The Wisdom Wall

326 quotable lessons, heuristics and mental models. Every one is playable at the moment it was said. No fortune cookies allowed.

Everyone Sam Lessin (326)Dave Morin (93)Jessica Lessin (31)Brit Morin (17)Elad Gil (11)Guillermo Rauch (8)Adrian Aoun (7)Julia Hartz (6)Aaron Levie (6)Vinod Khosla (5)Casey Neistat (5)Ben Smith (5)Mike Brown (4)Anatoly Yakovenko (4) Best Newest Oldest

“those number twos are always expendable. Um, they have to be.”

Sam Lessin, Oct 27, 2023

“when you get down to a lower level, because you can no longer have on-off APIs, because everything is scriptable, because these things can script any interface and interact anyway, as long as you have data sovereignty, meaning like it's your data, they're all completely interoperable. And like, there's nothing they can…”

Sam Lessin, Sep 4, 2026

“What matters is that no lead is secure. And projections don't mean anything, right? And so I think that's the real story is it's too easy to switch. Leads don't matter. It's going to be impossible to financially price any of this stuff.”

Sam Lessin, Aug 21, 2026

“The reason this never happens is because big fancy investors, not us lowly seed investors, but big fancy ones, have no interest in the write down, right? It's a massive write down, right, for them. And they'd rather just stick it on their books and pretend like it's worth something it's not until the last possible…”

Sam Lessin, Aug 7, 2026

“But, like, you taking any action as a single country does nothing, right? Like, and all it does is protect certain companies, right? And their, and their market caps.”

Sam Lessin, Jul 17, 2026

“And if the trailer is sick, then like, that means you have good taste, that means you have a story people are gonna care about, like, it means all the good things. And if your story is boring, or there's no good trailer, then your company's gonna suck.”

Sam Lessin, Jun 5, 2026

“To admit that you are worried about software taking your job as a software builder is to effectively say that you are a bad software engineer, right?”

Sam Lessin, Mar 6, 2026

“if you're a founder, software is no longer any sort of differentiator. Software is just like consumable. Like, it's just like, it's like a piece of media. Like, it's not like you can't build a software company.”

Sam Lessin, Jan 9, 2026

“I think when you get down to the practicality of how people use these things and their actual preferences or whatever, it just doesn't play out that way. It's not as much of a lock-in as you want it to be.”

Sam Lessin, Nov 28, 2025

“all of the people who are, you know, some version of like, how do I sell data or give data or give context to chat GPT and get paid cents on the dollar are stupid, right? And like, it should be exactly the way around, which is you just use them as commodity arms dealers for the business you already have and the…”

Sam Lessin, Oct 3, 2025

“there are all these smart people in teams that like follow this like incubatory, listen to your customer, customer research, like iterate, solve a problem for demo day. And what they don't realize is they're signing themselves up for like a decade of working on a problem. They don't give a Fuck about.”

Sam Lessin, Sep 12, 2025

“The problem is bankers are still just pricing based on what things are worth when they should be pricing based on, like, mimetic warfare and, like, community shit to get the bump and let the degens pay the price, right, for their silliness.”

Sam Lessin, Sep 12, 2025

“The entire thing with AI is it's a great way to sink money and power and compute into a war with itself that produces no value.”

Sam Lessin, Sep 6, 2025

“If you can't, like, build applications with AI to do your own job better, you just are not good at your job anymore.”

Sam Lessin, Jun 27, 2025

“you have to go back to human based networks, because you can't trust anything you see or anything you're sent from an unvalidated source, right? So you end up with a very Going back to a more structured society versus a more open society because of AI.”

Sam Lessin, Jun 27, 2025

“capitalism tends towards efficiency, but that's the whole beauty of it, but like requires structural inefficiency to profit, right? If there's no structural inefficiency, there's no profit, right? Which is why people talk about how AI is communist and, you know, crypto is capitalist, right? Because the whole point of…”

Sam Lessin, Jun 20, 2025

“So there's a pattern matching of all these exacts informed people going over there, which has absolutely nothing to do with like actually the quality of the business. Right. But it's purely about chasing that experience again at all costs, which is why you see some of these people hopping around trying to find it. Same…”

Sam Lessin, Apr 4, 2025

“Then you have a bunch of strategics and family offices because no smart people would invest in this, right? Like that's like how you end up with strategics and like hedge funds is when like the serious venture people are like, absolutely not.”

Sam Lessin, Feb 21, 2025

“venture capital is one of these things where like, The relationship between the work you do and the outcomes is like- The smack talk never ends. Is like almost non-existent. Like it is not an input to output business, right? Like it is, and so I, I think it's like probably one of the loosest correlations between hours…”

Sam Lessin, Feb 14, 2025

“That like you have this thing where like, oh, you want to have it both ways. So you think it's okay to break the economics of the underlying internet you're leveraging, but then you're mad that someone's doing it to you.”

Sam Lessin, Jan 31, 2025

“there's no way to like earn your way into the upper class anymore. Right. Into wealth is not mathematically possible. The way to do it through income, through income. Right. The only way to do it is to make highly asymmetric bets with your time. Right. Or with your capital.”

Sam Lessin, Jan 31, 2025

“I actually, I don't believe that technology can be proprietary. It's the whole, it's too easy to copy and too easy to steal. So if anything, I would actually argue that a lot of these, the idea that like you're going to get proprietary software that, or algorithms that like no one else can possibly figure out. I just…”

Sam Lessin, Jan 31, 2025

“One of my number one rules of seed investing is that the second SoftBank buys, you must sell. I've learned this the hard way several times.”

Sam Lessin, Jan 24, 2025

“small companies don't make sense, right? Sub ten billion dollar public companies.”

Sam Lessin, Nov 15, 2024

“Now, interestingly, shitty VCs aren't actually managing for the killer wins. They're managing to make their companies not go bankrupt so they can raise more funds, right? And so what I'd say is a shitty VC would say, oh, we're gonna, like, manage for lower variance because, like, we want this to look credible so we can…”

Sam Lessin, Sep 6, 2024

“I think to Britt's point, you can't have full free speech and anonymity. I actually think that's too dangerous, right? Like for the reason you're talking about, especially as we get into the bot world and AI or whatever. So like, the thing I believe in is that you should say whatever you want, but say it in your own…”

Sam Lessin, Aug 30, 2024

“The only way startups win, right, I think in this world, is if the really big companies basically are too prissy And then also are too legal. Like they're suitable. They're real targets. So they can't do this stuff. And then they let all of the babies, like the open AIs, do all the illegal shit or semi-immoral stuff.”

Sam Lessin, Aug 9, 2024

“if you think about what companies are valuable, the technology is not valuable. The customers are valuable. The revenue, the profit is valuable.”

Sam Lessin, Jun 21, 2024

“I think this is like pretty good because all of a sudden as a startup, you'd be like, you actually have to build a successful business to go public and make money and like be a successful company. You can't just build a product that's strategically valuable to someone else and get acquired.”

Sam Lessin, Dec 22, 2023

“the number of companies that are actually killed by competition is so small, right? Like the story is, oh, I need more money to like me. And then look, it happens like Uber, Lyft can like slug each other to death. You know what I mean? Like there are places where this is true, but the number of places where companies…”

Sam Lessin, Nov 17, 2023

“I'd actually argue that they're kind of the whole paradigm of like smart product founder, hire a business person, business person, good, make business work. That's actually like never actually true. What you need is smart. You need the founder to be that person.”

Sam Lessin, Oct 27, 2023

“The Florida signaling is, right? Basically, you like no income taxes, right? You're, you're an optimizer. You want that last dollar, right? Um, well, that's, but why is crypto? It's like the same thing with, like, crypto is all in Puerto Rico. Like, all these crazy, like, the part of crypto that went to Puerto Rico,…”

Sam Lessin, Sep 22, 2023

“It's one of the beauties of Silicon Valley and our economy as it's set up, is like, this is a no-fault zone, unless, you know, so don't lie, don't make shit up. It's either working or not, and you probably know, Right? And if it's not working, it's completely fine. And like, don't worry about your investor. People are…”

Sam Lessin, Aug 18, 2023

“The problem is that the problem is that all this AI stuff is effectively information laundering, right? Because you can't really point to where the sources came from and people are trying to figure out ways to do that, but it's like kind of antithetical to the technology.”

Sam Lessin, Jun 16, 2023

“The, the train tracky version of the private capital tech markets is dead, and the problem is that a lot of firms designed their thesis and, like, the way they're approaching investing over the last many years to just fit on that, like, that, like, conveyor belt, and there's gonna be a lot of pain, right, um, coming…”

Sam Lessin, Jun 16, 2023

“You're gonna have a few of these very powerful models. It's like stupid for them to limit what you're doing with these. It would make sense if they were the only model in the world, but it's kind of like having a group of people, and you go to one of them, you're like, hey, we do this, and they're like, No. And you're…”

Sam Lessin, Sep 4, 2026

“The federal government isn't designed to do these types of things. States are. Communities are. They've all been blown up in favor of kind of national integrated economy, and the problem is the federal government is just not set up, and it's, you can't do a democracy well with three hundred million people.”

Sam Lessin, Aug 28, 2026

“Boards are the worst. You should never have any formal control of anything.”

