Cheeky Pint

Cheeky Pint is a technology interview podcast produced by Stripe and hosted by Stripe co-founder John Collison; the show describes him as interviewing founders, builders and leaders over a pint. On June 16, 2025, the show released a trailer of about one minute; on June 18 the first two episodes went live together, with OpenAIOpenAIOpenAI is an artificial intelligence research and product organization founded in 2015 that develops the GPT model series, ChatGPT, Codex and a developer API, and conducts research on image, speech, video and intelligent agents. After its 2025 restructuring, the nonprofit OpenAI Foundation continues to control the for-profit OpenAI Group PBC. Its growth has involved large-scale fundraising and compute partnerships, and has also been accompanied by controversies over governance, copyright, privacy and AI safety.Open the full entry co-founder Greg Brockman and Meta chief financial officer Susan Li as guests. The podcast feed lists Stripe as author and copyright holder and places the show under technology and business; transcripts of episodes are published on the show’s Substack page.⁠[1][2]

By October 29, 2026, the show had released 39 numbered episodes. Apart from episode 24, a discussion of Stripe’s 2025 annual letter with no guest, each episode features one or two guests, mostly founders or chief executives of technology companies, along with investors, a technology analyst, a pharmaceutical chief executive and a Formula 1 team principal. Some episodes have a co-host: Charlie SonghurstCharles SonghurstCharles Songhurst (commonly known as Charlie Songhurst) is a technology investor and former general manager of global corporate strategy at Microsoft who has invested in startups since 2013, backing more than 500 startups worldwide; he has been an independent director of Meta since December 2024.Open the full entry (episode 12), Patrick CollisonPatrick CollisonPatrick Collison is an entrepreneur who grew up in Ireland. In 2010 he cofounded the payments and financial infrastructure company Stripe with his brother John Collison and serves as its chief executive; he is also a cofounder of the biomedical research organization Arc Institute and has been a director of Meta since 2025.Open the full entry (episode 18), Dwarkesh Patel (episode 21), Alex RampellAlex RampellAlex Rampell (Alastair Rampell) is an entrepreneur and investor, a general partner at Andreessen Horowitz and leader of its Apps practice. He co-founded TrialPay and Affirm and serves on the boards of Wise and Rocket Companies.Open the full entry (episode 23), Matt HuangMatt HuangMatt Huang is an investor and entrepreneur who is co-founder and managing partner of the technology investment firm Paradigm and founded and leads Tempo, a payments blockchain jointly incubated by Stripe and Paradigm.Open the full entry (episode 28), Elad Gil (episode 31), Chris Sacca (episode 36) and Ben Thompson (episode 38). After episode 34 on April 27, 2026, episode 35 followed on October 12 of that year, with Mark Zuckerberg and Alexandr WangAlexandr WangAlexandr Wang is an artificial intelligence entrepreneur, a co-founder and former chief executive officer of Scale AI. He joined Meta in June 2025 as the company’s first chief AI officer and leads Meta Superintelligence Labs. His work spans AI training data, model evaluation, government applications, and personal agents.Open the full entry as guests.⁠[1]