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More or Less · Startups & Venture · October 2026
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.
what Finn is for anyone who doesn't know.
Lick the cookie on Finn, please. I got
…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…
But at some level, it does feel inevitable
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…
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…