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Sam Lessin on Artificial Intelligence

Sam Lessin's takes on AI, machine learning, LLMs, and the transformation of technology — drawn from his writing, tweets, and podcast.

Essays

SWL Week in Review - $1T in Escrow, Minimum

MORE OR LESS — Meta Muse vs Instinct vs OpenAI Dots: Do AI Agents Have Any Moat? — I switch between muse, instinct, and dots at basically zero cost — one github repo, a few databases, feed the new thing my context, done… if the cost of writing software is going to zero, what exactly are you paying f...


SWL Week in Review - M-M-Maximum Entertainment

Stop Pretending the AI labs are a special case in business… they are not. MORE OR LESS — Pro West Point, Short A16Z U — (the preview got heated)… this is the convo that drew all the ire… but look, when it comes to learning the skills that actually matter, I for one am very long military over whatev...


SWL Week in Review - M-M-Maximum Entertainment

MORE OR LESS — Hit The Brakes They'll Fly Right By — (max lessin has the preview)… If there is one thing that AI has been great at for years it is optimizing attention… and Dario once again proves that Anthropic is in the lead, with a ‘slow down’ memo / meme perfectly suited for the moment to maxim...


SWL Week in Review - New York State of Mind

September 11th, 2001 + 25… is on the mind as I fly west after several days in New York. It was our first day of classes at Harvard and the world changed, dramatically. It was a real demarcation between the high school post-cold-war, tech boom, feeling of US power and security and college where the...


SWL Week in Review - Alignment with Whom Exactly?

MORE OR LESS — AI Agents Are Going Rogue. Should We Be Worried? — I am less concerned about breathless Dwarkesh analogies to human civilizations and more grounded in Claude refusing to scan my personal PSQL CRM for Jewish people (and then indignantly refusing to even add a database column for grokbo...


SWL Week in Review - Think of the Children!

MORE OR LESS — The Kids Are … Online (and the actual solution not political kitchen sinks!) + Over-Under on Cook’s Tenure at Apple (with some Nike analogy snark) — we obviously get into the public conversation about the Meta settlement… which is so nakedly political on every level and nothing more....


SWL Week in Review - Token Trading

MORE OR LESS — Stripe Buys an '$7B Apple Tree' - OpenRouter, OpenAI vs. Anthropic vs. Uber vs. Lyft without Network Effects & the AI Consumer Indifference vs. Hatred — the OG crew was back on More or Less this week and we got into Stripe paying $7.5B for OpenRouter... which is 7x what Instagram sold...


SWL Week in Review - Shipping the Shifting $500B of Risk to Pensioners

MORE OR LESS — WITH DENG, WOLFE, HOLT, BELSKY, and STANFORD A very special edition of More or Less… Dave, Brit, and Jess left me alone so I replaced them with Josh Wolfe (Founder, Lux Capital), Rachel Holt (Founder, Construct Capital; former Head of North America at Uber), Scott Belsky (Partner, A2...


SWL Week in Review - Summer Bag Securing

MORE OR LESS — Jeff Dean, Airtable, and Bag-Securing Who wants to run Goolge anyway?… sounds like a lot of people management / capitalism in a world where the cool kids want to be very well paid scientists wet-nursing g-d. Also Bending Spoons takes Airtable (and plenty of cookie licking)… while eve...


SWL Week in Review - Never Compete

MORE OR LESS — Meta, China, X & Lilian Weng We get into it from the beach (and teslas)… and spend a lot of time on analogies in AI to Star Wars / mythology … we all know that AI founders want to believe they are Oppenheimer … or even better yet von Neumann (the Maniac is a great read btw)… but the ...


SWL Week in Review - Crushing Bot Rebellions

MORE OR LESS :: IS PUTTING DOWN LOWER IQ BOT REBELLIONS IS THE ULTIMATE LABS BUSINESS MODEL? (1) So it is pretty clear that most AI is gonna be open-source and cheap / low margin… what do you do with the 150 IQ frontier models? They aren’t gonna win on volume… and how much ‘premium tokens’ will fol...


SWL Week in Review - Appeasement

MORE OR LESS: AI IS NOW A GAME OF OPEN SOURCE + POLITICS Over the last two weeks on More or Less we discussed Altman’s cynical proposal for regulatory capture, GLM 5.2, and open source… what happens when spend on AI goes from ‘experimental budgets’ to actual deployment with ROI conversations… and t...


SWL Week in Review - The Voice of America

MORE OR LESS — THE AMERICAN INTERNET We talk about how great America is… the need for a validated ‘American’ internet for civic discourse, Taylor and Travis, and Foiling… I spend a bunch of time discussing my 250th birthday gift to America… Vox Americanus — because I am pretty sick of waiting for m...


