Sam Lessin on Venture Capital & Investing

Essays

From the Podcast

All right. So Dave, here's the funny thing. One, it is narrative capitalism because the SaaS thing was a fucking narrative, right? The narrative is you acquire a user once, and they'll pay you forever, so it's an infinite LTV, and that was the narrative of the SaaS era, which collapsed.

— Sam Lessin, More or Less Ep 161

There's no heart needed. You take Vimeo, you buy it. It's a great business if you operated it properly. You, like, buy it cheaply, you consolidate customer service, you make a shitload of money, right? It's awesome. I do think, like, SaaS is crushed. It's cool they've negotiated this out. I actually don't know the details. I haven't spoken to Howie about it at all. My sense is, is that Howie gets to go operate the AI company he actually wants to operate. And as a Bending Spoons shareholder, I'm very happy. Now, as an Airtable shareholder, the write down from where everyone had it marked, the big fancy people, is pretty brutal. And I'd also say that, like, the amount of capital it took them to get to this outcome is not my favorite, 'cause there's a lot of dilution, but, you know, it's something.

— Sam Lessin, More or Less Ep 161

This is the era of bag securing. Everyone is trying to get their bag right now, and whether that's, like, a big amount of private capital or selling your company or whatever, everyone is in a desperate... I, it feels like musical chairs. We're in a musical chairs era. Everyone gets it and everyone wants their bag. It's the line from, uh, I love, what is it? It's not The Big Short, it's the other one. The CEO of the bank comes in and he's like, "I'm not paid 'cause I'm the smartest." I'm paid to know one qu- thing, which is where the, what music is gonna play, and right now I hear silence.

— Sam Lessin, More or Less Ep 161

Yeah, yeah, 'cause you click on things on Instagram, and then you end up... But here's the funniest thing. I'll, I very frequently will double post. I'll post things on Threads and X at the same time. And it's really funny because on Threads, Threads is so left wing. It's, like, wild. Like, anything I post there, like, I will have the left wing, far left communist mafia after me, which is funny because, like, Threa- because X is actually right-leaning, at least in my purview, right? So you have, like, this very funny thing where, like, you can post it, you can, you know based on what you say and who you wanna antagonize how to completely flip out Threads with anything that's even slightly right-leaning or pro-capitalism, whereas, like, X is, like, all that. And so it is a really funny thing. But overall, like, I think X has never been stronger. I think it's a great product right now.

— Sam Lessin, More or Less Ep 160

I agree with that. I mean, like, look, it's just like Star Wars. There's a dark side of the Force and the light side of the Force, right? And, you know, in some ways, the dark side is easier. Certainly easier message to sell and raise capital against and a bunch of other stuff. But ultimately, the light side of the Force, which is this is, like, how you do it for good, is a, I think, hopefully, ultimately victorious in the longer and, and the better message. Uh, it's just harder for other people to pull off. I mean, I think it's very easy to sell the negative story, especially in a place of non-incumbency. I think Mark is one of the rare leaders that actually is in a position as a founder at a trillion-dollar scale who already has all the people on his platform who can try to tell the light side of the story, is what I would say. And they're, look, they're probably both true. Like, the Force does have two sides, you know? It always does.

— Sam Lessin, More or Less Ep 160

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

— Sam Lessin, More or Less Ep 157

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

— Sam Lessin, More or Less Ep 157

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

— Sam Lessin, More or Less Ep 157

Look, she can do whatever she wants. Capitalism says she can do whatever she wants.

— Sam Lessin, More or Less Ep 157

My kind of personal take on it is, like, it's a complete fuck you to capitalism in a way that's awful. But here's the interesting thing. What I said is, "You can't hate the game..." Uh, I'm sorry, "Don't hate the player, hate the game." 'Cause here's the thing. The real story of this-

— Sam Lessin, More or Less Ep 157

Clout was f- no, but clout, clout was so fucking stupid. Like, clout always annoyed me. It was, like, such a, like, misunderstanding of how social capital works, like, so fundamentally. But people liked it 'cause people liked scores.

— Sam Lessin, More or Less Ep 158

I do think it's funny. Like, I actually think this whole thing is, like, pretty interesting because I do think, like, look, Sam Altman is an incredible storyteller, an aspiring Elon level storyteller I would say, in terms of, you know, narrative capitalism and using that for cheap capital. The Jony Ive acquisition thing, especially if it just turns out to be an Alexa, is, like, particularly interesting for this 'cause it was one step along that line of like, "Oh, I'm buying, I'm gonna pay a ton of money for Jony Ive because it will make- Raising more capital cheaper, not more expensive. So it actually, even if it costs a billion dollars on paper, is free to negative cost acquisition just on the brand of Jony Ive, which is an interesting thing.

— Sam Lessin, More or Less Ep 158

Yeah, yeah. It plays out capitalist, but I think, I think it's very cynical for these companies to even try to switch the field of play from business to politics, right? Like, I think that's a very cynical, anti-American thing to do, to be like, "Okay, we're not gonna play and compete in capitalism in a fair and open system. Instead, we're gonna, like, switch our venue to regulatory capture because it's the only play we have." And I get why they do it, and, like, to some degree as businesses, I don't grudge them the play they need to make. It's, like, the classic you can't win the game, so change the game. Um, but it's also just a bummer, right? 'Cause you're just like, man, like, politics sucks, and, like, business and economics are awesome. And, like-

— Sam Lessin, More or Less Ep 158

And like, so to me, like, and weirdly enough, I mean, there's even like a weird argument about, oh, would you stop American open source models 'cause that's technically our domain for me to develop, but not the Chinese one 'cause that'll cause a trade war. Like that's insane, right? Like all this shit's just insane and doesn't map to how like capitalism or like the internet works, right? And that's what I object to.

— Sam Lessin, More or Less Ep 158

That's what it comes down to. This is what I don't like about our moment in history, is I don't think we're playing capitalism anymore. Like, I think we're playing some like, like political capture game that is way less interesting than capitalism, right? And so that sucks, right? And like we should compete in fair and open markets as much as possible, and the best team should win and whatever. And, and like now we're just in this game of like people, which is again, it's, it's sto- it's been stories for a while. AI is scary, blah, blah, like all these types of things. But now we've kind of moved to a new version of the game, which feels much more desperate, right? Which is like, man, we better like get some regulatory capture going, 'cause otherwise we're in trouble.

— Sam Lessin, More or Less Ep 158

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