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.
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
Also, starting anything, whether it's a business or not, will give you exposure to many of the same ups and downs as a startup. You can get much of the experience with essentially zero risk (except to your ego) by starting a social club, student organization, hobby website, or open-source project. Just as long as you make an honest goal of adoption and don't just put it out there with a "whatever happens, happens" attitude.
My first major programming project was a complete rewrite in college of a Harry Potter fansite that grew from 2000 to 100,000 registered users during my time on staff. Relative to my skill level at the time, it was probably the hardest thing I've ever done, and it taught me a lot about the emotional roller coaster and persevering through the lows where I really want to quit.
You can get much of the experience with
essentially zero risk (except to your ego)
by starting a social club, student
organization, hobby website, or
open-source project.
Unless you are supporting a family, where's the big risk in trying to start up your own business?
It's not like you will be reduced to living under a bridge and panhandling if things don't pan out - if you're a good programmer finding a new job isn't that hard.
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