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

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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Patrick O'Shaughnessy?

  Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of one conversations with N 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.

• 0:38Patrick O'Shaughnessy?

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• 1:19Patrick O'Shaughnessy?

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• 2:02Patrick O'Shaughnessy?

  and you can request a demo at ridgeline.ai.

• 2:09Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, 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.

• 2:34Speaker 01

  Patrick O'Neal 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 Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 3:06Patrick O'Shaughnessy?

  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.

• 3:42Patrick O'Shaughnessy?

  Kevin, I joked 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.

• 4:24Speaker 02

  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 it 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

• 5:05Speaker 02

  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.

• 5:42Patrick O'Shaughnessy?

  When did you awake to the idea yourself? What was the first time that you thought, oh, this is a quest that I could be on for myself. And now I'm curious about who I am and how I might become that fully?

• 5:54Speaker 02

  I think it was actually fairly recently. I don't think you've heard things. You mentioned Joseph Campbell and the others of following your bliss and stuff, and those have been around. But the idea that there was something about realizing the essence of yourself. I think that's not something that I began with or even had an early epiphany on. It's actually more recent is to kind of reflect on things like even writing this book where you have to articulate what it is. So I think I've been doing it, but not articulating it, not aware that I was doing it. And it would have been easier if I had, this goes back to the subtitle of my book, Wisdom I Wish You'd Known Earlier. I wish I'd known this earlier, that that's sort of the framing of a good life is to think

• 6:39Speaker 02

  about what it is that you're trying to optimize in your life, trying to articulate the purpose in your life, and to come to some understanding of what it is that makes you unique and different among all the other eight billion people on the planet at this moment, let alone who've gone before us and who may come after us. And so I think you could be on this journey and not even aware that you're on a journey. And I think a lot of us may do it unconsciously where we're just trying to figure out what we can do well, what we can do that's valuable, what we can do that other people can't do. And we could be doing that every day and not even have this articulation of trying to come to some essence of ourself. But I think it's helpful if we can articulate it that way.

• 7:24Patrick O'Shaughnessy?

  If you had found and taken this idea really seriously, like really internalized it when you were 30, what would you have done differently, do you think? If anything, like how would your behavior have changed?

• 7:35Speaker 02

  It's a great question. I haven't done that exercise, but I may think if I take a minute now to try and do that. This is something I learned at Wired magazine. And then there is a piece of advice in the book that's a little bit like this. It has to do with, there's a value in articulating what you're doing because instead of relying on other people to describe it. And so this is kind of a part of like branding exercise in marketing, which is that you actually want to control the message rather than have people interpret it. And so we learned this at Wired, that we actually had to tell people again and again what it was that we're doing because we couldn't just sort of... Rely on them kind of figuring out from reading the magazines. And so we started to do these little tags on the cover each time saying, we're optimistic. You know, this is an optimistic view. This is what we're doing.

• 8:20Speaker 02

  And so I think if I was thirty, I knew what it is. I would have been spent a little bit more time in accelerating where I was going by actually going back to the Tom Peterson, the brand of you. I was like, what is my brand? That's not kind of a selfish thing. It's actually useful to other people as well. This is what I learned with Wired is that you kind of want to be able to tell people what it is that you're about to help you become better at it. And I think when I was thirty, I had no idea. I didn't even think in those terms. Maybe I would have thought of presumptuous or vain, but in fact, it would have been better all around for everyone if I had really kind of worked on where am I aiming at? Or what do I think I'm about? And that served.

• 9:04Speaker 02

  I'd never really done that very seriously. And I think that would have accelerated the clarity I had of the choices I were going to make beyond that. So that's what I would urge to people is to think about yourself if you have to encapsulate what it is that you're about for other people, to help other people understand it. And therefore to help you realize yourself, what your authentic self is.

• 9:27Patrick O'Shaughnessy?

  I have sort of a wild follow up question. So I'm an investor and my focus is on investing in people that are doing what we call their life's work. And our definition is very simple. It's a lifelong quest to build something for others that expresses who you are. And we were wondering, like, what are the natural limits of this? Steve Jobs clearly is doing his life's work and look at the impact that it's had. What is the highest form of self-expression? And I wondered if it was like Jesus and Buddha, the peoples whose ideas or work has reverberated most through history. And you said you had never seen anyone that actually got to this definition. Do you think maybe the only ones that have are like the world's religious historical figures or something?

