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.
Argh - I am so glad I don't live in an elitist nyc/valley area where people compete through job cannibalism. My life is simple, my home is cozy and my nights are mine. I write code in a small shop on its 11th year, my 5th. I am so glad that software is not all about life in the fastlane. I admire your life style, but I do not envy it.
The startup where I worked was completely unrelated to the idea that would have saved G+.
I'm saying that, had that startup succeeded and had I ended up at Google around the same time, I would have had the credibility to actually roll up my sleeves, push a few idiots out of the way, and save those tens of millions of dollars. But I didn't have that credibility, at least not then, so I had to sit back and watch as enormous amounts of value were incinerated before my eyes.
Now that I'm 29 and have had 6 jobs, I really don't want to keep changing. I'll gladly bolt if I end up with an awful manager, bait-and-switch hiring, or any of the other nonsense that we put up with in this industry, but there's something to be said for a 5+ year fit. I really don't want another 6-month fling. Any idiot can get "a job"; getting the right one, one that comes with some credibility and autonomy, is important.
It seems that most people, after a startup fails, end up in the shitpile applying for bullshit subordinate roles where they might get to write 5 lines of new code per day in the vain hope that one day, several years later, The Boss might throw them a bone and give them a real project.
Most SV companies I've dealt with seemed not to have their act together. A couple were pretty cool, but one told me to expect 5 phone screens (I bowed out; don't have time for that shit at my age) and one required signing a full-on non-compete to take a coding test! This prima donna shit gets old.
I think there are a few million unemployed Americans who would love to have a word with you.
I believe it is the eve of being well-known that we are all our own spokespersons and that our branding and image is just as much a puff piece as a coke commercial.
I do agree this falls apart when the stories involve other people, at least non-anonymous people. No one likes a snitch.