Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.470]
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Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports, and checking for policy violations. So they built their tools to give that time back, using AI to automate 85% of expense reviews with 99% accuracy. And since Ramp saves companies 5%, it's no wonder that Shopify runs on Ramp, Stripe runs on Ramp, and my business does too. To see what happens when you eliminate the busy work, check out ramp.com/invest. Felix by Rogo is a personal finance a
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.
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 11 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
I was an artist growing up, I didn't know what to do with my life. And I went to the Rhode Island School of Design and at RISD, when you're a freshman, have to pick a major. I'm 17 years old and I'm like, in three months I decide what I'm gonna do the rest of my life. And I remember the department head for industrial design came. I never even heard of the term industrial design. Don't even know what it was. And they said industrial design is designed for everything with a toothbrush to a spaceship and everything in between. I immediately said that's what I wanna do with my life because I was t
Do you think the world's gonna go that way now? You're obviously famous for helping usher in this founder mode idea. That was kind of pre Opus 4.6 or whatever. There's like another layer to that now. I'm curious what we would call it. But it seems like for the first time again, someone even like you running a very large company with lots of people can disintermediate lots of the steps between idea and outcome. Totally. And this design stuff may be even more applicable than ever. What is the new mode like? Because everyone's trying to figure out how do I run a company in this era. So how would
You know, founder mode was something that Paul Graham coined, but based on the experience I had. I think people are basically born good founders, or said differently, it's innate. You don't have learn how to be a good founder. It's like you jump in the pool and you learn how to swim. No one is born a good CEO, and the job of CEO is completely counterintuitive. And almost all of your intuition about what to do is wrong. And so the problem is we founders never were really prepared to be great CEOs. We founders were taught to learn by doing, and that's great for a founder. It's not good as a CEO.
Was there a moment that that like clicked for you that you had to change the mode?
Yes. The pandemic. Two things happened. Actually, speaking of Johnny Ivan, Apple, and another person n
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