A societal failure on all levels
A week in San Francisco
I’ve been in SF for the last week to attend Stripe Sessions. It’s been a very long time since I’ve been here. The last time I can recall visiting was in 2022 for a team offsite while I was still working at Stripe. It’s been a very emotional trip, to say the least: I visited Oakland for the first time since I moved away in the summer of 2018, and it’s remarkable how different everything is. My favorite cronut spot is gone. Restaurants where I was a regular closed (probably during the pandemic). Public works projects have wrapped up. Pay-by-the-month parking lots have turned into high rises.
In the east bay, Oakland feels like it used to. There’s a sense of hope. A stranger said hello to me as I walked through civic center. Hotboys Chicken was packed.
In the four years or so that I lived in Oakland, there was never a moment where I felt unsafe. Walking downtown, I still didn’t feel unsafe.
San Francisco, though, doesn’t feel like it used to.
What the hell happened, guys?
The first thing that struck me about SF was the absolute mania that seems to grip the city over AI. Every billboard. 6th and Howard has three identical billboards advertising the same AI company. Everyone wants you to use their agent. Everyone wants you to build AI apps. Everyone in a company t-shirt is talking about tokens or context length or MCP. Nobody even bats an eye, this is normal. But it’s not normal.
This wasn’t how SF was during the crypto bubble. This is something different. The technology—an engineering and academic marvel—is being conflated with the application of the technology—largely an unmitigated shitshow.
I work in AI. I live and breathe AI. My partner hates my enthusiasm for it. And yet I don’t have the level of brainrot that the tech bros here seem to be experiencing. I have every confidence that the folks at OpenAI and Anthropic are cooking amazing things, and they’ve all earned the right to speak with authority. But there’s a near-endless list of AI startups and thought leaders in this godforsaken city who’ve built an “agentic platform” to help you ship/build/think/do faster.
And at the end of the day, they’ve built a Claude wrapper.
For all the hot air these people are putting out about how SaaS is dead, their “AI agents” can be replaced with a $20/mo Claude subscription and a one-shot prompt to build the very tools they’re selling. It’s a failure of imagination to think that Codex can replace SaaS companies but not the AI suites that will reportedly be doing the replacing.
I could only handle so much time around gaggles of tech bros in matching company-branded red and white Nikes as they vapidly talked about replacing knowledge workers with “agent swarms” while being seemingly unaware that—even if Claude didn’t occasionally nuke production DBs—they themselves are the first airheads worth firing.
Why AI isn’t going to replace humans in most jobs for a long time is a topic for a different blog post. Let’s pray, though, that my words never become important enough for anyone to really care what I think about the fate of human labor in the age of machine learning.
The reason I’m even bringing this up has nothing to do with AI at all. It has everything to do with the sheer contrast with the state of this city.
No but for real, what the hell happened?
At the risk of sounding like a conservative, let me preface this by saying that I’m writing this because I love San Francisco and always will. This city looks like hell.
SoMa between fifth and ninth streets looks like the Tenderloin used to look. The homelessness crisis has exploded. I’m not even sure if “crisis” is the right word anymore. I’m not even sure if the English vocabulary has a word to describe what’s happening in this city. It’s disgusting and immoral and absolutely everyone should be ashamed that this is what the Bay Area has become.
Let me be extremely clear: I don’t blame the folks in crisis for this. I don’t think the solution is locking people up for being homeless. The victims here are the folks in crisis, not the residents being forced to put up with them. You can’t change my mind on that.
What’s appalling to me is how little everyone cares.
I watched a brand new Rivian R1S wrapped with advertising for a startup drive down the street blowing a patient belonging bag behind it.
I watched a woman pushing her two children in a stroller past a man with a broken leg, sitting in a wheelchair marked as hospital property, as he struggled to ignite his lighter so he could smoke meth.
I watched a man unloading a truck full of Article midcentury modern furniture next to a tent.
I went to breakfast and was seated next to a company executive and someone who seemed like they worked for a VC, discussing how to force an employee they dislike into retirement.
I saw someone sleeping under a nylon sleeping blanket on the sidewalk next to a bikeshare rack, with each bike’s rear tire emblazoned with the Gemini logo and the phrase “A new kind of help from Google.” I’m sure they appreciate the help.
Street poles with flags reading “Believe in San Francisco” along with a photo of a trolley car just across the street from charity housing with five people out front having drug-induced episodes.
As soon as the sun starts to go down, the tourists and the techies recede and the city starts to look very different.
But there’s nothing to be done!
You can’t force people to go to shelters.
You can’t force people to get treatment for mental health issues.
You can’t force people to not commit crime.
It’s striking to me that we have actual, real-life politicians suggesting that the chronically homeless should be arrested and sent to state-sponsored prison, but they seem to lack the capacity to conceive of an alternative where the same folks are given state-sponsored food, housing, clothing, and medical care in a setting where they can have dignity and a path back to society. The idea that you need to put guards and bars up to care for these folks is infuriating.
It’s striking to me that companies build beautiful high rise office buildings with luxurious amenities, but they lack any sense of community or responsibility whatsoever for the people that sleep under their porticos.
I get it: providing services—and not just services, but the RIGHT services—is a hard problem. I went on a tour of the Tenderloin many years ago, and the guide explained the complex web of charities and the perverse incentives that local government creates that stymies their effectiveness. It’s not a problem that’s going to be solved overnight. But the city managed to build and open the Central Subway, which is apparently a tractable problem, but the crises on the streets literally directly above continue to worsen at an alarming rate. Tech bros: where the fuck are the “agent” “swarms” that are helping the folks living in the gutters of your city?
