Episodes
Two years of tape. Every episode is checked claim by claim and playable.
14 episodes in 2026
🎙CHEEKY PINT
1h 3m What comes after smartphones, with Evan Spiegel of Snap
Snap CEO Evan Spiegel explores the future of post-smartphone computing, detailing Snap's proprietary augmented reality Specs, the transformative impact of generative AI on software creation,…
30 statements 9 featured 4 assessments 1 contradicted
🎙CHEEKY PINT
1h 27m The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Stripe co-founder John Collison interviews DoorDash co-founder and CEO Tony Xu about the operational economics of restaurants, the evolution of on-demand logistics, and the future of autonom…
33 statements 10 featured 12 assessments 3 contradicted
🎙CHEEKY PINT
1h 0m The world of voice AI, with Mati Staniszewski of ElevenLabs
In this in-depth interview, Stripe co-founder John Collison speaks with ElevenLabs co-founder and CEO Mati Staniszewski about the architecture, rapid scaling, and real-world impact of fronti…
33 statements 9 featured 5 assessments
🎙CHEEKY PINT
1h 9m The history and future of AI at Google, with Sundar Pichai
Alphabet CEO Sundar Pichai joins John Collison and Elad Gil to reflect on his decade leading Google, detailing the company's full-stack AI strategy, custom TPU silicon, and the expanding rol…
32 statements 8 featured 5 assessments
🎙CHEEKY PINT
57m Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
In this interview, Stripe co-founder John Collison speaks with Vanta founder and CEO Christina Cacioppo about pioneering the automated trust management category, leveraging AI to streamline …
24 statements 8 featured 3 assessments
🎙CHEEKY PINT
1h 2m The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Waymo co-CEO Dmitri Dolgov details the 20-year technical and operational evolution of autonomous vehicles, explaining Waymo's foundation AI models, custom robotaxi hardware, and the rigorous…
21 statements 5 featured 6 assessments
🎙CHEEKY PINT
1h 16m Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Kalshi co-founders Luana Lopes Lara and Tarek Mansour discuss building a federally regulated prediction exchange, winning a landmark lawsuit against the CFTC, and establishing event contract…
41 statements 12 featured 12 assessments
🎙CHEEKY PINT
1h 41m Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
In this in-depth conversation, Stripe co-founder John Collison sits down with Sierra founder and OpenAI board chairman Bret Taylor to explore the architectural principles, economic transform…
42 statements 10 featured 4 assessments 1 contradicted
🎙CHEEKY PINT
1h 44m Garrett Langley of Flock Safety on building technology to solve crime
Garrett Langley, founder and CEO of Flock Safety, joins Stripe's John Collison to discuss building advanced vehicle recognition, computer vision, and autonomous drone networks that solve cri…
60 statements 14 featured 14 assessments 6 contradicted
🎙CHEEKY PINT
1h 13m Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Former Google TPU architect and MatX co-founder Reiner Pope breaks down the history, architectural trade-offs, and future of specialized AI silicon, highlighting how tailored hardware and so…
26 statements 9 featured 8 assessments 1 contradicted
🎙CHEEKY PINT
27m Stripe’s 2024 annual letter
Stripe’s 2024 annual letter details the platform’s expansion to $1.4 trillion in payment volume, highlighting its strategic investments in artificial intelligence, vertical SaaS, fraud defen…
29 statements 7 featured 13 assessments
🎙CHEEKY PINT
28m Stripe’s 2025 annual letter
In Stripe’s 2025 annual letter, co-founder John Collison reviews the platform’s record $1.9 trillion processing volume while detailing major economic and technological shifts, including the …
31 statements 9 featured 11 assessments 1 contradicted
🎙CHEEKY PINT
1h 11m Ramp founder Eric Glyman on the many ways AI is changing corporate spending
In this discussion, Ramp co-founder Eric Glyman joins Patrick Collison and Alex Rampell to examine how Ramp scaled past one billion dollars in revenue by modernizing corporate spend manageme…
25 statements 10 featured 5 assessments 3 contradicted
🎙CHEEKY PINT
1h 30m Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
Stratechery founder Ben Thompson discusses the strategic and economic dynamics of the AI revolution, analyzing digital advertising architecture, agentic commerce, independent media business …
34 statements 11 featured 2 assessments