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Cheeky Pint

Stripe
Cheeky Pint
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40 Episoden

  • Cheeky Pint

    Why Sam Altman is against a single superintelligence

    29.10.2026 | 52 Min.
    Sam Altman, CEO of OpenAI, joins John to break down how models uncovered critical PHP vulnerabilities, why test-time compute unlocks massive agent swarms, and OpenAI's internal experiments proving complex math problems like Navier-Stokes. He also shares why sandboxing superhuman models is an unsolved safety dilemma, how robotics will scale future gigawatt data centers, and why businesses must adapt as personal agents replace traditional web forms and mobile apps.

    Timestamps
    (00:00:00) Introduction
    (00:00:12) PHP week
    (00:02:37) Internet early days
    (00:07:33) Cyber Blue
    (00:08:54) Sandboxing
    (00:15:47) Math
    (00:23:12) Agent swarms
    (00:24:48) Stripe Atlas
    (00:25:17) Compute
    (00:37:53) Revenue per gigawatt
    (00:49:27) Token pricing is fake
  • Cheeky Pint

    The airline CEO putting Starlink on every plane

    27.10.2026 | 1 Std. 19 Min.
    Scott Kirby, CEO of United Airlines, joins John and Ben Thompson to break down the airline business and United’s contrarian bets shaping commercial aviation. 
    Scott details United’s massive COVID fleet expansion while competitors shrank, why customer surveys are useless for predicting the future, and rolling out SpaceX’s Starlink across the entire fleet. They also cover in-housing seatback software, why low-cost carriers fail, air traffic control bottlenecks, and Scott’s weekend vibe coding projects.

    Timestamps
    (00:00:00) Introduction
    (00:00:26) Buying planes while the world shrank
    (00:06:35) Owning the airline tech stack
    (00:22:02) Aviation’s biggest bottleneck
    (00:26:21) Stripe Economics
    (00:26:59) Hidden economics of airline networks
    (00:30:19) Starlink
    (00:38:28) What Wall Street gets wrong about aviation
    (00:43:43) It’s the routes 
    (00:55:44) Why Spirit failed but Ryanair works
    (01:15:38) Kirby’s unusual time management hacks

    Scott’s reading list: 
    Unreasonable Hospitality – Will Guidara
    The Impossible Factory – Josh Dean
    Freedom’s Forge – Arthur Herman
    The Sleepless Ape – David R. Samson
    Sea of Tranquility – Emily St. John Mandel
    The End of Eternity – Isaac Asimov
    Tolkien and the Great War – John Garth
  • Cheeky Pint

    How Toto Wolff built the most valuable team in F1

    20.10.2026 | 1 Std. 11 Min.
    Toto Wolff, Team Principal and Co-Owner of the Mercedes-AMG PETRONAS F1 Team, joins John Collison for a pint to discuss the engineering, management, and economics behind modern Formula 1. Toto breaks down how Mercedes spots generational driver talent as early as age eight, why they enforce a strict "No Dickheads" hiring policy across 2,500 employees, and how the F1 cost cap transformed racing teams into $1B+ assets. He also shares his early career as a dot-com investor, the team’s "Navy SEALs" approach to car development, and why he believes live sports are immune to AI disruption.

    Timestamps
    (00:00:22) Spotting driver talent
    (00:06:24) Engineering and team selection
    (00:09:11) The F1 cost cap
    (00:25:21) Toto’s early investing career
    (00:38:15) Running Mercedes as an owner
    (00:46:47) Why F1 team values exploded
    (01:08:24) Succession planning
  • Cheeky Pint

    The company building underwater drones for $50,000

    15.10.2026 | 49 Min.
    Will O'Brien, founder and CEO of Ulysses, joins John and Chris Sacca for a pint to discuss how underwater autonomous robots are scaling up to solve critical ocean challenges.
    They cover the technical history of Guinness (including the math breakthrough that created Student's t-test), why seagrass is an overlooked super-sequester of carbon, and the engineering required to operate robots thousands of meters beneath the surface. Will also breaks down Ulysses' vertical integration strategy, the reality of eco-pragmatism versus "green tape," and what it takes to sell hard tech to defense and offshore energy sectors.

    Timestamps
    (00:00:30) R&D at Guinness
    (00:05:43) Planting seagrass with robots
    (00:16:53) Lowering the cost of doing things in the ocean
    (00:19:00) Landing in a Chinese prison
    (00:20:38) Works in Progress
    (00:27:53) Building robots to withstand saltwater
    (00:31:08) Live use cases for underwater robots
    (00:46:03) The undersea cable vulnerability

    Resources:
    Guinness Quality Standards: https://www.guinnesscelebrate.com/our-quality/quality-standards
    No Great Stagnation in Guinness by Will O’Brien: https://www.thefitzwilliam.com/p/no-great-stagnation-in-guinness
  • Cheeky Pint

    Muse Wonder: Zuckerberg and Wang's $100B AI

    12.10.2026 | 2 Std. 14 Min.
    As Meta scales its AI infrastructure past five gigawatts, Mark Zuckerberg (founder and CEO, Meta) and Alexandr Wang (Chief AI Officer, Meta Superintelligence Labs) join John for a pint to discuss the launch of Muse Wonder and the future of personal AI agents.
    In this episode, Mark and Alex open up about the creation of Meta Superintelligence Labs (MSL), the decision to execute a complete talent reboot, and what it really feels like to make a $100B+ CapEx commitment before knowing if the model will work. They dive deep into the architecture of Muse Wonder—including active memory, multimodal perception, and frontier coding—while laying out their vision for agentic commerce, hardware form factors like smart glasses, and why superintelligence belongs in the hands of billions.

    Timestamps
    (00:00:24) Muse’s breakout use cases
    (00:07:28) Why the model is the product
    (00:14:35) Meet Muse Wonder
    (00:24:56) How frontier models are actually built
    (00:48:26) Betting $100B
    (01:07:21) Agentic commerce
    (01:19:34) OpenRouter 
    (01:20:06) Beyond the smartphone
    (01:27:00) Funding
    (01:34:06) Why AI won’t be winner-take-all
    (01:40:46) Meta Superintelligence Labs (MSL)
    (02:08:11) Working for Mark Zuckerberg
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Über Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

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