Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.470]

My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs. He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. We also talk about what changed for him when he stopped chasing adulation and started making things for the love of making them. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes.

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Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.470] is an episode from Invest Like the Best by Colossus.

This episode is 75:23 long.

This episode was published on May 5, 2026.

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