In San Francisco everyone is building an AI startup.
In New York everyone is complaining about their situationship.
I’ve been travelling for work the past week meeting up with colleagues, investors and friends in San Francisco and New York.
In SF you can’t walk two blocks without hearing someone talk about their Clawbot setup or seeing an ad for autonomous agents. Everyone is building something.
New York has plenty of AI talk too, but the conversations also span geopolitics, financial markets and the difficulty of dating in the city.
One city is obsessed with building the future.
The other is obsessed with navigating the present.
There have been a lot of hot takes about SF and NYC being cooked or becoming irrelevant. With the readership of Serviceable Insights spanning many countries and continents, I thought I would share my own observations from the ground.
These two cities sit at the center of global finance, technology and culture, and spending time in both offers a glimpse of where things are heading.
Keep reading to find out why San Francisco feels like a giant startup workshop, why New Yorkers walk like they’re always late and why a city with millions of people somehow struggles to produce stable relationships.
If this week’s article does not interest you, please check out some other recent ones:
San Francisco is Machine City
Many Europeans and East Coast non-tech people don’t realize that San Francisco and Silicon Valley are different places.
When I told people I was heading to San Francisco, several asked how Silicon Valley was. Silicon Valley is actually about an hour south of the city, centered around Palo Alto and Stanford University. It is a great place for startups and venture capital firms, but from what I hear it is otherwise not the most exciting place to spend time. I would not know. I did not go there.
SF itself is buzzing. People who say San Francisco is cooked hasn’’t been there recently. Sure there are still homeless people and occasional piles of human excrement but not to the extent people will have you believe.
If you think AI is getting a lot of attention online or on television, it is nothing compared to walking around the city. Every co-working space seems full of people building something. For a city of roughly 850,000 people, the concentration of technical talent is extraordinary.
Anyone who has lived there for a few years knows someone who joined a startup early and made life changing money. Building a company doesn’t feel like a pipe dream, just a matter of time until it’s your turn.
This draws people from all over the world. It is common to meet professionals in their thirties sharing apartments with two or three roommates just to make the economics work. Housing is extremely expensive because the city has a severe shortage of supply.
This is completely self inflected because the city is notorious for blocking new developments. In their effort to preserve the historic look and charm of their neighbourhoods, they’ve made it impossible to build.
The irony of SF being one of the most tech advanced cities while also unable to build or change anything is not lost on its residents.
In any case, the charm of the city is very nice for tourists but awful if you’re trying to live there and don’t earn as much as employees of OpenAI or Anthropic. Working at either of these places would likely qualify as being a local celebrity in SF, perhaps on par with a reserve player for the Golden State Warriors.
This is because everywhere you look you see AI agent ads. At every restaurant, you know most discussions are about vibe coding, tech stacks etc. This is not to say there isn’t any culture in SF. They have a great art scene including world class museums, good restaurants, access to outdoor activities and plenty of other cool stuff.
Not everyone who lives in SF works in technology but for the people who are serious about making their startup a success, they probably couldn’t imagine themselves living anywhere else. This is because there’s definitely a premium placed on being an SF based company.
SF and other California based companies raise about as much venture capital as the rest of the States combined. Many investors will ask startup founders to move to the Bay Area if they want a term sheet. It makes sense. You are closer to the biggest VC funds, access to talent and can cross pollinate with other founders and companies.
There was a lot of talk about California losing this edge, due to mismanagement by politicians. Investors like Keith Rabois moved to Miami and expected many others to follow. Some opened offices there or expanded their footprint to New York or elsewhere but there’s so far little evidence that SF is losing its footing as the premier city for early stage technology.
There’s something infectious about the atmosphere. You get inspired just walking around the city, which is super hilly (take it seriously when Google Maps says it will take 20 mins to walk 1KM/0.6Miles). If you’ve never seen photos, the streets don’t look real. They look like something out of an Arthur Cobbs dream from Inception. The closest comparable I can think of is Lisbon, but that’s selling it short.
I’m not sure how much people actually walk around San Francisco. I feel like most people opt for the bus, cable cars or Waymo’s, which you get used to seeing, especially around Union Square (where Salesforce tower is).
On the plane everybody had their laptops out working. Most coding. Some doing it without the help of coding agent. This is because status in SF is determined by how well known your startup is or which investor backed your latest round.
Meanwhile in New York, it’s which social club you belong to, even if it’s a run club.
New York is Still The Empire State
Getting into the city was difficult. With Mandani’s mandatory call to prayer on the minute every minute of each day, traffic was a parking lot from JFK to Manhattan.
In all seriousness, the New York City hustle is alive and well and starts the second you step off the plane. Scammers will try to convince you to ignore the yellow taxi cab line and instead get into an unmarked car, they claim to be a taxi that lacks a cab fare meter, driver identification or anything that would indicate that this wasn’t a random persons private automobile. I’m not ashamed to admit they caught me with that trick once, a decade ago, but now I am older.
