exchange is wanted. Again, how you feel about it is your cup of tea and just because someone may want to be a friend or views themselves as a friend, doesn't mean it's the same the other way around, but the point I want to make is that if you never viewed him as a friend you also can't view his actions now as a simple friend reaching out for help.

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duffchaser@reddit

this guy sounds like a genuinely good person why would you not want them in your life.

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General_Sky4142@reddit

On top of everything he sometimes gave you 5 figure Christmas bonuses…? If I were in your shoes I would be his slave. I’ve lived off of about 26grand a year for several years. That kind of money is literally unimaginable to me. I donate plasma after work twice a week, and hit the food shelf on the other days I don’t donate plasma.

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LTTP2018@reddit

help him! for a set amount of time, then reevaluate.

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Xavinights@reddit

Is he the owner? If he still is, that's your job, if he has 0 to do with the company no

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Dapper_Platform_1222@reddit

This is the answer.

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TMBActualSize@reddit

Job Market is getting wonky. This guy could call in a favor for you.

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Budget_Ad5871@reddit

Help the man

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Ok_Eggplant_6143@reddit

you REALLY should be friends with him, or try hard to be.....

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Difficult_Arrival_59@reddit

Just look at it as you now have a very influential, probably well-off Uncle who needs some tech help here and there. If your schedule is tight when he needs help, let him know, but offer alternative dates/times to help him.

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daytonakarl@reddit

Yeah I'd keep him onside, probably needs a mate and isn't quite sure how that works as he's been focused on other things for so long, and he may want to gossip about the job too Stick with it, it's a little bit of your time but worst case and you'll have a friend who knows how to run a business

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roblqjm@reddit

Bro help that fucking boomer with his iPad, are you dumb?? I'm sitting here on the toilet with no new truck on the driveway btw

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MaTOntes@reddit

I have a professional connection who has been a huge boost to my career and has benefited my life massively. How do I stop having this professional connection because, ugh, basic support is annoying? What on earth are you proposing? You've defined a long list of huge personal and professional benefits this connection has enabled for you. You are in an incredibly privileged position.. and you want that to stop? If the support is getting annoying just manage it better. Get him to create a list of issues and go over to his house and try to knock a bunch of them out in person.

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bcardin221@reddit

Help the guy out.

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ryoko227@reddit

You could not have made a better case for this man being someone who is worthy of not only that aggravation, but also of your time. I feel like you have already made that case yourself, and that you are more wondering why someone (even in a work setting) who has admittedly helped you a whole hell of a lot over the past five years, why is it then, that doing these small tasks bothers you? I'm the same way, many small requests chap my hide, even for the people that I love. It's one of those cases of bite down and bare it, he's earned it. Of course, like some others have already stated, grab lunch with him. Who knows where that might lead.

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quietimhungover@reddit

Sounds like you're in a dream scenario. Do not fuck this up! If his name is on the building and he's got your back like you say, you help him out. Besides it can't be that time consuming to help him with that stuff.

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RideAndRoam3C@reddit

Sounds like you know the answer. Take someone Jr with you next time and get him familiar with the person too. Then at least if you are too busy to come help him at that very moment you have someone you can send in your stead.

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MrSniffles_AnnaMae@reddit

CEO retired and is staying in touch with you? Those are nonsense reasons to stay in touch with you. I bet he has plans to re-boot or start a new venture and wants you to be part of it. He is keeping in touch with you for only one reason: To find the opening to make the new opp pitch to you. You could just roll with the punches or you could just be spiteful and selfish with your time, and see how that goes for ya. 🥸

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Mammoth-Mango9432@reddit

Time heals all work requests.

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Low_Heron_5783@reddit

Think about this real hard OP...

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skiddily_biddily@reddit

Does he pay you? Are you on the clock at work when helping him? Setting boundaries is fine. You can also just say you are busy or not available. If you conveniently handle all of his IT problem, you are setting the precedent. You can still help him, at least sometimes, if you want to.

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Purpleninja1132@reddit

Saying no in any means would be burning the bridge. From what I read it sounds like the ceo was an actual human being and cared for his people. He wouldn’t be calling you personally if he didn’t like you enough, and he clearly likes you. Next time go out of your way a bit and help him out, give him a few tricks that me might now know. Tell him about videos online that you’ve used and like for help before, or make the videos yourself.

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StructureMost2180@reddit

Dude you are lucky!!! Just ask him for LUNCH occasionally

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duckstrap@reddit

An interesting question. First, I might consider helping him out of gratitude. It probably won't be forever. Second, not sure what your career goals are, but I might consider asking questions at each of those encounters - some like "Hey, I am so appreciative of all you have done for my career. Are you seeing any opportunities that would be a good fit for me?" Having a powerful, trusted advocate in your corner will not be bad for you.

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chado99@reddit

Why not start a side hustle LLC. Sounds like he might be willing to pay for concierge svcs

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Global-Resident-647@reddit

>Do I just bite the bullet, and accept that I'll have to help him with his shit occasionally? Or is there a point to set some boundaries? If so, how do I do so without offending him or burning any other bridges. Help him help himself. Teach him to google and troubleshoot himself. We did to my dad and my wife's grandmas husband. They've never been more proud being the techsupport for their circle of friends and family now.

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CocoBerryIsBestBerry@reddit

You choose your company and he chooses you. Seems like a genuine guy. Id keep helping.

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avalisk@reddit

Hes your friend now. Keep it that way.

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randomuser6753@reddit

Just help him out - he's helped you out for years. It doesn't cost you much if anything, and is a nice thing to do. Think long-term instead of short-term.

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Outside_Interest_773@reddit

I have a co- worker, actually a few, who always calls me for tech help. I would miss it if they stopped calling..

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WorriedBig29@reddit

Dont be a dick

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youngrb3@reddit

Yes - I do not want to say bite the bullet because this should be a joyous experience to help someone who helped you. It should also go on your time sheets. Other Redditors suggesting lunch are onto something too. It isn't all work - it is also relationships.

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geekjitsu@reddit

If he’s calling you at work, why are you put off by it?

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Jaereth@reddit

> I feel like I owe the guy a lot. He's always been extremely appreciative of my work which I value more than almost anything else because it hasn't always been the case in my career. The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures). He's friends with all the other execs (some of whom I have done some side work for) and I will be seeing him at company social events for as long as I'm here. Just help the guy. He deserves it. I wouldn't do it on my personal time, but if you're on work time then that's ok. Be honest about your time spent on him and if another exec makes you stop - then the heat is on them. But i'd help a guy like that till the day I die.

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MarkTwainsSpittoon@reddit

Why does it need to be transactional? Why can’t kindness just be the reason why?

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PartyDuck7756@reddit

It'll tune down in a bit. He's probably on top of everything now he doesn't have to attend a dayjob anymore.

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Additional-Grade3221@reddit

You described some of my former bosses and I still will go out of my way to help them when they need it if I have time

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Glad-Basket-2186@reddit

Can you somehow delegate the work politely? Otherwise this just sounds like a person wanting friendship/company.

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509BandwidthLimit@reddit

Help once, see how well the pay (or tip) is, then decide future requests.

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Pathfinder_Dan@reddit

Who you know is a big deal. Keep the old boy close, and stay friendly. If you think he did right by you, do right by him whenever you can.

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Spanky_Simeon@reddit

Without a doubt, help him. He's helped you and will likely do so again

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CalvinsStuffedTiger@reddit

Don’t be a dick, help a friend out

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coachmagurk@reddit

Bite that bullet. It’d be bad form to kick him to the curb.

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Ok_Education_2753@reddit

Help him graciously, but don’t go extra out of your way to drop everything. You’re building good karma and someday you might need something, and you won’t feel bad asking for a favor.

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No-Card2461@reddit

He may be retired, but that doesn't mean he doesn't have reach and influence in the company. He seems like he was good to you, help him out.

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FoundationCareful662@reddit

He is just socially hungry and missing that part of work. He’ll figure it out. Give him some time

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GoodWin7889@reddit

He was good to you and treated you well when he was running the company. It sounds like he developed a type of friendship with you. He still has tremendous pull at your company. Meet him for lunch or fix his tech but don’t blow him off because that will bite you in the bottom.

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unbelievablygeneric@reddit

Your his go to guy. That is a great thing to be. And being that you can handle these issues for him (which he struggles with) he most likely sees you as highly competent. Partner that with the fact that his opinion matters at this company, he may see bigger things for you in the future. Bite that bullet hard son.

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Nissir@reddit

Been in the exact same situation. On the plus side it landed me a job later on. Guy sounds like he treated you well at least might as well pass it on.

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theducker@reddit

Being on friendly terms with someone who very likely has powerful friends both in this company and other companies seems to be well worth the hassle of doing a little tech support

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rottknockers@reddit

Why would you? You burn a lot of bridges?

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Trickstir@reddit

If you want a village, you have to be a villager.

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keep-on-drawing@reddit

He helped you with all those things so be nice to him, help him with whatever he needs and do not ask anything in return and you will reap whatever rewards are coming at you. He sounds like a really nice guy, keep that friendship alive.

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ShadowCaster0476@reddit

Just remember that if you help him, You will also be personally on the hook if his device/network/whatever gets compromised. Not saying no, just be aware of the potential downside.

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OuchCharlie25@reddit

Tell him you’re setting up a tech support side business and you’d be happy to help him off the clock. He’ll respect you for that.

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the4thbandit@reddit

Sounds like good relationship to cultivate. Who know what other opportunities could come along

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Electrical_Cook_3100@reddit

Ask for something, you either get paid or he will stop

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I_compleat_me@reddit

Sounds like an excellent time to start a consulting business. I think you found your first client.

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IsabelleMauvaise@reddit

It's not clear from your post if you are male or female, ages, relationship statuses, and whether you're picking up an attraction vibe. I would not go to his home regardless; do it via Teams. But, this guy may be able to help you advance in your career either in this company or elsewhere and with advice. He may not know what to do with himself now that he's retired, and these requests are either an oblique way to stay connected or maybe a come-on now that he's not in the same workplace as you. Decline any personal kind of meeting like lunch or drinks. He was exceptionally good to you. Like once in a lifetime of working. I worked for one company like that, that I loved and they loved me. It was life-changing. He liked you and valued you in the way it counts, money. Not the amount, but you were worth it to him. I'd help him out a little and keep it on whatever terms you are comfortable with. You're actually in control now, not him. You can return the generosity you received, at least for a while, on your terms. Set specific appointments; keep them relatively brief. I don't think it will go on that long.

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JairJy@reddit

Keep helping him, but start asking for favors too.

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3BlindMice1@reddit

Help him out, ask him for something small in return, that way neither of you feels weird or feels any resentment. Like old school old man friend rules. Seems like you're thinking way too much about this, your buddy asked you for a favor, tell him you want a few beers next time or something

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Goodthrust_8@reddit

Sounds like a buddy of sorts. I'd bless my lucky stars and continue to assist providing it doesn't fester into something larger.

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MIS_Gurus@reddit

The easiest and safest way is too slowly start responding slower and slower to the requests. He will end up finding another option and you do not burn the bridge. If he ask why it takes so long just politely let him know you are swamped and you are getting to his requests as quickly as possible. If he calls don't answer let is go to voicemail. Always return the call but take longer and longer to do it. If he texts you do the same thing. The slow roll always works.

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osbornje1012@reddit

Just Do It. Sounds like like he will pay you in some manner for your assistance.

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Sometimesunaware@reddit

I'd be up on his roof cleaning his gutters in a rainstorm if he called at midnight, this man is at very least your friend, don't burn him.

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RayEd29@reddit

So let me get this straight, the founder/CEO that has solidly had your back the entire time you've worked at this company just retired and you're 'tired' of helping him with his tech? You say you feel like you owe this guy a lot and in the same breath try to worm your way out of giving him anything - make up your mind. If you do owe him (and I think you do), answer his tech questions with a smile and count yourself getting the biggest bargain of your life. Your last paragraph says more about you than it does the retired CEO. Helping out the man that has made your life what it is amounts to 'biting the bullet and accepting you will HAVE to help him with shit' - sounds like a staggeringly ungrateful attitude you have there.

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TheTangoFox@reddit

Treat him like a friend and mentor

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TheAsianTroll@reddit

Do you know how many of us would kill for this opportunity? Have an amazing boss who makes damn sure im well taken care of, in exchange for the odd favor IN A FIELD IM PROFICIENT IN? Dude, im a mechanic, and if a rich guy who made sure I was set for 5 years asked me to change his oil or fix his car, you bet your ass id say yes. You were getting FIVE FIGURE checks as BONUSES. You got HUGE raises and promotions with zero pushback. Is he really asking too much of you, man? Hes coming to you because its YOU. He values YOU and your skills. Five years, he took care of you, and youre complaining about a small amount of work for what hes done. This is a very rare case of loyalty between employee and employer that practically doesnt exist anymore.

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-_-dont-smile@reddit

He can be your friend or connection. Relationship needs work. You help him, at some point he helps you. Even if he is retired. Maybe even more so, given that now there is no conflict of interest to think about.

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GoodLyfe42@reddit

I would not burn that bridge. The help you are doing could help you in so many ways in the future. If possible even see if you could get coffee or lunch with him for career advice. You are possibly sitting on a gold mine of advice and connections

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Full-Possibility-190@reddit

As others have stated, you are not “biting the bullet”. Invite karma into your life… have patience and show gratitude. Sounds like he supported your growth for a long time. If you ask anything in return, make it his advice as you chase your dreams.

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Meet8567@reddit

I’m in a similar situation. I kept in touch with the dude and we have become friends. Funny you should mention personal tech support because my old friend is helpless too. 😊

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redwbl@reddit

If I was in your position, I think I would continue to help him out, but would start subtly joking with him about your fees and that you are keeping track. Maybe he’ll throw you a bone occasionally or he’ll get the hint and realize he shouldn’t abuse it. Keep it lite, but sounds like a guy that helped you out and was pretty fair, I’d have a hard time not giving him an hour out of my time now and then.

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1MStudio@reddit

Nah no longer your CEO…stop it…just stop it…you think if you left your job, and reached back out and was like “hey, think I could just get paid for 2 weeks..I’m really Down on my luck rn” you think they’d be like “oh man, this guy was loyal.. let’s just cut a check for him” Fuuuuck no. Tell him you’ll charge him the going rate of $150/hr minimum of 1hr pay with a $50 consulting fee per contract. Send him a contract. And let it go. You don’t owe that guy anything..

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doubleyewdee@reddit

Absolutely hang on to that connection. If you find yourself doing many hours of work for him weekly (like 10+/week), start treating it more as contract work. Make a list with him, figure out what he needs, maybe gently steer him to realizing the time value as well, and you're fairly likely to get paid for whatever tech help you're giving. Even if not, connections are good, especially in that tier of people with "f you" type retirement money since they tend to run in the same circles.

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AbedSalam1988@reddit

definitely worth it OP. it’s good to have powerful and rich connections trust me.

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Straight_Story31@reddit

Nice humblebrag. Seems like a lord worth serving. Good fortune to you.

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bradland@reddit

Let’s just ignore how much he’s already helped you for a second and focus on how you could benefit from this situation. It never hurts to have a former CEO in your network. I would cultivate this relationship, and do what you can to keep it going. If he relies on you, that means he trusts you. That says a lot. You never know when you’re gonna find yourself looking for another job. CEOs tend to be very well connected people, and that kind of referral is something that few people have. As they say, it’s not what you know, but who you know. Don’t squander this one.

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pdxwestside@reddit

Dude what a great way to help him out. He probably still has a lot of wisdom you can learn from. Any being nice feels good.

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frankingeneral@reddit

I think you should just bite the bullet if he means that much to you and has done that much for you. If the requests get to be unwieldy and time-consuming, then it might be time to set some boundaries. But if it's just the occasional 5 minute phone call to help him figure something out, it is what it is. Also a good excuse to stay in touch with someone you seem to like, or at the very least appreciate.

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Violentopinion@reddit

Life is all about connections. Sounds like he’s a good friend.

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Dominicwriter@reddit

Bite the bullet - sounds like someone you need on your side.

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LostWoodsInTheField@reddit

Decide how you want to go forward for off the clock time but go to the highest boss you can and verify they are ok with you doing tech support for the founder during business hours. You are likely to find them saying it's ok. Frame it as a 'I'm fine doing this but I don't want to lose my job if I keep doing it'.

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Sheila_Monarch@reddit

Just help him. For all you know he’s still a major owner or chairman of the board. Most founder/CEOs don’t retire from that position without still maintaining a huge foothold in the company. Meaning you still work for him, he’s just in a different position.

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splurgesplatoon@reddit

If saying no = burning a bridge... Then I say burn that motherfucking bridge... If the 'bridge' comes with conditions you aren't happy with/willing to comply with... Then is it worth it?

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FirstmateJibbs@reddit

Bruh, how much he’s helped you and your life. And you can’t stomach occasionally helping him with very small, menial tasks? What kind of person are you?

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Affectionate-Yam7454@reddit

Bite the bullet. He seems like a keeper. Plus, retired people still have their connections.

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Visual-Citron8387@reddit

Bite the bullet. If he's been as good to you as you say he's been, just help the guy out when he needs it. Realistically, how often can these sorts of thing come up? And how long do they really take? He's probably just settling into retirement, is bored, doesn't know how to handle not having anything to do. It can take a little while for folks to acclimate to the retired life, but they eventually do. As long as it's just personal technical issues and not a new business, I would advise simply enduring it until it peeters out (which it will). Is it annoying? Sure...

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falco_iii@reddit

I was going to say that it might be worthwhile asking him for money, but after reading all of it, it sounds like he is definately an advocate for you and could be a friend and I would not suggest asking for money. As an advocate, would it be useful to have a retired powerful person that you do IT for so you can ask a favor for later? As a friend, what would you say to a similar level of friend (without the CEO/company stuff) that frequently asked you for IT help?

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AltruisticCamp8775@reddit

OP seems to be a shit person, ngl.

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Varabela@reddit

From what you wrote about what he’s done for you….You f*cking owe him. Once a week for 15-20 mins is nothing. Plus he probably likes keeping I touch with you. Also, the guy will be connected should you ever need any favours. Keep yourself in credit in the favour bank

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Catripruo@reddit

If you say no - bridge is burned. I don’t think ever6 interaction has to be transactional. He was good to you. Your turn.

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Sea_Air9837@reddit

Yes, you’re stuck with him.

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lilred7879@reddit

Just do it - we have former CEO's and even just well like management that we support from time to time. In our case anyway these are not people who are trying to take advantage and would pay if we asked them to BUT as you indicated a lot of people owe their livelihood to them so we take care of them. Heck we even had one that turned around and ended up supporting one of our OLD systems for us after he retired just to keep himself active.

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bigreddadbod@reddit

You dont owe him anything unless it makes you happy to do so. After you’ve done this a few times, just tell him that it’ll take you a while to help the next time it comes up. And keep making the “a while” longer and longer. My father in law has been retired for 10 years and still goes to the IT team for computer help. He thinks it’s completely reasonable too. He’ll never stop. This is your future if you don’t say something or just deny at some point.

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The-Senate-Palpy@reddit

Hes been good to you? Be good to him. If he abuses that privilege its one thing, but what you call "biting the bullet" most people call being a good friend

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ebullientdoll_@reddit

If it were me….id be at his beck and call LMAO

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SignalSegmentV@reddit

Why not invite him to lunch? Seems like a chill guy to hang out with. Otherwise, as others have said it, it’s your call.

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heapsp@reddit

The world is built on favors from people. Don't be afraid to ask something of him in the future within reason and continue to help him out.

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Thewrldisntenough@reddit

As far as my experience with CEOs go, yeah thats a little annoying but Id absolutely just role with it given all the things you listed that I absolutely never gotten out of a job.

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Big-Explanation4919@reddit

Bite the bullet.

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Fineous40@reddit

Do it on company time. If the company asks where you were at, tell them.

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MathTeachinFool@reddit

This would be my suggestion as well.

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tyrnill@reddit

Oh man, I came in here ready to start swinging for you, but I kinda hope you keep helping him out? Call me easy, but one single 5-figure bonus check and I'd be going over to turn his computer off and on for him any time he asked.

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Phobic-window@reddit

Make your assistance just a little bit more inconvenient every week. Like tell him you will help, but take a little longer to get to it, have things start coming up and need to postpone the help till tomorrow. He will adapt, but always be very willing to help and excited to do so

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Raven_of_Blades@reddit

So you made a great connection and you wanna burn it because you can't help the guy once a week with a small quick matter? People would die for this kind of connection, are you stupid?

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ninjaluvr@reddit

Sounds like the guy really looked out for you. Personally, I'd return the favor and help him out some. But if you can't stomach that, just be direct. "I really don't have the time outside of work to help you. Thanks for everything you did for me though."

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GeneralDebate@reddit

And there goes that bridge

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volitive@reddit

💯 Don't burn this OP.

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MiserablePotato1147@reddit

🔥🔥🌉🔥🔥

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The_Freshmaker@reddit

Lmao don't say that. Just help the dude. Our 'retired' CEO still is constantly at our office, gives speeches at the big meetings every year. Often times those guys are just retiring from the day-to-day but they're definitely part of the company still and you should absolutely treat them like they are.

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ninjaluvr@reddit

That's what I said. You may notice the "But if you can't stomach that..." part. If OP can't find it in themselves to help, just burn the bridge and don't pretend to care.

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Taconnosseur@reddit

Why is it so hard to be thankful?

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stufforstuff@reddit

Don't be so stingy - especially to people that gave you 5 figure bonus checks - geesh, some of the people here think that IT skills are the gift of the gods to be dribbled out ONLY while on the clock and ONLY from 9-5.

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Khuntastic@reddit

This is crazy it seems like a no brained to help this guy out once in a while. It seems like you guys have a closer relationship than just boss and employee I think he sees you as a friend

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Opposite-Tiger-9291@reddit

I would suggest that you start delaying your replies to him for longer and longer, so each time he texts you or emails you, you wait longer. It should soon become apparent to him that you are not on call for him and that you do not feel like you are on call for him, and he should naturally move on. If he tries to increase the urgency, just be calm and don't reply until you are ready to reply. If he confronts you about it, you could ask him if he would like to set up a payment system for offering your IT services. This is a tiered approach.

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MrRoboto1984@reddit

His name is on the building…. He gave you raises and bonuses. Man I wonder what a reference from that guy would do for your career. This is an amazing network contact. Don’t burn that bridge, dork!

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nalaloveslumpy@reddit

This is the point where you make a proposal. Offer to be his personal tech support for your currently salary plus benefits and copius PTO. He'll get the point once you make it a business transaction. Then immediately follow up with an invite for something social.

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Gators1992@reddit

I guess if you don't just want to do it because you like the guy, at least look at it as an opportunity. Maybe they are taking advantage of you to some extent, but also seem to have done right by you. And staying in good standing with the execs never hurts your career.

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MrsMayhem56@reddit

Inconvenience is the price of community.

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MrCharmingTaintman@reddit

I’d say help him out when you have time/the mental capacity. If you don’t, just be honest why you can’t at that time but offer to help when you’re free. If you want to.

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Kind_Substance_2865@reddit

Has he abused the privilege by demanding you come help at 3am? Or does he wait patiently until you can fit him in? Based on other things he’s done for you, it doesn’t sound like he’ll be an entitled jerk about it, so I’d help him whenever you can. If it comes to a point where you have to prioritise stuff in your personal life, he’d probably understand.

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mysterytoy2@reddit

You never say no to a person like.

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alwaysreadthename@reddit

So he made you middle-class rich but you can’t help with with iPad and laptop tech support? Jesus Christ, man.

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wcvince@reddit

If someone gave me 5 figure bonuses the least I could do is simple troubleshooting for him.

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mtraven23@reddit

link him to this post

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MJCExperience@reddit

The guy trusts you, and I bet he knows how to do some of the stuff, but he isnt sure how to just be friends with a past coworker. Just help the guy out, you never know what he actually has going on and something easy like this once in a blue moon might be what he needs after retirement. Plus, I would bet that you doing this looks good in the others eyes as well.

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sockalicious@reddit

This is not work, and you should not look at it as work. This is a guy who no longer has any organic reason to keep in touch with you but wants to keep in touch with you, so he has invented one. If you value his contribution to your life as you say, you should embrace this opportunity to stay connected. Just my $0.02.

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Smooth-Reference3140@reddit

Setup that ai thing gilfoyle had in silicon valley

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adamsquishy@reddit

I’d say he’s earned some leeway to tech support in his post retirement days, but there’s nothing wrong with setting boundaries on your time. If there’s a request which would conflict with something else you’re working on or have planned then let him know you’re busy but would be happy to help at another time/date

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G305_Enjoyer@reddit

I help retired vips, just only on the clock lol. Current leadership doesn't like it (blames retired, not me) but I keep them generally aware of the requests coming in.

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Laslomas@reddit

If the guy was good to you, treated you well, gave you a chance, you should want to do right by him- retired or not.

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tnmoo@reddit

Definitely would not say no to such a resource like a CEO who can help you further your career with a reference in the future! Are you kidding me?

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athamders@reddit

A golden goose is plucking at my hand, do I slay it?

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chibob11@reddit

He may be retired but do you know if he still has equity in the business? You might still be working for him without knowing it so I would tread carefully.

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OneOfAKind2@reddit

Sounds like he was a great and generous boss. I wouldn't think twice about helping him in perpetuity.

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AZdesertpir8@reddit

Honestly, see if he will pay by the hour for services rendered. He values your services, so might be a nice side gig, and keeps you from burning the bridge. Ive done this myself in the past and it worked out really well.

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trisul-108@reddit

>I feel like I owe the guy a lot. That's not feeling I get from your questions. He gave you raises, promoted you and rewarded you. However, you don't feel that you owe him anything, you are asking whether it is safe to say "No". You're not saying "he's a nice guy", "I like helping him" etc. To you, it's all completely transactional, he was good for you, you want do cut him off, but you are afraid of consequences.

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Hefty-Amoeba5707@reddit

If he calls once a week for 20 minutes, that is roughly 17 hours a year. Given the five-figure bonuses, the truck, and the career capital he gave you, this might be a tax worth paying. Especially if he still has leverage on the company. However, if it is disrupting your work or personal life, you need to transition him without making him feel rejected. You could "drag your feet", you could play the liability card (personal vs company) is a different ballgame.

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ReplyOk6720@reddit

Cost benefit wise, the once a week help seems like a necessary sacrifice. After 5 years, re assess.

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jcdoe@reddit

Or just fix the guy’s computer. Y’all talking like you’re reevaluating a contract and not doing a favor for the guy who started OP’s career and was extraordinarily generous (5 figure Christmas bonuses for IT?). Just fix the damn computer. Or iPad. Who cares? Be generous, this guy was a real one.

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kozak_@reddit

Yeah, at least 10k bonus? I've never had any like that and I'm in corporate for 15 years

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Tax_Evasion_Savant@reddit

that just means the company is doing extremely well.

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jcdoe@reddit

I never got commission checks for that much! But yeah, the owner is a dick for wanting OP to spend 20 minutes fixing his iPad and throwing money at him for it

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ReplyOk6720@reddit

True.

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Tax_Evasion_Savant@reddit

> Given the five-figure bonuses, the truck, and the career capital he gave you OP earned those, the CEO is just the gatekeeper.

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AvoidingBansLOL@reddit

As someone who has benefited greatly from making connections like you have with your retired CEO, I'd recommend you continue to maintain a good relationship with him. People like that never truly retire. You help him with stupid little shit like his iPad or phone and he can still toss your name out to people in high places and help further your career.

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curious_as_frick@reddit

Bite the bullet. Think about all you just wrote. Men like that are never not in the company even when retired. Make it so that he goes to his grave thinking he made the right decision with you.

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ThatDjAWK@reddit

Sounds like he’s your pal. Do what you can when you can, communicate if you are overwhelmed with work/family if you need a break but sounds like he’s been solid for you in the past. Also sidenote: you could ask him for favors in the future without feeling bad, so all in all sounds like a good deal.

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SuperBathMan@reddit

I love that all the solutions are " just be friends with the guy" lol

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Far_Pollution_5120@reddit

What? Why would you not want to keep in touch and stay friends with him? He'll be a great reference in the future, and he probably has a lot to teach you even now.

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JxCam@reddit

Please please please listen to everyone and help him out whenever he asks. Sounds like an awesome person

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IttsssTonyTiiiimme@reddit

Dude? This guy is clearly a good connection. Don’t drop what you’re doing to help him, but help him. My brain is going to golf outings.

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Floppydiskpornking@reddit

OP sound like a dick that dont deserve such a good connection

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Top_Sheepherder_5167@reddit

OP sounds fake. If helping someone that got you multiple raises over the span of five years, no question promotion, and huge bonuses is anything other than a no brainer...

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reenact12321@reddit

To add to the conversation, I say you help him and be gracious based on your prior relationship. What changes I think is you have the right to set limits. You helping him doesn't mean you have to jump to attention every time he calls like you did when he was CEO. "Hey Bob, would love to help you with that (once I'm back from vacation/work slows down just a bit/I'm taking care of some family stuff). Set boundaries just like you would with a good friend who may not realize how much they're asking of you .

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Educational_Case_134@reddit

Even though he retired he may still be on the board and have influence within the industry. I would continue to assist as your schedule allows.

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NonMaga@reddit

If you don't see this person as a friend, look at the time as an investment. This person can be an introduction to a lot of potential people. Should you ever lose your job, this person would have the resources to assist. I'm not saying be a doormat, but he's also trying to find footing as a newly retired person. Sounds like he'd like to spend more time with you. Perhaps he has an opportunity for you?

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Ok_Astronomer_8667@reddit

Be his friend. There’s this notion I see a lot, mostly online, that co-workers should never ever be treated like normal people in your life. It’s essentially a dehumanization of people, under this idea that you are just there for money, not relationships. But at the end of the day we’re all just people. And you spend a lot of time with your colleagues. It’s really not that big of a stretch to say that, if someone clearly treated you well and was super nice at work, they could also be a great person outside of work.

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RhodyViaWIClamDigger@reddit

Schedule tech sessions over lunch at a restaurant of your choice, on him. Try new places; visit old places - you have more to gain from maintaining this relationship than he does.

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Old-Classic-1981@reddit

You sound like ama dick for not wanting to help for someone you need to be grateful. Imagine your career without him and answer your own question.

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One-Consequence-4130@reddit

bro come on I think the guy earned a lil tech support

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Various-Emergency-91@reddit

Sounds like someone you want on your side to me, unless you just cant deal with it I'd suck it up and fix his iPad.

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old--oak@reddit

Do not bite the hand that feeds you! Retired or not I bet he could still ruin and make a career in one phone call, this is a guy you want in your corner.

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lol_alex@reddit

Dude I gotta do this for my mom, and she doesn‘t even pay me… and he seems genuinely fond of/ appreciative of you. And just a thought: Maybe the guy just wants to stay in contact, hear the inside news, because he‘s having a hard time with retirement? Many founders do. Maybe he could solve those problems himself. Maybe he‘ll put in a good word for you with the new management, or stop them from doing idiotic stuff like outsourcing your job to India.

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Sappledip@reddit

If you didn’t already know the answer by the time you finished typing out everything this dude has done for you then idk what else to add here lol

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Top_Sheepherder_5167@reddit

Multiple raises over the span of five years, no question promotion, huge bonuses... and setting up an ipad is drawing the line? Fake

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Aggressive_Bill_2822@reddit

I’d stay friends forever lol sounds like a really good person and just thinks of you as a friend.

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thorleywinston@reddit

Unless it interferes with your duties or he asks you to do something that you think might get you in trouble, why would you stop helping him? He's done things for you when he was your boss and he's got pull with the current leadership so regardless of his current title, he's a good friend to have in your corner.

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VoiceBeyondTheVeil@reddit

I won’t provide tech support for family members let alone friends or coworkers.

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jo10001110101@reddit

He gave you 5 figure bonuses, and you can't be assed to help him with is ipad? lol

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PatrioticPariah@reddit

He sounds like a friend who has bent over backwards to help you. What he is doing, is nothing by comparison. Dude, be cool.

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Local_Educator_1646@reddit

I would suggest helping him whenever he needs it. Look at it as a good deed more than anything. Don’t burn that positive bridge as it could lead to future opps.

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Library_IT_guy@reddit

For most people, I'd tell them to piss off - I don't do IT work outside of work. But This guy sounds like a friend and a worthy person to spend a little time helping now and then. I've got people like this in my life. A co-worker that is part mechanic, part handyman, and all around just a really nice guy. He has lots of skills that I don't. We always help one another when needed. That kind of friend is worth helping. In your case, doubly so since he's responsible for your livelihood and was a great boss to you.

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marcus_789skid@reddit

You never know when you might need a favor. Sounds like a good friend to have

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Rykmigrundt90@reddit

Dude, he sounds chill AF. Help him out. Go grab some lunch or something eventually and talk for a few hours to catch up. Sounds like a decent human being. We need those.

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LawyerDad1981@reddit

Bite that bullet. Hard. Sounds like he was a fantastic CEO, a good guy, and your kindness will come back to you.

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eggofthemoon@reddit

Nah give him my #, ill do tech support for him instead

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Joni-Balogna@reddit

Seems like a standup guy that you are appreciative of, so I am curious why you want to say no. Sounds like he might be a good person to keep in touch with even just for your own benefit! Is it taking up a lot of time from your normal workday? Is he calling at really inconvenient times? Do you think this will go on indefinitely and you actually want to end the friendship? I would keep helping him and be friendly, but assuming you must stop this for whatever reason, the next time he calls let him know that you cannot help him at that moment, but schedule a time to help him, preferably in person. When you meet with him in person, help him with his tech problems and ask him if he is having any other tech issues you can help with. After that you can tell him that you noticed since he retired that he reaches out to you about once a week and you were wondering if he was just looking for a reason to stay in touch or if he really needs lots of tech support. If he really needs lots of tech support, you could refer him to a tech support service. Let him know that you’re afraid that you might not always be available when he calls and you want him to have that resource. You should do the decent thing by being honest and fairly direct with him that you can’t help on a weekly basis, but by referring him to a service hopefully he will understand your “hint” and you won’t hurt his feelings. If he is just trying to stay in touch, then his weekly tech calls should stop and you can tell him he doesn’t need an excuse to contact you :)

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omnes1lere@reddit

Saying no is burning a bridge. There's no way around that.

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Iusedthistocomment@reddit

I think I'd help him out a couple of times and at some point drop a "Haha if you need my help this bad you should hire me as your freelance IT guy hehehe" And see if he'd be willing to pay for your skills instead of cutting out contact dntierly

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slackerdc@reddit

Something tells me you should be his personal tech at his beck and call. Normally I'd say no get a support contract drafted, but this feels like this will lead to something if you keep doing it. Like a check with a lot of zeros type something...

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Careless_Historian28@reddit

You could also occasionally be “out of town” or unavailable and delay the help by a week or two to kind of gently week him off if you want to.

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EnviroLife69@reddit

Never burn a bridge. The connections and network he has will help you in the future. Imagine you need to leave and decide to give him a call to get his advice, he sounds like the type to set you up with a buddys company without a doubt. Never bite the hand that literally fed and provided the money for the food.

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EndOfTheRoad_777@reddit

I have a client, their lead IT guy was the lead IT guy at the owners previous company. The owner is a billionaire who retired and then started a vanity project and brought his guy over. He took care of him... Don't burn the bridge.

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DiamondCutt3r@reddit

Are you on the clock?

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shizzaff@reddit

You want a guy like this on your side

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sukaibontaru@reddit

That’s what networking is.

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ironbeagle99@reddit

I had my former CEO as a referral on my resume for my current job. New company had their jaws on the floor when they called him and he actually picked up. I think it’s worth it.

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VegetableLie1282@reddit

This idea of boundaries is going too far. We are humans, social animals and we need each other. Boundaries are for when you are mistreated or in a toxic dynamic. Not everything has to be tit for tat but even if it were, seems like you've gotten lots of tit and might owe a lot of tat. Possibly a lifetime of tat! And unless it takes huge amounts of your time you smile and tat right back!

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Shellmarcpl@reddit

I'm willing to bet that he'll pay you especially around the holidays and such from your description.

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optintolife@reddit

Dude continue being friends. Literally a mentor who will continue opening doors. It’s helping a person, no longer company work.

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shelbyrobinson@reddit

IDK, I know a wealthy old guy that asks me on occasion to help with his computer problems. I've done it so many times and never taken payment despite his offers. But he's given me some nice things over the years so I don't mind. Of late though he needed me immediately and I just couldn't do it. Now he isn't asking anymore so...

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GamingGamerGames_@reddit

Change your phone number. Or block his number so you stop seeing messages or phone calls.

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spyder7699@reddit

Did he become a CEO by doing things for free? Probably not. Do the work, ask current bosses how to bill. He scratched your back because of work you did that made him money. Quid pro quo. It's not personal, it's business.

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BenitoCameloU@reddit

I don’t know man, he seems like a friend and genuine boss/CEO so it might not be clever to burn that bridge.

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123shipping@reddit

Sounds like he is talking to you as a friend and not as an employee and was a mentor of sort.

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burnafterreading999@reddit

Why is helping someone who has helped your career and could help you further such a bad thing?

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Toadsted@reddit

I mean, are we talking every day, every week, every month? I've kept in contact with a past coworker and even helped them as a reference for a new job. SonI guess it depends on how much you appreciate their help, and how much you think was just work related. If you're concerned of burning bridges, it sounds more greedy than setting altruistic boundaries. So then it's like having them still keeping your job, you just have to deal with it.

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KapnKrunch420@reddit

Consider he still has connections you should maintain a healthy relationship for your own sake! He could probably sink you if he wanted.

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Tsiox@reddit

Most IT people aren't really intelligent when it comes to politics, and sometimes it has to be spelled out. In your case, you'll be much better off helping him if it's just IT questions and a occasional tech support.

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psyclembs@reddit

When someone always has my back, I always have theirs.

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MattGarcia9480@reddit

Seems like a good ceo and seems like hes thinking of you as a buddy. Have pizza and beer or something occasionally with him unless hes a nightmare to hang out with. People are people and sometimes high ranking roles doesn't mean anything to the person, thats just their role. Id go out to eat with the owner at one company I worked for but him and his wife treated us few staff as family. I am buddies with his kids. The father is a billionaire but he don't act like his shit dont stink. He worked fuckin hard for his money and to have a successful company. I haven't seen them in over a decade but still get good references from their company. The kids live in Norway and was actually saying they need help and would love me to join and move out there. I am a family person and couldn't do it. My family is aging so fast.

