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Aug 20, 2025

It wasn’t the message I expected to hear from Bret Taylor, a veteran Silicon Valley executive and, yes—an artificial intelligence startup founder—as I interviewed him on The Information’s TITV to discuss his latest startup, Sierra.

Taylor, more than anyone else I know in the tech industry, has straddled both big and small tech. I first met him when he was working on a startup called FriendFeed, which he sold to Facebook in 2009; he later became the chief technology officer of the social network.

Now, after serving as co-CEO of Salesforce, he’s back in the trenches with Sierra, building software to help companies build AI agents.

Taylor was joined by Winston Weinberg, the founder of another richly valued agent company focused on legal agents, Harvey.

We discussed the current hype around agents and why both of these founders think their best-in-class solutions will eventually beat the incumbents.

We also discussed software versus infrastructure margins, and why Taylor is happy to be in the first group; how the agent-to-agent war will be waged; and why it is OK if AI’s IQ gains plateau.

Read the full article

Sierra’s Bret Taylor and Harvey’s Winston Weinberg: Where the AI Agent War Will Be Won

By Jessica E. Lessin

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