"Failure is simply the opportunity to begin again, this time more intelligently." ~Henry Ford
One of the reasons Henry Ford was willing to risk so much to start an automobile company is because Thomas Edison, who Henry idolized, encouraged him to do so. Edison told Henry something along the lines of "Do it Henry. If I was a young man I think I would start an automobile company."
I think companies like Y Combinator are serving much the same purpose, helping encouraging people to go after their dreams. Most will fail, but they have probably learned a lot more than they would have in a cube, about both software and business. Those that succeed, well, hopefully they will pass the encouragement on. I wonder who Henry Ford encouraged?