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Cheeky Pint
Podcast

Cheeky Pint

Stripe

35 episodes

TechnologyBusiness

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

What this show covers

foundersgo-to-marketstartup strategyAI securitycomplianceElevenLabshuman-computer interactionspeech modelsAI translationvoice AIGoogle AIAI infrastructureCapital allocationSundar PichaiTech leadership

What listeners will find here

Why Vanta’s CEO says TAM is overrated—and compliance gets misunderstood
This preview, based only on the published show notes, points to a conversation about compliance, security, AI, and startup strategy with Vanta CEO Christina Cacioppo. Expect discussion of Vanta’s billboard campaign, the tradeoffs between fast AI-driven building and rigorous security, and a blunt take on market sizing.
Can voice AI finally pass for human? ElevenLabs’ co-founder explains the gap
This preview, based only on the published show notes, points to a conversation about why voice AI remains harder than text and where ElevenLabs sees the biggest opportunities. Expect discussion of audio models, translation, voice agents, and the company’s rapid rise.
Sundar Pichai on Google’s AI comeback, bottlenecks, and what comes next
This preview, based only on the published show notes, points to a wide-ranging conversation with Sundar Pichai about Google’s AI trajectory, infrastructure constraints, and capital allocation. It also hints at Google’s internal culture, long-term bets, and why Pichai sees AI as a major economic driver.
How DoorDash won: retention, restaurant economics, and the ‘last two feet’
This preview, based only on the published show notes, points to a wide-ranging conversation with DoorDash CEO Tony Xu. Expect discussion of restaurant economics, fraud, loyalty, delivery models, and why solving autonomy may come down to the final few feet of a delivery.
Can AR glasses really replace the smartphone? Snap’s 2026 bet, explained
This preview, based only on the show notes, centers on Snap CEO Evan Spiegel’s case for Spectacles as the next major computing platform. It also flags side conversations on AI-written code, teen phone use, monetizing the camera, moderation, and Snap’s broader evolution.

Episodes

What comes after smartphones, with Snap CEO Evan Spiegel
What comes after smartphones, with Snap CEO Evan Spiegel
27 Apr 2026 · 1h 2m
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
21 Apr 2026 · 1h 20m
The world of voice AI, with Mati Staniszewski of ElevenLabs
The world of voice AI, with Mati Staniszewski of ElevenLabs
14 Apr 2026 · 1h 0m
The history and future of AI at Google, with Sundar Pichai
The history and future of AI at Google, with Sundar Pichai
7 Apr 2026 · 1h 9m
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
31 Mar 2026 · 57 min
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
24 Mar 2026 · 1h 2m
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
17 Mar 2026 · 1h 16m
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
10 Mar 2026 · 1h 41m
Garrett Langley of Flock Safety on building technology to solve crime
Garrett Langley of Flock Safety on building technology to solve crime
5 Mar 2026 · 1h 44m
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
26 Feb 2026 · 1h 13m
Stripe’s 2025 annual letter
Stripe’s 2025 annual letter
24 Feb 2026 · 27 min
Ramp founder Eric Glyman on the many ways AI is changing corporate spending
Ramp founder Eric Glyman on the many ways AI is changing corporate spending
17 Feb 2026 · 1h 11m
Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
12 Feb 2026 · 1h 30m
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
5 Feb 2026 · 2h 46m
Julia DeWahl of Antares on building nuclear reactors for the US military
Julia DeWahl of Antares on building nuclear reactors for the US military
25 Nov 2025 · 45 min
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
18 Nov 2025 · 1h 18m
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
11 Nov 2025 · 2h 5m
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
4 Nov 2025 · 1h 14m
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
28 Oct 2025 · 1h 16m
Dan Sundheim of D1 Capital on the art of public market investing
Dan Sundheim of D1 Capital on the art of public market investing
22 Oct 2025 · 1h 38m
How to build a $16B car company with RJ Scaringe, founder of Rivian
How to build a $16B car company with RJ Scaringe, founder of Rivian
14 Oct 2025 · 1h 8m
Tobi Lütke is still captivated by internet commerce, 20 years later
Tobi Lütke is still captivated by internet commerce, 20 years later
6 Oct 2025 · 1h 42m
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
1 Oct 2025 · 2h 7m
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
24 Sept 2025 · 1h 18m
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
17 Sept 2025 · 54 min
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
10 Sept 2025 · 1h 14m
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
27 Aug 2025 · 57 min
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
20 Aug 2025 · 1h 16m
Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
13 Aug 2025 · 1h 5m
Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
6 Aug 2025 · 1h 2m
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
9 Jul 2025 · 22 min
The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
25 Jun 2025 · 22 min
OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
18 Jun 2025 · 31 min
Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
18 Jun 2025 · 29 min
Cheeky Pint hosted by Stripe cofounder John Collison
Cheeky Pint hosted by Stripe cofounder John Collison
16 Jun 2025 · 0 min

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