I've spent most of my adult life in failed startups in some form or another. Some were funded, most were bootstrapped. Probably 6-8 man-years if I subtract my dances with full-time employment (I'm doing contract work now and working on another startup on the side with a partner).

I have no regrets. I've asked myself a couple of times if it was worth it, and to be honest I can't think of anything else I would have rather been doing at the time. It's not like playing slot machines, hoping someday to hit the jackpot. It's more like an obscure artist trying to find his niche—you do it because this is who you are.

If I never have a big success, I'll die satisfied knowing I was doing what I felt I should be doing. I read a quote from a post on this list some years ago, I wish I could remember the source. But it was something like, "When I look back on my career, I want to say, 'Boy, that was a fun ride!' not 'Boy, I sure felt safe!'"