It depends on the company, your timing, and what terms you agree to (number of options, vesting period, ISO vs. Non-qual). If you're actually interested in doin

It depends on the company, your timing, and what terms you agree to (number of options, vesting period, ISO vs. Non-qual). If you're actually interested in doing well, you may need multiple startups, and the earlier the stage, the better. I know multiple people, including myself to some degree, who have done well as employees in startups. And of course, you could always try to start your own -- multiple times as needed.