Sam Lessin on Startups & Entrepreneurship

Essays

From the Podcast

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

100 billy? Like, that's like, that's a seed AI startup, right? And like, so you're like... Yeah, and like, so they screwed up.

— Sam Lessin, More or Less Ep 159

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

Yeah. Well, I was saying like, I was saying like, look, everyone's joking about how Hollywood's dead, which it obviously is, but I would actually argue in some ways it's like, it's kind of like an Obi-Wan Kenobi situation, which is by striking me down, I'll become more powerful than you can possibly imagine, 'cause now everything is Hollywood, right? And like, what does that mean? I mean, like, one, like companies are valued on what they actually do, profit, revenue, whatever, and then a multiple on top of that, right? But everything is multiple dominated. You can like make your revenue go up, it doesn't matter. What matters is like people's, what multiple they're gonna assign you and like how they think about you. You know, studios, cabals rule everything just like in Hollywood, right? You need to be able to align with Club Elon or Club OpenAI or Club Meta or Club Google to be valuable. Like if Elon says space data center, overnight anything that has space data center in the title is worth a fortune, even if the day earlier it was worth nothing, right? And so like there's a whole cabal studio system developing. And then there's star power that really matters, right? Meaning like there's people who can open movies, there are people who can open startups.

— Sam Lessin, More or Less Ep 158

I did ask i- in our back channel, like i- if the SpaceX IPO makes it harder or easier for other startups to go public. And the, I, I don't know what I was expecting, but uh, several people chimed in harder in the short term because the comps are kind of like not great.

— Sam Lessin, More or Less Ep 154

Well, they have Alpha Camp in summer, but it's effectively just a trial week at their school program. And the program is such, the first two hours of the day, each kid gets a laptop. The laptop evaluates exactly how smart they are at each subject, and then figures out exactly how to get them to, like, an 80% success rate every single day. And, and they play games. So it's like instead of math, they're doing a math game, but they're getting, like, 20% wrong, and they're slowly, like, growing their skills and teaching them in all these different courses and, um, parts of academics. Then the rest of the day, six hours, is, like, workshops and fun stuff, and, like, entrepreneurship, financial literacy. Like, our, our 10-year-old learned how to suture a wound, like s- with stitches. Um, they built apps. They did smart greenhouses. They played with micro:bits. They built, like, catapults.

— Sam Lessin, More or Less Ep 156

The thing I was gonna also say is, in that conversation yesterday with this founder Dave's talking about, what it came down to at the end too, you know, he's trying to recruit his like founding engineer. Everyone's a great e- a lot of people are great engineers. You know, of course some are better than others, fine. But cultural fit I think matters way more now than ever before, when like the, the ability to be a, a great engineer is like much easier than ever before. And so it's like teaching these people how to be human, maybe a little throwback to etiquette school, but also like having street smarts, being a cool person, high integrity, like vibing with the team, I think is, is going to matter more than ever over the next few years for teams.

— Sam Lessin, More or Less Ep 156

It's fine. I- AI can make... If the AI can make the trailer, here's the thing, they should use AI to make it. I- if AI will always make the same fucking trailer over and over again, which means I will instantly get bored of your trailer, right? It's like, it's like, it's like Transformers number 87. Boring, right? I don't care about your trailer. But if you use AI to make an amazing, like to help your improve your storytelling, like, God bless. But basically, I wanna wake up every day as a VC and instead of looking at my inbox, I wanna watch an, a hour of like movie trailers before I get to the meeting I have to go to. And like, I will pick which movies I wanna see/which startups I wanna invest in based on the movie trailer. This is the future.

— Sam Lessin, More or Less Ep 151

No, no, the video mon- I don't give a sh- The money raising thing is stupid. Like, that's not a good story. That's a boring story. But there are great stories. It's like if you can't make... If you, how about this? If you can't make your startup into a sick movie trailer, don't do it, right? It's like you should be able to tell, have a sick movie trailer for your startup. And if you're just like, "I'm making something," and you can't articulate the vision. So, like, Elon companies have sick trailers.

— Sam Lessin, More or Less Ep 151

... I just, I'm just saying that, like, I think, I, I don't know if I can mention it publicly, so I won't, but, like, there's a company that I've known for a while, we put a small C check into 18 months ago. I lo- It's, like, the coolest story, right? And, but the storytelling was never, like, quite there beyond the one-liner, and they sent me their recent video where, like, we've got a video person now, they're doing video, like, every month and helping us with the storytelling, and I'm like, "This is so much better." Like, this is now so compelling, and you're telling it so well because you're fitting it into a narrative format in an era of narrative capitalism. So, like, of all the things that I'm super skeptical of and hate, I actually think this, like, let's give, like, storytel- Like, the future of Hollywood is gonna be, like, storytelling for companies and, like, we should do the sto- we should do the documentaries of startups and, like, continuously be doing high quality video. It's like the anti-TikTok. I'm, like, super it, into it, and I'm, I'm only annoyed, I'm only annoyed that I've, like, been on this 100K documentary thing for a while and, like, really wanted to do this, and I have not done it, and I haven't executed it, right? Like, and so I'm... But, so but it's, it's totally a thing, and I think it is such a thing that, like, one Sam structural mistake is I always, like, see someone else do something and I'm like-

— Sam Lessin, More or Less Ep 151

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