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Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

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Bret Taylor, co-founder of Sierra and Chairman of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future.

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board Cheeky Pint Mar 10, 2026 11 1 2 Share Bret Taylor, co-founder of Sierra and Chairman 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

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