Kevin Kelly - Be Generous and Unique - [Invest Like the Best, CLASSICS]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 31 October 2025

⏱️ 68 minutes

🔗️ Recording | iTunes | RSS

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Summary

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Kevin Kelly⁠ 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 but the central theme of this episode is that we should be as generous and 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. Colossus Profile on Kevin Kelly: Flounder Mode For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠here⁠. ----- This episode is brought to you by⁠ ⁠⁠⁠⁠⁠⁠WorkOS⁠⁠⁠⁠⁠⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit⁠ ⁠⁠⁠⁠⁠⁠WorkOS. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit ⁠joincolossus.com/episodes⁠. Follow us on Twitter: ⁠@patrick_oshag⁠ | ⁠@JoinColossus⁠ Show Notes (00:03:05) ⁠Excellent Advice for Living⁠ - a journey towards authenticity (00:05:05) Uncovering the essence of oneself is a lifelong journey of self-reflection (00:06:47) What he would have done differently at 30 had he internalized this concept earlier (00:08:51) The highest form of self-expression is being authentically unique and redefining success (00:11:05) Conforming to others' definition of success and societal biases hinders progress (00:13:07) Surrender and collaboration are both essential in becoming your authentic self (00:14:38) Prototype your life to embrace imperfections and make ideas tangible (00:17:34) Mastering cultural photography in Asia and developing a keen ability to spot trends (00:19:59) Energy signatures reveal depth, breadth, discovery, and momentum in events (00:22:02) The reward for good work is more work (00:23:42) Money is a tool for doing things, but beware its imprisoning burden (00:28:35) Imagination can be cultivated and improved, often by challenging expectations (00:31:38) Imaginative individuals include lateral thinkers who challenge norms (00:34:41) Rites of passage and rituals provide stability and identity for children (00:38:15) Mealtime without screens, family traditions, and cultivating a family identity (00:41:44) An overview of “The three gates” (00:43:02) Humans are naturally kind (00:47:23) The Technium: an evolving ecosystem of interdependent tech and their tendencies (00:52:01) Thoughts on AI (00:55:55) Overestimating the existential threat of AI (00:57:38) Idiosyncratic expression of creators (00:59:48) Lessons learned about media (01:01:34) Be the only, not the best. (01:05:09) The kindest thing anyone has ever done for Kevin

Transcript

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0:00.0	Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month.
0:05.3	These are end-of-one conversations with end-of-one people.
0:08.3	Kevin Kelly is one of the most original thinkers alive and has built a life around curiosity, creativity, and generosity.
0:15.3	The central theme of this episode is that we should be as generous and as unique as possible.
0:20.6	We wrote a colossus profile on Kevin and June called Flounder Mode.
0:25.0	It describes how he works Hollywood style through a series of creative projects instead of one big thing
0:30.0	and reminds us that greatness and joy don't have to be at odds.
0:33.8	I hope you enjoy it.
0:37.0	Here's a puzzle. What do open AI, cursor,or, Perplexity, Versal, Plaid, and
0:41.4	hundreds of other winning companies all have in common? The answer is that they're powered by
0:45.4	today's sponsor, WorkOS. If you're building software for enterprises, you probably felt the pain
0:50.7	of integrating SSO, Skim, Rback, audit logs, and other features required by big
0:55.8	customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer
1:00.7	platform built specifically for B-to-B SaaS. Whether you're a seed-stage startup trying to land
1:05.6	your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlock growth.
1:13.1	It's essentially striped for enterprise features.
1:15.7	Visit WorkOS.com to get started or just hit up their Slack support.
1:19.7	Yes, they have real engineers in there who will answer your questions fast.
1:23.4	WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience.
1:29.5	Go to workOS.com to make your app enterprise ready today.
1:36.1	Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best.
1:40.1	This show is an open-ended exploration of markets, ideas, stories, and strategies that will help
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