Starcast Join the waitlist
Cheeky Pint

Cheeky Pint

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

Mar 10, 2026 · 1h 41m

Coming soon to iPhone. Already have it? “Listen in Starcast” takes you straight there.

On this episode

About this episode

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…