Uploaded March 2026 | Updated September 2026, 1 week ago

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Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode, Bret explains why outcome-based pricing is the future of software business models, and why he believes the atomic unit of AI productivity is a process, not a person. They cover why big companies struggle to adopt AI because they are “shipping their org charts.” Bret also discusses a new type of hyper-generalist, reflects on his experience with the OpenAI and Twitter boards, and explains why he believes we might see the end of the smartphone era.

Full transcript on Substack: open.substack.com/pub/cheekypint/p/bret-taylor-of-sierra-on-ai-agents

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Key moments
00:00:26 Coding
00:16:23 Sierra
00:27:14 Agentic UX
00:38:47 Building support agents
00:45:43 Co-developing with the models
00:50:08 SaaSpocalypse
01:00:50 Stripe Sessions
01:01:33 Outcome-based pricing
01:09:14 Is Sierra short AGI?
01:13:50 AI productivity
01:23:47 How to structure a tech business
01:30:25 Board drama
01:38:24 AI predictions