If you're asking yourself this question and currently work on BigCo, you might consider working for a startup first, as opposed to founding one. In the Bay Area, startups pass their series A round provide comparable salary and benefits to BigCo jobs. You won't get as much equity or exposure to as many of the ups-and-downs, but making the transition from BigCo to a 30 person company is a big jump.<p>I quit my BigCo job 2 weeks before my wedding to join a friend's startup as employee 20-something, quit after 18 months, and then joined my current startup as employee #1. With each move, my risk tolerance increased alongside my confidence that I wouldn't die. It has been almost a 4 year process (and still going), but I feel much more prepared now than I would have been in the summer of 2007