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keysercade@reddit

Each time you help is a time investment in his further support of you, you are the only one that can determine that balance.

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whoo-datt@reddit

Consider also what he can/might do for you in the future, re. referrals or mentioning your name for lucrative openings....

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MaizeNBlueWaffle@reddit

You can refer him to the Apple Genius bar for some of this stuff like iPad and I assume his computer

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Ok-Comedian-2972@reddit

When he starts his new business - you’re top of the list. And that’s the train you want to be on and have a piece of.

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EndStorm@reddit

Should go grab a beer or a meal instead. Sounds like a good dude.

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Leading_Bag5689@reddit

I have a friend like that (my professor whom I worked for during university and in a startup). He is retired and I am working in another company now. The relationship developed into a mentor-mentee situation, where I help him every now and then, and we discuss markets and so on together. Whenever I needed help from him to get a new job, he always supported me and volunteered as reference. I'd keep an open mind and help out the old guy.

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stormblessed27_@reddit

Dude. Be a friend. It sounds like you got along great with him. Idk I tend to maintain good working relationships. Chief creative officer at my last job was such an amazing guy to work for, was always in our (designers) corner and really gave a shit about is. I was so bummed when he left that I randomly hit him up to grab drinks. A tradition we hold once a month. After a layoff, he hooked me the fuck up with a crazy good gig. Dude went to bat for me. I don’t even refer to him as my former boss anymore, dude is just a good friend. Grab beers with the guy man.

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AvengingBlowfish@reddit

I have a similar situation. I go along with it, but you have to set boundaries. No house calls and no calls outside of work hours. If he has a tech issue, he needs to bring the device into the office and if it isn't something I can fix in 5 minutes, I just tell him to get a new one.

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The_High_and_The_Low@reddit

Sheiiiiiit if he’s asking YOU out of anyone else for help then that’s something to admire and appreciate. Especially if he was the CEO

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RedditNotFreeSpeech@reddit

If it's not super burdensome you keep helping him. You've obviously made an impression on him and this is the type of guy you want in case of emergency.

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AnnieLovesTech@reddit

He wasn't your CEO. He was your friend. And it sounds like a friend we could all use.

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PanicSwtchd@reddit

Does this actually cost you anything other than some time? This guy seems to have treated you well oveer the years and has given you tons of upward mobility. If he's not being rude or mean and asks you for help occasionally, I don't see why it's bad thing to keep the relationship open. Retired CEO's still have networks of people and if things go sideways at the company, you haave someone who will likely be happy to put in a good word for you elsewhere later.

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stiggley@reddit

Schedule a "monthly" (or weekly, or whatever time period you agree on) IT visit to sort out his issues, and give him some guidance on doing it himself - or ask him to pop into the office when he's visiting and you can see what you can do for him them.

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mcon96@reddit

Wtf are these late stage capitalism poisoned replies? This sub is weird

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GitmoGrrl1@reddit

Ask him if his time is worth money. When he says yes, tell him your time is also worth money.

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OuterDorkistan@reddit

Is it really that big of a problem? The man has done a lot for you. Are you really that petty? I can almost guarantee if you cut him you will regret it.

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FrightfulPumpkin@reddit

I’ve absolutely helped people with annoying things for less than 5 figure Christmas bonuses. Community requires that people help each other out when it’s annoying. Building community is worth it. You help not only other people but yourself.

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Salt_Weakness_1538@reddit

Think of it as easy networking. You have a straight line to the company’s founder. Not everyone gets that. I get it, it can be annoying, but this is like finding a $5 bill on the ground.

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CCC_OOO@reddit

Yes just keep helping your guardian Angel for at least a year. He feels supported and appreciated and you don’t burn a bridge. Be the first one to reach out sometimes especially as it relates to your career, share good news then as your career grows in the future it’s more of a gradual and obvious shift since your responsibilities are growing you will be less available. If you are legitimately too busy at times it’s ok to say hey I am going to be busy until Thursday but if you still need my help then please let me know. Now you have replied promptly, given a timeframe you could possibly help and have put it back on him so that he would have to reach out again for that help.

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dartanyn@reddit

Next request...Either ask him if he has any ways of essentially putting in a good word for you at the current company so you might get a raise, or better raise. Or if you really don't want to have to keep being his IT guy, tell him you don't mind helping him out here and there, but that your time away from your work is valuable to you so you hope he understands if you aren't always available to help out. (or tell him you'll have to start charging him for your time and either quote a friend rate that he'd likely pay so you both win a little, or quote him a "f.u." rate that he likely won't want to pay, but if he does it makes it super worth your time).

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SuspiciousCustomer@reddit

Brother... Treat this relationship as the golden chance it is. This guy still knows everyone in the C.-suite at your firm. Hell, he probably has connections up the wazoo. Spend time with him, maybe grab some mentoring, next time he calls you up, show up with a couple drinks and help him out and shoot some shit. This could become a friendship to last you a lifetime and set you up for success

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HeatPoliceOpenUp@reddit

Guy did his best to be your friend despite being your boss and you are thinking about whether or not he's wasting your time with a relationship that he absolutely does not need with the massive connections he has. Talk about looking at the world through the bottom of a well. You don't deserve this guy at all.

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ThinConnection8191@reddit

I could do if I have time. He sounds like a man I want to be around with and has helped a lot. Just say no if you are in middle of something

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Alzeric@reddit

Well certainly sounds like he's went above and beyond for you, I don't see the issue with you returning the favor. Especially if he's recently retired, it may take him a bit to acclimate to Non-Work life. Should make you feel good, you're his GO TO and he immediately thought of you to help him.

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More-Bison-8570@reddit

I think this type of mindset is exactly what’s wrong with the world. Nowadays, you had no problem taking from this man. Whether it was a raise, bonus checks, whatever. But when this man is asking something back from you, you question whether you should give anything back. The whole world nowadays is take take take and very little give. Be better, seems this type of person deserves it.

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nestersan@reddit

Bite the fucking bullet

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Robdog421@reddit

i just wonder what this comment section would be saying if this guy wasn’t a CEO. if you’re doing something you don’t want to be doing, then don’t do it. of course you’ve got to show up for your friends, so if you consider him a friend then keep doing your thing because it’s important to show up for friends. if you’re only doing this to have a potentially good connection then fuck that, go live and make your own life.

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kawaiian@reddit

Hmmm.. he might be calling for help on things he can probably figure out because retirement is lonely and you struggle to find purpose. You’re doing him a great favor to help. If it becomes too often, you can offer, “Let me help you hire an assistant so we can just be drinking buddies”

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Redqueenhypo@reddit

Strange old people are potentially the strongest and most powerful friends you’ll ever have. Be nice to the lonely bloke, if not out of gratitude (which it seems you ought to have), then because it could help you a lot.

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North-Flower-5963@reddit

Wow you’re kind if a dick lol. If you don’t want to help at least find someone who can and refer him to them, tell them to refer to them moving forwards

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bluesky34@reddit

Be polite and helpful but fit the work into your schedule as it suits you, so the response time isn't immediate and it's convenient for you.

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Equivalent_Mine_1827@reddit

I know our work is very valuable, but sometimes, it's good to help people for "free". One of the comments said it, social currency is worth it. My often help my brother, because he often gives me gifts out of nowhere.

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Competitive_Touch_86@reddit

Depends on how crazy the requests get and the expectations. If he's calling you at 2am expecting you to drop everything it's much different than a laid back "hey, can you help me with this quick when you get time?". As others have said this is someone you want to owe you favors and keep in his mindspace. It definitely needs to be reciprocal over time. Sounds like it has been so far, so I'd see how it goes. What happens when you ask him for a favor in return? And he's feeding you side work? Think of it as a small agent fee if so. I'd love it if I knew some IT guy who I could hand projects off to and just know they'd be done well. I'd overpay quite a bit, and I have extremely high standards for my home stuff.

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Th1s1sChr1s@reddit

You are his tech for life unless the relationship turns weird. I don't want to say 'don't burn that bridge' I want to say, Pave it, put in some nice street lights and a walkway for pedestrians - foster that relationship.

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quangtit01@reddit

Motherfucker went above and beyond to look out for you and you bitches and whines about some ipad??????

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scarey99@reddit

As has been said. Just keep doing it.

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IncidentProud8807@reddit

I have a coworker who’s about my moms age who calls me every few days. Initially I was worried about boundaries but I’ve grown to like these calls and this has actually been fruitful for me. Has taught me a lot and looks out for me.

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Tax_Evasion_Savant@reddit

well I am the opposite of most of this thread it seems. A few things to consider. 1. This guy is very rich, he needs help much less than you do, but still expects your help for free? 2. This post only exists because there is a toxic power dynamic between you. All you are getting out of this exchange is him not ruining your reputation. 3. This guy ran a large company, he understands labor and he understands that he is asking for free labor. 4. All the things you felt like he did for you, you worked for, you earned, you deserved. He didn't give you a raise, you EARNED a raise and he agreed. 5. CEOs are paid a disproportionate amount to the labor they provide, if anyone owes someone something, this CEO owes all the workers who made 5-10% less than they should so that he could earn 800% of what he should. I would start asking for things in return. Next time he calls, ask him if he can help you with getting a raise. If he cant reciprocate, its time to stop helping the rich guy who you owe nothing.

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Trinikas@reddit

Well what I'd suggest is not set the boundary as "no" but if he's calling and it's genuinely not a good moment you can sometimes say "hey, I'm in the middle of something, I can't help with this at the moment."

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BasdenChris@reddit

It’s hard when you do something for a job and people want you to also do it for free. Even harder when you used to do that job for them. For money. I don’t really know what the right answer is for you, but in this scenario I probably would help him whenever able. You are still absolutely within your rights not to answer a call or drop everything and help when it doesn’t work for you, and there’s a gentle way to communicate that if you have an interest in setting *some* boundaries (“I can’t do it tonight, I have a family thing. Can I meet you next Saturday and walk you through it?” and/or “I won’t be able to help this week, but if you need help right now call ____”) but for me, I’d probably just take it case-by-base. I don’t do any form of IT/Technical work at my job (at least not in an official capacity—I am my department’s de facto tech guru though), but I personally enjoy being helpful, even if asking “did you capitalize the R when you typed your password” gets frustrating after a while.

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FucklberryFinn@reddit

5 figure bonus checks... And he's tired of helping the dude with his iPad. F U, buddy.

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zetneteork@reddit

Was he nice to you, when he was CEO to you? Do you feel comfortable with him? Do you have any limit how much you want help him? I have this mindset, never miss any occasion, Do things selflessly. Don't take things for granted.The best deals are made over a beer or dinner.Sometimes we don't understand things now, but only after a long time. Surround yourself with people who are smarter and better than you. I recommend you to read or listen this book. https://en.wikipedia.org/wiki/How_to_Win_Friends_and_Influence_People?wprov=sfla1 Dale Carnegie is my favorite author.

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Sharp-Plan-1452@reddit

This fellow thinks of you as a friend.

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Ilovecats1842@reddit

Respectfully, this guy is your friend. It can’t hurt that much to help someone out once in a while. Even if you are strictly utilitarian, having a prominent CEO as a potential letter of recommendation for future work or as an advocate in the company is worth exponentially more than whatever you could get done in the time you help him.

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KomatsuSoku@reddit

Help him and you are doing it because he did you right when easily he could’ve screwed you over. When someone does me a big favor like that I remember that and will repay it many many times over. He also seems like a really nice person and plus he has a pull even though he isn’t in the drivers seat. You should treat this as a favor that will only help you out many times over.

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James_Bolivar_DiGriz@reddit

Even retired, this guy may play a role in whatever is next for your career. I have been in a very similar situation, and as long as the requests he's giving you are an easy lift, and not asking you to design new infrastructure for his house or something, I would keep that bridge open. People like that tend to be generous to the people who are generous to them.

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GamingIsNotAChoice@reddit

It's a bridge you didn't ask for and might never need but burning it might costly. It's like having infrastructure on your property you don't use but need to keep repaired.

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Consistent-Area-1126@reddit

it’s not “shit”. he values the relationship and you as a person. you have no idea what value you contribute to his life. and you also have no idea how the karma will reciprocate (although that shouldnt be the reason you help).

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Spinnaker91@reddit

Founders never retire. He’s probably still on the board and getting compensation from that company for advisement and certainly a major shareholder. Help him like nothing has changed.

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SpareIntroduction721@reddit

Are you a dummy? Just asking.

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mountaingator91@reddit

If easy tech questions are all it takes to stay in this dude's good side then it seems well worth it. You never know what will happen in life. Having this guy in your network is big.

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EffectiveVarious8095@reddit

Hey boss, I'd love to start that very important project of yours, but the former CEO (you remember, name on the building and all that?) just called me and really needs my help. I'll be out the rest of the day if that's OK.

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-MDEgenerate--@reddit

Just help the guy update his iPad dude it's not that serious

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andnothinbutthetruth@reddit

Think broader in terms of your own path. This is a person who can push you much further if or when you have questions. They are never truly retired. You keep people such as him tight within your social network.

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opus-thirteen@reddit

> The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures) That's really a non-sequitur. Sure, you got those things, and at the same time he made much more money off of your work **than you did**.

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Caurien@reddit

Help him as a friend and ask him how you can reach your career goals. Sounds like someone that can or is a mentor and would gladly help you.

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anders1311@reddit

The simple answer is there’s no saying no without burning that bridge.

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PrettyBigChief@reddit

I have retired professors emeritus hitting me up occasionally, almost same kind of deal - they are still connected to the org and staying in their good graces is in my best interest.

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Dkoerner@reddit

I send a card to five ppl each year on thanksgiving, but it's not a normal christmas card. Its a cheap thank you note that says '\[name\], I wouldn't be here if it wasn't for you, and I'll never forget what you did for me.' and then I sign it. When these five people ask for ANYTHING, they get it from me. You post on facebook that you are doing a 10k for AIDS relief? I am donating. Your kid writes a book and you share how proud you are of them? It's on my shelf. You email me that your niece is looking for someone to interview for a marketing class, I am reaching out by phone and email and opening my rolodex to try to help them. You shoot a text randomly to say thanks for the card and ask how I'm doing, I tell you about the wife and kids and remind you how grateful I am. I don't just try to pay it forward, but intentionally show that what these people did for me is something I will never forget. Note: I wish I could extend this to a few more people, but due to time and cost I currently limit to the five that mean the most or gave the most. Four of the five are retired and and all are not able to directly help me at this stage in my career, though when I started thanking them this wasn't the case. One continues to be a mentor and I buy him breakfast or lunch when we meet up to talk about work. tldr: If this guy is one of the few people most responsible for the success you and your family have today, consider it an honor to pay that back plus interest.

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thedube1978@reddit

sounds like he still owns the company so yes, suck it up, do it on work time so your still compensated

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HarrisBalz@reddit

Dumbest post I’ve ever seen on Reddit. Holy shit

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parasyte_steve@reddit

This is kind of how networking happens sometimes. He is obviously crucial to you keeping your job, and I would still treat this person like a boss imo. I would maybe mention something like "you know with my workload at the office and my life I barely have any time at all" to see if he maybe picks up the hint lol idk, I would be wary of pissing off a person like this. If my money depends on it sorry but I will probably just kiss your ass and take the money.

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Kern4lMustard@reddit

A friend in need is a friend indeed

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Agreeable_Peak_6100@reddit

Help him out as a friend and expect nothing in return.

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rikjustrick@reddit

Christ, sure seems like the guy has looked out for you. Why wouldn’t you do the same?

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Justa_Schmuck@reddit

I don’t understand the responses here. Your relationship with him was a working relationship. That is now no longer the case.

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coldfusion718@reddit

You know things are only that cut and dry on paper, right? That founder still has a ton of influence. It makes no sense to give such a person the polite fuck off speech. There’s nothing to gain from that. Now if OP’s boss is giving him shit, then let the founder and boss duke it out. I doubt OP’s boss would want to piss off the founder, even if he’s retired.

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Justa_Schmuck@reddit

It’s not a cult. We have a job spec, don’t expose yourself to anything outside of it.

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coldfusion718@reddit

Yes stick to the letter of the policy. They can’t fire you because that would be illegal. Now let’s say later on you need someone to grease the wheels for you. Then for some reason, this grease is nowhere to be found. You can’t prove anyone is fucking with you behind the scenes. Then you tell yourself “Yes it was worth it because I went by the book.” And for what gain? Just so you can tell this person to fuck off?

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Justa_Schmuck@reddit

You folks are wild. They don’t work together any more. The OP doesn’t owe him anything. Any progress they make in their career is a recognitions of effort they’ve put in. It’s not a debt.

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Admirable_Advisor711@reddit

Stop being a biatch.

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PositionAggressive69@reddit

he asks you because he trusts you. bite the bullet. he paid in advance

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No_Tallant@reddit

Dude I had to regularly go to elderly board members houses to fix shit when I worked at our local hospital. All I ever got was the old ass printer I replaced one time.

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Nodan_Turtle@reddit

Saying no here seems like a terrible risk/reward decision. Hell, if he's that close with current execs, if anything I'd keep buttering him up.

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roccoo1@reddit

Can’t wait for the “TIFU: by posting about my retired CEO asking me for IT help. I wanting to politely decline, but he some how find out about the Reddit thread.” post 😂😂

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Habesha2001@reddit

Sorry my new boss has gotten me really busy. Wish I could help. How about Friday afternoon over drinks at your house?

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steeple_fun@reddit

I would definitely just be a friend to him. Help him out when he asks but he sounds like a good enough human being, ask him to lunch sometimes too. You can't really have too many friends.

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83poolie@reddit

I don't think you should frame it as you have. He's coming to you I think as someone he's grown to trust. He may be still adjusting to retired life and you provide him a connection to that. If he founded the company, does he still own it? If so, he's kinda still your boss. If you are comfortable with him perhaps try and make it clearer that you work for the company that he no longer run, while you are happy to help, he may need to wait for your availability. Personally, if it's only basic stuff that's not taking up too much time I'd just do it.

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iKaine@reddit

That’s a very small ask considering what he sounds he’s done for you

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Neither-Luck-9295@reddit

Yeah OP sounds like a dick here.

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Bowshocker@reddit

To be fair, I wouldn’t go as far as saying a dick. I get it, the CEO was responsible for a majority of OPs career, but OP hopefully also deserved that and paid back in his services throughout the time he was employed, doing his very best and therefore deserving bonuses, promotions, raises. Yes, OP can decide to pay that back by offering his services even after the CEOs retirement, but more realistically all that OP pointed out the CEO has done for him was part of OPs work, nothing outside work. It’s not like the CEO paid for vacations, covered his families health care more than what would be usual, or anything similar extraordinary.

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Kogling@reddit

You're conflicting things here. OP didn't have to say almost 99% of what he chose to share. He could have said "boss has retired but asks me for tech support" everyone would say drop him like a sack of spuds. How he framed it was very much in the realm of "this is how generous this person is, but now I can't milk him should I cut my losses or hope the cow starts producing again?" OP owes nothing to the boss, as you said his generosity should be reflected as a business transaction only, so the question purely serves as a "what do I get out of it" It sounds about as honest as : "My elderly neighbour across the road is a millionaire abd lives in a house worth a couple million at least with no family around, do you think I should put her bins out wink wink"

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Floppydiskpornking@reddit

Totally, OPs only worried about "burning a bridge", sounds a lot like "should i keep being "friendly" I might be able to exploit him more"?

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Kogling@reddit

Mind blowing how this is even being asked by OP too. It almost sounds as: "he's no longer my boss so it's not like I have to suck up to him to get my overly generous pay rises anymore, but I'm wondering if I should continue just in case it pays dividends to me in the future somehow?" OP should admit he's a vampire only interested in blood so his ex boss can hopefully bless someone else.

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DependentOnIt@reddit

Yep this post is bait. Hm guys should I go hang out with my CEO? He's kinda a bro but idk why he's calling me teehee

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Normal-Condition-734@reddit

Send him a bill.

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Environmental_Bag_10@reddit

Help him as for the past 5 years he has helped.

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waynofish@reddit

Keep good with him. People that high up, if it's a large company, typically don't stay retired and if they do, they always remain connected.

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postbansequel@reddit

I don't get it... You're saying you owe the guy a lot but you don't want to help him with those simple things? He's done a lot for you, you say, but you don't want to do anything for him? I... Don't get it.

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Repulsive-Sundae9468@reddit

Although he has retired, the chances are that he still has some links back into the Company. Unless he is asking every day / every week I’d keep him sweet for at least a few months. Also he has been good to you throughout your career, maybe it’s time for a little payback - he obviously sees you as a friend - so long as you get a coffee and a chat what’s the harm

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akal213@reddit

This is an extraordinarily selfish thing to ask. Help a brother out man.

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ChampOfTheUniverse@reddit

Honestly, I'd wash his car here and there if he asked! Jk, but really though it sounds like he's been awesome and an integral part of your success. A damn advocate like that is worth its weight in gold. I've never had anything like that.

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Landon1m@reddit

This is not the bridge you want to burn or even add speed bumps to. This doesn’t seem too bad. Personally, every once in awhile when he calls I’d ask “hey, can I run something by you and get some advice?” Doesn’t need to be big but you could use it to help your career further.

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memyselfandus_1999@reddit

I have a similar relationship with a doctor friend. He was my neighbour when we first moved into the city. He was completing his MD, and I had just started my IT career. I am their go to IT consultant, and he is our on-call physician. We do not charge each other. It is not as if he has a fulltime staff at his clinic to fix computers, and I also have a local physician for regular ailments. We simply rely on each other for advice whenever something new comes up or when we need a quick reference. My view is to stay friendly. He can become an excellent long term career coach and a strong reference for future jobs.

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Horror_One_806@reddit

Send him invoices. As a "former ceo" why have you not thought about or done it already? Shit ain't free??

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knowitallz@reddit

I will look into it. I think it's a good idea. That's the end of it.

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mrkstr@reddit

I would either suck it up or find someone at the company with more time on their hands to help him.

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Every_Level6842@reddit

He helped you and can continue to help you through his contacts so what’s the harm in helping someone who has shown u respect and care in the past?

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EastSwim3264@reddit

Brother, please do not under estimate the value of relationships. Such CEOs are like trees - they give the shade under which many earthlings make life. If I were you, I would think it as a kind of gratitude repayment. FYI: I helped a guy, few times, manage multi-million $ finance portfolio using simple excel spreadsheets just because that guy shaved off $500 from a used car I bought from him.

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mjones8004@reddit

You received "multiple" five figure bonuses and you are on *Reddit* asking this hot garbage??

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BIFF@reddit

Guy is asking us all if it's ok to be as lucky as he got

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WorriedHelicopter764@reddit

uh dude just help him out a little

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jBlesse@reddit

its your shot but this CEO looks like a chill guy, it can be annoying but I think its just worth to help the guy out

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MikeT8314@reddit

Bite the bullet for a good while. Sounds like this guy was a great boss. Also self servingly these are guys often can still help you even after exiting.

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Fragrant_Poetry_9736@reddit

These are the kinds of friendships you water.

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DeeJayDelicious@reddit

Oh man, he sounds like a great guy! It's always useful and good to stay in touch with great guys. Even if they're occasionally annoying. Especially ex-CEOs often spend their time being well-connected with other founders and big money. So it might even pay off in some way to stay in touch. And it doesn't sound like he's asking much. Also, maybe he just wants to chat and stay in touch?

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PlumpyGorishki@reddit

You need him more than he needs you. You just fail to recognize opportunities because opportunities always present themselves in work overalls outside of work. He can easily hire someone. You on the other hand choose to count pennies.

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Hybridxx9018@reddit

This guy said “absolutely” with no hesitation when you asked for large raises and promotions? Gave you big bonuses? AND he’s friends with current execs that technically could have you by the balls if push comes to shove? Dude, with all the shit stories of bosses nowadays, you got this person in your corner and all you gotta do is play tech tech support once a week?? No offense and sorry to sound mean, but you need to stfu and keep helping this person lol. This is a great opportunity for you to keep your network going. And honestly, just to be a good person is nice too..

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TrickEye6408@reddit

It’s the bullet unless it becomes all consuming. If you have a reasonably good relationship with the ceo you could parlay that relationship into becoming staff for him for a yearly stipend. Make a joke about you’d be on call for him for a fee…Even if you can’t manage that you should be able to have discussions about timelines for responding so you can manage your time. If it’s a once in a blue moon request just do it and take it as an opportunity to catch up . Networking is about people…never forget that your network is your biggest asset

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wetmedjooldates@reddit

Humble brag

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bertramt@reddit

Generally if they appreciate you enough while they paid you, they will find a way to compensate you post retirement also. That said the more removed from daily business life they get the less technology issues they tend to have.

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Sweet_Mirror3992@reddit

Yeah man, you should do it. What goes around comes around. This guy saved you years of stress and physical/mental issues, and made you advance in your career in a rewarding way. Not too many people get that luck. How many times can he set up an iPad or his personal email? Now.. if it becomes a daily unhealthy thing, then sure. But then again I'd try to befriend that guy outside of work, he seems like a good person, and you hold him in high esteem. Go to his place (if possible) grab a drink with him, chat about life and how's the retirement coming along while you configure his iPad. That's what I would do anyway.

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Suspect_Afraid@reddit

Maybe look at it as he is looking for an excuse to continue a friendship outside of work and these are his excuses? Someone that accomplished will most probably have better/easier ways to sort out his IT issues. Maybe instead of him reaching out, you reach out and shift the paradigm of the relationship a little bit.

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mrgreyeyes_95@reddit

It never hurts to be in the good book of a CEO. It puts you in a position to ask for a favor in return. Ask him to connect you to other CEOs or put in a good word during a job interview.

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Dramafree770@reddit

Who says no to such connection?

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Phillyflu75@reddit

Use this as an opportunity to continue your career growth. He's got your back, you get his and he'll take you to the moon. He might be retired but he's THE man. No downside to keeping him happy.

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ColdStockSweat@reddit

*"He's signed his name to hefty bonus checks every Christmas (some 5 figures)."* And you're looking for a way to say "NO" to this guy? What a POS.

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GetShttdOn@reddit

Ehhhhh idk man. Seems like hes done alot.

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TPUBG29P@reddit

I'd help him out. Bosses like that are scarce. You never know what the future holds. Maybe he gets bored in retirement and starts a new career, and offers you a lot to help run it

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Human-Living-4083@reddit

He has treated you extremely well, for example 5 figure bonus checks! yeah help this guy out, he’s been more than just a boss to you.

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Chumbag_love@reddit

This dude has connections you want, you should be offering more assistance

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PoolExtension5517@reddit

Sounds like a stand-up guy who treated you and everyone else well. He’s also potentially in a position to help you out in the future should you need a reference, so maintaining this relationship is probably worthwhile. Consider it your weekly good deed for good karma. Or not. Your choice. Relationships can be more valuable than a great resume, though.

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UchihaPolice@reddit

I would say to accept his requests and observe if they are biting into your family time. Considering all the extra favors he approved for you, you should give him a shot.

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MacMemo81@reddit

Never underestimate a friend like this in your network. Scratch his back and he might scratch yours in the future.

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Even_Reception8876@reddit

He’s asking you out of trust lol. Help the poor guy out. If it is overwhelming like 3 times a week help me install the dvd player that is one thing but he may be lonely and also looking for an excuse for someone he enjoys to come help him. You probably always seem excited and eager to help (even if in your head you feel otherwise) and he has done a lot for you. I agree with what others has stated, try to get him to go out to lunch or go golfing on a weekend (even if it’s just too golf or shooting range) and may turn into you guys hanging out instead of helping with the tech. But he clearly values you and trusts you and that says a lot about your character. End of day it’s your call but think it all through a little bit before cutting things off. It’s nice to have friends outside of your age group.

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shitty_ninja_turtle@reddit

Small price to pay. You aren’t really being taken advantage of considering all the support he’s given you over the years. Sounds like a stand-up guy

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OldMove3348@reddit

You’d be silly to not help him. This is the kind of contact/boss that will inevitably call you one day with either a new/better job or introduce you to someone looking to hire.

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tiasaiwr@reddit

Consider it networking. How much is 4 hours of you time worth over the next year or so to potentially get hooked up with a 5 figure raise at a new job when he recommends you?

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yungsolid@reddit

Nepotism is no joke buddy help him out

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LynmerDTW@reddit

As long as it doesn’t interfere with your paid duties, and as the former CEO I’m sure he would not want that, once a week for a phone consult isn’t a huge price to pay for networking and continuing access to a very successful gentleman that obviously values you and your skill set.

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spacecaps85@reddit

Retirement is probably really boring and maybe even lonely for people like your boss who seemed to be a good dude, built a business, and cared about his employees. That's a lot of "purpose" in life to let go of. Invite him out to lunch or for some beers or something once in a while. As for the tech support, you'll be alright. Fix the iPad once in a while.

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cybersaint2k@reddit

This is ideal. There's no bullet. Make computer love to him long time, Joe.

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Contagious_Zombie@reddit

Sounds like he respects you and trusts your advice.

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capsteve@reddit

I was in a similar situation, eventually I went to work for a different company and said that there were conflicts that required “firewalls” between us on a business level. He grumbled, x2 pay offer, but I asked that we keep our friendship separate from work until we aren’t competing. I still talk to him regularly after 15 years.

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EmptyLibrary2@reddit

I know we're often told to learn to set boundaries and say "no," but this isn't one of those times. Say "yes" gladly and realize that maintaining the relationship is important both personally and professionally.

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pythonicprime@reddit

Dude - ABSOLUTELY bite the bullet

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Diamondhands_Rex@reddit

Sounds like a good guy what did you leave out that wouldn’t make you want to help him?

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Equivalent_Sound424@reddit

You shouldn’t say no. This person did a lot for you. Pay it back. I know you worked for whatever you earned, but a lot of people, probably most people, are not treated like that by their bosses.

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Correct_Cat4414@reddit

I don't think there is any wrong or right here but I personally would help him out occasionally. I'm willing t o bet he still has more influence than you think.

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Thr0waway0864213579@reddit

First of all, I think it’s important to reframe this. He didn’t put that new truck in your driveway. You did. You had the work ethic and skillset *he* desperately needed. And you spent years of your life working hard to earn those things. You were not draining the company of its resources by taking a paycheck. You were getting paid for the value you created. And I promise you, whatever you were paid was equal to or less than the value you provided the company. I don’t know what the company does, but imagine a medical software company with no IT. What value is it a CEO going to be able to generate without IT? None. So I totally understand being grateful that he is not a dick. But this man simply paid you for the value of your labor in a world where many other men choose to greedily hoard what our labor produces. That being said, kindness is kindness. And I think you should attach yourself to kind, selfless people whenever you can. He’s not owed this from you. But there may be a day where you need a good word or just someone to ask for help. I think it’s worth a small effort to keep someone like this in your corner.

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Desperate-Service634@reddit

Take him out to lunch Tell him how much appreciate him Tell him that you are flattered that he feels like he can depend on you , after all the years that you had worked together. Unfortunately, the company and your family still demand that level of loyalty, and time commitment. I’m happy to help you, but I have to limit myself to one visit a month, or whatever other boundary you feel like you can do. But yeah, this guy put a lot of coin in your pocket. Maybe it’s time to get back a little bit.

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Almostasleeprightnow@reddit

For me, the more I see my parents age, the more I hope that strangers will have a little space in their life for helping them, and if it is truly just nice a week and not that mic of an impact, I might just keep doing it. If the demand is too much or actual work needs too much from you to have time then I might explain that and back away.

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blackcatsarechill@reddit

Help him when you have time, don’t make it a priority.

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bbatardo@reddit

I'd be TS for a former CEO just in case for a connection or reference. Small price to pay really.

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MrsPetrieOnBass@reddit

I think you already know the answer. There is a line somewhere, but it sounds like you owe the guy a lot for what you've achieved together.

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Raven-19x@reddit

Imagine burning this bridge over such a minor inconvenience. Do it on company time if it bother you this much.

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ModestlyMinted@reddit

You have a golden opportunity here to be friends with a guy who could mentor you with knowledge that takes decades to acquire. Ask this guy to a friendly lunch sometime. Be a good friend and keep helping him with his stuff. He sounds like a good guy from the way you described him. Don’t piss away this opportunity to grow. He has knowledge to share with you if you’ll ask the right questions that’ll be way more valuable to you than the help you’re offering him.

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jaywinner@reddit

He did all that for you and you won't fix his printer? Even from a purely selfish point of view, that's a very low cost to keep a very important bridge sparkling. Don't be stupid.

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FigSpecific6210@reddit

I’d do as side work, off the clock. This guy should understand and appreciate the separation of work/home support.

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Several-Light2768@reddit

Dude keep helping him you never know what someone like him is going to be up to in a few years. Lot of type A personalities will retire and start something new in less than a year. You might trip and fall straight into a leadership role at his next adventure because he trusts you and you trust him. Win/win. Plus if you like the guy no harm in helping with stuff here and there.

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CWhisper@reddit

This guy can recommend you to others willing to pay you more than you currently make. This guy can help set you up in your own business. This guy can throw you year end money for no reason other than being a good dude. I hope you do turn him down. You don’t deserve to have acquaintances like him.

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Stock-Page-7078@reddit

Maybe just reach out and tell him you have a going rate for private services and ask if he would like to do that?

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BigMasterDingDong@reddit

Damn, let’s put it this way, I wish I was in your situation. Sounds like he’s opened a lot of doors for you and he trusts you and just needs a hand now and again… sounds like a good deal from your side!

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Equivalent_Buy_3027@reddit

Don’t answer

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simulation07@reddit

Need more info. What are your responsibilities. How many hours do you work. Are you living comfortably? Are you fulfilled?

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XCrMTB4x4@reddit

I think it’s worth taking his call and helping him out. I’m sure over time it will become less frequent.

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Recentdig7470@reddit

NTA. He could hire his grandson for all you care.

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Apprehensive_Pea7911@reddit

Good idea to support him and invest in his ability to help you in the future. Bad idea to blow him off just because he's retired. Very short-sighted.

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JagiMonster1@reddit

New CEO to Old CEO: hey how's it sound to you if we made OP the VP of blah blah blah? Oh hes great, he helps me out and is pretty cool, he'd make a great fit.

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MentalSewage@reddit

Start asking him for favors in his expertise or wheelhouse. Grab lunch. The thing about a lot of executive types is they surround themselves with skilled people to trade favors and network; and they are more than happy to serve their end more often than not. But if you don't ask, they will just assume you don't need their expertise.

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Mattbl@reddit

My wife is friends with a couple former executives that she worked for who "retired." They still know a ton of people in the industry and talk to them regularly. They also consult. Not a bridge you want to burn. Also sounds like the guy really took care of you. Your experience is abnormal and VERY lucky. "It's not what you know but who you know" is very applicable here. Imagine you keep helping this guy with easy stuff, whose name will be forefront in his head when a friend or former colleague of his comes to him needing an employment recommendation?

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Electronic-Cheek-235@reddit

Charge him like he charged you lol. Remeber that raise u didnt get? Make them pay

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white-christmas@reddit

OP send him my way, I need a job rn and I'll give him all the tech support he wants.

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Inevitable_Youth_495@reddit

Seems like he was a positive influence in your career, which helped improve the quality of your life. He was more than fair as a person who was way superior to you in position. Did he ever make you feel otherwise? Why wouldn’t you help him?

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Lukozade2507@reddit

Wish I had this problem...

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implicate@reddit

Normally I'd say fuck that shit, but in this scenario, I'd likely do whatever he's asking as long as it's not huge.

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Cautious_Buffalo6563@reddit

Consider creating a basic tutorial video and job aide document for him to help him become proficient in trouble shooting his own devices prior to asking your assistance?

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podgladacz00@reddit

5 figure bonus? You are his personal assistant until you quit this company man.

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YodelPoo@reddit

Send him an invoice, reference it next time he calls

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Separate_Durian_5801@reddit

I think this is also an indirect way in which CEO wants to hang out with you though thats my assumption.

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Miserable_Trifle8667@reddit

Really? Cmon bro

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Deep-Viking@reddit

Helping what sounds like an ally out is a worthwhile endeavor without a reward. If the ask gets too large in scale, ask about doing it as a consultant for him. The little things could lead to a new opportunity in the future, and someone at that level won’t be surprised by needing to pay for a service from a friend.

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rex_tee@reddit

Once a week? C’mon, do yourself a favor and keep helping this guy. It’ll be good for you

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Ode1st@reddit

The way you describe the guy and what he’s done for you, it sounds like occasionally helping him with an iPad or whatever is worth it just to repay him for all the times he’s without hesitation made your life better.

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Additional_Dish_694@reddit

Andy?

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callaway_123@reddit

As long as you are at the company, you gotta help

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metasophie@reddit

You should ask him sometime what would you should target to one day be a CTO.

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ElegantButterfly54@reddit

You can be grateful without being on permanent tech support duty.

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BigDuckNergy@reddit

Damn I wish I had a cool boss that recently retired and wanted to chill. Does he have kids? Maybe he needs a homie!

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Medialunch@reddit

Would could try to delay your response to him by a few hours. Make up some excuse. Do that a few times and he will shift his dependency to someone else.

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MarALolita@reddit

networking /ˈnetˌwərkiNG/ [](https://www.google.com/search?sca_esv=cea07bd29ebaa7bd&rlz=1C1ONGR_enUS1181US1181&sxsrf=AE3TifOAlo4wV0yIX3ZGC1LeV10ZaCfnFQ:1767384396597&q=how+to+pronounce+networking&stick=H4sIAAAAAAAAAOMIfcRowy3w8sc9YSnjSWtOXmPU5eINKMrPK81LzkwsyczPExLjYglJLcoV4pPi4eLKSy0pzy_KzsxLt2JRYkrN41nEKp2RX65Qkq9QANSVD9SWqoBQBABIQEJeXwAAAA&pron_lang=en&pron_country=us&sa=X&ved=2ahUKEwjo74_50-2RAxWzBrwBHYYTGtUQ3eEDegQIIxAN) *noun* noun: **networking** 1. the action or process of interacting with others to exchange information and develop professional or social contacts. "the skills of networking, bargaining, and negotiation" 2. the linking of computers to allow them to operate interactively. "the demand for wireless networking is increasing rapidly" as a sysadmin, i am going to assume you know one of these definitions already

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keramikus@reddit

Absolutely help him.

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lbdrift@reddit

I’d suck it up and be a little gracious

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AugmentedKing@reddit

Make a joke about where to send the invoice, gauge his response then act appropriately

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RR1904@reddit

I'd help him. Sounds like a friend to me.