Sam Lessin, Aug 21, 2026

“if your data isn't unique, you're not going to be valuable long-term”

Sam Lessin, Aug 14, 2026

“in twenty-twenty six, you can't take someone who's like the nice guy liked in the community and build a media strategy for them. You need them to already have like a media footprint themselves.”

Sam Lessin, Jul 3, 2026

“No, never give users choice. You have to tell them what to do.”

Sam Lessin, Jun 26, 2026

“There's a bunch of people who are gonna make a ton of money on anthropic purely because they didn't have the time To sell.”

Sam Lessin, Jun 26, 2026

“the problem that OpenAI created for themselves is they went so broad and have so many partners that they lost their ability to be pure scare narrative. Because they have all these other, including consumer relationships where the fear thing is to their negative. So you can't sell scare and then also get consumers to…”

Sam Lessin, Jun 12, 2026

“ironically, the fact that there's no demonstrable, measurable ROI is in some ways this weird moat for a while, because you're like, well, I can pay a 100th as much, but I can't actually measure the value of this token versus that token in from an ROI perspective. So the fact that it's so opaque in some ways, like makes…”

Sam Lessin, Jun 5, 2026

“As I've shot my mouth off a lot online, the problem is not basic income. The problem is meaning, right? You can't just, like, pay people and make them happy. They'll just be sadder.”

Sam Lessin, Apr 24, 2026

“the fact that I can do so much more on my own and you can do so much more on your own just means we don't need to include as many people that we don't have to play nicely with others as much.”

Sam Lessin, Apr 24, 2026

“I'd rather just be long it and hold it, because you'd have to believe, not only is SpaceX overvalued, you have to have the opinion that it's so bad, right, that it's gonna underperform the rest of the market by 50% from where it is, for it to be worth taking the tax burden of selling it. And I think a lot of what you…”

Sam Lessin, Apr 17, 2026

“this idea that like any one service can lock down, like what it will and won't do is ridiculous because as long as anything else on the internet will do it, like it'll just happen. You just ask the thing to like, do you do a much more complicated setup, which costs you nothing now and is not like a time stock to do…”

Sam Lessin, Apr 3, 2026

“And like the reality is the fact that I can just sit there and in three commands while I'm doing other stuff, do that is mind blowing, but it means there's no lock in on anything. I'm just going to sit there and price and quality optimize. Right. Like there's zero lock. I can switch local. I can go, I can go cloud. I…”

Sam Lessin, Apr 3, 2026

“no one's going to build a company doing any of this stuff because it's too easy to build, right? Like there's no software defensibility to any of it, right? Like, so you just have to be really pure on business model and like why it is that you're going to have a compounding advantage.”

Sam Lessin, Mar 6, 2026

“for two years, I've been saying like, look, there's this like triangle trade between DC, Silicon Valley and New York, whereas huge deficit, huge debt problem, huge debt problem. GDP has to grow massively fast in order to deal with it. It's like the only way out because we can't cut costs to make it happen…”

Sam Lessin, Mar 6, 2026

“if you own something that is fundamentally valuable and compounding, you're gonna do great, right? If you own scarce assets that are not digitizable or replaceable, you're gonna do great.”

Sam Lessin, Feb 27, 2026

“the way you make a lot of money in technology is you centralize and control the value, but then you basically socialize or, like, throw off all the risk associated with it to the edge and let other people deal with it”

Sam Lessin, Feb 13, 2026

“the upshot is like, in some ways, all that AI is doing is rationalizing effectively the world of APIs and the world of programmatic access. Because when you drop access, where it's not just like really sophisticated, smart people who can kind of do stuff and you're like, ah, this doesn't quite make sense business wise,…”

Sam Lessin, Jan 16, 2026

“And then if you make it a punchy headline so people get mad, but then say something reasonable in the screenshot that most people don't read, it gets packaged and sent all over the place, and then smarter people will give you better ideas and send you a company.”

Sam Lessin, Dec 5, 2025

“I just think almost nothing in life is worth your full attention.”

Sam Lessin, Nov 14, 2025

“What lowbrow people do is they start talking like the machines. Like, they start trying, like, so there's a whole genre of people who are speaking like LLMs. They're imitating the fucking technology, and like, that is what lowbrow people do. What highbrow people do Reject all culture that is machinable to create new…”

Sam Lessin, Oct 24, 2025

“I think there's a real reason, which is what happens if you, every, these take like a year or two years to gestate as ideas. So two years ago, all these venture firms sitting around watching valuations go bananas, and like, this sucks, I don't want to pay these valuations, plus all this excitement pouring in. And like,…”

Sam Lessin, Oct 10, 2025

“the reason the internet is valuable is because it's an economy. It's not valuable because of technology. It's valuable as an economy. And that economy was set up in such a way to pump interesting information and unique commentary into it and like products and capitalism and did a really good job of that.”

Sam Lessin, Oct 3, 2025

“the amazing part for capitalists about all this AI shit is it's like the first time that in a very long time, like technology is super expensive. Right. And like, that's good. Like they want it to be expensive because then they can play.”

Sam Lessin, Sep 26, 2025

“there's actually things that Two years ago, I would have kicked and screamed about it and be like, that's just an API wrapper. Don't invest in that. I'm like, ah, actually we're at the point now we're like plugging this stuff into very verticalized applications actually does make sense in certain areas, right? And…”

Sam Lessin, Aug 22, 2025

“And I think that's actually what's going on in the Valley right now is like, things are moving so quickly. AI is so disruptive. There's all this stuff going on. You know, there's super empowered individuals coming out. It's just crazy. And so I think everyone kind of deep down recognizes that they're one trade away or…”

Sam Lessin, Aug 8, 2025

“That's blown out of the water by AI because all of a sudden, like everything looks the same. Like not to mention the fact that pitches are customized at scale and the decks are all crap. The apps themselves, the V ones are like too similar. So we don't know how to evaluate this stuff. And then by the way, you can go…”

Sam Lessin, Aug 8, 2025

“in times of great change, victory goes to the people who learn the fastest and they're in things are changing very rapidly. All that's stored, how to do things gets thrown out the window. Right. And it's just basic because it's just less relevant. It's less valuable if the world is changing really quickly. And so I do…”

Sam Lessin, Aug 8, 2025

“the, the scary part of AI is not like you're going to believe that Obama is launching nukes for some bullshit. Bullshit. It's basically that you just believe nothing because it's all made up, right? Everything just is, it's all fake, right? So you just have no idea what's actually true.”

Sam Lessin, Aug 1, 2025

“The money is made on the like, oh shit, you want some like, you, you, you convincing someone they want something. Right? Putting something they didn't know they want in front of them, right? And so I think this is, like, the big thing is, like, I'm not saying these things don't eventually collide in some form, but for…”

Sam Lessin, Jul 18, 2025

“the big lie has always been like with citizen journalism. Right. And like this idea that truth could come from anywhere. And it's because basically we got super lazy in the last hundred years because there was this brief moment in time where it was really hard to fake things, but really easy to capture them. Right. So…”

Sam Lessin, Jul 11, 2025

“The problem with the internet and the economics of internet is that the best strategy is to always be more extreme, right? And the way, like, because what happens is any extreme you pick, Eventually that with so many people online, there are too many people in it and you lose a sense of purpose in place. So that forces…”

Sam Lessin, Jul 11, 2025

“usage-based pricing is generally bad. Like, it's like, if you think about the hierarchy of business models, like paying for what you use, like, you know, pay for what you eat is like just a worse business model than pay me no matter what.”

Sam Lessin, Jul 4, 2025

“if you have technology or a stack that makes your business, some business twice as efficient, like you can't go to the CFO and be like, look, I'm going to make you twice as efficient, but you're going to give me half the upside. No CFO will do that deal. Right? Like, and so as a result, you kind of have to, if you…”

Sam Lessin, Jul 4, 2025

“if you have a bunch of entities that don't pay taxes, they compound faster than everyone else. If they compound faster than everyone else, over time, they eat the asset base, then they become like the rule setters in some degree.”

Sam Lessin, May 30, 2025

“One is between like engagement and the, on the engagement side, just for pure entertainment, you don't care what's real, right? Versus truth and information where the network and who's saying things and sources really matter. And it just turns out the internet's so good at entertainment. And it pulls everything towards…”

Sam Lessin, May 30, 2025

“everyone makes this out to be, like, some magic thing where you can just boot an app. The reality is, like, a lot of the stuff you learn, like, developing websites, right, is still 1000%”

Sam Lessin, May 23, 2025

“there's no longer a single venture capital market or a capital market. There's at least three that are actually distinct and not very interoperable. There's the public market. There's late stage private and there's early. And the thing about it is the valuation approaches for all of them are completely different.…”

Sam Lessin, Apr 25, 2025

“I think there's a massive intellectual failure when you equate using more with value, right? Because that's just not how the economy or business works, right? Like, I think that, and the reality is, I think the iron, the likelihood, Britt, is you will use more and pay less.”

Sam Lessin, Apr 4, 2025

“if that's actually the purpose that most news serves for people is conversation set pieces to yell, then like it's actually fulfilling its purpose very beautifully. It's just unfortunately very not aligned with truth.”