I think the people I’m most disappointed with are the leftists. Maybe that makes me a moderate, I don’t know. But what I see is Mayor Lurie giving up on trying to build 1500 shelter beds while the abandoned San Francisco Centre sells for a little more than three times the amount he raised from donors.
I’m no mayor, but I’m pretty sure the city could have found a way to strike a deal to use a little bit of that over ONE MILLION SQUARE FEET of space to put up a couple thousand beds. They could maybe make up for closing shelters by repurposing some of the downtown blight.
“wElL tHe BuSiNeSs PeOpLe WoUlDn’T gO fOr ThAt!” It strikes me as political impotence if you can’t convince the same tech thought leaders that call your city “the most beautiful place on Earth” to do literally anything to address a crisis that receives ongoing national attention and ridicule. Donald Trump can allegedly privately fund the construction of his gilded ballroom. If Coinbase, Google, and other California companies can pitch in for that, I’m sure they can find it in their hearts to end the crisis of abject poverty in their own back yard. Maybe being voluntold to pay their share with Prop C killed what’s left of their moral compass.
I can’t empathize, I don’t make $50M/year.
When you look at the donors Lurie was pulling, they’re all charities. Where the fuck are the AI companies? The Bay Area is supposed to be the innovation capital of the world. If each of these companies put ONE PERCENT of the money they spend training a SINGLE FRONTIER MODEL towards the problems SF is facing, the city could hang more than a few Mission Accomplished banners.
It’s tricky to help people with addiction. But one must admit that substance abuse is a problem that creates a feedback loop that keeps people on the streets. It’s inarguable. Stable housing is the single biggest predictor of treatment engagement, but twenty years of NIMBYism has shown us that simply shouting “WE NEED MORE HOUSING” back and forth at each other isn’t going to will high rises into existence.
Larry Ellison’s private jet costs $10,000/hr to operate. For what he paid to travel in November of 2025 alone, you could literally pay every unsheltered addict in SF to pass drug tests for months1. Which, as it turns out, is numerically a good thing, even if it’s the sort of thing Fox News would lose their fucking minds over.
San Francisco, despite the (alleged) exodus of rich assholes, remains consistently in the top ten highest concentrations of billionaires in America. Imagine loving a place enough to call it home, having so much money that it’s essentially impossible to spend it all, and then not giving enough of a shit to actually do anything to fix the problems. Less than a half a percent of the collective wealth of the 55+ billionaires in SF is essentially equivalent to the entire SF Homelessness and Supportive Housing yearly budget.
Angry at the right people
I don’t want to shit on the people in SF who are doing good, important work. I know there are folks out there who really care and who want to make a difference. Lurie is no Mamdani, but I certainly don’t envy him or the tough choices he has to make. I don’t blame him, and I honestly don’t even really blame Mayor Breed for failing to deliver on most of the things she’d promised either.
What salts my fuckin onions is the prosperitycore thought leadership that has infected silicon valley. OpenAI posts “We want a future where everyone can have an excellent life,” and yet contributes next to nothing to fixing the problems manifesting literally outside its front door. Meta has been purchasing hundreds of thousands of H100s—each almost equal to the cost of supportive housing for a person who could use it—while leaving more than half of its 2019 housing commitments unfulfilled. The Chan Zuckerberg Initiative pulled back $50M in funding for housing grants and plans to end housing initiatives by the end of 2026. A round of applause for all those involved. 👏
It’s a disgusting shame, and it makes me deeply resentful of the people who can actually do something…but simply don’t fucking care.
“Contingency management”, as it’s known. I’m seeing about 44 hours in November 2025, that comes out to ~$440,000. 16 weeks of treatment looks like a little over $1100. That’s about 400 participants. If you take the number of unhoused people in SF and estimate that maybe a fifth of them would be eligible for contingency management (both because of their condition, ability to participate, and the applicability of their addiction), that number roughly works out.
You’re misdiagnosing a political problem as a failing of morality or charity. Which of course is tempting because of all the gross hype in SF. But, if SF threw out its land use rules and adopted those of Houston, not exactly an exemplar of rectitude, it would almost mechanically have fewer obnoxiously unhoused. They would have fewer people falling in to homelessness because rent would be cheaper and charitable donations would go further to helping more people, more comprehensively. The problem is that people in SF are adamantly and deeply against such changes, although Lurie is marginally better than nothing on that front. My point is, you can’t simply throw money at a structural problem; you have to change the structure. And then, you can’t effectively change the structure just by throwing money at it either. Rather, people work through existing institutions and movements for incremental change. Which is all very unsatisfying and all the more so because of the AI hype but so it is.
I’ve had this exact same sequence of thoughts for several years now. I visited for SF for an AI hackathon in December 2022 right after ChatGPT was released, and took BART to Berkeley to get lunch at Sliver Pizzeria. The situation there was so bad that the restroom was closed even to customers. I took my greasy hands over to Chase where I have a bank account and an employee said, “you seem fine, you can use the bathroom”: they have to individually evaluate individual customers to determine who’s at risk of overdosing on the toilet or something. It made me think, “the people who live here are completely nuts. They somehow have the best AI technology, but absolutely cannot be trusted with it.” The whole thing about “avoiding the permanent underclass” is obviously no joke when you see the drug users passed out on the sidewalk.
I’m experimenting with AI story generation, which I know is not really helping the problem at all, but I thought this was funny at least:
https://docs.google.com/document/d/1UkSceM7tZA5AoDRN3mQ5gwXaewde2XNmGCIbXhbYbOg/edit?usp=drivesdk