That you have four close friends who have made significant windfalls is a bit of an anomaly. There are far more people that have lost on that gamble(trading salary for options) than there are that have won. Give it another ten years of working at startups and it won't look so crazy.

I'm mot even sure how you "optimize for gaining a "life changing amount of money"? That's like saying you are going to optimize for luck. There a substantial amount of luck involved in seriously "cashing out" on a startup.