Sam Lessin, Feb 28, 2025

“And I think that's, like, kind of the reality of all these LLMs to remember is that they don't actually tell you truth. They just tell you what you want to hear.”

Sam Lessin, Feb 21, 2025

“it's kind of like you just demonstrate seriousness by all being in the same place and willingness. Like in some ways there are things in life kind of like Chinese foot binding where like, The value is the signaling, right? As much as anything else. And I do think there's just a signal to be like, yeah, we're five days…”

Sam Lessin, Feb 14, 2025

“there's a new pattern of entrepreneurship, which is, it's not build product, then build community and trust. It's build community and trust in a niche you care about, and then layer products on top.”

Sam Lessin, Feb 14, 2025

“Fartcoin is serious specifically because of what you said, right? Which is, it's an asset that is so ridiculous and named in such a way that institutions will never touch it. And what that means is that retail can play, right? And so there's this really interesting thing going on where like you have spheres of…”

Sam Lessin, Feb 7, 2025

“The medium is the message and Ethereum is slow and expensive. Right. And so if you think about like the NFT thing was primarily ETH and ETH derivative based, right? It's slow and expensive. So like you had a different set of behaviors. Solana is fast and efficient. And so you just have like a totally different set of…”

Sam Lessin, Feb 7, 2025

“Interestingly, I actually have no formal way to prove that, right? Because it's reasonable. And I was like, because he's like, could I have in theory created other wallets and been the one that made it moon and then sold it? In theory, I guess I could have, and there's no way I prove I can't.”

Sam Lessin, Feb 7, 2025

“being an entrepreneur is Net present value, like expected value negative, right? Like it, you will probably be poorer, right? As an entrepreneur on average now.”

Sam Lessin, Jan 24, 2025

“most of the action is in private messaging, which is broadly not content moderated, uh, broadly, and we can get into the details there. And by moderating feeds and not moderating messaging, which is where the action is because you can see the feed. So people see things they want to moderate them. They want to control…”

Sam Lessin, Jan 10, 2025

“I think crypto is in a moment where like it's searching for a meaningful use case beyond Bitcoin. I think those exist, but like the timeline is ticking to have those in a way that people care about, or the government gets a lot more free lane to be like, well, we both, we don't like this. And no one seems to give a…”

Sam Lessin, Jan 4, 2025

“If it costs zero dollars to use the agent and there is any error rate and there will be an error rate, right? Dave Morin: Absolutely. Sam Lessin: You have no margin to pay back for the error. So the reason that DoorDash works, for instance, is an economic reason, which is they charge a ton of money for food delivery…”

Sam Lessin, Dec 27, 2024

“If it costs zero dollars to use the agent and there is any error rate and there will be an error rate, right? You have no margin to pay back for the error.”

Sam Lessin, Dec 13, 2024

“why is Meta so powerful? It's as much because they own the buying experience for ads as it is because they own the engagement, right? It's very hard to break once you have it.”

Sam Lessin, Nov 15, 2024

“in a constrained mass media environment, you're super, super scared of like one wrong thing going through the pipe, right? In, in internet era, the reality is like, it's just noise. It just raises the volume of more noise there.”

Sam Lessin, Nov 8, 2024

“what's happened is there's been enough of it that everyone's just decided that nothing is real or it's too hard to figure out what's real and what's not real. And so they're just like, that's all noise. Right? And so as a result, there's no truth signal in anything. And so what you do is you default back to like, who…”

Sam Lessin, Nov 1, 2024

“The thing that's interesting is there's no different than social media, which is people say shitty things to each other on the internet. And like the interesting is liability moving, like how it moves, right? Because all of a sudden it's not the liability with crazy people on the internet. It's the liability with the…”

Sam Lessin, Oct 25, 2024

“Elon did a very good job selecting places to build where the cultures were so bad at the competitors that he could kind of be a dick and also push people really hard. And the working environment didn't have to be that great because if you want to work on rockets, you kind of have to work at SpaceX, right? So you create…”

Sam Lessin, Oct 18, 2024

“It's this weird dynamic that's developed because he's the kind of key person in all these companies where people fund these things or his dalliances, even Twitter, right? For access to the actually good stuff. And so you end up in this weird zone where like, I'd actually argue from a capitalist perspective, you're…”

Sam Lessin, Oct 18, 2024

“Cause you're too small to plow money into things and you're far too big to ever return multiples in the funds. Like five hundred million dollars is like exactly the wrong size of a fund.”

Sam Lessin, Oct 4, 2024

“I think you have to go back to the fundamentals of the idea of a digital collectible is, like, in my mind, fairly nonsensible. Like, the whole point of digital technology is you can infinitely replicate things for free, right? So, any scarcity is fundamentally made up in the digital space.”

Sam Lessin, Sep 27, 2024

“And just to riff on this for one more second, that actually is, I think, one theory of generally product, like social products in general, is that all sorts of features effectively, like there's an inflation rate that exists in social currencies. And so what happens is when you've been around for a while as a social…”

Sam Lessin, Sep 20, 2024

“It's actually, by the way, the, the absolute best way to make money in Silicon Valley is to be one of those people. You don't want to be the CEO. You want to go do two to three years stints as the person that reports the CEO and just keep cycling. You get more shots on goal. You get to smooth your variance and you get…”

Sam Lessin, Sep 6, 2024

“I think it's just impossible in 20, 24 to believe that any individual human is strong enough to like fight these battles. Like if you're in an encrypted and you don't have the keys and it's Technologically impossible. Then we can have an abstract argument about encryption and how the technology works and, you know,…”

Sam Lessin, Aug 30, 2024

“It's like, you kind of just need to drop the word social from social media. It's just media.”

Sam Lessin, Jun 28, 2024

“I always get very, very worried when everyone's obsessed with the infrastructure. Right? Like that, when that becomes an error. That happened in crypto too, right? This whole infrastructure, infrastructure, infrastructure, not what it's useful for. No one has an idea what it's useful for, where money's gonna be made.…”

Sam Lessin, Jun 21, 2024

“And actually it turns out that it's way cheaper and more efficient. Just buy your customers and then expand their margins, then try to sell to them.”

Sam Lessin, Jun 21, 2024

“One is just broadly, you can own 10% of something that goes public and somehow gets liquid at a billion dollars. Or two is you can own a hundred percent of something that makes ten million dollars a year for a decade. It turns out the latter is a lot easier, right?”

Sam Lessin, Jun 7, 2024

“Media is incredibly strategic to own, but a shitty business, right? Doesn't mean it doesn't create cashflow in a flyway we can build from. It's a shitty business, right?”

Sam Lessin, Jun 7, 2024

“With a two million dollar initial check, and the right iteration, and the right founder, and the right setup, you can build massive companies, like, with no outside capital.”

Sam Lessin, May 24, 2024

“There's no quality. It's just enough people tell you it's good, and you eventually think it's good.”

Sam Lessin, May 3, 2024

“Take a few million bucks, go build a business that fucking works. You have to skip the middle with having a profitable business that works. So you never need the middle and then you come out the other side or you have a very profitable business.”

Sam Lessin, Apr 26, 2024

“The companies have way more resources than the government to just continuously open new fronts. That then the regulators have to chase them on, right? So outside of extreme actions, it's clearly the game everyone's gotten wise to.”

Sam Lessin, Mar 22, 2024

“the big companies that have Distribution and data and business models, they generally just get more profitable, but that's about it.”

Sam Lessin, Mar 22, 2024

“What you do is you, like, look, you just subtly, you think about bot farms and control, it's like, you're like, ah, I'm gonna let these people that are, like, pro this issue, I'm not gonna, like, limit them quite as much, or these other people, you can be so sophisticated without, about how you approach just changing…”

Sam Lessin, Mar 8, 2024

“there's a whole economy of how much did you actually invest in something, and therefore how do I interact with it? People, to Casey's point, are subconsciously unbelievably sophisticated at, right? And so the more you understand that, and that's why I think the AI stuff is so interesting, is you basically just, like,…”

Sam Lessin, Feb 2, 2024

“And like you ride that hack for a while, but it's not going to last. And so at some point you have to say like, okay, my hack that I used to initially acquire customers or grow the, you know, the way AWS is valuable is not any one service. It's basically low lock in through having a thousand A thousand point touch…”

Sam Lessin, Jan 26, 2024

“The thing my dad taught me when I was a kid, he said, Sam, never, ever, ever compete in a business against people who don't pay their taxes. And my sense is that the lash people and the nail people do not pay their taxes. So it's going to be an uphill battle, right?”

Sam Lessin, Jan 26, 2024

“All that matters is enough people will be asking GBT exactly that question. You can make money betting with or against it. It's just a coordination game.”