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MannerOutrageous4569@reddit

Chomp down on that bullet, sounds like someone you want in your corner. Even more so sounds like he's had your back quite a bit so what's a few silly calls once in awhile?

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AresBou@reddit

If he's still in good graces with the rest of the c-suite, then his political disfavour is a liability.

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dead_wax_museum@reddit

Just start saying “I’m not sure how to do that. You may have to call tech support” more and more often. He’ll take the hint eventually

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OriginUnknown@reddit

That is insane that you're complaining about needing to answer the phone for this guy. What is wrong with you?

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acederp@reddit

You can probably tell him "I would like to but im busy on company hours" and he will make a phone call and let you help him during work hours. Which would probably be easyer.

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Mauceri1990@reddit

I've literally built gazebos and decks and all kinds of shit for people that have done far far less for me, be a homie and just help the guy out on occasion, unless it gets to the point that he's calling you every few hours for help I don't see why you'd mind.

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andyomarti5@reddit

From a purely selfish perspective - you are in with biggest-big-boss. Don’t mess it up!

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Spiritenemy@reddit

A friend in need is a friend indeed, and even though he's no longer your boss, it still sounds like he was a very important figure for your development, I'd recommend shifting the relationship though so there are clear boundaries if it becomes problematic.

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PourSomeSugar69_420@reddit

Yeah. Help him out with the little things

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Engorged_XTZ_Bag@reddit

All good responses for what OP should do. I will comment on what X CEO should do. He shouldn’t assume you owe him anything and he should be going out of the way to compensate you even if you say no. That would show he values your time when he is personally paying the bill and not from company coffers.

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SomePeopleCall@reddit

If it starts eating up too much time you can push to keep this after hours and ask for a bit of consideration. Money is easiest, but a meal or your favorite poison can be a good option.

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MyDixeeNormus@reddit

Not only does it sound like a friend asking another for help, this guy is still incredibly plugged into your careers world and the people in it. I’m not saying you should keep helping him JUST for that, but I’m guessing you’ll be able to ask for help down the road and he seems to be in a position to make things happen.

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CrucialFusion@reddit

Sounds like he’s done you solid multiple times over and you’re complaining about a few minutes here and there. Think you better weigh that out a little more.

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2lovesFL@reddit

slow down on helping him, maybe screw up some things. You probably need to keep supporting him. try to get him to drop it off at work, then spend a week to return it. delay, delay, delay.

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Phxdown27@reddit

Just help when you can. Boundaries are OK and so is helping people who helped you.

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donzdozit@reddit

What is the saying ? My steak is too juicy and my lobster is too buttery.

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goomyman@reddit

It’s always good to be maintain a friendship with someone with strong connections. It’s likely worth it. Up to you.

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Bannedwith1milKarma@reddit

Make a joke like 'What'd you reckon the consulting rate for iPad troubleshooting would be?' Hopefully that flicks his head into gear and he gets you a nice bottle of Whiskey or something.

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Mr_Snowbro@reddit

Don’t be stupid help him out. He may be retired but guarantee he still has a lot of political sway in the business

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CreativeJudgment3529@reddit

It’s free to be kind

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BatemansChainsaw@reddit

Dude, like so many other commenters here this is one of those moments where you get to scratch their back more than they will you. It's not a bridge to burn but returning the goodwill he's given you that most of us can say hardly anyone does anymore. Suck it up. In fact there's only one limit I'd *ever* impose on this kind of arrangement and that's asking them to bring it in (or meet them for lunch nearby) so you can work on it during business hours. It gets them into the office to visit and socialize, you can rub elbows with the other execs (AS YOU SHOULD) and not spend time outside of business hours when you should be with family.

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StartingOverStrong@reddit

Maybe all the extra things he did for you is because he saw a lot of himself in you and wanted to mentor you. He certainly seemed very invested in your success. And now he's retired and can really pour into you if you let him I have had older people do that for me – literally ask me to come help with something or come sit with them during medical treatments and then they would pour all kinds of knowledge into me. This generation (boomers) of older people doesn't see them as interested in doing those kinds of things Or, he could be retired now have less "Power" and realize he doesn't have anyone else to lean on and is leaning on you inappropriately Or something in the middle If you feel once a week is him asking too much, try not to be available for as much. Conveniently "miss" every other call. Space out the times that you help him and in between send him a text or leave a message that basically says "I can't help right now, I'm busy with XYZ but Here's what you can do. Google search this and it will walk you right through this. Let me know tomorrow how that works out and I can swing by if you still need me to" His reaction to this is more important than getting the words just right. If he reacts kindly and appreciatively, then it's likely he's not just trying to take advantage for you or just feeling lonely. Especially if his requests are not increasing And if he genuinely cares for you, allow him to do so as much as you have the bandwidth for. Very few of us anymore in today's world have high caliber people are willing to stay connected with us, mentor us, care about us, TRUST us You said him asking once a week he feels like too much - do you just not like him? Do you not enjoy his company? I know he helped you and your family financially with great bonuses and raises, but is he that horrible to be around? Are his request accelerating? Are you worried about being over there every day without compensation? If he's great but you're busy with supporting the new CEO and taking care of your family and want to enjoy your time off without feeling like free help, begin to let him know that "I wish you could come help right now but I'm super busy with blah blah blah" Another route you could take is let them know your formalizing the side work you do into a complementary (not competitive) business and when you help him ask him for business advice while you are over there This covers helping him, give him away to feel useful, and gives you some compensation for your time There's a way to do that while still generating space as a boundary "I can come help with that tomorrow – in the meantime try googling this and following a video that comes up. Hey, while I'm there maybe you can give me some advice on this issue I'm having with my side business" I know this is long, but one last thing – my family is from the USA Northeast. You don't ask for help unless it's kin or you're trying to take advantage of them. My first husband was a military man and i've lived all over the world. In some places what he's doing, like others have already said, is trying to build a relationship. Unless he's just a horrible human, consider this part of your human kindness/pay it forward (again, as long as you keep it within boundaries of what works for your current job and your family

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TwoThumbFist@reddit

Ask for more money to make it worth your time. If you so connected to the founder of a successful company it not that much of an ask.

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that_yung_lad@reddit

honestly dude, and I'm prolly saying this for the WRONG reasons, just keep helping him. for all you know this can greatly benefit you down the line, and if it isn't a huge lift or deal, just keep helping. maybe y'all end up being friends IDK but it sounds like something that's kind of a "why not let it ride"... unless it's really upsetting you. the way I see it, worst case scenario you're helping an older gentlemen with technology and it teaches you more patience. best case scenario, he tells other execs how helpfuland willing you are, and I don't need to tell u how that can help ur career.

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ResponsibleSail5802@reddit

it's ALWAYS 'not what you know, it's who you know..." yes you are his tech support for life- like you would be for your parents or your kids. I would suggest getting lunch with him sometimes or going to a show or something and also you paying for it and maybe he'll get the next time.

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Quick-Bird-2183@reddit

Why would you even give a second thought to helping this guy, he’s done a lot for you.? You sound like a self centered jerk. Loyalty goes a long way! Try it sometime.

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goldenphantom@reddit

My company's former CEO retired 5 years ago and I still occasionally do some stuff for him.

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Keldrabitches@reddit

Let us not get too big for our britches after all, lest we tear them and become mortified

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New-Veterinarian5597@reddit

YES!! You never know, you might get a $$ check every Christmas or even a part of his Will.

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alexandreracine@reddit

If it's on your work time, or work pay, and your new CEO or boss is aware and confortable with, it's fine. Usually, the new people in place have arrangements with retired CEOs to pass the torch, and knowledge and they call him too ;)

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No-Hospital559@reddit

In these situations they are asking you not because its free but because they trust you. Help them as best you can.

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ericrz@reddit

Don't say no. This is a friend you want to keep on your side forever. Draw lines if there's a logical place -- like if you can send him to the Apple or AT&T store for specific help, do so. Otherwise, you don't want to lose this connection.

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Floppydiskpornking@reddit

Yeah the ex CEO is OPs friend, OP seems like a selfish douchebag tho

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imreading@reddit

> I feel like I owe the guy a lot Sounds like you already know the answer. Up to you if you welch on a debt but no one knows better than you when you will have repaid it

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macgruff@reddit

Until yall hire someone under you and assign that duty to them…, then thats your gig

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Additional-Film-4111@reddit

Dude has ran an obviously successful business in whatever field this is in. Which means others come to him looking for possible hires, or people of interest. He probably looks at you as a loyal friend that helped his company succeed. You can cut ties with him, but it’d be a terrible business move. If you ever switch jobs, the recommendation of a successful ceo in that field will go a lot farther than you think.

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whats_his@reddit

Just think of risk (or effort in this case) vs reward. If it were me, I'd just keep helping him out. He obviously still has connections and has proven he can and will help you out.

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Farnic@reddit

If you don't want to help him I will, sounds like a great friend to have

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bnl84ewe@reddit

What did he gift you this recent xmas?

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DayOneDude@reddit

You help him.

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Critical-Test-4446@reddit

I would not hesitate to help him out after how he's treated you.

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pabeave@reddit

Guy still owns the company and calls the shots. Definitely do it

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bb-wah@reddit

Get ready to look for another gig.

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Valendr0s@reddit

Bill for it.

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paddysda@reddit

Don’t be a dick!! He wasn’t to you!!

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Ms74k_ten_c@reddit

Forget what he has done for you (i mean dont forget, just keep aside for this conversation). Having a CEO/founder as a contact is invaluable. This minimal help/contact will be very valuable in the future and do it even if it is for selfish reasons. Dont forget that 1 or 2 years down the line the new CEO may want to take the company in a different direction with changes to your role for example. Being able to reach out to someone like this CEO will put you in a great advantage.

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TDVapermann@reddit

Dude you got the buddy treatment for your career. Be a buddy back.

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Jtsanders84@reddit

It’s easier to be grateful and help than uncomfortable scrambling to navigate a way out. Kindness works. But so does honesty, if there’s a reason that you can’t assist upon his request then tell him. If you don’t want to help him then you should probably be honest and tell him why.

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Johnny_Couger@reddit

The simplest way is a short term “no’s”. I’m sorry bill, I can’t right now, but I have some time tomorrow. Just make it so you are in control and will help him as much as YOU can.

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CyberEmerald@reddit

In his mind, he’s seems to see you as a friend and not just a coworker.

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Optimal-Hearing-1463@reddit

Just maybe 🤔 he's using these reasons to be a friend like an olive branch

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frank1934@reddit

You should tell him to stop, since this isn’t real and I’m really sick of all these fake posts on Reddit.

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randomredditacc25@reddit

people believe it though, it feels like rage bait. hey this guy was amazing to me, should i help him now and then with simple tech things? what would anyone say? but yes this is 100% fake.

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lnxrootxazz@reddit

I would keep this in a good standing and help him from time to time if you value his contribution to your career so much and see him as a fair boss over time which it a absolutely seems like it from reading it... So why not helping him? I would do it without hesitation. Of course, everything has its limit... But that limit is not always the same of course

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Comeback_321@reddit

You continue to do it. What does it take, 20 min of your time? Could you handle this also the way you would in business? “Here’s a doc, you can submit your issues in and I’ll check once a week to see what I can help you troubleshoot.” I think you keep the door open with parameters. “Hi Bob, I am doing x at the moment, can I pop by and help you with this? What if we do a walk through and then have a drink or dinner afterward to catch up?” BUY him the dinner or drinks. *Continue to learn from him, his stories, your questions about the company, etc. Help him and show him you are grateful for where he’s gotten you in life. Relationships are two-way streets. And I’m sure he would love to continue imparting his knowledge with you now he’s retired.

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krins12@reddit

You’re lucky to be in this position

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JazeevaGaming@reddit

Just tell him that now he’s retired he’s out of your realm of support and you can’t guarantee that you can do anything for him. Otherwise, I’d just help him out and take it as some easy hours.

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Spearhead96Bravo@reddit

Why would you want to burn this bridge? Could be a valuable asset or at least another friend.

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s2chum@reddit

Tell him you're more than happy to discuss it over dinner, your treat.

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Funny-Film-6304@reddit

Bite the "bullet" and help him. It sounds like even a single "absolutely" christmas bonus is enough, to have paid you for a couple of years of tech support.

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BabyBurger24@reddit

Sounds like he's earned your help.

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agirlisno_1@reddit

For a second I thought I was reading a post on AITAH lol

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MsAdventuresBus@reddit

Maybe he’s lonely and really sees you as a friend? I personally would not burn any bridges. Especially if he still has contacts. Because you never know in the economy, if you may need a leg up if something happens.

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DivineDart@reddit

Scratch his back, have him connect you with his friends to take care of their IT questions/issues for a nominal fee.

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BeverlyToegoldIV@reddit

You have a weekly meeting with the recently departed CEO who has significant influence over the remaining executives. Throwing it away, especially since he seems like a decent guy, is the height of folly. Just help him out and reap the benefits.

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Skeetz111@reddit

CEOs typically have a lot of connections. I would not say no and his help him out. Then I would eventually ask him for a favor after you thought it through so you can get ahead.

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hotmic247@reddit

5 figure bonus checks? You're his tech support for life

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1975Hook@reddit

"No"

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Dunno_If_I_Won@reddit

Seems like CEO sees you as a friend or at least a familiar acquaintance. What you have there is a very valuable resource you should cultivate. Might be even more valuable than all the raised you already got. It's called networking. Have lunch once in a while. He can mentor you or provide contacts to other opportunities in the future. If not you, then maybe your kids.

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Best_Appointment_770@reddit

That you even have to ask this after only 2 months considering all of the shit he has done for you...... wow

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TurnipEnvironmental9@reddit

I would continue to help him. It sounds like it could be beneficial to you in the future to keep him happy. He could do you some big favour some day.

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kaptainkatsu@reddit

If he is making reasonable requests at reasonable times, not a bad thing to help him out as he can return the favor later (or in your cases he has been generous in the past). If he’s calling you at 2am and you show up at his house and he is naked, then that’s a different story.

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Material-Imagination@reddit

He seems like a good guy to return a few favors for, and moreover, he seems like he could still help you out in the future. I think you should probably keep helping him out whenever you can.

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M2J9@reddit

I feel like everyone keeps answering this question in the sense that you're going to be doing this during business hours and that it's part of your job which does not seem to be the case.. That said, it sounds like this guy is important to you and is asking for assistance, if this was my boss that got me off the ground in IT I would do anything he asked because he's that important to me.

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nextepllc@reddit

He might be treating you more like a friend rather than needing help. If he really need a help he seem to be wealthy enough to get tech support.

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Sarik704@reddit

Look. You dont owe this guy anything. You were his employee and he was your employer. That can be the extent of your relationship if you want. If you like him as a friend, a neighbor, or just an acquaintance, that can be fine too. You're both professionals, and now that he's retired and no longer in any way, your employer, coworker, or direct supervisor, then you two can have whatever kind of relationship you decide to have. What's important is that you are no longer contractually obligated to help him, and he can not retaliate via your employment. So, ask yourself, do you like this guy as a friend. Would you play a round of golf with him? Go to the bar? Maybe invite him to a cook out? He's asking you for tech support as a friend or at the very least, an acquaintance. It's up to you if you want to be that for him.

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CoughItUp22@reddit

It seems like you definitely want to say no, so I'll work off that. Next time he asks, politely refer him to a good service you think will be helpful for all his tech help. If he doesn't get the message, it's your judgement call on what to do next. Every boss should strive to be like him, but just being a good boss doesn't really entitle him to unfettered access to you for life, imo. My only question is, are you friends with him? Like do you hang out? If so, maybe just be the homie and help him, if it doesn't take too much time out of your day.

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DefiantFigure4906@reddit

Can you not just help him as a friend and not as an employer? He sounds a good guy

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Floppydiskpornking@reddit

"Bite the bullet"? It sounds like you owe a lot to this guy, but fuck him now that he cant do more for you? You'd gladly say no, but youre worried it might bite you in the ass, burning bridges... You sound like a real piece of work

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Fantastic-Basis3802@reddit

I’d definitely keep it up

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GloomyNectarine2@reddit

Bite the bullet, just like he helped you over the years he may help you again with a recommendation and set you up for life. And delete this thread, very easy to connect the dots

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Zombies71199@reddit

I think it is fine as long as he does nkt cakl u in the middle of the night

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handsomeGenesis@reddit

You’re helping this dude for life dude.

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BigBennyT@reddit

If these are small things your helping with and you get to spend a little time with your old boss every week, I don't see a problem. It sounds like he was and continues to be good to you. People like that are worth keeping in your life. Are you sure the tech support isn't just his way of maintaining contact?

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emziestone@reddit

Honestly, I would. He's in a transitional period. Retirement is hard for some. Many ppl are defined by their careers. I think his inquiries will be less and less. It may be tricky, or he's just finding a reason to call. You can type out the instructions to access all of these things for him, but it's my guess he doesn't know what to do with all this free time. I'd be playful for now and reassess if it continues to go on longer than 3-6 months.

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Any-Ball-7159@reddit

Just fucking do it. Sounds like you owe him your career. Would you have what you have now if not for him? Seems like a no brainer to me, you asked and he let you have those things. It’s not going to hurt you to do it or even not do it, so just set some boundaries and do it HAPPILY.

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Decent-Experience-8@reddit

To the CEO, this is normal behavior and networking. CEO’s typically get to their positions by developing and growing relationships and have strong personal networks they trust. They aren’t worried about billing for every moment of their time. Dont get run over but also dont be afraid to set schedules when you can help. A sane CEO would appreciate this.

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Much_Lingonberry_37@reddit

Treat him like a good uncle or grandfather.

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Budget_Operation_106@reddit

Idk man. Doesn't seem like a lot to do for someone who did that much for you. Sounds like he changed your life for the better, all at the cost of a phone call once a week. Guy might even just want to talk to you and using the tech support as an excuse to.

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WasteMyTime321@reddit

What is annoying about it? Just help when you can and don’t answer if you’re busy.

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oxwilder@reddit

I think part of the class struggle we don't pay attention to is feeling like we owe a company thanks because they paid us for our time and effort. The contract is "I give you all but three or four waking hours each day that I'm not working, getting ready to work, or commuting between work and home, and you give me money." If you and the former CEO are chummy enough, maybe you could start dropping hints in a joking sort of manner, like "Man, you sure need a lot of tech support for someone who's supposed to be retired!" or "You know what doesn't need tech support? A bag of golf clubs, go shave some strokes off your handicap!" (Don't know why I attempted a golf joke, sorry if that doesn't make sense.) Or the classic, "Did you create a ticket?"

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Sunteeser@reddit

I have an employee who was in the same scenario. He never made a boundary and now drives 2 hours to their lake house for tech support a few times a year.

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moosetracksicecream@reddit

Just help him.

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CP_Chronicler@reddit

Seriously, everyone else has been saying it. If THAT person is your former boss, look at him as a friend and put energy into cultivating that into a deeper friendship and view this as helping a friend. If it doesn’t develop into a deeper friendship, the requests will naturally fade away. If it doesn’t develop into a deeper friendship, you won’t feel like you’re being put out so much. It’s a win-win for you.

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GoBin_t@reddit

"The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures)" If I was in your position, I'd be happy to help him.

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Eastern_Gas_7996@reddit

I’m a guy with tremendous value to offer that is still looking for that right fit after it not working out with a group I’d done over 10 years with. With all due respect, it would be my pleasure to continue to help someone that invested in me in this way. No right or wrong to it, just my honest feeling. It’s annoying and an overreach and not your job, sure. But man, to feed my family without worry from an owner that was enthusiastic and let me touch money, that would be unforgettable for me

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Li54@reddit

I’d probably help him out. Sounds like he was a good guy to you. Likely what will happen is you’ll either become friends and not mind helping him out, or the requests will taper off over time and you’ll be off the hook.

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lavender_ra1n@reddit

For smaller stuff just do it, (he maybe retired but he still has pull at the company) but if it’s frequent enough and or large enough maybe offer him a contract.

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Bored_Eastly@reddit

If it gets too much and no appreciation - slow down your response time. Fiddle with the device and say you need to do some research. Always be friendly.

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GullibleSection3482@reddit

You most certainly do not want to burn a bridge with such a person. Industry contacts are everything and can help get you employment when other methods fail. If he is calling you everything week then once in a while just let in hang in voicemail or text. You do not have to rush reply to every request, but you do have to respond at some point. When the CEO realizes you are not on-call 24-7 he will get the message.

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Plasticfishman@reddit

I would try tossing out a trial balloon - something like, “you know, we may have to work out a retainer fee for these services” followed quickly by a “just kidding” - it may make him realize how he is actually putting you out (a bit) with these requests and open the door to an actual retainer or at least fewer minor asks. It gets him to look at his requests from a different angle in a non-confrontational way.

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Regular-Tell-108@reddit

Give him your consulting rate. I'm not really kidding.

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Woninthepink@reddit

I would buy him one year of tech support through a business of your choice.

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kevinsmomdeborah@reddit

Yes. The game is rigged and if you are that close to a ceo, exploit it. You may need his connections in the future. I have personally witnessed a low level general maintenance dude becoming the corporate campus "engineer" due to his relationship being that guy for the CEO.

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pq11333@reddit

Sounds like a peach worthy of eating. I help seniors all the time with their silly cute problems that take seconds to resolve. A man of his stature, i would def help. He sounds connected and well respected...you just never know.

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unknownbiosign@reddit

Lmao this is a real question that a real person asked? You typed all this out and still wonder if you should help the old man who helped you come up? Wow people sure are strange af. Help him jfc

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AverySchmuck@reddit

“There’s this homeless guy who opened the door for me EVERYDAY of the year. He would randomly detail my car while I was working. We’re talking professional grade (WAX AND EVERYTHING)! He must have been a detailer before being homeless. He’s told me I dropped my wallet a couple times when I clumsily dropped it pulling my keys out to get in my car. Which brings me to why we’re here….yesterday he asked me for $0.25. I never asked him for ANYTHING! Should I really be obligated to give him a whole quarter?!!?”

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Beneficial-Poet2911@reddit

Make a stink! It is best to ruin your career over 5 minutes weekly technical support!

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Huge_Strain_8714@reddit

You owe him a day's work for a day's pay. Ask him what his billing address is so you can send him your invoice.

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FloMoore@reddit

OP - you owe this man Nothing. He didn’t freely give you the things you have. You worked for a successful company that treated you well - you Earned what you have. Take the elephant & walk it out of the room. Acknowledge what is undeniable - you are providing tech support. Retirement doesn’t mean your schedule is wide open - suggest you meet at a particular time on a certain day, something regular. Then - charge him for your time. If he didn’t already find your knowledge valuable, he wouldn’t contact you. Good Luck!

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eragonawesome2@reddit

Consider the absolutely banger holiday parties you'll get invited to and introduced as "And this is the guy I call when I need help from someone I can trust" to other potential business owners/connections. Not saying that should be the end of the conversation but like... Definitely worth considering

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bkrank@reddit

My response is two parts: First, employers are not doing employees a favor by hiring them, paying them, putting food on your table, paying your rent, buying your truck, etc. The employee/employer relationship is a balanced one - you provide services to the company and you get paid for those services in return. Both side equally benefit. It really grinds my gears when employers act like they are providing some sort of charity to their employees. They arent' some benevolent God and employees are unprofitable servants. Second, if you have a good relationship with this person, if he's your friend, if you have the time, then help him just as you would any good neighbor. If at this point, there is an advantage for you to provide service to him, such as networking, future job opportunity, etc, then do it. But not because you owe him.

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mtn_doo_codebrown@reddit

I do think you have a valid concern. Setting up devices and helping with tech for boomers is honestly a difficult task. It does genuinely seem like you are happy to extend the courtesy of helping him. However, if you become the go to guy for him, he won't likely stop asking. If he doesn't have kids or anyone around to help he won't have anyone else to turn to. I would maybe just start setting boundaries, like saying "I'm slammed this week, I will try to get to it by the weekend" or "I am working on a big project and won't be of much use for the next two weeks." Once he starts seeing that it's cutting into your time to help, he may get the picture and stop asking as much. Or, he will seek help elsewhere if it's taking you to long to respond. Sort of like quiet quitting. Helping out here and there is reasonable, but weekly is a bit much.

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atreidesphoenix@reddit

Yea man, sounds like maintaining a friendship with a CEO could be beneficial for you in the future. Even if he's retired. The contacts alone.

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ocean365@reddit

You gotta help him bro

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CK1026@reddit

Is this rage bait ? This guy gives you 5 figures yearly bonuses and you're bitching about a tech support call per week ? There are people working 40hrs/week all year round for a third of just your bonus.

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bmaanndd@reddit

Yes 100% you do right by that guy until his Witt’s end. You never know what kind of opportunity will arise for you years down the road. He knows you’re doing it for free. Sooner or later, it will return dividends to you

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Similar_Library_8213@reddit

there might be a day in the future you will once again need him for something, 1 hand washes the other. He seem pretty cool, id keep him as a friend

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InertiaInverted@reddit

If he put a new truck in your driveway, gave you multiple raises and has basically never said no to you. How can you actually think this is a problem??? He clearly only trusts you. As someone who’s gone through something similar. Just be there for him. He might just also want a friend to talk to.

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LeGreen1995@reddit

Stop being a narcissist. He’s done a lot for you financially. It’s the least you can do. Prime example here now that he’s no longer with the company “what have you done for me lately”.

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Sea_Fix5048@reddit

I would do it, and I’d also take him to coffee or lunch or something. Retirement is a tough transition, and he seems worthy of friendship.

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shotcaller77@reddit

He seems to have made a big difference in your life. I don't see how being his tech support once a week is much of a payback for all that. I wouldn't even think twice about it.

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PulseMasterMD@reddit

Hey, if someone is looking out for you that much... You look out for them back.

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Chirsbom@reddit

Sounds like your are in the line for some inheritance? On a serious note, seems like you owe him a lot. Maybe try to teach him while helping? Drop in a line that one day maybe you wont be available. Also, one day you might need his help again, either for a reference, backer on a loan, introduction to a new job opportunity.

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Tibryn2@reddit

Really?

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cleanforever@reddit

Besides your time, what are you losing by giving him a hand here and there? It sounds like there is more potential upside to being in their good graces.

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Decarue@reddit

Sounds like an intern job.

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betadonkey@reddit

People like this never really retire. Just let it play out for awhile. The contact is valuable and you never know what might come of it.

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Khorne29@reddit

Bite the bullet, help him. He helped you, and will if you need again (even if he retired).

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Ollyoops90@reddit

You did your job it's not a favor to keep your job you are worthy of what you did, he needs to know your boundaries too. There will be sometimes where you cannot help everyone, in the end you will not be happy.

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SomeGuyClickingStuff@reddit

Have you ever done this favor before? I was once in a similar position. She wasn’t a CEO but was a C Suite executive that retired. I went to her house and just helped set up a printer as a favor. When I was leaving, she said she knows how much I made and proceeded to give me cash that was more than double my hourly rate. She asked me 2 more times after and always gave me cash that we never even discussed.

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What-a-cl0wn@reddit

Help with his stuff. And do it with a glad and giving heart. You will likely get back from that relationship 10 fold what you put in.

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Liontamer67@reddit

Keep helping and add lunch or dinner to hang out. You’ll build a better and rewarding relationship that way.

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MissiontwoMars@reddit

When someone powerful finds their way into needing you and has demonstrated that they recognize, value, and reward your contributions your only currency back to the is loyalty. Keep helping them, I’m sure it will benefit you again somehow in the future.

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Most-Major-4653@reddit

Time to pay him back for supporting your endeavors!

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jasno-@reddit

You just help him. It won't be forever.

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WasteProfession8948@reddit

Don't look at it as "helping with his shit occasionally", look at it as being there for a friend who was there for you when you needed him. He's also likely adjusting to retired life and reaching out to you provides a needed social outlet. The tech provides a built in excuse for the outreach.

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BicentenialDude@reddit

Apparently he thinks you guys are friends. He may still have some pull. So treat him like a friend with connections. If there’s an issue with work, I bet he’ll be there for you.

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BitzLeon@reddit

I'll sound manipulative but keeping him in your good books is generally a very good idea regardless of what you're doing. People such as that tend to have connections, and it sounds like you have a good friendship with him going, so you can probably leverage his influence at some point.

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Mean-Classroom-907@reddit

I’m in the same position. I always help him. If it’s crazy complicated I’ll say that I need help etc, but it’s usually just storage on his iPhone or some easy stuff you can google. Networking is important, old CEO will probably have the new CEO’s ear as well… always help the VIP’s and if they’re a good one they will help you out.

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GatePorters@reddit

You think he would have made this post about being uncomfortable giving you raises and bonuses sometimes when things were tight? No doubt. But he still did it because he knew you were competent and trustworthy. Now that he’s older and retired, having people within reach who are competent and trustworthy can be the difference between misery and bliss. You don’t understand how valuable your position makes you in his life. You are single-handedly improving his quality of life post-retirement when people start to stagnate and decline. For comparably small effort, you have a lot of power to improve the life of another. It sucks and all, but you’ll miss him when he’s gone, huh?

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ShiftAfter4648@reddit

"Guys, I have an ex boss that notably provided me a positive workplace environment AND substantially boosted my professional career... How do I tell him I don't do IT work for free when he calls about basic tech questions? I see him twice a year and his friends are now providing me opportunities for additional income. Oh, and he is the primary shareholder, his name is on the building, and Christmas bonuses signed by him broke 5-figures." ...bruh

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Thaeland@reddit

I've been in IT positions for years and have experienced exactly what you described. My experience with the top tier leadership of companies is even after they "retire" they will continue to have influence in the company for years. They usually have a significant amount of company ownership through stocks and are friends with all the other top tier people there. It's always good to have a friend at that level in the company when things go downhill and you need their influence. Don't burn bridges.....

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FollowTheDick@reddit

He sounds like he did a lot for you. It’s not a shame returning the favor, help him out and be his friend.

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BrainWaveCC@reddit

>now I feel like I might be personal tech support for life. For someone who has been instrumental in your career? There are far worse complaints in life. This is one aspect of networking. Next time, **after** fixing his next issue, ask if he can recommend anyone to you to help you as a mentor in your next phase of career growth. I continued to help out several senior execs over the years, and they would periodically introduce me to people in their circles who were in need of full-time or consulting work. Don't misunderstand and jeopardize what you have here.

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Cultural_Stuffin@reddit

He retired but is he still a member of the board. It never hurts to have friends in high places.

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COD-O-G@reddit

If he founded the company he likely still owns part of it. What’s it matter if it’s during work hours anyway ?

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bojustice2323@reddit

champagne problems…

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chriscringlesmother@reddit

I’ve offered and helped may people who have since retired or left to move on to different things. I’m not one of these “I don’t do anything for free” types,I just help people because I have the capacity to do so. If the guy isn’t a dick, help him out. He can probably afford to pay anyone, but he’s asking you, most likely because he trusts you not to duck stuff up, not because you’re a soft touch and potentially free ?

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Visible-Meat3418@reddit

Dude seems to be cool. Help a guy out

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IdenticalTwinCO@reddit

You just bite the bullet and accept that you'll occasionally have to help him with his shit. And make sure the CTO knows about it.

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Beautiful_Chef8623@reddit

He may really enjoy your company and this is a way to stay in touch.

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Duedroth@reddit

Does former CEO have close family? If not, from what you describe there’s a non-0 chance you’re in his will. Suck it up.

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Golden--@reddit

I mean he's approved multiple large raises without hesitation and given you 5 figure bonus's every Christmas. Sounds like he did you a solid because most people will NEVER have a boss like that. As long as we're not talking major projects, I'd just help him out.

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HikaruDaly@reddit

This guys seems like a genuinely good person who just needs personal IT help and trusts you. You seem like a dick who thinks all bosses and employees are drones with no value outside of work and only bootlick at work so you can get places. A smart guy would ask him if he’s okay with paying a consultation fee as you are still working & your time is valuable. You’re neither a smart guy or a genuinely good person, just another Reddit dipshit lol

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katet_of_19@reddit

As someone who is a firm believer in boundaries (C-Suite are notoriously suuuuper entitled) and "I'm being paid to help *current* employees," this is different from the scenarios I usually find myself in. Your old CEO sounds like the real deal; someone who doesn't just believe in building a company but in helping his employees improve their lives. He seems like someone who doesn't just recognize and utilize talent wisely, but recognizes contributions and is quick to reward them. The funny thing about execs who retire is they often find themselves bored and in need of a new project or purpose, or their friends all of they know somebody they'd recommend. Sometimes it's a new business venture, sometimes it's a charitable foundation, but there's likely something in the future for him or someone in his network when he's going to go "y'know who I could hire and know that I never have to worry about my stack? u/oaomcg would crush this." Just based on your short description of this relationship, I would definitely make myself available to him for a long time to come, and do so with an air of gratitude, respect, and friendship. This isn't just an ex-employer, this is a professional relationship. I would recommend continuing to cultivate that, personally.

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Heavy_Law9880@reddit

You don't owe him shit. You did your job and he paid you for it, that's it.

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trusound@reddit

For me there are two things here. How much time are you spending helping him and does your management know? I always help people if they are respectful and appreciate it.

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imhereforthesexand@reddit

I know this isn’t what you’re saying but I live by this sentence: “Never step on the toes that’s connected to the ass you might have to kiss”.

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AmazingGinsu52@reddit

Never burn that bridge, based on what you have described.

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eirpguy@reddit

Bite the bullet but set set boundaries and stick to them

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CombinationKlutzy119@reddit

Buddy, i'd workout a way to help the Guy out in your spare time. IS It too much of a bourden? I mean, if it's something that happens like once a month, i mean, why not? There's no trouble just helping out, expect nothing from It, but It could eventually lead to something good. Life goes around a lot, and It doesn't hurt one bit to have a powerful friend sometimes

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Cooladjack@reddit

Sound like a friend, if my friend called me with help on his ipad, computer, personal, etc id do it for drink/food. Now i woudnt drop anything on a dime, but id do it on a weekend or smth

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Ambitious-Traffic121@reddit

Help him out, but leverage the relationship when needed. If he fails to ‘quid pro quo’ then ease off a bit, or he might naturally if he doesn’t want to reciprocate. Also, when people retire - especially from roles that they are deeply entrenched in, it is hard to go from the constant buzz to total silence. He is likely navigating that, and reaching out provides normalcy - it will likely taper off. He is trying to stay in contact with you, but may not know how to relate without having to leverage your work expertise.

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Gubzs@reddit

He can afford paid help. Never become the free IT person, you'll regret it.

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No_Corner805@reddit

I'm going to give a different persepctive - retired or not, he still has ties and pull with the company. It's easy enough for word to get around, for person b to suddenly be supporting the 'former' ceo, and for little things like work, projects, and even prefered days off to get pushed to person b. Not enough for you put 2 and 2 together immediately. But I promise you, given enough time, you'll start to see it. My advice - help the guy out for a little while. Especially if he's still involved with the company. If it's minor issues, let the former ceo know that you're unavailable. But person b can assist with the issue. That way you don't burn a bridge, free up your time, and don't lose soft perks - the perks no one talks about and are unwritten on your contract but provided via verbal agreements and social contracts.

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Axlis13@reddit

Retirement doesn’t stop influence, as long as you were on friendly terms, I’d continue to help unless it crossed some weird boundary, but that is relative and up to you what that boundary is, sounds like it may have been crossed for you. I’d be as pragmatic as possible, good licks

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LooksLikeAWookie@reddit

Sounds like the type of relationship many would die to have. Guess who is top of mind if a better IT opportunity comes to his attention?

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scarletjake@reddit

Why would you say no? Take every moment you have with the guy, and ask him how to raise your trajectory at the company. He'll not only give you good advice, he'll be aware of your desires and advocate for you behind the scenes. The fact that I even had to say this means you might not be worth his mentorship.

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brdblkguy@reddit

Honestly I'd just help him out occasionally. I work in IT support (helpdesk) and the person who built our company built it through business relationships. The companies sometimes leave, but the founders/owners occasionally call in for help. They are usually all super nice and appreciative and were not the people that made the decision for our companies to split. Usually that help doesn't take long either. Grand scheme not a huge time investment, and there may be a networking opportunity for you.

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queen_surly@reddit

I'd consider this something you would do for a friend or an older family member. Get to know the guy now that he isn't your boss. It might be a great friendship.

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britsybaby@reddit

I mean its always good to figure out what your boundaries are in any relationship but I think you need to define the relationship in order to set those boundaries. I'd also recommend a conversation with him if youre having trouble defining the relationship.

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Lopsided-Photo-9927@reddit

It seems like a decent relationship. I’d help out but always on your own time. If he calls and needs help immediately, that’s when you say “I’ll get back to you in a few hours.” It’ll slow things down.

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Obvious_Wind7832@reddit

Just help him out, look he probably still has a ton of influence in the company. The happier he is, honestly the easier your life will be. When you're bored and retired. All you have is time to think about people who scratch your back and those who abandon you. All the time in the world. It'll be best from time to time to help. Just think of it as doing some kind deeds for the year.

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mediocrity4@reddit

People dream of having friends like this lol

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bsrichard@reddit

Like many have said, I would continue to help assuming the guy is chill about it. Make sure that you only help when it is convenient for you. If it isn't, be straight up about it that you can't do it now but will later. Especially if he could prove useful in furthering your career with connections or advice.

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madmancryptokilla@reddit

I've been self employed for little over 25 yesrs and these kind of guys are hard to come by..I have 2 and I'm there on the drop of a dime if they need any work done. It sounds like he's done a lot for you.. I'd say bite the bullet.

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oneofmanyany@reddit

You need to tell him what your hourly rate is. Make it worth your while. We had the same situation with a CEO who retired. How did these idiots get this far along in life without knowing anything about IT.

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Busy-Blacksmith-2009@reddit

I think he misses OP. The transition to being retired may be getting to him and contact with a familiar person may help him. My first job interacting with seniors and retired people taught me that a lot of people would call and ask for help just for the human interaction. I always take time out to help people even when it seems like a small meaningless thing because you never know what it means to that person to have someone take time out and acknowledge them and help. Along as it not keeping you from something more pressing give a friend a hand (or a stranger).

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yomeratz@reddit

Stop thinking small! Think about career advancement and call him back with questions, mentoring, introductions, etc

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beigemamba1080@reddit

You get to chat with and help the guy who has done you years of solids for a few minutes once a week, enjoy the bond before it’s gone and make sure to go visit him and fill him in on all the workplace drama once in a while. This is time spent that you will never regret when you’re older which are nice finds in this crazy world.