• 10:05Speaker 02

  It's possible that of all the candidates, that Jesus was one who the day before he died was most authentically himself. I think you're right. A lot of the people that I've met haven't seen that. I haven't met Gandhi or Buddha or Jesus, but that's possible. That would be a good definition or a good role model. In terms of what are the limits? Your question was, would the ideal candidate person look like that was doing that? And I could be wrong, but for me, I think what we will find is that they will be themselves unlike other people. Not like a Jesus, not like a Buddha, because those, again, those are niches that are occupied by them. And the whole point of being authentic is they're going to be slightly different and weird.

• 10:46Speaker 02

  And the way I say is, you want to invent a new definition of success. That's what your life should be. Your life should be inventing a new definition of success. That success should have its own metrics that are going to be different than then Steve Jobs' metrics. If they aren't different, then they haven't really achieved that thing of being authentically unique. Part of what I would be looking for is looking for people who really had a completely different definition of success. What I tell people is that there are a lot of people whose definition of success are very different than what we normally associate with success. And we don't know about them, and that's part of their definition of success. They may be a huge success and maybe people outside of the family don't even know who they are.

• 11:31Speaker 02

  But they're just incredibly successful in their own lives because fame was not part of that definition. And so this doesn't mean that everybody has to become famous, and quite the contrary.

• 11:42Patrick O'Shaughnessy?

  We think about often the goal here of becoming for yourself as being so obviously true. But the reality that, like you said, almost nobody does it. By definition means that the impediments are enormous. The counterforces are enormous. So what in your experience are those things that most commonly stop people from getting down this path?

• 12:04Speaker 02

  I think that the number one thing is following other people's definition of success. Is being swayed by other people's definition of success. And that's so hard to let go of. It's so hard to surrender the idea that unless you have a million dollars by the time you're 30, whatever it is, that you're not successful. That's a very narrow, well-trodden niche. And it's likely holding you back from your true greatness and your true benefit and your true authentic self and your best self. And because it's probably going to look very different. And so we have these role models like a Steve Jobs. So a lot of people want to be Steve Jobs. Wrong? No. First of all,

• 12:49Speaker 02

  He was a jerk. Having met him a couple of times, he was a jerk. He was a brilliant jerk, a genius jerk. You don't want to be him. And I think just trying to let go of and overcome the cliches, the assumed cultural biases that we have of what it is, that to me, in my opinion, has been what I see as the largest impediment to people achieving this. Because a lot of really authentic success may not look like that to us, to everybody else around you. You don't own a car. You're walking everywhere, whatever it is. And you're saying, I don't think that's successful. And part of it is either educating people about that, other people, so that you have the kind of support that you need,

• 13:34Speaker 02

  or else ignoring it. But it's a very, very difficult thing to let go of and to surrender the assumptions and the prejudices that we have of what that looks like.

• 13:44Patrick O'Shaughnessy?

  Do you think that surrender, it's a powerful word, do you think that surrender is a big part of this, that the key step is accepting the things that you want may not be the things that other people want, and that's hard?

• 13:54Speaker 02

  Yeah. And I have a little bit of wisdom in the book saying, you know, the thing that made you weird as a kid can make you great as an adult if you don't lose it. And the problem is that most of the time, you're losing it. It gets beat out of you. You're weird. Who wants to be weird, right? And so that tendency for us, I think surrendering is one aspect of it. But I would say something else. And this is the paradox. This is the weirdest paradox, a lot of paradoxes. But one of the weird paradoxes is that you cannot truly become yourself by yourself. You can only become unique with the help of everybody else. That is the paradox, right? It's like, it's not like you're gonna become unique on your own. No, it never happens. It takes everybody to make you unique. You can't

• 14:36Speaker 02

  do it by yourself. And that is, again, because we are opaque to our own selves. And we need the friends, family, clients, colleagues, customers to show us what we are becoming, to show us who we are. We can't see it by ourselves. We can't get there by ourselves. We need this help. So that is, again, the paradox. The paradox is the only way you can become somebody unique and different from everybody else is by relying on everybody else to help you do it. And so this is not a matter of, okay, you're just gonna ignore everybody that anything says, and you're on your own. You're not gonna get there.

• 15:14Patrick O'Shaughnessy?

  Why do you suggest that people prototype their life versus drawing up grand plans?

• 15:20Speaker 02

  There's a bunch of reasons, but the primary one is that plans are ideal and to be real, plans are ideal and perfect. And to be real, it means you're imperfect. And you want to take an ideal, a perfect thing and make it as real as fast as possible. And that making it real means that you want to do a prototype. You want to make it real and that will expose all the imperfections. But that's good because reality is going to be imperfect. And so you want to take it from the perfect abstract realm and start to making it real as quickly as you can. And that will inform and improve it because you can't improve abstract perfection. You can't improve abstract things very well. You can only kind of improve things that are real.