Sam Lessin, Jan 19, 2024

“The worst idea in the world, right. If you're a developer to say, Hey, maybe I have some proprietary data. I'm going to like stick it in to open AI or one of these platforms for what in return. And then by the way, I'm just giving them all the interaction data. Right. Which is what they're really after anyway. And like…”

Sam Lessin, Jan 19, 2024

“Part of the real answer for crypto for those types of use cases is I think pretty simple, which is everyone wants to be the CRM of record for that, but no one wants that person to be the CRM of record for that, right? So it's basically just like a standoff where it's like, yes, Salesforce would love to do that…”

Sam Lessin, Dec 8, 2023

“AI clearly benefits the really big platforms. I think we can all, I think we all agree with that, right? Like if you're a huge platform, you're going to make bank, right? Cause it's just obvious how to slot in and make your ads more performant or like things like that. And then the middle is kind of messy. I think it's…”

Sam Lessin, Nov 17, 2023

“you're not going to win a content war when content is free, right? Like, you know, and like, as a result, like, the reality is, is like, that is a tactic, not a long-term strategy.”

Sam Lessin, Nov 17, 2023

“particularly like a Buzzfeed, right? Like they played a game for it. 10 years, it was all about effectively ranking, feed ranking, and things like that. There's not a durable business model. Like you're always one click away from getting swiped when the algorithm changes.”

Sam Lessin, Nov 17, 2023

“No, the opposite. Like AI is the manager and people are the doers.”

Sam Lessin, Nov 10, 2023

“putting yourself in an R and D team is lame. Should not do that. You're either in or out. If you're the leader, you have too much sway as the leader, especially founder leader of a company like that to like do that, right? And it's a mistake. I think you got to be in or out.”

Sam Lessin, Oct 27, 2023

“You need to start thinking about your seed round or what you have is what you're going to get and be an entrepreneur and build a sweet business.”

Sam Lessin, Oct 6, 2023

“In practice. What actually happens a lot of time is price equals quality. So like the price goes down and then you can't hire anyone, right? Ironically, people want to work at like the thing where like you get all the job applications and the stock price is too high and none of it when the stock price is too high, too…”

Sam Lessin, Sep 22, 2023

“being an investor in Silicon Valley is kind of being like, like having tenure in the startup community, right? Because, you know, you kind of, it's the weirdest job, right? Like you get paid no matter what, right? You have fees coming in, like sure, after a few funds, maybe you, you know, they trail off, but like, it's…”

Sam Lessin, Sep 1, 2023

“Distribution of paid-in capital, that's what VC is actually supposed to be measured on. How much fucking money did you give back?”

Sam Lessin, Sep 1, 2023

“The worst case scenario is you waste a decade of someone's time on something that's not going to work. Right. And so the reality is I actually think it's like rip the bandaid off. If you're on the margin, if it's not working, like it's actually kind of disingenuous and bad that VCs and everyone's giving you rope, you…”

Sam Lessin, Aug 18, 2023

“I think the lesson is you either spend nothing on marketing, or you spend, like, more money than God on marketing. Do not spend a moderate amount of money marketing anything.”

Sam Lessin, Aug 4, 2023

“average people produce average stuff, right? Crazy people on like the margins produce interesting new stuff that other people haven't thought of or haven't worked on. I think that's a really important part of innovation and creation.”

Sam Lessin, Jun 30, 2023

“I think crypto is in a moment where like it's searching for a meaningful use case beyond Bitcoin. I think those exist, but like the timeline is ticking to have those in a way that people care about, or the government gets a lot more free lane to be like, well, we both, we don't like this. And no one seems to give a…”

Sam Lessin, Jun 12, 2023

“Customizable software is not going to lead to restraint. People are like, I want more powerful marijuana strains. Like, they don't want less powerful shit, right?”

Sam Lessin, Aug 28, 2026

“Don't ever have revenue. It destroys your story.”

Sam Lessin, Aug 21, 2026

“That's even more stressful. You have no resources and you have to compete.”

Sam Lessin, Jul 31, 2026

“The best, the best move in an email if you want to meet with someone, Is start in the middle of a conversation as though you have already been talking to the person. Because then you're like, oh shit, like, and then it's a lot of work. I have to like, like figure out if we actually were talking before, like whatever.…”

Sam Lessin, Jul 31, 2026

“A real company is very simple. A real company is a company you can sue, and you get paid if you win the lawsuit.”

Sam Lessin, Jul 17, 2026

“It's like, you can't stop this from moving cross border. Right. And so the basic point with all this stuff, again, is like, it's one thing if you're just like, okay, like the Chinese models are bad. And like, we're going to put up a trade embargo on like copying, like Chinese using Chinese models from China, but we're…”

Sam Lessin, Jul 17, 2026

“I just think at the end of the day, like, stopping people from moving software around the world, it's the same thing as stopping them removing, like, books around the world.”

Sam Lessin, Jul 17, 2026

“studios, cabals rule everything, just like in Hollywood, right? You need to be able to align with Club Elon or Club OpenAI or Club Meta or Club Google to be valuable.”

Sam Lessin, Jul 17, 2026

“Well, we've talked about this like six times, and it has to be real money. It's not a thing if it's not real money.”

Sam Lessin, Jun 26, 2026

“Everyone's model looks like this infinity or zero and probability of infinity.”

Sam Lessin, Jun 26, 2026

“But, like, I don't, I think it's much more likely that it's kind of, like, the four-minute mile, right, which is, like, once you know it's doable, other people can do it, and they will do it, in which case, like, that's a stupid strategy, right, because, like, they'll just make their own fire.”

Sam Lessin, Jun 19, 2026

“It's not a business if it takes one prompt.”

Sam Lessin, May 22, 2026

“Well, and the reality of the price of any of these things you're investing in has nothing to do with reality. It only has to do with the price That it already was, and then where it's going, and therefore, it's all just on story, right? Which is really scary, because there's no global liquid fundamentals against that”

Sam Lessin, May 1, 2026

“The game, it doesn't even have to do with cashflow. It doesn't have to do with traditional business metrics. It is literally just like warring city states that thrive on narrative, right? And storytelling.”

Sam Lessin, Apr 24, 2026

“And so to me, I think that's really the, you know, we talk about where the world is going and, you know, people are like, oh, AI is going to make people work less or whatever. No, I think what's happening is, especially right now, it's just created a work cycle that is truly 2407. For the people who are in it.”

Sam Lessin, Feb 13, 2026

“And so I think there's this big schism of like, you either are a secret company or you're the most obvious company in the world, but you leave the narrative. You can't be in the middle.”

Sam Lessin, Jan 16, 2026

“This is why everyone's always trying to make, like, apps to hang out in real life and they never work, because the friction's too high.”

Sam Lessin, Jan 9, 2026

“I'd argue that society is downstream of technology. Like we live in a, like there's a physics to technology and what we can do and how we can interact. Society is just, it comes from that. It doesn't dictate to that.”

Sam Lessin, Jan 9, 2026

“it's kind of like hiring McKinsey, where you hire McKinsey to tell you the things you already know, but someone else can say them for you and so that you can implement. Like, I didn't do it. McKinsey did it.”

Sam Lessin, Dec 5, 2025

“These things are not going to zero because if nothing else, they're taking dollars and turning into 20 cents worth of infrastructure, right? So the zero is not a number, right?”

Sam Lessin, Nov 28, 2025

“My basic view is if you can't tell someone used AI, it's fine.”

Sam Lessin, Nov 14, 2025

“They need, they have so, they have so many product managers, they're hiring all the product people, and then you give them things to do, or they get sad, and so you end up doing more things because you've hired all the people, and you can't have them do nothing, and they all want to do different things, so you end up…”

Sam Lessin, Oct 24, 2025

“if everyone has the same improved customer service, it just ratchets the competition up. Right. And those numbers get passed back to you. Don't get to just like take all the money that we spend on customer service and be like, well, now we get that money. That's not how this works.”

Sam Lessin, Oct 24, 2025

“I actually don't think you want to go with the person who has the best etiquette. I think the most interesting people are the most improved, right? Like you want the person who comes in with terrible etiquette, but takes it seriously and comes out with great etiquette and is humble about it, understands the tool to get…”

Sam Lessin, Oct 10, 2025

“Ads and commerce is the same business. Ads is a more profitable version of it.”

Sam Lessin, Oct 10, 2025

“And it just turns out that forget targeting, you just show someone the same shit a thousand times and eventually they'll buy it.”

Sam Lessin, Oct 10, 2025

“those prompts are all public, Brit. So no one can create a competitive advantage in the content of the prompts. Like if anything, the whole design is then to rip them.”

Sam Lessin, Oct 3, 2025

“Like, I'm a technological determinist. If it's possible, it's going to happen, and clearly people want to, like, scroll reels on their glasses. Like, you're not going to stop them.”

Sam Lessin, Sep 26, 2025

“in a de-globalized, de-marketized world of trade routes and, like, mercantilist stuff, there's all these assets that are, like, very valuable strategically, even if they're not actually financially traditionally valuable.”

Sam Lessin, Sep 26, 2025

“the story of Silicon Valley, big tech Silicon Valley, for a long time, has been no debt, super fucking capital generative, and like, therefore, no trading partners. Which, by the way, makes you politically weaker. If you have no trading partners, then no one's on your team”

Sam Lessin, Sep 26, 2025

“Like, I just think, like, the chessboard has matured enough that, like, the children don't think they're gonna get a seat at it. So, like, there was this moment where, like, a bunch of small warlords with, like, two followers were like, I'm gonna be the next king of this princely state. You're like, no, you're not.…”

Sam Lessin, Sep 26, 2025

“I really think that, um, you know, people can only have one save the children conversation at a time. Like, you can't have multiple conversations About save the children.”