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ConstitutionsGuard@reddit

Slowly increase the amount of time between when you say yes and when you actually do something until he’s calling you less.

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MammothReal6014@reddit

This basically translates to “my steak is too juicy and my lobster is too buttery, but I have to use a fork and knife to eat it🙄”

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Competitive_Two_8372@reddit

Dude, this is one of those situations where you just do the thing. Need a printer hooked up? Do it. Install an app on a phone? Do it. Got a new tv and doesn’t know what HDMI is? Do it. It’s in your best interest.

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Few_Recover2437@reddit

When someone retires and they are a hardworking dedicated employee it is pretty common that colleagues will continue to go out of there way. Imagine how much history and knowledge this person has and how many people are reaching out for advice or information. Guaranteed it's happening and he's retired- Meaning he's answering his phone for free. If you stayed and retired and you shared your knowledge wouldn't you hope someone would extend help back to you when needed.

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NewMilleniumBoy@reddit

At this point honestly he kinda seems like a friend. Treat that as you will.

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grvlrdr@reddit

Could you try emailing him a bill for services and see if it opens up a conversation?

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snakeiiiiiis@reddit

I don't understand the problem. Are you having to drive far out of the way, or does it cost you money to help him? Unless he's a full on nuisance of a human which he doesn't sound like I'd be helping. And my guess is after you fix these couple things it'll be a while til he needs something else or buys something new that needs assistance. If it's on company time, even better. But if it's on personal time tell him "I have to help son with something first then I'll be able to help" and it might remind him that you have a personal life.

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WatchTheGap49@reddit

Stay loyal to him.

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dunkeyvg@reddit

You aren’t playing this right, this is a relationship you keep as it can become an opportunity for you in the future, especially since he likes you. Maybe in the future you start your own business and he may help you with money and connections

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Spright91@reddit

I would probably help him if I had a personal relationship with him. Seems like a good guy to have as a friend.

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thisoneistobenaked@reddit

This is an enormously valuable contact, both for your current role and for connecting you if you ever move out of your organization, and that’s beyond what he’s already done for you. I would 100% help him out every couple of weeks, and turn it into a lunch/chat/stay connected. For all you know this might be his way of staying in touch with you.

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Zane42v2@reddit

Why wouldn’t you? He’s impacted your life by many thousands of dollars. He still has influence on where you work. You’re looking at this all wrong. This is an opportunity to influence change where you work which could be beneficial to you and the company by using the time to provide input to him. Get his advice on moving up the ranks or pursing the next thing you want to accomplish. You’re being very near sighted and a little ungrateful. Most people pay big $ to have face time with a person at that level.

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yogaelephant@reddit

This is so easy. Just help him out. Geez. It may even pay off big for you in ur career. He still has influence even after retirement. But that aside, help him and expect nothing.

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ebsf@reddit

It won't kill you to help a guy out, for starters. And, you've got a prominent founder / CEO who calls you? I guarantee you there are people who would do nearly anything just to be able to reach him. This is a golden relationship. If anything, cultivate him. Be really happy when he calls and super-easy and agreeable. Find out more about him, what he's doing professionally or for fun, and his family. Clue him into what's going on with you and your aspirations. Ask his advice. See if you can't work toward having breakfast, lunch, or beers with him periodically. It doesn't sound as if he's being too demanding or grossly violating any boundaries, you're just his guy. He knows he's asking a favor and building up chits. If this needs reinforcing, you can always put some minor brakes on things, like, happy to help, I've got a meeting, can I get back to you in an hour. I wouldn't put too fine a point on it, though. Just be his guy.

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ArugulaCareless8593@reddit

As someone that got stuck as the family's free tech support for years I feel your frustration. Most of the times when this happens there was this sort of implicit assumption that you were going to help and give your time/energy and energy materials for free. That doesn't quite sound the same as this case so you probably need to think about how you want to handle it but just doing it is probably worth the pain. An alternative is to do what others recommended and help get something set up through the company where the company provides tech support on company time. That would probably be better all around

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gogenberg@reddit

dude I only made it to half way but it sounds like he's more than just the CEO that helped you out and treated you well, seems like he likes you and you like him, it's a type of friendship.. It's a tough call but if its not actually too much hassle to do it I'd bite le bullets

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alexromo@reddit

“I’m very busy, I had to pick up a side gig to make ends meet”

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Status-Biscotti@reddit

Have you read what you just wrote? Quit whining and help the guy out.

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woemoejack@reddit

Certainly a judgement call to be made. 'I feel like I owe the guy a lot' - Why is that? You were doing a job and the company was paying you. You probably did good work and he was, albeit uncommonly in this field, appreciative of that. 'The business he built helped put a new truck in my driveway and food on my family's table for 5 years' - Not for nothing, though. They paid you for the work you did. You worked for those things and earned them. You wouldn't have done any of those things for free, and they wouldn't have paid you for not working for them. I've had plenty of bosses from old jobs that did what they could for me and more while I worked there. Some of them I still maintain social relationships with. I've done plenty out of band support for some of them while I was employed by them. I'm ok believing I don't owe them anything else once the work relationship came to an end. Do you believe the future relationship will be beneficial to you in a tangible way? If he's such a great guy is he going to badmouth you to his old coworker executives or fire you if you refuse to do free work?

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Vibe-Codine@reddit

Help him out because it sounds like he’s a good dude. Also, having a former founder/CEO you are friends with can be an extremely powerful part of your network.

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rich_evans_chortle@reddit

Dude, just help him out it's not like he's asking you to go mow his lawn.

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vwaldoguy@reddit

I'd say it's a small price to give back to what he gave you. And the amount of help he'll need will probably diminish with time. People like that might be good to keep in the friend list. You never know when you might need some connections.

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fwilsonator@reddit

Are you still young in your career. If so, you can not have too many friends...

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CoCoNUT_Cooper@reddit

Raises? Promotions? Bonuses? Tech support for life

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Hot-Nefariousness187@reddit

I would not work for free. He never did that for you.

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Responsible-Ad7531@reddit

I’m gonna be real. Keep him as a friend. Rich people have a way of making their friends rich. Money knows money.

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KOxSOMEONE@reddit

This guy treated you right for so long. If I were you I’d be happy to help him with little things like this whenever he asked me.

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ilikeror2@reddit

Had this opportunity with an ex CEO. To be honest I actually loved helping him. He’d invite me for a beer, cook steaks, invite my family over during pool party days, etc. Super cool and down to earth guy. It’s your call of course and if he annoys you then politely decline.

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doozy-kitten@reddit

Don’t be a dick

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vabello@reddit

Based on everything he’s done, I would grant him the equivalent of family level tech support for life.

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kirashi3@reddit

While I understand what you mean, careful... Some people's "family rate" is triple what they charge their regular clients. ;) If former boss dude is respectful of OPs time outside of work and makes a valiant attempt at _trying_ to solve their own problems before contacting OP, then it sounds like OP should keep helping them. However, if former boss dude expects OP to reschedule their life to help with reading a message telling boss dude to click an OK button, I would eventually reconsider being "available" if I were OP. Everything in life has value, including former work or social connections. If the value of those connections becomes outweighed by wasted time, keeping those connections may not be worth it.

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AdorablePiccolo8850@reddit

It’s ok to set boundaries, even with people who have helped you in your career or are meaningful to you. It might be good to develop a new type of relationship with him- it sounds like you still see him as the big boss and so it’s hard to set boundaries with him like a normal person. But he is kinda relating to you as a friend now, kinda like how boomers will call their kids when they can’t figure out the tv. Sounds like you want to stay connected to this person, so I would say, follow his suit and see him less like a boss and more like a former boss, current friend. Let him know if the house is rowdy, your wife needs help, you’re busy, etc. he can pop by at this time for help, come over after the kids go down at this time, buy me a beer and I’ll help ya with your emails, that kinda thing. He’s not your boss anymore and you get to let that relationship evolve. It sounds like the other guy is ready lol. You can also just let him know you can’t. But I think letting him see the “why” is a kind thing that helps offer context like you would give a friend if you couldn’t help them with something.

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SiThreePO@reddit

Are you serious? Help him the out... green lite raises...

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Gullible_Flan_3054@reddit

I would personally continue to respect the relationship and provide support so long as I'm working there whether he is or not.

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AntonChigurhWasHere@reddit

Ive done more than that for people that did less than that for me. $10,000 ( or more) bonuses broken down could be mentally thought of as 40 $250 iPad tech calls. I understand bonus was for your work then but he threw you a few bones so I’d throw some back to him. If it makes you feel better go hang out with some drunks at a bowling alley and see how that helps you grow mentally and financially. When you do him a favor use it as an excuse to pick his obviously successful brain for some ideas that will help you long term.

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battlehamstar@reddit

Is he still a shareholder? Does he still have C-Suite friends? Give me his info; I’ll be his tech support.

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lajaunie@reddit

I was almost rooting for you until I got to 5 figure bonus. Maybe I’m just loyal, but I’d do his wife if he called and asked

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U_HWUT_M8@reddit

Build boundaries, have an honest conversation with the guy. If he respects you he’ll react well, if he doesn’t respect you then he’ll be an ass and you can proceed from there.

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StudleyTorso@reddit

Yes. He earned it. Please put some care back into the pot! Good man!

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UnethicalFood@reddit

CYA: Make sure that you get in writing from the current powers that be that you are allowed to do this work for him, because sooner or later it may cross a line you have no way of knowing exists.

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CyclopsorNedStark@reddit

If the CEO or my company retired and asked me for a favor once in a while, I’d be happy to do it. I think you should too.

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davcarcol@reddit

Kiss the ring, he still has connection power.

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Eatyourcheeseburger@reddit

I keep in contact with a couple of former bosses that I’ve had that treated me well. They’re always willing to provide a good reference, and I try to help them out when I can. You don’t discard people after they’ve been consistently good to you just because it’s time for you to return the favor, imo.

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mr_j_boogie@reddit

Generous boomers get a pass on the whole not good at tech thing. I love watching my dad navigate on his iPad, he kind of puts a finger in the air for as bit as he decides what his next e-move will be. He's such an awesome dad. His birthday card to me said "I know I must be an old fart if my youngest son is turning 40..."

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CorrectMasterpiece55@reddit

Not the CEO but the CFO of a large company I used to work, he called me like a month after his retirement asking for some tips on setting his home network and I told him "we can do this in two ways; 1. You put the beer, food and materials and I do the job or 2. I'll charge you with friends and family rate. Tip, I would choose 1". While working together he was one of my two lines or reports and we always had a really healthy work relationship. Depending on how close you are with the CIO, I would use a joke like this

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PlatypusStyle@reddit

You are allowed to set boundaries but maybe your boundaries don’t have to be all or nothing? For example a set time or day to deal with all his questions? It’s also possible that he’s feeling lonely after retiring so maybe you could suggest having coffee and dealing with his questions and a bit of socializing.

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SlowPokeInTexas@reddit

If it were me, I'd bite the bullet and keep doing it.

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Own-Hamster-7846@reddit

Who knows, maybe one day he will get you on the path to being a CEO for the company if you are thought about that much by him. I’d keep helping him honestly lol

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Iaintgettinyounger@reddit

Find him a small IT business he can trust with this stuff, because you might not always be able to help him in a reasonable time. Then just help with some of it and suggest the IT business for the rest.

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Doctor_Mothman@reddit

If you can do it - do it. If you can't, use it as a jumping off point to recommend Geek Squad or something else. Remind him that things change fast in the digital world and that your area of expertise is starting to diverge from his unique needs.

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lowrespudgeon@reddit

So you can write a whole paragraph about everything he has done for you to help establish your career, and yet not see how lame it is that you're complaining when he asks you for small favours?

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Open_Appointment1091@reddit

Why is this even a question.

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prime_run@reddit

Continue to help. He’s a friend and valuable career resource to have IMO

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Corey307@reddit

OP this guy took care of you. He doesn’t sound like the typical boss, he repeatedly hooked you up and valued you. You think you could give him a little attention once in a while.

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Tax_Evasion_Savant@reddit

> I feel like I owe the guy a lot. Stop feeling like that. He became CEO by stepping on necks, his huge paychecks are at the expense of other people, you don't owe him anything, **HE** owes everyone in that company **everything**.

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Blue-Thunder@reddit

Sounds like you're being an asshole. Not going to sugar coat it. The man went to bat for you for YEARS, and just because he retired and can no longer forward your career, or so you think, you just want to tell him to basically "fuck off". WTF is wrong with you.

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ClassicWelcome9369@reddit

Dude... connections are everything in life and business, I would 100% help him out

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Odium-Squared@reddit

Just don’t answer the phone ;)

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Miserable_Song2299@reddit

>He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. ayo, this guy is looking out for you. if all you have to do to pay him back is help him configure an ipad, do it. if not, give him my number and I'll do it.

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PrimeIntellect@reddit

Tell him he'll do personal tech support for him and set up a separate contract, I can assure you that a guy whose name is on the building has the money for it, and would be willing to pay it for someone he knows and can trust

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1290_money@reddit

This is not a relationship I would burn.

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Extra-Presence3196@reddit

Yes. No.

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YourItalianScallion@reddit

If this guy treated you like garbage I'd say block his number, but considering he seems to be one of the "good" bosses... in your position I'd just suck it up and help pee paw with the iPad forever lol.

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gingerinc@reddit

If you say no, you will be performing a career limiting manoeuvre. As he will know people still there, and he will make a call to someone. Don’t be silly for the little effort.

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Brainpry@reddit

Idk what the issue is….. he sounds like a really cool guy and not to be rude, but idk why you’re even complaining about doing it. I’d be HONORED to help someone like that. In this world of greedy CEOS, and POS bosses… what you said he’s done is amazing… in fact I’d delete this post and never mention it to anyone just in case someone sees it and puts 2 and 2 together and tells him.

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BeenWildin@reddit

Just learn to set healthy boundaries. You can say yes to somethings without having to say yes to everything.

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Dratinileft@reddit

I would continue to help him out, nothing seems like it is a heavy lift. Dont burn a bridge for someone who appreciated you.

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TheTapDancingShrimp@reddit

Pls help him. Older, low-tech person here...you don't know how much this helps someone like this.

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Mundane-Basil-8924@reddit

Help him out, I mean don't drop everything when ever he calls, but help him out.

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Still_Conference1932@reddit

Put a price on “yes”

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Late-Alarm9194@reddit

Sounds like he's just getting a personal life after a successful corporate career. Also sounds like he's helped you out along the way, which is in today's world, extremely rare. Help the guy out, it's not going to be "forever".

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Benefit-Zestyclose@reddit

The policy in our IT department states that we are not permitted under any circumstances to work on employees' personal equipment. Prevents any liability issues.

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shockwagon@reddit

i'd bite the bullet, what is it, 10-20 minutes at most a week? He knows people, and networking is the easiest and best way to earn more money or get a better job

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KickedAbyss@reddit

Does he pay you on the side? If so, sure. If not, eh... Hard call.

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ever_falling@reddit

I find it concerning that you could not have simply reached the conlusion on your own that its best to continue helping him.

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ez12a@reddit

If this was someone who had done nothing for me while employed I would say let them down gently, but sounds like they did a ton for you, esp the raises and promos. Agreed with others: bite the bullet and do it as a token of appreciation for them.

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Spor-T@reddit

Hopefully you are not just helping him but also teaching him. Also it is not out of line to send links to videos that contain the solution or possible solutions he may try first on his own. I generally say: I am driving to "anywhere" or "I am at a 3 hour workshop/seminar". In the meantime, here is a link to a solution (or possible solution). Many times they text back saying "That worked". It gets them to start looking things up FIRST on their own without calling you every time.

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kirksan@reddit

I get calls from a few people I haven’t worked with in decades. They dwindle over time, but helping them is a nice thing to do and it’s good to keep in touch with folks. You’re your former CEOs lifetime support person, you should feel lucky to be chosen and help them when you can.

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meSabina@reddit

Bite the bullet and help him out when he needs it. It's good Karma.🌷

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Pure_Property_888@reddit

A quick, concise "MEEP!".

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kjsd77@reddit

Sounds like he thinks of you as a friend. Probably a good person to keep around in your life.

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Budget-Discussion568@reddit

I Wonder if he doesn't really need tech help but is instead trying to stay in touch? Can you ask him if he wants to meet for breakfast/coffee one day & see if doing that lessens the "tech" calls? Sounds like a good person to have on your side.

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badamsb24@reddit

YTA....help your mentor out.

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simara001@reddit

Do I just bite the bullet? Yes.

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Lurking__Poster@reddit

Maybe there's some context we're missing, but from what you've posted... you sound ungrateful as hell dude. This guy took care of you and you can't take the time to help him with some incredibly minor tasks?

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New_Awareness_9097@reddit

If he's a CEO he can afford geek squad. I used to do this stuff for people when I was help desk but after I got to sysadmin level I stopped completely. Covid was a great catalyst to say now. I get this guy helped you a lot and I wouldn't mind every few months or so but once a week is crazy. I would not do it.

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blueberrypancake234@reddit

Bit the bullet and continue to help him out. He's a good connection for you and well worth the time.

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meutragic80@reddit

Help the guy out because it is the right thing to do.

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grumpyoldmedic@reddit

Sounds like everybody is Zane what I’m thinking . There’s nothing in your post that gives a reason not to. Everything in there tells me you should. If it doesn’t cause you much interference with your regular life, heck do it forever. But usually over time it gets less.

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bubba198@reddit

Yep you're indentured bro, there's no escape!

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NysexBG@reddit

Do the old guy a favour. Go to his place and fix the ipad and in the meantime have a coffee or a beer with the guy. Talk with him, ask him stuff. He is a founder and ex ceo, clearly he has brains… maybe you would learn something valuable or take some wisdom. Later on when you need an advice or something ( not money, just advice/tip or something else ) he would return the favour. Be polite and friendly. Spread goodness

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SufficientRatio9148@reddit

I mean, that seems like a good spot to be. Even if he retired, he still has a lot of pull, I bet. And he’s still in position for you to pick his brain on advancing your career, especially at your current company.

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Dredkinetic@reddit

You should probably just keep doing what you're doing. That's what I'd do in your position.

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speed721@reddit

Help that man. It will still be good for your career.

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poopoojokes69@reddit

“This guy gave me everything… Do I really need to go help him for ten minutes a few times a year?” And they wonder why “the village” is dead.

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Ckirso@reddit

Sounds like he scratched your back.So now it's time to scratch his back. I'm not saying that you can't say no to some things. But it sounds like this is someone that you should keep fostering that friendship with.

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hunterderpp@reddit

I would help out whenever if I had someone like that on my side. He helped you when he didn't have to.

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AccomplishedCow6950@reddit

Brother, networking goes a long way. I know it's annoying but just reframe this from a chore to an investment. Be grateful and you might just get a new friend in your life at the very least, and other opportunities in the future.

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UnhappyGeologist9636@reddit

This shouldn’t even be a question. Used to work at a feed store delivering mulch over 10 years ago. If the owner called me now and asked for help getting some work done there’s not much that would make me say no. If you value him and he values you this is a no brainer.

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HellDiver2k25@reddit

\> I feel like I owe the guy a lot You either do, or you don’t, make a choice.

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UncleBadTouch46290@reddit

Charge him for your time, just like you would Anybody else

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jtfjtf@reddit

This man is now your mentor. If you need anything you ask him. And if anyone in the company gives you grief you tell him.

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Antonia_Rothschild@reddit

Bite the bullet. Sounds like a generous, good person. Sounds like he "made" you. Never discount his ability to unmake you. The newly retired are not yet sure who they are and what to expect. They are sensitive. If you have helped others, one day, this will happen to you. If what is asking is not especially your forte, who would you recommend to him to hire hourly? Maybe he has no idea how to get his needs met outside of his old structure. You could say, "Hey, if I am ever not available immediately to help, here is the name of X, who I use when someone is above my skill level, or I don't have time." But continue to assist him, unless he becomes abusively needy.

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AccurateThought4932@reddit

Awwww, please just help him out. It seems as if he is a kind and generous person. Eventually, he will stop asking after he has figured out how to do things himself. Nor would I accept money, liquor, or lunch as payment. Some things you just do for free. My opinion is that this is one of those times.

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White_Falcon_1263@reddit

Brother he sounds like he's done allot for you. It doesn't sound like a lot to help with these small things. Don't burn a bridge, he probably still has a lot of pull at that business. Not that he would but I know plenty that would because they could.

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New_Team9797@reddit

help him occasionally, you'll feel good and he'll think you're awesome

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harmospennifer@reddit

Do not burn that bridge because one day he will be in a position to help you move up even higher… Just smile be friendly, and do it

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cementfeet@reddit

Continue helping. You never know when that card may come in handy.

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bigrightthumb@reddit

Somone here said that he probably has influence in the company. I expect thats true. Maybe think to habituaise something the firm finds hard to turn down. So 'hey senior exec. Old ceo has asked for my help on x. I know we're all supposed to help with the fund raiser Thursday, but maybe I could go help him out ' If you can transition to helping him on company time then its win win. If the company then cant give the time ... its not on you. Moreover you can leverage your free time much more productively as you'll then be helping him despite the company turning its back on him.

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catwiesel@reddit

after 5 figure bonuses I would be hard pressed to find ways to say no. I am not sure it means you will have to drop everything all the time. setting some boundaries in a soft way makes a lot of sense.

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gandalfthegru@reddit

Your personal hours are billable at $500/hr imo. If he wants to pay it go for it.

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sh0gun2006@reddit

If it's really simple stuff like you're describing I'd continue to do it gladly.

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PyroIsSpai@reddit

He sounds as much a friend as a coworker and mentor. If he keeps contacting you, he trusts and likes you. It sounds like you have a relationship that's one of those rare borders on family things. If anyone is safe in any job, it's *you*, as well. I get you're worried about boundaries, but this is the sort of one where you may honestly be overthinking it or over-worrying it.

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Milos42@reddit

Best 30 minutes per month you can spend during working hours ever! Can you imagine you being in trouble and ask for a favour in return?

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Clovis69@reddit

He retired, but obviously still values your skills - its a good spot to be in for networking purposes, if you ever need a letter of recommendation, you are still obviously in his circle of professional contacts.

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eleanor61@reddit

If you had a good rapport before, try to do what you can to help as long as you’re not uncomfortable. Eventually, the requests will subside for one reason or another.

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FckLogicK@reddit

Diga que está muito ocupado com as demandas recentes e que precisa contratar um estagiário, deixe ele apenas para suporte ao ex-CEO rsrs.

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chassieux@reddit

I'd help him. I've always paid it forward to people who were good to me and he sounds like he's earned your help.

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xepoff@reddit

Reread your post. I think you answered it yourself

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Dsraa@reddit

It could continue to work in your favor if you play it right, I'm sure he still has allot of leverage in the company and it's partnerships. If you decide to make a bigger move, become a department head or start your own partnership, I'm sure he'd most likely help in some way.

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paulgraz@reddit

Help him out. If it's a huge time consuming job, maybe quote him a reasonable price.

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Lostinspaceballz@reddit

Think of him as a grandparent that needs your help. It will probably pay off one day and even if it doesn’t, you’re a good person.

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Bodhi_LongBody@reddit

I’d do it, no question. Connections like this just don’t fall out of the sky.

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myloteller@reddit

Keep helping him about. It’s always good to have friends in high places. Let’s say in five years your company turns to shit and you get fired or laid off. I guarantee if you tell this guy he will make some calls and by the end of the week youll have another job making just as much if not more. It’s not what you know it’s who you know.

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AlDenteSteak@reddit

You can still help him while having boundaries. When you can help, help. When you can't or don't want to, say no or ask him to wait a bit. If he's your friend he'll understand. But as others have said, he sounds "worthy"

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threetimesalion@reddit

Man the replies here are a world apart from r/relationships - they’d be telling you to dump this guy and focus on your own immediate needs. Feel like I should hang out here more (and my job is nothing to do with tech)

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BasicallyFake@reddit

The best way to do this is just be honest about your availability and tell him you are willing to work with him on finding the support he needs.

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Cold_Biscotti_6036@reddit

This is a guy I would retain a good relationship with.

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FlyinRyan123456@reddit

Help the man who helped you

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Theslash1@reddit

I've always helped ex upper management with IT after they've left. And now, years later, Im working for one of those guys who started his own company and wanted me. For a nice bump in pay too. Connections matter. Some industries more than others, but whats a little personal IT support on the side if it keeps your name hot.

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dc91911@reddit

If he is not an ahole and you got the time and genuinely like the guy, I would. Career is about relationships. He can open doors.

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terrorable@reddit

You should continue helping him. He is not stupid and knows what he is asking of you. It is worth it to keep this connection for sure, for sure for sure for sure. !!!

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StinkyKyle@reddit

It seems like all the things youve listed that hes "given" to you were actually just things you earned through hard work. Signing bonuses, giving promotions, ect were things that were his job. Now, if he was a genuinly kind person and you liked his company, or if he did things that werent job related to help you out, then you could keep helping him if you wanted to and it could be a way to keep contact with a firend, but from what you worte it sounds like its kinda impacting your free time and you absolutely have no obligation to keep helping. Personally, i would be in the camp of setting boundaries now rather than later. Doing that in your circumstance is tricky, but it doesnt sound like he was an unreasonable boss or anything. Would an honest conversation with him be out of the question?

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BitterConsequence642@reddit

I would help him. Dude sounds like a good guy.

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volitive@reddit

My friend, you could have a CEO/Executive mentor. Ask. Don't forget, his name is on a building but he shits once a day and wipes his ass. He is human. He deserves respect but not reverence. Get lunch, pick his brain, and learn. Ask questions. And don't be afraid.

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Bidcar@reddit

I would help him, he sounds like a great guy.

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WormedOut@reddit

It’s crazy to see Redittors get handed these golden tickets and still need strangers online to coach them on doing the most basic social commitments to keep them

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Paleoanth@reddit

Just help him out. Cripes.

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CTARacer@reddit

I mean...this guy seems more than worthy of that tech support, especially if he is always kind and appreciative

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nsbohn@reddit

Value the relationship and use it as a good excuse to continue that relationship. It will continue to pay off. Also, here's another idea that I don't see anyone else suggesting... pass the torch. Is your son tech savvy and needs a mentor? Is there someone else at work who could benefit from a relationship with said retired-CEO? Make sure they understand the stakes, and then give the old man a "hey, I'm really jammed up with this project, I want to introduce you to this really great up and comer, he's going places at This Guy Inc., I'm going to send him to help."

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EasyGravy420@reddit

Maybe you should pop a joke about consulting fee's.. Be cool about it and see what his reaction is. He sounds like a great boss/guy. Id bite the bullet and answer the calls unless he's really bothering you.

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Alexisredwood@reddit

This is such a ridiculous question, I’m so but it’s clearly a no brainer — keep this guy on side.

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ForeskinAbsorbtion@reddit

Meh, if it's basic shit, I would just deal with it. Guy sounds like a real one.

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kanid99@reddit

If it only costs you time and knowledge, and this person did as much as you said - well me, I'd feel compelled to help them if I could.

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Stormbringer91@reddit

You're so lucky dude. Your relationship with him can only grow. Keep at it.

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Low_Twist_4917@reddit

I’d help him. It’s not rude not to but he helped you at his expense through your career, and helped elevate you to where you are today (yes you worked hard but you mentioned this yourself - experience with him was different than prior history). He can probably help you in a plethora of other areas in life too. Think of helping him as if you’re helping your father or close friend. Ask for coffee etc and chat about life and experience. Never hurts to grow your network and do favors for those who have been or will be in the position to help you as well.

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AlienDragonWizard@reddit

Never hurts to be nice.

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shutchomouf@reddit

You should reciprocate. reach out and ask him for help only he can provide.

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Just_wanna_curl@reddit

Consider that they might be board and bugging you for something small is them trying to get some social contact in without looking small & needy for hangout. If you appreciate his company and would consider wanting to learn more from him, feels like a good opportunity to have some casual hangouts.

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Rebel_Kraken@reddit

You’re complaining about once a week after all you just described? I’d be over at his house setting it up for him. Super sad.

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Apprehensive-Base929@reddit

*“I’m always happy to help when I can, and I really appreciate the trust. I’m getting pulled pretty hard on work and family lately though, so I can’t always jump in ad hoc. If it’s cool, let’s either batch things or I can help you get someone you can call anytime.”*

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akajondo@reddit

Honestly I'd just continue to help him from time to time if you ever need a new job or something he probably still has a few contacts that can help. My wife keeps in contact with her old CEO and its helped alot with job opportunities. These guys retire anf still hang out with other buisness owners.

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Stuartburt@reddit

I think you help him. It’s a great way to continue the relationship and you never know, he might get bored of retirement and decide to go back to work and will hook you up in the future. Either way, he sounds like a guy they would be nice to stay connected with.

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augustwest2155@reddit

FFS, help the guy out. No brainer....

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7days2pie@reddit

It’s called gratitude.

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GinnyJr@reddit

It’s not about what you know it’s who you know Play the game and help him, never know what job he could get you

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Apprehensive-Base929@reddit

I’m always happy to help when I can, and I really appreciate the trust. I’m getting pulled pretty hard on work and family lately though, so I can’t always jump in ad hoc. If it’s cool, let’s either batch things or I can help you get someone you can call anytime.

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Apprehensive-Base929@reddit

“I’m always happy to help when I can, and I really appreciate the trust. I’m getting pulled pretty hard on work and family lately though, so I can’t always jump in ad hoc. If it’s cool, let’s either batch things or I can help you get someone you can call anytime.”

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valryuu@reddit

I think given the situation, the way I'd go about this is to help him still, but set boundaries and limits for the urgency and priority. Like, maybe tell him that he can't call at certain times because you're with family or at work. Or if he does, that you will get to it after finishing up some higher priority things. But I would continue to still help him, unless it becomes much more frequent.

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Lightoscope@reddit

Bridges require maintenance. Help him out, and take him out for a beer, or whatever. He’s probably bored.

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BinniH@reddit

Sounds like you kinda owe him, just do it on company time.

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airinato@reddit

Welcome to IT, where if you want a good reference, you'll be doing base level troubleshooting for the rest of your life.

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bazilbt@reddit

He might be reaching out for interaction more than actual tech support. Sometimes retired people have trouble knowing what to do with themselves.

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TehNubbins@reddit

You’re shooting yourself in the foot if you draw that boundary. Don’t.

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dr_z0idberg_md@reddit

Wow, I have been in a very similar position before in my past. The dude even invited my now-wife then-girlfriend over for meals with his family. He would hit me up for random tech issues once a month or so. I just bit the bullet and helped him. It wasn't anything too crazy hard, and I always responded on my time. After about a year, the calls came less frequent. We still send each other Christmas cards, or we'll grab some lunch with former colleagues when he is in town. Your call really. As some people mentioned, he might still be able to help your career or give a glowing letter of recommendation at the very least, and he has been so impactful to your career.

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mowtowcow@reddit

I agree with the people saying of he helped you, help him. But once a week is a bit much. Every single thing about an iPad can be googled. Every problem has been had. There's not a single problem that cant be fixed with a Google search. Teach a man to fish and all that. Seriously, teach him how to use Google. He will benefit so much more than you just helping him every time he has a problem.

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_super__sonico_@reddit

after reading your description of the CEO, I'd also take the guy to the doctor if he'd need it.

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MavZA@reddit

I’d say you need to establish “office hours” with him if you decide to assist him. Seems like he’s done a lot and define a turnaround time that he can expect. Just to make it clear you want to help him but it’d be out of your nine-to-five and encroaching on your personal time.

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Standard-Fudge1475@reddit

Can you help him out during work hours?

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HurtsWhenISee@reddit

Sounds like he views you as a friend. His influence isn’t over and I’d keep him close if you care about your career. Half of success in tech is a great network of people.

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Ambitious_Parfait385@reddit

Nah. Stay engaged. You'll never know when you need him later in life as a reference. Also he may still be a board member. Document your time spent fixing his stuff and make him aware your keeping it.

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Nervous-Wolverine-39@reddit

Buy him for his birthday/Christmas some tech class!

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zeeblefritz@reddit

It has been decided that if you don't continue to help him, you are the asshole.

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userhwon@reddit

Help if it's easy enough (heck, what is everyone doing in here all the time?) but when it becomes actual work, suggest he get the Geek Squad to do the repairs because you just don't have the time or skill, whichever is correct.

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Gandalf_from_3@reddit

Just help him. Dont consider it part of work. Just imagine he's like your uncle or something idk.

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Scouseulster@reddit

He seems like a good connection to have

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billbillbilly@reddit

100% this dude is still highly influential on the company, and you'll absolutely benefit long term if you keep them on yourside. Atleast for the next few years. It is also incredibly likely that they are still financially connected to the company and still involved at a board level. But what you can do, is set and manage expectations a bit. If you are busy with important company needs, then explain that. Think of it as having a well connected and relatively wealthy friend or connection.... things might not be as one sided as they seem.

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deZbrownT@reddit

He seems like a guy you dont want to say no to. Delegate when you are in time crunch, else be happy you have him in your life.

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Buttermilk-Waffles@reddit

It sounds like he's a decent guy and you have a good rapport with him, I'd say give him a hand with his iPad and maybe even see if he'd want to have lunch every now and then. I mean there's no telling what kind of connections he has that might be useful for you in the future with your career.

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Hey_Giant_Loser@reddit

You owe that guy. Delete this post and shame on you for even bitching about it.

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Lozsta@reddit

I'd say that now he isn't paying the cheques it will cost him a little for your time. That can be in trhe form of some beers when you attend of actual payment. You sound like you've had plenty of money from them though...

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Enough_Pattern8875@reddit

I would continue to help him if he’s done that much for me. Ask him what his plans are, there might be business opportunities waiting for you.

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Turbulent-Poem4915@reddit

You'd be dumber than bricks to burn this bridge. Not to mention, he sounds like an awesome dude who has vastly improved your life. God forbid you help him set up an email account after he gave you 5 digit bonuses. Ungrateful.

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throwawayPzaFm@reddit

Ask him out for lunch or a beer. There's a pretty solid chance that he wants to hang out.

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Ed_Runner@reddit

Don’t be stupid. Keep helping him out. He can continue to be a catalyst for your career. It’s about maintaining relationships.

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8DHD@reddit

maybe a chance to start your own consulting biz. trade him business advice for your tech skills and troubleshooting. maybe it takes off?

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DiarrheaTNT@reddit

You absolutely don't say no and you keep that golden coin in your pocket to get you out of getting fired / layed off.

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BrunnWFFC@reddit

Wouldn’t hurt to teach him while you fix him. And show him how to ask Ai.

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Objective_Party5374@reddit

you did not want to help the person who helped you a lot ??

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themanseanm@reddit

Sorry 5 figure bonus checks? My man I don't know if you need some perspective but if so here it is: some people don't make that much in a year. If its not preventing you from doing your job I'd say he already pre-paid for this service.

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ryanhazethan@reddit

Bro just lend him a hand and be a good friend?

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Retlawst@reddit

Remember to set boundaries. There’s only so much time in the world and setting boundaries allows you avoid most pitfalls associated with relationships. By setting time but limiting it, you can control your own engagement without seeming avoidant.

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Puccimane@reddit

People that treat me well, recieve that same treatment from me. Sounds like he always listened, and appreciated your work and compensated you for that. One thing I did for my older relatives who requested the same help. Make a cheatsheet for them, go over the first time and spend a couple hours teaching them how to use this stuff.

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Living_Jellyfish4573@reddit

bite the bullet.

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UnicornsLament@reddit

depends.. are you the kinda person who likes to be pals with someone only if it gets YOU something? This guys been more than generous with you. Yes I'd say you do owe him alot and it should be in the spirit of gratitude that you help him out. Why do you want to burn the bridge? he seems like a nice guy.

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bit_pusher@reddit

I trade tech support with my former CEO in exchange for beers. But we’re also good friends. If he’s a friend, help him on your schedule, hang out, have fun. If he isn’t, let him know you’re busy but you can recommend some professional services to him

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Mrfrunzi@reddit

Suck it up and do not burn such a wonderful bridge. That's just what I would do anyway.

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InteractionNo4855@reddit

Ill bet he knows other CEOs, people in your business, still has sway over current board members, id do his laundry if he asked, thats a valuable relationship where favors are stacking up in your account already. Step 1: Make it friendly, "ok its fixed, hey by the way Suzie from HR says hi and they are trying to implement this stupid policy i dont like... We sure miss you Bob!" Step 2: Profit.

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Ikarus3426@reddit

I've seen wealthy executives give huge gifts to lower earning employees like it was nothing. Just stick through it and treat it as a favor to a friend. You never know if he'll chuck a Ferrari your way or something.

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ZebraImaginary9412@reddit

Is OP helping him on company time? Or is the CEO calling him at home? If he's calling him at the office then just pretend it's part of the job. The current execs are not going to throw a hissy fit over minor, low-level tech support for the man whose name is engraved on their office building.

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Myca84@reddit

You never know how returning the kindness will benefit you in the long run. It also sounds like you might feel guilty if something serious happens and you have been ignoring him. It is up to you in the end.

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DjMD1017@reddit

Bite that bullet

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howmanyavengers@reddit

This is such a "i'm not a people person" IT guy post. Just help the guy out. You gave multiple reasons why you should, yet you somehow feel like he's overstepping boundaries.

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RazzlleDazzlle@reddit

Why not invite him over for a drink some time? Maybe retirement isn’t as thrilling as he thought it would be, and there is clearly mutual value and respect between the two of you.

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SuddenPitch8378@reddit

He sounds like he has treated you fairly and is not so much expecting a freebie as genuinely just needing some help. I like the other suggestions of perhaps picking up lunch for you etc. The world is built on relationships no matter how good an engineer you will always get further if you build good relationships with the people you work with.

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Prestigious-Second28@reddit

Reduce to not 100% coverage. „Sorry, I’m out for a dinner with my wife and I have a few things planned for tomorrow, I could help on Thursday“ etc Is it during work hours? If not, start picking up from places and things you’re busy at and reduce the time you actually help to like 80%, then a bit more after a month or two etc slowly reaching reasonable „sometimes“ or „rarely“

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chengstark@reddit

I would gladly help out a friend

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ReallyEvilRob@reddit

If you really don't like being a helpful friend to the person who helped you with your career, then just tell him you think he'd be better helped by an Apple Store Genius.

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Grouchy_Boot_6819@reddit

help him. you do not know how lucky you are.

