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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

Brit did not invite me to her big birthday bash. Or wait, or did you invite me but I didn't come?

— Sam Lessin, More or Less Ep 169

This is the thing that I think is interesting is in the spectrum of negativity, this is my, my, like, scoffing at the 10% kill all people thing. M- maybe there is some percentage truth. There's also- Aliens might show up, an asteroid might hit us. But this is at least far more practical and a real problem to talk about and deal with in the spectrum of how AI plays out. So if you wanna talk about negativity, while I agree it's very negative, it's a valid conversation. I think less negative than people who say like, "Oh, well, we can't care about anything in the middle or anything 'cause all that matters is, like, the edge case that we can't predict," right?

— Sam Lessin, More or Less Ep 169

The-- For that to happen, everything needs to crash. Right? Everyone, everyone's, like, pretending they're getting paid on the open. If it all crashes out and people get super hoardy... I mean, this is what's happening with networks. Like, I actually think one of the ironies of AI is it's very hard to take cold pitches as a VC now 'cause, uh, you're inundated with them. It's too easy to generate reasonably credible things. So what do you do? You lock down and only talk to your friend.

— Sam Lessin, More or Less Ep 169

This is-- But for what it's worth, though, this is, like, the other really negative dark future of AI, which is kind of like the Middle Ages version, where everyone effectively builds a castle and a moat and hoards. We end up in the Middle Ages 2.0 with these, like, sovereigns you-- that are, like, completely... You can't open it. You can't edit it. You have a car that's a black box that self-destructs if you touch anything. Like, it becomes really testy 'cause there's no other way to create moats, right?

— Sam Lessin, More or Less Ep 169

You are perfect. Oh, wait, only Sam's allowed to hit on you, my bad.

— Sam Lessin, More or Less Ep 169

But if so, then we're sitting in this, like, local blip. Because it's like you gotta project out. If you project out N years, like, almost certainly we all have neural links or equivalents, like, plugged into our brain. Like, we're only getting more and more connected and online. We're not certainly, like, moving away from that world anytime soon.

— Sam Lessin, More or Less Ep 169

Okay, so the never will be, so last part, here's the crazy part, and this is my third point. To your point, I think you're 100% right about this. The only way there ends up being lock-in somehow, right, is through BD, which is hilarious because it basically means that what it's gonna end up being is the world first all of a sudden all the engineers got overpaid. Right now we're in the place where all of effectively the political operatives are getting overpaid to try to deal with Washington, and ultimately it's gonna be, like, all the business teams getting overpaid to seal these deals. But, like, it's basically this, like, race-

— Sam Lessin, More or Less Ep 169

Right? So, like, now our printer is just, like, humming with, like, "Here come the daily reports." It's actually fabulous. Great idea, Jessica.

— Sam Lessin, More or Less Ep 169

And then built another one and sold it to OpenAI. Did you write him a check for the one he sold to OpenAI?

— Sam Lessin, More or Less Ep 169

Okay, guys, I got to tell you one floor as we were gonna do. So we're at-- Adrian, you know, we fly down to this secret conference, and we run into this, like, large institutional LP, and they're talking about h- very excitedly, they're actually an LP of ours, I quite like them, about how they're using AI to track their 14,000 private company positions, da, da, da, da.

— Sam Lessin, More or Less Ep 169

... Yeah. It's just, it's not a terrible thing to try, but the thing for me is, like, I keep going back to this fact. I use a lot of Claude. I think Claude's excellent. It's like the core of my infrastructure brain. But if I woke up tomorrow and Claude was gone, I would care for about one second, right? And, like, that is the fundamental baseline problem in the core business model, not necessarily unique data, wetlab, vertical integration, bogey, solve all cancer in a way others can't. Like, there are still option values on having this, but you gotta support a massive core infrastructure and cost structure, and the question is, is there a core business or not?

— Sam Lessin, More or Less Ep 169

The forward deploy thing actually weirdly, you know, you look at the Palantir or whatever, in a story of it's a security problem, it's an integration problem, it's hard to switch, it actually kind of makes sense for locking a bunch of people in. It's just a very different business model if it's like what we're doing forward deploy and what we're gonna get paid on is the tokens. But actually, the reality is, and this is my biggest thing-

— Sam Lessin, More or Less Ep 169

The thing that I think is just interesting is you look at these businesses, and you're like, generally speaking, these public companies, especially at this scale, there's like two things. You're investing in a core business- That has some properties that you believe in, and then you're buying option value on top, right? Which is there's six things that might happen to make them super valuable. I think the, the core anthropic business, which is can you sell premium tokens to people effectively? Like, can you sell it at a higher price than the open models because, like, what you're doing is so valuable? Like, the... And it- people will sink infinite amounts of money into marginally better tokens. That's the core business. It's been totally true for the last bunch of months. It's flat lining. Are there certain people that will pay infinitely forever for slightly marginally better tokens? Maybe. But, like, that's, like, the weakness of the core business is that whole conversation. And I think things like Muse, which again, can argue are not as advanced as Feeble, but are clearly sufficient for, like, what normal people need, right? Kind of put a dent in that story.

— Sam Lessin, More or Less Ep 169

Well, people are saying maybe four of inflation, four real. Like, there, there's some, like, people are arguing with the numbers. But, like, let's... It's a big number. It's a number much bigger than we've ever had in recent history. So DC needs it. The country in that way needs it, right? Silicon Valley's having a fucking party. And then New York weirdly really needs it too because New York is, like, this is, like, a huge financial engine for New York. Unlike historical tech situations where, look, you can't make that much money on Facebook or Google if you're in New York because they don't need that much money. It's, like, not your business. Now you need s- everything. Every insurance product, everyone's freaking having a party. And so the problem is when you say not, well, what happens if they don't work out? I'd flip it around and say, right now, if you did not have an AI story, we would be in, like, terribly dire straits.

— Sam Lessin, More or Less Ep 169

Or they figure out wet labs and vertically integrate and close down their services, and they're in a completely different business, and, like, whatever. But, like, it's weird. It's like SpaceX is, like, an option on 15 different businesses plus unique ro-rocket capabilities. These guys are, like, in a commoditization race for their core, where, like, again, if... And they are options on really great stories, but they're just stories.

— Sam Lessin, More or Less Ep 169

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