• 16:05Speaker 02

  And so that's the one of the reasons, one of the many reasons to prototype. And the second one is that very complicated things, whether artificial things like a robot or an AI or technology and ourselves and our lives, the shortest way to arrive at seeing what they are, that's reliable is actually to run it. There's this like a computational compression that very, very complicated things can only be seen and only be understood by having them run all the way out. You can't like simulate them. If you simulate them, you make a toy model, you abstract them, you're losing too much of it, of what actually happens. And so it's very hard to predict with any kind of accuracy, what will happen.

• 16:49Speaker 02

  Most of the inventors of these great technologies have no idea how they're actually going to be used. And not until people start using them, do we see what their strengths and weaknesses are. And you can think about this all you want, but it's just not going to match what happens when people actually use it. And the same thing with your kind of life, you can have a plan, but the only really way to get there is to go step by step. And so you want to start that as soon as possible.

• 17:12Patrick O'Shaughnessy?

  Is that another cut at this, your advice to sort of, rather than like follow your bliss, quote unquote, just master anything, like when you're young, just like master something? Is that the actionable way of doing what you just said?

• 17:22Speaker 02

  It's very close because follow your bliss for most people, they don't. I don't know what the bliss is and it kind of is paralyzing. But you master something and that platform of mastery of getting something done gives you that positioning, that ladder to stand on to start to move in other directions. But you have to have something to start with. So yes, you're right, that is another form of prototyping where you start anywhere. You master anything. That ability to get things done is the mechanism that you start to creep towards a more authentic place. You can't do it again by thinking about it, which is what people want to do when they're thinking about their follow my bliss is they're trying to figure out and trying to think their way out. And I call that thinkism and thinkism is just this very distracting idea that thinking is the most important thing in the world.

• 18:07Speaker 02

  And it's necessary, but not sufficient to get things done. What in your life do you think you most mastered? Yeah, that's a good question. There are some small things. I am a really, really good ninja travel photographer. And I did 50 years traveling in Asia in this book. And I have a nose, a really great nose for arriving on a place and being able to find something that was happening. I land in a city and I could tell over here, there's going to be something interesting happening. Kind of like the old Polynesian navigators who could see the waves intersecting. I could see waves of people moving in certain directions.

• 18:45Speaker 02

  I could just pick up little posters, less like those GeoGuessr guys that can identify the location of any random photograph that tell you where it is because of all these clues. I have some mastery in being able to photograph cultural things in Asia. That's a pretty obscure mastery, but from that photography, visual storytelling, that could lead to other things. It reminded me of, was it Napoleon movie where his skill was tasting milk? It's like, yeah, okay. It's a very rarefied mastery, but I think more generally I have mastered at Wired and at Whole Earth and with the newsletters. I'm mastering a sense of trends.

• 19:27Speaker 02

  I would say a sensibility of the future, a future sensibility. My mentors like Stuart Brand was very good at this and my partner at Cool Tools, Mark Friendfelder are very good. A kind of saying. Something really important is happening right here. These things are interesting and different, but they're not as important as this thing happening right here. And I think I've done that long enough that I think I also have a mastery in that as well. It doesn't have a real name right now. It's not predictions. It's not forecasting. It's in that general vicinity, but it's much more like a spidey sense. You know, I wrote about e-money in my first book, 1994.

• 20:10Speaker 02

  I had a whole chapter on digital money. I gave that chapter to Stephen Levy and the first issue of Wired, and he went on to write the crypto stuff. And so that was like, oh, this is, I think this is really important. Here's these weird guys who are working on it. And I think that is one of the things I have mastered over these 40 or 50 years is that sense of there's something crucial happening right here.

• 20:36Patrick O'Shaughnessy?

  If you had to describe the energy signature of those things, when you spot them or feel them, how would you encapsulate that in words?

• 20:45Speaker 02

  Yeah, that's a good question. One of the energy signatures is a depth to it. There's a sense in which you encounter it. And then there are these practitioners or people who are plumbing it. They're kind of going there, they're mining it. And when you have conversations or observing them or reading them, you realize, oh, this little mine could go pretty deep in many different directions. There's a depth and a breadth to them saying, there's lots of things that this could intersect with. I would say that's one energy signature is a depth and breadth to the possibility space that it suggests. And secondly, I think there is some detection of how fast things are being uncovered, like

• 21:27Speaker 02

  a rate of discovery in that area. If you encounter some subculture, some little niche, or some new technology, or some research area, there's maybe one person working on it. And every year or so, maybe they discover something, it's like, okay, it's not enough. But if there's a bunch of people and every week they're coming with another something. That says that there's, there's a sufficient momentum. Maybe that's the word I'm looking for. There's a certain momentum or acceleration that's involved. There's a sense of, well, there's enough being discovered that we could kind of imagine this scaling up into something bigger. And so you're looking at the recent past to see what's the rate of new things.

