More or Less Podcast

Sam Lessin — Selected Quotes

It's much more, it's much more cynical than that, which is basically in the early internet, you had Google and Facebook, which had two things. One is they had explosive user growth. had unbelievable. They had all these amazing, they were also unfucking believably good businesses, right? From like a fundamentals perspective, the costs versus the potential that monetization was like off the charts. Good. Right. And a lot of people of our generation experienced that. And it was like the most exciting, most amazing world changing thing you could possibly experience.

— Sam Lessin, Episode 93

So here's the more or less contest which is Dave and I are putting together our invite list for an annual pilgrimage to ski big lines in Alaska. And we're like who's on this trip and who should we invite? And we're like should we do a more or less promotion to find a fan who might want to come for a very special more or less session?

— Sam Lessin, Episode 67

It was the most predictable startup failure you could imagine. And it's just shot. mean, the question for me is why, who even paid $160 million for this piece of shit?

— Sam Lessin, Episode 87

right? And you know, unfortunately, if all the money was designed for public company financing, it kind of fucks up all the media companies until it fixes it, until they fix themselves.

— Sam Lessin, Episode 50

You know, it does, it's more fun, it's more dangerous the whole nine yards, but like my kind of net on this whole conversation is actually where we started, which is like the incumbents are going to crush it. Like GitHub is going to crush it. Because if you think about like the real places where there's leverage and blockers, right. It really is going to be like, who's actually deploying my production code. Cause they actually know it's up or like, who knows? I don't care what people say. I who's actually using what in what cases in production. And like people like GitHub know that right. AWS knows that like, you know, the,

— Sam Lessin, Episode 100

and they started bidding up and taking all the value appreciation in the private markets pre-token launch. So all of a sudden you can buy in as a retail investor, but you can't buy in at a low market cap, you can't be an early believer. All you can do is be in late and there's no appreciation value. And so interesting, this is the point I wanna make, which is.

— Sam Lessin, Episode #85 - Take 01_67a508fc24f2a63a2b06e1af

right, sitting on DEXs and crypto exchanges. And they're like, they get and it gets momentum, right, as like a thing. And why it's like, well, these kids are not going to earn their way to the good life, right? Everything's about asymmetry. This is like a really interesting, fast moving community grows super fast, right? And they get the numbers get ridiculous and huge and people like, wow, what is this fast burning? Now the real question for value as an investor versus a trader is, is there staying power to that community and meme and what happened interesting was this Melania token.

— Sam Lessin, Episode 83

Well, it can also balance between them or like optimize between them, et cetera. Yeah. just, I just, honestly, I think it's a better interface. Like it's less brittle. find in a lot of ways you let them handle all the weird connections to different things. Right. now I do think like long-term it's one of those ways where like, look, the idea, like back in the day, when I started my first company with drop.io, like we had this whole vision about routing storage, the cheapest storage providers that turned out to like not matter or be a thing. Cause it was like, nah, it doesn't that much.

— Sam Lessin, Episode more_or_less_indian_wells_2026_03

Yeah, but telegrams, telegrams. You just, it just sits for me, telegrams that just sits there in telegram. And I'm like, what's the news? And I have it trained to go read the New York Times, the Wall Street Journal and the information and everything. Just give me a great summary. I have it trained to a continuously update. have a list of, I had to build a list of the hundred elected officials that battered in the U S and the best. I have the tech people like, what's the vibe? It gives me the Democrat vibe. It gives me like all those things saved in the Postgres for me.

— Sam Lessin, Episode 135

But you clearly read the memo, which is just say shit on the internet, right? And then someone, and like create controversy and people will know your name. But he's trying. The one I heard is, have you heard? And there was a great, the other one I saw, I only saw this in passing, but someone wrote a great article, I don't remember who, cause it's the internet, about oh Eric Adams. I think that's his name, the mayor, the current mayor of New York, right?

— Sam Lessin, Episode 112

No, it does because the ad looks like a fucking Halloween the black and you've read an orange looks like a fucking jackal. Yeah

— Sam Lessin, Episode 116

It's, yeah, that's like, and that's fine, but like someone's gonna be the Billy Bean and find like the kids who are like savants. It's like some savant. No, cause they have, you need like someone who's like, someone like, and he's like, they're gonna find the savants who like, you know, have one arm or like don't know how to count or like, you know what I mean? Like all the misfit toys and pay them like 100K.

— Sam Lessin, Episode 106

So what they, yeah, all the CS comes in, which is basically where they make the money. And what happens is they'll be like, hey, OnlyFans model, we need you to take a bunch of candid pictures, like in a car, you're shopping. Like just take tons of candid photos and they have like basically a content library. And then they're like, oh, guy37 messaged and asked what you're up to. And like, well, take that content image and say something cute and send it back. And the person gets to pretend like they're actually interacting with a real person. This is like as straight up the middle AI.

— Sam Lessin, Episode 101

Really? I just don't give a shit about the personalities. It's so funny. Like I think this is maybe like where I'm like a psychopath 'cause I truly don't care.

— Sam Lessin, Episode 151

So we've, so yeah, the answer is people have definitely asked that. And here's the way I look at this, which is, think, I'm actually curious, but this is the way I think about it, which is there's some similarities. Like people have tried to do 360 deals before, right? In history, but here's the really big difference, like an all encompassing deal. Like you do a deal with someone for like a whole footprint or like their brand holistically. Musicians happens. Here's the big difference. I think this is really important.