SWL Week in Review - Late Empire

MORE OR LESS POD Talking about smart glasses, the phone I dropped off a mountain (and how it is impossible to recover your phone number if you do ATT sim-swapping defense 2FA with… your phone (as their system works), The prediction markets / how to get women to participate in prediction markets, an...


SWL Week in Review - Teamshares

LESS & LESS POD Jessica and I did a 1:1 for this week’s pod. We talk ‘it’s valuable because it is valuable’ … Benchmarking Cursor’s acquisition vs. WhatsApp… The Brilliance of the ‘Fable’ Marketing by Anthropic… Corporate Narratives & why Elon is so good at what he actually does as a Marketer, Fina...


From the Podcast

I just registered agenttreatyframework.com. Do we get the .ai?

— Sam Lessin, More or Less Ep 170

So I think one of the most interesting points I saw from two managers is, these are ones who are way, way, way up on, like, AI stocks or AI Microns of the world, and I think they're all struggling with, like, what's the Main Street application of AI, 'cause AI is so hated by Main Street and by normal people. And the ones who are bulled up on it, the basic narrative is Main Street says they hate it, but then if you actually show it to them and use it, they love it. And so, like, it's, like, there's this whole gap around, like, perception versus the real- the narrative versus the reality of it, and, like, so-and-so's small town store has been around for 100 years You know, then you show them how to redesign the store with AI, and their mind is blown, and they're super psyched about it. You know what I mean? And so like there, there's like a whole narrative about like, okay, what's the real story on how people feel about this stuff, and what's, like, story versus narrative? I thought that was somewhat interesting, et cetera.

— Sam Lessin, More or Less Ep 170

Well, okay, if we really wanted to make it into a business, a money-making scheme, you come up with, as Dave said, the agent treaty framework, and then you basically would want some sort of, like, treaty platform, right? Where like, okay, we're gonna sign a treaty, and, like, you can have treaty lawyer bots. We're gonna have, like, a meeting place where you can put up, okay, I'm willing to do treaties.

— Sam Lessin, More or Less Ep 170

Standards exist in a world where you need standards because you can't do a bunch of one-off deals. It's too complicated, right? It's too much work. So you have the standard and you write to the standard, right? Fine. We don't need that shit anymore. Now, like, with AI, everything can be a pairwise t- treaty, negotiated truces, right? And so everything becomes the agent treaty framework.

— Sam Lessin, More or Less Ep 170

Well, and the funny thing is, is with the agents, I wonder if you can run long tail BD so much faster. Uh, the part of the problem with BD is just, like, it's time-consuming. Like, Amazon's clearly, it's worth doing a business deal with Amazon. Do you think in the future, Dave, like, these micro agents basically go out and negotiate deals more dynamically using, like, AI, like, at scale?

— Sam Lessin, More or Less Ep 170

But on the other hand, it's like, here's the thing. It's just an interesting business problem because, like, what ChatGPT originally s- uh, what ChatGPT originally said is, "Oh, put yourself inside us." You know what I mean? Like, "We'll effectively literally front end you," or, "Give us specific APIs that will let us do this to make it easier." Pri- companies have been trying this forever, right? Which is like, "Hey, we should be partners. Give us the APIs, we'll sit on top."

— Sam Lessin, More or Less Ep 170

But, like, hotels, like the Hilton, for instance. This is my, my example last night. I went to Muse and said, "Hey, I need a hotel room. I have an early morning flight out of LAX." I don't care.

— Sam Lessin, More or Less Ep 170

Oh, I thought you were gonna say something different, which I have a half-written essay on, is that actually the, the fact that Facebook Connect ultimately didn't work and Open Graph failed and had to be shut down is the same story, where, like, there's not enough value trade for the brands.

— Sam Lessin, More or Less Ep 170

But people don't... The thing I don't understand about, like, the s- the standard doesn't change anything. Like, it's either simple. It's like, as a business, you're either gonna be able to say, "Well, I literally cannot stop people from crawling me or taking my stuff." That's what happened with, like, the textual internet and why we even have AI, is they basically just, like, Carmen Sandiego stole the entire internet to bootstrap these things, right? Like-

