Cheeky Pint

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

Stripe — Tue, 10 Mar 2026 05:53:27 -0700

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 of Flock Safety on building technology to solve crime

Stripe — Thu, 05 Mar 2026 05:21:07 -0800

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 of MatX on accelerating AI with transformer-optimized chips

Stripe — Thu, 26 Feb 2026 05:09:56 -0800

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

Stripe’s 2025 annual letter

Stripe — Tue, 24 Feb 2026 05:28:39 -0800

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

Ramp founder Eric Glyman on the many ways AI is changing corporate spending

Stripe — Tue, 17 Feb 2026 01:45:00 -0800

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 from Stratechery on AI ads, the end of SaaS, and the future of media

Stripe — Thu, 12 Feb 2026 04:45:00 -0800

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

Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method

Stripe — Thu, 05 Feb 2026 08:50:00 -0800

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 of Antares on building nuclear reactors for the US military

Stripe — Tue, 25 Nov 2025 01:10:59 -0800

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 describes how lessons from Microsoft’s history apply to today’s boom

Stripe — Tue, 18 Nov 2025 01:45:00 -0800

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, CEO of Eli Lilly, on GLP-1s and the business of pharma

Stripe — Tue, 11 Nov 2025 02:15:00 -0800

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?

Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)

Stripe — Tue, 04 Nov 2025 01:45:00 -0800

Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading crypto wallet infrastructure, sit down with John to discuss the future of stablecoins, issuing, and what it will take for crypto to become ubiquitous. Both companies recently joined Stripe, and are uniquely positioned to dissect how crypto is changing financial infrastructure.

Key moments

(00:00) Introducing Bridge + Privy

(06:39) How stablecoins are being used today

(14:27) US Dollar dominance

(25:50) The future of banking

(34:35) Blockchains

(42:27) Building a modular stack

(47:14) Open issuance

(56:55) M&A

(01:11:02) The future of stablecoins

Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea

Stripe — Tue, 28 Oct 2025 01:45:00 -0700

Description

Casey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. He joins the podcast to explain his solar maximalist worldview, why he believes solar costs will drop another 10x, and the core physics that doomed Hyperloop from the start. They also discuss the lessons of the underappreciated industrialist Henry Kaiser, Casey's new venture in solar-powered desalination, his grand plan to refill the Salton Sea, and why he believes "hard-edged" leaders are essential for hardware success.

Show notes

[Read] Ashlee Vance: Elon Musk
[Read] Francis Spufford: Red plenty
[Listen] Beneath the Surface, Episode 2 : Salton Sea
[Read] Marc Reisner: Cadillac Desert
[Read] Albert P. Heiner: Henry J. Kaiser
[Read] Mark S. Foster: Henry Kaiser
[Read] Ernest K. Gann: Fate is the Hunter
[Read] Captain W. E. Johns: Biggles: The Camels are Coming

Key moments

(00:00) Intro

(02:28) Henry Kaiser

(08:49) Introducing Terraform

(13:08) Where electricity won’t work

(16:50) The solar maximalist perspective

(22:57) Terraformer Mark One

(27:49) The role of intervention

(37:30) American dynamism

(47:36) The Origins of Efficiency, by Brian Potter

(48:33) Children and education

(37:30) American dynamism

(55:15) Desalination

(01:08:16) Lessons from leadership

Dan Sundheim of D1 Capital on the art of public market investing

Stripe — Wed, 22 Oct 2025 01:45:00 -0700

Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and the emotional asymmetry of managing billions of dollars. They cover why he thinks successful private companies should avoid the public markets, the real genius of Elon Musk's business approach, and the pattern recognition that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor.

Show notes

[Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham
[Read] The Buffett Partnership Letters (1957-1970)
[Read] Value Investors Club (VIC)

Timestamps

(00:00) The D1 operating model

(07:54) Getting it wrong on NFLX

(11:44) What makes a good stock picker

(18:16) Portfolio-building

(24:35) GameStop

(35:57) The art of short-selling

(41:48) How to spot a turnaround

(47:12) Waking up at 3 AM

(53:14) Money management

(59:31) Dan’s 10-year hands-off stock pick

(01:09:52) China

(01:14:44) Are we in a bubble?

