Stripe's Cheeky Pint
Read bullet-point summaries of Stripe's Cheeky Pint conversations on payments, AI, SaaS, marketplaces, media, and company building.
Episodes
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What comes after smartphones, with Evan Spiegel of Snap
Snap is entering what CEO Evan Spiegel calls a "crucible moment" in 2026, simultaneously approaching a billion monthly active users, nearing net income
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The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Tony Xu, co-founder and CEO of DoorDash, discusses the company's journey from a Stanford side project in 2013 to America's dominant food delivery platform, and
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The world of voice AI, with Mati Staniszewski of ElevenLabs
Mati Staniszewski is co-founder of ElevenLabs, an AI audio research and product company valued at $11 billion that has become the leading platform for voice
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The history and future of AI at Google, with Sundar Pichai
Sundar Pichai, now a decade into his tenure as CEO of Google (Alphabet), reflects on the company's deep history with AI, its recent resurgence in the AI race
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Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
Christina Cacioppo founded Vanta in 2018 to automate compliance for startups and growing companies, turning what used to be a months-long manual process into a
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The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Dmitri Dolgov, Co-CEO of Waymo, traces the 20-year journey from Google's earliest self-driving research to a service now completing nearly 500,000 fully
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Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Tarek Mansour and Luana Lopes Lara are co-founders of Kalshi, the first federally regulated prediction market in the US, which now trades over $10 billion per
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Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Bret Taylor — co-founder of Sierra, chair of the OpenAI board, and veteran of Google Maps, the Like button, Salesforce, and the Twitter board — discusses the
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Garrett Langley of Flock Safety on building technology to solve crime
Flock Safety is a company that builds technology to help solve crime, starting with license plate-reading cameras and expanding into drones, AI-powered
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Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Reiner Pope is co-founder and CEO of MatX, a startup building specialized chips optimized specifically for running Large Language Models (LLMs). He previously
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Stripe’s 2025 annual letter
Stripe's 2025 annual letter reports a year of accelerating internet economy growth, with businesses on Stripe processing $1.9 trillion in total volume (up 34%
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Ramp founder Eric Glyman on the many ways AI is changing corporate spending
Eric Glyman is the co-founder and CEO of Ramp, a corporate card and finance automation platform founded in 2019 that surpassed $1 billion in annual revenue in
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Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
Ben Thompson, founder of Stratechery and one of the earliest premium newsletter creators, discusses AI's impact on aggregation theory, advertising, SaaS, media
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Elon Musk – "In 36 months, the cheapest place to put AI will be space”
Elon Musk's vision for the next 3–5 years spans orbital data centers, humanoid robots, chip manufacturing at unprecedented scale, and a fundamental rethinking