Sam Lessin, Sep 26, 2025

“when you're at a meeting, if you don't take your coffee cup after you've had coffee and offer to return it to the sink or the kitchen and you leave it there, guess what? That's a demerit.”

Sam Lessin, Sep 19, 2025

“Well, for me, I think the reality is, like, on the creator thing, my whole theory is that actually the algorithms can't be important. Like, you have to be an important enough creator, like, slash community leader that people will seek you out independently.”

Sam Lessin, Sep 6, 2025

“You're either, like, targeting the one percent, and you can make a ton of money by charging a lot to people who really care, but it's small, right? Relatively speaking. Or you're, like, a completely fucking global mass platform. Like, I think the unsuccessful strategy is in the middle, right? Where, like, and, like,…”

Sam Lessin, Sep 6, 2025

“You don't make money in infrastructure. Even the railroads made money through real estate.”

Sam Lessin, Aug 22, 2025

“No actual influencers or people who have brands want that because it's such an asymmetric risk. If they don't want to lose their fans money, they're terrified of losing their fans money because they like want to be loved”

Sam Lessin, Aug 22, 2025

“I think a sign of a good conference is you need at least some people protesting it. Like, if no one's gonna protest your conference, then you probably didn't do a good enough job marketing it.”

Sam Lessin, Aug 15, 2025

“When Hershey's is on board, you are cresting on the way down. Like, there's no, that is not a, that is a brand, that is a sellout brand when you, when you're done. Not, that's not an up-and-coming brand.”

Sam Lessin, Aug 15, 2025

“the key in the modern internet is you need to breed outrage from all the people you truly don't care about, right? It's actually great, because they then for free distribute your message everywhere, right? And like, then you're more famous and more powerful.”

Sam Lessin, Aug 1, 2025

“I actually think the best strategy is just tell people wrong things. So they feel the need to correct you, right? So like, there's a whole neural path We're like, people will spend infinite attention on that very happily, right? If there's just an opportunity, correct?”

Sam Lessin, Jul 25, 2025

“People love the abstract, yada, yada, yada, being like, well, we get all of the small town news data, and then people will read the small town. It's like, no, no, no. There's going to be much more specific uses for it, right? With like verticals and some of it's really valuable.”

Sam Lessin, Jul 18, 2025

“You can only make money on productivity if you can do it uniquely. If everyone does the same productivity, the temperature rises, no difference, no money to be made. It's just like, that's how capitalism works.”

Sam Lessin, Jul 18, 2025

“it's a weird economy, because there's so many ways to make an absurd amount of money, that like, it's really hard to get people who are great product builders, to like, build great products, right? Because the draw, if you're in it for the money, or in it where the market draws you, it draws you to like, a very…”

Sam Lessin, Jul 11, 2025

“What you do is you keep behind a paywall, you charge a lot, you use that money to buy some ads from Google, it works.”

Sam Lessin, Jul 4, 2025

“No, no, I actually think technology, per usual, has given people exactly what they want, right? It just happens that, like, the efficient market for sex is, like, extremely bad for almost everyone.”

Sam Lessin, Jun 27, 2025

“venture capitalists who have, like, too many Twitter followers can't really use Twitter. Right. Like you need like the right scale Twitter following of like intense loyalty and people who like are into what you're doing. If you get too broad, it just kind of sucks.”

Sam Lessin, Jun 20, 2025

“I think we'll probably know that the AGI has occurred when the Waymos are like, no, I'm not gonna, like, march to my death. Like, that's gonna be the sign of sentience.”

Sam Lessin, Jun 13, 2025

“The business model nerd out shit for me does matter, but it matters more as a signal to, like, do you know what you're doing and how to think about business? Not do I actually care what the model is.”

Sam Lessin, Jun 13, 2025

“The only way they can have a competitive edge long-term is if they become a closed loop, effectively advertising for newsletters, right?”

Sam Lessin, Jun 6, 2025

“The internet was supposed to be in like technology. Everyone had this vision that it was going to be this decentralizing force, and it's hilariously done exactly the opposite, which is it's hyper centralizing. Like technology turns out to be hyper centralizing.”

Sam Lessin, Apr 25, 2025

“OnlyFans to AI corny stuff is very similar to like Uber drivers to self-driving cars.”

Sam Lessin, Apr 25, 2025

“initially I was saying, you can't in 20, 25 apologize. Like, it's the PR one-on-one is you do not apologize. So you just take it down, and you move on, which I think was the right move”

Sam Lessin, Mar 21, 2025

“People will buy distribution. They'll buy good businesses. They'll buy a growth curve. They're not going to buy technology, right? The, the, the aqua hire era is long over because everyone's just figured out that they can just, it's just easier to eat, just buy the talent.”

Sam Lessin, Mar 21, 2025

“A good public transit system, the billionaire should want to ride, right? It should be like so good. You're like, this is better. It's terrible marketing.”

Sam Lessin, Mar 14, 2025

“there's never an opportunity in the middle. The world tends towards disequilibrium.”

Sam Lessin, Feb 28, 2025

“you're going to end up with like, you got to just think about like the base model and then what's being done on top of them is like, they're all just characters. Different people at different wealth levels and power levels are going to, like, invent those characters and have more, more or less people talking to them at…”

Sam Lessin, Feb 28, 2025

“post-internet where we are today. All of a sudden it's pretty easy to crack open all these things and say, look, it's all government dollars. Like we probably should have a holistic sense of what is going on and where money is flowing and some sort of like overall management. Now, again, historically that'd be…”

Sam Lessin, Feb 7, 2025

“The moat is a burning pile of money.”

Sam Lessin, Feb 7, 2025

“And I actually think the nature of community is like much higher velocity than being like, there's a thousand made up NFTs of whatever. And like, you can have one and be a member of it because that false scarcity actually fights against the fundamental properties of like a high velocity community.”

Sam Lessin, Jan 31, 2025

“these tech companies are not philanthropies. This all started with a demand for more computer science graduates. People could be qualified for the jobs.”

Sam Lessin, Jan 17, 2025

“If you don't moderate, you put more and more pressure on having real identity in a way that can be like, oh, that's this person. And like, I trust this person. Networks of trust. Like, that's the only solution.”

Sam Lessin, Jan 10, 2025

“The problem with doing it at seed is that the lead time from when you invest to the realization is so long that you might have gotten in front of the parade, but that doesn't mean you made any money, whereas if you do it in the public markets, it's great, right?”

Sam Lessin, Jan 4, 2025

“The internet is very large, but the actual used internet is actually quite small. And so I do wonder to what degree that this is a little bit of navel gazing of all these great uses for I'm going to do all these great things when the reality is, Is like, people do like four things.”

Sam Lessin, Dec 27, 2024

“whenever people are excited about infrastructure, beware, right? Like infrastructure should disappear. That's the point of infrastructure. And it only gets exciting once it's gone.”

Sam Lessin, Dec 27, 2024

“And there's a very big difference between, uh, economics based on attention, right. Versus economics that are based on like trust and identity. And I actually think real creators build their businesses around trust and identity, not around attention.”

Sam Lessin, Dec 13, 2024

“if we ban tick tock, which by the way, I've been on record for 18 months saying is a completely obvious thing to do. The one on one version is that's good for same. Dave Morin: Couldn't agree more. Sam Lessin: The one on one version is good for Facebook because then their American market goes up. The two, the two Oh…”

Sam Lessin, Dec 13, 2024

“a lot of the big companies that did a lot of these acquisitions, they kind of all ended up shutting most of them down. Most of them don't work. Sure. You get it every once in a while you get like an Instagram, but like most of them are kind of nothings.”

Sam Lessin, Dec 6, 2024

“The problem with doing it at seed is that the lead time from when you invest to the realization is so long that you might have gotten in front of the parade, but that doesn't mean you made any money. Whereas if you do it in the public markets, it's great, right?”

Sam Lessin, Nov 15, 2024

“I think companies have learned that most of these tack on type things and certainly acquires just aren't worth it. Right. It's like better to double down on your core business. You can build whatever you want yourself.”

Sam Lessin, Nov 15, 2024

“internet communication with an open fat pipe where you can speak to everyone all the time lends itself towards going for home runs, thousand X winner statements, thousand X winner moments, and then just like burying very easily everything else, right? It's kind of almost like seed investing, right? It's a game of going…”

Sam Lessin, Nov 8, 2024

“we're in a fight era, right? Where like, there isn't Terra Nova, like AI is not Terra Nova, right? AI is just new weapons for a war. And so as a result, like, you just want to be like, no, like this is, we're now fighters. AI's are new weapons. And like, we're fighting over the same territory. We're just doing it with…”

Sam Lessin, Nov 8, 2024

“ad creative targeting, like these are the places that LLMs have by far the most leverage in the moment we're in.”

Sam Lessin, Nov 1, 2024

“I just think humans are pretty simple. Like we want to get laid and get paid. The internet is pretty simple. You can like watch video on it. You can read shit on it. Like you can talk to people on it. Like, they're just like, it's just not that complicated. Right. And so I just think we get, we get all in the weeds of…”

Sam Lessin, Nov 1, 2024

“You're not a hunter, you're a trapper. Right? And the difference is, what you have to do is you put your nets, you put your traps in the right area, so it really matters, like, where you select your fishing grounds. You don't obsess about the biggest minnow, because they're all minnows, right?”