(01:20:41) SpaceX

(01:25:04) Investing in private companies

(01:32:55) Thoughts on the banking industry

(01:35:58) Advice for budding investors

How to build a $16B car company with RJ Scaringe, founder of Rivian

Stripe — Tue, 14 Oct 2025 01:45:00 -0700

RJ Scaringe, founder and CEO of Rivian, sits down for a cheeky pint with John Collison to discuss what it takes to build a car company from scratch, developing the first electric pickup truck, the shift to a software-defined zonal architecture, Rivian's AI-driven approach to autonomy, and the strategy behind their recent $5.8 billion deal with Volkswagen.

Timestamps
(00:00) Gen 1

(12:32) Gen 2

(18:37) Developing the first electric pickup truck

(27:36) John pitches some car features

(36:46) Stripe’s payment methods

(37:54) Autonomous driving

(44:51) Component progress

(53:17) The new economics of cars

(01:01:11) Manufacturing in the US

Tobi Lütke is still captivated by internet commerce, 20 years later

Stripe — Mon, 06 Oct 2025 01:45:00 -0700

Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his perspective on why companies are a form of technology, how internal tools and "opinionated software" shape an organization's culture and accelerate its evolution, and why the best gift is finding a beautiful, unsolvable problem.

Show notes

[Buy] Momax: 140W Universal Travel Adapter
[Read] Benjamin Bloom: The 2 Sigma Problem
[Buy] Ikigai: vitamin cases
[Read] Kevin Kelly: 1,000 True Fans
[Read] Erich Gamma: Design Patterns
[Read] Charles Calomiris: Fragile by Design
[Listen] Business Breakdowns: Formula One
[Watch] Netflix: Formula 1: Drive to Survive
[Read] Mark Robichaux: Cable Cowboy

Key Moments

(00:00) Intro

(07:07) How internal software shapes culture

(16:32) The Shopify vision

(27:49) Peak transaction capacity

(34:36) Agentic commerce

(49:15) Shop Pay

(55:29) Stablecoins

(59:20) Stripe + Shopify

(1:12:23) Learning from the Coinbase board

(1:17:23) Is Tobi ungovernable?

(1:25:02) Entrepreneurship

(1:31:50) Advice for Mark Carney

(1:36:40) Motor racing

Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley

Stripe — Wed, 01 Oct 2025 01:45:00 -0700

Marc Andreessen, cofounder of Netscape and Andreessen Horowitz, sits down for a Cheeky Pint with John Collison and Charlie Songhurst to discuss the history of Silicon Valley, spotting bubbles in real time, the "Elon method" of management, and why the mistakes that haunt you are the companies you don't invest in.

Show notes:

Roger Lowenstein: When Genius Failed: The Rise and Fall of Long-Term Capital Management
David Swensen: Pioneering Portfolio Management
Ian M Banks: Consider Phlebas: A Culture Novel
Walter Isaacson: Elon Musk
Thomas Rid: Rise of the Machines: A Cybernetic History
George McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJ
Steve Blank: The Secret History of Silicon Valley
Tracy Kidder: The Soul of a New Machine
John Perry Barlow: A Declaration of the Independence of Cyberspace
Martin Gurri: Revolt of the Public
John Malone: Born to Be Wired

Full transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst

Subscribe to Cheeky Pint

Spotify: https://open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw

Apple Podcasts: https://podcasts.apple.com/us/podcast/cheeky-pint/id1821055332

Substack: https://cheekypint.substack.com/

Key moments

(00:00) Marc needs to know: what is a cheeky pint?

(04:30) Are we in a bubble?

(14:55) Do VCs matter?

(19:01) The history of Silicon Valley

(32:25) How Digital Research almost made it

(39:02) A bear case on the internet

(59:52) AI productivity

(01:12:10) Stripe + AI

(01:13:08) Crypto

(01:24:08) Should a16z start a hedge fund?

(01:29:51) Big companies

(01:35:33) Boards

(01:40:27) The Elon method

(01:52:59) The future of media

Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

Stripe — Wed, 24 Sep 2025 02:00:00 -0700

Des Traynor, cofounder of Intercom, sits down for a Cheeky Pint with John Collison to discuss the growth of Fin (Intercom’s AI customer service agent), why selling AI products is hard, advice for product marketers, and cofounder dynamics.