• 22:11Speaker 02

  And then another metric that I use is how much new language and words are needed or what's happening. You want a true area like this will be ahead of language and having to create new terms, new words, new things.

• 22:31Patrick O'Shaughnessy?

  You can't describe it well or easily.

• 22:33Speaker 02

  Right. And so that's another sign that it's worth paying attention to.

• 22:39Patrick O'Shaughnessy?

  I love those ideas. They're beautiful. The other cut at this that I love, maybe my second favorite thing in the book after that opening quote that we explored, is this notion that the reward for good work is more work. When I read that, people are annoyed at me now for not shutting up about this idea. How did that manifest for you? Like, where did you come upon that idea? What does it mean to you? Like, how did it play out in your own life? I absolutely love that idea.

• 23:01Speaker 02

  So it's related to another piece of advice in the book, which is, I actually talked with this with David Allen, the get things done guy, which is that there's a kind of a misappreciation or misunderstanding about productivity, which is that a lot of people who are productivity focused will be trying to minimize the amount of time they spend on working on something. But actually, what you really want to be doing is you want to be finding things that you want to spend as much time as possible working on. That's this idea, like the reward for work is more work, is you want to be doing something where the goal is to spend more time doing it. Yes, productivity is fine, but what you're trying to do is actually move your time

• 23:39Speaker 02

  so that you are trying to spend as much time doing it and trying to find those kinds of tasks and those kinds of assignments and those kinds of jobs where you would almost pay to do it. And so in English, we conflate lots of things in the word work.

• 23:53Patrick O'Shaughnessy?

  Sounds bad.

• 23:56Speaker 02

  Yeah, there's often very negative, but then you have the great masterworks and great work. And so you have both meanings. We're sometimes conflated. Maybe you need some new words about what that other state is where you are working, doing, making, creating, and you want to spend as much time as possible. And the more you do it, the more you can do it.

• 24:19Patrick O'Shaughnessy?

  How do you think about money? I think thoughts so much about work and self-expression and all these things and not following others' definition of success. You already said money is like the number one definition of success, maybe that we've all accepted because it's a common unit. Say everything you can about money, the concept, the thing, how you relate to it.

• 24:37Speaker 02

  In generally, I'm very bored by money. I find it very, very boring. One of my things about crypto, my son and my son-in-law were kind of into crypto for a while. And I would say, look, okay, I'm willing to have a conversation about crypto, but here's one caveat. You can't mention the word money. Can't talk about making money, saving money, whatever it is. Let's talk about crypto without talking about money. Those are very short conversations. Okay. And that's the problem with crypto is that it was only about money, which is only a single dimension. And so I find it just boring in that way. That wasn't true of the internet. We could talk about all kinds of things on the internet. You didn't have to talk about money. And AI is the same kind of thing. So generally, it's a tool. Money is a tool. I like Tim O'Reilly's little definition

• 25:20Speaker 02

  of what money is. It's like gasoline for your car. And the purpose of the gasoline for the cars to drive around, but you're not driving around the gas stations to see how much gas you can get. It's a means to do things. And for me, that's what it is. And I have had the privilege of hanging around billionaires, multi-billionaires. And what I've observed is that in most cases, having money at that level was completely imprisoning and a burden. Basically, it's a burden.

• 25:51Patrick O'Shaughnessy?

  Because it ends up owning them or for some other reason?

• 25:55Speaker 02

  Yeah, yeah, basically. I would say right now, one of my pieces of advice to your listeners is that they should try as hard as they possibly can to never have a billion dollars. I have a couple hundred million, just don't have a billion.

• 26:06Patrick O'Shaughnessy?

  What's the difference between those two?

• 26:08Speaker 02

  Well, a lot of zeros and the more zeros you have, the more weight it is. First of all, it's distorting for your kids and your families. It's this incredible burden for children. And secondly, the weight of it just becomes something you always have to attend to. If you're a responsible person, you're going to take it seriously. And it just becomes something that you can never escape because you can't spend it. It's almost impossible to give away by yourself. So you're suddenly running an organization. It's a whole nother job and it may not be the most authentic thing for you. Right? I mean, a lot of the billionaires I know, if you get them to be honest, it's a lot of luck. It's a good luck or bad luck.

