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Sam Lessin on Media & Content

Sam Lessin's views on media, journalism, newsletters, content creation, and the future of information — as a columnist at The Information.

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...


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...


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 - clawdbot

More Or Less — Clawdbot & the Personal Security Apocalypse Clawdbot is incredible. It’s also the moment you should immediately realize: this is how it ends. Local permissions to your drive, screen, and windows are the cleanest on-ramp imaginable to a locked-down internet, hardened enclaves, an...


SWL Week in Review - Positivity?

More or Less - A Touch Of Optimism? Thanks to all the folks who felt necessary to message back about my downer email last week… all the media people were like ‘yah this sounds right’ and all the investors were like ‘stop being a bummer’ for what that is worth… this weeks MOL / week 1 of 2026 we are...


SWL Week in Review - The Narratives of ’26

So what are the themes of the year that actually matter? The stories we tell ourselves about the world have always mattered a great deal… but we live in a particularly strong moment of narrative power and narrative instability. Fundamentally this is all because of the internet -- a new human superp...


SWL Week in Review - Whip not Muscle

More or Less — Predictions for 2026 We grade ourselves on our 2025 predictions and talk 2026… upshot — we did ‘ok’ on 2025, on 2026 we have a few you can actually hold us accountable for & a bunch you probably can’t. 2025 Predictions: Bitcoin Price, Solana ETFs, Crypto Regulation, Amazon Marketpl...


SWL Week in Review - Enemy of My Enemy

More or Less - Media Wars, 1010 Billboard Index, and Narrative Flywheel Fun MOL this week … ideas that really stuck with me from the conversation were around understanding 2025 entrepreneurial journey as planting a flag, building a team, and then positioning yourself to be able to ‘pivot into the n...


SWL Week in Review - Code Red Realities

More or Less — Code Red Realities We start non-Ai with an ode to Daniel Lurie’s social media game (excellent…) — and then go deep discussing OpenAI ‘code red’ realities… When the leader says ‘hard left’ but then can only shake free 5 engineers, how hard it is to hard pivot a bunch of expensive desi...


SWL Week in Review - Finger Size

More or Less - Wearables and Finger Size We discuss lots of angles on wearables… rings, earrings, glasses, and more…. Also somehow we have reversed roles and I am the one defending Apple??? Again. Checkins on ettiequte, mini-defense tanks, and more… Hot Takes Meta Etiquette — I just love how thi...


From the Podcast

Well, this guy emailed me. This is definitely getting paid for. This is actually very exciting, guys. I have a first ever on air ad. Someone wrote me back on my newsletter and had this whole thing and he said, Sam, I want to advertise on your podcast. So you ready? This is our ad. It's from getvictor.com.

— Sam Lessin, More or Less Ep 139

They should buy OpenAI. It's like she's immediately buying, I'm sorry, she's immediately buying Snap to put buttons in

— Sam Lessin, More or Less Ep 97

I don't know, was like a first attempt. It was an early attempt at media and marketing and mass market.

— Sam Lessin, More or Less Ep 91

Well, I think the difference is, like, well, first of all, I think there's a big difference between apologizing. I think there's a big difference between apologizing for like product versus apologizing for content and marketing. Like I just think those like very different veins. Well, that was hilarious. That was social media is chairs.

— Sam Lessin, More or Less Ep 91

And I love Raj. He's a dear friend. But he's kind of the business guy. totally is the hardcore genius. And totally is amazing. And he put out this thing being like, this was a mistake and the whole night. I was like, wow, that's great. This might be the 201 media strategy, which is, you know, 2025 101 PR crisis comms is like, never ever ever apologize for anything. Right? 201 might be if you apologize the right way. That's actually probably better. So credit to totally but it was a wild moment.

— Sam Lessin, More or Less Ep 91

Well, it's they took it down, which I actually was the right everyone's like, why do you I was like, actually, think it's exactly initially I saying you can't in 2025 apologize. Like it's the PR 101 is you do not apologize. So you just take it down and you move on, which I think was the right move because it was clearly an incredibly stupid piece of media. Now I will say Anatoly who's awesome today actually put out a tweet. He's he's the technical founder. He's like the fact that the guy the genius behind Solana it's like Raj and Anatoly.

— Sam Lessin, More or Less Ep 91

It was, and it's like the sentiment on it is actually not, mean, I don't agree with everything. There's a lot I agree with. Um, but the funny thing is, is like, completely missed the media memo on this because it's exactly to a message that if like Roger Anatoly, both of them are great, had like gotten up or one of the leaders and said, is what I believe. I authentically believe this. I stand behind it. It actually would have been basically fine. Like, but instead they like did the opposite, which is the, it's the, in comms hired actors.

— Sam Lessin, More or Less Ep 91

right of youth attention and belief and etc. That would be the bold statement of being like, this is just not a thing we want anymore. We clearly are like not in that zone. We're in some zone of some weird ass deal making right for slices of whatever and infrastructure and blah, blah, blah. And then your eyes just glaze over. And by the way, this is not a bad media strategy, right? Which is like you just throw everything against the wall. And then people like me get bored in the details, right? Because it's like

— Sam Lessin, More or Less Ep 90

It's like, which narrative do you want to pay attention to? Look, Larry Ellison owning TikTok would be hilarious, which kind of makes me think it would happen. Because like, think the guy has no, I've never seen him on social media, let alone dancing.

— Sam Lessin, More or Less Ep 90

Because you're in the media business and people want to read about it, because the morons want to read about it and they'll pay you for it, so sure.

