
Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
AI overview.Stripe, co-founder of the payment processing platform Stripe, is known for his significant contributions to the tech industry and entrepreneurship. His experien…
Insights from recent episode analysis
On the show
- Evan Spiegel1 ep
- Tony Xu1 ep
- Mati Staniszewski1 ep
Also: Sundar Pichai, Christina Cacioppo, Dmitri Dolgov, Tarek Mansour, Luana Lopes Lara, Bret Taylor, Garrett Langley, Reiner Pope
Audience Interest
Podcast Focus
Publishing Consistency
Insights are generated by CastFox AI using publicly available data, episode content, and proprietary models.
Most discussed topics
Brands & references
Total monthly reach
Based on 3 signals.
Built from
By chart position
- 🇺🇸United States · TechnologyHOME#1626K to 135K
- 🇬🇧United Kingdom · Technology#49.0K to 48K
- 🇮🇪Ireland · Technology#12.3K to 12K
- 🇨🇦Canada · Technology#121.7K to 9.0K
- 🇮🇳India · Technology#131.7K to 9.0K
- Per-Episode Audience
Est. listeners per new episode within ~30 days
46K to 242K🎙 Sporadic cadence·35 episodes·Last published today - Monthly Reach
Unique listeners across all episodes (30 days)
46K to 242K🇺🇸56%🇬🇧20%🇮🇪5%+8 more - Active Followers
Loyal subscribers who consistently listen
18K to 97K459 real followers tracked across platforms
Market Insights
Platform Distribution
Reach across major podcast platforms, updated hourly
Total Followers
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Total Plays
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Total Reviews
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* Data sourced directly from platform APIs and aggregated hourly across all major podcast directories.
| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 10/27/26 | The airline CEO putting Starlink on every plane | Scott Kirby, CEO of United Airlines, joins John and Ben Thompson to break down the airline business and United’s contrarian bets shaping commercial aviation. Scott details United’s massive COVID fleet expansion while competitors shrank, why customer surveys are useless for predicting the future, and rolling out SpaceX’s Starlink across the entire fleet. They also cover in-housing seatback software, why low-cost carriers fail, air traffic control bottlenecks, and Scott’s weekend vibe coding projects.Timestamps(00:00:00) Introduction(00:00:26) Buying planes while the world shrank(00:06:35) Owning the airline tech stack(00:22:02) Aviation’s biggest bottleneck(00:26:21) Stripe Economics(00:26:59) Hidden economics of airline networks(00:30:19) Starlink(00:38:28) What Wall Street gets wrong about aviation(00:43:43) It’s the routes (00:55:44) Why Spirit failed but Ryanair works(01:15:38) Kirby’s unusual time management hacksScott’s reading list: Unreasonable Hospitality – Will GuidaraThe Impossible Factory – Josh DeanFreedom’s Forge – Arthur HermanThe Sleepless Ape – David R. SamsonSea of Tranquility – Emily St. John MandelThe End of Eternity – Isaac AsimovTolkien and the Great War – John Garth | 1h 19m 35s | ||||||
| 10/20/26 | How Toto Wolff built the most valuable team in F1 | Toto Wolff, Team Principal and Co-Owner of the Mercedes-AMG PETRONAS F1 Team, joins John Collison for a pint to discuss the engineering, management, and economics behind modern Formula 1. Toto breaks down how Mercedes spots generational driver talent as early as age eight, why they enforce a strict "No Dickheads" hiring policy across 2,500 employees, and how the F1 cost cap transformed racing teams into $1B+ assets. He also shares his early career as a dot-com investor, the team’s "Navy SEALs" approach to car development, and why he believes live sports are immune to AI disruption.Timestamps(00:00:22) Spotting driver talent(00:06:24) Engineering and team selection(00:09:11) The F1 cost cap(00:25:21) Toto’s early investing career(00:38:15) Running Mercedes as an owner(00:46:47) Why F1 team values exploded(01:08:24) Succession planning | 1h 11m 26s | ||||||
| 10/15/26 | The company building underwater drones for $50,000 | Will O'Brien, founder and CEO of Ulysses, joins John and Chris Sacca for a pint to discuss how underwater autonomous robots are scaling up to solve critical ocean challenges.They cover the technical history of Guinness (including the math breakthrough that created Student's t-test), why seagrass is an overlooked super-sequester of carbon, and the engineering required to operate robots thousands of meters beneath the surface. Will also breaks down Ulysses' vertical integration strategy, the reality of eco-pragmatism versus "green tape," and what it takes to sell hard tech to defense and offshore energy sectors.Timestamps(00:00:30) R&D at Guinness(00:05:43) Planting seagrass with robots(00:16:53) Lowering the cost of doing things in the ocean(00:19:00) Landing in a Chinese prison(00:20:38) Works in Progress(00:27:53) Building robots to withstand saltwater(00:31:08) Live use cases for underwater robots(00:46:03) The undersea cable vulnerabilityResources:Guinness Quality Standards: https://www.guinnesscelebrate.com/our-quality/quality-standardsNo Great Stagnation in Guinness by Will O’Brien: https://www.thefitzwilliam.com/p/no-great-stagnation-in-guinness | 49m 42s | ||||||
| 10/12/26 | Muse Wonder: Zuckerberg and Wang's $100B AI | 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 | 2h 14m 21s | ||||||
| 4/27/26 | augmented realitysmartphones+4 | Evan Spiegel | SpectaclesSnap+2 | Norway | SnapEvan Spiegel+6 | — | 1h 02m 26s | ||
