Accepted into Ycombinator. From my prospective, if you believe in yourself and the business enough then you should be able to make considerable more (as your example of Heroku). The other reality is that 5 million isn't a lot of cash, assuming that is pre-taxed. While you could live a modest life with that amount of money, could you face yourself in the mirror at 75-80 and say, "I give it my best shot" versus "I never tried and don't know if...". I couldn't live with the doubt or unknown of what could have been.