Notes from the SF Party Scene

On billionaire party houses, tech billboards, SaaS couches, and magic cars

[Necessary caveat that I am of course making broad generalizations about cities that have hundreds of thousands of people. It is totally possible for other people to come to different and even opposing conclusions!]

It's been a few days since I got back from a two week stint in the Bay. I was there for work, sort of. When you're in the startup world, any time in the Bay is ostensibly for work. You are just inundated with people who can't help but talk about technology, companies, markets. It's a great place to learn about competitors; it's the only place to catch up on the state of the art. In my case, I had a chance to meet up with friends and mentors while crashing on five or six different couches. This is a pretty regular pilgrimage for me, one that I've been doing every year for at least 7 years now. The big benefit of being almost thirty is that many of my friends had upgraded their couches to spare bedrooms, so I got to sleep a bit better than I usually do.

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I've always held a sort of anthropological interest in San Francisco. That beautiful, shining city on a literal hill, surrounded by the gentle waves of the emerald bay, so far in miles and culture from the New York streets that I grew up in. It's so incredibly weird. And visiting for any extended period of time puts into sharp contrast the differences between cities, and how cities are these macro level organisms with value systems and beliefs of their own that trickle down to (or filter out) the people that live in them.

San Francisco is a city of dreamers. It's core enterprise is creating magic. And as a result, the town values the individual. It exalts archetypes — the founder, the builder, the prodigy. The question that people ask is "who are YOU? What are you interested in? How are you going to change the world?" Social life in SF is grounded in these questions. Half the conversations are about what everyone is working on these days (everyone is working on something). The other half about singularity, our post-work future, what does it mean to live on in the machine?¹ Everyone is grinding, no one has a healthy work life balance. The startup "family" dynamic is a well understood and oft-reported on phenomenon. People are encouraged to become friends with the people they work with. They have meals together, share hobbies, sometimes even live together, as they work impossibly long hours to make a fortune. The whole thing inevitably makes work much more social. But there's another edge to it. All social interactions feel distinctly transactional, because you never know if the person you're chatting with at the party is going to be your next hire, co-founder, or lead check. Casual conversations become opportunities, networks are a form of currency. Business leaks into friendship leaks into romance; I've never seen drama and backstabbing quite like what's endemic to the SF hacker house scene.

NYC is notably not like this. NY is a town of bankers. The main question people ask in the NY tech scene is "what can you do for me?" It's all about returns on investment. NYC is more grounded as a result. It has to be. The companies think more about pmf, and are more closely connected to specific business needs. They view technology as a means to an ends. I think that means that NYC is always a year or two behind in tech. You can never get the crazy valuations and capital necessary to build OpenAI in New York. Partially, that's because the appetite isn't there, it's too speculative. And partially, it's because the default mood is one of pessimism. "You think you can change the world? Who do you think you are?" People aren't on a mission in NYC, the way they can be in SF. They want to make money, sure. But maybe not change the world. And that leads to cleaner delineations between work and play. People have lives outside of the office (unless you're in IB). It's easier to go catch a movie or go to see a play when you aren't chasing a moral imperative. The friends you make, the people you spend time with — they aren't primarily connected to you through your work. They have their job, you have yours. It makes the friendship a place to share in each other's struggles in a more emotional way. After all, if you're spending all your down time with your CEO, it's not exactly that easy to bitch about your 9-5. You may think that this all makes NYC a worse startup town, but I don't think that's true. It's just different. The startups are more sober, more business oriented. The companies care more about how they can use technology as a means to PMF, instead of as an end to itself.

A good friend of mine summarized all this as: in San Francisco, the people are nice but not kind. In NYC, the people are kind but not nice. People in SF will, at first meeting, give you access to their network, their resources. They will eagerly hear what you're working on and excitedly talk to you for hours about whatever. But they'll drop you if you are no longer useful in some way. Meantime, in NYC, people will cut you off in traffic and curse you out on the street. But close friends last a long time; personal utility is rarely the driving metric for friendship.

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The blurring of work and life can result in some very strange things. My personal favorite is the billionaire SF party house.

