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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 - AI Flippenings & 2x2s

More or Less Podcast — Flippenings OpenAI gets passed in revenue (and valuation) by Anthropic, Google might now eclipse Nvidia on market cap./ is within a breath… a moment of AI flippenings is upon us & the real story isn’t the vying for first place, it is the fact that there is a race at all… bec...


Invite to Pearl genesis event

hey {{ customer.name | split: " " | first }}, I’ve been working on something I think you’ll find genuinely interesting: Pearl — a new protocol that turns AI compute into a native digital currency based on a recent mathematical breakthrough. You can read the foundational research here.... On Ma...


SWL Week in Review - WWE of Silicon Valley

More or Less — ‘Executive Chairman’ We riff on apple, Musk vs. Altman WWE ‘power fight’ (not a money fight)… UBI isn’t gonna solve much, cursor — Jensen’s ‘I didn’t wake up a loser’ stressy moment… my colonoscopy nurse hates AI, and more. HOT TAKES Narrative WWE Warfare When Story Matters More T...


Invite to Pearl genesis event

hey {{ customer.name | split: " " | first }}, I’ve been working on something I think you’ll find genuinely interesting: Pearl — a new protocol that turns AI compute into a native digital currency based on a recent mathematical breakthrough. You can read the foundational research here.... On Ma...


SWL Week in Review - Build Your Own Apps

More or Less — Who Can Afford to Pay Taxes?! We talk all birds, and a bunch about how the decision to sell / hold these big IPOs with huge markups has more to do with relative valuation than price because of taxes! Also I spent most of the episode locked out of my SF office (I don’t have a key) — a...


SWL Week in Review - AI Is Not a Labor Crisis. It Is a Meaning Crisis.

AI Is Not a Labor Crisis. It Is a Meaning Crisis. "Civilizations are not mainly threatened by discomfort; they are threatened by superfluity" People are worried about all sorts of things when it comes to AI… killer robots / AGI deciding to dispose of humanity (on purpose or by accident), a modern ...


SWL Week in Review - Looksmaxxing

More or Less Pod - AI Security Apocalypse For a while we have been gabbing about how AI completely breaks the business model of the internet / will end the internet by destroying how it makes money (the medium is the message… which is the business model) — but with all these inevitable AI security...


SWL Week in Review - Bot or Not

More or Less : Ladies Edition Dave and I went skiing… so the ladies invited some other non-sam-dave people on the podcast. Henrik and Ben on something called ?“donkeycorns”? … will watch it on the flight home because airplane wifi is actually starting to work (and yes, I 100% will pay more and choo...


SWL Week in Review - Master of Bots

More or Less - GTC & Claws Dave and Jess go on and on about GTC … shocker I didn’t go, but if Jensen wants to stop by the poorhouse and sauna for 3 hours he is more than welcome! Dave and I get into a pretty interesting discussion IMHO on ‘is Openclaw an OS’… what does an OS even mean / what is the...


SWL Week in Review - A Commodity Without Monopoly Power

More or Less — Dark Pools and Commodified Intelligence There is no question that developer demand more tokens… but do consumers? For what really? Is there any real margin in generic martix multiplication or is the market for ‘intelligence’ just the cost of power … and brutal competition in a world ...


SWL Week in Review - Claude Week

More or Less - Cutting Block Why aren’t the Silicon Valley engineers freaking out at Claude? Lack of union (like Hollywood)… or is freaking out admitting you are scared you aren’t good enough to be in the minority of engineers who will make more money vs. getting axed?! Also more on the ‘triangle t...


SWL Week in Review - Roblox for Adults

More or Less - Capitalism at Work Collapsing Margins to Zero We discuss Stripe / PayPal (the only question is regulatory / do collisions want to be in front of congress for years once administrations change over)… and spend a lot on this big question of what happens when building software goes the ...


SWL Week in Review - P90 selloff

More or Less: Urgent Care Jess made me stop podcasting and go to urgent care in the middle of the episode…. Because I thought I might have ‘dan corned’ myself after an epic run in the side country (I was fine)… but it means I missed most of the conversation — so I am as curious as you are as to wha...


