Sam Lessin on Startups & Entrepreneurship

Essays

From the Podcast

It's an interesting company. So we funded a long time ago. We were the first investment called Sublime Security. When we were talking to the founders of this, the whole point with Sublime early on was like, look, we all know the top 10 tech companies in the world. What they do is they get on a weekly call between the CISOs, right? And they're like, "This is what we're seeing," blah, blah, blah. They're, like, sharing things.

— Sam Lessin, More or Less Ep 167

But that's a great sourcing pipeline. But it's actually not cra- Like, especially kitesurfing in that moment was a pretty smart way to do it. 'Cause you think about it, it's actually a great sport for entrepreneurs. It's a little risky. It's, there's a high barrier to entry. It selects for the right type of people.

— Sam Lessin, More or Less Ep 165

Look therememelordwhichitisinterestingisacompanywebackedithalhilariousirreverentmemegeneratorthatsrelevant toit Heres IllgiveyouoneInterestingDatapointIveSeenThisWeekAbunchWhichActuallyReallyResonatedWithMe Ivemetwithtwostartupsnow ... that no one has heard of in Silicon Valley at all, right? It's not even not generous. They're kind of just LLM wrappers for middle America, right? They're like y- they're things that... Like, they're not sexy. Like, no one here is gonna care, but they're crushing it on growth and revenue with affiliate programs, deploying in small businesses with all this stuff. And you know why? It's a really interesting insight

— Sam Lessin, More or Less Ep 165

it's funny From a first principles perspective it seems obvious that Canva would have to evolve at this moment because you're making a paperless post or making an ad and it's way better to just have an Ai MAKE IT fOR YOu AND RUN IT foR YOU THAN TO move Things arouND onA screen THiS ISThe Same PRoblem WITH Figma I had A Funny meeting yesterday With Some very Very young Founders AND I Was LikE wherE's yOur figMA SOMETHIng LIke we don't--we jusT Use Paper IM likE finEBuTthe poinT IS fiGMaAndICanVaAre thesameThingTheyhavetoevolve Ontheflipside It'skindawild OurkidsreallyusecanvA

— Sam Lessin, More or Less Ep 165

Well Look I Think it's interesting SUdSud has Built A Pretty Cool Portfolio AND THERE'S ALOT HERE'S I Have THIS Problem RIGHT NOW Right BECAUSE WE In Early Stage Investing Which Is WHICH I think You'RE Speaking To A Little Bit WHICH IS LOOK You Love Team You LOVE Theme Right YEAH LIKE IS this Person Freaking Awesome Right Do THEY REALLY Weirdly Care About THis Problem IN SOME Deep Passionate Way AND then thematically IS thIS Correct AND THe problem IS tHAT AI IS kind OF Washing IT ALL Y Combinator STARTED MAKING IT REALLY HARD TO KNOW wHat was Good AND Bad BeCAUSE IT KIND OF TAUGHT EVERYONE hOW TO Pitch NOw We'Re At ThE POINT WHERE Every Company SEEMS Reasonable BEcause it's All Passed Through Eighty Seven AIS AT ThiS Point BEFORE yOU SEE IT SO IT'S NOT ONLY The Deck It's ALL THIS STUFF Seems reasonable ANd then the FOUNDER Thing IS hard becaUSE SINCE Everyone AND their Mother nOW Wants TO Found Companies it's N O longer the Era Where it's Uncool YoU HAVE ALL THESE founders tHAT seem ReALLY GOOD AND S O I THINK WHat you Know you're Pinning TO IS YEah C I IS A Problem ThaT Gets Talked ABOUT A Bunch IN various CIRcles IT IS A PROBLEM W e Can ALL Agree thaT A Bajillion LiN EA LOT More CODE IS BEING Pushed NOW Than EVER Before AND A bunch OF Shit's BREAKING BuT tHEN YOU'RE WHO ARE yoU Betting ON AND ThemAtically WhAT Take On are you TAKing AND I don't kNOW I'M Kind OF INTO The LOok it's The RiGHT PERSON AND The RiGHtProblem I Don't EVEN KNOW the Details

