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Bret Taylor: evaluation

10 Mar 2026 Cheeky Pint Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

“I think a large part of why we work with the largest companies in the world is because our technology works.”

— Bret Taylor

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Speaker
Bret Taylor
Attribution
Verified speaker
Claim type
evaluation
Recorded
10 Mar 2026
Publisher
Cheeky Pint

Transcript context

…Pretty close. We did all this work. In fact, we, I think, have the best Cantonese support on the market. Great for us, and it's a huge selling point. It's a technology that will certainly be commoditized in three years. A lot of what we think about is going from essentially technology innovation now. I think a large part of why we work with the largest companies in the world is because our technology works. In three years, those same clients will work with us because we have the best product. If you look at the early marketing for early software-as-a-service companies, they'll explain why having multiple tenants in the same database is safe. That was a huge part of their marketing. Nowadays, if you came and you marketed your product that way, people are like, "What are you talking about? I don't care what database Stripe uses." I think we're just at this period where the technology is so immature. It's a very technology-forward conversation just because people are figuring it out. Just like when Netscape's business was monetized through a web server back 100 years ago. It will evolve from being a technology-forward conversation to a product-forward conversation. The interesting part about building an applied AI company is you can't have the luxury of waiting for all the models to catch up with your aspirations. But you know they will. You have to have the best technology and have to be comfortable with throwing it out. It's a real momentum and pace of innovation game rather than thinking of this as precious intellectual property, if that makes any sense. It absolutely does. But isn't this organizationally hard where, if I'm the head of Cantonese language at Sierra, my incentive, and not disingenuously so, I'll notice all the corner cases where the models aren't that good at Cantonese yet. Obviously, we saw this in prior tech waves, where the cloud adoption laggards were companies that had their own on-prem stuff, and they had a million reasons—half real, half fake—as to why cloud did not suit their business purposes. But how do you avoid getting stuck in this mode of thinking where, "Oh, well, their chain of thought doesn't do what we need," is the classic thing you would hear from someone within the organization.…

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