

Cheeky Pint
Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Episodes
Mentioned books

164 snips
Oct 6, 2025 • 1h 43min
Tobi Lütke is still captivated by internet commerce, 20 years later
Tobi Lütke, the founder and CEO of Shopify, shares his visionary ideas about building technology-driven companies. He explores how internal tools and 'opinionated software' create a unique company culture and drive evolution. Tobi delves into concepts like agentic commerce, emphasizing AI's role in shaping e-commerce futures. He also discusses Shopify's dedication to small businesses, the importance of product craftsmanship, and the impact of internal systems on decision-making. Plus, he offers insights into his personal philosophy on identifying valuable problems.

528 snips
Oct 1, 2025 • 2h 8min
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
Marc Andreessen, a serial entrepreneur and cofounder of Netscape and Andreessen Horowitz, joins John Collison and Charlie Songhurst for a lively conversation. They discuss the challenges of spotting bubbles in technology and explore the evolution of Silicon Valley's ecosystem. Marc shares insights into the 'Elon method' of management and the ongoing impact of AI on productivity and market structures. They also delve into the intricacies of venture capital, the rise of cryptocurrencies, and the future of open-source versus proprietary models.

217 snips
Sep 24, 2025 • 1h 18min
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
Des Traynor, co-founder of Intercom and a thought leader in product strategy, shares insights on transforming Intercom from a messaging tool to an AI-driven customer service platform. He discusses the launch of Fin, their AI agent, and why selling AI is a modern challenge. Des emphasizes the importance of user feedback versus data alone and reveals the four essential traits of successful AI companies. He also dives into co-founder dynamics and the courage required for pivots, making the conversation rich with practical advice for aspiring entrepreneurs.

146 snips
Sep 17, 2025 • 55min
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
Mackenzie Burnett, CEO and co-founder of Ambrook, discusses vital topics in American agriculture. She shines a light on the challenges of labor and immigration in farming, emphasizing the need for rural resilience. Mackenzie also explores innovative financial tools designed to support family-run businesses. She advocates for simple USDA access and the importance of direct-to-consumer strategies for medium-sized farms. Plus, hear her thoughts on the future of fintech in agriculture and intriguing insights about efficiency in accounting.

162 snips
Sep 10, 2025 • 1h 14min
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
Keller Cliffton, Cofounder and CEO of Zipline, shares insights on revolutionizing healthcare logistics through drone delivery. He discusses Zipline’s impressive journey of 115 million miles flown and the monumental impact on maternal mortality in Rwanda. The conversation also dives into the competitive landscape of US and Chinese drone manufacturing, the challenges and innovations in aircraft safety, and the future of multimodal logistics. Cliffton outlines the necessity for efficient delivery solutions, emphasizing simplicity in technology over complexity.

470 snips
Aug 27, 2025 • 58min
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
Scott Wu, Cofounder and CEO of Cognition, dives into the cutting-edge world of AI with a focus on Devin, the first AI software engineer. He shares his journey from math competitions to tech entrepreneurship, discussing the transformative 'Moneyball-ification' of various sectors. The conversation highlights the implications of AI in coding, the landmark acquisition of Windsurf, and Wu's bold assertion that we may already possess AGI. He also examines trust in digital interactions and the evolving landscape of AI mergers.

601 snips
Aug 20, 2025 • 1h 17min
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
Brian Armstrong, the Co-founder and CEO of Coinbase, shares insights on the world of cryptocurrency, tackling everything from battling North Korean hackers to the massive potential of Bitcoin reaching $1 million. He discusses how banks are finally embracing crypto and the role of stablecoins in transforming global payments. Armstrong also emphasizes the importance of electing pro-crypto politicians to foster a supportive environment for innovation. His thoughts on integrating AI in coding present a fascinating view of the future of tech.

195 snips
Aug 13, 2025 • 1h 6min
Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
Vlad Tenev, Co-founder and CEO of Robinhood, discusses his journey from Bulgaria during hyperinflation to leading a revolutionary financial platform. He shares insights on the GameStop saga, emphasizing advice from tech titans like Elon Musk. The conversation also tackles the complexities of payment for order flow and the role of retail investors in capital markets. Tenev makes a compelling case for tokenizing private companies, including Stripe, and outlines a vision for greater financial accessibility in investing.

585 snips
Aug 6, 2025 • 1h 3min
Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
Dario Amodei, CEO of Anthropic and a former AI pioneer at OpenAI, shares insights into his company's remarkable journey to $4 billion in annual recurring revenue. He discusses the capitalistic tendencies of AI models and their potential as standalone profit centers. The conversation touches on the interplay between AI advancements and safety regulations while exploring the historical concept of vitalism and its implications for AI's future. Amodei also reveals strategies for building AGI-focused products and navigating the evolving landscape of AI technology.

346 snips
Jul 9, 2025 • 23min
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
Pieter Levels, a serial entrepreneur and the mind behind Nomad List and Remote OK, shares his journey of building online businesses while living as a digital nomad. He discusses the challenges of monetizing digital content since a young age and contrasts indie hacking with traditional VC funding. Pieter reveals how he leverages automation tools like ChatGPT for efficiency and humorously reflects on the quirks of entrepreneurship in Europe, all while arguing for a more supportive environment for innovation. His insights are both practical and thought-provoking!