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