The general advice is - "Don't force it! It won't get you anywhere." However, I feel, smart ambitious people, can't avoid the anxiety to do their own thing. Leaving a high-paying job on a vital position might not make a lot of sense but I believe, when you are surrounded by people making multi-million dollar enterprises with almost-similar skill-set (maybe, with a better business sense), you can't avoid that feel of not finding a single reason to not to replicate the same level of success.
Starting a company because "everyone else is doing it" sounds like a bad idea. For me, it's been something I've wanted to do since my first side project got 1500 uniques via StumbleUpon, and suddenly I realized how much fun it is creating something new that has real users.
Well, building a billion dollar business requires a different skill set than running a billion dollar business. Often when a business is in transition from "explosive growth" to "organic growth", the guys who got you there are no longer the right fit.
If you're financially secure, why force it to stay in a position you don't enjoy? Besides, having a C-level title from a successful startup makes it a whole lot easier to get funding for the next thing you want to build...
I don't think that looking at people making "multi-million dollar enterprises" is necessarily going to cause much envy or anything. Brockman presumably has equity worth quite a lot and was key to the level of success Stripe has seen so far.
