Paul Graham

Paul Graham is someone I would call an enigma. And also a big inspiration to millions. He is a tech genius (he literally started Y Combinator), a phenomenal writer, and a studied painter. What can’t this man do?!

I can see myself taking some inspiration from his blog, which is like a digital time capsule from the Y2K era — minimalist, unapologetic, and kind of iconic. RAQs? What a rebellion against FAQs. Of course Paul Graham would answer the questions no one else thinks to ask. (Rarely Asked Questions, if you were confused).

Cities and Ambition

Cities and Ambition, written in 2008, highlights how various cities prioritize types of ambition. He explores the idea that cities send subtle messages about what you should care about. Those messages, whether through overheard conversations or embedded in daily life, shape what people strive for. At a high level, here are some pairings that are discussed:

• New York -> Make more money.
• Cambridge -> Be smarter.
• Silicon Valley -> Gain power.
• Florence circa 1500s -> Be Leonardo da Vinci.

Arguably, the message that a city sends means a world of difference in how you live your life. For that reason, people who prioritize a certain type of ambition flock to the same cities, even if the weather is dismal and it is way too expensive—just think Cambridge.

An interesting point Paul claimed is that ambitions are incompatible—and therefore each city only focuses on one type of ambition. After trying to find a counterexample, I think this is true (in my experience, but of course I have lived in very few cities yet). When I think of LA, I imagine fame. In SF, highly technical companies are the name of the game. Living in San Diego, relaxation and slow days are what everyone desires. Is that even considered an “ambition”? Only people in San Diego would know… LOL

Favorite excerpts

“A city speaks to you mostly by accident — in things you see through windows, in conversations you overhear. It’s not something you have to seek out, but something you can’t turn off.”

“Some people know at 16 what sort of work they’re going to do, but in most ambitious kids, ambition seems to precede anything specific to be ambitious about.”

“Does anyone who wants to do great work have to live in a great city? No; all great cities inspire some sort of ambition, but they aren’t the only places that do. For some kinds of work, all you need is a handful of talented colleagues.”

– Paul Graham, Cities and Ambition

How its changed

Funny enough, Graham said that San Francisco’s message “seems to be the same as Berkeley’s: you should live better. But this will change if enough startups choose SF over the Valley.” He is basically saying that SF was a crunchy alternative to the Valley. And, apparently, creating a startup in SF was considered a “self-indulgent choice,” which is still true—SF is darn expensive. But I think that the shift already happened in the past 5 years—even YC, his own startup incubator, quietly moved its HQ to SF in 2023. So don’t worry Paul Graham, your dream of startup asceticism¹ lives on, it’s just sipping $8 cold brew in SoMa.

Which is funny, because now the narrative seems to be flipping again.

I feel there’s been a recent trend of saying, “SF is not it anymore.”

And yeah, I get it — between the homelessness, car break-ins, and some sketchy late-night vibes, it’s easy to write off the city as broken. But it’s not dead. It’s just evolving in weird, chaotic, very SF ways.

For example, Hacker houses are creating LinkedIn microcultures of builders again. An echo of early Silicon Valley, but with less khaki shorts, more AI agents. There’s a real “build weird stuff, find your tribe” energy going on.

So maybe the city’s message isn’t “live better” but more so “live on the edge… of a new product launch.”

Taking a step back from San Francisco, the entire idea of ambition has seemed to change. I don’t think ambition is just intellectual or money-driven anymore. It’s about your vibe, visibility, and whether your life looks good in a photo dump. You could raise goats OR funds and still be seen as ambitious—just in a different way.

Wondering where SD fits into this

While obviously Paul did not live in San Diego, I do. And I wonder what message this city is trying to send.

From an academia and corporate world perspective, I think SD is highly underrated—simply because no one talks about what is going on. But UCSD and the biotech industry (which literally surrounds my house) are huge, but there’s not much flash. So maybe the message is “Do important work, but don’t make a scene about it”?

SD also has a strong creative community — indie bands like Thee Sacred Souls and designers such as Don Norman, father of design and founder of the Design Lab (showing off a bit here). Here, people quietly put out beautiful work without chasing headlines. So what about “You should create for joy, not for clout?"

Unlike the cities Graham mentioned, SD is absolutely sprawling. So it is possible that the physical distance between communities dilutes our message or creates dozens at once.

In a way, the message becomes more personal. Like the favorite book we throw in our tote bag on the way to La Jolla Shores, or the quiet joy of reliving a weekend from freshman year with the same friends, just a little older now.