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Cheeky Pint
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Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
1 hour 41 minutes Posted Mar 10, 2026 at 12:53 pm.
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.Timestamps
Coding
Sierra
Agentic UX
Building support agents
Co-developing with the models
SaaSpocalypse
Stripe Sessions
Outcome-based pricing
Is Sierra short AGI?
AI productivity
How to structure a tech business
Board drama
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1:41:23
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Show notes
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.Timestamps(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