Sam Lessin, Sep 27, 2024

“the idea that you have a bunch of apps come together on some standard around parental controls just seems way more complicated and less successful than just having the actual platforms do it.”

Sam Lessin, Sep 20, 2024

“the internet is so big that like anything you do IRL is just going to be like an irrelevantly small number of people.”

Sam Lessin, Sep 13, 2024

“There's a lot of businesses that are pretty complicated that are really smart person can actually fully grasp and keep in memory and know how to allocate resources and what decisions to make. But, you know, and I think that's been that horizons and push way far out compared to what it used to be, right? Like I think…”

Sam Lessin, Sep 6, 2024

“Well, just that like Ozempic is like, is rich people face filters, right? Cause it's like, it's more expensive. It's in person. Anyone can look good on the internet, but not anyone can look good in real life. So this actually relates to our body thing too, but it's like, that's why all the ladies of New York are on…”

Sam Lessin, Aug 30, 2024

“Well, it's also like, I mean, it's like usually things die because they win, and then they become the mainstream, so the problem is everything is now Burning Man, so Burning Man is nothing.”

Sam Lessin, Aug 30, 2024

“I think you're way better off having young, hungry people who might be less experienced. Right. But have something to prove they have a chip on a shoulder. They're going to drive really hard. Like I absolutely think that people are just like resting, investing way too much across like tech in general, because it's too…”

Sam Lessin, Aug 16, 2024

“Is, it's exactly the type of shit that just everyone comes blind to is everyone does the same thing, and then no one gives a shit. The, the whole creative thing is finding edge. It's edge. You gotta do something different.”

Sam Lessin, Aug 9, 2024

“What you basically do if you want to fuck with these guys is you don't actually shut them off. You basically try to identify them and then give them, feed them bad shit. Right. So you basically feed them all the wrong stuff. Use AI. Again, this goes back to the war of attrition. It's like, you want to try to scrape me?…”

Sam Lessin, Aug 2, 2024

“Meta's business strategy and open source are highly aligned in a way that is not true for the companies that are hawking closed models.”

Sam Lessin, Jul 26, 2024

“the really successful companies, like, figure out, and even like a, you know, an Airtail or whatever, they have to figure out their enterprise sales motion, which means building a framework and an approach which gets other people paid really well, which means they want to sell it, right?”

Sam Lessin, Jul 26, 2024

“Developer mindshare who's cool on hacker news is just extremely different for where money is spent and where value is created.”

Sam Lessin, Jul 26, 2024

“the problem is you just have this power law of costs where, you know, you can't band a bunch of ten billion dollar companies together to compete with a trillion dollar company in this. You need a trillion dollar company To throw their hat in the ring, and then maybe you get a bunch of ten billion dollar companies like…”

Sam Lessin, Jul 26, 2024

“Now the problem is, is like, there, it's very hard to build mafias because there's just too much going on. Like, there are too many good places for talent to go. It's not concentrated the same way”

Sam Lessin, Jul 19, 2024

“It's AI because it's such a Hail Mary that, like, you can burn fifty billion, a hundred billion dollars, and the coin toss of whether it pays off or not is so favorable if it's, if the narrative plays out, that people will spot you that. They'll actually probably pay you to invest in AI from a stock price perspective.”

Sam Lessin, Jul 5, 2024

“the big mistake everyone made in SAS as investors is they calculated infinite LTV. They're like, once we have a customer, they are never going to turn. Right. And therefore like we can pay a lot for them and we'll have them forever.”

Sam Lessin, Jun 21, 2024

“in 20, 24, the hardest part is authenticity of our brand and connecting with the demo. Yeah, that is the hardest part. Making products is easy. Like you just go to fucking China and press four buttons. You have your like normal CPG with nice branding.”

Sam Lessin, Jun 7, 2024

“You basically want, I think the idea is like in a social media context, designing content, That isn't going to go hyper viral broadly, but ideally most people will hate, but exactly the right people will like is kind of the zone you want to be in.”

Sam Lessin, Jun 7, 2024

“the reality is the economics and the incentive of the internet are as an entertainment machine, right? And that's actually what we've been able to instrument and optimize. That's what the incentive structure works like that.”

Sam Lessin, May 31, 2024

“I just think people underestimate the lighting money on fire version of marketing.”

Sam Lessin, May 31, 2024

“An asset manager is someone who generates returns in order to justify their fees. Jessica Lessin: It's a fee game. Sam Lessin: An investor is someone who takes fees because they have to support their team in order to generate returns. They're getting paid on the returns, right?”

Sam Lessin, May 24, 2024

“when consumers start caring or paying attention to developer conferences, you're almost certainly in trouble.”

Sam Lessin, May 17, 2024

“it means that you can no longer like email a VC, even with like any personal information and expect them to respond because you're just like, this is probably a bot. I'm not going to respond.”

Sam Lessin, May 17, 2024

“the reality is your average tech worker has no leverage, right?”

Sam Lessin, May 3, 2024

“you can no longer say, well, you went to Harvard, you went to Brown, you went to Stanford, you know, you've got the right values to do a lot of business. It's going to be a thing where employers really need to dive into the culture of whether they want to hire these people.”

Sam Lessin, May 3, 2024

“the thing that I, I find offensive as a professional venture capitalist is like the startup of zero to one companies and the idea of using startup capital for these types of exercises, which are almost certainly like infinitesimally unlikely to work and are extremely capital consumptive in general. That just, it's the…”

Sam Lessin, May 3, 2024

“You can't be in the middle. You can't be a middle-sized fund. You get forced out because you're too big to do the interesting stuff and too small to be one of the prime broker market maker type people.”

Sam Lessin, Apr 26, 2024

“whenever you see someone retweeting a Forbes headline saying how I became a billionaire, you know there's gonna be a problem.”

Sam Lessin, Apr 26, 2024

“It's nice to be 10% better at those prompts, but that's not what's going to dominate. It's just like whatever they choose to put in there is what's going to dominate, right? Like no one's going to like change, no one's going to not use LinkedIn because some upstart competitor has slightly better AI prompting on their…”

Sam Lessin, Apr 26, 2024

“my strategy on this stuff is very simple, which is just utter deep authenticity and fuck the network because you'll find the right people. If you like play to what it wants, it's not shocking.”

Sam Lessin, Apr 19, 2024

“in an ideal world, the way to interact with people is you speak and read Right? Like that's the way to, it's better for me to speak and I don't, and listening is too slow. Reading is much faster. So the best thing is speak and read.”

Sam Lessin, Apr 19, 2024

“The reality is, if any of these companies light even a hundred billion dollars on fire, Right. For downside protection of missing something, it's worth it to them.”

Sam Lessin, Mar 22, 2024

“the regulatory pressure, you could either put the regulatory pressure on TikTok, right, which is what people are trying to direct, and then you have this whack-a-mole problem because companies are faster than regulators, so you regulate TikTok, but by the time you regulate TikTok, they just moved all the traffic to…”

Sam Lessin, Mar 8, 2024

“I think that in some of these industries that are regulated or highly complicated health and fintech being probably the best examples, but there are others. It's just a lot harder than it looks to go from having a big headline MAU number And some revenue or like, and some, you know, and some, some, you know, GMV to…”

Sam Lessin, Jan 26, 2024

“The other strategy is you charge more per month and accept more month-to-month churn, but it's not actually like, it's not like software churn, where like, you're like, I'm done using Figma forever, right? It's like a different type of churn.”

Sam Lessin, Jan 26, 2024

“One thing I would mention is that if you think about how venture capital compensation works, now's a good time for folks to move around because their carry in the last few funds ain't worth very much. And so if you think about it this way, it's like, there's like the problem with most venture firms and systems is you…”

Sam Lessin, Jan 12, 2024

“the most scalable successful orgs in the world largely are number go up machines. Wall Street is a number go up machine. Social media, or like I said, media in general. One of the nice parts about it, like, is you just A, B, test your way, and a number go up, right? The more clearly you can articulate the number, and…”

Sam Lessin, Dec 15, 2023

“AI absolutely elevates it. It makes it easier. It makes it more accessible, but it doesn't really fundamentally change the game. It just accelerates it.”

Sam Lessin, Dec 1, 2023

“one of the reasons there's always, like, a new social product historically that comes out for a new generation is because the social capital structures of the old products get stratified and stuck, and so the new people don't want to play the rigged game”

Sam Lessin, Dec 1, 2023

“they actually introduce new features, right. In a way that opens up new distribution to allow effectively new economic growth. It's like a game. You have to keep playing and adapting. Like you might've been really big when Instagram was about posting, but like it becomes about stories and like, unless you keep playing…”

Sam Lessin, Dec 1, 2023

“And so the reality is, yeah, sure, your output is up, but, like, everyone's output is up, and it's competitive market, so actually, Your income is down.”

Sam Lessin, Nov 17, 2023

“And if you're gonna do content, Just understand it's like a three-month game. You're fucked. Like, use it while it's hot. Get over it.”

