Paul Graham, proto-techbro.

What a 2004 Paul Graham essay tells us about how the culture of Silicon Valley has changed.

Allow me just a moment to point-and-laugh at billionaire technologist Paul Graham.

In case you are unfamiliar, Graham is the founder of YCombinator. He has had an outsized impact on the culture of Silicon Valley. He once tweeted “Any industry that still has unions has potential energy that could be released by startups.” So, yeah, we sort of have a collective moral obligation to heckle the guy.)

The year before he launched YCombinator (back when he was just a tech millionaire, not a tech billionaire), Graham fancied himself quite the essayist. He published a book of essays, Hackers & Painters. WIRED published the first essay, “Why Nerds are Unpopular,” in the December 2004 issue. The subhead of the piece reads: “If you're too cool for school, you're probably not very smart. Some of us would rather build rockets than friendships.”

Spoiler alert: Graham never built rockets. Maybe the real rockets were the friendships he made along the way?

Graham’s entire thesis is that nerds are unpopular in junior high because “they have other things to think about. […] They want to be smart.” That’s it. That’s the whole argument. Just a grown-ass man caterwauling, “WELL I COULD HAVE BEEN POPULAR IF I WANTED TO BE!!!”

This, upon inspection, is not particularly persuasive. It hinges on the idea that nerds have other things on their minds, while non-nerds lack complex inner lives. At one point he tries out the analogy that nerds chasing popularity are “like someone trying to play soccer while balancing a glass of water on his head. Other players who can focus their whole attention on the game beat them effortlessly.”

(The glass of water is, uh, being smart? This is not a good analogy, if you think about it. But maybe it could be a popular analogy if you don’t think about?)

That’s all a… fine?… thing for a nerdy 17-year-old to tell himself. But it’s very much the sort of thing you are meant to grow out of. Those other kids were also balancing metaphorical glasses of water on their heads, I assure you. Being a teenager is hard.

But Paul Graham is 40 years old when he writes this essay. He has already made millions in Silicon Valley, and successfully weathered the dotcom crash. And he’s still fixated on the fact that, back in high school, he didn’t get to sit at the cool kids table (Literally. The opening anecdote in the piece is a story about the high school cafeteria seating arrangements).

I swear… some fellas will write a whole book of essays instead of going to therapy.

(I doubt I’m breaking any news here in revealing that I also was deeply unpopular as a child. I trust that you, as a reader, had that one figured out.)

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I find Graham’s 2004 essay interesting because of what’s absent from the piece. Graham’ is depicting Silicon Valley as the land of misfit losers, the ultimate triumph of the A/V club. There are no techbros in his rendering. The hustle-culture types who chase wealth and fame by launching serial startups, high on charisma and low on subject-matter expertise, didn’t yet exist. This is an essay from back before techbros were a thing.

And that raises what I consider to be a more interesting historical question: when did the cultural archtype of the techbro emerge?

I know it was before 2014. That was when the HBO show Silicon Valley premiered. Techbros had been part of tech culture for long enough at that point that Mike Judge could satirize them, confident that a mass audience would get the joke.

I know the archtype doesn’t exist in the ‘70s, ‘80s, or ‘90s. If you watch a show like Halt and Catch Fire, you won’t catch a whiff of them. (Side note: Halt and Catch Fire is brilliant and you should watch it.) Or you could read the books and magazines from back then. Mondo 2000 was deep counterculture. So was Burning Man, in its early years. The Mondo readership wasn’t the stereotypically popular crowd.

Here’s my working hypothesis: I think the culture of Silicon Valley was heavily impacted by two migration waves from the financial industry. The first migration wave was during the 90s dotcom boom. Between late 1995 and 2000, a ton of money flooded into the tech sector. Finance-types chased that cash, acquired social and institutional power, and set down roots in Silicon Valley.

Paulina Borsook writes about this phenomenon in her 2000 book CyberSelfish. She also discusses it in this Salon.com interview:

…One of the very recent changes [circa 2000] has been that the übergeek libertarian culture I wrote about has been mated with MBA culture, which brings its own prejudices and religious beliefs to the party.

That's an interesting melding: the masters-of-the-universe MBA culture colliding with awkward geek, "I don't have the world's best social skills" culture. But they love each other's rhetoric and ideology and there's a strange sort of symbiosis going on. Geeks and MBAs intrigue each other for complementary reasons: MBAs like being associated with the geek shibboleths of inventiveness and revolution; Geeks are attracted to the MBAs' promise of making things real through the glamour of money. And both of them like money because it's something that can be counted.

So now, when we talk about high-tech culture, a lot of what we're talking about is really business-speculation culture, and a transplanted Midtown Manhattan advertising culture, or Wall Street financial culture. So, though we may use the words "high tech" these days to refer to this group, they're not all the same kind of person -- but they are finding lots of common ground. (emphasis added)

So tech culture begins to change in the late 90s, when the advertising execs and Wall Street types arrive. That starts at the level of VCs and CEOs. The average tech worker is still someone who majored in computer science before it was cool. Many of those tech workers spent a year or two as paper-millionaires, but get wiped out by the dotcom crash. In the early ‘00s, we don’t quite have “techbros” yet.

The second financial migration wave occurs after the 2008 global financial crisis. That’s when working in tech becomes the standard destination for people whose rough trajectory in life is (1) try to become prom king, (2) party hard in college, (3) get into business school, (4) make a lot of money doing whatever makes you a lot of money these days.

Now I don’t have this cultural inflection point nailed down solidly yet. It clearly happened, and I think it’s worth reflecting on. But I don’t know for sure that it starts post-2008. That’s still a hunch.

But, bringing this back to Paul Graham: what stands out to me is that tech is absolutely the destination of choice for the high-achieving popular kids today. His essay was clunky and cringe in 2004. In 2024, it’s also fascinatingly dated.

And that, at least in part, is because of Graham’s own actions and influence. The tech culture that Graham helped to seed is also a culture that doesn’t particularly value smart anymore. The way you get into YCombinator is by displaying charisma and charm — by showing that you have the same tastes and sensibilities as the other founders. And getting into YC grants you access to a network of powerful figures, financiers, and companies that will lift you up and eventually arrange for a nice liquidity event.

YCombinator, in other words, is the ultimate popularity contest.

I wonder if Paul Graham ever picked up on the irony.