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SL Sam Lessin Sam Lessin Founding partner at Slow Ventures, a venture firm investing across early- and growth-stage companies, and a columnist at The Information.

“Unlike a human assistant, which is what you're all trying to proxy, everyone is a hairline trigger. If you screw me once, it's so easy to fire a digital assistant… If your human assistant screws up, which they do all the time, you don't instantly fire them… But if you turn into a service and say, we have a service for doing this stuff, the tolerance for mistakes goes to zero.”

More or Less · Startups & Venture · October 2026

“Unlike a human assistant, which is what you're all trying to proxy, everyone is a hairline trigger. If you screw me once, it's so easy to fire a digital assistant… If your human assistant screws up, which they do all the time, you don't instantly fire them… But if you turn into a service and say, we have a service for doing this stuff, the tolerance for mistakes goes to zero.” — Sam Lessin, More or Less

Ten years ago Lessin co-founded Finn, an assistant service with humans in the loop. He is explaining why today's AI agents will hit the same wall: a service is liable for every mistake down the chain, and errors like booking the wrong flight cost more than thin margins can absorb.

Transcript

More or Less Around 18:38 into the episode
Brit Morin

what Finn is for anyone who doesn't know.

Dave Morin

Lick the cookie on Finn, please. I got

Sam Lessin

…don't have the margin to pay for the mistakes. And so there's a fundamental problem with running this service. And then, unlike a human assistant, which is what you're all trying to proxy, everyone is a hairline trigger. Like, if you screw me once, it's so easy to fire a digital assistant effectively. There's no emotional bond. I didn't hire the person. It didn't take me a bunch of time. Like, if your human assistant screws up, which they do all the time, you don't instantly fire them. Like, you're like, I have to work with you. There's some stickiness. There's like this whole human. But people, if you turn into a service and say, we have a service for doing this stuff, the tolerance for mistakes goes to zero. Now, with Finn, people would constantly cancel and then be like, oh man, I really missed that and come back a month later, right? Once there was a mistake. But the…

Brit Morin

But at some level, it does feel inevitable

Jessica Lessin

too. And so the question, I think, is like, what gets us through this period? And Sam, you've written about sort of treaties and you think doing treaties at scale. Like, I do feel like it is inevitable that we're just in an intense early adopter growing pain period. That's how it feels to me. You…

Sam Lessin

I think what's inevitable is the death of the web. I think what's inevitable is like a bunch of like the simple shim like types. Yes, you will obviously use these things, right? And for a bunch of stuff, and they'll be good at a bunch of stuff, but it's the problem is going to be there's going to…

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