SWL Week in Review - No Typists Anymore...

More or Less — In Everyone a Developer or No One A Developer? A great conversation between ski runs … on the future of open networks vs. closed / monolithic AI companies… in the future is ‘everyone a developer’ … or are there no developers and everyone just builds things (just like everyone types)…...


SWL Week in Review - Chosen by the Claw.

More or Less - Twitter Was Elon’s Ultimate Vibe Buy & Holy SpaceX The world is moving so fast this big news feels already old… but we break down more Elon world… The ‘vibe buy’ of X (remember when he tried to back out) as a HUGELY positive move for shaping the narrative through the elites & degens ...


From the Podcast

That's the key. Like, th- th- that is the key. Like, that's, you just explained the entire thing.

— Sam Lessin, More or Less Ep 157

Now, here's the funny thing, guys. This is, like, my personal take on this AI stuff and Fable. Pretty sophisticated user to this stuff. They're aboard, but, like, pretty sophisticated. I don't even care. Like, I actually literally don't know what Claude I'm using. I'm sure it's fine.

— Sam Lessin, More or Less Ep 157

I mean, I think, look, I was talking to one of our founders earlier who works on, uh, our MeritFirst testing platform. And, like, it is interesting how that, like, let's just drive hard on meritocracy, and, like, the best people should have it, open competition, et cetera, went from being kind of fringy to, like, completely mainstream. As part... I think we just have this, like, separation. We have, like, Mondami, nihilism, socialism, and then we have, like, a bunch of people that are in the minority numerically, but maybe not in terms of wealth and power, who are just like, "No, like, we want freedom, and capitalism, and meritocracy." Like, that's the trifecta. And so I just think that the world's very split, um, and that's what's making it super interesting. History says we're all about to get guillotined, but we'll, we'll find out.

— Sam Lessin, More or Less Ep 157

Yeah, like, that's the question of the year is, is there a compounding advantage against... I mean, it's ir- ironic, 'cause, like, Mark was all about open source early, right? And it, he, I think, is strategically right. It just turns out maybe to not be Meta's open source.

— Sam Lessin, More or Less Ep 157

They might be, but they might be, but for now at least, it feels like OpenAI is the weaker and the more distressed of the two, and that could just be narrative.

— Sam Lessin, More or Less Ep 157

But this is the point. This is why these are actually distressed companies, Dave. This is my point about, like, OpenAI's political play. We'll see what Anthropic does. These are, like, threatened-

— Sam Lessin, More or Less Ep 157

I mean, the easy point is, like, when it comes to technical platforms that are, like, they... I mean, are, you can kinda talk, you certainly can talk about Apple, but they also take most of the rents off of the App Store, right? At least used to, until they've been fight, fought out of it.

— Sam Lessin, More or Less Ep 157

I mean, I make tens of dollars. There are several people who have subscribed to my children's podcast that is all AI generated.

— Sam Lessin, More or Less Ep 157

Any capitalist enterprise that claims to be doing good or have a double bottom line is, like, always gonna be deeply suspect, right? Like, that's, like, the biggest trick the devil ever pulled.