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pixeltraitor@reddit

A former VP and I have stayed in touch after we parted ways at a previous company. He's a serial entrepreneur and always launching new projects. He helped me get on my feet early on when I was going through some major life changes and consistently feeds me side projects. Often it's for little pay or we just grab lunch and chat but every so often it'll turn into an ongoing paid contract for a year or two even after he departs the company. We help one another out, I get to see how he navigates various business situations and sometimes when things take off, he always makes sure I'm taken care of. Personally, I'd say hook the dude up. Foster the relationship and perhaps ask if he could be a mentor if you're looking into exploring leadership in the future.

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Mikeyc245@reddit

It's a use your best judgement situation. I've had bosses like you describe who have changed my whole life and done a lot for my family. It's rare, but they do exist. Don't be taken advantage of, but also return the kindness. Maybe try setting some parameters and ground rules? Let him know that of course your work at the company takes priority but you do want to help him when you can. This way, you're not rejecting helping him while also giving yourself more slack to schedule on your terms.

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NotMyMainAccountAtAl@reddit

I think that the folks saying to be a friend are correct, but I also want to caveat— friends have boundaries and can say, “I’m not free right now,” and you should be in a position to say as much. Old boss calls you Christmas Day to help with the iPhone? “Sorry, I’m busy with my family. I’ll make some time to help you in a few days, though. For now, here’s the troubleshooting page on their website— I’ll do what I can on the 1st if that doesn’t work.” It’s reasonable to set boundaries like that, and assuming he’s actually your friend, he ought to understand when stuff like that comes up. I saw something a while back that was extremely applicable to me and my relationships. It was about the two sorts of ways we ask for favors. One camp only asks for a favor if they feel that it’s a complete gimme favor to ask— IE “hey, we’re both walking up the stairs, and I have a heavy trunk that is a bitch for one person, but easy for 2 to lift. You have free hands. Could you help me get it up this flight of stairs?” Most reasonable people would say yes or feel like they need an excuse to say “no” to that (“I have bad knees and can’t take stairs very well, much less with extra weight, I’m sorry!”) The other group just asks for a favor, knows that they might hear a “no,” and takes it as it is. IE “hey, I have that same trunk, but this time your hands are full. Any chance you can try to balance your stuff on top of the trunk, and we’ll carry it up together?” If they say no, it’s no biggie to the second group. It sounds like you might identify more with the first group and your boss might identify more with the second. He’s used to asking for things from people, he’s used to being asked for things from people, and he knows that “no”’is occasionally a very valid answer. You sound like you’re more afraid that it’s rude to ever say no, especially if you don’t feel that there’s a valid reason to say no. Obviously, there are limits to both philosophies. If an asker says, “hey, could you gimme both of your kidneys to sell on the black market? Rent’s due, and I don’t wanna get a job,” that’s being rude. Similarly, if someone in the former group asks a favor and gets upset at being told “no” because they thought it was a social contract, they’re in the wrong and being rude. As with all things, there’s a balance to maintain, and it’s different enough for every group of humans that we can’t really come up with hard and firm rules that are applicable in all scenarios. The point of all of this rambling: it is reasonable, and probably expected, that you will sometimes say, “I’m sorry, I’ve got other stuff I need to prioritize right now. Can this wait until later?” (Or maybe you even tell a white lie— you’re in the middle of a favorite tv show and you can say that you’ve got something else to wrap up right now that needs your attention, so you’ll get back to him tomorrow)

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fu_orion@reddit

Always good to keep people like that on your side. Be friendly, start to build up a friendship with him. You never know who he’ll introduce you to in the future.

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Oceanman72@reddit

I mean, I would help him. He honestly probably considers you more of a friend at this point, and despite being retired, I assume he still has a lot of connections and can still help you career wise

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Monso@reddit

If he's still showing up to company events, it sounds kike he's still politically involved. From what I read, he's always had your back, no questions asked. Maybe you should have his, no questions asked. Given, in all honesty, "no" is an acceptable answer _if you have a reason_. He's not a client, so I wouldn't exactly interrupt my family events to run out and troubleshoot his wifi, but it sounds like you had a great professional relationship and I would hesitate to look a gift horse in the mouth. If we swap positions here, how would you feel if he dropped you like a sack of shit the moment you stopped being directly beneficial? That's kinda sorta what you're questioning here. Considering he's not 100% uninvolved, there may be a point in time where the board/execs look to him to ask "hey, ex-CEO, what do you think about OP?"...needless to say it would be great for his experience with you to be "above and beyond, immaculate professional".

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pedrolane@reddit

Yes but set some boundaries.

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Jarlic_Perimeter@reddit

Yeah, I have absolutely seen these situations pushed too far before, once turned out a retired VIP was trying to get free tech support for their start up lol.

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SmellyFbuttface@reddit

Accept that you’ll have to answer a question for him now and again. You might need his help with something down the road. Best not to burn that bridge

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Galenbo@reddit

Limit the exposure. Ask to call you back wednesday 10h30 AM. Every time. Although he helped and supported you, it wasn't always on-call and immediately following your agenda.

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Margrave16@reddit

This might be one of the rare cases where a retired CEO has earned a little help. You could set a half boundary like “I can’t always drop what I’m doing and help.” Like set his expectations that you might say no sometimes, but if you have nothing else going on you’re willing to help.

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Eridani105@reddit

Dude it just sounds like he wants to be friends 😭 considering all he’s done for you and he seems like a genuinely nice person why not be friends?

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duelinghanjos@reddit

I would help him, but don't feel compelled to drop everything and respond immediately

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matsu727@reddit

He’s a good contact to have. Who knows you might actually become friends!

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Chuck006@reddit

If it ever becomes a burden, you could politely say so and ask he compensate you for your time. However, I'd bite the bullet and invest in the relationship in case you need to ask for a favor one day.

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FluxMool@reddit

Does he compensate you well for the side gigs?

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Medium-Ad5605@reddit

You can't put a value on having a connection at that level, you never know when you might need a favour or an introduction down the road.

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trixel121@reddit

hes bored and looking to stay in contact. im sure he could figure it out. the guy probably lived his job.

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Kiernian@reddit

>He's always been extremely appreciative of my work which I value more than almost anything else because it hasn't always been the case in my career. The business he built helped put a new truck in my driveway and food on my family's table for 5 years. We can call this ^ the bare minimum that any CEO ought to be doing for their employees in an ideal world, but this? >He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. Almost nobody does that. Once would be exceedingly rare, once-in-a-career levels of goodwill from an employer. More than once? That's a fucking unicorn. Remember, a not insignificant number of places will ***find*** cause out of nowhere to FIRE YOU when you have the audacity to ask for a raise, under the assumption you're already looking elsewhere anyway. This guy didn't even make a show of "that's a big deal, I'll have to crunch some numbers" or whatever, he just. said. yes. on the spot, right then and there. While it's my personal opinion that what he did should be the normal way of doing things, it very much IS NOT and as a result should be treated as such. This is probably going to be a very unpopular opinion on this sub, but in my personal opinion, you should not only be grateful you had him in charge of those kinds of decisions for as long as you did and remind yourself of that constantly whenever he asks for anything, YOUR automatic answer to HIS plea for assistance should be the same his was when you needed him. If it helps, start going back over what your budgets would have been like WITHOUT those raises and crunch THOSE numbers to remind yourself of how things COULD have gone if he'd been thinking the way you are right now.

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itguy3001@reddit

I’ve been in your shoes. The president (and grandfather to the CEO I now work with) had to “retire” due to medical issues. I helped him with his tech and was even one of two people outside the family that was trusted to drive him to his medical appointments. When he passed, I took it pretty hard but the family has treated me very well and I’ve been with the company now for over 20yrs and I am now in the C-suite.

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Abystract-ism@reddit

Set boundaries when you need to-when his help interferes with your family/home life/work. If you want to cross the line between “boss/worker”, have dinner with your family/spouses. Becoming friends shifts the balance between you.

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ActionJasckon@reddit

I mean, as much as he's done for you transactionally, it seems as you look at his deeds as truly helping you those five years. Now he's asking you for help, I would self reflect and decide, is it transactional, or is it really helping the guy in your eyes.

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AzureGear@reddit

Even if not out of the goodness of your heart, this is the kind of networking that could set you down. Now, if you're getting five figure bonuses then clearly money isn't an issue for you. But he's probably got the kind of connections you and your kids could build generational wealth off of, at the very least.

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SnooCats5309@reddit

LET ME TELL YOU IN BOLD & CAPITAL " NEVER EVER BURN BRIDGES IN CORPORATE "

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Dctor_durden@reddit

Sounds like a great person to keep in touch with and to do small favors for. He sounds motivated , generous and kind., respects you and your work. Plus the benefit of him still in touch with your other bosses. You will allways be mentioned in a positive manner. And your career will benefit / keep benefiting from this relationship. Maybe he’s adjusting to retirement and you are a support right now. Can’t really lose on this one Reassess later.

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supaaface@reddit

I had a CEO ask if I could take a look at his wife's laptop. When he brought it to me it looked like it had been run over by a car. But hey, it's our standard corporate model (hmm, how did that happen?) so I swapped the hard drive into a new model and gave it back. I never heard another word. In your case I'd keep it up. Most of the jobs I've had later in my career were a result of networking and good relationships.

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fresh-dork@reddit

boundaries are fine - if it's once a week and he isn't demanding immediate results, that sounds like a reasonable arrangement, and you do feel some level of obligation. really, this isn't that bad of a thing

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NoobAck@reddit

Sounds like a person you really want to be able to call for a few favors..

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Opening-Emphasis8400@reddit

This seems like a comically small ask in exchange for what you have received. TBH, this seems like a complete no-brainer to me.

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BeatMastaD@reddit

He will settle into his new routines and wont be doing new things so often anymore, I would bet at that point the calls will slow, there will be more time between issues, and eventually he will realize its been long enough that he shouldn't use the company IT as his personal helpdesk.

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kahless2k@reddit

Sounds like a good guy to be friendly with. Probably worth the odd call here and there. If he calls with a bigger ask, tell him "sure, no problem - you grab lunch" and keep that contact close and happy. People like that can open big doors for you career wise.

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big_bob_c@reddit

Well, if he has an ownership stake in the company, treat it as "other duties as assigned". If it requires more than a trivial amount of company resources or your time, clear it with your supervisor so he knows that you are providing this support.

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MattyJRobs@reddit

"Hey [ex-boss], I would love to help you with this but at the moment I'm working on [task]. Could I have [subordinate] give you a call?" I would also help him yourself when you're able. But he above all people should understand that certain work shouldn't be interrupted.

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Mainbutter@reddit

My FIL worked in a university lab for years and had a professor mentor him. Even when FIL was only "auditing" as a broke non-student, this professor kept FIL around, engaging and educating. FIL credits professor for a lot of what good things happened in his life. FIL grew up in the Midwest, sounds like he wasn't treated particularly well by his parents, and raised pretty wild. He was sent to the family farms in the summer, and when he needed transportation back to the suburbs for school starting, was told "you'll figure it out". From the 1960s to 2010s until mentor passed away, the two were close, having monthly lunches along with other former lab cohorts. I got to tag along to help professor with some desktop problems. There was my FIL in his 60s helping a former university professor/mentor in his 90s. Keeping that relationship was valuable to FIL. You are not FIL, your CEO is not professor, but you should evaluate what kind of relationship you want to have going forward. That'll require some introspection.

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StThragon@reddit

God, I'd be happy to help that sort of person as long as he'd let me.

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Expensive_Prompt_697@reddit

Respectfully, there’s no way this isn’t an engagement bait post. Of course you help the guy. If you have this type of mentality for someone who consistently went above and beyond for you, I wouldn’t want to see how you are with people who haven’t gone the extra mile for you. Sure, feel free to set boundaries, as you see fit, but questioning helping this guy in the first place is baffling to me.

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The_NorthernLight@reddit

Honestly, do what you can to get him setup and working, and eventually his requests will diminish. If it starts to affect your day job, let your boss know and frame it as you are unsure how long you should be helping him. Im assuming that he sold the company, so he made good money. He can afford to pay someone else for on-going support.

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coff33snob@reddit

You need to keep this connection alive (grab a beer etc, don’t just be relegated to tech support) simply to keep access to this guys network… he probably knows everybody and their mother. Also, ask for favors back. He would love to help you too.

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Charming_Oatmeal236@reddit

Keep in mind that retirement is a HUGE adjustment! He's only 2 months in! Being so involved in his company for most of his life, he probably has few - if any - hobbies. He literally doesn't know what to do with his time, he's possibly a bit lonely, most likely doesn't know how to slow down, adjust to the new life. Keeping in touch with you no doubt helps him a LOT - he feels connected, busy, like he's doing something. He really NEEDS you during this transition. Hopefully he'll connect with other retirees, friends, family - find a hobby, a purpose to life, a reason to get up. Maybe he'll volunteer somewhere, start traveling, etc. Giving him your time right now is an easy and valuable gift.

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deathybankai@reddit

Bite the bullet. But definitely set boundaries on availability. Keeps you in good graces but not overwhelmed.

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Icy_Ebb_6862@reddit

Burning that bridge isn't worth the loss of a friend. I would help him out as much as you can. It's hardly overly taxing.

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k-mcm@reddit

Work out a trade if he's a nice guy. Maybe he has tons of cash, or can buy you lunch, or give you some unused days at a timeshare resort. Maybe you can replace a retiring exec. Some CEOs are are psychopaths and I wouldn't keep ties with them. They only see people as tools so you'd always have to be extremely careful around them.

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Bwwoahhhhh@reddit

Just once in a while say you're unavailable to help right now. You're a friend, you're not on-call. He seems like a reasonable person who would take the hint.

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estoopidough@reddit

All that praise you mentioned sounds like you just have to deal with it and just help out. I’ve had similar situations and the good thing is that it’s usually simple stuff. Maybe start mentioning things you need or want to do and maybe you’ll get gift cards or gifts of appreciation. I used to help out an ex-nba player a couple times and the assistant didn’t really have me go over anymore and would text me once in a while with questions but at the end of the year she fedexed a nice gift card to the house.

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Fun-Wolf-2007@reddit

Use this opportunity to learn from him, build relationships, in today's working environment it is very important to build professional connections

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Afraid_Software_8794@reddit

You spent a whole paragraph describing how he's been a positive influence for your life and family. I think that while it may be a little annoying, it's worth it just to be helpful and take some time to pay back the kindness he's shown you. Not everyone is like him and don't think of it as transactional. Kindness begets kindness

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bluemiata1993@reddit

You help that guy out for as long as you are with the company, and then some.

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Live-Control2132@reddit

Have a conversation about appropriate boundaries and the difference between employer, employee and ex-employer and employee. If you want to help the guy, help him, but charge him. It doesn't have to be a lot. You do need to be compensated for your time, expertise and energy That way there's no resentments. It's not a friend helping a friend. It's a colleague doing a service for another colleague.

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PK84@reddit

No brainer, help the guy out every now and again. I'm sure he'll still throw shit your way.

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CanaryWundaboy@reddit

He’s not a “retired CEO”, he’s a connection. Connections are great for all kinds of things, expensive whiskeys, country club tee times, paid-for entertainment etc. Sounds like this guy had your back for years, the least you can do is help him out here and there and I guarantee you’ll get more out of it in future!

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tgambit@reddit

Yes, bite the bullet

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42degausser@reddit

I’d recommend setting aside some time once or twice a week and if he needs anything outside that time ask him to shoot a text or something else async “Hey bill I set aside some time for us don’t feel obligated but if you ever need anything I’m free between 9-10 on Tuesdays and Thursday’s anything else just send me a text and I’ll get back to you when I can, remember I still gotta work, hopefully I can retire soon too!”

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AwesomeButtStuff@reddit

I would say yes, but I’d also put up some guardrails. I’d recommend telling him you’re busy but schedule some time with him maybe two days out when you can help him for 30mins or so. Send him a calendar invite. Let him know you have a hard stop. Maybe also send him some documentation or YouTube videos that might help him in the meantime. He’s a former CEO and knows that time is precious. By scheduling him, it send the message that you’re busy and guarding your time. It sends the message that you’re making time to help him. You’re also planting seeds for him to help himself.

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rickrett@reddit

I agree with the others to help him out as much as you can. If it becomes too much though, how about stalling? Like, “I can help for sure, but I have a bunch of family obligations this week. You around next Sunday? Something like that.

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bmanxx13@reddit

I would personally keep in touch with him. I guarantee he still has quite a bit of influence with the execs that are still there.

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Shooter_McGavin_666@reddit

Sounds like he’s a good guy. I can’t imagine not helping someone who’s been that good to me.

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ineedanewhobbee@reddit

This is how you build a professional network. Think of it as an investment on your future.

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trying-to-contribute@reddit

I think your guy calls you because he trusts you to handle his IT affairs, just as other old people call their family members for IT stuff help: Much of this stuff is actually pretty sensitive, the old folks don't want to look helpless to strangers, and around close people, they can let themselves feel more vulnerable. I'd bite the bullet for awhile. Also, I'd talk to my boss. A lot of companies (at least use to anyways) keep a secretary/ea around to handle the retired CEOs correspondence. Sometimes this extends to other executive support. It pretty much depends on his retirement agreement. So, there is actually some small chance that your ex ceo is expecting this treatment to be part of the retirement package, as this was very very common 20 years ago, and you were never made aware of it. If it's not on the books now, it certainly has precedent to be. And it's not going to be an official deal, maybe you and your boss can work out something informal, especially since it's just an occasional thing. Then at least you can tend to it on the clock, or at least be allowed to leave early and tend to the task at hand on certain days.

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Interesting_Fix4519@reddit

You need to get out of this anti-work and anti-CEO mindset that it seems you've developed from spending too much time on Reddit lol. You have the CEO that we all want if he's been that kind to you. Annoying to see you take it for granted, to be honest.

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Temporalwar@reddit

Here is what I would say...I’m always happy to help with the quick stuff. But for these bigger ongoing issues, I feel like I'm doing you a disservice because I can't get to them fast enough with my current workload. If you want consistent support, I could come over on a scheduled Saturday once a month for a consulting fee, or I can help you find a dedicated managed service provider who offers 24/7 support.

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Mongolian_Hamster@reddit

It can be a two way street.

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BookoftheGrey@reddit

Xxx xxx b

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Tumbleweed_Waste@reddit

No! Always be there for him. He will see that and repay you when you need something. Just be a friend to him now, it's what he needs. Sorry.... But suck it up a bit!

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TangibleExpe@reddit

Any chance he’s bored and lonely?

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Funny_Requirement166@reddit

Yes Mr personal tech buddy for life. Hell he might open up new door for you again

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SnooBananas7504@reddit

Bite the bullet

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Slamshanks@reddit

I’ve been involved with several businesses where the CEO has retired and I’ve helped them once they leave. I’ve felt like they helped me by paying me and it’s paid off in the long run helping them. I’d call them friends now. I’ve even helped the wives after the CEO has passed. As I’ve mentioned it’s paid off in the long run.

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Necessary_Motor_6096@reddit

Sounds like you need to set up a consulting business and charge him by the hour for your help. Win-win.

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RumRunnersHideaway@reddit

It’s ok to burn bridges. The idea that you don’t want to burn bridges, comes from assholes that don’t want you to get away with bad behavior.

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waxwayne@reddit

You need to change the nature of the relationship from a business one to a friend one. I do stuff for my friends all the time. If he treats you badly or not like friend wean him off.

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Fun_Value_1581@reddit

You belong on WallStreetBets with how regarded you are; this is a blessing not a curse so realize how to benefit your friendship as well as your time.

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BunsMcNuggets@reddit

Ask him for compensation and try to be polite about it, he can afford it but I’m sure he’d understand your time is valuable.

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DoinIt4DaShorteez@reddit

Rich guy wants you to answer a couple of questions and you want to turn down that opportunity? Not smart. Get off reddit. Plus, fake story.

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VoltexRB@reddit

Him being gone doesn't mean he can't still pull strings on promotions

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MR_Moldie@reddit

Suggest a local company to him that you trust. Try to explain that because you are employed by the company he founded but no longer works for it puts you in an ethical bind. If he is the person you think he is he will understand but CYA. Document everything.

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angelacandystore@reddit

Options: Hey, here is my friend X they do consulting they can help you, I'm too busy with work, haha, sure you understand. Hey, work, retired CEO is calling me for tech support are you going to pay me to help him or should I direct him elsewhere? Hey retired CEO, my consulting for tech support costs X amount an hour, are you interested? Hey retired CEO, you can find all this info on YouTube, I know you're a savvy guy (say this even if he is not) so you would want to figure it out yourself with the proper resources.

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angelacandystore@reddit

Just ask him for money and he will pay you to do it!!!!

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Proper-Rain-6399@reddit

Are you sure he only wants tech advice and not just completely lost after retirement, im guessing going from CEO to retirement is a heavy change. Probably bored out of his mind needs someone to talk to, just so happens all his devices needs your help.

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SpiveyXIII@reddit

My Grandparents constantly ask me for technical help, at times I do feel like an on call tech person for them. I love them a lot and they are amazing people and have helped me out a great deal and are amazing with my four kids. When I feel like it's a bit much I remember that it's little effort on my end but a big deal for them and I'm always willing to make time to help when I'm available. Usually within a day or two. It sounds like this guy trusts you a great deal and probably also wants to keep a connection with you. There will be a time that you need to ask a favor and I would just remember that and keep in your back pocket.

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electriceel57@reddit

If he's a "good guy" which it sounds as if he is, then yes definately help him out....forever if you need to. He obviously respects your knowledge and like you say, he helped provide good employment for years. Don't be miserable, unless it's happening every damn week it's the least you can do

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baan1994@reddit

Most rage bait post I’ve ever seen. Gtfo

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desert_dweller5@reddit

I think healthy boundaries are good. You earned that paycheck and whatever else comes with that such as bonuses. I would not feel obligated to help him especially not for free. Did you charge the other people for the side work? This is the same thing. The company employs you not the retired ceo. That being said, It’s a good idea to keep yourself on his good side. You definitely need connections in high places. So I would say that I would have a conversation with him and say that you love helping him. It’s only fair that you get compensation for your time. Once maybe twice is a favor. More than that is getting taken advantage of. He understands business. Make it a business deal. The free tech support offer expired in Jan 1 of this year. We can renegotiate our agreement. Here are my terms. And just see what he says.

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drewpeacockIV@reddit

i personally would just call that homework if i made as good a living. seems worth it.

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Assumeweknow@reddit

Dont say no to him ever. Just make sure you schedule around your stuff for him. He will likely work with you on the scheduling. Also, at some point charging for stuff is okay or if you are smart and you have to spend 6 hours working on his stuff its okay to say you gotta invite me to your next bbq or this is worth insert favorite sports team tickets. Can we use your pool next weekend, etc... literally these are okay things to ask as your are transitioning into friends rather than boss suburdinate relationship. Trust me, powerful connected friends are worth thier weight in gold when you decide to expand life into things you just dont know.

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hmtk1976@reddit

You´d pick up that bar of soap, wouldn´t you?

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Assumeweknow@reddit

No, I'm just still earning money from my previous two company bosses. They kick stuff my way every now and again and I do small favors time to time. It just works out.

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shichiaikan@reddit

I was in a similar situation a few years back, and what I did was I let him know that I was really busy, so I needed to set up an appointment to help him out. It was about a week out, but I let him know of a business I trusted to do the work if he needed it right away. The second time he had to wait, he called the mobile tech I suggested.

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okan931@reddit

I would totally maintain the relationship man, like you said, the things he has done for you are immeasurable and he sounds like a cool dude to be friends with and a legendary contact for your network

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jasonsyko@reddit

Just help the guy. Could absolutely benefit you in the future and it’s just the right thing to do.

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randopop21@reddit

For all he's done for you, you aren't willing to once in a while spend a few minutes helping him out? If it were me, he would ***literally and absolutely get personal tech support for life***. And his wife too. Also, don't be short-sighted. His mere friendship could be of tremendous value to you in the future. He's a former ***CEO***. People like him know ***other*** CEOs and executives. If something goes wrong with your position or career, ***one word*** from him to another CEO/exec and you're back in the saddle again. Also, even though he's retired, many hard driving smart people \[like someone who's made it to CEO\], are restless types. More than likely, they are harboring ideas that they couldn't pursue in the old company. They have MONEY, which means they can launch another startup with just their own funds. ...and guess who they will call when they need someone to build out and run their IT infrastructure? ...and guess who could benefit by getting in on the ground floor of a company??? I'm talking ***life-changing*** benefits. I'm retired--early--because of people like him that I have maintained great relationships with. Let me put it this way: If I were you and I saw his number light up on my phone at a rocking New Year's Eve party, I would answer it without hesitation.

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PopularBid923@reddit

Might be a little annoying for sure but someone like this seems worth it. It’s probably not much work to help him with the little stuff compared to what you COULD lose by bringing it up with him.

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handsoffmyjetski@reddit

These are the type of people you are pleased to help. I don’t understand why you wouldn’t want to scratch his back, bros itchy and needs help. How does your back feel?

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Earth271072@reddit

My boss and I always say "it's nice to be nice to the nice", and it sounds like he's been very good to you

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New-Zookeepergame-0@reddit

Yes, definitely help him out. Not only for the opportunity he gave you but for future opportunities

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frogeyes111@reddit

Really dude. Is it that fucking Hard?

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tiny_chaotic_evil@reddit

*what bullet to bite?* *if you consider helping someone occasionally as 'shit', that's a you problem*

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onebit@reddit

He may bring you an opportunity.

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naughtydadinnorcal@reddit

You are a trusted person in his circle. I'd look at it as an honor.

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fixedwireless_ops@reddit

Absolutely! Best mentor you could have.

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Fit_Heat_3308@reddit

Well, in his mind, you're still his employee. Or maybe even a friend/kid he's helped. Do you want this guy in your life? As in, not just for his money/connections, but in general? If the answer is yes, next time he calls, fix the issue he's having and ask if there's anything else he needs help with. There probably is something and you can sort it all out in one go. Set up something extra for him too. Maybe an app on his ipad he would be interested in (financial, hobby-related, etc.). Then while finishing up, casually invite him for dinner or something social (a game, golf etc.). At some point, you can also ask if he'd be willing to share his thoughts/advice on xy (a small investment of yours, something business-related you want to learn more about, etc.). In other words, steer the relationship towards more of a friendship/mentorship (as opposed to tech support), let him feel useful in a knowledge-sharing way and accept that maybe now and then there will be a tech issue to solve.

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2cats2hats@reddit

If he is as generous as your post makes him out to be, he probably won't mind if you ask for compensation. It doesn't need to be a lot but he most likely understands your waking time is partially devoted to assisting him. Sounds like he retired comfortably. It doesn't need to be money either. Does he make homebrew beer, is his wife a chef-level pastry expert. Barter. :)

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Waahstrm@reddit

Small price for big connection if you ask me.

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mtdewabuser@reddit

I had a boss like this once. He took great care of all of his employees. A few years later the business sold, and we parted ways. Occasionally he would still ask me to help him with something at his home. While I was there one day, he asked how my wife was doing. Kinda sad lately I said, she didn't have the grades and didn't get accepted at this certain business school. I know someone down there he says, let me call him. Sure i say but not really expecting much. The next day she gets a call that she'd been accepted and welcome to the school. Never burn bridges.

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jimh12345@reddit

Just help the guy. Someday you'll look back and feel good.

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OptimistIndya@reddit

Take care, also increase your network.

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BrightDoughnut2866@reddit

Just because he's retired.doesnt mean he's out of the game entirely. It would be wise to keep him close, what goes around comes around.

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Iforgot_my_other_pw@reddit

This guy sounds great. I would keep helping him however I can.

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davan6475@reddit

In the long run, it might be beneficial to keep the relationship - unless the work he is asking you to do is too much. Having a wealthy and powerful dependent on you is not a bad idea as long as you or him don’t abuse the relationship. Over time, connect him to services he can lean on and take time to respond to his request and that is a subtle message. If you do it well, you can still keep a professional relationship that might help you in future with another job, recommendation or just become a mentor.

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Southern-Ad4068@reddit

Glad we all have the same consensus. Plus, if he just left his position, he probably got some tee times to invite you to too 😂

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coukou76@reddit

Usually I would say your boss to gtfo but he genuinely seems like a great guy. Maybe you can have a talk to slow things down a bit, it's still a job but be careful not to close any doors, these guys have a tremendous local network usually

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UrethaneMotiv@reddit

Embrace being his personal tech support guy for life. Even if he's retired if his name is on the building he still has pull. As long he's the sort of person who also accepts and understands if you say you're too tied up with company work to help him out sometimes. I'd look at it this way. if you worked for Microsoft and Satya Nadella retired and was calling you for favors, you don't owe him anything. I bet most people don't even know he's the current CEO of Microsoft without googling it, and once he leaves he's going to have no associate or pull inside the company anymore so who cares. But if Bill Gates is calling you for help, you better believe you're going to jump at that opportunity. Even if he's stepped away from business operations you know he still has a lot of backroom control over what goes on. And you never know when he's going to make a recommendation that lands you your next promotion, whether it's inside your current company or he happens to be talking to his golf buddies and mentions you to a CEO of an even larger company.

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ilrosewood@reddit

Yes. You hook him up. It’s what a good person would do.

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KingKong-BingBong@reddit

It sounds like most definitely keep helping him. I mean are you grateful for what all he did for you? Don’t be an ingrate. Plus I’m sure he still has some pull and if you need a favor in the future he’s probably someone to have on your side

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ArmFallOffBoy@reddit

Tell him to bring his stuff into work. You get paid to do it, noone is gonna dare to complain.

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dsxy@reddit

Help the guy, he's a rare manager.

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Important-Tooth-2501@reddit

You just listed all the reasons why you should ”bite the bullet” (even though I wouldn’t use that expression in this case). If I were you, I’d see him as a friend/bro/family member who needs help. One hand washes the other. Let’s be honest, you can barely compare occasional that-one-family-member level IT help to the value of the things he’s made possible for you in your own words. Respect for respect, honor for honor etc etc.

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joseb55@reddit

Consider it a badge of honor. It’s a rarity that he still confides in you.

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NewspaperSoft8317@reddit

> The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures). I'm antisocial but if that's true, my wife would've twisted my finger to help him out.

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CompetitionOk1582@reddit

I'd help him.

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WorkingInAColdMind@reddit

Assuming the best, he co sides you have a friend/family relationship and is asking for help. There are limits, but I’d say help him out as best you can and respond accordingly if he asks too much. “Wow, that’s a lot more than we can do in just a call, you might be better off with Apple genius support so I don’t make it a bigger problem”.

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Switchcitement@reddit

This guy sounds like a good person and saw your value you both as an employee and as a person. Also, this level of transition is hard for many. Looks like he sees your a dependable and easy to work with, so he's leaning on you for when this transition period is going on. Help him out bro.

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-TheDoctor@reddit

\> He's always been extremely appreciative of my work which I value more than almost anything else because it hasn't always been the case in my career. The business he built helped put a new truck in my driveway and food on my family's table for 5 years. He's approved multiple large raises and said "absolutely" without hesitation when I asked for a promotion. He's signed his name to hefty bonus checks every Christmas (some 5 figures). Hey, so, unrelated question but are y'all hiring?

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EveningOrder9415@reddit

Help your friend

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Far-Nefariousness588@reddit

TBH I wold say this is not an uncommon situation. Ive had people like this over my career and in my opinion, it always benefited me to maintain these relationships.

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bombasterrific@reddit

He knows you. You're familiar to him and he trusts you. He doesn't want to call other people because of that. Just take the time to be courteous to him and use the opportunity to pick his brain get advice, being in his good graces is a benefit for you. Most people would be frothing at the mouth for the opportunity to have someone like that in their corner. Plus, having someone with that kind of pull and connections owe you some favors is definitely a good thing. .

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bErSICaT@reddit

I would be kind to this person and continue to help. They sound like they have your best interests at heart and will probably help you network.

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mwax321@reddit

Invite him out to a thank you lunch/dinner. Say something like it's a catch up and a thank you. And you can talk about work and hobbies. The goal is: either you freak him out and he doesn't want to be your friend, so he decides to never talk to you again. Or you keep talking and become more friends than boss/worker.

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Professional_Law_942@reddit

I wouldn't say no, but if you're an incredibly busy person and you have subordinates that might be better suited to that sort of thing (or more time), I'd take each call, see if you can troubleshoot it quickly and if not, let him know you have xyz meeting/project that's taking you away and your assistant/teammate can assist this time. Make that person responsible for really silly questions, but keep in mind sometimes recently retirees don't know how to disengage and then feel a sort of loss or lonely when the music stops playing. Be mindful it might be a way of reaching out bc they miss being relevant. I'd make every attempt to be cordial and helpful to this mentor of sorts. You want this emeritus colleague in your corner - I've been in this position before and it is so helpful having the "pull" of the big guy in the background. You never know when it may come in handy!

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Final_Tune3512@reddit

I wouldn't burn that bridge. Sounds like he genually likes you and depends on you. It's a good spot to be in versus the other way around. Plus you can also say, sorry I was helping out so and so as an excuse to delay getting back to someone lol.

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AggressiveCoffee990@reddit

Man just return the favor. It sounds like a really good connection to have and maybe he thinks you're a cool guy who doesn't mind helping out. Maybe invite him for lunch some time he might pay for it lol.

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Infinite-Bother-3168@reddit

Bite the bullet. Obviously he trusts your opinion with his personal affairs, that means a lot.

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FlatwormNo3937@reddit

Sounds like he may be trying to also stay in touch. Have a beer with him. Build a relationship. You already know it’s about who you know.

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datOEsigmagrindlife@reddit

Usually I'd say "tell them to kick rocks". But because he's treated you well, and is probably a good contact to have. Spending a few hours per month on tech support could be a good payoff in the future. Maybe nothing ever comes of it, but it's still worth nurturing.

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Pristine-Copy9467@reddit

Yep. Simply reply “this is gonna cost you lunch, sir! :)”

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Free_Alternative6365@reddit

You are not biting a bullet; you are helping someone who has helped you. Plus him being retired is not the same as him no longer having power or influence. You might *also* want to be good to this guy bc now he doesn't have anything but time, money and career's worth of c-suite level contacts and wisdom.

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Ok_Connection_5348@reddit

Worth it.

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Hypothetical_BSN@reddit

I’d help this guy for life.

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Friction500@reddit

Why are we so against just helping one another 😞 I offer so much free tech support to my loved ones and partner’s parents. It’s what I offer my community. Late stage capitalism has us confused.

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iiiiiiiiiijjjjjj@reddit

Just tell the guy when you get time

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Dry_Yam_4597@reddit

And thats why you dont help those below unless they really are worth it. They wont reciprocate. There is a reason why the upper class keeps lower classes at bay - people like op.

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pineappleshoos@reddit

Its always good to be needed, keep him onside and help him out once and a while. Seems like you owe him alot.

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clayterris@reddit

Ask him for some favors! (seriously)

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SoFloFella50@reddit

Bro. Help the guy out. Ask him for advice on your investments. Ask him if he’s interested in playing a round of golf. That’s not your boss anymore, that’s your buddy.

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AtlantaGangBangGuys@reddit

If you don’t you will definitely be remembered for the wrong thing. Keep a friendship with this guy and it’ll comeback tenfold. And yea burning bridges with everyone he knows too.

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Blueporch@reddit

Maybe you could line him up with someone reputable he could pay for personal tech support.

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1to14to4@reddit

The boundaries you need to set is that when you are able to help him is on your schedule and not his. Other than that seems like you could help. The volume is what matters here. In the beginning, he might need more help getting set up and that's fine. But if it turns into a continual thing that is non-stop then you should consider pushing him to find other help, especially if he is wealthy.

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jadedarchitect@reddit

Protecc your former boss - though he may be unwise in the ways of technology, he is wise in the ways of being kind.

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Psychopomp84@reddit

Not only should you help the guy out, but you should invest some extra time with him. If he’s reaching out like this then maybe he’s looking for a friend after losing one of the most significant forums he had to interact with people.

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Artistic_Irix@reddit

Help him. Done. How hard is it for you? With everything you've listed, is it worth risking something for lazyness or any other silly reason? This is a connection you want to keep, for a long time. He may be your next employer, or recommend you to one.

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Newtiresaretheworst@reddit

6 figure bonus cheque. Yeah answer the phone two times a year…..

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Shedding@reddit

These are the people you help. Period. Don't think for a second that because he retired he doesn't have clout. He will so help you rise, and even if he doesn't, he did provide for you. You pay that back.

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pokpokza@reddit

You will have to hin at him that sometime you might be too busy to help him because of personal reason and also try to be his friends and hope he understand that.

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GregaciousTien@reddit

That type of employer is so incredibly rare. If you don’t want to help him anymore, I will. That type of leadership needs to be recognized and rewarded

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lpbale0@reddit

You might not want to help him in the moment, but you will likely never regret having helped him later if you do assist. If he has scant other people he is close to, or very little other family then it's possible he considers you fam. There's nothing wrong with helping him out in the long run.

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theoreoman@reddit

You stay friends with a person like this because they're going to have many industry connections and will help you out

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GroundedInformation@reddit

Become autonomous and send him an invoice for your time

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hotfistdotcom@reddit

How significant was the pay gap between you and him? Does he pay you hourly for this? Or you are just expected to help an ex exec, for free, forever? This seems exploitative even if he was "generous" and generous is still relative, especially for a founder who I imagine you can easily figure out real roughly how much he was paying himself just based on assets you can see in his life. If it offers you no benefit and the only risk is consequence, that's super toxic.

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vectorczar@reddit

By your own account, his unwavering support of you, your work, and raises was resolute. Return that kindness.

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OptionDegenerate17@reddit

Just don’t pick up. Easy to miss a call

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atticusw@reddit

100% help him out. He supported you at his company for half a decade, and is a good person to have in your close circle. May have to manage expectations — like, maybe some things should be scheduled vs real time if interfering with your personal schedule. But sounds like your both worth each others time.

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Bombadier83@reddit

To everyone saying “oh, he sounds like he’s been so nice, so be nice to him”. The ex-CEO might be nice, but he never gave this guy pay without expecting work in return. The pay and promotions weren’t favors- they were transactional, the cost of keeping what was obviously a good employee. As far as advice, I’d just charge that time. When you are asked about, explain the situation and let the higher ups in the company decide if they need to cut off the supply of labor to the ex-CEO or if his name being on the building means they will bite the bullet. They are the people who should be in an awkward spot between a friend and work, not you.

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Spiffy_Legos@reddit

This is why you have no friends.

