Startup stock options are good when: - there is no liquidation preference overhang - you feel confident your contributions will significantly move the needle fo

Startup stock options are good when: - there is no liquidation preference overhang - you feel confident your contributions will significantly move the needle for this startup - you're not giving up much in terms of salary - you're ready to take on a bigger role/build up experience A friend of mine managed to get this right 4 times in a row. (joined 4 companies, made solid return on all of his stock options). so it's definitely not impossible. obviously a large ammount of risk involved though.