— Sam Lessin, More or Less Ep 90

The thing I don't understand is that when you, you're the only person who uses Lyft, like you are a hundred percent of Lyft's business. And so, but you're a very good customer. And the thing I don't understand is that, that none of the hedge fund bots immediately respond to this news and just short of the, you know, Lyft is only down 50 % on the year. Cause like, and it should be down a hundred percent because you're like their only customer and you're going to have no use for them soon.

— Sam Lessin, More or Less Ep 90

Well, it's Well, but the thing I keep in mind is again, like the question is whether it's a cost or value. Because the thing that the social media does is it monetizes like waiting in lines. It monetizes like, people are less angry at the airport because of TikTok, right? Because they just sit in their fucking seats and like doom scroll and then they're like not angry about the time wasted. Whereas the interesting thing about going to a sporting event is you're investing not only the money, but a shit ton of like solid block time, which is very expensive, right? So in some ways it has to pay for the amount of time.

— Sam Lessin, More or Less Ep 89

Maybe. It did suck immediately back out. Right. So it really was a one time Trump make rich. But I would say that I don't know. think like the thing that's gonna happen is you can it's not like the type of thing you can just play that game over and over and over. I think you need like escalating seriousness for anyone to care. like Trump make the next tweet from Trump will have if this Trump if this one moved Cardano 40 % because no one thought it was an important thing. And it's not but it happens to be heavily traded and whatever like next time we'll have half the effect.

— Sam Lessin, More or Less Ep 89

Which again, in the spectrum of social media and internet scale, these are very small numbers.

— Sam Lessin, More or Less Ep 89

Well, I'll give you another again, which is I was at one of these many conferences this week, media conference with Muckety Mucks. That's what I do at ski conferences this time of year. But there's always a really good quiz in it. And I have to say, my team, was very upset. We were one question away from winning the quiz. I'm very upset that we did not win the quiz. We lost on an easy question.

— Sam Lessin, More or Less Ep 89

Tweets

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

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

1/ People who believe in 'citizen journalism' fundamentally don't understand is that the 'cost' of real information is very high. Finding new facts, and validating their truth, and carrying liability is structurally much more costly than citizens can afford alone.

July 10, 2020 · 995 likes · link

The US has a ban on foreign owned media for very valid national security reasons... if it wasn't clear before, it should be crystal clear now that there should be no loophole in that for "social" media -- this is a critical national security issue / not about politics. https://t.co/TUASomq3C1

October 25, 2023 · 701 likes · link

Why Micro-Payments for Journalism Don’t Work (Crypto or Otherwise)… https://t.co/OiDZaphGFs

August 16, 2021 · 620 likes · link

This is important to watch and understand is not at all isolated. media matters. The messages you give your kids ends up being destiny - and there is a very clear right and wrong here. https://t.co/yieoKIbA1S

December 15, 2023 · 210 likes · link

5/ So, yes, punditry - is indeed getting cheaper and cheaper & more ubiquitous. Today, content and commentary are truly the domain of individual citizens. Just don't confuse that with actual journalism / fact finding, which isn't gonna come from 'citizens'.

July 10, 2020 · 205 likes · link

So Jack Leaves Twitter... Twitter immediately commits to content moderation and Square immediately rebrands as a crypto-style .xyz -- in 2021 this makes 100% sense, i know where i would want to spend time ...

December 01, 2021 · 187 likes · link

6/ The challenge today is that with distribution costs at zero, punditry is nearly free to produce end-to-end but real information / journalism is still v expensive. This creates huge business pressure towards more high-margin punditry and less journalism / fact finding.

July 10, 2020 · 184 likes · link

look the obvious answer is accept the jet, immediately sell it and use cash to pay down the federal deficit....

May 13, 2025 · 164 likes · link

authenticity on social media... https://t.co/3ZwpZGJV6a

February 01, 2025 · 151 likes · link

This is hilarious -- Florida imposes fines on media companies for blocking speech / banning accounts... unless they have a theme park. https://t.co/LVLyeQ9iFl

May 24, 2021 · 132 likes · link

@bradrobertson the difference is that everyone understands social media to be untrustworthy, we need institutions like the NYT to represent a higher standard of trust, because if they are just social media as well, we are in a world of pain as a democracy

November 07, 2023 · 127 likes · link

Been playing with gpt-summarizing all the newsletters I get and then getting one 'meta-overview' daily ... https://t.co/6NoIJKsZoL if you want to play along https://t.co/GViVMcggWm

July 02, 2024 · 97 likes · link

@NickADobos not at all - we literally do not allow legally foreign ownership of media companies without a special waver, which tiktok does not have. You can say whatever you want ... just use a platform not controlled by foreigners.

October 30, 2023 · 93 likes · link

I have said it before & will say it again, when Softbank buys, you need to figure out how to sell immediately. We have a handful of seed investments left alive that I like still in the portfolio where SB came in later. I really hope it doesn't turn out to be a 100% kill rate :( https://t.co/7RlGBEDwDL

July 18, 2023 · 81 likes · link

Non-tenure track Harvard faculty just voted to organize under the United Auto Workers... if this were a private company the correct response would be to eliminate all non-tenure faculty positions immediately. back in reality that won't happen and this does not bode well. https://t.co/4yMQd28IA1

April 06, 2024 · 79 likes · link

On @a16z 's New Publication & Why The Modern Media Seems So Adversarial… https://t.co/SD9y2stYnu

January 21, 2021 · 79 likes · link

@scottiev not mentioning at all what the LA times is reporting as well as many many other sources, skipping the investigates as homesite part etc - actually is... unless they are 100% sure they are right and know what happened (and then they should mention and refute) - that is journalism

November 07, 2023 · 68 likes · link

When will the ridiculous scapegoating of social media stop working as a political tactic? https://t.co/28ns196SfF

July 17, 2021 · 66 likes · link