I’ve been doing this about 30 years. I would say that as far as outcomes and personal success you are doing much better than most. The real question is whether you enjoy it and have the confidence to leave companies who aren’t a good fit quickly. My guess would be after a few more, you have a big financial outcome if that’s what you are looking for, but only worth it if you are having fun. Otherwise go work for a bigco and enjoy yhe other half of your life

The most important thing to him will be to feel that you respect him. As long as you get that message across, all will be for the best.

The best time to start a startup is today. The second best time is tomorrow. You want to spend your life on the steepest learning curve you can, and there is no steeper learning curve than your first startup. You will be far more valuable and have a better perspective whether you succeed or fail. But if at all possible, succeed, because your life will change significantly - more freedom, more ability to do hard things, better likelihood of staying in a maximum learning environment.