— Sam Lessin, Episode 86

I mean, there's been a bunch of the story has been like the big business stories has been thing you don't know about that everyone's now using is going to become a big company. And maybe there's an IPO, right? The real but the real game, right, is going to be like the princely states effectively and like how they the backroom, which by the way, if you go into the history of information businesses was literally the original paid newsletters, right? We're like the Italian newsletters covering princely states for high priced

— Sam Lessin, Episode 118

There's nothing I mean, guys, our my, my, my eight year old loves this idea. He was like, Sam, he's like, Dad, you're selling it because I took him to Home Depot to do rock sourcing. And he was like, so let me get this straight. You're going to sell this for $200. And I'm like, yeah. And like, so he's very excited about business.

— Sam Lessin, Episode 97

Oh, I have to go because I'm super late to a meeting, but I will say one last thing, which is for this group, but people don't care. First of all, I've been messing with DaVinci resolve more and more. Fucking great. Second, we should, it's yeah, it would just go, it's so good. And I actually think the new workflow of just like downloading these and then clipping them up on in resolve is the way to go. I got to go, but I'll leave you on that. Bye.

— Sam Lessin, Episode 61

it's expensive watch not a it's also not that expensive, medium expensive. But the basic point is that like, now that I'm watch unsealed, and I only get ads for watches, every, I get the same watch ads, and there so many watches. And so like, by the hundredth time you've seen a watch like, I'll just buy it. So now I bought like two other not expensive watches like less expensive than this watch. And I'm like the steel. And the thing about it is like, I just feel like this is a really deep, emotional in touch experience of like how

— Sam Lessin, Episode 120

There's nothing. It's nothing. Right. And so the basic point is that people watch TikTok, they subscribe to soccer players on Instagram. It's not like that sports isn't in the culture, but the actual live viewership of these things, which are so valuable is like completely demented.

— Sam Lessin, Episode 89

Well, Peter, can I push you on that? That is the maybe you're in my narrative, but there was a study I saw recently that said that AI is so hated, it's actually hated more than Jeffrey Epstein by the general public, right? It's like, it is absolute... It is the worst brand, like you could possibly imagine. No one trusts it.

— Sam Lessin, Episode 162

is about money making. Whereas I think the problem with like most other presses, people think that like the mission, their actual purpose is because people have very little to say on social media. And so they need things they can clip and repeat and say on social media that are pre-packaged for them. So it's really, which is not, 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, Episode 88

and the coin toss of whether it pays off or not is so favorable 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. And I think the same thing is true. You know, if you're an Apple investor, you're like, what are you worried about? You're worried about supply chain, you're worried about cost of labor, you're worried about partners. So if Apple's like, hey, we're going to plow $100 billion in your robots, you're like, thank God, like, I'm happy to pay that tax.

— Sam Lessin, Episode 54

Speedrun is a concept from video games. Well, it's speedrun things. You know how people try to do Mario in 35 seconds type thing? That's what a speedrun is. And I'm pretty sure the original concept was to do video game incubation. And then they pivoted it this season to be like, season, this year to be just a fast incubator. I've been with a few companies.

— Sam Lessin, Episode 120

Oh, I agree, but I think that's like extreme. That's like in that the devil's in a default, but the default also like is like easy. I think, right? Like I think once you have that stuff in place, you can frame it. Do you like safe apps with an American flag, right? Or you're like dangerous apps. Like Apple already does this. They already, they already do crazy stuff to like limit their app store all over the place from quote unquote dangerous apps. So we just need Apple to step up and Google to step up and create one more level of.

— Sam Lessin, Episode 37

X, Twitter. Look, the reality is, yeah, mean, here, here, here. It's Twitter. It's Twitter. mean, like, again, you know, I have all people don't love all the things that Elon Musk does for a whole bunch of reasons. Um, I also love some of the things he does like SpaceX and Twitter was just such a fun punching bag for so long. The reality is for 40 billion bucks.

— Sam Lessin, Episode 78

Oh, that's interesting. So this is a China ban strategy. I like that. I like that. You're funny. So your thesis for 2025 is China gets banned. so Americans are there hand stitching their Ewok hats and selling them one at a time from their from you are they are they using the putting out system? Is it like the 1817 10016 100 is England early and

— Sam Lessin, Episode 78

I did too, what a disappointment. They're like, you're so, it does work sort of, where like this is in California, a trial. I'm like, thank God I can finally get my license on. I constantly lose my wallet. In fact, I don't know where my wallet is right now. And like, and then I had to get, I actually recently had to go to the DMV and get another license because I lost my wallet with my license. And then someone found it, someone found it in the underneath the seat of a Cirrus SR20. I was flying and sent me home. So now I have two licenses, but.

— Sam Lessin, Episode 49

Well, it does. I'm just shocked. I am shocked. I mean, to the AOC voting against, right? The story that I have been told over and over and over and over by smart people who have said, yes, Tick Tock obviously is a national security plant, obviously needs to be banned. There's no way that the Democrats will do anything before the election because they want every last scrape and vote they can get out of the children and like the children like Tick Tock. And so like it's just not worth it because they're so worried about Trump winning the election. The fact that like Biden is like clearly just being like

— Sam Lessin, Episode #38: Hartz & Minds_66cc4b089d6d7a010022af1a

I saw someone post on the internet proudly that this was like their 20th CES and I was trying to do the math. I was like, you spent what? 40 to 60 days of your life at CES? That sounds awful.

— Sam Lessin, Episode 81

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