| 4/21/26 | restaurant industryDoorDash+4 | Tony Xu | DotDoorDash+1 | China | DoorDashrestaurant trends+4 | — | 1h 20m 56s | ||
| 4/14/26 | voice AIhuman-computer interaction+3 | Mati Staniszewski | Link by StripeElevenLabs | Ukraine | voice Turing TestAI+5 | — | 1h 00m 22s | ||
| 4/7/26 | AIGoogle+4 | Sundar Pichai | GoogleAlphabet+1 | — | AIGoogle+5 | — | 1h 09m 23s | ||
| 3/31/26 | compliancetrust+4 | Christina Cacioppo | VantaStripe+1 | — | complianceVanta+5 | — | 57m 27s | ||
| 3/24/26 | autonomous carsAI training+4 | Dmitri Dolgov | WaymoStripe+1 | RussiaAlaska | autonomous vehiclesLidar+5 | — | 1h 02m 20s | ||
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| 3/17/26 | prediction marketsregulation+4 | Tarek MansourLuana Lopes Lara | KalshiCFTC+3 | — | Kalshiprediction markets+6 | — | 1h 16m 30s | ||
| 3/10/26 | AI agentsoutcome-based pricing+4 | Bret Taylor | SierraOpenAI+1 | — | AISierra+5 | — | 1h 41m 23s | ||
| 3/5/26 | public safetycrime prevention+4 | Garrett Langley | Flock SafetyStripe | — | Flock Safetycrime+5 | — | 1h 44m 15s | ||
| 2/26/26 | AI hardwarechip design+4 | Reiner Pope | Large Language ModelsHBM+5 | — | AIchips+7 | — | 1h 13m 07s | ||
| 2/24/26 | Stripe’s 2025 annual letter | 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 | 27m 44s | ||||||
| 2/17/26 | Ramp founder Eric Glyman on the many ways AI is changing corporate spending | 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 | 1h 11m 10s | ||||||
| 2/12/26 | Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media | 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 | 1h 30m 15s | ||||||
| 2/5/26 | Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method | 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.Timestamps00:00:23 Space GPUs00:35:39 Alignment00:58:48 xAI01:15:01 Optimus01:28:03 China01:40:46 Management02:16:38 DOGE02:34:58 Space GPUs redux | 2h 46m 02s | ||||||
| 11/25/25 | Julia DeWahl of Antares on building nuclear reactors for the US military | 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 | 45m 17s | ||||||
| 11/18/25 | Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom | 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 GatesTimestamps(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? | 1h 18m 51s | ||||||
| 11/11/25 | Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma | 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? | 2h 05m 15s | ||||||
| 11/4/25 | Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy) | 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 | 1h 14m 09s | ||||||
| 10/28/25 | Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea | DescriptionCasey 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 ComingKey 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 | 1h 16m 07s | ||||||
| 10/22/25 | Dan Sundheim of D1 Capital on the art of public market investing | 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 | 1h 38m 08s | ||||||
| 10/14/25 | How to build a $16B car company with RJ Scaringe, founder of Rivian | 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 | 1h 08m 48s | ||||||
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Distribution & Reach
About the show, platforms, and key insights.
Distribution & Reach
About the show, platforms, and key insights.
Stripe, co-founder of the payment processing platform Stripe, is known for his significant contributions to the tech industry and entrepreneurship. His experience in building a successful startup lends credibility and insight to his podcasting efforts as he engages with fellow innovators. "Cheeky Pint" features informal yet insightful conversations where John Collison interviews founders, builders, and leaders in the technology and business sectors over a casual drink. This unique format fosters a relaxed atmosphere that encourages candid discussion about the challenges and triumphs of entrepreneurship, making it both relatable and informative. With an audience exceeding 250,001 listeners, the podcast appeals to aspiring entrepreneurs, tech enthusiasts, and business leaders seeking inspiration and practical knowledge. Listeners value the authentic stories and actionable insights shared by guests, enhancing their understanding of the entrepreneurial landscape.
By the numbers
- Total followers: 100K
- Total plays: 21M
- Total reviews: 48
Platforms
Castbox
- Followers: 333
- Plays: 4.6K
YouTube
- Subscribers: 100K
- Views: 21M
- Videos: 398
Podcast App
- Followers: 58
- Reviews: 48
Podcast Republic
- Followers: 68
Audience
professionals, adults
Chart history for Cheeky Pint
Peaked at #1 in Ireland, top 10 in 3 of 45 tracked markets, currently #1 in Ireland.
| Market | Genre | Peak | Current | Trend |
|---|---|---|---|---|
| Ireland | — | #1 | #1 | — |
| United Kingdom | — | #4 | #4 | — |
| CL | — | #5 | #5 | — |
| SG | — | #11 | #11 | — |
| South Africa | — | #11 | #11 | — |
| Canada | — | #12 | #12 | — |
| Australia | — | #12 | #12 | — |
| CH | — | #12 | #12 | — |
| India | — | #13 | #13 | — |
| PT | — | #14 | #14 | — |
| BE | — | #15 | #15 | — |
| United States | — | #16 | #16 | — |
| MY | — | #16 | #16 | — |
| Norway | — | #19 | #19 | — |
| NG | — | #21 | #21 | — |
| KE | — | #24 | #24 | — |
| TR | — | #26 | #26 | — |
| HK | — | #26 | #26 | — |
| GR | — | #28 | #28 | — |
| TH | — | #28 | #28 | — |
Chart Positions
45 placements across 45 markets.
Chart Positions
45 placements across 45 markets.