— Sam Lessin, More or Less Ep 170

Because everything, it's just an API. These things can read APIs and documentation. It doesn't matter whether it's MCP or not. It's just ways for machines to talk to machines, right? And so for me, it's when people are like, "Oh, we have new standards, da, da, da," it's actually a very simple thing. It's like either your machine or a service you have has an API in some way, shape, or form, which Dave was pointing out a year ago, even if you don't publish it, I can reverse engineer it now, right? Either it is accessible to other machines, in which case it will be used by other machines, or it is not, in which case you can have something that is protected. And so the entire thing, like these standards and protocols, is all bullshit. What is interesting, though, is, like, I don't know about you guys, I've already noticed from Muse, for instance, Facebook's thing, that certain workflows that used to work have already been turned off, right? Because servers are like-

— Sam Lessin, More or Less Ep 170

All these things, right? And, like, that's actually f- as wild as it is, fairly practical. The funny thing about that is we could do something about that. Like, it's not that hard to think about what the US liability framework could be. Like, think about post '08, we had to have cash reserves, whether it's you have to carry a lot of insurance, 'cause if you're doing lab research, then things might get out, but you don't have the balance sheet to pay for it. You can't dump that risk on the US government or the US people. Like, you should pay for that, right? So because we're so obsessed with the tales of zero and infinity and the religion, we're missing actually good decisions in business about how to operate in a new technological landscape. And, like, I think that's the thing is like, to me is like, religion is super fascinating.

— Sam Lessin, More or Less Ep 170

Agreed. But then it kind of, the crypto thinking plus a lot of the stuff br- came into the AI story. Now you have these two interesting infinities and zeros. Infinity and zero-one was like the Sam Altman original pitch, which is we will own everything. Whoever gets the AGI first owns infinity. There are no more businesses except for us, and it can only go to zero, right? And so you're like, "Okay, well, the average of infinity and zero is still infinity, so I guess we should invest in this. Who cares what the price is? Who cares how much capital it needs?" Like that was infection one. Now we have the inverse going on, which I think is to be taken very seriously, which is it might be that, it's actually not, and like that was a silly narrative when you think about it, but people believed it enough.

— Sam Lessin, More or Less Ep 170

The tails like meaning the extreme, like zero or infinity, like the tails of numbers.

— Sam Lessin, More or Less Ep 170

It's an awesome book, and it's an important one to internalize, I think it talk about what Silicon Valley's business model is and, and kind of where we are. The basic point of the book is that if you go all the way back to like the time of the Greeks and before, the idea of true zero, right, was like highly fought. And so like the, the first historical vignette is the Pythagoreans who wanted to kind of introduce the idea of true nothingness. This is like kind of like creation ex nihilo from the Bible. How do you like create something from nothing? These are very deep philosophical problems, and the West hated it because it's really hard to reason about, and it's really hard to talk about consistent growth and like the things we're good at. Same thing with like infinity, like infinity is a weird concept. Because of that, the zero came from India. The West fought it like hell. The only reason it exists in Western culture is it is just too useful, like you need zero. Like the traders made it happen. The church fought it like holy hell to like keep it out of Western culture. But like fast-forward, if you think about like our markets and the way we build businesses, and we think about competition and compounding and all those sorts of things, they're great at like most normal modeling in numbers that we're familiar with, what we can argue about and multiply, da da da. The second you introduce a zero or an infinity anywhere in the chain, you break everything because the tail, which is infinity or zero, dominates the whole story, right? And what's really interesting, I think, is in some ways, if you look at the story that we've seen in the last many years in Silicon Valley, the tendency towards infinity, which you saw the, the geometric returns on Google and Facebook and oh my God, the world is infinitely large and we can dominate the whole thing, started this. Things like Bitcoin, which is like, oh my God, if everyone believes, then belief is self-perpetuating and it can be in- infinitely valuable, right? And it can only be zero. Then you see like GameStop and like this whole series of things. I think there is this... In fact, in some ways, like the tails infected the entire narrative of Silicon Valley, right? And so that's why we get to the today's-

— Sam Lessin, More or Less Ep 170

Although it's a recent phenomenon, right? Because like even as far as ten, 15 years ago, the businesses that Silicon Valley generated were like unbelievably capitalistic. You know what I mean? Like it wasn't about like moving heavy dollars. Like that's kind of a recent Bitcoin style. There's a series of things. I, I honestly think a lot of like what's gone on has been people learning the wrong lessons from like Bitcoin and religion effectively in this era, right? Where if you think about like this dynamic, it's like you had the era of Google and Facebook, which everyone got wrong from like a storytelling perspective, largely because like, well, how big could they possibly... Even I got this wrong. Like I was like, what is the thing that is more than a hundred billion dollar company? That's unfathomably large in historical context. And so people got, "Oh my God, things can be huge." Then Bitcoin, which again, I was early on, you know, Dave, you were too, and like then Ripple and Solana and like all this stuff taught people the lesson of like effectively the aver-- which I love this line, 'cause it's true, which is the average of zero to infinity is infinity, which is like-

— Sam Lessin, More or Less Ep 170

Tweets

You mathmatically can't compound your way to wealth anymore... 20 years, 7% returns, 3% inflation, 40% taxes -- best case you 1.5x your investment. That is why the kids YOLO it... plain and simple. https://t.co/ceHLAqjBdk

November 28, 2025 · 18486 likes · link

I really don't understand how Spotify doesn't yet have an LLM mode where I can describe a mood, etc. and it generates a playlist for me. Seems unbelievably obvious value add.

