"Pay your dues", perhaps, but competent person -> funded (or employee at funded company, or just someone known for doing something awesome) -> EIR, could be 2-4 years.
VCs are probably less stupid about credentials than e.g. Google under Mayer with the "core schools" crap. Maybe less stupid than "core schools" in admittance. I suspect being a Thiel fellowship person, a core developer on a really popular open source project (nginx dude for sure, probably Ver if he wanted to do something in bitcoin on his own, etc.) would be more than adequate. Or YC/500 Startups/etc.
You basically have to play degenerate political games to get investor contact as an employee of a funded startup. It really is a two-class world these days.
My experience is based on what I've seen in New York, but everything I've heard about the Valley is that it's the same. Well-connected douches will always have a competitive advantage over real people. We get our shot when tech becomes uncool/nerdy again and those assholes go back to whatever douche Valhalla they return to.
I've seen other companies with a variety of weirdly dysfunctional ways of treating employees, but what's the Tolstoy quote? "Happy families are all alike; every unhappy family is unhappy in its own way." If you have a decent network in Silicon Valley, and/or are willing/able to bounce once a situation seems bad, it's pretty easy to stay in "Happy families" only.
I don't think Silicon Valley vs. New York has a lot to do with it.
The problem is that when you run into bad people and they ruin your career or steal your future, then good people don't want anything to do with you (or, at least, have you at arms' length, and that gets annoying) so you get a string of more bad people (who are always happy to take advantage of your weakened position).
I actually think that a bit of so-called "depressive realism" is in order. Sure, it needs to be tempered with some optimism, but you need at least one guy with the winter-traveler insight and the courage to say, "Groupon for cat food sounds like a terrible idea!" Sadly, people like us are not well-received because we tend to haul out the truth when it's not wanted.
But yes, a less-bitter version of you might be a good EIR, although I think it usually comes from "founder of a company funded by the firm has a midsize exit", not out of the blue.
So you have to be born into the club to have that option? Not surprising.
Like I said, the future's not going to come from the people born into VC connections. I don't know where it's going to start and when, but I'm optimistic enough to believe that Real Technology is coming back. I see it already, but not in the high cost-of-living areas.