
Advertise on podcast: Cheeky Pint
Rating
4.9from
This podcast has
36 episodes
Language
EnglishPublisher
StripeExplicit
No
Date created
2025/06/16
Latest episode
2026/10/12
Average duration
83 min.
Release period
18 days
Description
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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Check latest episodes from Cheeky Pint podcast
Muse Wonder: Zuckerberg and Wang's $100B AI
2026/10/12
As Meta scales its AI infrastructure past five gigawatts, Mark Zuckerberg (founder and CEO, Meta) and Alexandr Wang (Chief AI Officer, Meta Superintelligence Labs) join John for a pint to discuss the launch of Muse Wonder and the future of personal AI agents.
In this episode, Mark and Alex open up about the creation of Meta Superintelligence Labs (MSL), the decision to execute a complete talent reboot, and what it really feels like to make a $100B+ CapEx commitment before knowing if the model will work. They dive deep into the architecture of Muse Wonder—including active memory, multimodal perception, and frontier coding—while laying out their vision for agentic commerce, hardware form factors like smart glasses, and why superintelligence belongs in the hands of billions.
Timestamps
(00:00:24) Muse’s breakout use cases
(00:07:28) Why the model is the product
(00:14:35) Meet Muse Wonder
(00:24:56) How frontier models are actually built
(00:48:26) Betting $100B(01:07:21) Agentic commerce
(01:19:34) OpenRouter (01:20:06) Beyond the smartphone
(01:27:00) Funding(01:34:06) Why AI won’t be winner-take-all
(01:40:46) Meta Superintelligence Labs (MSL)
(02:08:11) Working for Mark Zuckerberg
What comes after smartphones, with Snap CEO Evan Spiegel
2026/04/27
Snap CEO Evan Spiegel joins John at the pub for a deep dive into Snap's "crucible moment" of 2026: the long-awaited consumer launch of Spectacles. Evan explains why he believes the smartphone has become an isolating legacy device and how true AR glasses represent the first step toward making computing human again. They discuss the technical hurdles of fitting a spatial computer into a glasses form factor, why Snap built its own OS from scratch, and how Claude is transforming their software development, with over two-thirds of Snap’s new code now written by AI. Plus, the pair dig into the complex reality of teen phone usage, the distinction between social and media, and why Norway was the first country to embrace Snapchat.
Timestamps
(00:00:15) Snap’s crucible moment
(00:01:05) Specs
(00:09:12) AR as the right form factor
(00:20:45) Stablecoin payouts on Stripe
(00:21:46) Monetizing the camera
(00:28:13) Social media vs messaging
(00:47:37) Content moderation
(00:59:49) Snap’s evolution
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
2026/04/21
Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting fraud in the physical world. They cover the harsh economics of the restaurant industry, why DoorDash succeeded where Google failed, and the harrowing story of spending 40% of their remaining cash on refunds to save the company’s reputation. Tony introduces Dot, their new autonomous delivery robot, and explains why true autonomy requires solving for the “last two feet” of delivery. Finally, he shares lessons from the early days, including why customer obsession sometimes means baking cookies.
Timestamps
(00:00:25) Why did DoorDash win?
(00:10:50) China
(00:17:10) Restaurant trends
(00:27:59) Loyalty
(00:30:40) Stripe Issuing
(00:44:09) Delivery modalities
(00:51:11) Fraud
(00:58:32) New products
(01:13:26) Dot
The world of voice AI, with Mati Staniszewski of ElevenLabs
2026/04/14
Mati Staniszewski is the co-founder of ElevenLabs, the research company making audio accessible across languages and voices. He sits down with John to discuss the "voice Turing Test" and why AI has conquered text but still struggles with conversational speech. They discuss the future of human-computer interaction, including why we still can't get our phones to read a PDF properly and the massive potential for voice agents in everything from farming to healthcare. Mati also opens up about ElevenLabs’ rapid ascent to an $11 billion valuation and gives a behind-the-scenes look at how Ukraine is using their tech for digital government services.
