Cheeky Pint

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?