• 26:52Speaker 02

  And so far, far more than you need to do, whatever it is. I like to ask young people, my kids, friends, do the exercise of, okay, I have my magic wand. I'm going to give you a billion dollars, which is what your wish is, right? And so what are you going to do with a billion dollars? Tell me, just make the list. And so they, well, you know, maybe I'll travel around the world or I'm going to buy a boat or something. Okay, or a house or whatever. Okay, you haven't spent any of that money yet. Tomorrow is all going to come back. You give a billion dollars, you cannot spend it. So now what are you going to do with your billion dollars? And it turns out that their dream, whatever it is, can be accomplished for so little compared to a billion dollars. That in most cases, money is simply not the gating factor for what most people want to do.

• 27:34Speaker 02

  There's a great scene in, I think it was Wall Street, where this guy going to Wall Street and his whole goal, just a couple more years, going to make my fortune and then I'm going to quit. So I can buy the motorcycle and ride across China. And all of us travelers just laugh hilariously because you could work at McDonald's for six months, save enough money to buy a motorcycle to ride across China. You don't need to go on to Wall Street to make your billions to do that. And so I find that the focus, you certainly need to have enough to do the things that you want. But for most people's dreams, it's a misplaced hurdle. Imagine they don't have enough money because in fact, what we know about innovation.

• 28:18Speaker 02

  Is that all the real breakthroughs come from the places where there's not enough money, startups. The reason why a startup can succeed is because the big company wants to buy their solutions. They've got money, they're going to buy their solutions, but the solutions can't be bought. They have to be invented. They have too much money to do the hard work of being ingenious and frugal and thrifty and all the other stubborn and persevering that a startup can do. So a startup doesn't have any money, so they're forced to invent the things in a way that if you had money, you'd never get to. And that's why all the breakthroughs happen at the edges and they happen in startups. That lacking of the resources is actually the feature, is actually the benefit. And that's why when young people are starting off, who have very little resources,

• 29:03Speaker 02

  they don't understand they actually have an advantage over the established companies. That lack of resource is an advantage to them.

• 29:12Patrick O'Shaughnessy?

  I'd love to talk about the relationship between creation and imagination. I wonder if in your experience, people are sort of naturally endowed with like a level of imagination, or if it's way more changeable, that I can do things to expand my imagination, because it seems so much like the people that I admire the most are creative and creators. Like they're manifesting something, maybe that's their form of self-expression like we talked about earlier, but that requires tremendous imagination. Where do you think that comes from? Can you cultivate it?

• 29:42Speaker 02

  Yes, I have slowly concluded, maybe this is a changing of the mind, that almost any virtue or quality or talent can be improved. They're certainly unequally distributed and everybody has a higher or lower degree of the natural amount to begin with, but this is the beauty of it. No matter where we start, we can always get better at it. And I think imagination is a skill that can be taught and can be learned and can be improved, even though there are certainly people who have or more naturally inclined in that direction than others. And the same with optimism. I think optimism is something that you can learn and become more optimistic. And it's like a habit and that's true for playing music and everything else.

• 30:23Speaker 02

  And so a lot of the work, almost going back to what I was saying before about imagination is mostly. Forgetting what is the expected answer. I know this from doing lots of workshops with corporations and groups of people from all walks of life, and they were trying to get them to imagine futures. And it was so, so hard to have them let go of what they've seen in Hollywood, or what they've seen in the movie, or what they have been told is possible. And that ability, what Brian Nino and I call the unthinkable, to inhabit those kind of improbable worlds is a skill that has to be learned, has to be regained.

• 31:05Speaker 02

  I mean, I think we have it in childhood, but we are rewarded in other ways for paying attention to reality and understanding what it is that everybody accepts, what the consensus is. That's a variable skill. And that kind of overwhelms our ability to imagine crazy, weird stuff, because we're not usually rewarded for that.

• 31:24Patrick O'Shaughnessy?

  So imagination, cultivating it, is like an exercise in subtraction, not addition. Like, it's not a blank canvas. That's what I would have said. It's like a painter at a blank canvas. No, it's like a sculptor. It's like removing stuff.

• 31:34Speaker 02

  It's mostly about removing stuff these days. I would say that's the first step. You remove it, and then you want to fill it up in a different direction. And by the way, the little side step, I think this is one of the ways that AI will help us. And that is, is because AI is capable of these orthogonal weird directions that is very difficult for humans to let go of, they're much easier. So, working with them to help us inhabit the possibility space in a different way than we find it hard on our own because of our education and biases and inabilities. So that's where I see one of the roles of some of the AIs, is assisting us in our imagination.

• 32:15Patrick O'Shaughnessy?

  I'd love a case study in imagination. When you think of the most imaginative person you've ever encountered, who comes most immediately to mind? What was their story?

