Working at 5 startups with 4 year vesting periods and a 20% success rate (which seems high) means ~12-16 years of taking a pay cut before you get your first win

Working at 5 startups with 4 year vesting periods and a 20% success rate (which seems high) means ~12-16 years of taking a pay cut before you get your first win. And don't forget the compound interest you'd be getting from investing that $20k/year (or $10-$15k after taxes) in a diversified investment like the stock market. Basically, if you want to take stock, approach the decision like an investor or VC with that level of skepticism and thought. Otherwise you're just throwing darts.