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

Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits down with John to discuss why most crime is opportunistic, how Flock helps clear over one million crimes a year, and the engineering challenges of building solar-powered cameras and autonomous drones. They cover the shifting landscape of criminal technology, why hardware requires making "one-way door" decisions, and his vision for a future where technology prevents crime before it happens.

Timestamps
(00:00:19) Flock

(00:19:51) Safety vs privacy

(00:23:54) Crime and technology

(00:32:36) Crime rates

(00:43:56) Corporate security

(00:52:16) Stripe Radar

(00:52:54) Competitive landscape

(01:02:41) Drones

(01:09:01) The Flock business

(01:11:39) Building hardware

(01:20:01) Cameras

(01:25:17) PD procurement

(01:32:56) Building your own drones

(01:40:52) What’s next for Flock?

Books:

The Digital Silk Road: https://www.amazon.com/Digital-Silk-Road-Chinas-Future/dp/0063046288

Boyd: https://www.amazon.co.uk/Boyd-Fighter-Pilot-Who-Changed/dp/0316796883 

Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss why the current generation of AI hardware is hitting a wall. They cover the "uncomfortable trade-off" between latency and throughput for current chips, why MatX is betting on combining HBM and SRAM to solve it, and the massive logistical challenge of manufacturing chips at scale with TSMC. Reiner also shares his predictions for AI in 2027, why he prefers Rust for hardware design, and why the best iteration loops happen in your head before writing a line of code.

Timestamps
(00:00:15) Google’s AI revival

(00:07:54) MatX

(00:17:11) AI supply chain

(00:21:48) Designing chips

(00:37:11) TSMC

(00:44:17) Token pricing

(00:44:55) RL-ing chip design

(00:49:26) Design to production

(00:56:05) MatX culture

(01:02:57) Rust

(01:05:21) Cuckoo hashing

(01:09:35) Unexplored model architectures

The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear, and total payment volume on Stripe grew by a third as our customers continued to prosper.

Our annual letter covers the trends that we think are worth paying close attention to as the pace of change accelerates.

Timestamps
(01:48) The sorting machine

(05:45) Global by default

(09:01) Stable progress

(12:14) Working capital’s working. Capital!

(15:09) Escaping from low revenue mode

(18:33) The five levels of agentic commerce

(23:52) A Republic of Permissions 

Eric Glyman is the cofounder and CEO of Ramp, the finance automation platform that now powers over 2% of all corporate spend in the US. He sits down with John and co-host Alex Rampell to discuss how Ramp scaled to over $1 billion in revenue in just seven years, and why the future of fintech is "selling time, not money." They cover the "SaaS apocalypse" (and why lines of code are becoming a liability), how Ramp uses AI agents to review 100,000 expenses a day with 99% accuracy, and why their internal data suggests the US economy is much stronger than the Census Bureau reports.

Timestamps
(00:00:21) Ramp business today

(00:04:27) The *correct* expense policy

(00:11:07) Bill Pay

(00:16:52) AI and software

(00:32:23) Stablecoin-backed cards

(00:33:06) Ramp data

(00:36:25) How to cut your expenses

(00:41:13) Ramp strategy

(00:57:08) Capital One

(01:06:34) Treasury

Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the origins of Stratechery and the "1,000 true fans" model, why Taiwan is the most convenient place to live (and the best Uber Eats market), and why the public markets are wrong to think SaaS is "canceled." Ben also explains why the US failure to control the TikTok algorithm is a disaster, why he’s a "crypto defender" in an age of infinite AI content, and gives John some very direct feedback on Stripe’s ACH implementation.

Timestamps

(00:00:20) Visiting Taiwan

(00:04:59) Aggregation and AI

(00:23:53) TikTok/Bytedance

(00:29:58) Aggregation and AI redux

(00:35:31) Agentic commerce

(00:45:08) Is SaaS canceled?

(00:52:21) Stratechery

(01:03:36) How Ben uses AI

(01:06:06) The TSMC break

(01:13:53) Rapid fire

(01:20:53) Feedback on Stripe

John Collison and Dwarkesh Patel sit down with Elon Musk to discuss why the future of AI isn’t on Earth, but in the "always sunny" vacuum of space. Between pints, they discuss the brutal physics of scaling—from the "farcically cheap" solar cells coming out of China to switching Starship from carbon fiber to stainless steel—as well as the “infinite money glitch” of humanoid robots, China, and DOGE.

Timestamps

00:00:23 Space GPUs

00:35:39 Alignment

00:58:48 xAI

01:15:01 Optimus

01:28:03 China

01:40:46 Management

02:16:38 DOGE

02:34:58 Space GPUs redux

Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down with John to discuss the vision for the "Starlink of electricity", and why AI hyperscalers are driving a nuclear renaissance. They cover the bipartisan shift in nuclear regulation (and why the NRC’s old mandate made "zero" the safest number of reactors), and why true energy resilience requires more than just solar and batteries. Julia also shares lessons from the early days of Opendoor and Starlink, including why customer obsession sometimes means sitting outside a bagel shop.

Timestamps
(00:00) Lessons from SpaceX and Opendoor

(02:46) Introducing Antares

(06:30) The path to market

(12:20) Nuclear vibe shift

(15:11) Regulation

(19:21) Possible energy futures

(24:02) Stripe Radar

(24:55) Nuclear supply chains

(26:43) Antares origin story

(30:24) Funding Antares

(36:09) If Julia was energy tsar

(42:33) Restarting shuttered plants

Satya Nadella, CEO of Microsoft, sits down with John to discuss the diffusion of AI inside the enterprise. He explains why “all your data at your fingertips” is the evergreen pitch, why this AI CapEx cycle is different from the .com bubble, and his vision for "agentic commerce". They also cover Microsoft's product bundling strategy and how he "wanders the virtual corridors" of Teams to run the company.

Links

• [Read] Softwar: An Intimate Portrait of Larry Ellison and Oracle, Matthew Symonds
• [Try] Superwhisper
• [Read] The Internet Tidal Wave, Bill Gates

Timestamps

(00:00) AI adoption in the enterprise
(07:47) How Satya runs Microsoft

(13:45) New UIs

(20:44) Microsoft tackling the early internet

(25:58) Are we in a bubble?

(31:35) Data sovereignty

(38:10) Excel

(42:01) Agentic commerce

(52:45) AI brand loyalty

(59:44) Product bundling

(01:08:18) Microsoft’s culture

(01:12:12) The law of very large companies

(01:16:20) What’s in the water in Hyderabad?

Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company, sits down with John and Patrick to discuss the complex business of drug development. Dave explains the true origin story of GLP-1s (from Gila monster saliva), why their potential goes far beyond weight loss to addiction and inflammation, and how "self-pay" has become the #1 way new patients get Zepbound. They cover the "shadow generic" industry undermining patents, the challenges associated with clinical trial enrollment, and what drove insulin list prices to $275 (while the net price was $40). This is a rare, candid look into the strategies, science, and future of pharma from one of the industry's most influential leaders.

Timestamps

(00:00) Introducing Dave Ricks

(05:07) Making R&D decisions

(10:10) Clinical trials

(24:59) Drug pricing

(32:43) Stimulating more R&D

(54:15) Pros and cons of US healthcare

(58:20) New pharma business models

(01:05:53) Stripe and enterprises

(01:07:00) China

(01:16:31) Generics

(01:22:37) GLP-1s

(1:37:43) r/Peptides

(01:41:25) LillyDirect

(01:46:35) Why do investors love LLY?