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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 - Warhound

MORE OR LESS — SpaceX / Tesla Merger, DUH — Shocker after Elon strapped Evel Knievel rocket boosters on a Hot Wheels car Epcot special and called it “flying” — Disney really should have allowed $50K reservations to be the first to have their own “people mover&rdqu...


SWL Week in Review - Nihilism

MORE OR LESS - When APIs become two way negotiations — Would you rather be right or rich? The question of the moment watching CoreWeave, all consumer agents being ‘good enough’, and the trajectory of Anthropic revenue. We have been discussing for YEARS now that AI is an extending innovation / compo...


SWL Week in Review - AI Treaties, Nathan Fielder, Agents (of Hollywood), and Grill Evals

MORE OR LESS — Agentic Commerce Discussion (obviously) — topic of the week… we get into how this will all play out on business and policy terms (now that the tech of give everyone a CPU in the cloud) is feeling solved…. Amazon vs. Meta, my inability to book the Hilton, etc. are all becoming the ques...


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...


From the Podcast

... that, like, you lose the fact that then there's hilarious videos of her saying absolutely batshit, just straight up lies all over the place, and the fact that she's probably mentally ill. The story's amazing. It's not about Elizabeth Holmes is my view. It's an incredible movie. Should definitely watch it.

— Sam Lessin, More or Less Ep 172

No, no, it's not the wealth tax threshold. That wouldn't work. But there's a thing which is, like, what Parker and, like, some people are really scared of, where, like, based on your voting control, you pay the wealth tax, which will bankrupt, like, the Google co-founders. I wonder if they f- came up with an interesting legal strategy to, like, maintain control while dealing with that problem.

— Sam Lessin, More or Less Ep 172

Half of the stock that I have in SpaceX is locked up. Maybe more, actually, probably 60%. It, there's an enormous cliff unlock coming in the spring, and everyone's gonna say, "You know, it's just supply and demand." If there's an enormous... You gotta, you gotta absorb that somewhere, right? If the enormous cliff, instead of being, like, 80% of the value or 50% of the value of all of SpaceX, is instead 30% of the value of SpaceX plus Tesla, right, because of how the shares go out, that is gonna be a easier pill to swallow, effectively, from a supply and demand perspective. You have all the retail Tesla investors and the denominator is just different. So that's my hot-off-the-press theory that I have not heard anyone say yet for why this merger makes sense right now. Pretty good.

— Sam Lessin, More or Less Ep 172

Unbelievable. I got a text notification, and it's like, "Hey, Sam. Here's a video walkthrough of our inspection," and it has the whole video transcribed of the whole car and all its parts. Then I get another text being like, "Hey, Sam. We noticed this car is in. Would you be interested in selling it to the dealership? Here's an offer." I was like, these guys are teched out in terms of, like, AI uses to, like, tech out a service station. These guys are living in the future of Mazda. I was very impressed.

— Sam Lessin, More or Less Ep 172

It was wild. Like, I get home, and, like, I'm waiting for them-

— Sam Lessin, More or Less Ep 172

So you guys might like this in terms of cybersecurity. This is kind of a fun one. About a year ago, I tweeted, which then became a seed company when someone decided to go do it, a fun AI era everything gets hacked idea, which is basically you can now pay a service to take your most important documents and photos and stick them in hard copy in a mine in like the North Pole. So that's your cybersecurity. You take your most important memories, documents, et cetera, and with this-

— Sam Lessin, More or Less Ep 172

It's kind of on the internet. What would happen, hypothetically, if you could secure a proof of work blockchain as the byproduct of matrix multiplication? Meaning you run your AI workloads, but you get a secure blockchain on top of that as more and more compute resources shift into that space. That's all I'll say for now. But number go up.

— Sam Lessin, More or Less Ep 172

For what it's worth, though, I think this is partially why there's been so many product issues building in the AI world. You remember, like, Dave, when we worked at Meta, which was called Facebook, and, like, we'd have all these features and things that didn't exist yet?

— Sam Lessin, More or Less Ep 172

Here's the funny thing about these leaks. It's the same thing where, like, there was rumors around town forever that OpenAI had, like, done all this, like, math research and was withholding it after the first paper announcement went so badly. The funny thing for me is, like, what is the backlog that's being held in private? It's basically zero days that now private companies are holding, and they're like, "Ooh, we shouldn't tell anyone about these." But the fact they have them and internally people know about them is kinda wild too, right?

— Sam Lessin, More or Less Ep 172

Well, I think, again, this comes down... It'll be an interesting question 'cause you'll see it, Jess, and you'll feel the art and the importance and decide whether it's the rare thing that is worth people just seeing.

— Sam Lessin, More or Less Ep 171

It's an everything app. To me, I'm kind of on the fence about it. Like, I, I really think that Jess is right. Historically, in a lot of categories, it's way easier to go de novo, especially when you have, like, humans and, like, all these p- like... But in certain things, like, there are just, like, dating... I actually backed this very small dating, agenticy dating startup, like, a year ago with a tiny angel check just to... It was a cool idea, and the... Getting traction's so difficult, right? And the reality is that, like-

— Sam Lessin, More or Less Ep 171

I've been pitched a few dating app mechanics I think are pretty innovative, and AI does help in certain interesting ways. I think it's a hard category.

— Sam Lessin, More or Less Ep 171

But Penelope's not interested in any of them. That's her whole thing. She's just waiting for Odysseus.

— Sam Lessin, More or Less Ep 171

No, I think it's, there's some debt in it. They gave some details on it. It, it's at least, I think, half debt.

— Sam Lessin, More or Less Ep 171

But that does matter for business. I just don't think you can dismiss it too much. Like, I think there is a cultural shift that will define a lot of how the world works going forward that's happening here. There'll be a reaction to it. Jess, for your sake and business readers, like, plenty of people will still believe in, like, a return of rationality and sanity and normalcy, and there'll always be a counterrevolution that'll be plenty big to support truth-seeking businesses. We kinda went from, like, oh wait, COVID. Now this AI super cycle of "it's gonna kill us all," like, I think it's all just, like, this sweep, right, of nothing matters, this is all wild, let's all gamble, and where are we going? And, like, by the way, maybe China loves this because they're like America is getting so culturally unhinged at the youth, that we're just gonna dominate it all. I think it's, like, really hard to miss the hallmarks here.

— Sam Lessin, More or Less Ep 171

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