Cover art for Invest Like the Best with Patrick O'Shaughnessy

Brian Chesky - AI Founder Mode

Invest Like the Best with Patrick O'Shaughnessy

Published
May 5, 2026
Duration
1h 15m
Summary source
description
Last updated
May 6, 2026

Discusses ai, investing.

Summary

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 …

Show notes

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

Themes

  • ai
  • investing