Sam Lessin's takes on AI, machine learning, LLMs, and the transformation of technology — drawn from his writing, tweets, and podcast.
From the Podcast
This is the question is, look, there's a lot of ways in which Apple actually will come out of this era looking good Hilariously good. They didn't sink all the money into data centers, right? They're gonna do it on t- they're gonna get to sit on top of every model as the last model to consumers, they can maintain that. It's very possible in 10 years that Apple is laughing all the way to the bank, and people will be blessing Tim Cook for having done, fallen into none of the traps. Didn't big a- build a big research team, didn't do data centers, didn't get snowed. Like, then people will be a hero. If that's not true, right, and it turns out that Apple is internally dysfunctional, can't get AI stuff done, blah, all the negative stories, then the story will be Tim spent the last 15 years optimizing last year's game. It's classic innovator's dilemma. He missed the big swerve, and he's gonna be vilified. But we won't know for 10 years.
— Sam Lessin, More or Less Ep 164
I do think, Dave, the thing I think you and I can agree on is we're gonna look back in 10 years, and Tim Cook is either gonna look like a fucking genius or an idiot, and Apple will either be a really important company or have completely missed an era. And, like, we don't know yet. I think his legacy will be defined by the AI, what comes next.
— Sam Lessin, More or Less Ep 164
Did you see with no AI with Claymation? People were panning that on the internet. Well, the whole commercial for it is a bunch of Claymation, which is very fun and cool, but, like, how do you not use AI in a product that is fundamentally about AI?
— Sam Lessin, More or Less Ep 164
This is my being really cynical, snarky, but the cynical, snarky take is, in about 15 years, you can supply chain optimize the hell out of a company and make stock go way up, but then Apple better figure out how to not be Nike, right, and come up with the innovations and stay ahead of the market, because literally it's almost, like, to the month. This chart implies he's leaving Apple at the maximum price possible for a Tim Cook style optimizer. But it's obviously just a silly chart, but it is funny to look at.
— Sam Lessin, More or Less Ep 164
I'm very proud of this. I said, "Hey, Claude. I want a chart that basically talks on a, obviously a zero, a percentile basis, so you can baseline it, when Tim Cook became in charge of Apple and when he joined the board of Nike, and the market cap of the two." And it's hilarious, because he joined Nike five years as a board director before he became the head of Apple. And if you look at the charts, for the first 15 years or whatever it is, 15 and change, which is the, the time I said, that is literally Nike's maximum stock price, and it is now back down to basically where he started. And so it's really funny. If you look at the chart, which I will post a link to if I remember-
— Sam Lessin, More or Less Ep 164
Even iMessage. Like, take iMessage. Like, they have all these fucking controls. Who can talk to your teen? It's too much. But if you said to me... And, like, by the way, you know what I have? I have a desktop, like, sitting in my compu- in my room where I just, like, logged into my son's iMessage account, and I sit there and fucking screenshot it all day long algorithmically, 'cause there's no APIs to it, so I can process, like, what he's talking about and who he's talking to as a parent, right? Like, that's insane. It should be really easy to just be like, I get CC'd easily. And by the way, this is beautiful in the agentic world, because in an agentic... Before it'd be like, that's really hard to review all that stuff. I don't wanna, like, click on everything. Now you're like, look, I can just run Claude on it and just care, these are my values. What should I care about? Things like that. But you can just be so much smarter about the product decisions and, like, policy-wise what you're actually shooting for in a way that, like, enables parents and helps people, right? And people aren't.
— Sam Lessin, More or Less Ep 164
Then you're like, okay, this is a rule for everyone. This isn't just for Instagram. It's like, look, yeah, kid, do what you're gonna do on Instagram, but I get to see everything you're looking at and clicking on. Watch what you're gonna watch on YouTube for now, but I want the log of it really easy to access. And then the obvious next step is I wanna be able to have a conversation with you about it. In theory, I wanna be able to block you from channels in the future. But if you said to me, "Hey, until you're 18, I'm not gonna, like, limit your screen time," that's stupid. I'm not gonna, like, try to come up with these nettling rules. It's a very, very simple concept. Simple, low level. If you're looking at shit on your phone, until you're 18, I have an easy way to sidecar.
