Sam Lessin on Artificial Intelligence

Essays

From the Podcast

Blah, blah, blah. It's silly, but the point is that, like, this is just, like, the opposite of it, which if you're Elon, you're gonna price to perfection 'cause you can. You're gonna, like, get the headline number, the trillion number you wanted. You get a bunch of money for the company, I guess, or the, at a high price, and then who cares what the stock trades within reason? It's fine. He got everything he wanted. He bailed out his xAI people. He bailed out his Twitter people. He bailed everyone out, right? So Elon gets to be the guy who makes everyone money. And if you're a SpaceX shareholder, you're like, "Whatever." You kinda got robbed on a few things, but number big.

— Sam Lessin, More or Less Ep 161

This bot school was in, like, a dingy basement, and we taught them how to, like, use AI to, like, crush things. And we actually had them use Claude, not any OpenAI stuff. I think it was the opposite. It was, like, literally we got them, like, shitty bagels, and we, we t- we negged them and taught them how to use GitHub and DigitalOcean.

— Sam Lessin, More or Less Ep 161

Wait, we love Charles. Don't use Charles' name. Leave Charles out of this.

— Sam Lessin, More or Less Ep 161

I think both are almost certainly true in that I am sure that it is true that people lifted a bunch of IP out of Apple on their way to OpenAI. I am also 100% sure that it's the equivalent of, like, continuing to FedEx all your employees all your internal documents when they're no longer employees, and, like, Apple, like, it's so leaky. Right? So, like, both are true. Both are true. It's a great defense. I didn't even ask for this file.

— Sam Lessin, More or Less Ep 161

And it does speak to the fact that it's good to be a seed investor. And again, this is-

— Sam Lessin, More or Less Ep 161

What I will say that the, the basically 10X writedown from max Airtable value to now with all the dilution is brutal, right, is what I would say.

— Sam Lessin, More or Less Ep 161

'Cause their fing- 'Cause they type A on their keyboard, and it autocompletes to airtable.com, and so they will keep using it. Like, why do people... Like, Yahoo is still fucking huge. Huge. Yahoo's huge. Like, why is Yahoo huge? It's-

— Sam Lessin, More or Less Ep 161

It's, like, something ti- This is, like, literally 'cause we're seed investors, we have no information rights on this. Our firm thread yesterday was like, "Hey, Airtable's being..." Or whatever it was. It was like, "Airtable's being sold. I saw it in a tweet. What's it worth? I don't know. This guy tweeted this." What's going on with the I- Like, we don't fucking know. Like, we're like, we're so out of the information flow, but I assume at some point we get some Bending Spoons stock.

— Sam Lessin, More or Less Ep 161

Well, but Dave, I mean, if we wanna be cynical, 'cause we've gotta be cynical a little bit here, here's the other way to look at it. The reason this never happens is because big fancy investors, not us lowly seed investors, but big fancy ones, have no interest in the write down, right? It's a massive write down, right, for them, and they'd rather just stick it on their books and pretend like it's worth something it's not until the last possible moment. The fact that they could get rid of it, get a little bit of cash back, and then turn around and say, "Oh, no, don't worry, we still have our AI upside," that's kinda what allows it to happen. So as much as it's a split landing and it's good for the team, it's also a thing, and big fancy investors who don't want the write down can look at and be like, "All right. Well, we can tell everyone that we took a write down, but not really 'cause of AI." I, I say that having not read the docs, to be clear, but, like that is certainly part of the dynamic.

— Sam Lessin, More or Less Ep 161

But guys, it's also a people thing. It's like Howie wants to work on AI, 'cause AI is cool. You're saddled with a thing that has hundreds of millions of dollars in revenue, but is clearly, like, a SaaS business, and, like, they're like, "Let's fix it. Let's just clarify this. Call a spade a spade." It's painful, but you're not in a place you can IPO it. I don't know, you clear the decks and you let the people... This is so human driven, right? Like, what people wanna work on, what teams wanna work on. Bending Spoons will pick it up and make a lot of money on it, so God bless.

— 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

It is an interesting one, 'cause you think about all the dilution that's gone on between that $90 million valuation and, like, kinda the ultimate Bending Spoons exit, and it's pretty rough math on the core product. Now, the good news is Howie's a great leader and a great thinker, and has an AI play that's coming next. I don't know that much about it, so it's a split thing where it seems like the Airtable, like, legacy business is going to Bending Spoons, which, by the way, I love Bending Spoons. I actually bought stock at IPO in Bending Spoons, I love Bending Spoons so much. So I'm, like, big Bending Spoons fan.

— 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

Let me give some context on this. So I put a $3 million check into Airtable at a 90 post in between rounds early on, 'cause this is now probably in 2012-ish, maybe, uh, that era.

— Sam Lessin, More or Less Ep 161

No, Sundar is fine. Sundar's already doing the job. If you're Demis, you're the forefront of AI, you're with, like, the future is no employees and you're self-improving, nursing a whole-

— Sam Lessin, More or Less Ep 161

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