Money, stability and all other factors aside. What do you really want to do? Personally, I'd forget about flying and continue growing this business. But that's coming from someone who flew at Colgan for 3 years and resigned as a Captain. I feel like I made it far enough in aviation to "smash the bug." From my perspective, beyond the larger equipment and the initial enjoyment of working in the 121 environment, you can get most of your aviation fix from smaller aircraft. I'm completely happy as a stay at home dad right now (beyond the paycheck), but I wonder if I would be if I had never gone down the 121 path? If you have a burning desire to fly for the airlines you can always give it a try, and if it doesn't work out head back to your business. At 23 you still have lots of time to change your mind.

Another option would be to continue your business, maybe part time, and work an aviation job on the side. Colgan used to be an option for that when there was primarily outstation basing but that probably wouldn't work now. Otherwise I'm sure there are jobs locally flying 135 or corporate.

Since this thread is about what I would do, as someone that's been down the 121 path both as a pilot and the son of a pilot, I'd turn my back and never look back. If you have the drive and ambition to run a profitable business at 23 you're never going to be happy in a senority based system. You won't made 50,000 for years, and your personal life will suffer in numerous other intangible ways. Keep up with the business, I bet you'll be making a 100,000 by 30. I'd also like to hear more about this business, it sounds like a great way to make money.