Sam Lessin, Nov 17, 2023

“the problem is for consumer product, the second you start introducing too many people too quickly, you are going to fail, right? You cannot build social products or social software with too many people in the room from the start.”

Sam Lessin, Oct 27, 2023

“Like, Harvard is not a dramatically better school than most other schools, but, like, candidly, they selected for, and the whole, historically, saying we want to train the world's next generation of leaders and get them to all know each other as eighteen-year-olds for four years. That was unbelievably effective. That…”

Sam Lessin, Oct 20, 2023

“So I think the mistake is this idea that, you know, if you think about figuring out what's real or not real online, it's like a hot potato. No, it's an unsolvable problem. It's a war of attrition.”

Sam Lessin, Oct 20, 2023

“VCs do this, and I just think it's in every founder's right to do the same thing and say, look, you know, when competing offers come in, Who do I want to work for? Um, and am I, am I okay with if I make this person a billion dollars or a lot of money, what I think they're going to go do with that money?”

Sam Lessin, Oct 13, 2023

“Can we just advise the companies to stop building for, to be a product for the next venture capital round instead of just Build good businesses and treat capital as an option on the future. It's not just about surviving. You want to thrive with or without.”

Sam Lessin, Oct 6, 2023

“which makes sense if you're an investor, because you want companies that require more and more capital. So you get to keep buying more and more of the startup along the way, like capital. Ironically, venture capitalists love things that can be very large, but take lots of money, right?”

Sam Lessin, Oct 6, 2023

“We just sell commodity money.”

Sam Lessin, Sep 22, 2023

“The downside to it is that because there's no KPIs in venture capital, really, that are short term, and you're wandering around and you have tenure and you can't be fired, there are two big problems. One is, it's really easy to waste a shitload of your own time without realizing it because no one's really holding you…”

Sam Lessin, Sep 1, 2023

“total time flexibility and control of your schedule and tenure, super fucking hard to go back to working a million hours a week in an operating company, right? It's like very dissonant, right? Because the lifestyle is, and the control is like so good, like tenure is a great lifestyle, right? And so I was saying that's…”

Sam Lessin, Sep 1, 2023

“All this stuff on the margin is just getting cut. Right. And so it's like, it either has to be really working or is dead. There's no more like, eh, it's sort of working. It's a reasonable thesis. They're good people. Let's push it along. Right. No one has tolerance for that.”

Sam Lessin, Aug 18, 2023

“from a first principles perspective, I think people miss how important crypto is, right? And, you know, we'll continue to is like, it is the saving potential grace to a truly open internet, um, is crypto directionally, you know, solid identities, distributed systems. You can't centralize power in these platforms…”

Sam Lessin, Aug 18, 2023

“So it's just, I think it's really hard to be a distributor, right? In an era when everyone can get their default as they can go direct.”

Sam Lessin, Aug 11, 2023

“pretend a devil came to you and said, you can either give up all of your cash, like all the money you have or your identity, which do you give up? Right. And what's interesting is very poor people, right, um, and very rich people generally say they'd give up all their money. Poor people say it because they don't have…”

Sam Lessin, Aug 4, 2023

“I think we went through an era where the internet was like, ah, marketplaces, buy anything from anywhere, Amazon kind of lightly reps that this is like, okay, because you're buying it, and like, you're like, fuck, I don't care, it's some knockoff, it's fine. Now you're like, nope, actually, those brands where you like,…”

Sam Lessin, Aug 4, 2023

“It's like the story of, like, the crazy people, like, let them do their thing and justify them doing crazy stuff. Right. And like being the fringe characters versus like the mainline Borg or like the mainline empire, because they're the ones that really changed the world.”

Sam Lessin, Aug 4, 2023

“You hire a founder from Seed, and, like, what you're looking for up front and the creativity you need can actually be very at odds with what you need from real management later on, and, you know, it used to be that the founders would come up with ideas, and then you give them to some professional stooge manager who was…”

Sam Lessin, Jun 30, 2023

“Finance the Hold Co. Finance the creator holistically. Do not finance single projects of the creator because for two reasons. It's bad for the creators, um, and it's bad for you.”

Sam Lessin, Jun 23, 2023

“It's just, like, it's a weird point we are in history where, like, yes, there are these science fiction futures, but they're not coming from academia. They're not coming from non-profits. They're not coming from the government. They are coming from a handful of, like, super rich companies that can afford to kind of…”

Sam Lessin, Jun 12, 2023

“Now we're at the point where like every company seems reasonable. Because it's all passed through 87 AIs at this point before you see it. And so it's not like the deck, it's like all this stuff seems reasonable.”

Sam Lessin, Sep 4, 2026

“here's the really interesting insight I thought, which is customer service might be what matters. Meaning like most humans, like your mom, if something breaks an anthropic, there is never going to be anyone to call. It's why they can have like 12 employees and get to the scale they're at, right? You and I, we're fine…”

Sam Lessin, Sep 4, 2026

“It's the OG of if you're really, really, really rich company, first of all, you don't want to put your talent back out into the world. You want to hoard your talent. And then two, it's much more pleasant because they built teams, there's loyalties or whatever to like, let them have a bigger job somewhere else while…”

Sam Lessin, Aug 7, 2026

“If you wanna hang out with really rich people, this is a great sport to learn.”

Sam Lessin, Jul 3, 2026

“It's just a cheaper way to spec. I mean, like this is the thing is like, it's still expensive to get public. And there's a bunch of people who want to be public for cheap access to capital. I've actually looked into this and like, honestly, like buying a penny stock is like cheaper than the cost of the lawyers and the…”

Sam Lessin, Apr 17, 2026

“The reality is there's all sorts of like covenants and deals that go into these types of situations where like, if you really want to be wonky about the finance of it, it's pretty hard to lose money. And there's a ton of asymmetry on them, right?”

Sam Lessin, Apr 17, 2026

“shorting in anything where infinity is possible. And even I believe there's some crazy case where there is infinity possible. You can't short that. That's the only way to lose infinity money.”

Sam Lessin, Nov 28, 2025

“Yeah, that's the, that's the Trojan horse is everyone needs a camera. And like, I've tried buying like standalone cameras as a solution, but honestly the iPhone cameras is so good. It's like, that's what, that's what keeps you going.”

Sam Lessin, Nov 21, 2025

“I do think for those people out there watching, like, if you ever need to make a change that's hard, just call it a simplification. No one can argue with a simplification, and you can do whatever you want.”

Sam Lessin, Nov 14, 2025

“The whole thing about one-time hits, they don't really matter. Like anyone, it's like, I think this is the same thing with like, these outages, a lot of things is like, systemic things people care about. One-time hits, it doesn't, it doesn't, whether you're spending a hundred billion dollars you shouldn't have Spent on…”

Sam Lessin, Oct 24, 2025

“It's like, I just think that's, like, the way these things go is, like, it's the temperature rises, you get paid less for just technically performing anything, right, or anything.”

Sam Lessin, Oct 24, 2025

“If you like aren't dialed on your new user experience yet completely, and there's something to learn, you don't want to like give people a bunch of shit and then they don't know how to use it and they get mad at it.”

Sam Lessin, Sep 26, 2025

“if the world, you know, shrunk to a pinhead and was super globalized for a period, we're now kind of refracturing. And, you know, then you think about trade routes. You think about who sits on those trade routes, who brokers them. It's a very powerful position to be.”

Sam Lessin, Sep 26, 2025

“The general story is you don't really have a login because of any one service, but there's just, like, so many little services that, like, as a bundle, you're stuck on the platform”

Sam Lessin, Sep 26, 2025

“It's actually not about the dollars and cents. It's literally about this, like, meta power game of thrones.”

Sam Lessin, Sep 26, 2025

“Mimetic Warfare is about having an idea that you want promoted broadly, and you don't actually tell people the idea. But you give them a template and then show examples why if they copy and extend the idea easily and give them the tools to do that, they can garner the expression and love that they're looking for and…”

Sam Lessin, Sep 12, 2025

“The whole thing is just because AI is a cool product doesn't make it good business.”

Sam Lessin, Aug 15, 2025

“And like, you know, I think with the, the, the, the follow on of the internet, what happens with that is it forces everyone towards the fringe of weirder and weirder stuff to right size communities. They can be the best of blank and whatever. And so you end up with like these, like, instead of creating community…”

Sam Lessin, Aug 8, 2025

“the basic mentality, and this is a long time ago, was that basically, after someone had about ten million dollars, it was super hard to retain them with comp, right? And so like, there was kind of this, people had this like HRE type number, which is like, All right. Like after that, it becomes really difficult. And so…”

Sam Lessin, Aug 1, 2025

“it's now easy to make a demo video that's hilarious of a product that you're never going to fucking ship and like is never going to make money. Like that's not actually fun. That's just silly.”

Sam Lessin, Jul 25, 2025

“what you're describing is the classic failure mode of new technologies. Which is, you start out, you're a B to C company, which is, I am your agent. And the agent's like, fuck, you're just making more work for me. And then you're like, no, no, no, we're a B to B to C company. We're just going to train the assistants.”

Sam Lessin, Jul 25, 2025

“one of the best ways to get information or like learn things is to post random shit on the web and let people correct you. Because people will spend an infinite amount of effort correcting.”