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Internal_Peace_7986@reddit

Sounds like a really great and personable person, also lucky for you he's found a friend in retirement. Don't blow the friendship just because he asks for some help every now and then.

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phobug@reddit

Sounds like a nice guy and it seems you want to help him to but you’re afraid that in time you might be exploited which is pretty much the rule with personal IT requests. In your place I would do it but make sure to raise the point that you’re happy to help a friend but this is mostly a one time thing. From there on give him some actions he can take in order to be more independent with the tech or if he insists on professional help you can give him a rate.

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FizzyBeverage@reddit

He’ll settle down once he’s in retired life. Make sure you get rid of his Windows PC and get him on a Mac. They’re appliances and need a lot less support.

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Tzctredd@reddit

I don't understand why are you even asking this.

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Groundbreaking_Ear27@reddit

I’d say help him, even if it’s a bit of a reach. From a professional standpoint, even if he’s retired these are the types of relationships you want to foster. When I first started out I thought it was all about do the best work and you’ll excel, but I didn’t realize until my early 30’s just how much if not more so it’s the relationships you have and people you know. So even if it’s from a self serving standpoint, I’d help him out — at least when you can and it’s not some gratuitously time consuming undertaking. And I say this as someone who’s very much learned to put work in the rearview once 5pm hits. On a more human level, he sounds like a stand up guy and for all accounts has been there for you when he ran the company. People in a position of power who are that good to their employees are ~not~ a dime a dozen, so beyond it making good sense to be good to your employees it also sounds like he has been a friend to you in what capacity he could while being the founder of where you work. It’s up to you obviously if you feel like reciprocating, but based on how you described him if I were in your shoes I would want to help a guy like him out when he needs it. There’s also a 3rd element to this — when people retire they’re often a bit lost. It may be hard to imagine your companies founder as “that” guy but he may well just not be sure what to do with himself yet, and his way of staying connected to the business or even just looking to talk to a friend back from his days in the office might just be you. Maybe invite him out to dinner or drinks one night and see how it goes? I think you may be pleasantly surprised, be able to foster a friendship with him outside of work/helping him, and the calls to you for “help” might turn into less burdensome time spent talking on the phone with a friend. Just a thought!

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Cr1ck3ty@reddit

You sound grateful. Now its time to reciprocate

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bloodmoonslo@reddit

I would continue helping to do the guy a solid as he had done for me in the past, but would not hesitate to draw a line if it got out of control

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SlickFrog@reddit

Maybe when he calls tell him that you have to get something completed right now, but you’ll get back to him after 5:00, hopefully he’ll get the hint that you are helping him on your personal time, and he’ll limit his asks

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ButterscotchSea2781@reddit

A guy like that will still have pull. Also, regardless of that, if he helped you out as much as you say he has don't be a dick.

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RubberDuckyFarmer@reddit

So.. you work in IT.. And someone who has the ability to be a CEO wants to confide in you on a personal level. And you find this to be a personal annoyance. You belong in IT.

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adhd6345@reddit

Personally, I’d say bite the bullet but suggest using the Apple Genius Bar or similar if he has access to it.

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DependentArm3391@reddit

You need to do what this guy says

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ouatedephoque@reddit

Dunno, this seems like a no brainer to me. Help him.

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Alternative-Arm-3253@reddit

He sounds like a friend.. to me.. who's going to be needing some free flyer miles. Shake hands and give the dude a huge hug. He sounds like someone I'd love to have in my life.

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c6munoz@reddit

Bite the bullet

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StepChair@reddit

Sounds like a good connection to have and even a better grind

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SubtleUsername@reddit

You would be severely damaging your career to burn this bridge.

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awwuglyduckling@reddit

My experience with guys like this (nice & successful) is that it will pay off to maintain a good relationship with him. If he’s not calling you Friday night to fix Netflix, help him out

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Accurate_Stuff9937@reddit

Wow. Men are so incredibly selfish. It's just never enough for you. Take take take and never give. Id put money on you never satisfying your wife who gave you 3 kids and did all the parenting either.

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smith2na@reddit

Send him my way. I like helping people.

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OilMeUpStewart@reddit

If you feel like you’re being taken advantage of. Sure ease off the help. But if this person has helped you out and considers you a friend of sorts I would just help him out.

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AlissonHarlan@reddit

Why if he's just trying to have excuses to hang out because he like you as a friend? Maybe propose him a coffee or something once and a while

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MayorPirkIe@reddit

These comments are depressing. Everything he's "done for you" has been in the context of your job. Did you deserve those raises and the promotion? Yeah? Then he didn't do shit for you. You earned those. Everyone in the comments telling you to just help for free because he "helped" you is making me sick. It's actually pretty shitty of him to now expect you to still work for him for free. It puts you in a shitty spot, which is why you made the post in the first place. Next time he asks, say sure you'll help but he needs to take you out for a nice steak dinner. Phrase it playfully, but it will get the message across that you aren't his free IT service without just asking him to pay you outright or refusing.

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tttttesting@reddit

Sounds like you are morally obligated to help him occasionally. But you can and should tell him when he should seek help elsewhere.

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Marvel--Jesus@reddit

I'd help him out all the time, if he's as appreciative of you as you make out, I'm sure only something good will come of it.

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Calm-Bed4493@reddit

Have this a lot. I just take care of them, when work is 80+ hours a week I'll send them a guide and let them know when my availability is expected to free up if I'm too busy that way they know I'm prioritizing the business, and not saying no right now. Which they generally will take as a good thing

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LaureGilou@reddit

He calls you instead of someone else (even though he has money and could probably pay for a pro) because he likes you. That and the fact that you're grateful to him and he has always been good to you...help him out. It probanly won't be once a week for ever. He's just getting settled in his retirement life and will probably need you less over time

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coldfusion718@reddit

If you don’t want to have a powerful ally, then by all means, tell him to fuck off in the most business speak way possible. Something to the effect of “Hello Mr. Founder, I regret to inform you that since you have officially retired and are no longer an employee of the company, I’m unable to provide technical assistance to you for what amounts to personal devices. I cannot use company resources (my time) to assist former employees. I appreciate your understanding.” I’m just curious, how the fuck did you get to where you are with not being able to read the room?

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Maleficent_Leave4314@reddit

Sounds like he took great care of you as a boss. If you're available answer his calls and help him if you can. If you arent interested or can't that say just don't answer. That way it doesn't need to be some awkward interaction of why you can't help that say. Unless you really don't want to then just cut it off, but imo if he took that good care of you and was such a good boss, what does it hurt to help him with something minor here and there?

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kozak_@reddit

You have personal access to a well connected former CEO and you want to break off that access?

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murgalurgalurggg@reddit

I’d just make the responses a little slower and after hours type of thing. Not burn the bridge but I think he will realize he’s burdening your work hours.

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xkblo@reddit

From what you described, you did a job and he paid you to do the job. Can't understand what is the trouble

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JamponyForever@reddit

You should outright say “if you were any other CEO, I’d would be inclined to draw a line and tell you to find someone else to help you, BUT you have been an amazing and generous mentor to me, so I am happy to help you whenever I can.” Or something along those lines. This shows that a boundary is there, and he’s getting special treatment because he was good to you. You keep yourself respectable and you help the dude. He knows your thought process and motivations and he’ll appreciate the help even more.

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pointlessconjecture@reddit

Take it from someone who was in a similar position. He trusts you, and your future is absolutely assured. He may even be reaching out, not really for help, but just to stay in touch without seeming like….lonely. Time to see past the work relationship and to a genuine friendship, with someone in a position to always look out for you and help you stay on your feet. You don’t burn those bridges, my friend.

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KJC055@reddit

Why would you not want to?

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roxamine356@reddit

Probably just wants to spend time with you as a friend, and not as your boss, but don’t know how to, or too shy to communicate. Hence the “tasks.”

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Clubsandiches@reddit

Do it OP. They are probably all quick fixes and having professional connections to the extent you do is valuable. CEOs know one another and he'd probably be able to get you in somewhere for work or at least recommend you. Especially with all the stuff you mentioned he's already done for you, not that you owe him in perpetuity but definitely good to keep him in your Rolodex.

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payperkut187@reddit

Help him out, the way you have spoke about him, you owe him. Also this could be the type of person that values your knowledge and slips you some cash on the side… if you accept the money that’s up to you.

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PleasantAmphibian404@reddit

I had one of these. Family friend, retired, with a great deal of community influence and plenty of money. He and his wife needed various small things over the years. I always made time to accommodate, even when it was a pain in the ass, because our family had a lot of respect for them. Then one day I found myself blindsided by a potentially life altering (not in a good way) circumstance, that I could not see a way through. I was devastated, and felt sure that everything I had worked for was in danger of slipping away, and there was literally nothing I could do. Here comes family friend. He had the connections, with both people and organizations, that were well positioned to help me. With just a few phone calls, all the support I needed materialized. People I didn’t know were contacting me with solutions and connections, all referencing family friend. My “unresolvable” problem literally disappeared within a week. Help the man out with his iPad. Someday he may repay you with his influence, if nothing else. If not, *you* are the hero in the story, by helping someone who needs it. Either way, you win.

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synti-synti@reddit

Ultimately it's just up to you but if I were in your shoes I'd pay him back for the care and help he gave you.

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IJustCantGetEnough@reddit

Come on now. He’s been good to you. You be good to him.

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carpe_fatum@reddit

Continue to be good to him; make sure he's still good to you. You want a raise or you want a promotion? You have an earpiece... Life is give and take, and it boils down to the people you know and associate with versus what you actually know. You have a very good contact.

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Wwwweeeeeeee@reddit

It costs you nothing to be kind and respectful and helpful to a person who's been kind and generous. You have no idea how rare that is. Treasure this relationship.

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f0gax@reddit

I think it’s okay to help them. Also, set expectations. Like that if something for the business comes up, you have to drop and deal with that. If it’s a serious issue for you I would go to your boss and ask them.

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Speak4yurself@reddit

Guy helps you to succeed, pays you well, treats you well. Just wants some help occasionally and asks for it from someone he knows. And you want to know how to politely tell him to fuck off? Sounds as though you just don't like him. Just stop taking his calls and he should get the message.

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Alternative-Wear-365@reddit

How do people like this make it this far

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No_Reference_9640@reddit

Sounds like he is still your boss… He founded the company so likely still owns some portion of it, maybe a board seat etc Anyway I would just keep him happy for now until you work out how much sway he really has now he’s retired and how much work it will be for you long term

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Significant_Oil_8@reddit

YTA for even asking that question. He helped you in a life changing ways and you're too lazy to help hin with his iPad? I really do not understand how someone can be THIS selfish.

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EcstaticYou1322@reddit

What’s it hurting to help him? A friend with connections isn’t a bad gig.

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longlurcker@reddit

I always mention to my small clients, I can help but it may take me a week or so if that’s okay. I can usually get them into buying thier shit from geek squad going forward.

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Connection-Terrible@reddit

Is there a board? Does he still serve on the board? Is he still a majority shareholder?

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Admins_suck_ballss@reddit

Seems like it would be in your best interest to continue this friendship, right?

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CommitteeEmergency82@reddit

Send him an invoice.

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ireidy006@reddit

Help out for the next 12 months, see if he sends you an Amazon voucher in that time. Always make sure it’s in your time slot, If he asks say yes can do it but it will be xyz date when your free.

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VBBMOm@reddit

Def keep him in your corner. Loyalty is something that is hard to come by. Don’t treat him as a chore. Life is t always about what you get but why you give.

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Tex-Rob@reddit

People are giving fine advice as far as just maintaining that business relationship, but I think a more important question is, "Is he still on the board?" I could see a company being down with continuing to support a board member that was the former CEO.

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MixFine6584@reddit

One of my biggest mistakes in my life was not taking this super low paid job by this super wealthy dude when i was in varsity. The experince I would have gained would have made me far richer than i am now

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Jihambi@reddit

The next time he asks you over, tell him you will bring a six pack of beers to share, a deck of cards, a chessboard; something you think he would like to do socially and see if he will hang out after the job for a bit. That will tell you if there’s any social/friendship aspect.

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Worthlessstupid@reddit

Man I feel like I’d answer this guy’s calls until he draws his last breathe, especially for tech support. Without knowing his nature it’s hard to say. I imagine a man got described can be a bit of a force to be reckoned with? He sounds like a man who values relationships, so perhaps he’d respond well to a respectful, “can I call you back, I’m working on a pressing matter for the business.” Invoking the well-being of his life’s work, and not in just as a tactic but it is true, might trigger him to look at the calls from a time management perspective. Hope it all works out friend. Best of luck.

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livelifefullynow@reddit

Bro honestly you suck for even asking this question. Do right by him, as he is done right by you. If you have been watching the news lately, most CEOs don’t give a shit about their employees.

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OnePinginRamius@reddit

I've got a crazy idea to throw at you about him. Instead of being a little bit annoyed by him constantly asking you for these things how about you go full speed into being one of his closest friends? even if it's just to perpetuate your career. The contacts this guy has and probably the knowledge that he has from running this business for so long will benefit you so much just by you showing him that you weren't just his employee but you actually dig what this person is all about. I'm sure one random weekend afternoon going out with him and one of his (still running another company) buddies could launch your career in another direction. Think of him as a resource and all you have to do is be yourself around him.

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New-Sheepherder-1664@reddit

Sounds like its a super well paid side gig.

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Helpjuice@reddit

Help with boundaries to include charging for your time, get a contract setup and you should be good to go even if it is just a retainer.

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Corgipantaloonss@reddit

Is there a reason you dislike this guy? He kind of just sounds like a friendly coworker/friend. Now if he's is demanding or really pushing boundries then you can make the call. But if hes been cordial about the personal things and thankful is there a reason you wouldnt want to help him out as a friend?

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tudaloo2u@reddit

Honestly, bite the bullet and help out if it isn't too burdensome. It is RARE to find someone at his level who did as much as it sounds like he did for you.

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djgizmo@reddit

jfc, he’s been your supporter for 5 years… and yet you’re going to abandon him after 2 months. shows a great character of yours.

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Ok-Strength-5297@reddit

he did completely normal things

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Nivosus@reddit

OP sounds like a person who did not deserve the success this CEO gave him.

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Ok-Strength-5297@reddit

Workers like him gave the CEO succes

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Nivosus@reddit

Re-read what he wrote and try again.

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MisterIT@reddit

Parlay. Don’t just keep helping him, invite him out to lunch and ask for career advice.

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Ok-Strength-5297@reddit

lol what

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Middle-Program-8839@reddit

I think you should continue to help him and feel like you can go to him for things and ideas/support. Turn it in to a two-way relationship where you both benefit. He sounds like a top guys tbh

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AgesOne@reddit

He’s done a ton for you it sounds. By the sounds of it he appreciates all the help and work you do anyways. I’d say help him out

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crispAndTender@reddit

Fwb situation, sounds like it paid off, id keep it going he probably had connections back to company regdless

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Extrogrl@reddit

Your decision has already been made for you.

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LegoRedBrick@reddit

I would never burn that bridge. Just accept the fact you can feel good about helping out someone older. Doesn’t sound like a burden at all.

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aek82@reddit

Man, just help him out when you can. It sounds like this guy genuinely appreciated your work and remembers you well.

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hammertime2009@reddit

If he helped you out that much then just bite the bullet and help. Probably just adjusting to home/retired life and needs to get a few things sorted. If he’s anything like my parents (who I always have to help with anything like this), then it might make sense to create a helpful document with step by step instructions for any recurring issues. My guess is he will eventually slow down the requests for assistance. If he’s anything doesn’t and a year + passes then maybe start explaining you’re too busy an he will start to seek help elsewhere, Google, grandchildren, etc.. I also think teaching someone like him how to use chat GPT could be helpful. It’s not difficult but some older people need a little hand holding at first.

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ExpressSelection7080@reddit

I think the best you can do is say something like,” sure Tom, I’ll be over soon, but I’ve gotta finish this first, I’m running behind.” Something to that affect where you aren’t saying, “ No,” but you’re still telling him you have other responsibilities and you’re pushing back. Tell him a little about your work issue or how things are going well with this project and you’re seeing so and so in an hour so he remembers you’ve got other ish to do! Handle it by giving some push back. OR- you can look at this as an opportunity to help the person that writes your bonus checks, that’s actually not a bad position to be in. Take the time to learn more about the company regarding things that benefit you, while you’re helping him. Use this time opportunistically.

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AlternativeMark4293@reddit

It’s your call but if it was me, I would definitely be more than happy to help out my former CEO on those home/personal IT things that he needs if he treated me well when he was the CEO. If someone built a business and has been a CEO, I don’t think he/she is too dumb to figure out his/her own personal tech support. I don’t think you’ll be your former CEO’s tech support for life :)

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-FakeAccount-@reddit

It kinda sounds like you should help him. I bet this fades out eventually, but for now i would probably help him.

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CoachMACC@reddit

You are his personal tech support for life. You’re correct. Change your mindset on it? Treat him like you would your parent calling for the same thing. Come to a place of acceptance and handle him with kindness. If it’s a big ask and you’re genuinely too busy to help him at the moment, *tell him*. It’s his company he’s going to be more understanding about waiting for an answer than your parents would. Then help him later? Sounds like he’s reaching out to his tech guru friend in his mind. With all he’s done for you, by your own admission, maybe you stop seeing him as just a former boss in your mind?

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HER_SZA@reddit

Just to add to the sea of similar voices-this is a great opportunity to continue to network through him. And he sounds like he genuinely likes you and appreciates how knowledgeable you are even now that he's gone. Go out to lunch with him time to time

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Altruistic_Mobile_60@reddit

It seem like he's a friend for life. I don't see why you want to burn the bridge.

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Ok_Anything_4955@reddit

You help him for all the reasons you stated. Retiring is tough on some folks, be a good human.

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Ok_Advantage_8153@reddit

Only an IT brain could be so tone deaf. This is a person you need to keep onside. I dont even know how this is a question.

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rockstar504@reddit

Friendship and morality aside... Most of the jobs I've got as an adult, and people I know as well, have been through networking. Knowing an ex-CEO? Yea, I'd want to keep that guy close and in my network. Who knows what could come of it. Maybe nothing, maybe something life changing.

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moderatenerd@reddit

I see a lot of people here are saying just accept the duties but there comes a point in everyone's life where you don't to help people set up iPads anymore. Being that guys IT assistant for years will stunt your growth and you will have less respect for yourself as time goes on especially since you already feel it. I started to transition out of this type of work a few years ago and now I am more a IT Business Systems Manager I don't know anything about the latest computer systems, networks, or how businesses set them up these days, just how my own part of the puzzle is setup and works. So I always tell people now that I can't really help. You can't make that transition in two months, but you can in two years and if I were you I'd start preparing for that eventuality.

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takescaketechnology@reddit

If someone scratches your back you scratch theirs.

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HustlinInTheHall@reddit

If he trusts you like this, then you it is up to you to decide if that is worth your time or not. You can definitely say no, but depends on how much you value him.

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engineered_academic@reddit

It's a question for your current employer. I would say "Hey, ex-CEO keeps asking me for help with his personal devices. I know my employment agreement says no moonlighting, etc so now that he's no longer with the company, how should I handle this? I want to be respectful to the company and the previous owner. As a lesson learned this is why i NEVER give out my personal phone number to work. If they need to cintact me, they can buy me a business phone. If he is calling you on your business line, now its a business problem not your problem.

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FieryHDD@reddit

I have the same issue, I just help the guy out. Getting paid to support People and man still has a shit ton of connections. You can use those connections when needed... Might be annoying now, but might profit in the figure.

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Byany2525@reddit

I would help the guy as much as I can.

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Nnyan@reddit

Why is this even a question?

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RightEquineVoltNail@reddit

If you can confirm that he still has some role in the company (ownership, board, anything), then treat the support as normal charged work. Otherwise do it for social capital.

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Brufar_308@reddit

I’ve never had a CEO ask me to do work on his personal systems without compensation. usually they ask how much for the work I tell them my price and they give me more than I asked for in cash. Wish they paid that well at the company. If the work is on company time sure that’s one thing, but if it’s after hours, weekend, at their home, that’s different.

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andytagonist@reddit

I used to have the retired owner with his name on the actual side of the physical building of the company his family built call me with computer questions at his home. Like personal stuff—Gmail, pictures, etc. He bought a MacBook when his entire career was spent on Windows and he called me regularly with help on it. I walked him thru setting up a printer at his home. He was a nice dude, quite understanding of all that he was asking for…but he was also asking for a lot. Long story short: my wife & I stayed at his BnB in the French countryside for two weeks a few summers years ago as a *thank you* for helping him. Lesson learned: know how to set the expectations, but also try to be accommodating whenever possible…especially to people who still have money & power in your realm.

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J22P@reddit

Dude…. Just do it man… go water his plants even…

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quartzguy@reddit

He sounds like a useful friend to have, honestly.

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usmcjohn@reddit

just become busier and less available...

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fromfreshtosalt@reddit

How much effort are you having to put in to help him. Is it a distraction to yourself, family, etc? I wouldnt burn the bridge unless he keeps calling during your family time or something. WHo knows maybe youll get a nice thank you gift. He better not come through with some 10 dollar star bucks gift card. And it wouldnt hurt to start off as a courtesy, but after some time maybe really have a meeting and discuss. Maybe in return he can incentivize it. A lot of these guys just think you click a bunch of buttons and settings and then its done. Far from it. Maybe you can introduce him to a company that helps?

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Downtown_Metal_7837@reddit

Sad that you’re even in this sub asking this question. Just do the right thing. You already know the answer.

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fdt86-47@reddit

Sure is a lot of CEO ball-gargling in this thread.

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Certain_Direction152@reddit

ITT: Reddit actually being reasonable for once. I'm impressed!

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x3thelast@reddit

OP are you rich or something? CEO is offering you a potential super cake job as a personal friend and tech nerd. Many of us do it for free to our family and friends. This guy literally threw money at you. Hell, I’ll be his personal tech support for life. ![gif](giphy|xTiTnqUxyWbsAXq7Ju)

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laosurv3y@reddit

Just take care of it. Do it during work hours if you can. The other execs won't appreciate of this becomes their problem when you could just deal with it.

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Jazzlike_Relation705@reddit

You sound thankless, my guy.

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BryanW94@reddit

I bet if you maybe go out socially like to the bar those calls stop and you get something out of it like advice or a continued relationship that'll only help you in his career and maybe he'll stop asking for it support.

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rividz@reddit

I wish anyone I worked for treated me with a modicum of the respect that this guy gives you. Help him out, keep him in your back pocket.

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Queasy-Elderberry-77@reddit

He may be retired but if he's a founder he probably still has an ownership stake etc...He's likely still up the org chart from you. Just suck it up.

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Ptbot47@reddit

Depend. I used to work in consulting and clients would sometime call me with questions outside our scope of work. In consulting they are very serious about not working outside the scope for business reason (youre incurring unnecessary cost). So I told my manager about it, but he told me its a good thing client calls you. It means they implicitly trust you, and them bringing you question mean they are bringing you problem, and our business is solving problem. So be glad they call, and thats how you lay groundwork for future business. Ofcourse you still gotta be smart about drawing the line, but its generally a good thing. In your case, i dont know if theres any upside to it, but who know what help you could get from him in the future. If its not too much trouble, and if hes as good a guy as you said, I dont see what's wrong what with helping him out.

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Situational_Hagun@reddit

It's up to you, but this is what sucks about corporate culture. That CEO didn't help you out. They didn't do you favors. You did your job. They paid to keep you working there. They promoted you because you did a good job. They didn't do it out of the kindness of their hearts. They didn't do it to be a pal. You don't owe that CEO anything. With that said the world isn't perfect, so it's up to you.

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hmtk1976@reddit

Indeed. The raises, bonuses and promotions were *business* decisions. Most comments here are a weird mix of naivety and extreme groveling.

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Restorne@reddit

"The CEO of my company has gone out of his way to treat me extreamly well, often giving me more and more money. Not to mention he's seemingly a very nice human who respects and cares about me." "Yo Reddit, should I tell this guy to fuck off since hes retired?"

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stacksmasher@reddit

Its a test. He knows he's a PITA and wants to see if you are going to bitch about it before he recommends you for a new role ; )

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HunterPractical2736@reddit

OP. Just know that my polite decorum is coming from a place of severe disbelief and white knuckles. You have an opportunity to make the CEO of the company, presumably a successful one, who has helped you and given you upward trajectory that most could only hope for, a friend. You are holding a golden ticket and asking us how best to wipe your arse with it.

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Level_9_Turtle@reddit

Figure out a way to playfully shame him for using you as his personal tech support.

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pjtexas1@reddit

Worked for my CEO for 18 years. Great guy and I owe him. He calls i fix or advise. He always stood by me. Even fired my boss for me and my team.

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Allah_Akballer@reddit

Your CEO sounds unreal, I would absoluetly help him out when he needed. I've been ghosted for raises more times than I can count.

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uhuhisee@reddit

This is interesting. My friend had the same experience you have. Friend worked in IT for a school, and somehow met a CEO of a bank. CEO would have house calls to fix internet issues, etc. Friend didn’t charge. Bank had an opening, CEO calls friend for an interview, friend is now lead IT of the bank. Massive pay increase, better position and lifetime of connections. Don’t bite the hand that feeds you.

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an0nyg00s3@reddit

Yeah dawg. You have a new friend now. If you show interest, you may even get invited to holiday parties, which are always fun

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Kuneria@reddit

Is being his friend so bad?

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CommunicationEast972@reddit

Help him, it will come back around with a ref or good biz karma in general

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realhumannotai@reddit

Help with his shit occasionally? Bro of course! DO IT. Why even think about it. By the way you phrased it, I thought he was calling you every day bugging out 24/7.

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Kind-Warrior-Heart@reddit

Consider him part of a valuable network. You never know when he will say something about you to someone that will make a difference in your career. He clearly isn't shy about showing praise.

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Pherllerp@reddit

Sounds like you guys are friends to me partner... You gotta help your friends with their computers sometimes.

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BreathlikeDeathlike@reddit

I'm honestly amazed at all the bootlickers saying 'he was generous to you, why do you even have to think about helping him?' He was generous to you because it made sense to him business-wise to retain you, and saw these raises and promotions as good tools for that. It wasn't out of the pure goodness of his heart that he was doing all this 'for you.' You were making him and his company far more $ than what they paid you in salary, raises, bonuses, etc.. That being said, I would probably keep helping him, for other reasons already mentioned (he seems like a good contatct to remain on good terms with, etc) but not because he was so good to you when you were an employee. Like WTF.

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jim_bobs@reddit

It never hurts to be friendly with somebody in high office and/or with good connections. You'll quickly realize how genuine or exploitative this relationship is.

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Overall-Avocado-7673@reddit

Sounds to me like he's given you quite a bit of security over the years. I have the same scenario with my old CEO. He still stops in occasionally after 15 years with a small repair project. I always help him out with material and/or labor. That's the way the world should work. He took care of me and I intend to return the favor anytime he needs me.

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jellomatic@reddit

I don't understand what the downside is.

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trombing@reddit

Just tell him to get rid of the HP and buy a Brother printer. He probably won't call you again after that.

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Odd-Resource3025@reddit

Ask yourself: Is this person someone I would trust to give me good advice? If the answer is yes, find a way to have them in your life. It's incredibly hard to find someone who is wise with the time to connect. Boundaries can help balance the requests. Please understand he is probably lonely AF, and it's hard to retire. You'll find the win-win.

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Apprehensive_Ear7309@reddit

Just help him out when you’re on the clock and you’ll get paid for your time. You’ll be compensated, nobody in the office will object, he’ll be forever in your corner. Problem solved.

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Tinnylemur@reddit

Man i wish I had the ear of the owner of my company. Every time he calls you about an iPad you have a chance to say "oh have you heard whats happening at [business]?" And spin everything in a beneficial way that will have a tangible effect on your life. When you apply for a promotion you can casually bring it up after telling him to turn off his pc and turn it back on again. When layoffs start, you're a face and a name to the company. Not just a number. I don't see how you can take this fantastic opportunity for granted.

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locke577@reddit

I helped my CEO build his house with all kinds of smart features, distributed audio, killer Wi-Fi, the man has a server rack in his basement. He took me in and always took care of me, and even though I don't work directly for him anymore, he knows he can call anytime.

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Perllitte@reddit

Seems like a vanishingly small way to preserve a very good and beneficial relationship. You don't have to race over for iPad support, but otherwise, who cares?

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skull-dog@reddit

Let's be honest. He was one of the few bosses who gave a shot about you. That's exceedingly rare. That being said, you're allowed to have boundaries. I just hope you consider this.

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rxvf@reddit

Wow you’re an ungrateful twat

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Extreme_Ideal_9884@reddit

I’d bite the bullet for now. If you’re still at the company and he’s treated you exceptionally well, helping occasionally is a fair trade retired or not, he still carries influence and relationships matter. Over time, you can gently create boundaries, but doing it gradually is smarter than a hard no. This is one of those situations where patience now protects bridges later.

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Longjumping-Tip1188@reddit

Just do it. Doesn't take much from you but the potential upside is huge

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Raah1911@reddit

Bro go to his house. Help him with his wifi. Sounds like someone who will do anything for you. You want someone like that in your life

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Few_Presentation523@reddit

OP you say this man helped you and his been really great about promotions and raises. Bite the bullet man. Like others in the comments say these are the types of business circles that are very VERY hard to get your foot in. Bite the bullet and take care of him when he needs help. You'll have another truck in your driveway sooner or later just from his influence alone.

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mdervin@reddit

Has he been a jerk about this? How complicated has his problems been? Is it just the setup between moving away from his professional tech to personal tech? If it's easy problems and he's been contacting you during work hours or "When you get a chance..." then keep on doing it. It's a nice feeling to help other people out, especially when they've made your work life quite easy.

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imnotasdumbasyoulook@reddit

bro gave you five figure bonus checks and you have only worked their 5 years? multiple raises and promotions? is this fake? you must be really young right? this isn’t your former ceo. this is a guy who thinks he is your friend. and if you aren’t the most arrogant and self centered person in the world you should start treating him like one. if he likes a good bottle of whatever bring one the next time you fix something for him. treat him like an elderly relative; set him up on a full apple ecosystem so they calls decrease in frequency if you can buy when you take that bottle or whatever gift would be appropriate over tell him now that he’s retired you wanted to thank him for all he’s done for you and your family treat other people the way you want them to treat you and see what happens; do set boundaries if he calls and you are having dinner or something tell him and ask when it would be ok for you to come by; he may be retired lonely and clueless and not realize everyone else doesn’t have as much free time and be like whenever you can

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RFDrew11357@reddit

I’m gonna guess this guy is old school. I’m sure he still has interests in the company. If you can do what he needs on company time keep doing it. After hours and weekends becomes tougher and that’s where you draw the boundary. If he calls you after hours and it will only take 15 minutes, do it. If it’s gonna take longer and it’s not an emergency tell him you’re busy and ask if he can give you a call at the office. Here’s where we come back to the old school part. You look out for him, God forbid you ever need it, he’ll look out for you.

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Dreamsofajourney@reddit

It's great he values you. I would keep helping him - can't hurt having a powerful friend but also, it's just the right thing to do.

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Sweetyogilover@reddit

he helped you get more money and now you don't want to help him because he is no longer the CEO. What is the problem?

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Sooooooooooooomebody@reddit

Consider your time spent on him as an investment.

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Throwaway999222111@reddit

Dude I would do anything for that kind of connection. Do not lose this guy

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Orange-Toed-Lemur@reddit

As someone who has left four jobs over unethical and shit management/ownership - I wish I was in your shoes with a "problem" like that. Five figure bonuses? Nothing negative ti say about the guy? Dude. Be a human

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prophase25@reddit

Wow, a lot I want to say here. I encourage you to consider _why_ humans evolved to cooperate. Natural selection does not select the nicest, most charitable people - it selects those most likely to survive. We help other people precisely _because_ they help us - we are selfish beings - and that is _okay_. You may think that continuing to help ex-CEO is charity. What you are missing is that helping him is actually the selfish option. It is in your best interest, because he has shown a willingness to help _you_. Check out game theory if you want to learn more.

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OliverHopper@reddit

Retired BUT does he still OWN part of the company? Also, seems like he has helped you and could help even more in the future

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Andydrooo@reddit

Sounds like he's been damn good to you.

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Fallout058@reddit

You just listed all the reasons why you should keep helping the man.

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cezreycor@reddit

You really doubting to help him?

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washedFM@reddit

Keep helping him whenever he calls. He sounds like someone where you should stay on his good side.

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SuitableFinish7444@reddit

Think of it as investing in your long term career. He is definetly telling people within the organization your helping him out. Also if you need a reference you have a CEO of a company down as your reference which i'm sure he would be happy to oblige to. Don't think because he's retired he has no input left in the company your in, of course he does.

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Plastic_Blacksmith37@reddit

I cannot believe how short sighted and just kinda gross this is. This is the type of person who post a job opening before obituary’s and probably shouldn’t be given power.

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tsereg@reddit

I have had people calling me like that, and eventually it stops. You won't be tech support for life. You should consider he is settling in his new jobless life, possibly feeling lost, confused, and what not as people who derive their life meaning from their work sometimes do.

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Dry_Gene560@reddit

Dude. As a founder myself, this guy will be a lifelong job resource for you. Just help him with his email.

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thatsjor@reddit

Do not equate being paid for work with friendship. While you got crumbs, he got real wealth, and somehow you feel indebted to him. Crazy.

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overworkedasian@reddit

be nice to him and try to help him out. for what may take 5-15 mins of help over the phone, would mean alot to him. you just never know what will happen in the future or if your paths will cross again in a positive way. im sure he has alot of connections that he has made over his lifetime, some of which you may have access to if you ever call upon it.

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Greatsnes@reddit

Nah man be a friend. You also do **not** want to lose that connection. You never know what could come of it.

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canadian_sysadmin@reddit

I generally don't like doing personal tech support, but for certain key individuals, it can sometimes pay big dividends. Honestly there's one or two past CEOs I would definitely help, if they called. They often have massive networks and it can lead to interesting opportunities (or side perks like 'Oh hey, thanks for helping, feel free to use my beach house in Mexico whenever you want' - true story). You can also help, but don't make it your first priority. Kinda a personal call depending on your priorities. Something you have to learn to navigate.

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jimsredditaccount@reddit

This is how the world works. It sounds like it’s a mutually beneficial relationship. These things sounds like very small inconveniences. I would suggest looking at the bigger picture. This person has helped you tremendously and sounds like he would be a valuable asset to have as a friend. This might also be this persons way of keeping in contact with you. Bite the bullet. Help him when he asks and remember he probably has contacts and other friends that could come into play somewhere down the road. Don’t burn this bridge.

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JBRifles@reddit

The secret to success is keeping successful people that can stand you in your life.

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bananataskforce@reddit

I'd do the work for free. He no doubt has great connections and can help set you up for good jobs in the future.

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Both-Leading3407@reddit

Do it and be happy?

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PerformanceLast8554@reddit

Just do it, could help sometime in the future.

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zomgitsduke@reddit

You start seeking his advice and wisdom while helping him. "How do I get to admin level with the company?" "What can I do to achieve wealth rivaling yours?" Shake him down for so much advice. Also, "Oh, my kids really want an ipad but I don't want to break the bank on one without getting some advice, you like this model?" Around holidays.

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porcomaster@reddit

it looks like you have a friend for life, not a CEO. i would actually get closer to him, next time he asks for your favor, help him and invite him for dinner. he does look like a nice guy, and might be asking you for help just because he trusts you not because he needs you. that is what friends do.

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ReactionJifs@reddit

Important to consider he may simply want someone to chat with, or a project to work on each week. Otherwise, I would consider building out a document for him to assist with his most frequently asked questions. If you can list ways to troubleshoot his issues, he could ultimately become independent, but that may not be his goal.

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Real-Information1886@reddit

I don’t think he’s asking for a lot.

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original_gravity@reddit

Yes. Keep helping him out for goodness sake.

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favorite_username@reddit

Come-on, I hope you are not serious

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Mrbutter1822@reddit

Help him out, he clearly helped you greatly. Whatever you do, please don’t go to r/antiwork for advice

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BryceKatz@reddit

This is a great example of how maintaining that relationship may will continue to help you. Retired folks talk. A LOT. And they have far more time to hang. You never know when the right word goes in the right ear. I'd help him, but outside of business hours.

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Vargenwulf@reddit

You have the trust and respect of the guy who founded the company? You keep saying yes, with a smile. That is a relationship you never want to burn. It will help to protect you and likely help those bonuses keep rolling. He may be retired but as the founder I can guarantee his words still pull a lot of weight.

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onlyhere4gonewild@reddit

Speaking from experience, I've seen former business owners struggle with retirement, regret selling their company, then starting a competing business within a few years. They poached all their former favorite staff with better pay. This could work out for you by staying friendly.

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AbbreviationsNew764@reddit

how dumb are you to even ask this question...these are the type of people you absolutely keep in your orbit at all cost...it sounds like the man put way too much faith in you to begin with if this is how petty you are...

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RedditIsSocialMedia_@reddit

I'd think of it like this.The odds are he probably still has sway at the company, helping him help you later

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No-Elderberry-7695@reddit

If you're his go-to IT guy, you'd be high on the "people to call list" if anyone asks him for recommendations or even if he's looking at founding something new. If you are spending lots of time on his requests, he will recognise the value of that time in some way.

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AdSmall3663@reddit

Help him, he also likely has good connections so use this as an opportunity to possibly have him help you further

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SlipBusy1011@reddit

Give him some professional courtesy, a few minutes here and there, more if you are friends. Then if you really want it to stop then start taking longer and longer to get back to him. He'll then start taking the path of least resistance by asking someone else who will help him timelier.

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Gloomy_Concert1755@reddit

Nah give the guy a hand. He sounds like a mostly friend. Relationships in life and business are worth keeping even if there a little hassle. Business wise keep that bridge, human wise be a good friend.

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pablo8itall@reddit

I deal with a lot of retired staff members. Most have earned it. Look at it as community service. Your good deed, he sounds like a generous soul and deserves some help in his old age.

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lukehooligan@reddit

Give him my number, I'll help him out since you don't want to. I've been my family tech support my whole life and never got a bonus check.

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maldax_@reddit

TBH He sounds like the type of guy who wouldn't expect something for nothing If it were me I would go with the flow

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Amdaxiom@reddit

Still helping the director of a company I used to work with 20 years ago. Just setup a new Windows 11 laptop for him. He is always grateful and pays me for my time though but he's been a good friend so I help him out as much as I can

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Adventurous_Bar_1228@reddit

absolutely continue to help him. If it makes you feel better consider the payment all the past benefits he's secured. If the work is onerous, or unreasonably frequent you should set small but reasonable boundaries such as scheduling it on a weekly basis or asking to call back and follow up at a better time.

