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Cheeky Pint

Cheeky Pint

By: Stripe
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Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.© 2026 Stripe Economics Leadership Management & Leadership
Episodes
  • The world of voice AI, with Mati Staniszewski of ElevenLabs
    Apr 14 2026

    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-computer interaction, including why we still can't get our phones to read a PDF properly and the massive potential for voice agents in everything from farming to healthcare. Mati also opens up about ElevenLabs’ rapid ascent to an $11 billion valuation and gives a behind-the-scenes look at how Ukraine is using their tech for digital government services.


    Timestamps

    (00:00:27) How audio models work

    (00:08:52) ElevenLabs business model

    (00:17:50) The conversational Turing Test

    (00:21:01) Link by Stripe

    (00:26:02) Cascaded vs speech-to-speech

    (00:31:53) Universal translation

    (00:51:41) Designing an AI-native org

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    1 hr
  • The history and future of AI at Google, with Sundar Pichai
    Apr 7 2026

    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 economy will grow significantly due to AI, and the internal cultural shift back to "Googley" optimism. Sundar also shares details on long-term bets like data centers in space, why he wishes he had funded Waymo even faster, and the small thing inside Google that still ignites his passion for building.


    Timestamps

    (00:00:18) The history of Google and AI

    (00:05:17) Speed and Search

    (00:12:12) Google’s AI comeback

    (00:27:03) Stripe network intelligence

    (00:27:53) Bottlenecks

    (00:41:25) Capital allocation

    (01:00:44) How Google works

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    1 hr and 9 mins
  • Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
    Mar 31 2026

    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 tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers.


    Timestamps

    (00:00:17) Vanta

    (00:12:30) How compliance works

    (00:15:06) Breaches

    (00:23:52) Stripe Tax

    (00:24:43) AI and compliance

    (00:44:50) Go-to-market

    (00:47:22) Lessons from USV

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    57 mins
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