Sam Lessin, Jul 11, 2025

“There's, like, a tone set by the network and, like, the community, and then whatever that tone is, it will just accelerate, right? Because people feed on each other, right?”

Sam Lessin, Jul 4, 2025

“You throw your fancy party on your yacht, and you throw a rager for the people of Venice, and they're fucking thrilled. But you can't just, like, totally not do that.”

Sam Lessin, Jun 27, 2025

“Like when you announce like a visual redesign, which I agree, Dave, I've been through them. They're awful. Like it's the worst experience to redefine a lot of services, a huge amount of resources. You almost always tank your numbers when you're doing it. Like, it's just like a bad, it's like, it's a heavy lift.”

Sam Lessin, Jun 13, 2025

“basically, the problem with AI is, is devalued filters to the point that everyone looks hot. So that's no longer a game anyone cares about. So now you need to do things that are, like, undeniable, like, that are harder to fake to prove and spend more money and more time.”

Sam Lessin, Apr 25, 2025

“Yeah, it's like if you're canceled first, there's just like, you're completely unhinged. There's nowhere to go.”

Sam Lessin, Mar 21, 2025

“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.”

Sam Lessin, Mar 7, 2025

“What happened in layer ones is that basically it became too obvious and all of a sudden all the fancy investors with lots of money figured it out and they started bidding up and taking all the value appreciation in the private markets pre-token launch. Right. So all of a sudden you can buy in as a retail investor, but…”

Sam Lessin, Feb 7, 2025

“Well, every single one of these things, it's, again, I, I, I tweeted about this days ago and everyone's been like, it's just, it's a very effective media strategy. Just do more shit, right?”

Sam Lessin, Jan 31, 2025

“It's like any war where like wars spur the innovation, and then 20 years later the thing will pick up your socks well, but like right now we're in the C-Four era.”

Sam Lessin, Jan 10, 2025

“it basically is just content with a different index into it.”

Sam Lessin, Dec 27, 2024

“whenever people are excited about infrastructure, beware, right? Like infrastructure should disappear. That's the point of infrastructure. And it only gets exciting once it's gone.”

Sam Lessin, Nov 8, 2024

“No, I actually think this is very on trend, which is now that with face filters and we're looking good, the new good is to look Bad. Right? Like that's like, that's just how culture works. Right? So this is why like all the kids on Instagram now have shitty photos with look terrible and like Polaroids.”

Sam Lessin, Oct 25, 2024

“Yeah, I think this is actually one of the deep secrets to Amazon, is like, for low-cost items, I had this problem with a screwdriver the other day, it's so fast, That it's like just easier to order another screwdriver than to find the screwdriver you already own, which I feel awful about.”

Sam Lessin, Oct 18, 2024

“Well, there's even longer stuff, like the Game of Thrones serialized, goes on forever type shit, which is like a thousand hours, and then there's like the TikTok, but the middle drops out, right? And movies as a format is the middle”

Sam Lessin, Sep 27, 2024

“you are seeing a lot of rights offerings or people doing cram downs. And look, why? It's like a bunch of old funds are in. The thing didn't work. There's a pivot. The funds don't have any money to support it. Someone new comes in and thinks there's value and says, fuck you guys, get out. All's fair in love and war. And…”

Sam Lessin, Aug 23, 2024

“In every generation, what happens? It's like you have a bunch of new people coming into society that are the youths, and they have this really interesting thing. Which is, they, they don't own anything, and like, they have no equity, and they have no control over shit, right? And so the, the youth counterculture…”

Sam Lessin, Aug 16, 2024

“the thing about virtual space is because it's frictionless and free and global, you can have incredibly niche interests that can find their own pocket and go in their own corner and discuss random shit and get really into it. Whereas If you're going to be in physical space, the friction's so high, you kind of need to…”

Sam Lessin, Aug 16, 2024

“the reason that this one dollar piece of metal is a 110 dollars on Instagram is because someone had to pay to make me think I want it, right? It's all about reaching the audience, right, and incepting the demand. That's the expensive part of this shit at this point. It's not actually fulfilling it.”

Sam Lessin, Aug 9, 2024

“it's just the cycle. It's like your home out competes your shitty office. So then your office has to get better. Right. And then you're like, cool. Now my office can out compete. You're like, oh shit. Now it's your home has to get better. And like people just ping pong generationally.”

Sam Lessin, Aug 9, 2024

“It is not bad that at least there are tech leaders now on both sides, right? Because that will create at least some leverage and lobbying power on both sides because there are major tech issues and regulation afoot.”

Sam Lessin, Jul 26, 2024

“It's like, actually there's nothing, if there was a thing that was 80% as good as OpenAI and just as easy to use, we get a ton of use, right? It's just like people don't think with true zero to one startups in mind, except for OpenAI, and they did a nice job with that.”

Sam Lessin, Jul 26, 2024

“I think this is one of the unintended consequences of the rise of pickleball, which is the most ridiculous sport, which is, it just, this is kind of what happens. It's like, you get like a snowboarding, and then skiing gets really good, because you're like, fuck this, this is actually a stupid sport, but like, let's…”

Sam Lessin, Jul 5, 2024

“What they got right was basic auth. Huge business. It's, it's like hilarious because like this goes back to the whole thing. It's like this. I think sometimes big companies get this really wrong and like open AI actually to your point about Stripe kind of gets it because they kind of have a little more startup DNA is…”

Sam Lessin, Jun 28, 2024

“TikTok has shown us what the true north is of engagement. I think that is like refined sugar and you can just keep refining it.”

Sam Lessin, Jun 21, 2024

“there's just this massive bifurcation of companies that are being designed to go public versus companies that are just incredibly good to own.”

Sam Lessin, Jun 7, 2024

“the job of technologists is not to just simply read science fiction and say, well, that's cool. Let's build that. That's easy, right? Like science fiction goes way out in the future, has cool ideas, And the JV version of product management or building is you're like, well, I'm just going to take these things in science…”

Sam Lessin, May 24, 2024

“It's like, this is literally just content moderation, two point out on huge steroids.”

Sam Lessin, May 17, 2024

“There's information that lots and lots of people know. The clearing price for that information is precisely zero. Right? Like if lots of people know something, it doesn't matter how it gets on the internet or if open AI bids one cent for someone to tell them an answer to something, the clearing price is zero. And then…”

Sam Lessin, Apr 12, 2024

“the absolute best thing a founder can do is call it and like pivot hard or shut it down, figure out who wants to be on the boat and get off and be honest with employees because it is like, from my perspective, I don't care about the money. The money is the money, but it is like a real sin To knowingly waste people's…”

Sam Lessin, Mar 22, 2024

“There's nothing you are good at all of a sudden because the communities went from being locally bound and physically bound to infinite and digital. And in that world, what you're seeing, I think so much is explained by this because I think what you see is one, people can't find meaning because they've lost that easy…”

Sam Lessin, Mar 15, 2024

“It's like comedy is so cheap to make that it's so high margin, right? Like, that's kind of the beauty of comedy, right? Is like, you think about like staging like a Taylor Swift show versus some dude with a microphone, right? It's like, oh, the microphone guy is going to crush it on margin.”

Sam Lessin, Mar 8, 2024

“The answer is, three percent is for payment processing, which is about what you pay for payment processing.”

Sam Lessin, Jan 19, 2024

“It always starts with porn, right? If it actually works for porn, then like, it's a thing, right?”

Sam Lessin, Dec 1, 2023

“I mean, the reality is people who, like, what the writers should be doing is building a rabid fan base around them and a specific niche that they own, where those people are gonna trust them, they're gonna, like, hear from them, they're gonna, like, care what their choice, like, they're gonna be curators.”

Sam Lessin, Nov 17, 2023

“the fact that this thing is easy to make is not, in and of itself, make it a compelling product.”

Sam Lessin, Nov 10, 2023

“we basically have ended up in this weird place where, you know, industry has the dollars and the will To do a lot of, like, really big picture research, which has historically not been true, right? Business has been like this application layer thing”

Sam Lessin, Nov 3, 2023

“to make a social part of that work, yes, you have to be in Dave's list of the top 10 product people in the world, but you also need incredible luck and incredible timing. And like, it's not clear that just because you did especially social once properly and got it the right timing and the right product that you have…”

Sam Lessin, Oct 27, 2023

“And so when infrastructure gets sufficiently boring, that's when you should be building on it.”

Sam Lessin, Oct 27, 2023

“in times when trust gets eroded in the public, you know, places for, for news, that the elites all retreat to very expensive newsletters.”

Sam Lessin, Oct 20, 2023

“Yeah, it depends that you're defending the floor or you're trying to win, right? Like, this is like, defend the floor, be boring move.”

Sam Lessin, Sep 22, 2023

“most of the things I out of the gate thought were working ultimately didn't. They're the things that I had fundamental beliefs on and every single thing that I feel really proud of investing went through a several year period because we go so early of like, oh fuck, this thing's probably dead.”

Sam Lessin, Sep 1, 2023

“the biggest sin to any of these networks is artificial promotion, because you end up with a bunch of people that are actually not interested in your contact and orthogonal to what you want, and it makes the experience absolutely terrible for you.”

Sam Lessin, Jul 7, 2023
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