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SuddenlyLegible@reddit

Hey chat, there's this guy that calls me once a week for tech support. I mean, I try to be nice because he has paid me well for 5 years, gave me raises when I asked without a fight, always told me how much he values my work, given me 5-figure (XX,YYY) bonuses, and still knows a lot of the higher ups at work. How can I politely tell this guy to fuck off without getting in my own way? op you're fucking up

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frankc420@reddit

Bite the bullet. It's very little time from your day, just make sure your boss knows this guys is calling you asking for support. Make sure the old CEO knows you've let your boss know and any help really needs to be during business hours. This way you are theoretically being paid for the work. I feel your pain, I hate doing email setups.

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drunkhas@reddit

Subtly nudge him into getting a Personal Assitant.

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veracity8_@reddit

is it possible that he’s looking for a friend?

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Fus_Roh_Dayumm@reddit

This is called a high value connection. You go and set this man's entire home theater system up if he asks. He is connected enough to provide you job security and he will be helpful past your time at that company. Help him. Be his friend.

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HeligKo@reddit

You can view it a few ways 1) It is beneficial to keep him happy. 2) You like the guy and want to help, but might need to put up some boundaries in the future to protect your time. 3) The company won't be the same without him, and doing this isn't going to get you ahead anymore, so you want your time to yourself and are probably should be looking for work elsewhere.

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whomad1215@reddit

is he doing the boomer thing of asking for help so he can see and talk to you? because I'd lean towards that over them actually having basic issues they couldn't figure out themselves

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MissAutoShow1969@reddit

Just because a CEO moves on, doesn’t mean there’s not another business opportunity on the horizon. Besides, you can delegate the request to a trainee. But yes, some people get a lifetime pass because they gave you your prosperous life, but you can close doors on relationships that no longer sustain. That’s between you and your conscience.

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FinishingMyCoffee1@reddit

Just help him on the clock. Win win.

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taswind@reddit

Unfortunately, I can't tell if he is calling you on personal time or during work hours. If this is during work hours and the company is okay with you supporting him, please feel free to ignore the rest of this comment! One company I worked for had personal IT Support for the highest C-Suite people built in to the "contract." It was a little weird because the IT Department started as in-house IT for a non-profit organization. At some point, the non-profit told the IT Department to go fund itself and it became a MSP with regular ("external") clients in addition to the non-profit parent ("internal") organization. The non-profit paid for the home/personal services as part of the contract. Might be a little kludgey to adopt as in-house IT for a former employer, but I would definitely say doing this during work hours and treating him as a regular employee would be a fair compromise - as long as the company signs off on it.

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Fabbio@reddit

YTA.

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indiana-floridian@reddit

He's already bored being home. Keep on his good side. It's very possible he's thinking about what to do next. If you have ideas, say so!

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Beans_SupremeX3@reddit

Do not repay that kindness with enmity. Handle them like a grandparent.

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Heartsolo@reddit

What an absolute prick for even asking this

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j4ckofalltr4des@reddit

So long as he's not bothering you after hours, I say help as much as you can. If you are dead in the middle of something, maybe you have to call him back when you can, but still help

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WWGHIAFTC@reddit

Set up Friday meetings with him every other week at 3PM. You go, check on his equipment, see it he has questions, and he pays you in sipping $1500 bottles of scotch until 5. It's would be a great break from work. Sounds like he's still a part of company culture, don't burn that bridge yet.

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SerendipitySue@reddit

his retirement may be a temporary thing. do not burn that bridge

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Axel-Adams@reddit

Bruh the CEO’s network doesn’t retire, do you understand how good a position it is. You’re fixing the man’s computer and can ask him for good investment deals or connections.

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Richyrich619@reddit

You help this ceo hell will help you hes shown that. Even if hes not the ceo now he can still help you from what hes said.

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1968GTCS@reddit

I would bring this situation up with your superior. There may be an agreement in place that you are unaware of. If there is no agreement, then it is best to set expectations earlier than later. He may have done a lot for you but that was his job as your employer. Are his requests cutting into your personal time or causing you to miss time at work?

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RadlEonk@reddit

This thread is crazy. He was a CEO, not a charity worker. Sure, most CEOs are terrible so one that seems like a not terrible person feels like an angel, but you don’t owe him anything. You worked for a salary, which the company paid. That’s the agreement. He wasn’t handing you cash from this pocket. (And if he did, he expensed it.) If you don’t want to be a personal IT support, find a way out of it. Start telling him those days don’t work for you or you’re not familiar with the tech, he’ll eventually find someone else. Also, it wasn’t said, but I assume he’s compensating you for these side efforts. He’s not your grandpa whom you help out sometime. Personal visits are not part of a professional role. Some other poster said they’d fly to Florida to help retired executive’s family? Are you crazy?! Work is work. They shouldn’t be abusing the resources - computers, licenses, discounts - or staff of the COMPANY for personal use. Some of you need to grow a spine and say you won’t help non-work projects. Utterly ridiculous.

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hmtk1976@reddit

Ah, someone with a brain! I agree with everything you just wrote. Quite a lot of people who like being serfs here...

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ConferenceThink4801@reddit

If you really hate it, I would just make it more & more difficult for him to get you over there rather than say no. Delays, etc, until he gets the hint. If you don't hate the guy though then you could actually view it as just helping out a friend. Although a friendship isn't 1 way traffic & doesn't always involve 1 person doing something to help the other. Where it gets complicated is that he probably feels he already did a bunch of nice stuff for you...so

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QuellishQuellish@reddit

I have a very similar situation at my job. Both of the founders of my company hit me up for help with their personal projects periodically. I always say yes. I Just ask them if it's important enough to move stuff around for or if this is a "when I can get to it" type thing. Then I tell my manager that it's going on and that I'll loose that time on something else. I owe those guys a lot and don't mind doing stuff for them. It's all on the clock and management knows. This arrangement has secured my position, not just by helping them but more importantly, all the managers know the founders come to me personally and value my skills. It's like 4 or 5 skip levels, I've got a personal relationship and most of my managers have never even been in the same room with them. All else equal, I'm not on the layoff list where I might have been otherwise.

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crankysysadmin@reddit

It sounds like he is "retired" but still is part of the organization, so if you don't help him things will likely not go well for you. If it is quick questions, you may just need to put up with it. You can try to manage him a bit and maybe don't provide absolute immediate responses and tell him you have to do X for the company first but can work with him later. I would also check with your boss for a little guidance.

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iexsist@reddit

Sounds like he was a good guy like a lot of other people said and unless he’s calling during odd hours when you’re at home and only calling you at work it’s not a problem. He may have an agreement with the current CEO that he’s allowed to use your services. As a director it would tell you just take care of a guy he did right by you. He’s doing it on company time so go ahead. We do the same thing for our executives and retired executives. If they were good to us it’s snow skin of your back if you do it at work

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pigoath@reddit

That's the problem of gratitude. When does it stop? Anyways, you're just an employee doing your job to which you were getting paid for. You can be thankful and help out. But it's up to you how you handle this and how he handles people putting boundaries. You gotta know who you're dealing with and then you act. But again if it's just a small favor without pressure. It shouldn't matter much

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taxman691@reddit

Chances are while retired, he still got connections in that company. I’d use this as an opportunity to get a new (retired) friend. Legit sounds like he trusts you enough to call you inside his house.

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ExceptionEX@reddit

I ended up supporting one of the greatest CEOs for nearly a decade after ye retired, and was happy to do it, his problems were simple usually didn't take much time, and he was kind and respectful.to me when many in his position wouldn't have been. He was also responsible for me getting a sizable increase in pay. He was grateful.till he passed. My current direct is about to retire, and I'll probably do the same for him. It's just always felt like the right thing to do.

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vivienleigh12@reddit

Suck it up buttercup, and don’t burn a bridge

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merkthejerk@reddit

Send him a bill

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BigFuckHead_@reddit

Dude just keep helping him. It doesn't sound hard and you can think of it as just helping an elder friend.

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dubs1782@reddit

After ALL he's given you... you are considering dropping him like a hot potatoe because you don't see a direct benefit for you in the future with this relationship??? If a CEO (current or former) has you in his short list... it's a privilege. You're the one getting the privilege, not him!

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MandeliciousXTC@reddit

Jesus - just get it done. I’m surprised you’re asking this question.

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darknessbelow@reddit

He’s your friend now

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MonkeyMercenaryCapt@reddit

Sounds like he changed your life fundamentally for the better. Help the guy out, he seems cool, if at any point it starts feeling like a big burden hit him with the "I would love to help you, I'm slammed, could we do a scheduled weekly check-in? Shotgun all your stuff at once?"

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Ok_Cow6845@reddit

Can't go wrong being on good terms with the former CEO of your company and helping them, seeing as it's mainly just tech support stuff you're helping him with, and considering everything he's done for you

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The_Kielbasa_Kid@reddit

Are you hiring? Sounds like a great place to work!

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Practical-March-6989@reddit

Keep dudes like this onside my friend, trust me.

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SmokeySFW@reddit

Not only should you help him, but I'd even say you should be happy to help him (within reason). CEO's like him know lots of people in high positions in a lot of companies, there may come at time where he might get a chance to "scratch your back" again. Just bite the bullet on this one, these kinds of business relationships are worth keeping.

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uswforever@reddit

Sounds like he's been a right gem of a boss for years. I'd stay helping him out just for that. BUT, I'd make sure I always did it in company time. Lol

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RedWineChocTart@reddit

Be good to him. It sounds like he was good to you.

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OkDimension@reddit

From the way you describe it it seems like he went above and beyond for you, so a bit extra care even though he officially retired doesn't hurt. Seems he is still well connected and influential in your company so I def wouldn't try to upset him. If it occupies too much of your regular work day you might ask your current manager/CEO for some assistance, either a junior running the day jobs in the office while you're assisting the ex CEO or vice versa. I'd try to set a boundary that it doesn't overlap too much with personal life (off work time), but as long as current leadership is cool with supporting ex CEO during your hours I'd just keep doing it. It's a quite common thing in family founded/run business.

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Present-Event8783@reddit

Older people often need emotional support and all over the world social support systems for older people especially for men is gone. Once men are past their earning phase society would like to forget them. He might find more in these interactions than you can imagine. It shouldn’t burden you however. Does he have a friend circle?

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nomhak@reddit

Homie, how is helping him out going to lead to anything but a better outcome for you? You’re making him sound not only reasonable but incredibly generous, relationships like that are worth nurturing because where they have the potential to exponentially improve your career and life. Him asking you for help goes both ways - ask him for career advice, introductions, etc. Read the book ‘How to make friends and influence people.’

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BitterCaregiver1301@reddit

Yeah I would keep him sweet for the time being.

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SpazMcMan@reddit

Echoing what many others have said, you should absolutely still help the guy. I've been in this situation with two former CEOs, and helping them out was the right call in both cases. Both of them helped me immensely in my career, one by getting me referrals for when I went to work for myself a few years later and the other bringing me in as a partner in his next startup years later. A lot of these guys see these one offs as a sign of friendship and trust, which they value more than a transaction with "the help", so to speak. Unless it gets to be excessive or bothers you a lot, I'd help him out and use him as a mentor, as others have suggested.

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HeWhoLovesMonsters@reddit

Help him out my dude? Just seems like the right thing to do?

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woo0lyhat@reddit

Jesus Christ you ungrateful sod.

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7-roses4humanity@reddit

Just do it…i would be more than happy to do it if it were me..

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ArwiaAmata@reddit

Or, if you like him enough you could make him a friend. That way you both get something out of it. Thing is that, even if he's annoying, he could still be influential and help you in your career. It's up to you to determine how much that's worth to you.

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NoobToobinStinkMitt@reddit

If it's during work hours I would just suck it up and do it.

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PaisleyComputer@reddit

Is he asking you to take off your pants? What the hell, reread what you wrote about this dude. Yes, help him with an iPad from time to time, or give.him my email and I'll happily befriend a titan of industry.

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riftwave77@reddit

Give it time. This guy just retired and hasn't had time to build a social network outside of work. 100% help him with his stuff and see if you can't steer him toward gatherings or social activities where he can network away from a professional setting. Running tech support nowadays is much simpler than in the late 90's or early 00's when you had to deal with modems, credentials, limited drive space, dodgy web browsers and people to naive to understand what spam was. He'll eventually get to a normal steady state with his iPad, PC and email. Browsers save passwords these days and interfaces are much more user friendly than they used to be. Being relied upon for 1-2 hours a week worth of help and advice is no price at all for the benefits you say you have reaped from this relationship. I think you have a ways to go before you need to consider getting serious with boundaries.

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silly_little_jingle@reddit

This sounds like an incredibly easy answer. He sounds like a good boss. A generous man and if he’s been that good to you I think a call here and there to the guy whose name is on the side of the building is a small ask. Don’t burn a bridge you’re still walking on.

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Techdbltime@reddit

Bruh, help the dude. Sounds like he gave you a ton.

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Mysterious-Ad7547@reddit

Every single CEO etc I worked with that helped me I have always helped them if they asked me. It will drop off as time moves on it always does.

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reddit-trk@reddit

He's making a lot of deposits in what I call the "favors bank." You're not obligated to return all his calls immediately, since he isn't a paying client, but be courteous and do what you can to give him a hand. As someone wrote, and as your post indicates, this guy's in your corner. Good will goes a LONG way.

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mediaogre@reddit

This retired CEO does *not* sound like your typical, tone deaf, do-more-with-less, entitled CEO. Keep graciously helping him but set some boundaries. Have a human conversation with him, tell him how much you appreciate what he’s done for you and give him a couple specifics. Ensure him that you want to keep helping him but if a work priority comes up, it’ll have to wait. And if you’re not expected to answer your phone for non emergencies during non work hours, that also applies.

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Pure_Fox9415@reddit

Stfu and go help this man all you can. If it will be overwhelming sometimes, just tell politely, that you are in emergency now and send somebody else to help

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F1Phreek@reddit

Do NOT fuck this up! He recently retired which means he still has influence on the new owner, board, etc. if you piss him off he’ll complain to everyone about it. Eventually someone will tell you that you need to help him and you’ll still be helping him without any of the positives.

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tdressel@reddit

This is not always the case. Unless you know the exact circumstances of the CEO's departure, don't assume he has influence anymore. I've worked for two CEO's who were pushed out. And as nice as they were to me, any association with them became very toxic, especially about loyalty to the company versus loyalty to the old employee. I see tons of comments here suggesting to continue to carry on a support relationship, my recommendation is to tread extremely carefully.

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jetblakc@reddit

Sounds like this dude has already given you more than some people get paid to do that job. A lot more. I would just keep giving him the support: you're supposed to help people that help you. This is a pretty obvious situation where selfishness is a bad choice. I would say to help him even if he hadn't made you wealthier by at least five figures maybe six figures considering bonuses and raises. I think it's the right thing to do, but if you want to be hyper rational about it, do the math on how much work you're actually doing for how much compensation you've received.

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neityght@reddit

He sounds like a good guy. You sound pretty ungrateful and are acting like a bit of a dick. Why not be a good guy back?

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No_Significance_4118@reddit

> Why not be a good guy back? Because OP is a piece of shit...

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UnMeOuttaTown@reddit

My previous boss was almost like a really, really good friend - she was and is very talented, quite empathetic and she became a leader at a very young age, so she was skilled technically and management wise. She was extremely helpful and was quite protective of her team (us). We set up monthly calls once she moved to a different company - this is just a way for us to discuss and share general stuff. She advised me about how I should negotiate a raise and a promotion. How I should discuss about bandwidth and stuff, and sometimes we even discuss about how she and husband are working on their golfing skills, or how a certain company's upper management is working. Just a mixed bag of things, but it is always better to stay in touch with your well-wishers. My opinion, at least.

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tdressel@reddit

Ghost him, then if you ever bump into him just make up a story about how busy you've been since the new CEO arrived.

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BrokenBehindBluEyez@reddit

I ran into this early in my career with both managers and front line employees. At some point I just said "hey I do this on the side now, I charge half of best buys rates but it may take me a bit longer". I was never ever turned down, made decent money and typically tips from mgmt folks. People often just want someone they can trust to help, and shockingly will pay pretty well for it. If not it becomes awkward for them to ask you to do it for free.....

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hmtk1976@reddit

I strongly disagree with all the comments that say to just bend over because he was a good employer and he may still have some influence. You can and should appreciate what he has done for you - which were also business decisions on his end - but he can´t expect you to be available for him now. There´s a good chance he´s honestly not aware that his requests are not ok. If he calls you off hours, he should respect your privacy. If he calls when you´re at work, he´s using a company resource. This may or may not get you into trouble with your employer. Just ask him what he expects from you.

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CanadianCigarSmoker@reddit

Change the name on the business to yours to assert dominance. Just kidding. All jokes aside. Yes help him out. If you are busy, which is normal, send a junior tech.

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Tech-Sensei@reddit

This is a great setup for a casual conversation with him for advice on your future. If it were me, I'd continue to help him and ask, "In your opinion, what do I need to work on to become a Chief Information Officer?" I'm not sure what your aspirations are, but this may set the stage for a very lucrative future.

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No_Significance_4118@reddit

He sounds genuinely nice and did so much for you and you are looking for a way to get rid of him?? > Do I just bite the bullet Sounds like you are a piece of shit to be honest. Fucked up personality.

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Turdulator@reddit

Hes helped you a lot, so I think it’s the right thing to do to help him out. I went through something similar, I think in your case it’s the right thing to do. Plus, from a purely selfish point of view, it’s worth keeping the relationship going because he probably has a lot of connections that could be very helpful for your career.

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admiralpickard@reddit

Keep in mind just because he’s retired doesn’t mean he’s not still a valuable reference for you. He still knows lots of people.

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chodan9@reddit

Ive had that situation before, it tapered off after a while and the finally stopped, I think she finally felt guilty lol.

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ConfidentExcuse9857@reddit

If I were you, I wouldn’t hesitate to help him out. There certain people I go above and beyond to help out and he falls in that category.

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DeadbeatHoneyBadger@reddit

He may have retired but he’s still influencing the company. He still indirectly signs your checks. Don’t fool yourself.

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Krelik@reddit

I had a similar CEO before & during covid. Dude approved massive bonuses, listened to my input, basically everything you said. He left and started another business and paid me 5 figures to setup the networking, M365 tenant, and like 10 computers. He also paid for the flight and hotel. I told him that was too much and he said "I know" with a smile. You better believe I answer every fucking phone call from that guy.

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Big-Routine222@reddit

This sounds like one of those things where if you deal it up, you might find yourself in an amazing position later. Sounds like he’s already helped you too, so I’d be patient and give him some slack

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failtuna@reddit

Oh my life is so hard boohoo I have to help a wealthy man who helped me stay out of poverty. Get a grip.

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four_reeds@reddit

Not only is your ex-boss a marvelous human, he is an excellent role model. As you progress through your career, remember your boss and how he treated his employees and try to make that same impression on your employees.

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mandrack3@reddit

Man forget he is/was a CEO, sounds like he saw you as a human, and really appreciated you. What does it cost you to offer that kindness in return. Relationships with ppl are a gift that keeps on giving.

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GuitarStu@reddit

This is more than likely temporary. He's in a new life situation and trying to get acclimated. If it continues to persist, just kindly recommend a local PC repair company to use. Just tell him that they are a business that you trust and recommend to your family and friends when they need IT help.

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johnwestnl@reddit

To answer your question: I wouldn’t say no. I’d be happy for every opportunity to listen to him.

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Harfosaurus@reddit

He sounds like a stand up guy so I'd help him out as much as possible. Plus, you could just do it on company time and get paid for it

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strawberryjam83@reddit

Sounds like your default answer is no, but you are thinking about saying yes. Considering he sounds like a good guy is imagine your relationship moving forward might also be a good one. Now he's not paying your wages he may even offer to pay or tip you.

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Doso777@reddit

Help him on company time, check in with whoever is in charge now to make shure it's okay.

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Jackyl_and_High@reddit

“Right relationships lead to right resources.”

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GigglySoup@reddit

If someone did half of all that for me, I'd call him often to ask if he needs help and jump right at it when he calls.

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Able-Ambassador-921@reddit

Only "snub" him if you're moving on. He still lunches with the people that pay you. As long as he's respectful i would provide him reasonable IT support.

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Pleasant_Expert2258@reddit

Could it be that asking you for help is a way for him to still feel connected to his firm? If so, the calls will get fewer.

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inarticulateblog@reddit

I would help him based on how kind and appreciative he was of my labor when he was CEO. It sounds like he still views you as a friend and you might be the only support system he has for these tasks. Also, his social equity did not go away because he retired. I promise you that his opinion of you, poor or otherwise, can still effect your standing in the company and maybe other places. What if you want to take a much better position at a competitor? Do you know how important and meaningful a letter of recommendation is from a former CEO of a respected company in your industry?

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Kittamaru@reddit

You definitely want to set reasonable boundaries (no 2am calls for example) but, he sounds like a genuinely good dude and the kind of person whose orbit you want to stay in. If he is looking for significant support, it may be worth proposing being "on retainer" for him as a personal IT Support tech, either as a consultant or other such independent employee. Nothing extravagant, just something to cover your time/opportunity costs. If it's just the occasional call, I'd say just consider it a part of being a good friend.

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marcelbrown@reddit

As an IT professional who has worked with small businesses and in-home clients for the last 30 something years, my experience says that he will probably need more tech support now while he is transitioning into retirement, and it will level off in the long-term. So this once a week thing will probably not be for much longer. That being said, you can draw boundaries around when you can be available for support, and also talk to your immediate supervisor about the situation. If they are cool with it, then it just has become part of your job duties. But if they are not cool with it, then more formal arrangements can be made.

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thetimehascomeforyou@reddit

He’s testing you. Keep playing ball and you might reap more than you sow.

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MAndris90@reddit

if he was good with you outside of work. why not? you will never know when you get an opportunity thanks to him, remember buisnissman who retired from his own company have friends in high places.

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OddWriter7199@reddit

Is there a friend/company/service you can refer him to when not available?

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1meandad_wot@reddit

We have a SVP/name on the old company guy that does this with me. He helps out my family with various things outside the work space. He is my friend and I will always give him a hand.

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Sensitive-Split137@reddit

If he was good to you return the favor, does not matter that he no longer works there he could also still speak up for you if needed in the future with his connections as well.

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PappaFrost@reddit

I'm reading all of these comments. OP said he is getting called once a week for tech support. That is 52 random calls per year, probably in OP's free time. That is free 24/7 on call support for him personally. I question how good of a deal that is for the OP. You are a professional, not the neighbor's kid who is good with computers. You should come to a mutually agreed upon official paid arrangement if you want to keep doing this. If you want to be on call for this guy, make it an official paid thing.

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DV8y@reddit

You have your answer so re-read what you just wrote any time you question why you are being kind back. Few have ever had such a supportive employment situation. You are lucky even if you don't yet fully realize.

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Mdamon808@reddit

If it bothers you working for him for free, you may try telling him that you are happy to keep helping him. But you need some sort of compensation for the work you are doing. You can even set the cost pretty low if you really like the guy and want to keep helping him. But what ever you decide to charge, it will make it clear that this is more of a transactional relationship and not you helping out a friend.

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NomNomInMyTumTum@reddit

Same situation and yes, I help him out as long as he comes to me (company property) and I do it on company time, no home visits or after hours shenanigans. I also try to do it in a way that he can become self sufficient in the long term (and he is).

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Klutzy_Scheme_9871@reddit

Dude I even help people who never helped me like that. Yes you do owe it to him but even if you don’t, is helping someone so hard these days?

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perthguppy@reddit

There are the sort who are out looking for a free lunch, and then there are the sort who build out a network of trusted go to guys who all look out for each other. From what you said, this guy is the latter. You want to keep a good relationship with him, he knows everything in the world is transactional, you’re helping out him right now with your skills, he’s going to be happy to help you out with his skills if you need it later. Be polite, be honest, and be upfront. If he calls you asking for help, view him as a friend, not a work appointment, if it’s not a good time, let him know you’d be glad to help out but your busy right now. One day there’s going to be a good chance someone in his network is going to mention needing a great IT guy for some key project, and he’s going to tell them to come see you. His world works on who you know not what you know.

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Sutaru@reddit

Man, it sounds like he really took care of you. Even the bosses I liked did *not* say “absolutely” to multiple large raises. I’d help the guy power cycle his iPad for at least the next 5 years lol.

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beheadedstraw@reddit

It’s not what you know, but who you know. That’s a good person to know.

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burgersnchips87@reddit

Given everything you said, I don't think occasionally helping the guy with his iPad is a lot to ask

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FlyinDanskMen@reddit

10k bonus checks should buy a shit ton of after hours. Def bite the bullet and have your name in his mouth all the time brother. This is a good investment.

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rufus_xavier_sr@reddit

Sounds like a good guy and you should help him. He might even throw you something extra. I had something similar, but the guy was an asshole. I told him he wouldn't like me when I'm off the clock. He took a few seconds and said, okay.

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Festernd@reddit

5 figure bonus check buys a lot of goodwill and, honestly, low-effort tech support.

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thebemusedmuse@reddit

I don’t get it. Won’t you be helping him on company time? At some point I’d probably clear that with your boss but it’s a win win isn’t it?

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flying_postman@reddit

OP you NEED to stay close to him because especially in these times where highly qualified people are being put through five rounds of interviews for junior positions. He will be a great asset in your network to reach out to in case you need to switch jobs.

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linniex@reddit

Bite the bullet my friend

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jailh@reddit

As other said, it looks like this guy was there for you, so you can be there for him and help without feeling exploited. But it's YOUR time : you should suggest him to call or meet after work, so in the end he understand that you do it for him, not for the company.

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Txboyalone57@reddit

Of course you help him out. You never know where it may lead. Give the guy a chance.

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Danielle_is_the_hole@reddit

You gotta figure he made 10 times off your work than you received. Once in a while say you are busy at the moment but will call him back. I would still call him back eventually.

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gatnic@reddit

Are you using company time and resources to provide the support? If so, make your boss aware, if they aren't, and keep doing it. You are getting paid, the company knows, and the political capital you are earning is gold. If not, try to switch that over. If you can't switch it over, set reasonable boundaries. No late night emergencies that aren't real emergencies. No holiday work. No farming you out to others. No matter what, keep helping a great dude that has gone to bat for you. Retired or not, the political capital and good will of powerful people is worth more than money.

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223454@reddit

I would try to do as much as possible during business hours. You don't want to set the precedent that you're his 24/7 tech support. But definitely keep helping as long as it's minimal.

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Klutzy_Scheme_9871@reddit

Just help him out occasionally. He’s helped you out. Once a week is not that bad.

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Important-6015@reddit

Sounds like you hit the jackpot. Hell when he reaches out, ask him about his family and health. Maybe have a beer with him when he’s in town.

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hurlcarl@reddit

I do all that and more for family who dont do shit for me...this guy sounds great and someone who'd be great to have ariund in general, i get its annoying but id bite the bullet

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msavage960@reddit

Help that man! You never know where a friendship with someone like that might go. He sounds like he likely has a lot of knowledge and wisdom under his belt and maintained a level head after all those years.

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math_rand_dude@reddit

Do you supervise people where there is someone that won't backstab you? (Preferably some recent grad with good work ethics) Next time ask if you can come over with someone, tell him you're teaching that young one the ropes and that helping the previous CEO can be valuable lessons. Other option, if the old CEO is still friends with all the others, ask if you can work from home one day a week and allocate some time that day (maybe 1 hour or so) to go help the old CEO in person. If anyone in the C-suit denies that request you got a scapegoat to throw for the old CEO. If everyone approves, you got one more relaxed day per week.

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AdvancedGeek@reddit

Are you providing this help without charge? If so, then you would be demonstrating that your time has no value. You should set up a sole proprietorship on the side, track every call and related work you do for him, and invoice him accordingly. You should also send him a contract that defines the work relationship you will have with him. If he declines, then you can ask him if he worked in his previous role for free.

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Ansible32@reddit

Do not work for free. Be diplomatic about it, but either make sure he is paying you above-board and the company knows about it, or the company is officially offering personal IT support for him. If he's the kind of connection you want he will appreciate you setting the boundary that your services cost money. Unless you can see some way his influence can directly translate into 6 figures of extra income, it's not worth working for free.

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apotrope@reddit

I don't think it's wrong to be thinking about a boundary you want to set. Even between folks who've helped each other out, there's always a limit that needs to be gently reinforced. - Never prioritize his asks over your daily tasks unless it costs you nothing. - Make a plan now with people you currently work with to set 'offboarding policy', so that it's clear to everyone else in the company what the expectations will be when they leave. - For the former CEO, gently let him know if his requests conflict with your responsibilities and expect the same cordial flexibility he is asking of you.

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stedabro@reddit

I don't think there's a right or wrong answer here. It sounds like you would continue doing it if he was still the CEO and it seems like you have some warm feelings towards him. However, politely saying no... could involve a recommendation to a support center, another IT person, etc. "I know a great IT shop that can help you with these going forward." Perhaps at least researching what that looks like would make this feel less like an obligation and more like an intentional kindness in response to what he has done for you before. That way, if it ever feels like it's becoming too much, you have an option already prepared.

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joloriquelme@reddit

When I saw this post title before entering it, I thought that this CEO treated you like crap. But, it's the same exact opposite. Help him until that help become a problem for you.

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No-Mall1142@reddit

Sounds like somebody who could also help you find your next job as well. Help him out.

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Ron-Swanson-Mustache@reddit

He's abusing your perceived debt to him if he's doing this on your time. You don't owe him anything. I'd talk to him and say "Hey, I like working for you, but this is my time. If you want to use my time then I need to be fairly compensated." Say this in the nicest, must customer service friendly way possible. That said, if he calls you during regular work hours then I'd do it. His name's on the building and he's friends with the other execs. I'd give them all a heads up that it's happening and let them decide if they want to spend company resources on it. I did some work for a CEO after he left a company I worked at. But he paid me for this time and I set up a LLC for it as he was writing what he paid me off. We had a great working relationship. But your time is more valuable to you than it is to the CEO. Treat it as such and fight for it.

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garulousmonkey@reddit

He likely still has a lot of pull in the building and can help your career advance. I recommend helping him - but you can tell him that you have other high priorities for the business and will call him back ASAP. Then make sure you call back by end of day.

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ciaza@reddit

Help him out but peeter it down in a year or so.

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koretex@reddit

I've been in this same scenario.... Continue to help him.

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cat4hurricane@reddit

Is this man hitting you up for problems or information *every* day? Is it just once a week? Once every few weeks? How often is he taking up your time? Is it affecting how much work you complete in a day? If it’s affecting how much work you’re completing in a day, or if he’s hitting you up *every* day with a new issue, then yeah, I might consider ramping down on the contact and use work as an excuse. “I’d love to help you with this issue but I’m currently working on a project that needs to take up most of my time, can I get to you at this hour?” (Or another respectful way to phrase that you’re working on work and can’t really drop everything right now). If he’s only hitting you up when there are issues, but it’s once every few weeks, once a month or something more spread out, and the issues are easy to fix then I would honestly just keep doing it. Having *any* CEO. In your corner is super helpful and you have no idea what kind of people he knows or could hook you up with. He could write you a massive “bonus” at the end of the year for all your help being his personal IT support for all you know, he could hook you up with a guy he knows and suddenly all the house repairs are done or you’ve got a nice new car, totally free to you. Depending on what company he helped run/how successful that company was, you could be unintentionally making bank for yourself if you keep helping him out and he feels like paying it back/paying it forward. Depending on how often he’s got your ear and your time, and how much you like him, it could totally be worth it to sacrifice some of your day/your week to helping him. The windfall later could be life changing because he now sees you as a good guy who helped him when he really needed it.

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arfski@reddit

It's not what you know, it's who you know, and it sounds, retired or not, like a good person to keep knowing.

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noinf0@reddit

I just bite the bullet. I went above and beyond for someone over 20 years ago and they called me out of the blue and gave me a job doing less work, with less users for 30% more pay. A few people that retired I will still help but it is on my schedule. One person got really needy so I would push stuff off, "sorry I am in the middle of a big project and I have appointments. Maybe I can help out next Wednesday." Some of these retired people don't stay retired and their networks can be really big. Helping someone with their iPad is a small price to pay for a successful C level executive reference and contacts if you are ever looking in the future.

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drnick5@reddit

It seems like you have at least some emotional attachment to the old CEO, nothing wrong with that at all, but you need to realize you don't owe this guy anything. He hired you for a job. You did the job, He paid you for the job, end of transaction. You have 3 options. 1. is to do nothing and remain at this guy's beck and call forever. 2. Tell him you're willing to provide tech support, but it's billable, and then quote him a rate. 3. Tell him you're no longer able to provide tech support. If possible, provide him with a name and number of someone you know who can.

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maj0rdisappointment@reddit

Keep that bridge and relationship. Could be invaluable some day when and if you need to make a job move.

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DukeChadvonCisberg@reddit

As others have said, help him out. Nothing bad can come of it but a ton of new prospects and good can. It’s not unreasonable to establish some boundaries but continue to help him out if he needs it.

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bhambrewer@reddit

You have a friendly relationship with a rich retired dude. How you set out boundaries depends on what's more important for you. Is the friendly relationship more important, is the chance of a financial bonus more important, is your down time more important? This is a boundary only you can decide on. If it helps you decide, here's an anecdote. I was once asked to help with a tech issue on a Saturday by someone where if I said no, there would have been absolutely zero repercussions. I had nothing to do, so I said yes, met his lovely wife, and had a nice Saturday with a lovely couple. They asked what they could pay me, I said I'd happily do it for a dinner. We waited for his dad to return from a retirement vacation. His dad had just retired as head chef at a very famous curry restaurant. I still cherish the memories of that event over 20 years later.

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music3k@reddit

Have him bring it by during work hours. If your company doesnt care, you get paid to help. If they do care, they cut him off for you

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soulless_ape@reddit

I think it's a no brainer here, he did good by you so many times I think whatever help he might need in the future is a small price to pay if not just out of loyalty towards the guy. This doesn't mean you can't have some boundaries regarding when you can stop by to help.

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EndsWithJusSayin@reddit

Help him out. Maybe go out for a lunch with him every couple of weeks and ask if he needs any help with his stuff. This’ll save you some time getting paged every week and you get to have lunch with a friend who took care of you and yours.

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Road-Ranger8839@reddit

He has done a ton of advancement on your behalf. Now he is retired and asks that you help with his tech. That's a very fair trade. Although nothing is guaranteed, he will still have contacts with his former company. What makes you think that your quid pro quo is over? He is still your main juice at the company and you should keep working with him come what may. Have faith in the relationship.

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CozyCoco99@reddit

You don’t. He was good to you and now it’s your turn. One would think you’d do this willingly.

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Due-Cup1115@reddit

I think you need to keep returning his generosity with some of your own. Maybe you could try to control the cadence a little by offering to come by his house once a month and help him with any tech questions he has. But honestly, it sounds like you owe him a lot of your success. Just be happy to have had those opportunities.

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bwong00@reddit

Why would you not help him out? One of these days, you're going to need a favor and he's going to be in a position to help you out. And even if he doesn't, you're being a good human, and that in itself is noble.

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Representative_Ad587@reddit

You are slime for this lil bro. Help unc out after he took care of you. Ungrateful ah

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wkearney99@reddit

Want to get ahead? Make friends with those in higher positions, including those retired. Work the network. Too many people fail to appreciate the value in doing so. Is there a possibility of coming up with an upgrade or other longer-term plan for him? Propose something like that, turn it into a side work project that pays. If not, well, doing some free support work and keeping a retired CEO as a friend definitely seems like a good networking move.

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captainsniz@reddit

Don’t burn this bridge. Keep this guy close. He still has leverage and a major ability to shape your future.

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naim_not_name@reddit

From experience, at that level, even after retirement “no” is “I’m sorry sir we fixed it.” So I’m looking forward to the prevailing answer.

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ATL_we_ready@reddit

He’s probably a board member.

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errorx86@reddit

exactly what i was thinking! burning a bridge like that, especially with how kind the CEO has been, is SUCH a stupid idea. OP should just do the monotonous tech support occasionally. yeah it's annoying i completely get that lol but it will definitely benefit them in the long run(and it already clearly has benefitted them up until this point)

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Winter-Buffalo@reddit

I love helping people out that have helped me, but I get the impression that you are starting to feel uncomfortable with his after hours/off the clock expectations. Not sure if saying “Of course I can help out” is the right thing to do in this situation. Drawing a healthy boundary between work and home is extremely important and occasionally difficult.

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Acebladewing@reddit

Help him out, man. A rich retired CEO is a great guy to have as a buddy.

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AnjinToronaga@reddit

Politely, if I was working for a CEO like that and he retired I would just him up. I think many of us myself included forget from time to time how many people would trade with us in a heartbeat. And especially in 2025 how lucky we are to have jobs that pay so well. This doesn’t seem outrageous, just helping a good fucking connection who did the same for you.z

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awetsasquatch@reddit

I'd probably do it without much question if the guy gave me all that

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genxer@reddit

Having someone in your corner when things go sideways is worth the headache.

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jfoust2@reddit

He paid you for your past work. He can pay you for the future work.

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HybridTheory2000@reddit

"Hey guys, how do I say "no" to Tony Stark?"

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sircruxr@reddit

You could fake your death also if you don’t want to help anymore.

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Straight-Ad-4332@reddit

You are a really selfish person. Help the man that helped you.

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LegalWrights@reddit

I mean it depends on how often this is happening. Every day? We gotta shut this down. Every week? More manageable but still frustrating. Any less frequent than that just bite the bullet. If this guy was nothing but good to you for this long, he will probably stay good to you. Be good to people who are good to you.

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JumpTheCreek@reddit

If I got a bonus of five figures even once from my boss, I’d be eternally grateful. He’s done a lot for you and sounds like he’d continue to do a lot for you if he needed. I’d help him out for the rest of my life.

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Smackmybitchup007@reddit

Would it kill you to help him a little? Just be a good person.

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Plasmamuffins@reddit

Absolutely help him, you want someone like him in your pocket. If you shit on him, he will shit on you 100x over.

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WizardsOfXanthus@reddit

You're honestly in a dream position for many. I would not burn that bridge.

