I guess I don't know what you mean. They were certainly out of the "we don't know if this experiment is going to work or not" stage, and it was clear that the experiment was working. The number of startups that were being funded was less, but the number of startups in general was less too.
That seems like a really odd point to challenge, especially because he set the bar as "not out on the street with glazed-over eyes wondering what could've been." I mean, I kind of regret passing on a Google job in ~2001 to continue with an ultimately-doomed startup. I also regret not spending $10k on AAPL stock back then. I'm still quite happy with my life to date.
If you could get into YC in 2008, you could almost certainly get one of any number of great jobs in the Bay Area, and could easily found a startup again (even with YC; depending on how exactly you left, it might be a positive).
Sure, I don't question the fact that you could make a series of horrible decisions, regret them and then still later on in life be quite happy, despite those earlier failures. That doesn't make the original decision to drop out of YC a good idea. I would think, I might be wrong, you should just make it work and not drop out. You should do whatever it takes to make it work.
And I mean... to paint a little sunshine here, there are also probably plenty of times where we all have made the right decision and it had the best possible outcome in the scenario.
Well, the circumstances are very specific, but - I had a flame out with a cofounder and decided that he was not someone with whom it would be worthwhile to continue the startup. The idea was primarily his, and it was going to be his vision that drove the startup. After the flameout, he's had other startups and jobs that were very much in line with the vision of our original startup. Those startups and jobs failed to demonstrate the correctness of his vision, so I think I did the right thing. It's the equivalent of making a decision to not buy Zynga stock back in the day.
