Sam Lessin on Business Models & Strategy

Essays

From the Podcast

I mean, I did it, but I think for me, it's like the story of open AI is like the business model go round and round of like, what did it, how they're going to make money.

— Sam Lessin, More or Less Ep 140

This is probably Hollywood's new business model is basically betting on the things they make. Like you make the movies for free.

— 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

Well, think dark, like dark pools are basically here's my, here's my, here's my dark. Here's my, here's my, my, my thing. I've talked to a bunch of companies recently. I've been thinking about a bunch of this from a bunch of different angles. I actually think one of the things that LLMs and this arrow will do is going to be the death of the open marketplace. Right. Because you can't make any money in an open marketplace. It's too efficient.

— Sam Lessin, More or Less Ep 139

CRM, it's so good. It's so good. There's a stuff you doing six months ago, you had to manually patch. Now it just understands how to... But it's just too easy. No one's going to build a company doing any of this stuff because it's too easy to build. There's no software defensibility to any of it. So you just have to be really pure on business model and why it is that you're have a compounding advantage versus you did something... that was quote unquote hard that a customer asked for and that's somehow valuable. I this is my number one rant. I've had several meetings this week where I feel like people are still stuck in the old model of building companies where they're like, I'm like, what are you working on? They're like, we did this. I'm like, why? It's like, well, we talked to the customers and the customer said they wanted X. So we built it for them and now we'll sell it to them. I'm like, no, you're not going to sell it to them. They might want X.

— Sam Lessin, More or Less Ep more_or_less_indian_wells_2026_03

Yeah, they're just going to speed run. Just like with everything that they are, you're just speed running all of history all over again, right? Like experimental budgets, the real budgets to like buy whatever it's like everything just speed running, you know? So yeah, like there's no way it's not the idea. Like the whole thing with SaaS, right? Was everyone was like, this, once you acquire a customer, they're infinitely valuable because they will never cancel and subscribe forever to this thing. And so like, they could like spend all this money, but That turns out to be bullshit, right? And like, it'll the same thing I'm gonna do with this. It's like, there's just general intelligence. It's low margin. It's, I mean, it's great. I'm like literally building stuff as we talk. I'm like into it, but I think it's a terrible business.

— Sam Lessin, More or Less Ep more_or_less_indian_wells_2026_03

not because honestly, I'll be honest, it's exactly the type of thing that 10 years ago, I would have gotten super fucking excited about, right? And like, I would want to build I'd be like, Yes, of course, the future of human small business marketplace, like it's it says all the words I like, right? Like all the words I like are packed into this. And like, so you're like, of course, I want this to work. But then Sam of 2025 is like, you have a business, right? And like, that's where I'm like, I don't see it, right?

— Sam Lessin, More or Less Ep 99

And like most of the beds are the same, right? And you're like, whatever. It's like a marketplace. There's a scale to it. It's like bound. This is much more like, yes, people should be able to build these businesses, but they're the tip of the spear, the brand and the identity, not just like.

— Sam Lessin, More or Less Ep 99

There's a whole bunch of businesses to build there, but it feels more Shopify-y to me, right? Where like the value is based around the identity and the brand and the person and the influencer is the unit of value. It's not like a clear to marketplace where like, it's kind of like, you know, I don't care what the fitness person is, just give me a fitness person in Austin, right? Like, so I that's like the big challenge when you get into the details here is like, it's not actually, Airbnb is like, I need bed, right? And like,

— Sam Lessin, More or Less Ep 99

Um, and for what it's worth, I actually think that this in general, the service marketplace makes a ton of sense for creators. So for instance, if you are like. An important creator, you are like some fitness, IG influencer person, and you live somewhere and you're like, I want to make more money saying that, well, my business's courses, my business's subscription, my business's live events, by the way, I might host trips, right? Saying, Hey, I'm going to take a trip to Tuscany with some fitness influencer for yoga. And you sell it as a package deal.

— Sam Lessin, More or Less Ep 99

That's not good for them. The fact that she has a lot of availability. Look, so, so I actually agree with Jess very fundamentally here, which is like, is a great first principles idea, right? Like if you're sitting around like in Silicon Valley being like, how does the future work and independent contractors and small businesses and brands. you're like, Oh yeah, obviously like liquid marketplace for all the services. Like it makes total sense when they launched it, I was excited.

— Sam Lessin, More or Less Ep 99

It's not Facebook. It's not Google. It's not a good business, right? Like that's the big difference is you just have to understand the business model on these things. like, not all things that people like are good businesses.

— Sam Lessin, More or Less Ep 93

Look, here's the interesting question, Dave. I think there's two types of VCs that are very different in the world and two different investors. One is the kind of product led product, product, product dominates everything else, right? Then there's like the business people, right? Who are like the quality of business model really fucking matters. Business, business, business. Product is an important input. You have to understand that you have to follow it, but it's just an input. I obviously represent in this conversation, the business quality, the business matters, right? The quality of the business matters, et cetera. Now, that doesn't mean that prices don't get run up.

— Sam Lessin, More or Less Ep 93

There's no, there's, there's no amount of money. Like I think, I think the actual business model is the opposite. No, I think the opposite, the business model is the opposite, which is you go to the guys and you're like, look, here's the deal. We have this new awesome feature where the Brit feature where you can see what other people you can like impersonate anyone and see their feed, but only in premium mode. Can you stop someone from impersonating you? That is the thing that Dave and I would pay a lot of money for.

— Sam Lessin, More or Less Ep 90

Right? Like I don't even, I don't care what the business model is. Right. And like, so I do think there's going be a super cycle. If you'll be like, I kind of like that thing. I'll just bring it back in various forms. And then some people will be like, look, it's time to like backfill, you know, the piece of the internet that got taken in a different direction. Um, who's going to rebuild Yahoo.

— Sam Lessin, More or Less Ep 89

Tweets