Where Fun Goes to Die
What startups can learn from the University of Chicago
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Tech comms could take a page out of the University of Chicago’s book.
Here’s a list of ways people have described the school:
Where fun goes to die
The level of hell that Dante forgot
Where the only thing that goes down on you is your GPA
“If I wanted an A, I would’ve gone to Harvard.”
UChicago embraces it. You can find these taglines on T-shirts worn proudly by students or whispered with alternating horror and glee on forums like College Confidential. Fifteen or so years ago, when I was looking at schools, the tour guide spoke gushingly of these slogans (well, except for number three; we were with our parents, after all) as a reason to choose the school over its ivy-walled peers.
As other colleges cater to students’ unending desire for grade inflation, as they avoid poking any fun at themselves whatsoever, as they gut academic departments in favor of ever more luxurious amenities, turning college into something closer to a retirement community or a residential cruise line than the kind of experience through which individual intelligence or civic ethos might be forged (steps off soapbox), UChicago has taken a different approach. It remains defiantly nerdy in its branding.1
UChicago’s brand strategy works because it signals that the school stands for something, and it tells you what that something is: a rigorous education. Its entire culture is built around that full-throated geekiness, which in turn allows people who aren’t the right fit to opt out — which then, in turn, further entrenches its culture, and so on and so forth.
This is not so much intentional positioning — something decided upon by Deans of Such-and-Such in an ivory tower — nor an algorithmically driven attempt at attention baiting as it is lore, the accumulation of over a century of student mythos into a self-propagating declaration of character.
Stand for Something
There’s a lesson for startups here. Founders right now are competing for a small subset of talent, especially AI talent. You have to give people a reason to choose you over every other company out there, even if the core value proposition is (let’s be honest) more or less the same.
Because top colleges do, indeed, offer fundamentally the same product: an excellent education, a brilliant peer set, a lovely campus, connections to the élite and powerful. The differences between, say, Harvard and Yale, or Princeton and Dartmouth, are largely at the margins.
If you’re about to protest because you went to one of these schools and it’s, like, so totally different, actually from the others, I’m willing to bet you’re going to make a cultural argument, not a quality one. Harvard is for Masters of the Universe, Yale for B-averse English majors and thespians, Princeton for the preppy popped-collar set, Dartmouth for beer-sodden frat bros. These differences are differences in storytelling — and not just the manufactured storytelling of marketing communications, but the things real humans say aloud.
Similarly, great startups generally offer the same core product, things like visionary leadership, a big ole TAM (and thus market cap, and thus potential financial outcome for talent), and great colleagues. To be clear, founders should still emphasize these things! You need these factors, and great candidates won’t consider you without them, just as the best students won’t consider colleges that aren’t at the top of the US News and World Report.
But these Very Important Factors are also table stakes for great talent. Once candidates have weeded through companies to determine which are worth their time, the actual decision often comes down to culture. What will it actually be like to work at this place day to day? Can I see myself being a part of this in-group? Is this a quest I find valuable? Is this an alumni group I want to be a part of one day?
That reason to choose you is usually right in front of you, organic, the thing employees are already telling their friends. You can find it on Glassdoor or a gossipy thread on Hacker News. It’s the answer to the sentence: “This is the kind of place where ____.” For instance, this week we saw that OpenAI is the kind of place that will blow up product lines and rebuild the entire business around where it sees the strongest financial future. People who join OpenAI can expect to be somewhere with unrelenting change in pursuit of winning.
Stand against Something
One of the clearest ways to show what you’re for is through contrast — that is, to show what you’re against.
Anduril did a brilliant job of this last year with their Don’t Work at Anduril campaign. The tongue-in-cheek spot highlighted the kind of person who wouldn’t succeed at Anduril — someone who wants to work remotely, or fewer hours, or is uncomfortable with an America-first mission — and in so doing perfectly captured who would.
I use this example a lot in my client work, and sometimes a client will have a strongly negative reaction. “We can’t do that!” they exclaim. “That’s so off-putting!”
To which I respond: Yes! Exactly! You want to repel the people who aren’t aligned.
When I was at Palantir, we were very candid with candidates about our work with the US government. This was a correction from a period of overexuberance, circa about 2015-2018, when everyone wanted to work for Palantir because it was cool (at least cool amongst a certain set of Silicon Valley computer science majors) and not because they gave two hoots about the mission. That worked great, right up until it didn’t. The second the public turned on the mission, those same people — the ones who didn’t make any real choice in joining — got real noisy and distracting (and ultimately, once we were clear where we stood, left the company).
Hype, in other words, is a deficit of lore. It is a focus on the fact that something is shiny, not on what it stands for. Your brand should be a magnet; it should repel as well as attract. Your strengths should be the opposite side of the coin of your weaknesses.
I’m sure you can see the parallel to UChicago. If you’ve already vetted people for your most differentiated qualities — whether that’s reading Plato late into the night or working on a product that is used on the battlefield — you don’t have to worry about hype cycles. You don’t have to worry that you’ll lose a whole class of applicants next year, when you move from #8 to #12 in the USNWR rankings. You’ve already found your true believers.
The lesson is to force people to make some kind of choice about what joining your company means.
Additional Reading
It was a great week for narratives about narrative. A few reads that are worth your time:
Venture capitalist and former comms head at Box, Glossier, and Social Capital Ashley Mayer argued that startups need to give people a reason to root for the future.
Beyond your cap table, who wins if you win? It can be your customer in a broad or narrow sense, it can be your customers’ customers, it can be an industry, it can even be an idea or ideal (like privacy or creativity) that your customers care about deeply. When you construct your narrative with someone or something else as the hero, perhaps counterintuitively, your own growth story becomes much more powerful. It’s no longer just impactful for your team and investors; it’s evidence that the world is getting better in some way that lots of people care about (and will root for). And in a moment when the headlines are decidedly doomsday, optimism is what’s contrarian and interesting.
Native Studio founder Jihad Esmail contended that building great companies requires conviction and leadership, and that documentation of such belief is better thought of as articulation (expression of that true core) than “comms” (whatever wins the attention game).
People want to be a patron of a company that believes something specific enough to say it in public, and maybe even to be the kind of leader the ad describes. That hunger is what this essay is about. There is a kind of corporate writing that used to be possible, then disappeared, and whose return is now necessary.
No, I didn’t even go here — if you must know, I went to Princeton — but somewhere in North Carolina, in a musty file folder that sits astride debate trophies and high school French quizzes and, if you can believe it, printed! on paper! report cards, I do have a tripartite pro/con list that includes it and my other two finalists.




Love this and thanks for the shout-out!