The basic idea is as follows. Because it's normal for CEOs and execs and investors (and, in the case of investors, it is often part of their job description) to hang out with employees and potential hires and new grads and dropouts — to generally be social — you will often have people of vastly different socio-economic strata interacting with each other. Many of the CEOs and execs and investors are fabulously wealthy. They are potentially multiple time founders, or perhaps extremely successful investors. Many of the employees/new grads/dropouts are…not.

If a rich billionaire CEO investor wants to hang out with his employees after work, do you think he's going to go to some employee's Mission apartment where they are living with 3 other roommates? Hell no. The billionaire CEO investor has a special property for exactly this purpose: the billionaire SF party house. This is a beautiful manicured gorgeous space, with high ceilings and ornamentation. Often there will be a fountain built into the wall right across from the entryway. The grounds will be landscaped to perfection, the furniture immaculate, there will inevitably be libraries and a piano and a massive kitchen. And, to a first approximation, no one lives there.

I find myself at one such house basically every time I end up in SF. I want to keep that trend going, so instead of describing anything too identifying from my most recent adventures I'll share a story from a few years back. In 2022 I went to visit a friend of a friend, an 18 year old college dropout, who was living in one such house. The place was a bit isolated — it was in Millbrae or Burlingame, not exactly in SF proper. We drove in through a gated driveway onto one of the most luxurious properties I've ever seen. Supposedly, said friend was renting the place from a VC who owned the place. Though it's more accurate to say that he was renting a dance studio out back. If I remember right, his little building didn't have a shower.

The house itself was a liminal space, something right out of a David Lynch movie. The first floor had extremely high ceilings. We spent a lot of time in a beautiful library with huge bookshelves and whiteboards strewn about. The requisite piano was in the back by the windows. Turn a corner and you enter the basement — a narrow set of twisting corridors and wall to wall carpeting, low headroom and harsh bright lighting partly illuminating strange empty rooms with whitewashed walls. We saw a sign that said 'mattresses' with an arrow pointing decisively to the left, but upon following that path we landed in a big dead end room that had a half-build ping-pong table in it. The basement had an exit (how many exits were there? We weren't sure) near the kitchen. Every dish and utensil in the kitchen was spotless, and the fridges were empty. But there was a doordash bag on the counter; someone had ordered Chinese. We weren't allowed up past the first floor. Rumor had it that one room of the house was being rented out by Andrej Karpathy, though I never actually saw him.

But I saw a lot of other people! We ran into at least a half-dozen other people just milling about the hallways of this beautiful, lifeless house. And we had some variant of this conversation with each one:

"O, hey there! Nice to meet you. My name is Amol."

"Hi Amol, great to meet you. What are you doing here?"

"I'm just visiting a friend, he lives in the shed out back. What about you, do you live here?"

"O, no, I don't live here."

"So…why are you here?"

"O there was a writing workshop here two days ago."

What do you mean it ended two days ago? Why are you still here???

Not everyone was there for a writing workshop two days ago. One person we met "managed" the house — I guess this meant, like, making sure the landscapers were getting paid and the fridge was stocked and full? One person was one of said landscapers. One person was an artist who was filming something or the other. WHERE WERE THE PEOPLE WHO LIVED IN THE HOUSE? The koi pond had a dozen koi fish that were each worth $20k! There were more fish that actually lived there than people!

As a brief aside, this sort of thing does not really seem to exist in NYC. O sure, there are billionaires, and I am told they do have houses. But there is much more stratification in wealth — rich people mostly hang out with other rich people in exclusive rich people hangout spots. Seems like this is more egalitarian in the Bay.

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My favorite conversation from my time in SF:

"I had to log in to my couch once. And there was a problem with the login! The couch was fucking out of date or something!"

"O, wait, so were you like buying SaaS for your couch?"

If that doesn't encompass every Bay Area house party convo, I don't know what will.

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San Francisco has always been a bubble. Much of this is selection bias. There is a culture of encouraging young, brilliant people who love to talk about technology and math and science to the same place, and encouraging them all to hang out with each other to talk about technology and math and science. So of course, it stands to reason that the general social life in SF is a bit more skewed to a particular kind of person and area of interest.

