Sam Lessin on Startups & Entrepreneurship

Essays

From the Podcast

I just don't, I don't, I don't think that's gonna, I mean, my personal view is this is the real conundrum is Dave, what you're describing. I love entrepreneurs too. I obviously backed them. I think they're great. Let's pretend I am not worried about the top 1 % of anything of intelligence, of drive or whatever. They're going to be fine. They're going to figure out how to build cool businesses and things on top of platforms will make it easier and more efficient for them. Whatever. I think the question is what happens to the P 50 P 75 people, right? You're smart. You're not the smartest. You're driven. You're not the most driven. There's like, that's most people by definition. And the problem is, is that of all of a sudden, I don't need anyone to build my super good idea. I can just do it on my own, which is super fun for me. Then the problem is, is that like, it creates this dynamic where like, I actually do think it's a real problem. It basically says that if you were exceptional, you're going to do great. And so the question is, your only option is to try to create an economy where everyone is an exceptional at something. And therefore everyone can be in the top 1 % of what they're doing, which I think is extremely difficult to do. Or you have this fundamental problem, which is you just need so many fewer people and so much less labor, both physical and mental to do anything that you don't take anyone along for the ride.

— Sam Lessin, More or Less Ep 139

You can't make any money on those. And the reason you can't make any money on those is because with open access, someone will always overbid or overprice. It just doesn't work. So it turns out that when markets get too efficient, they're bad businesses. And technology and AI makes markets efficient. The only way to have a good business, the only way to do a good venture deal is to have proprietary deal flow. You need a dark pool of deals that no one else knows about or dark pool of founders that no one else knows about or access that no one else has that's sustainable and ideally compact. And I think we're going to see this in a lot of things. We're like, the internet was all about bringing liquidity to marketplaces saying, okay, there is this inefficient market and we're going to make it more efficient and make money on it by effectively aggregating demand, supply and demand and hosting the market. I think that goes to zero value because it's too efficient and everything becomes in a company building sense about forget the software, forget the market story. It's all about can you own and control dark pools of value effectively? and then monetize them consistently.

— Sam Lessin, More or Less Ep 139

It's just power though. It's like, don't, hear you David, like I was with another entrepreneur of ours recently who's spending hundreds of millions of dollars a year right now on like all the LLMs, right? Like they, yeah, they're spending hundreds of millions of dollars a year run rate on inference, right? And

— Sam Lessin, More or Less Ep 139

Like you have nothing and like, I applaud our willingness to act. So it kind of like, it's, know what it is? You know what it is? It's kind of like, you know, I was talking to some entrepreneurs the day, but like, I think this is kind of a Silicon Valley narrative that's been built up and people keep repeating, which is not like the future belongs to people who just do shit or like take initiative. Right. think that is a hundred percent true. It's like, when you're looking for people to hire, you'll people work with it's like.

— Sam Lessin, More or Less Ep more_or_less_indian_wells_2026_03

And so we were talking to a bunch of entrepreneurs and saying, hey, just do us a favor and give us kind of like some nice things you remember about us and our interactions and found it. And so you basically, had two days of people being like, and LPs saying nice things on camera with me. like, this feels great. I'm like, wait a minute, I can just automate this. I can have flattery all the time, right? From characters that are in my life. And the nice part is with your real voice is it sounds great.

— Sam Lessin, More or Less Ep more_or_less_indian_wells_2026_03

If Brian Chesky had, if he had balls, they'd do a partnership with OnlyFans and they'd crush it. If they just were like, find a local prostitute, that would be easily a billion dollars, right? Like, but they don't have balls, because he's not really in founder mode, right? um

— Sam Lessin, More or Less Ep 99

I don't know. I think the interesting thing look back on in 10 years will be all these huge secondaries. Like what is the correlation? Not causation necessarily, but correlation between people taking big ass early secondaries as founders and outcomes. We'll see.

— Sam Lessin, More or Less Ep 99

I don't know. mean, it's also like this whole thing. Sometimes, sometimes founders have this thing where like they want all these fancies investors on the cap table, but they can't fit them and they can't make decisions because they don't have balls. So they end up like take trying to like fit six fancy investors in the space for only one. And it's just a negative leadership signal that you can't make decisions and like you're not a good leader. like

— Sam Lessin, More or Less Ep 99

Well, I think that does for sure happen with startups, but I'd actually argue usually when companies are getting offered that much money to the point that like you literally can't up the price reasonably and you have nowhere to put it. And you're like, I don't even think this is a responsible to take. That's usually a sign of a massively overhyped company that's going to crash and burn. Right? Not always like, no, you're just fucked. uh

— Sam Lessin, More or Less Ep 99

It really needed that G650. mean, I don't know. I personally think that's very, the question to run, which I think will take years to figure out, is what is the history of companies where the founders cashed out meaningfully early? Do any of them succeed? My bet is they don't, right? My bet is that, well, that's the question. I mean, I don't have a problem with some founder taking a few million bucks over walking around money, but if they, tens of millions, hundreds of millions of dollars early,

— Sam Lessin, More or Less Ep 99

depends how much and if they have money. I mean, like, I think the story of, hey, I'm a founder, I literally have no money, like, and I want to send my kids to private school and I'm gonna be in this for 20 years and so I need a few million bucks doesn't stress me out. But if they're already rich and or like,

— Sam Lessin, More or Less Ep 99

Yeah, 100%. Like I actually, here's the thing, I have an offer. Anyone who's on the OpenAI board who's listening to this, I'm gonna send you a free Founders Edition Ruck Rock. You tell me. Any fancy board, free Ruck Rocks on me.

— Sam Lessin, More or Less Ep 97

My friend, chat GPT to generate, um, you know, the, the workouts and kind of the videos. think it looks really good. You can see all the kind of use cases like, you might be out of a brunch with your lady friends and you have your rock rock or, know, in a board meeting, you'd have your rock rock. So the founders edition is $200. Uh, you can buy it at the rock rock.com. I've sold many actually, and I'm just working on fulfilling it. Well, the good news is that we do all American rocks, so there's no importing.

— Sam Lessin, More or Less Ep 97

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

They haven't I'm gonna say no they have not you can go either nice part of me is I write everything out so you can look at my thing from two years ago and I said the big guy platforms are gonna win and Tiny tiny companies they get more efficient gonna win and everyone else is fucked that is what's played out and you shouldn't invest in startups. I'd say

— Sam Lessin, More or Less Ep 90

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