PLAY PODCASTS
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Episode 27

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

Cheeky Pint

March 10, 20261h 41m

Audio is streamed directly from the publisher (media.transistor.fm) as published in their RSS feed. Play Podcasts does not host this file. Rights-holders can request removal through the copyright & takedown page.

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