91/91k/135 question.. (trying to see how I can legally be paid to fly someone else’s plane)

Posted by Flying-Guy-6699@reddit | flying | View on Reddit | 9 comments

Long story short, I know a gentleman who owns a very nice plane, he is a pilot and so far it’s only been for his personal use. He found me to help him get his commercial license and in that I jokingly mentioned him making his plane for commercial use and me being a full time pilot for him. This brings up all the fun questions because he’s also down for it but we want to stay LEGAL!!! Also he isn’t really trying to make profit he just wants the plane to pay for itself if any way possible

  1. What is the easiest, safest (in terms of legality) and cheapest way to go about this. The owner of the aircraft knows a lot of people would like to pay to have me fly them to their places. But I’m not sure if it would be a 91 opp, 91k, 135, 119.. all of it confuses me after staring at the far aim for hours.

  2. If someone can confirm, isn’t it technically legal if his plane is under an llc and I am solely a contract pilot not advertising myself. Or does that mean I can only fly people related to his llc?

  3. If he hypothetically wanted to go all in and try and start a small 135 operation, how hard is that, how expensive even is it to get all that stuff set up legally, and is this the smartest (again in terms of legality) way to go about this.

I’m sure I’ll think of more questions but I know there’s a lot of folks on here that know a lot more about this than I do. And I always struggled on this aspect of training when I went for my commercial. I am a full time cfi and have been for 2 years now so obviously I see this as a potential gold mine but again I want us to stay legal. Any help is much appreciated.