The puffed-up companies that went public during the Bubble didn't do it just because they were pulled into it by unscrupulous investment bankers. Most were pushed just as hard from the other side by VCs who'd invested at high valuations, leaving an IPO as the only way out. The only people dumber were retail investors. So it was literally IPO or bust. Or rather, IPO then bust, or just bust.
Add up all the evidence of VCs' behavior, and the resulting personality is not attractive. In fact, it's the classic villain: alternately cowardly, greedy, sneaky, and overbearing.
I used to take it for granted that VCs were like this. Complaining that VCs were jerks used to seem as naive to me as complaining that users didn't read the reference manual. Of course VCs were jerks. How could it be otherwise?
But I realize now that they're not intrinsically jerks. VCs are like car salesmen or bureaucrats: the nature of their work turns them into jerks.
I've met a few VCs I like. Mike Moritz seems a good guy. He even has a sense of humor, which is almost unheard of among VCs. From what I've read about John Doerr, he sounds like a good guy too, almost a hacker. But they work for the very best VC funds. And my theory explains why they'd tend to be different: just as the very most popular kids don't have to persecute nerds, the very best VCs don't have to act like VCs. They get the pick of all the best deals. So they don't have to be so paranoid and sneaky, and they can choose those rare companies, like Google, that will actually benefit from the giant sums they're compelled to invest.
VCs often complain that in their business there's too much money chasing too few deals. Few realize that this also describes a flaw in the way funding works at the level of individual firms.
Perhaps this was the sort of strategic insight I was supposed to come up with as a "technologist in residence." If so, the good news is that they're getting it for free. The bad news is it means that if you're not one of the very top funds, you're condemned to be the bad guys.
[1] After Greylock booted founder Philip Greenspun out of ArsDigita, he wrote a hilarious but also very informative essay about it.
[2] Since most VCs aren't tech guys, the technology side of their due diligence tends to be like a body cavity search by someone with a faulty knowledge of human anatomy. After a while we were quite sore from VCs attempting to probe our nonexistent database orifice.
No, we don't use Oracle. We just store the data in files. Our secret is to use an OS that doesn't lose our data. Which OS? FreeBSD. Why do you use that instead of Windows NT? Because it's better and it doesn't cost anything. What, you're using a freeware OS?
How many times that conversation was repeated. Then when we got to Yahoo, we found they used FreeBSD and stored their data in files too.
Undergraduation
(Parts of this essay began as replies to students who wrote to me with questions.)
Recently I've had several emails from computer science undergrads asking what to do in college. I might not be the best source of advice, because I was a philosophy major in college. But I took so many CS classes that most CS majors thought I was one. I was certainly a hacker, at least.
What should you do in college to become a good hacker? There are two main things you can do: become very good at programming, and learn a lot about specific, cool problems. These turn out to be equivalent, because each drives you to do the other.
The way to be good at programming is to work (a) a lot (b) on hard problems. And the way to make yourself work on hard problems is to work on some very engaging project.
Odds are this project won't be a class assignment. My friend Robert learned a lot by writing network software when he was an undergrad. One of his projects was to connect Harvard to the Arpanet; it had been one of the original nodes, but by 1984 the connection had died. [1] Not only was this work not for a class, but because he spent all his time on it and neglected his studies, he was kicked out of school for a year. [2] It all evened out in the end, and now he's a professor at MIT. But you'll probably be happier if you don't go to that extreme; it caused him a lot of worry at the time.
Another way to be good at programming is to find other people who are good at it, and learn what they know. Programmers tend to sort themselves into tribes according to the type of work they do and the tools they use, and some tribes are smarter than others. Look around you and see what the smart people seem to be working on; there's usually a reason.
Some of the smartest people around you are professors. So one way to find interesting work is to volunteer as a research assistant. Professors are especially interested in people who can solve tedious system-administration type problems for them, so that is a way to get a foot in the door. What they fear are flakes and resume padders. It's all too common for an assistant to result in a net increase in work. So you have to make it clear you'll mean a net decrease.
Don't be put off if they say no. Rejection is almost always less personal than the rejectee imagines. Just move on to the next. (This applies to dating too.)
Beware, because although most professors are smart, not all of them work on interesting stuff. Professors have to publish novel results to advance their careers, but there is more competition in more interesting areas of research. So what less ambitious professors do is turn out a series of papers whose conclusions are novel because no one else cares about them. You're better off avoiding these.
I never worked as a research assistant, so I feel a bit dishonest recommending that route. I learned to program by writing stuff of my own, particularly by trying to reverse-engineer Winograd's SHRDLU. I was as obsessed with that program as a mother with a new baby.
Whatever the disadvantages of working by yourself, the advantage is that the project is all your own. You never have to compromise or ask anyone's permission, and if you have a new idea you can just sit down and start implementing it.
In your own projects you don't have to worry about novelty (as professors do) or profitability (as businesses do). All that matters is how hard the project is technically, and that has no correlation to the nature of the application. "Serious" applications like databases are often trivial and dull technically (if you ever suffer from insomnia, try reading the technical literature about databases) while "frivolous" applications like games are often very sophisticated. I'm sure there are game companies out there working on products with more intellectual content than the research at the bottom nine tenths of university CS departments.
If I were in college now I'd probably work on graphics: a network game, for example, or a tool for 3D animation. When I was an undergrad there weren't enough cycles around to make graphics interesting, but it's hard to imagine anything more fun to work on now.
When I was in college, a lot of the professors believed (or at least wished) that computer science was a branch of math. This idea was strongest at Harvard, where there wasn't even a CS major till the 1980s; till then one had to major in applied math. But it was nearly as bad at Cornell. When I told the fearsome Professor Conway that I was interested in AI (a hot topic then), he told me I should major in math. I'm still not sure whether he thought AI required math, or whether he thought AI was nonsense and that majoring in something rigorous would cure me of such stupid ambitions.