0) VCs with technical/operating background. I'd put a lot of faith in e.g. pmarca's evaluation of a team. 1) EIRs 2) Outside advisors 3) Portfolio companies (you do some pre-screening, then have your existing portfolio CEOs meet with the founders of non-competitive new ventures. It's win/win, because the portfolio companies may have some useful business relationship, or if the founders can't raise, might be a good hire.

They pick advisors who know how to do what they already know how to do, to validate their decisions. That leads to some improvement in the process, but they're not picking people who complement their skill sets. They're picking less shiny versions of themselves.

I've seen the quality of people who get EIR roles. They're not slouches, but I could do better than most of them, and that includes the ones at top firms. I can actually detect things like what kind of programmers your tech stack will attract; non-technical executives are better with general-purpose marketing, but the 10X factor with regard to programming talent is black-magic to them.

Even rarer than 10X programmers are people with enough experience and insight to know what brings "10X" into being and what smothers it. It's not just about the people; conditions and configuration play a gigantic role.

I've avoided exploring the VC route (as in, becoming one) because I want to keep my technical skills intact. Also, I'd be +5 sigma great at one part of it (evaluating technical choices and judging talent) but I have no idea if I'd be any good at the other (also critical) aspects of the business. I also feel like if I committed full-time to nontechnical stuff, I'd lose that +5 sigma edge. Right now, I know that if you're using Clojure and your competition is setting up the Java/Maven/IDE environment, you'll almost certainly win. I might not be able to pick that sort of thing out, in 20 years, if I step away from using technology on a day-to-day basis.

Right now, I could grep a codebase and tell you better than almost anyone out there if a company has the technical mettle it needs. ("Visitor" or "AbstractFactory" = bad, "mapcat" or "flatMap" = good.) I wouldn't have that if I sat out of the technical game for 20 years, because the signs and terms would be different.

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.

Three of my friends were EIRs, and two are now founders of great companies (although not hardcore tech companies). The other has run off to Spain for a while, after ~15 years of doing startups, for something of a sabbatical. They're all at the "code for days straight", graduated from top engineering programs (in contexts like being in India or ~20 years ago where that mattered, unlike the US today), etc.

The whole point of EIR is that it's revolving door -- you do it for a year or two, then go back to startups. It's both a way to take a break, and get exposed to new stuff. You still use some of your tech skills, and often end up working on side projects, so I don't think a year off is going to kill your technical competence.

As for the quality of portfolio company review/advice: one top one sent me to do an interview/etc. with probably the best operating executive in the security industry, one of their portfolio companies. I learned a lot, and decided we should hold off on raising as a result (this was ~2 years ago, about a month after I finished YC).

Being an actual full-time VC probably does hurt your technical skills, and I don't think having just fairly narrow programming or programming tech skills is a useful background for a VC, although "ability to pick winning teams" is essentially the definition of a successful accelerator or seed stage investor (but, on more axes than just "can program well"). Something a bit broader and maybe less deep is good, although in cleantech having postdoc level expertise might make sense. I think I have more than enough security industry experience to be an effective security vc, but not enough in the programming tools space, and somewhere in the middle on deployment/automation/networking tools.

I've talked to VC Principals/Venture Partners who are what I'd consider top-50 domain experts in specific things (payment regulations), and some Partners who are top-500 on networking or certain parts of security.

The other thing is it's usually better to have domain expertise in the founding team than implementation perfection, so at seed, a PHP hacked together piece of crap that works is probably fine, as long as what they're doing 1) has a market 2) is possible. At Series A, they should probably have some competence in the team, and after, sure.

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.

"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).