Full transcript on Substack: https://cheekypint.substack.com/p/des-traynor-on-reinventing-intercom

Timestamps:

(00:00) Intro

(02:58) Reinventing Intercom

(06:31) Fin

(18:06) 1M resolutions a week

(24:22) Selling AI

(29:34) Product marketing

(37:18) Listening to users

(44:14) Usage-based billing

(45:14) Advice for startups

(52:09) AI pricing

(01:07:27) Cofounder dynamics

(01:11:04) Predictors of company success

(01:15:56) How AI-native is Intercom?

Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak

Stripe — Wed, 17 Sep 2025 07:26:14 -0700

Mackenzie Burnett joins John Collison to talk about American agriculture, labor and immigration challenges, building rural resilience, ERPs, and the principle of money movement. She also shares some feedback for Stripe.

Show notes:

Full transcript on Substack: https://cheekypint.substack.com/p/ambrook-ceo-mackenzie-burnett-on

Timestamps:
(00:00) Introducing Ambrook

(05:37) Serving farmers

(19:25) Building rural resilience

(21:49) The economics of ag

(28:03) If Mackenzie ran the USDA

(30:53) Vertical SaaS

(34:49) The wonders of accounting

(38:41) Ambrook-as-fintech

(44:00) If Mackenzie ran Stripe

(50:53) Joshua Kushner and Dylan Field

Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year

Stripe — Wed, 10 Sep 2025 07:48:34 -0700

Keller Cliffton joins John Collison to talk about Zipline’s journey to 115 million miles flown, the lost art of American airplanes, building 50k drones a year in California, getting to 99.9% reliability, and US vs. Chinese manufacturing.

Books referenced:

Timestamps

(00:00) Intro

(00:45) 115 million miles flown

(04:10) Why drone delivery took so long

(07:38) Getting started in Rwanda

(13:31) 51% reduction in maternal mortality

(15:33) Access vs. waste

(21:45) Scaling globally

(24:05) Zipline’s Platform 1

(25:50) The Right Stuff

(27:22) Drone design and safety

(30:12) Getting to 99.9% reliability

(34:39) Multimodal logistics

(38:15) Zipline’s Platform 2

(44:03) US drone regs and the FAA

(48:02) Progress and stagnation in US aviation

(51:30) If Keller ran the FAA

(54:24) 30% WoW growth in Texas

(58:25) Why Texas and not California?

(01:00:28) Building 50k drones in California

(01:06:18) US vs. Chinese manufacturing

(01:11:30) Advice for hardtech founders

Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything

Stripe — Wed, 27 Aug 2025 08:17:06 -0700

Scott Wu joins John Collison to talk about Cognition’s AI software engineer, the Moneyball-ification of everything, math competitions with Alexandr Wang in 6th grade, acquiring Windsurf over a weekend, whether coding tools will be replaced by the labs, and why he thinks we already have AGI.

Full transcript on Substack: https://open.substack.com/pub/cheekypint/p/cognition-ceo-scott-wu-on-acquiring

Timestamps

(00:00) Intro

(01:13) Early life and maths competitions

(03:47) Addepar job as a high schooler

(05:43) Where are all the young founders?

(08:45) Moneyball-ification of everything

(11:42) Cognition’s AI software engineer, Devin

(15:46) Essential and accidental complexity

(17:59) How Devin works with enterprises

(19:48) IDE productivity

(21:56) Nihilist computer use argument

(25:55) Benchmarking Devin

(27:15) Market structure

(30:32) Agent economy

(37:21) Cognition’s team of founders

(39:31) Jevons paradox and software

(42:00) When will we see AI UIs?

(45:52) “I think we have AGI”

(47:03) Windsurf deal

(52:37) M&A in AI

(54:21) Cognition’s culture

(55:48) Learning as a CEO

(57:12) Scott’s information diet

Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon

Stripe — Wed, 20 Aug 2025 08:13:07 -0700

Brian Armstrong joins John Collison to talk about what’s happening behind the scenes at Coinbase: battling North Korean hackers, war stories from early scaling, confronting people who won’t use AI to code, Coinbase becoming people’s primary financial account, and why banks are now embracing crypto.

