Invest Like the Best with Patrick O'Shaughnessy
Kevin Kelly - Be Generous and Unique - [Invest Like the Best, CLASSICS]
31 Oct 2025
Full Episode
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are end of one conversations with end of one people. Kevin Kelly is one of the most original thinkers alive and has built a life around curiosity, creativity, and generosity. The central theme of this episode is that we should be as generous and as unique as possible.
We wrote a colossus profile on Kevin and June called Flounder Mode. It describes how he works Hollywood style through a series of creative projects instead of one big thing and reminds us that greatness and joy don't have to be at odds. I hope you enjoy it. Here's a puzzle. What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies all have in common?
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WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience. Go to WorkOS.com to make your app enterprise ready today. 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 Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
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My guest today is Kevin Kelly. Kevin co-founded Wired Magazine and has published a number of seminal books and essays on technology over the past three decades. I have devoured everything Kevin has put out into the world, and many of his ideas shape the way I live today. Our conversation explores media, family, money, his concept of the technium, AI, and more.
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