— Sam Lessin, More or Less Ep 157

Here's the deal. It's super simple. It's like America loves capitalism. Why does it love capitalism? Well, we basically had this amazing immigrant punt for 200 years. We said, "Hey, come hang out over here, your most driven, most interesting people who wanna, like, make lives for themselves. And good news, we did the Louisiana Purchase. We got all this new land for you. Don't worry about the Indians. As long as you have a shovel and can work pretty hard, you can go west and make- do really well." You know, 20 acres and a mule style, right? And so that was great for a super long time. Then we got industrialized, and it worked again. Then in our generation, you wanna fast-forward, like, the internet was a huge boon for us because it was digital terra nova, right? That we could col- colonize, become important, get rich on, et cetera. And the problem is with each successive wave, the number of people, the number of humans you need to dig shit who can- and share the wealth goes down. It's like when you have- when you build a railroad, you need a fuckload of people. All those people get paid. When you build internet companies, you don't need as many people. Fewer people get paid. AI, you have even smaller teams. So the, the reality is, is like you have more wealth, but fewer humans who are dealt into it, right? And that is just, like, what is happening with technological leverage. And so there is... Like, I'm quite sympathetic to the fact, as much as I love capitalism and I'm hyper pro-capitalist, these proposals where it's like, oh, if only we change the tax code, there's, like, some massively... I don't think so. I think the only thing you can do is have a real meritocracy and say, "Look, it's not all gonna work out for everyone, but if you work really hard, you're gonna have a shot," right, is, like, the upshot. And, like, that is why I'm so obsessed with meritocracy and its combination to capitalism and, like, what, and freedom. It's like freedom, meritocracy, capitalism. Like, is- that's the trifecta, right, that we have to protect because the world is otherwise gonna get more unequal and more fucked. And the reality is when you start chipping at capitalism, you chip at freedom. And people are gonna do that if they feel like the, if the game is rigged or unfair, which is why Sam Altman trying to give 5% of the government, to the government for regulatory capture and all this politics is so bad, right? Because all of a sudden it makes the game not a fair and open game that at least you can play with rules. It becomes a game of politics where people feel gated out or gated in, and that is, like, the worst scenario for the long-term success of the country.

— Sam Lessin, More or Less Ep 157

Well, I hope that changes though. I actually like Trump accounts. I'll say it again.

— Sam Lessin, More or Less Ep 157

To inject cash to bail them out because they're important, right? And, like, this is funny because, like, there's no cash being proposed. There's no, there's no... But it is also, like, one of those things where, like, the only time we do this is for distressed situations. It's crazy for us to not do this. So they're, they're distressed. They're distressed.

— Sam Lessin, More or Less Ep 157

But they're ac- And, like, this is the thing, is, like, if you look at history, and people are really mad about this. Like, you know, go back to '08, people were like, "Let the banks fail." But, like, in history, there have been several episodes where, like, the US has taken stakes in companies, the government.

— Sam Lessin, More or Less Ep 157

Well, I do think, I do think the contrast of that versus the, you know, the, the, yet again, another uproar about Mackenzie Scott Bezos, right? And, like, people kind of being upset about how she's treated philanthropy is, like, quite interesting.

— Sam Lessin, More or Less Ep 157

Whatever it is, it's ridiculous. But the basic point is, like, I do actually have to give Sam Altman some credit, not as a business person, but as a politician, because I do think this is, if you're in his position, where one, you're trying to sell a commodity. You're, you're set up where you have to have premium prices on a commodity and you're screwed. And then two, even within the set of AI companies, let's pretend the polit- political winds shift where this becomes palpable and, like, gets done. Of course, Sam Altman's the one out promoting it because he's, he has the least to lose. He's not a real company like Google or Open- or, uh, Meta or someone where actually 5% is meaningful, and he's not even winning the pure AI race. Anthropic is. So if your competitors are gonna lose more by having to give up 5% of the government than you are, then, like, hog wild, right? So it is one of those things where, like, very cynically, I think it's a very, very smart strategery politics move, but the problem is-

— Sam Lessin, More or Less Ep 157

Tweets

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

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

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

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

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

Why you should be ‘default out’ on investing in ‘Generative AI’ companies for the next few years. https://t.co/FhFlJjLefZ

October 24, 2022 · 995 likes · link

AI will indeed spell the end of all human outbound sales jobs. NOT because AI "replaces" them, but instead because AI so poisons the well and no one responds to anything anymore.

November 03, 2024 · 987 likes · link

I can't wait for the South Park episode on all of this... https://t.co/AZtI4DwCTM

January 06, 2024 · 950 likes · link

We need to stop calling financing all software startups ‘venture capital’ when it is just plain old ‘private equity’... https://t.co/FTMybu2xf3

June 14, 2021 · 941 likes · link

Shameful AND a huge journalistic fail. We should assume the public web is going to be full of fake news, but when you can't even trust the times with headlines like these, we are really in trouble. https://t.co/D2RspZ3T70

October 17, 2023 · 876 likes · link