Full episode transcript on Substack

https://cheekypint.substack.com/p/coinbase-ceo-brian-armstrong-on-bitcoin

Timestamps

(00:00) Intro

(01:14) How Coinbase won the exchange market

(06:22) Losing money on every bitcoin purchase

(10:54) North Korean hackers

(14:54) The Everything Exchange

(17:39) Crypto will be bigger than gold

(19:22) Stablecoin adoption

(23:28) Jamie Dimon and big banks on crypto

(26:44) Coinbase as your primary financial account

(27:53) Neobanks

(29:41) Bitcoin going to $1 million

(33:16) Crypto in an investment portfolio

(34:43) GENIUS Act

(37:10) Electing a pro-crypto Congress

(45:24) Reforming accredited investor rules

(48:33) Squashing scams

(50:11) Bitcoin preserving the American experiment

(57:09) Balaji Srinivasan

(01:01:05) The mission-first company announcement

(01:05:50) How does Coinbase focus?

(01:07:44) Venture bets and Brian vetoing USDC

(01:12:02) Brian’s AI coding mandate

(01:15:13) Advice for Stripe

Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman

Stripe — Wed, 13 Aug 2025 07:37:36 -0700

Vlad Tenev joins John Collison to discuss Bulgarian hyperinflation, Robinhood Banking, details from the GameStop saga—including advice from Marc Benioff, Mark Zuckerberg, and Elon Musk, payment for order flow economics and Michael Lewis’ Flash Boys, his approach to leadership through the Frank Slootman framework, and how he would change the SEC.

Full episode transcript on Substack: https://cheekypint.substack.com/p/robinhood-ceo-vlad-tenev-makes-his

Timestamps

(00:00) Intro

(00:58) Hyperinflation in Bulgaria

(04:07) Stablecoins

(05:41) Home country bias in investing

(06:59) Robinhood’s origins

(11:23) What the book Flash Boys got wrong

(16:11) Options vs. equities

(17:38) Robinhood Gold

(19:34) Robinhood Banking

(22:04) GameStop advice from Benioff, Zuck, and Elon

(26:40) Impact of retail investors on capital markets

(31:21) Where retail dollars are coming from

(32:10) The gamification narrative

(34:17) Tokenizing private companies

(41:57) Vlad makes his pitch to tokenize Stripe

(45:00) Prediction markets: tennis, the pope, and AI

(49:26) If Vlad ran the SEC

(51:15) How does Robinhood ship so fast?

(52:38) Remote work and Robinhood’s founder community

(55:39) “What would Frank Slootman do?”

(57:32) Active traders

(59:46) Killing Robinhood’s cash card

(01:02:36) Harmonic and mathematical superintelligence

Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism

Stripe — Wed, 06 Aug 2025 06:22:56 -0700

Dario Amodei joins John Collison to talk about Anthropic's growth to ~$5 billion in ARR, how AI models show capitalistic impulses, predictions for an agentic future, the economics of model businesses, and the 19th-century concept of vitalism.

Full episode transcript on Substack: https://cheekypint.substack.com/p/a-cheeky-pint-with-anthropic-ceo

Timestamps

(00:00) Intro

(00:50) Working with your sibling

(01:43) Building Anthropic with 7 cofounders

(02:52) ~$5 billion in ARR and vertical applications of products

(07:18) Developing a platform-first company

(10:08) Working with the DoD

(11:11) Proving skeptics wrong about revenue projections

(13:13) Capitalistic impulses of AI models

(15:43) AI market structure and players

(16:56) AI models as standalone P&Ls

(20:48) The data wall and styles of learning

(22:20) AI talent wars

(26:04) Pitching Anthropic’s API business to investors

(27:49) Cloud providers vs. AI labs

(29:05) AI customization and Claude for enterprise

(33:01) Dwarkesh’s take on limitations

(36:12) 19th-century notion of vitalism

(37:27) AI in medicine, customer service, and taxes

(40:59) How to solve for hallucinations

(42:41) The double-standard for AI mistakes

(44:14) Evolving from researcher to CEO

(46:59) Designing AGI-pilled products

(47:57) AI-native UIs

(50:09) Model progress and building products

(52:22) Open-source models

(54:43) Keeping Anthropic AGI-pilled

(57:11) AI advancements vs. safety regulations

(01:02:04) How Dario uses AI

Serial entrepreneur Pieter Levels on building in public and living as a digital nomad

Stripe — Wed, 09 Jul 2025 06:30:00 -0700

Pieter Levels joins John Collison to discuss building successful online businesses as a digital nomad, thoughts on European accelerationism, and Pieter’s unconventional methods and philosophy as a bootstrapped founder making over $3 million per year.