• 32:23Speaker 02

  I know some writers, some fiction writers, who naturally can just go off and

• 32:30Speaker 02

  Imagine crazy things and that's partly their ability to fill in details. And then I have other people that I know who are what I would call lateral thinkers. And they have an imagination very much in this direction of overcoming the orthodoxy, overcoming the conventional wisdom. And they'll take something ordinary and just come at it a slightly skewed direction, like laterally on a very, very regular basis. And it's like, oh, I would never thought of that. They are, I believe, have trained themselves to do that. Like Marvin Minsky, who was a very imaginative guy who used to pretend that he was a Martian or a robot. He would just approach everything as if he was from another planet and he would be examining music.

• 33:14Speaker 02

  Okay, well, what is it about music? Why are you people so affected by music? Doesn't make sense to me. And he would kind of investigate things, looking at them from this lateral position just as a habit. So that's a kind of imagination.

• 33:29Patrick O'Shaughnessy?

  I used to love that an intendo idea, I think they had something like lateral thinking with withered technologies or something like new use cases for very old things or something like that.

• 33:38Speaker 02

  Yeah, so there are various forms of imagination. But the point is that the possibility space for ideas is very, very, very, very large. It's probably the largest possibility space that we can imagine. And we tend as humans and living in our lives to kind of retread the same ones. And so anything you can do to get out of those ruts is very powerful, but not always useful. I mean, you can go too far. All we all know from startups and innovation and inventions that you want to be one or two steps away. If you're five or 10 steps away, it doesn't help anybody. There's no way there. If you have some crazy idea, but can't put it into words or pictures or communicate it, then it's lost. If it's an idea so far ahead of its time, it could be right.

• 34:22Speaker 02

  But if you can't get to it in a couple of steps from today, then it's not really useful. So like other things, there's an art to the imagination, to being actually valuable to people is constrained by how many steps away you are that will take someone to get there. So if Only you can arrive at that place, it's not worth anything. You have to get other people there, either to see it and inhabit it with you, like in a story, to actually be able to replicate it in terms of making something, whatever it is. There's an art to this imagination because you can't be too far away, because then it's not useful to anybody. You have to have this adjacent possible that people talk about.

• 35:04Speaker 02

  You want it to be adjacent, but not so distant that, well, it may be true someday, or it may, because I appreciate it 100 years from now. It'd be a lot more useful if you could do something that was more adjacent.

• 35:18Patrick O'Shaughnessy?

  When you study history and you think about the parts of life that have pulled some of these characteristics out of people that we've talked about so far, you come across rites of passage a lot. And it seems like the modern world is as low on different kinds of rites of passage as at any point in history, and that that is very strange and troubling, and hopefully like a historical anomaly when we look back on it 1,000 years from now. Why do you think that's the case? And what would be your prescription for changing it?

• 35:44Speaker 02

  I think traditional cultures are full of rites of passage. I have three kids now, grown young adults. And one thing I know about kids, what I learned was that they crave, when they're young especially, they crave reliability, stability. They rely on having something stable as they invent themselves. They're in the process from the moment they're born to inventing themselves in a very literal sense of developing their personalities. And that is a very uncertain process. It's very scary. They don't know what it means to be a human. They don't know what it means to be a kid. They don't know what's ordinary or extraordinary. They have to accept everything is normal.

• 36:30Speaker 02

  And so the safer they can feel, the more anchored they can be in a family, the easier it is for them to develop their own identity and thrive. And so rituals and rites of passages are things that help. That anchoring and something that they can return to even when things get scary or uncertain or confusing, they can come back into and say, well, at least my family is always there. My family always does this. My family is about this. And these rites of passage and rituals bring them an ability to say, this is what we do. This is something I can rely on. This is a foundation to help me craft my identity, my personality, my contribution.

• 37:14Speaker 02

  And so rites of passage and rituals are something that have been indebted in religion. And when we throw out and get rid of religion, we're often undoing and surrendering and removing those things which need to be replaced in some ways. And so the thing about rituals is that they don't actually have to be about anything. There's the beauty of Burning Man. Burning Man is this ritual and the joke was always we burn it so that we can burn it next year, right? I mean, it's like, it's a ritual that doesn't have any meaning other than in itself, but it's very powerful because it's a ritual. And you burn the man, the same man every time. Okay. And so what we discovered in our family and other families is that if you have rituals, even though they're as simple as having pancakes on Sunday morning,

• 37:59Speaker 02

  or pizza on a Friday night, or birthdays, you always do this, or three times a year, our family always does this thing at the beginning of the seasons. We change the sheets or whatever it is, something that you can count on. And if you do it three times in a row, it becomes a ritual. And that ability of anticipating the thing, of looking forward to it, of relying on it, of having it be there. And that is the foundation of a stable development in their own personality. And so rites of passage is another aspect of that. I think we found that just you have to invent them. You can use religious ones, which are fine, but we don't even have very many of those in America. So we just invented our own, coming into adulthood, writing a passage.