— Sam Lessin, More or Less Ep 165

I do think that my understanding of the Salesforce... I mean, Marc Benioff clearly is, like, it's in- he's an interesting character 'cause in my head he's, like, not a technologist, but he's, like, an incredible salesperson, right? Like, is the interesting thing. Like, so the story I've heard, and someone can correct me in comments, I'm sure someone will, is that when he started Salesforce, it was billed as, like, this cloud CRM and this platform, but it was total bullshit. He basically went to a bunch of people and sold them each individual CRMs that were completely unintegrated, right? And they were just, like, one-off software builds, right? And, like, it was just all sales tactics, right? And so, like, it's interesting 'cause, like, in this technology world you have a bunch of people like the founders of Google or whatever that are like their resume or, like, is as engineers or as builders, right? And then you have Benioff, again has been unbelievably successful, but he's not an engineer, he's not a builder, he's a sales guy. Has the interesting distinction of being in it, but he's always getting criticized 'cause he's, like, among all the founders. He's sold stock, like, every day of his life, right? So you have these guys who, like, are like, "I'm in it. This is, like, I'm playing for keeps. I own my company." Benioff is, like, the constant sock, stock sales guy, gets shit on the internet for it. He's just a very different beast, right, than, like, a lot of what the valley is, and yet it's a really interesting s- to see him operate and still care at his age. I'm not sure I'll be caring when I'm his age.

— Sam Lessin, More or Less Ep 165

Guys, I gotta tell you, listen, the email agent thing, I was on with an entrepreneur, actually two in the last week, and he's like, "Well, I have, like, the... I call the agent, and I text the agent." And I was like, "Yeah, but email's by far the best," and he's like, "Yeah, it is." Email's sick. The multithreading of it is so good, right? I don't know. Anyone who's texting with their agent doesn't get it.

— Sam Lessin, More or Less Ep 164

So but Josh, but d- can you build a company that way? Like, with people coming in, stamping the card, getting infinite free capital for their next startup. Like, does that work?

— Sam Lessin, More or Less Ep 162

Of course. So Josh, co-founder and managing partner at Lux, which has done, basically did the contrarian thing, which has now become consensus around defense and deep tech and hard tech and is kind of one of the men of the moment for things, calling things like Anduril, et cetera, early and backing up the truck when that wasn't cool, which is now very cool, which means hard to seed invest in anymore 'cause these numbers have gotten so big. So we have an amazing gang here, and I, I have my topic list, which obviously I had my bot write, of what's going on to run through about what's going on with NVIDIA, this crazy balance sheet stuff. S- Peter, we're gonna have to talk a little bit of Airtable-

— Sam Lessin, More or Less Ep 162

So I can't exactly preview it, 'cause my other phone that I was buying things on died, but somehow these silly people have decided that I'm gonna do this pod alone. And so I have assembled six of the world's premier investors, and we're gonna do a Sam and Friends episode, and who knows what's gonna happen. But I've got basically the founders of some of the best VC firms.

— Sam Lessin, More or Less Ep 161

Why would number go up? Like, this is like, you know what it is? It reminds me of, like, the Bill Gurley thing. You know how Bill Gurley always likes to talk about how bankers rob startups because they under, they, for the pop and ba, ba, ba, ba, ba?

— Sam Lessin, More or Less Ep 161

I mean, sure. Dave, but, uh, I think Dave was my second on the deal, but, like, we had Howie over, we loved the software, that we were literally, when we were building Fin, we were using Airtable. I was like, "This product's sick. We need to invest in it. Who's behind it?" Turned out it was Howie at Etax from back in the day. I knew him from his first startup. So we put 3 million bucks in at 90 post, which Dave did support me on. It was very rule-breaking for Slow at the time, 'cause it was too far along.

— Sam Lessin, More or Less Ep 161

And, like, for some fuck... It's, like, wild. And so I actually messaged the founders of Venmo. I was like, "Guys," the actual founders, like, "Guys." And they were like, "We don't even know anyone, so we can't get you back anymore."

— 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 don't, I don't know. I mean, like, look, it's obviously, I mean, a great company and a great thing to own. It indexes the entire internet, and, like, I like it, and everyone u- Like, there's all the good things, but it is an interesting question of, like, and I, I totally respect that the founders are like, "Look, we have total control, and our version of control, unlike everyone else's version..." Like, Elon's version of I have total control is max crazy. Stripe's version of I have total control with the Collisons is, like, min crazy, right? And, like, that's completely fine for them. I mean, they're multi-billionaires. They do whatever they want. But it is an interesting thing that they have not paced in storytelling with what they could've been, or where they could've been, where they're, from the place they're at, and how to think about that, right, is, like, the way I'd say. And, like, I actually think there's a really interesting opening them, for them right now with some interesting moves-

— Sam Lessin, More or Less Ep 159

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