Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]

Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus along with all of our podcasts at Colossus.com. Chick O'Shaughnessy is the CEO of Passive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of positive some. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

Mm. 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 what he calls AI founder mode and why it will demand even more attention to the details. He walks through his eleven star exercise, which I've used personally many times over the years, which is his way of imagining the most absurd version of a customer experience as a path to product market fit.

We talk about why founders are rarely good early CEOs and what changed him when he stopped chasing adulation and started making things for the love of making them. Please enjoy this great conversation with Brian Chesky. Before we hit go here, we were talking about industrial design, which you studied at RISD. And I have this weird affinity for the history of this topic just because Raymond Lowy, one of the famous industrial designers, helped me a lot in my career indirectly. I'd love to hear you just riff on the influence that guys like him had in your early studies and why you studied that in the first place. Such an interesting background.

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