But nothing makes the bubble quite as clear as the billboards leading to SF from the airport.

O man, the SF tech billboards. These are amazing. If you ever want to understand what the latest fad is in SF, just drive north towards the city. A few years ago, all of the billboards were about crypto. Now they are all about AI.

I didn't get a picture, but here's a sketch of my favorite of this trip:

You cannot imagine the whiplash I gave myself from the double take as I drove past. A database company?

I think of startups as information arbitrages. In order to take advantage of an arbitrage opportunity, you need to understand both sides of a trade — what is possible, and what is needed. I think folks in SF have a very strong understanding of the tech, they know more than anyone what can be done. But the bubble is strong; the average founder assumes that the rest of the world is where SF is, and as a result has no idea what is actually needed. They miss low hanging fruit, preferring instead for high tech solutions looking for problems.

Both Drew Houston and BrandonM understood that you could use an FTP server to host remote files. But only Drew Houston understood that approximately no one else in the world knew this.

I was talking to a smart guy at one of the up-and-coming Silicon Valley incubators.² He was interested in sports, and sports tech, and launched into a product idea for this incredible technical innovation that would use computer vision and pose modeling to exactly watch how players moved around in order to give precise advice on how they should change their form. This is probably a business with a few dozen buyers — youth coaches aren't, like, going to buy this. Meanwhile, the average professional sports team backoffice hasn't had a software update in a while! I think if you're interested in sports tech, there's probably lower hanging fruit. But the average silicon valley founder just assumes, incorrectly, that the low hanging fruit has already been picked.

Many such cases.

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I was in the Bay when I wrote my piece on Gemini 2.5. That rapidly became one of my more popular pieces, I guess the timing was right. But what was more interesting to me was watching the SF AI scene react to the news that Gemini was out, and was actually really good.

The first few days after release, there wasn't that much noise. But by the end of the week, basically everyone I knew had heard about the model, and roughly half of them had made the switch to Gemini already. I flew into a town that was obsessed with Claude, and flew out from a town that was mostly on Gemini.

I think this is a huge validation of my thesis that the LLM infra layer has massive winner take all effects.

Going back to LLMs, I think you see roughly the same market dynamics. LLMs are pretty easy to make, lots of people know how to do it — you learn how in any CS program worth a damn. But there are massive economies of scale (GPUs, data access) that make it hard for newcomers to compete, and using an LLM is effectively free5 so consumers have no stickiness and will always go for the best option. You may eventually see one or two niche LLM providers, like our LexusNexus above. But for the average person these don't matter at all; the big money is in becoming the LLM layer of the Internet.

And, as expected, there's only a handful of LLMs that matter. There's a Chinese one and a European one, both backed by state interests. And there's Google, Anthropic, and OpenAI6 all jockeying for the critical "foundation layer" spot.

The economics of LLMs means that it is critical for these players to have the best models. There's no room for second place.

Every couple of days, I hear about some new company or lab that is trying to compete with the big models. They will release some really cool tech, maybe even open source some weights that do better on benchmarks than llama or deepseek. But no one cares. What happened to Mistral? What happened to StabilityAI? Even Llama is struggling.

As long as the top labs can incorporate any and all research from the smaller upstarts, the new models will all be left in the dust. There is no moat, every baseline general intelligence provider is essentially equivalent to every other one and pricing is essentially a non-issue. The entire industry can switch providers with a single variable change!

Maybe not surprisingly, I'm still bullish on Google.

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One thing that I love about SF is that the whole place feels a bit like a college dorm in the best kind of way. You can pop in and introduce two friends, acquaintances, or people who are total strangers, and you can spend the night having deep philosophical conversations on some rooftop overlooking the city.

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Silicon Valley is a lot younger and far more conservative than I remember it.