• 38:43Speaker 02

  That we did as a family, we had a bunch of rituals that we would do. And they became, again, another anchoring thing in our kids' understanding of themselves.

• 38:52Patrick O'Shaughnessy?

  If you had other exercises you would recommend families engage in, in addition to like, okay, we need to design rituals, we need to design rites of passage for our kids, let's say, parents for the kids, any other exercises for the family that you would recommend?

• 39:07Speaker 02

  Well, one thing we do, our family, and I highly recommend it, is having meals together with no screens. And the Amish, who I pay attention to, their definition of success, their definition of successful life, the people they most respect are those that are able to have every single meal with their children until the children leave. So they have breakfast, and they have lunch, and they have dinner together as a family. Lunch is the real ringer for most people because their kids are in school and they come back to the house for lunch. So that's something that is very, very profound, is having family dinners. We say grace before meals. We have Thanksgiving rituals, we do gratitude rounds and things.

• 39:51Speaker 02

  There's a lot. There's actually a good book called The Secrets of Happy Families by Bruce Weiler that's really good on this, looking at the research that's been done on understanding the family identity. So one of the things I say is that you want to be able to have your kids be able to say, our family does this or doesn't do this. This idea of a family identity is something else that you cultivate of like saying, our family does this, or our family doesn't do this. This is what our family does. That's fine with them. There's all kinds of things. We didn't have TV if their kids growing up in the house at all. Our family doesn't do TV. You're free to watch TV at your friend's house as much as you want, but we, our family, doesn't do TV. And it's like, okay, that's fine. That's

• 40:35Speaker 02

  good. I understand that. That's part of my identity. And so you can do that.

• 40:38Patrick O'Shaughnessy?

  What about in a marriage specifically? So setting aside the parent-child relationship, obviously that's critical, but just purely at the level of spouses, in the same general vein, exercises, rituals, whatever, anything that you have done or would recommend people think about?

• 40:54Speaker 02

  Yeah, I'm not very good. I think you need to talk to Esther Perel, who's ace in this couples therapy. Actually, there was one thing in the book that I think came from Esther, which is the rule of three in conversation. And that's particularly valuable in a marriage, which is that when someone that you love or intimate with is telling you something in a very intense way, you want to be listening. And then when they're done, wait until they're done, and you say, is there more? And there's usually more. And then they go a wreck. Second round, you listen all the way through. And this is active listening, meaning that you are engaged. You are not just a recording machine. You're probing, you're encouraging. And then you wait until there's a third round of is there more?

• 41:38Speaker 02

  And what's interesting about that is that because it's active listening, is that the other person needs the listener to help them say it. They almost can't say it without that active listening. And so you are able to arrive at understandings and truths and honesty that neither one could get to by themselves. And that ability to take the rule three and say, is there more, is there more, is there more? Is very, very powerful. And oftentimes that explanation and going through that process to the third level is hugely benefit to the person talking, because they needed that person to get it out of them. And often is enough to actualize change.

• 42:21Patrick O'Shaughnessy?

  Speaking of three, my third most powerful takeaway from the book was this notion of the three gates. This idea of asking yourself three questions before you say something. Can you give us that incredibly cool and useful idea?

• 42:34Speaker 02

  I think I said it was a white person who said it. It was actually Rumi, the Afghan poet Rumi, which is that before you say something about someone else particularly, is you want to ask yourself, is it true? Is it

• 42:46Patrick O'Shaughnessy?

  Necessary, I think.

• 42:47Speaker 02

  Kind.

• 42:48Patrick O'Shaughnessy?

  Yeah, true, necessary and kind, right?

• 42:50Speaker 02

  Right. So if it's of those three, then you can say it. And there's a lot in the book about the virtues of kindness, that kindness is not a weakness, but a sign of strength. And you can't really be too kind. If you have a choice between being right or kind, you be kind. And I have another bit of advice for people, which I have had the experience lately, which is to tend as many funerals as you can, particularly when you're young, and listen to what they say about the departed. And the shock to me was that nobody was talking about the achievements, how many patents they had, how many companies they started, how much money they had, none of that. They were talking about what kind of person they were, how they made people feel, whether they were kind.

• 43:35Speaker 02

  It's like, wow, that's really powerful. That's what matters.

• 43:39Patrick O'Shaughnessy?

