Cheeky Pint

EntrepreneurshipStartupsVenture CapitalFounder InterviewsSilicon Valley

Stripe cofounder John Collison hosts Cheeky Pint, a lively interview series where he chats with innovative founders, builders, and leaders over a casual pint, exploring the highs and lows of building world-changing companies. Each episode delivers unfiltered insights into tech trends, business strategies, and personal journeys, blending sharp analysis with lighthearted banter. Ideal for entrepreneurs and tech enthusiasts eager to learn from the best in a relaxed, engaging format.

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Featured Episode

The show's latest episode

What comes after smartphones, with Snap CEO Evan Spiegel

4/27/20261:02:26

0:001:02:26

Latest Episodes

What comes after smartphones, with Snap CEO Evan Spiegel

with Snap CEO Evan Spiegel

Apr 27, 20261h 2m

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 computi

The economics and trends of the restaurant industry, with Tony Xu of DoorDash

with Tony Xu of DoorDash

Apr 21, 20261h 20m

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 h

The world of voice AI, with Mati Staniszewski of ElevenLabs

with Mati Staniszewski of ElevenLabs

Apr 14, 20261h 0m

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-comput

The history and future of AI at Google, with Sundar Pichai

with Sundar Pichai

Apr 7, 20261h 9m

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 econ

Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta

with Christina Cacioppo of Vanta

Mar 31, 202657m

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 bullshit." They cover the tensi

The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo

with Dmitri Dolgov of Waymo

Mar 24, 20261h 2m

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