On the first point, I may just be getting old. As mentioned above, I'm about 30, which is ancient for Silicon Valley. Working backwards, I graduated highschool in 2014, and was in college from 2014-2018. In 2014, there were maybe only two dozen or so college-dropout-wunderkinds wandering around the Bay. A lot of them were at Makeschool, a bunch more were Thiel fellows. Almost all of them just had weird circumstances that landed them there — parents couldn't afford college, or they were smart kids who didn't have the grades, or (in at least one case) they had a pretty violent injury that made the college path untenable. And they all kinda knew each other, just because it was nice to hang out with other kids who couldn't drink at the bars when their companies would do offsites. But on this most recent trip, it felt like every other person I met was some 18 year old who decided that college wasn't for them and they were going to make it big in VR/AI/robotics/whatever. They all had great family and home lives and tons of opportunity. They just wanted to be in the Bay, doing the founder thing. I think this probably makes sense — it's easier than ever for young founders to start companies, and the value of a college degree has cratered. Still, it felt a bit odd.

On the second point…well, that's just a sign of the times isn't it?

Now, don't get me wrong, Silicon Valley isn't conservative. The average tech person is a pretty staunch Democrat. Not necessarily a far-left progressive (though there are those types too), but, like, a college educated Biden/Obama/Clinton middle-of-the-road liberal, maybe with some libertarian tendencies — the "free speech" kind, not the "taxation is theft" kind.

But there was a small, vocal minority of outright Trump supporters. And, if I'm being honest, it was quite hard not to notice their similarities. They were, to a person, male and white. To the point above, they were also all very young — not a single one above 21 years old, most of them hadn't gone to college and were instead trying to make it as founders and entrepreneurs. And every single one of them was extremely nihilistic. "Blackpilled", to use their words.

This felt very strange to me. Here was a group of people who were, by every account, living some of the most blessed lives on the planet. They were all healthy. They had decent relationships to their family and friends. They were surrounded by people who were eager to give them the resources to fulfill their wildest dreams. That's not even an exaggeration. In between complaining about the decay of the city, one of the group mentioned off hand how a VC had bought him an 8sleep mattress and sensory deprivation spa treatments. I looked it up later — the 8sleep that he got was worth $5000 dollars. At the same age I was sleeping on a $100 foam/plastic twin bed.

In spite of their obvious good fortune, talking to them was a bit like talking to a 4chan greentext. They would joke about edgy bullshit — how it was good that 10 year olds were addicted to phones so that they could make money off them, that it was time for democracy to die and be replaced by techno feudalism, that we should renormalize homophobia as a society. It took me a while to realize they were serious, they were laying the irony on so thick. Why on earth were they so cynical? What did they have to complain about, that they were all so eager to watch Trump "burn it all down"?

That last comment — the one about homophobia — was especially surprising, because it was said by a young 20 year old who was openly gay.

I agree, this is confusing.

My host in SF is very plugged into the SF LGBT founder community. After the party, he said that political affiliation was starkly split by age. Anyone above, say, 25 was strongly Democrat; everyone below was conservative. That younger crowd all hit puberty after 2013. This was the height of the gay rights movement; Obergefell v Hodges was decided in 2015. Attention spans are short, but it seems memories are even shorter. None of those folks grew up in the stigma of the 90s or 00s. And so, a young gay man could stand on a rooftop at a San Francisco house party in 2025, and laugh and say that society should renormalize homophobia while voting for Trump, all without realizing how many people fought for his right to make that joke.

While I’m on politics, I did get a pulse on how some of my older friends in the Bay were feeling about everything. The general sentiment? Uneasy. Many of them were strongly against the current administration, and were equally against the open support from some of the Silicon Valley elite. But they were only willing to say so in hushed tones, concerned about who in the area may be listening. To half-quote a friend of mine: “Everyone is a bit scared, no one wants to stick their head up. The Trump people definitely have all the power right now and have shown they’re willing to use it.” This shook me more than I’d like to admit. I always thought of the Bay as a liberal enclave within a liberal enclave. Things change quickly.

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Hot take: I'm increasingly of the belief that the young college dropout is worse off for going to SF. If you were like me when you were 18, you were hot headed, filled with opinions and incredibly confident of your correctness. I personally did not love my college experience; in retrospect, I felt that there were much better ways to use that time. But I will say, being around other hot headed opinionated 18 year olds with completely different opinions polished off a lot of my rough edges. It gave me a level of epistemic humility, as well as training in being the kind of person that can effectively work with others. You know, traits that are generally good for leaders.