— Sam Lessin, More or Less Ep 164
I think this is good. Can I embrace and extend? So one, interestingly, I think if you gave everyone, you said, "All your software is now customizable," the humans will be like, "More boobs." Customizable software is not gonna be, lead to restraint. The people are gonna be like, "I want more powerful marijuana strains." Like, they don't want less powerful shit, right? And so, like-
— Sam Lessin, More or Less Ep 164
No one wins, but everyone gets to go to their constituents. It's kind of like, how the hell do you get out of Ukraine or Hormuz? You need, everyone needs to be able to claim a win and then realize we probably shouldn't have gotten into this fight in the first place. It, or like the way we set it up was wrong. And I just think, like, I wish that we could have real conversations. And I actually appreciate Meta at least being like, "Look, we'll do what we need to do to, like, give you a win. Like, let's move on. We're happy to do some things, whatever." But also opening the door and being like, "Hey, let's like... If you wanna have more real conversation, we're down for it. But like let's do it in like a actually sensible, logical way, as opposed to this being like a selective enforcement game of politics." It's like you're fighting last generation's war.
— Sam Lessin, More or Less Ep 164
Like, we can talk about liberty and, like, the extents of it and, like, things like that. I think those are all really interesting conversations. Well, we can't really have a intellectual or big picture conversation about this or AI. So instead we're gonna look for, like, reasonably easy targets and then selectively ask them for some money and some changes, is just that good. 'Cause I don't think it does anything. I think it's all theater. Like, you started out by saying it's a nothing burger, Dave, like, in terms of a slap on the wrist. I'd say it's a nothing burger for actually helping anything.
— Sam Lessin, More or Less Ep 164
I have figured out, by the way, you can't talk about certain things on our podcast or av- YouTube won't let you promote it.
— Sam Lessin, More or Less Ep 164
It's not. But let's just acknowledge we are, and, like, that's the conversation nationally. And you're not going after the everything apples to apples. And so I think Meta's making a really good point, which is like, look, if we as a society wanna make a decision at a national level that we believe that kids should only do an hour of screen time a day in similar services, fine. Then, like, we can all agree to that, but selectively going after one provider and not the others, like, I think it's actually a very brilliant thing, being like, "Look, we're gonna do part of it be- because we wanna settle with you guys. We wanna move on from this. Candidly, we wanna be an AI company. Like, let's be done with this. But, like, we're happy to give more money, go even more extreme. You guys actually have the legal horsepower, and society believes that we should only have kids do an hour a day. Fine"
— Sam Lessin, More or Less Ep 164
I don't know. I, I honestly think this is a totally logical conclusion for everyone. My sense is Meta probably, like everyone, there's, like, a bunch of emails you just don't want out 'cause, like, that's how these things work. You gotta settle. You gotta give them a pound of flesh.
— Sam Lessin, More or Less Ep 164
What would have become of poor you and me without Ain- AOL Instant Messenger back in the day?
— Sam Lessin, More or Less Ep 164
Guys, I gotta tell you, listen, the email agent thing, I was on with an entrepreneur, actually two in the last week, and he's like, "Well, I have, like, the... I call the agent, and I text the agent." And I was like, "Yeah, but email's by far the best," and he's like, "Yeah, it is." Email's sick. The multithreading of it is so good, right? I don't know. Anyone who's texting with their agent doesn't get it.
— Sam Lessin, More or Less Ep 164
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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Taxing Billionaires’ Unrealized Gains is Disgraceful ... https://t.co/sDtZcYoyIH
October 24, 2021
· 1549 likes
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The jelly jelly coin is live... making the internet fun again... https://t.co/GNZ2Lxnumq https://t.co/Kc6z3JL6tE
January 29, 2025
· 1495 likes
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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
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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
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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
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The thing Bernie misses? With taxes in CA the public already does get 50% of Anthropic and OpenAI...
June 02, 2026
· 1163 likes
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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
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shame on the @nytimes -- huge journalistic failure. Someone should lose their job over this. https://t.co/vRxUTIqYhC
October 17, 2023
· 1087 likes
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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
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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
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