Hey Kareem, long time! This is an important discussion, and my comments shouldn't be interpreted to mean I don't think joining an early-stage company is risky.

Hey Kareem, long time! This is an important discussion, and my comments shouldn't be interpreted to mean I don't think joining an early-stage company is risky. It is! But it is easy to be too conservative with the OP's logic, and not everyone is ready to be a founder, so I think it's a great spot for people who have some risk tolerance but still want to build learnings and networks, and it has potential to turn out well financially too. And, you get a lot more opportunity to see data before you join, and to leave early, if it's not going anywhere. To answer your question, I have turned down my share startup deals that would have had no stock upside, and accepted a few too. But I've also turned down a number of opportunities that clearly had breakout potential, and in aggregate, if measuring strictly by wealth creation potential, I believe I sub-optimized by not taking more of the startup gigs that were offered to me. (There were other personal reasons for these decisions too, which offset those outcomes.) YMMV!