"Would you rather have a $100k steady job, or a 5% chance to make $1m in a year with a startup?" -> Definitely startup, even if the expected utility is half.
Would you pay 50k to join a startup and work for free as a consultant?
What is this, an anchoring exercise? :P Are you asking if I would pay to work in a startup? No, I can start my own for free.
And just so everyone knows what I mean by this, 50k is the opportunity cost of the other job that's being forfeited. This means that the "thrill" of working in a startup must be worth at least 50k.
But part of the thrill would be the possibility of the million.