Kevin Kelly - Be Generous and Unique

**Patrick O'Shaughnessy** (0:00)
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, Vercell, Plaid and hundreds of other winning companies all have in common? The answer is that they're powered by today's sponsor, WorkOS. If you're building software for enterprises, you probably felt the pain of integrating SSO, skim, RBAC, audit logs and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlock growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack support. Yes, they have real engineers in there who will answer your questions fast. 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. You can find Colossus Review along with all of our podcasts at joincolossus.com.

**SPEAKER_2** (2:01)
Patrick OShaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. 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 PSUMVC.

**Patrick O'Shaughnessy** (2:33)
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 shaped the way I live today. Our conversation explores media, family, money, his concept of the technium, AI, and more. But the central theme of this episode is that we should be as generous and as unique as possible. You will hear us refer to his latest book, Excellent Advice for Living, throughout, and I highly recommend reading it if you haven't already. Please enjoy this great conversation with Kevin Kelly. Kevin, I joke before we hit record here that I've been preparing for this conversation for years, having read, I think, probably all your books and loved your thinking on technology. Maybe we'll talk about technology today as it relates to your new book, but I just have so enjoyed the pithy, simple, beautiful ideas in your latest book. And I wanted to start with one in particular, which maybe you could spend the whole hour on, because it's kind of my favorite idea, which is your goal is to be able to say on your deathbed that you have become fully yourself. I have thought about this idea through the Joseph Campbell lens, through a million lenses, almost on a daily basis for 15 years. And I want to take this idea extremely seriously with you and hear your take on this beautiful idea to open our conversation.

**Kevin Kelly** (3:51)
You're right. There's just a whole lot to unpack in this final piece of advice in this book, My Excellent Advice for Living.
And that does sum up a lot of what I'm trying to do. So the first thing is, I don't think I've met anybody who has achieved this. I've met a lot of people who are absolutely in that direction and are absolutely approaching that. It's like an asymptote curve where you never actually get there. There's always some way to get a little bit closer. But from a distance, you might say, well, you've arrived. And for most of us, this is a very, very high bar. Truly becoming yourself is an incredibly high bar because we are opaque to ourselves. We are just built in a way that we don't have immediate access, even with language, to what it is that we do and how we do it and our own motivations. And it's kind of like we're deliberately kept out of it so we don't mess it up too much. This is a lifelong project for most people. It was coming to understand what it is that's authentic about you, what it is that you do better than other people, what it is that you're about, what your purpose in life is. This is a lifelong project. And the best we can do is to say that we are getting closer.