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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.

“It's basically businesses understanding correctly that if you get intermediated and become yet another way to clear a transaction at the back end, the market becomes too efficient. You'll have no relationship with the customers and your business is worthless.”

More or Less · Startups & Venture · October 2026

“It's basically businesses understanding correctly that if you get intermediated and become yet another way to clear a transaction at the back end, the market becomes too efficient. You'll have no relationship with the customers and your business is worthless.” — Sam Lessin, More or Less

Lessin's AI agent got stuck in loops trying to book a room on Hilton's site, which now blocks bots. He argued that the stall in agentic commerce isn't technical: businesses are blocking agents because their customer relationship is what they are protecting.

More or Less · 2026-10-09 Listen to the episode → More from Sam Lessin → More Startups & Venture quotes →

Transcript

More or Less Around 27:21 into the episode
Speaker 3

…as a business you're either gonna say well I literally cannot stop people from crawling me or taking my stuff that's what happened with like the textual internet and why we didn't have ai is they basically just like carmen san diego stole the entire internet to bootstrap these things right like

Speaker 1

so what you're saying sam is you're mute Agent tried to book a room for you on the Hilton site, which it used to probably do easily. And now it's getting in these loops because Hilton has done something to like block the agents. Yeah, it's

Speaker 3

Cloudflare. I mean, it's basically businesses understanding correctly that if you get intermediated and to become yet another way to clear a transaction at the back end, the market becomes too efficient. You'll have no relationship with the customers and your business is worthless.

Speaker 1

Which is what Amazon did too, right? To Muse as well.

Speaker 3

Which is correct if you have like enough power to do it. Do

Speaker 1

you think Hilton has enough power to do that?

Speaker names from our own diarization · position estimated from where the line sits in the episode

More from More or Less

“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 “The problem with even OpenAI and Anthropic is if you sue them, it's not clear you'll ever get any money out from them… Whereas Meta is a highly legible, profitable, suable company with everything to lose and therefore can be trusted a lot more. Same with Google.” — Sam Lessin, More or Less