I definitely agree that entrepreneurs are going to take the plunge or not. I'm focused on the support network / employee angle, and harkening back to daveschappell's point that the circles don't really connect. There are communities, yes, but no sense of overall community that you can get a starting point in. It seemed like tribes all the way down: ex-[Amazon | MS | Google], UW clubs, etc. And if you didn't know where to begin, there wasn't an easy way to find someone to ask.
Case in point: if I'd known there were more startups looking for talent, I probably wouldn't have moved out to the eastern part of the state in 2007. At the time, my options after burnout+dismissal seemed to be 'work for another large company'(which I'm still wary of), 'pursue your own idea on your lonesome'(which I didn't have any of at the time) or 'don't work at all'.
(My best classes at WSU were with Hagemeister, Wang(CS460 FTW), and Biker Bob. Contributing to my slight-insecurity as a dev, I was also part of the Benson class that petitioned to have him removed: for tossing us a description of car/cdr and expecting us to build a complete Lisp in SML)