One good place to apply this principle is in college applications. Most high school students applying to college do it with the usual child's mix of inferiority and self-centeredness: inferiority in that they assume that admissions committees must be all-seeing; self-centeredness in that they assume admissions committees care enough about them to dig down into their application and figure out whether they're good or not. These combine to make applicants passive in applying and hurt when they're rejected. If college applicants realized how quick and impersonal most selection processes are, they'd make more effort to sell themselves, and take the outcome less personally.
The world of investors is a foreign one to most hackers—partly because investors are so unlike hackers, and partly because they tend to operate in secret. I've been dealing with this world for many years, both as a founder and an investor, and I still don't fully understand it.
In this essay I'm going to list some of the more surprising things I've learned about investors. Some I only learned in the past year.
Teaching hackers how to deal with investors is probably the second most important thing we do at Y Combinator. The most important thing for a startup is to make something good. But everyone knows that's important. The dangerous thing about investors is that hackers don't know how little they know about this strange world.
About a year ago I tried to figure out what you'd need to reproduce Silicon Valley. I decided the critical ingredients were rich people and nerds—investors and founders. People are all you need to make technology, and all the other people will move.
If I had to narrow that down, I'd say investors are the limiting factor. Not because they contribute more to the startup, but simply because they're least willing to move. They're rich. They're not going to move to Albuquerque just because there are some smart hackers there they could invest in. Whereas hackers will move to the Bay Area to find investors.
There are several types of investors. The two main categories are angels and VCs: VCs invest other people's money, and angels invest their own.
Though they're less well known, the angel investors are probably the more critical ingredient in creating a silicon valley. Most companies that VCs invest in would never have made it that far if angels hadn't invested first. VCs say between half and three quarters of companies that raise series A rounds have taken some outside investment already. [1]
Angels are willing to fund riskier projects than VCs. They also give valuable advice, because (unlike VCs) many have been startup founders themselves.
Google's story shows the key role angels play. A lot of people know Google raised money from Kleiner and Sequoia. What most don't realize is how late. That VC round was a series B round; the premoney valuation was $75 million. Google was already a successful company at that point. Really, Google was funded with angel money.
It may seem odd that the canonical Silicon Valley startup was funded by angels, but this is not so surprising. Risk is always proportionate to reward. So the most successful startup of all is likely to have seemed an extremely risky bet at first, and that is exactly the kind VCs won't touch.
Where do angel investors come from? From other startups. So startup hubs like Silicon Valley benefit from something like the marketplace effect, but shifted in time: startups are there because startups were there.
If angels are so important, why do we hear more about VCs? Because VCs like publicity. They need to market themselves to the investors who are their "customers"—the endowments and pension funds and rich families whose money they invest—and also to founders who might come to them for funding.
Angels don't need to market themselves to investors because they invest their own money. Nor do they want to market themselves to founders: they don't want random people pestering them with business plans. Actually, neither do VCs. Both angels and VCs get deals almost exclusively through personal introductions. [2]
The reason VCs want a strong brand is not to draw in more business plans over the transom, but so they win deals when competing against other VCs. Whereas angels are rarely in direct competition, because (a) they do fewer deals, (b) they're happy to split them, and (c) they invest at a point where the stream is broader.
Some angels are, or were, hackers. But most VCs are a different type of people: they're dealmakers.
If you're a hacker, here's a thought experiment you can run to understand why there are basically no hacker VCs: How would you like a job where you never got to make anything, but instead spent all your time listening to other people pitch (mostly terrible) projects, deciding whether to fund them, and sitting on their boards if you did? That would not be fun for most hackers. Hackers like to make things. This would be like being an administrator.
Because most VCs are a different species of people from founders, it's hard to know what they're thinking. If you're a hacker, the last time you had to deal with these guys was in high school. Maybe in college you walked past their fraternity on your way to the lab. But don't underestimate them. They're as expert in their world as you are in yours. What they're good at is reading people, and making deals work to their advantage. Think twice before you try to beat them at that.
Because most investors are dealmakers rather than technology people, they generally don't understand what you're doing. I knew as a founder that most VCs didn't get technology. I also knew some made a lot of money. And yet it never occurred to me till recently to put those two ideas together and ask "How can VCs make money by investing in stuff they don't understand?"
The answer is that they're like momentum investors. You can (or could once) make a lot of money by noticing sudden changes in stock prices. When a stock jumps upward, you buy, and when it suddenly drops, you sell. In effect you're insider trading, without knowing what you know. You just know someone knows something, and that's making the stock move.
This is how most venture investors operate. They don't try to look at something and predict whether it will take off. They win by noticing that something is taking off a little sooner than everyone else. That generates almost as good returns as actually being able to pick winners. They may have to pay a little more than they would if they got in at the very beginning, but only a little.
Investors always say what they really care about is the team. Actually what they care most about is your traffic, then what other investors think, then the team. If you don't yet have any traffic, they fall back on number 2, what other investors think. And this, as you can imagine, produces wild oscillations in the "stock price" of a startup. One week everyone wants you, and they're begging not to be cut out of the deal. But all it takes is for one big investor to cool on you, and the next week no one will return your phone calls. We regularly have startups go from hot to cold or cold to hot in a matter of days, and literally nothing has changed.