Timestamps
(00:00:27) How audio models work
(00:08:52) ElevenLabs business model
(00:17:50) The conversational Turing Test
(00:21:01) Link by Stripe
(00:26:02) Cascaded vs speech-to-speech
(00:31:53) Universal translation
(00:51:41) Designing an AI-native org
The history and future of AI at Google, with Sundar Pichai
2026/04/07
Sundar Pichai is the CEO of Google and Alphabet. He sits down with John and Elad Gil to discuss Google’s resurgence in the AI race, managing a massive $180 billion CapEx budget, and why 2026 is the year of the supply crunch. They cover the constraints of memory and power, why he believes the US economy will grow significantly due to AI, and the internal cultural shift back to "Googley" optimism. Sundar also shares details on long-term bets like data centers in space, why he wishes he had funded Waymo even faster, and the small thing inside Google that still ignites his passion for building.
Timestamps
(00:00:18) The history of Google and AI
(00:05:17) Speed and Search
(00:12:12) Google’s AI comeback
(00:27:03) Stripe network intelligence
(00:27:53) Bottlenecks
(00:41:25) Capital allocation
(01:00:44) How Google works
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
2026/03/31
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous 101-billboard campaign, and why she believes "market sizing is b******t." They cover the tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers.
Timestamps
(00:00:17) Vanta
(00:12:30) How compliance works
(00:15:06) Breaches
(00:23:52) Stripe Tax
(00:24:43) AI and compliance
(00:44:50) Go-to-market
(00:47:22) Lessons from USV
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
2026/03/24
Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to massive global scaling. He gives a masterclass on the sensor stack (and why you still need Lidar), how they use "Simulation" and "Critic" models to train the AI, and why he believes cars that require human supervision will never naturally evolve into robotaxis. They also cover the new custom-built vehicle that feels like a living room, the economics of ride-hailing in rural Alaska, and the "Russian math nerd" diaspora that seems to run the UK tech scene.
Timestamps
(00:00:22) Russia
(00:02:51) Waymo architecture
(00:09:59) Why now?
(00:19:46) Driving nuance
(00:29:37) Stripe Agentic Commerce Suite
(00:30:17) Hardware
(00:40:20) Emergent behavior
(00:46:36) Scaling
(00:57:56) Google
Article:
EMMA: End-to-End Multimodal Model for Autonomous Driving – Waymo Research: https://waymo.com/research/emma/
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
2026/03/17
Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt Huang to discuss growing their revenue 11x in six months, why they sued their own regulator to list election markets, and how they are building the "New York Stock Exchange of events." They cover why prediction markets are an antidote to social media polarization, the mechanics of market making for culture, and their vision for trading everything from GPU shipments to the Oscars and the weather.
Timestamps
(00:01:39) Suing the government
(00:14:42) Why now?
(00:17:12) Kalshi by numbers
(00:20:58) Solving market making
(00:31:33) Agentic trading
(00:33:43) Sharps
(00:38:45) Stripe Connect
(00:39:33) Evolving Kalshi
(00:44:50) Who loses from Kalshi?
(00:47:35) Insider trading
(00:53:28) The ethics of sports contracts
(00:58:08) New derivatives
(01:04:27) Politics
Article(s):
On the Observational Implications of Knightian Uncertainty – Kevin Hassett & Weifeng Zhong (AEI)The 2028 Global Intelligence Crisis – Citrini Research
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
2026/03/10
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
2026/03/05
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
2026/02/26
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
2026/02/24
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
2026/02/17
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
2026/02/12
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
2026/02/05
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
Podcast reviews
Read Cheeky Pint podcast reviews
edwinarbus 2025/11/29
Host is very smart
He should start a payments company or something; seems very knowledgeable
Anonymous college kid 2025/09/25
Please change this
I love this show, but the transition sound to commercial sounds just like the Doppler effect of a car horn speeding towards you. It gives me a heart a...
Avid pod listener7 2025/09/13
Longer is better
Great show
ZachTXM 2025/06/20
Love it!
I love how they keep the episodes reasonable short instead of like an hour. Guests have been great so far.
Gotta finish your beer though
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