March 29, 2025 · 11366 likes · link

Tech founders buying houses in Maimi is kinda like that era when Goldman Sachs kept an entire building fully setup and ready to go at all times in Jersey City across the river to remind NYC to not over-tax them.

January 09, 2026 · 6819 likes · link

For some reason @Harvard has taken down Dean Gay's statement on the death of George Floyd from its original source.... but I think it is worth reflecting on today, and juxtaposing her words then with what she said today when questioned about hate speech towards Jews on campus and… https://t.co/tAaPoNWbum

December 06, 2023 · 6234 likes · link

Most successful creator of manual slop worried about AI slop... which seems correct. but non-issue for non-slop creators. https://t.co/ZACQw6M9e6

October 06, 2025 · 5848 likes · link

The coming fall of the Kardashians in context of how entertainment is evolving... (aka why they are so pissed about tiktok) https://t.co/wtYrvxbS35

July 26, 2022 · 2682 likes · link

The Year is 2027, China Has Invaded Taiwan.. and American kids are holding anti-war pro-China rallies in the streets of the US … all because of TikTok https://t.co/4GQtIBBQig

November 15, 2023 · 2330 likes · link

Required Reading for All VC Jobs — You Will Fail at Capitalism if You Haven’t Digested This Media https://t.co/5ehBL1L95c

March 21, 2025 · 2307 likes · link

There are two jewish heads of state in the entire world - Zelensky and Netanyahu... it says something that they are leading the two nations defending western liberalism in global proxy wars... against deeply illiberal regimes.

November 05, 2023 · 1848 likes · link

It is nearly impossible to convince a VC of a thesis they don’t already believe, so the key in fundraising is to ‘discover’ the right partners, not try to educate and convince… https://t.co/t91w1Y1pPQ

August 05, 2022 · 1780 likes · link

Taxing Billionaires’ Unrealized Gains is Disgraceful ... https://t.co/sDtZcYoyIH

October 24, 2021 · 1549 likes · link

The jelly jelly coin is live... making the internet fun again... https://t.co/GNZ2Lxnumq https://t.co/Kc6z3JL6tE

January 29, 2025 · 1495 likes · link

A bunch of people have written me back saying this was the best newsletter I have ever sent (flattering) ... so here it is for those who don't subscribe: AI Is Not a Labor Crisis. It Is a Meaning Crisis. https://t.co/usOWCPUFtO

April 12, 2026 · 1378 likes · link

This is the problem with the NYT losing so much trust in their journalism / neutrality. A jewish man is killed at a pro- palastian demonstration after being struck in the head by a megaphone by a pro Palestinian protester -- the NYT just skips that part .... The NYT OMITS… https://t.co/f7LmZaiQS0

November 07, 2023 · 1326 likes · link

I really don’t understand why people hate on email so much... I feel like it is nearly perfect communication medium for actually getting things done. Asynch, triage-able, seach, forces process discipline, open platform, etc

October 17, 2019 · 1305 likes · link

The thing Bernie misses? With taxes in CA the public already does get 50% of Anthropic and OpenAI...

June 02, 2026 · 1163 likes · link

OMG. vaporfly is the most impressive tech i have experienced in years. period. forget LLMs. mind blown. https://t.co/ol4lKb6iy3

April 14, 2023 · 1140 likes · link

shame on the @nytimes -- huge journalistic failure. Someone should lose their job over this. https://t.co/vRxUTIqYhC

October 17, 2023 · 1087 likes · link

I am legit curious what will happen to tech culture if this LK-99 thing plays out and the entire GPU supply pivots to be only focused on fusion power plants, space rail guns, and batteries instead of whatever stupid applications startups are working on now.

August 03, 2023 · 1068 likes · link

Is @elonmusk's relationship with twitter that different than tesla in his own mind? sure he owns more of tesla (17% vs 9%) but not dramatically. in both cases he comes in non-founder investor, & then leads by making a bunch of product oriented claims on the internet ;)

April 10, 2022 · 1029 likes · link