Cheeky Pint is a podcast from Stripe in which Stripe cofounder John Collison interviews founders, builders and leaders over a pint. Its feed shows a median gap of about a week between episodes, though only 3 episodes appeared in the last 90 days as of October 2026, and episodes usually run about 72 minutes.
Cheeky Pint is built around long, relaxed interviews with company builders. The show description frames it as John Collison talking with founders, builders and leaders over a pint, and the episode descriptions describe pub-style conversations about how companies and products got built.
The recent titles show the range: Formula 1 team management (Toto Wolff), underwater drones, Meta's Muse Wonder with Mark Zuckerberg and Alexandr Wang, AR glasses (Evan Spiegel), restaurant economics (Tony Xu of DoorDash), voice AI (Mati Staniszewski of ElevenLabs), compliance (Christina Cacioppo of Vanta) and autonomous cars (Dmitri Dolgov of Waymo). Several episodes run past an hour, and the Zuckerberg and Wang conversation runs about 134 minutes.
One thing to know about the feed: among the 12 most recent episodes we checked, nothing falls between April 27 and October 12, 2026, so the publishing rhythm has been uneven lately.
Our take: founders, operators and anyone who likes long interviews with the people running well-known companies. It suits listeners who want a guest to have room to explain how a business works, rather than a short news recap.
We have no YouTube view data for this show, so these are recent full episodes from its feed that show the range of guests and topics.
If you like Cheeky Pint, these shows in our directory are worth a listen:
More shows to compare are in our best startup podcasts list and the full best podcasts directory.
Show details on this page come from the public listings and feeds below, checked on October 24, 2026.
John Collison, Stripe cofounder, interviews the guests. Individual episode descriptions also mention Chris Sacca, Elad Gil and Matt Huang joining him.
Weekly by median gap (about 7 days between episodes), with 3 episodes in the last 90 days, as of October 2026.
Episodes usually run about 72 minutes, based on the median in the show's feed.
Recent full episodes in the feed include Sundar Pichai on the history and future of AI at Google, Bret Taylor of Sierra on AI agents, and Dmitri Dolgov of Waymo on autonomous cars.
Similar shows in our directory include Acquired, No Priors, Invest Like the Best, How I Built This and 20VC.