The average 18 year old in SF is sorta given the opposite treatment. They are exalted for their youth and for their aggressive arrogance. And this makes sense. For a VC backed company to work, you essentially have to make an economic argument about how the 'efficient markets' are extremely wrong, and you somehow aren't. That's a bold claim to make! The founder community is structured to take the most opinionated people and encourage them to be more opinionated, it kinda has to be. So I get why Silicon Valley selects for people who are very pointy in that way.

But also, man, that really warps a person's sense of judgement.

If I was 18 and told that everything I thought was correct, and also given a bunch of money, fancy mattresses, and spa treatments by billionaires, my head would've inflated to be the size of the moon. And I probably would've simultaneously been so awestruck by the first billionaire who gave me the time of day that I would have ended up falling into some kind of cult-like hero worship. In that light, I think it's not surprising that so many of the extremely wealthy seem to have an entourage of young folks around them, hanging off every word like young acolytes. Now, to be fair, it does seem like many of those kids end up getting funded to the tune of hundreds of millions of dollars, so idk maybe it all nets out positive. Still, second and third order effects on one's psyche seem…pretty bad.

At the very least, this line of thinking has lessened some of my own FOMO for actually having gone to college, instead of dropping out early and heading to the Bay.

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Every time I go to SF, I take a Waymo at the first opportunity.

If you haven't taken one of these yet, it is an absolutely magical experience. Watching the car pull out from the pick up stop on its own gives me shivers every time. It is a seamless experience. Self driving is here, like 100% fully here, and is just a daily fact of life for the approximately 800k people living in San Francisco.

Unfortunately Waymos don't do pickup out of SFO. So I generally have to go into the city first, and then take a waymo. But the first chance I get! And I'll often take a Waymo on my second chance too! Whoooo waymo! Taking me from point A to point B!

And then generally when the third opportunity arises, I look at the price, which is generally 2-3x the price of a Lyft or Uber. And I'll look at the estimated arrival time for the car, which is generally like 10 minutes at least. And I'll mentally budget an additional 5 minutes for the drive, because the Waymo cars are very safe (which is great!) and as a result mildly slower.³ And I end up calling some other rideshare. Waymo is magical, but apparently it's not worth $10 and 5 minutes of my time.

San Francisco is this land of crazy paradoxes. There are literal self-driving cars on the streets, next to some of the worst homelessness and poverty in the country. How does a town with one of the highest GDP per capita get so many things backwards? IMO it's because it is way too easy to lose sight of the magic. Maybe that's a theme of all of these notes. When you surround yourself with magic all the time, it stops feeling quite as magical. And so you get all these weird outcomes. LIke these hyper-specific bubbles. Or these strange luxury beliefs. Or these funky social cliques.

Like I said at the top, San Francisco is a city of dreamers. As long as that is true, it will continue to be a center for innovation and progress. But it is also fundamentally untethered. And so it will also continue to be a place of two-sigma weirdness on every axis. Maybe these things are necessarily correlated. It's unclear.

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For now, I think there's a lot of value in living in NYC but visiting SF regularly. There's an arbitrage there — take the latest and greatest from the West Coast and package it into something sellable on the East Coast, and you have a successful business. And I just love NY, I grew up here, it's my home.

Still.

This trip was a lot of fun, despite what parts of my writing may suggest. SF as a whole felt alive, in a way that it hadn't been since COVID. In 2023 and 2024, the city was still in the throes of pretty terrible local mismanagement, while the downtown truly was a pretty bad place to be. In 2025? We're so back.

I'm thinking of making the trek twice a year now.

1. The questions change depending on the latest tech trends, of course. Pontificating is free, everyone has takes.

2. There seems to be a general consensus that YC is dead or dying. The brand is overdiluted, the terms are bad, the playbook and network less exclusive. As a result, a few others are trying to swoop in to make a name for themselves.

3. You could probably do a pretty interesting study on how much people value time efficiency over risk to life and limb. I imagine the results are pretty skewed in the wrong direction.