I live in New York. Most people expect perfect career histories, even in startups. Even minor blemishes put you out forever. It's that competitive.
When I was at Google, I put together a strategy that would have saved Google+ Games (there was a G+ Games, you ask? My point exactly) and no one took it seriously because my previous startup (at which I was an engineer, not CEO) had failed. Had that startup become a success, people would have taken the suggestion seriously and Google would be worth at least tens of millions more.
I'm 29 and already deal with age discrimination and the "job hopper" stigma from having made a couple bad calls and having a story that looks more like freelancing than the "company man" fantasy (which is dead, and people who still believe in it and hold "job hopping" against people should be evaluated for dementia).
I also get an unbelievable amount of shit about leaving Google and, on a job interview, you can't exactly say, "Oh, their reputation as a great place to work is completely fraudulent because in 2009 they hired a bunch of transplant execs who turned the company into Enron, and now it's impossible to move to a better project." It's the truth, but I can't say it.
Maybe it's magically different in the Valley. I don't live there; I don't know.