For all the talk of people fleeing to Miami or elsewhere, it’s not noticeable. The pace of the city is unmatched. It seems like you’re on the move from the second you wake up. I’ve been to the city many times but this was my first time staying in Chelsea and I regret not doing it sooner. I left my hotel at 8AM went to Equinox, grabbed a coffee at Fellini in the meat packing district, did the whole High Line, went to the Little Island, then the Whitney Museum. At about 4PM I realized I had never strayed more than a mile (1.6KM) from my hotel. I still saw only a small part of Chelsea.
Here’s a little gym hack I learnt. At least in New York, many of the Equinox locations stopped offering guest passes. However, one of the people working there told me I could book a 30 minute robot massage (more on that later), then use the gym and/or do one of their classes for $60. That isn’t an insignificant sum of money but with boutique group classes costing up to $50, this is actually a pretty good deal. This way you might also be able to claim it for insurance (tbd).
Walking around the high line, you exclusively see tourists. You can tell they are tourists because they walk unbelievably slowly. If that doesn’t help they’re also stopping every few steps to snap a photo. New Yorkers on the other hand walk like they’re constantly late for something. The reason being, they probably are. I lived through it when I ran to Central Park. It was great but I made the mistake of only looking at the distance to the bottom, not the middle. That extra 3 KMs each way, meant I had to sprint back between red lights all the way down 9th avenue.
I came back for the robot massage and it’s exactly what it sounds like. You get into a massage room and you see these robot arms looking like they belong to Dr. Octavius from Spiderman. You lie facedown, adjust the settings and hope it doesn’t become sentient and kill you for forgetting to thank Chat GPT.
The massage wasn’t bad. It wasn’t as good as a talented masseur/masseuse but it was far from the worst massage I ever received. In 30 minutes it was able to noticeably iron out some knots, so that was good.
After that I met a friend for dinner in the financial district. I walked from Chelsea which takes about 45 minutes. On the way there I noticed at least two or three chicken chain restaurants I had never heard of. How can they sustain this many chicken based restaurants in America?
Besides the abundance of chicken restaurants, I did notice there appear to be way more woman in New York than men. Part of this might be explained by having arrived from San Francisco, but there have been a few articles circulating claiming as much. Apparently they did a singles event where they charged women $100 to attend, men could come for free and women still outnumbered men 3-1.
When I first saw it I assumed it was clickbait nonsense but literally every conversation I overheard at a restaurant, bar or even in line at the Comedy Cellar featured a woman complaining about the lack of men in New York City or wondering why their situationship won’t text them back? These are of course limited, anecdotal observations, I’m sure nobody has ever struggled with dating in big cities.
Still though, it must suck to be a single New Yorker and feel like these Equinox robot masseurs have a more successful dating live than you do. No wonder people are trying to ban AI.
I previously covered this in Is Pretty (Male) Privilege a Thing? but part of the problem is 50-60% of women covet the same 10% of men who are tall, handsome, make a lot of money etc. A couple of years ago an article claimed half of Gen Z women were in relationships while only about 20% of the men were. The natural conclusions were either Gen Z women are dating older guys or some Gen Z men are dating multiple women. It’s creating a K Shaped dating economy.
This isn’t being helped by finance bro photoshoot a couple weeks ago. Just joking, those guys are definitely getting roasted by everyone at their work and will probably be fired if their company didn’t sign off on this. This is definitely a topic of conversation around the city. That along with the volatility in the private credit space.
Whereas in SF, people are mostly just focused on the financial markets related to tech, New York is exposed to the world economy. The price of oil is wreaking havoc across the real economy, they notice this in NY. Bad timing for Blackstone, Blue Owl and other firms trying to convince markets that Private Credit Isn’t in a Bubble.
Yet for now, so long as finance bros can afford Celine suits and there are lines out the door for every pilates studio, wine bar and four dollar sign restaurant, you know New York is in good shape. Regardless of how hard it is to date, there’s a reason why so many people happily put up with the high rents and overcrowded streets.
From John F Kennedy Jr look alike contests to world class cuisine from almost any country imaginable, New York still has it. There is a reason people tolerate the high rents, overcrowded streets and chaotic dating market. The city has an energy that is hard to replicate anywhere else.
San Francisco and New York both have it, but they channel it differently.
Are they the most liveable cities? Unless you’re a very high earner, no.
Yet still there’s a reason so many flock to these cities.
San Francisco feels like a giant laboratory. Everyone is building something. The conversations revolve around products, startups and the future.
New York is still the command center. Technology is just one small part of a broader conversation revolving around markets, geopolitics and competition. The city runs on ambition and capital.
Spend a few days in both places and the contrast becomes obvious.
If you want to build the future, you’ll likely be drawn to San Francisco. If you’d rather compete for power and influence, there’s still only one New York.
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I really enjoy your writing style !
Great write up!