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leaflock7@reddit

why would you want to no keep contact with that person which he sounds to be a very solid man. He asks for help, go to his house and have a coffee with him , chit chat. Your conversations will be much more relaxed now. Plus he may be willing to pay you for the time you spend on his tasks

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Flat_Program8887@reddit

You never know when your paths will cross in the future... It's not like your position in the company is set in stone.

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vinnsy9@reddit

mate , just help...its nothing compared to how much that business from this guy has helped you. i had 2 examples in from my past that actually paid... trust me i didn't even think of commercializing or gaining any thing by providing help. (we're not talking for side business that's a different thing). the first one was a VP at this large corporate i was working. He was a difficult boss for most of them (usually demanding) but to me , he was just the person in-charge and i was very fast forwarding with him in a couple solutions which fitted his needs. (we'd call help desk and asked to be transferred to me, or ring my work phone directly without going through the help-desk).. he left the company a year later. had some issue with the tablets and pcs of the kids , so i told him to pack everything and met. i did my usual IT staff, upgrades /updates, antiviruses, parental-control on phones and so on. next thing i know, he brings in , 8 other companies to fuel my side business. ended up doing more money working on my own than working for that corporate. the second , was in another country completely , i moved for work. this guy was the retired CEO.(which i didn't even know at the time). i helped him with whatever his problem was with a floating license for an app we used. he requested a business card and time after time would ping me via email. again , i just provided the help he needed mostly whitelisting his IP, when he was travelling and the password expired, he remained a member of the board so nothing out of the ordinary ..fast forward to the request for having a salary increase and more responsibilities, i receive an e-mail with a big thank you note, an adjustment on the salary in retrospective of 6-months and a bonus. the very same guy has been the voice of that to both CEO and CTO (my direct manager)... useless to say that i never though for a second to monetize my help or to say no to any of them, i didn't even expect any of the returns both of them game.. one might say its just karma....i don't know... maybe it is. hope my examples help you do the right thing...

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trev2234@reddit

Doesn’t sound like a bridge I’d want burned. If it’s occasional then I’d readily help him. If nothing else he might be able to offer free advice on climbing the greasy pole, if that’s something you’d be interested in. If not, he has life experience you don’t have, and when you chat, you could absorb some of it. See this as an opportunity.

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JRmacgyver@reddit

This.... He can "pay" with knowledge, even without knowing it 😉 Some advice is worth it's length in gold.

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Pusibule@reddit

I don't think closing that line is wise. But start digging it more to see if is doing it in nice terms and friendly or is just self-interest. Ask him to give you his opinion on something personal of yours that he has no say to directly intervene (no career advices too soon, no how to earn more money, no personal business or ideas etc) but that has his knowledge and make him feel wise, something like "I'm thinking to buy a nicer house, can you give some guidance on how to negotiate a good deal?" Or something like that. casual and that can't feel like you're expecting him to move strings for you. And build some relation over family/sports/hobbies smalltalk. Over time, if you're interested, drop that maybe you need to progress on your career and don't insist on it. If he is not just doing it for self interest, and see you as someone worthly of his attention, you will see with those things if he reciprocates with interest on those interactions. If not, politely make youself more inavailable over time.

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Salty_Move_4387@reddit

I have been in the same situation before. Like everyone else here is saying, you really should do it. Also, don't be afraid to ask for career advise while doing so. I have not seen it said yet, but from time to time feel free to say "I'm in the middle of a problem/issue/project here, can I call you in the morning/tomorrow/later tonight" as it better fits your schedule. It shows that you are willing to help, but also allows you to do it more on your schedule.

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surpremebeing@reddit

I would support him. Just consider it part of your current job.

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bdunk17@reddit

It sounds like the tech support is probably just the pretext, not the real reason he’s calling. For someone who built a company from the ground up, retirement can leave a big hole, and reaching out to someone he trusts may be his way of staying connected and relevant. If you’re not feeling resentful yet, helping occasionally can be a small kindness that likely means more to him than the actual fix. That said, you can still gently shape the dynamic over time, keeping calls short, steering him toward Apple support for repeat issues, or turning some of those interactions into a quick check-in or coffee instead of ongoing troubleshooting. You don’t owe him unlimited access, but it’s okay to recognize that this is more about human connection than IT, and respond in a way that protects your time without shutting the door on a relationship you clearly value.

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I_HEART_MICROSOFT@reddit

You help him out. Besides it’s good to help others, it won’t go unnoticed and he will likely still be called on at times by the new leadership. I would 100% maintain that relationship.

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FSMonToast@reddit

Theres a lot of comments saying to bite the bullet and do it. But I feel like there's a lack of consideration for something you mentioned, setting boundaries. It is absolutely OK to have and set boundaries. If you feel comfortable helping this awesome guy who had your back, cool. But you are also a human with a life. So feel free to figure out your boundaries and abide by them. Only answer his calls during certain times. And when you do, tell him an actual time you can come over. Stick to that time range. Things like that.

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Content-Program411@reddit

transactional twat you being.

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BlueHatBrit@reddit

Be good to those who are good to you. Sounds like the guy has more than earned some informal tech support given the bonuses, raises, and career he's helped you with. Also seems like he's still got a lot of sway with the company, and is likely a significant shareholder or board member. Helping him out from time to time is probably going to do more for you than most of your normal work. If it's becoming too much, then be kind and have an honest conversation. Explain you're happy to help, but might need a little longer to get to things.

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braliao@reddit

Why would you throw away a good relationship with such an infuncial person!?

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Maltempest@reddit

I'm getting ready to be laid off on Tuesday, wish I had my old CFO boss calling me.. this is what we call networking, and it is invaluable. Good luck.

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mechiah@reddit

Sounds like he thought you had a friendship, mentor/mentee, or patron-type relationship. Do you not provide this little bit of assistance to your friends, mentors, or patrons? If not, shrug, there. My friends in the trades fix my house, my engineer friend corrected plans for me, and you know what, sometimes I help them reset the password on their computer. It's work that's beneath my profession but not beneath my friendships. If you do not see your relationship like that, and you don't think person has influence on your industry and career, then simply stop answering the phone.

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petrichorax@reddit

It's technically crossing a boundary and in most contexts I'd cut them off, but this guy sounds like he's been in your corner a while and yeah I'd say you owe him.

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wezelboy@reddit

If the CEO was a founder, he probably has a large ownership stake in the company, so technically you probably still work for him.

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CommanderSpleen@reddit

The guy is extremely well connected to people who decide over the success of your career and you are thinking about cutting him off from the occasional help?

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hookem1543@reddit

I mean sounds like you should help the guy out. Take care of the people that have taken care of you

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spurscar@reddit

This is so short-sighted.

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josephowens42@reddit

You don’t, he is still well connected, you do it. We still have a ceo from a company we acquired years ago that retired and he still ask for help, this usually comes down from our current ceo and I help. I usually get a nice gift card to a nice restaurant, so that’s nice.

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ThatDanGuy@reddit

Are you helping him during your work hours? Then help him out. Otherwise consider informing him you are willing to do paid support/consulting for him.

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iredditshere@reddit

I always think about opportunities. It probably wouldn't hurt. He could be an ally into your future.

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SpakysAlt@reddit

Sounds like the dude treated you incredible. Just help him out bro wtf

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hitman133295@reddit

I’m happy to be his tech support guy for life if he’s helped me that much all my life. Some of these things don’t take more than 10 mins to help but with his connections, you might get a job or other helps later in life.

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atroxes@reddit

Did he appreciate you *personally*? Did he go out of his way to help you *personally*? If he did, treat him as you would any other friend, because he is. Do you help friend with their IT issues? If so, you help him. If not, you don't. Him being a former employer should not affect your decision.

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surloc_dalnor@reddit

Dude personal relationship aside why would you say no in the short term. He has treated you well in the past and he is still connected. Milk the relationship for all it's worth. Ask him for advice on your career. Go to lunch and get him to dish on internal politics. I'm not saying drop everything when he calls or not to have boundaries, but don't burn the bridge.

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biffbobfred@reddit

Kinda this. Make it to where you get some out of it too.

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phuzzz@reddit

Bite the bullet, but I'd also say make sure to set the boundry of "Hey, I'm cool to keep helping you. But just remember if something is on fire, I'll need to prioritize that. Want to make sure the business you built up keeps running."

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Whatdafuqisgoingon@reddit

This is the kind of guy I would like to know for the rest of his life. I'd consider him a friend now that he's not my boss and I do just about anything for my friends

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BryanP1968@reddit

That’s a bridge you don’t burn. You suck it up and help him. It’s a goodwill investment.

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texan01@reddit

I've done side work for former CEO of companies I've worked for, it's good to keep them in your pocket for the future. You get a good education in how your company is run, from a candid source, a good mentor in future endeavors, and possibly a new friend.

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lordfly911@reddit

Say your services are no longer free and that you will be charging from this point forward.

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phatcat09@reddit

Sounds like you guys are friends.

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Koshqel@reddit

Lmao dude you are throwing away a CEO connection over easy stuff yout family has you do? If the dude was a PoS it would have been a diffrent story. Job security in this era is almost nom existant

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wlpaul4@reddit

I hear you man. We have a have a few retired partners who still avail themselves of our support services. Can definitely be frustrating at times, but I can also appreciate that it’s at least in part because they trust us not to screw them. I will say though: if it requires me to actually spend time after work or on the weekends, I do charge them.

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InigoMontoya1985@reddit

Tell him that you won't do tech support for non-employees... but you will for a friend. -- Legolas.

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largos7289@reddit

to me after hearing that... it's the least you could f\*!@k'n do. Hell i haven't got treated that well at places and was expected to be tech support for life. I mean shit.... he's done right by you and you want to say f\*\*k you? that's cold. Plus if he's as ingrained as you say he is and you fuck him... you won't be there long if that's a better incentive for you.

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lappyx86@reddit

Does he still own the company? If yes, then you do whatever he asks within some sane limits. If not, then its your call.

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PoliteLunatic@reddit

This can't be a serious post OP?

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HefDog@reddit

Kudos to you for recognizing what someone has done for you. Most people can’t see past the one time they didn’t see eye-to-eye. I’m in my employees corner, behind the scenes, a dozen times a week that they don’t know about. Yet the negatives are the only thing most see. You sound like a great person and a great friend. You both are lucky to know each other.

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jkw118@reddit

So id mention it to your boss.. he was the ceo, but he may still hold a different title /ownership... He likely just stepped aside to let others take over and keep his baby going.. But either way id expect the company to say keep helping and charge the company..

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BootleggerBill@reddit

I have been in the same situation for years, except it is our past (2) CIOs. At some point, you have to decide if the person is friend that you want to help out, of if the relationship was purely business and you no longer want or need them in your corner. For me, I have decided it's friendship and it never hurts to have a few well known C suite folks in your circle in case you ever need a job reference etc. I will tell you that in my experience, the frequency of the phone calls fade with time - I still get them, but it's not every week like it was immediately after separation.

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Past-Ad-9995@reddit

Does he pay you for this help? Someone so successful understands what he's asking and what is right and expected. Even if you felt like refusing the money, it should be offered. Otherwise, I do something like this for someone that owns many businesses and helped pull me up from the ground. I'm happy to help. He also pays me. I just do it at a very reduced rate to keep it all fair and balanced.

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how33dy@reddit

Man, it would be dumb to cut him off. Consider this the "networking" part that people like to talk about.

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flxguy1@reddit

I managed an IT department for a large, family owned business for a few years. When one of the C level owners retired, he continued to call into the Service Desk for support for much of the same that you describe. I didn’t know how bad it was until the SD manager let me know that he was being asked to dispatch a field tech to setup a new WiFi router in his home and asked me how to proceed. I explained that he is still an owner, on the board of directors and all of his equipment (iPhone, iPad, etc) that he uses are corporate assets that we still manage and that service must be provided as if he is still working. We ended up creating a “[COMPANY NAME] Retirees” group in AD and our ITSM platform so we can manage the assets and tickets associated with this group since other family members will continue to retire. I was able to run reports against the group to demonstrate the administrative burden, but never had to use it.

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kissmygame17@reddit

Is this a serious inquiry? 5 figure checks to fix some miniscule issues he's having, you owe this dude a good part of what's going well in your life, just do it. That's someone you want as a personal friend

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6Saint6Cyber6@reddit

Absolutely help him. If it’s constant or in the middle of the day, you could set up a standing call/appointment with him weekly to help him with whatever he needs.

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jbp216@reddit

just treat it like a colleague, hes retired but still has massive pull in the company, and to some extent still works out there, people in that position dont just stop when they retire. sounds like a great guy to have on your side

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0zer0space0@reddit

By your description, that is the kind of person I would totally give free personal tech support to. Sounds like he doesn’t ask for much. He helped you a lot, so now you have an opportunity to repay it. I call it “putting coin in the karma bank.” If you hit a brick wall in your career at some point, he would be a good person to have on your side, because he sounds like the type that would put you in front of his network to help you get a new job quickly if you ever lost yours.

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justplainjon@reddit

I've known a lot of C-suite execs in various states of "retirement". It's hard to unplug when you've been at that level, ESPECIALLY as a founder. I have a suspicion his requests will become less frequent as he finds his new path in life. But, yeah, help a brother out until that happens ;)

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Chair_luger@reddit

Help him out but let your manager know that you are spending time helping out the old CEO. They will likely be OK with that. As a founder of the company he may be retired but he still likely owns a good part of the company and is on the board of directors.

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shoeboxfoto@reddit

Sounds like an opportunity. Go to him and say I’ve noticed you have some needs that might be met with a regular service. Do you prefer working with me because of our established relationship or would you call a service that specializes in executive management IT support? Maybe you and he start a business together supporting all his high power CEO and Board member network connections? “See a need, fill a need!” -Bigweld

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HoboGir@reddit

Sounds like a solid guy TBH, I've kept some folks in my back pocket mainly due to the connections they have with others and it's helped me out. He may turn around and start paying you too for the help, but Christmas bonus alone I would be sold to helping him out any time. I get a $25 gift card to a grocery store I don't even shop at.

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Esk__@reddit

Change your mindset from “the retired CEO” to my friend who needs help. They likely think this of you or wouldn’t be calling. Then one day when you need help, your friend will be there for you.

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Aahaanali@reddit

i mean once a weak ain’t that bad for what he’s done and could potentially do for you

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RevLoveJoy@reddit

I'm with (almost) everyone else. This guy went to bat for you, repeatedly. Time for you to step up. It *may be* that he's just having trouble getting everything setup at home the way he wants? Ask if that's the case and if so, perhaps you can just schedule an afternoon (on company time, might as well try, right?) to get his home tech stack all the way he likes?

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NeedleworkerNo4900@reddit

I just want to reiterate what everyone here is saying. Do not abandon this guy. In fact, you should be doing everything you can to foster this relationship. Trust me, this is good for your career and if you’re smart, it will benefit you in the end. Also remember, he’s recently retired and probably working on hobbies now with other important well off people. NETWORK. Offer to help in other areas. Meet these people. You’ll thank yourself in 10 years.

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TravellingBeard@reddit

He wants to be your friend, there is no downside unless his requests are impacting your work or social life. But, as with any friends, there's always "Hey, I can't do that now, but would X time be better?"

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Pure-Recover70@reddit

2 months is not enough time - he's probably still half-running the company - or at least fielding tons of questions from the new CEO - it took me the better part of 7 years to stop being asked questions about a previous position I held (internal company transfer to a very different job). Give it at least a year, probably two. He'll likely also settle down and the amount of support required should in theory also go down. You simply do not want to get on his bad side, and he can still very much save your bacon (or get you fired / not promoted / overlooked for a bonus).

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che-che-chester@reddit

I’d probably just suck it up and continue helping him, considering the circumstances. I was in a similar situation once where the person had gotten me my job, but they weren’t actually above me on the ladder. They had this crazy network in their house that I barely understood, so it was a pain to troubleshoot. I eventually had to cut them off. It was awkward and I think I did hurt their feelings. I hate to be so transactional, but there was nothing they could do for me (or against me).

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ReceptionFun9821@reddit

Count to 3 and answer every call like it's a personal call from Santa Clause and Elvis. As others have said, he's not really retired yet. He has a lot of clout in the business. He also is now in a better position within the industry. As others have said, he's likely to be on other boards. This is a dude you really want in your corner. He's also in a position to be a mentor. I'd be hitching my wagon to that mule all day long.

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winmace@reddit

I'd be helpful during work hours and make sure it's appropriatley logged on the ticketing system, so any time spent on it is easily accounted for

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Mrhiddenlotus@reddit

Give him a while then ghost

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Olleye@reddit

He’s asking you, bc he trusts you, and maybe no one else; so, help this man.

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CounterStrike17@reddit

help him lol

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Bulls729@reddit

My opinion, if he founded the company and his name is on the building, he didn’t ’just retire.’ He has deep roots there and is very likely still invested in the operation with high level stakeholders. This wasn’t some random mid-level manager of yours. Especially if he was the one that personally advocated for multiple high level raises and approvals, he likely still has a backend say in providing more of those potentially. Who’s to say he doesn’t start another business and brings you into an even higher pay bracket. This is one of those unique situations where you should pay it forward, as it will very likely still come around, and even if it doesn’t it sounds like everything he did the least you could do is give him some occasional help, who knows he may even throw you a couple bucks at some point.

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IFear_NoMan@reddit

This dude is out of his mind. We tech nerds have to support stupid people for free, but you literally just give back to the person that helped you, and he can help you in the future too. I'll be happy to help someone like that for the rest of my life.

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edgrant1992@reddit

He might be lonely having just retired, maybe see if he wants to do something as friends, either way it sounds he did you well so personally I'd want to keep helping him out unless the requests become unreasonable.

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zachrtw@reddit

Sounds like your old boss is now your friend, and that's awesome. Had the same thing happen to me and I don't regret it at all. If he's like my old boss he's keeping score and will make it up to you. In my case out of the blue he asked if I'd like to stay in his "cabin" for a week or 2 out in Colorado. It was a cabin in the sense that it was made from logs, but was bigger and nicer than any house I've ever lived in. Except for 2020 we've stayed there ever year for a decade.

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JUSTsMoE@reddit

Strange post tbh.

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gnipz@reddit

That’s a rare CEO. Just time to be thankful and help sometimes. I bet it’ll lessen as time goes on.

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koshrf@reddit

One of my best friend used to be my boss when I started my career, I worked for him directly for 5-6 years, and he helped me when I most needed. 22 years have passed and I still help him on any tech related issue he has and we are not even in the same country anymore. Be kind, be helpful and more than anything, be grateful.

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10leej@reddit

As long as he's not calling you to help him with a personal device while your at work. I see no problem helping him if that's what you want to do. Now if he's calling you for help while you are at work. That a different matter entirely. You didn't exchange your time for his money. You exchanged it for the company's money that he happened to be CEO of. There's a difference and he should know it.

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drMonkeyBalls@reddit

Help him on company time. Make sure your manager knows.

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Guannito-Barrio@reddit

Just think of him as another relative who asks you for tech support during Thanksgiving dinner. You can't avoid that.

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tzigon@reddit

A) Talk to your manager about it. See what they think. B) Offer the former CEO a support contract for your time since you are supposed to be supporting his company and he is not an active member now. C) Be slow to respond to him during work hours and even slower off hours

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Orangesteel@reddit

Two explanations for the same answer: 1) Ethically, pay back some of the good he has done you. Not without limits, but kindness often finds its way back to us 2) Professionally, helping people in positions of influence is often, not always, useful. Build a good name with people and they help to promote you moving forward. The perception of you is often more important than the work you actually do. (I had a fairly terribly tech working for me, customers adored him. We kept him on, because he generated business for us).

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RCG73@reddit

Is it on the clock time? If so put it in a ticket and let your boss worry about it.

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faraboot@reddit

Don't do this.

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gordonv@reddit

Correct. You own your relationship with the ex CEO, not your boss.

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locomuerto@reddit

If I were in your situation I'd definitely help him out. But it would be best to be proactive with boundaries: "I'm swamped with X project for the next 2 weeks, here's a third party provider I trust that can help you with support during that time." Also do your best to help him during your normal working hours and track the time spent helping him.

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amensista@reddit

Yes you help him..... forever. I'm sure its irritating and it falls into that whole category of family asking for free help and setting boundaries at work about people and personal/home IT - which is correct. THIS, this is a special case where damn right you help him. Now if he wants his whole house wiring with ethernet or you to fly out somewhere for a week - I mean that's a different deal but he wants to call once a week for 30? mins whatever then you help him. Because also each thing you help him, maybe he remembers and learns and calls you less. The only time I would even consider mentioning anything would be if he has friends or family members call you about stuff. You were lucky you had a good guy like that in your corner. I have always had extreme loyalty to people who gave me a job. And clearly he thinks highly of you and your post demonstrates intelligence, professionalism and emotional intelligence. My boss is into track racing and asked me to drive a 3 hour round trip so he could take his track car to a mechanic in a different city and me drive him back. NO PROBLEM at all. I was glad to do something for him on a personal level. And I would do it again.

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EverythingsBroken82@reddit

So, as a practical help: he helped you, so you help him, BUT: track what and how much you are helping and also track what you would miss out otherwise. write up your \_feelings\_ about everything. review it every month for at least half a year. if he needs help with his printer for 3 hours and he lives next door once a year: do it. if he needs you every other weekend while you should spend time with your kids: perhaps not so much. you need to understand, what he needs long term and what you need longterm. and once it's clear to you, that it is too much, try gradually to set some small boundaries. perhaps he's just oblivious. if you tell him "the last 3 times i helped you, i could not see my kids", he might say "oh wow sorry, i am so sorry" very likely

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hotspotpreferences@reddit

Why is this even a question!?!!

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ApprehensiveGold2773@reddit

I think it can only benefit you to keep helping him, he still has influence in the company. Don't be afraid of asking him for help if there is something he could do for you!

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DariusWolfe@reddit

If you're friends that complicates things a bit, but if he was just a good CEO, then what you owe him had already been paid. It was a business relationship, he gave you money and opportunities, you gave him solid work. You owe him nothing more. That said, there's middle grounds to everything. You can set some boundaries and still be there for him from time to time, and especially because you're providing free services, you get to set the conditions. Add some basic user training in there for routine tasks, so he can resolve them for himself. Point him to solid self-help resources ("this is what I use for situations like this") and if it's a larger project, all to be paid. This is what you do for a living, it's not a hobby. If he's as good a CEO as you say, he'll know that your time has value and won't resent it. If he's actually the sort of person who will bitch to your employer if you don't keep providing free tech support, fortify that first. Express your concerns to your supervisor before you start pulling back.

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Mindestiny@reddit

This is a question that's entirely up to you. It's a "you scratch my back" situation far more than it's a "defined work boundaries" situation. Do you want this guy to maybe give you an in at a new company down the road? Then answer his random iPad questions here and there. Do you not care? Then blow him off, but the potential for opportunity almost certainly goes with it.

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Serious-Speech2883@reddit

Yeah I would think your biggest mistake would be to stop helping him. Don’t ever bite the hand that fed you.

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StAnkie_Brews@reddit

This is a little tough for the obvious reasons that you state, and you speak highly of him which paints a picture that he might not necessarily be expecting this work from you. Without knowing the guy I am going to say this: Not negative/ not necessarily positive: 1. It's what he's used as being the former CEO. 2. He knows your competent and that the issue will get fixed. Maybe negative (but could just be an outsider's jaded perspective): 1. It's what he's used as being the former CEO. 2. He thinks you owe him for the aforementioned items you detailed. I would say that if it's during work hours and interfering with your actual job, but you don't actually have a problem doing it, then I would redirect to a time that works better for you and explain that your personal time being used for professional abilities isn't free and set up a payment for service *if* you wish to continue with that type of agreement. If you wish not to continue, be as gracious as possible, "Sir. I know you were used to having this as a perk of your former position, but politely speaking, this is outside of my company duties and I can no longer spend company funds for these issues, here is a reliable resource (insert tech support company) that can fulfill your needs." You also might be able to go the route of approaching one of the other higher ups and asking if it's within your duties to see to the former CEO's needs and have them nip it if you think that's an option. If it's your personal time, then restructure the statement above to model that your very thankful for the leadership he gave, but your personal time is just that that you'll need compensation if you want to continue or if you don't, you set the boundary and provide a resource so their not left hanging. That's just my thoughts, I'm sure someone will have better insight or perhaps a modification to my thought that amplifies it's message.

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AwakenedSin@reddit

This CEO is a great ass contact to have in your network and all you have to do is occasional tech support. Which I am guessing you're doing on the clock. I hope you are at least! I'd keep doing it if I we're in your shoes. Plus other people said in the comments though he's retired. CEOs are never "retired" lmaoo. They still have contacts in the company and more than likely still has influence.

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TireFryer426@reddit

A friend of mine was in a very similar situation. Long story short, he's the CTO of the guy's next business venture. You can absolutely have boundaries. Just let him know that you might not be able to help immediately but you will get back to him. He may organically find someone else that can help him 'now'.

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Creative-Type9411@reddit

i would bite the bullet for that one some people have to bite the bullet every single day 9 to 5... This guy gave you a good 9 to 5. So you should show love as much as possible try to automate anything and show him how to correct any recurring issues himself It's worth it, past tense

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doughnut_cat@reddit

help him dude what the hell is wrong with you.

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Fritzo2162@reddit

I'm in this situation with a couple of former clients. They're older and I think they call me on occasion because they don't know anyone else that can help them. I still help them when they call and catch up. If I ever want out of the situation, I'll find them someone else to help them out.

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iam8up@reddit

Why in the world wouldn't you help the guy out with things? That sounds like someone to have on your side of the table!

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Outrageous-Guess1350@reddit

Just make him pay market rate. Don’t get taken advantage of. Let him decide if it’s worth it.

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CoolDragon@reddit

![gif](giphy|fXnRObM8Q0RkOmR5nf)

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PaleMaleAndStale@reddit

Personally, I would help him as much as I reasonably could. He may have retired, but as a senior executive, with presumably a long career behind him, he will have a lot of valuable contacts and influence, not just in your current organisation but further afield. Having him as an ally, reference and mentor could benefit you massively for years to come if you maintain a good relationship with him. Seems like giving him a bit of tech support is a small price to pay and it may well be that he enjoys your company as much as your technical skills.

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chewubie@reddit

I don't see it as any different than when my friends ask me for tech help.

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nikade87@reddit

Still helping our old CEO who once gave me a chance and is a big reason I'm doing well with my career. What goes around comes around, even tho he left about 7 years ago.

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valg_2019_fan@reddit

Do it on company time 😜

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Aim_Fire_Ready@reddit

Sounds to me like it's time to pay the pied piper.

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Upper-Affect5971@reddit

Don’t burn that bridge, bad idea. Dude, we still handle the tech support of a widow to our old CEO because her son sits on the board. She is technically not covered, but it would cause way too much drama if we told her to kick rocks. Besides, she gives up fancy bottles of wine when we help her out.

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No_Feels_yo@reddit

Take out "literally" then I'll give ya my advice!

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Korazair@reddit

Is he calling you while you are at work or at home. If at work, just mention it to your boss “hey boss, CEO called me to fix his iPad connection seems he never really got the hang of them.” And see what your boss says, company pays you for your hours at work, if they want to spend them in the retired person, that is not your problem. If he is calling after hours at home then it is your choice to deal with it as you see fit. He did a lot for you so giving him a hand isn’t a huge ask.

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Asleep_Spray274@reddit

Imagine having a CEO/president of a company as a contact. If you ever need advice or guidance from someone who you could probably call up sometime, thats invaluable. And all you have to do is fix his ipad now and again. Its not the bigs things that get you ahead in life, its the combination of all the small things. Try to see the long game of maintaining that relationship

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QuestConsequential@reddit

If you are on the clock, that shouldn't be a problem for a while.

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ThisIsMyITAccount901@reddit

Sometimes if you take a long time to reply and let them know how busy work has been they go away on their own.

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nelly2929@reddit

Just do it during work hours and all is good ...... Find a way to help him remotely (lots of options to do that for 95% of his "issues")

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chis2k@reddit

Your second paragraph says it all. This person has been very good to you as a gatekeeper at this job for financial reasons. He appreciated your work and rewarded you. People like that don't come around as often as you would like. There's always excuses especially when it comes to money. Take care of the good people in your life with your gift. And I say gift because it is. We are like plumbers or electricians...people who you need to get important things done quickly and correctly. It's a gift we have and can reward those who have done good for us or add positively to our lives. Consider yourself lucky and pay it forward once in a while.

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AustinGroovy@reddit

It may be worth asking yourself why you feel the need to say 'no'. I personally know the work involved in being the friends/family tech support after hours, weekends, holidays. Like others, I say help him out when you can. Sometimes you come across unusual problems - where solving that problem gives you knowledge that can help at work.

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WinterFamiliar9199@reddit

I had a similar situation with a friend of the family. One day she needed help and I was out of town so I told her I was gone but if she wants help I’ll call my buddy who can come right away. Sent a guy I knew was solid and they’ve cut me out of the loop entirely. Yeah! Maybe you can find a lower lvl employee that is worth while and tell the ex-ceo you’d like to get him some experience working with important people like him.

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Ecrofirt@reddit

Here's my take on it. When I was much younger I was in a help desk role at a college. As a natural extension being good at my job, I ended up doing a lot of side work for faculty and staff. As time went on and rlny role, and personal life changed, I made the decision to stop taking on "clients". I'd direct people to whoever was in my former role and wish them well. But, nearly 20 years later I still help out the retired secretary of the former president. Do I need to? Absolutely not. But she's a nice person, she trusts me, and taking a little bit of time out of my life to help an elderly lady doesn't cause a huge issue in my life. It sounds like this person helped you. If it were me, I'd help back. If he's a good person, he'll understand that you're able to help as your schedule allows and he'll be ok with that.

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igooazoo@reddit

You don't have to. But it would probably be a smart thing to stay on his good side.

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braytag@reddit

How much was those raises? You can spend 1 hour a week to help the guy out, make a friend.

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Masam10@reddit

If he helped you out that much and is just asking for odd favours like can you help me find this email, I’d be helping him in return free of charge. But if it’s “can you help setup a few computers for my son’s side business” etc then I’d be offering mates rates and charging.

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CalmPilot101@reddit

On the practical side of things -- Is it likely that the number of requests comes from the fact that he just started a new phase of his life? Lots of things to fix when you don't have work email anymore etc. Anyhow, sounds like you are on good terms, and in this situation you could look at each other as maybe not friends, but acquaintances? In which case the favors you do for him opens the door for you asking him for favors when you need one? If you look at it that way, keeping in contact through helping him with stuff could be seen as a good thing.

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flexibu@reddit

Don’t be ungrateful dude

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SteiniMinni@reddit

So I would suggest you donut like with the other execs, you mentioned you did some side work with them. Make sure you get paid for your work, either by billing him directly (if you feel like it do it with a family and friends bonus) or inform your current boss about it and do it on company time. But under no circumstances help hin for free on the regular.

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QuailAndWasabi@reddit

If you do it on work time i dont see anything wrong with it, given that those things fall under your job description normally and your boss approves of you putting time into doing these things for him. Then it's just normal work. So 2 scenarios. **This happens during business hours** Explain you need to treat this as any other case, put it into the system to clock the time, sometimes you need to prioritize other things. Explain this is so you can continue doing an awesome job. He will understand it in those terms since he's been the CEO (hopefully). **This happens on your free time** Trickier, but seems to imply either he sees you as a friend or as an underling he can fuck around with. If he sees you as a friend, then treat him as another friend (within reason lol). You can perhaps make a joke that "you'll have to start billing him soon if this continues" and then laugh a bit about it. Hopefully he picks up the hint, otherwise continue this for a while with similar jokes or small jabs. If it does not help you'll have to be more frank and tell him you are more than willing to help, but during business hours and if the company approves. If he however sees you as just an underling, then you need to take a more proffessional approuch and ask him to do this during business hours, again if the company approves. Ofc when you turn him down you can say that you really appreciates everything he's done for you and stuff like that, but the current situation cannot continue. Just do it gently and it'll be fine if he's not an asshole, which it actually does not sound like he is from your post.

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ansiz@reddit

IMHO you are probably better off taking care of these requests. Especially if they are at reasonable periods of the day and don't take all that long. Odds are this guy is still in touch with a lot of people and him being an ally of yours could really pay off. Who knows, he might get bored and unretire, start a different business or get brought in as a board member/advisor for a different company, that could open new doors for you as well. It's also possible this guy actually likes you, is somewhat bored lonely and is contacting you just as much for connection than actually help, but he doesn't know how to do that socially. Maybe he just really needs the help though, but if he's not an ass then I would just keep helping him. I used to have the same problem with doctors wanting me to do IT work for them outside of my hospital IT role, but generally that was a clearer business only relationship.

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Saaquin@reddit

Just remember that you can also help him without dropping everything and attending to his issue with a sense of panic. I think as long as you’re calm and get to it on your own time, what is the harm?

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EmperorGeek@reddit

Bite the bullet and provide him the service he deserves. It’s the least you can do. He did it for you. And I bet he didn’t have to ask Strangers on Reddit if it was the right thing to do.

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roffelmao@reddit

I'm in a similar situation. Our President Emeritus (started the organization and ran it for 28 years) still comes to me with issues. It's almost always something trivial, but even if it wasn't, it's the price of doing business for me. Most other people could kick rocks though - I made the mistake of helping out coworkers with personal IT stuff at the start of my career and that took a long time to unwind. She understands if she doesn't hear back immediately, so at least she doesn't feel entitled about it. That probably makes a lot of the difference.

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Ekly_Special@reddit

Networking, and having someone at his level owe you one, is incredibly valuable. Not to mention his influence at work is probably just as strong and valuable as before he retired. Continue building that relationship. See if your manager is cool with doing during work hours and putting in tickets for it so you have metrics.

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22OpDmtBRdOiM@reddit

can you just do it during paid time?

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Hungry_Research1986@reddit

A large part of getting ahead is connections. As long as you aren't being taken advantage of, I would help out and keep contact.

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Bksudbjdua@reddit

Is he lonely? Id do it.

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rubbishfoo@reddit

Help those who help you is my opinion. Sounds like a lot of your success originates with this guy. I wouldn't toss that out.

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Disgruntled_Smitty@reddit

You're kind of screwed here lol. Best you can do is be unreliable and take a long time on response and such.

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whatdoido8383@reddit

Sounds like the last you can do is a little tech support for him now an then... Now, if he's calling you at 2AM and on the weekends, that's a different story.

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Krigen89@reddit

"Hey man, I'll be glad to, but I'm on this project right now... Let me open up a ticket and I'll get back to you". Let your boss worry about wether the ticket should be handled or not.

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MrHappy4Life@reddit

I’ve had this happen and I just keep telling them that I have other work right now, but will get back to you when I can. Get back an hour or so later, and keep doing that. Eventually they will stop going to you when they need it done sooner.

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-Satsujinn-@reddit

Sounds like he went to bat for you, I'd say he's earned a little help. All those things you listed - would you give them all back to not have to deal with this? I doubt it. Normally I'd be very much "Fuck 'em, professional and personal are different things", but when it's a small company and the owner looks out for you, it' s a little different. Obviously boundaries are important. Don't go cancelling dinner plans or missing kids recitals, but if you need to spend an hour or so here and there, so be it. I found myself in almost exactly the same situation. It tapered off eventually.

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Greed_Sucks@reddit

I wouldn’t change a thing. Small price to pay. He knows it, you know it. Just accept your fate.

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MetalMayhem1@reddit

Does he have your personal number? I would personally separate personal life and work. I would respond slowly and not be available to him all the time. Keep work at work mentality. I'd be worried to say no if i'm still working there just incase, that's my personal opinion. Once you leave though it's a different story.

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aaiceman@reddit

Are you doing the help during normal work hours and with your boss's approval? If so, then you're good to keep going. But also, don't respond to anything outside of business hours. Also, no home visits. If he has an issue, he can bring his stuff into the office. His employment status doesn't matter to you, but keeping to your work hours/boundaries does matter to you. On a personal note, if you feel this isn't a bridge you want to burn (keep everyone happy, can open future job prospects), then keeping things upbeat and grey rocking on responses outside of business hours is a strong option to go with.

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BreadAvailable@reddit

This.

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UltraSPARC@reddit

If you don’t want to be a dick, why don’t you send him off politely. I would find a local break/fix or other small MSP that would be willing to take up a single person. He probably has a really nice house so there could be opportunities there for them. Then present it to your former CEO. “Hey man! I hope you’re enjoying your retirement. Must be nice to have a lot of down time to relax. Things have really picked up at the office and you know how life is with kids, but I don’t want to leave you high and dry! So I’ve found this local business who can help you going forward. *hands over whatever marketing materials they have* Let me know when you have them scheduled to come out so I can properly off board you to them so you’re in good hands!”

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vitaroignolo@reddit

This has become a personal matter that could become professional if not handled correctly. On paper, professionally, you owe this guy nothing. That of course doesn't mean he couldn't become vindictive and professionally burn you. If you feel what his foundations have given you warrants ongoing personal IT support, that's noble and your call. I hate providing personal tech support myself. But professionally, this might be a question for the HR subreddit first and your company's HR second. They are better equipped to handle professional matters that become personal.

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evantom34@reddit

Spend time on the clock to help him- and cite it

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Pretend-Newspaper-86@reddit

i even do tech support for the parents of my boss because he doesnt want to during my work time

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mixduptransistor@reddit

Well, I would first talk to my immediate manager. Even if you're the Director or VP of IT, whoever is the next rung up even if it's the new CEO, ask their advice. I assume you were helping the previous CEO on company time? If so, just make it clear that your family life is busy and you are happy to help him, but before it was part of your job. If the new CEO and company leadership don't expect you to do it on company time, you unfortunately don't have time for a second job and must decline the extra work. Or, at the very least, tell him you're going to have to come to an arrangement on payment since it's not on company time anymore Maybe give him some lead time to find someone else instead of cutting off cold turkey since he's been good to you? But, as good as he was to you, you also provided work to him and the company for that benefit. He does not own you, you provided your labor for the pay you received previously. Do not let him guilt you into giving free labor forever. Doesn't mean you have to be an asshole about it, but don't let yourself be abused

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CaptainZhon@reddit

If they are paying you; you can’t say no.

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BionicSecurityEngr@reddit

Hard boundary to enforce. While he may not be active in the company, he has deep connections to the people still there. Tread lightly. Try it introduce him to a young up and comer aka redirect him to a new resource.

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aaron416@reddit

Definitely set some boundaries. He’ll keep using you for tech support as long as you help, so it’s time to say no.

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