Full episode transcript

https://cheekypint.transistor.fm/4/transcript

Timestamps

(00:00) Intro

(00:37) Pieter’s resume

(01:33) Trying to make money online as a 12 year old

(02:43) Being one of the first YouTube creators

(03:18) Who should indie hack

(04:31) What Pieter hates about VC-backed businesses

(07:51) Who is digital nomading for?

(09:15) Learning from @patio11

(10:17) 125k tweets and the brand of @levelsio

(10:59) Getting referrals from ChatGPT

(11:43) What Pieter automates with AI

(13:02) Investing and home country bias

(15:05) Hacking thermostats

(15:57) EU acceleration movement

(18:34) Entrepreneurship in the EU

(19:26) Pieter's reflections on Stripe’s API

(21:21) Looking 5 years into the future

The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company

Stripe — Wed, 25 Jun 2025 07:17:52 -0700

The Bot Company founder and CEO Kyle Vogt—who also cofounded Twitch and Cruise—joins John Collison to talk about applying AI to home robots, the similarities between robotics and self-driving, and why the next $100 billion company will have fewer than 100 people.

Full episode transcript

https://cheekypint.transistor.fm/3/transcript

Timestamps

(00:00) Intro

(00:38) The Bot Company pitch

(02:05) Single-task vs. multi-task robots

(04:27) What is the Turing test for robotics?

(05:52) Why this time is different for home robots

(08:42) The last mile in robotics and self-driving

(09:47) Viral demos and hype cycles

(10:38) Commercializing frontier tech

(13:06) Self-driving CapEx

(14:15) Regulatory hurdles

(16:18) Tesla vs. Waymo

(19:21) Why Kyle regrets selling Cruise

(21:39) The next $100 billion company

Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM

Stripe — Wed, 18 Jun 2025 06:00:00 -0700

Susan Li of Meta—the youngest chief financial officer of a Fortune 100 company—joins John Collison to talk about capital allocation, managing investors, and how Mark Zuckerberg has changed over the 17 years of working together.

Full episode transcript

https://cheekypint.transistor.fm/2/transcript

Timestamps

(00:00) Intro

(01:20) Early education and career

(02:15) Lessons from Michael Grimes at Morgan Stanley

(03:12) Leadership traits and succession planning at Meta

(06:05) Mark Zuckerberg’s leadership and culture of feedback

(09:06) Financial forecasting and capital allocation

(14:18) ROI on Meta’s portfolio of bets

(15:05) Investor sentiment in 2022

(17:49) The story behind the “free cash flow” hats

(18:58) CapEx trends in the AI era

(21:48) A memorable earnings call

(24:16) Challenges of allocating compute vs headcount budgets

(26:55) AI’s impact on productivity and operations

OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case

Stripe — Wed, 18 Jun 2025 06:00:00 -0700

Greg Brockman—OpenAI cofounder and Stripe's first engineer—joins John Collison to talk about research-driven product development, an early moment he thought OpenAI was doomed, S curves in AI advancement, and energy bottlenecks.

Full episode transcript:

https://cheekypint.transistor.fm/1/transcript

Timestamps

(00:00) Intro

(02:51) Was OpenAI the first company to take the scaling hypothesis seriously?

(04:53) Lessons from Dota about deep learning

(08:08) What is a good new Turing test?

(08:57) Personalization in AI

(09:57) Research-driven product development

(10:26) An early moment OpenAI felt doomed

(15:01) OS limits on AI product development

(17:59) When will AI make novel advancements in math or science?

(20:03) Energy bottlenecks

(22:30) S curves in AI advancement

(24:00) AI coding

(26:25) Refactoring as a killer AI use case

(27:26) How OpenAI decides what products to built

(28:53) Growing up in North Dakota

(30:17) How far away is AGI?

Cheeky Pint hosted by Stripe cofounder John Collison

Stripe — Mon, 16 Jun 2025 15:57:12 -0700

John sits down with founders and builders over a pint—Greg Brockman (cofounder of OpenAI), Susan Li (chief financial officer at Meta), Kyle Vogt (founder of The Bot Company and cofounder of Twitch and Cruise), and Pieter Levels (indie hacker).

Watch Cheeky Pint on YouTube: https://youtube.com/@stripe.