  You think that humans are naturally kind?

• 43:42Speaker 02

  I do. There's a great book called Humankind that changed my mind, that brought the evidence showing that our received wisdom, the thing we're taught in school, so to speak, that humans are naturally selfish and that when all things being equal, particularly if it gets tough, people will retreat to being completely selfish and self-interested and mean. And I think the evidence is the opposite, and my own experience is opposite, that people generally are kind, you can generally trust strangers, that all things being equal, people want to help each other. And that bias runs through my book, which is that the universe is generally abundant.

• 44:25Speaker 02

  That's the bias of the universe, that there's this other weird paradox at the foundation of the universe, of the human condition anyway, which is that the more you give, the more you get, that the most selfish thing you can do is to be generous. The more you give, the more you get. If that's true for everybody, then where does it come from, right? I mean, it's like, if you give away and you're getting more, and everybody does that, the arithmetic doesn't add up. And that's the paradox. So the paradox is that the most selfish thing you can do is to be generous. And so much flows from that, that by giving away, you're increasing your own happiness. And that's the other little bit of advice. Giving away 10% of what you take in may seem like you've just reduced your purchasing power by 10%.

• 45:10Speaker 02

  But every person who does this will tell you that the happiness and the satisfaction and your life's well being will increase by tenfold, that 10% you don't even notice. So yeah, so I think people are naturally want to be kind, given all things. And what we want to do is to make that as easy as possible.

• 45:30Patrick O'Shaughnessy?

  I have a background in philosophy and so I can't help myself but focus on your advice. That's very big and grandiose and about life and work. But the book is also full of very tiny bits of advice and very tactical bits of advice. Are there any few that stand out to you as like your favorites that make you chuckle or make you happy?

• 45:48Speaker 02

  There are some very, very practical ones that I was very happy to include. Because again, I was writing this for my kids originally, which is that if you lose track of something in your household, in your workshop, in your garage, and you finally find it, don't put it back where you found it, put it back where you first looked for it. I repeat that to myself all the time when I'm putting things back, okay? Put it back where I first looked for it. That's a bit of advice. And another one was I picked up from an editor 30 years ago at Whole Earth. She told me this and it's been true, which is that if you get invited to do something six months from now, ask yourself if you would do it if it was tomorrow morning. And very few events will pass that muster.

• 46:33Speaker 02

  And so I use that to say no, I just imagining, okay, would I get tomorrow morning to fly, whatever it is, or to go into the, or meet whatever it is. And if it isn't a resounding yeah, then it's a no.

• 46:48Patrick O'Shaughnessy?

  I love your rule of seven in research too, that if you just keep pushing for seven levels, you will ultimately hit bedrock. Like it's hard to go deeper than seven levels.

• 46:57Speaker 02

  Part of the trick is you're trying to research something and they don't know. And so you say, well, who might know, or can you tell me who might know? You kind of use the last round to help you develop the next round. Who do you think might know, or where do you think it might go? So you can kind of cascade down to the seven levels. But if you're willing to do that to seven levels, you would generally get a reliable answer.

• 47:21Patrick O'Shaughnessy?

  Did collecting all of this advice change your mind or change you in any material ways?

• 47:27Speaker 02

  Articulating this, again, I don't know about other people, but I find that I actually don't know why I do things. And I don't know exactly how I would describe what I'm doing or whatever. And that this process required me to articulate things and it brought more understanding of what my path is and where I'm going. And so it didn't really change it as much as it illuminated it. And that illumination is valuable. And so I have a better idea about what it is I'm doing than before I started.

• 48:00Patrick O'Shaughnessy?

  I'd love to spend a minute or two, just having the benefit of having you on the call to ask about your conception of technology. Before reading this book, like I said, I'd been preparing this for a long time because I read all your other books about technology. Your notion of the technium has been very influential on me and how I think about how I spend my time and how I invest and everything else. How do you think about the history of technology and the stock of, you call it the technium, the stock of technology that exists in the world? And why that's such a natural extension of human beings?

• 48:32Speaker 02

  In brief, the main insight about the technium, which is my term for the systems of all the technologies in the world. Is the understanding that they don't stand alone. The durable web, that you can't make a hammer without a saw. The saw cuts the handle and the hammer is needed to make the saw. And so they're all code dependent and we use computers to make everything and we need plumbing and the farmers to make the computers. And so there is this web, this ecosystem of technologies all code dependent on each other. And that the bigger this ecosystem gets, the more it adopts the same things that any system of that complexity has, which it has its own internal biases and tendencies.

• 49:14Speaker 02

  All systems, whether it's living systems or even mechanical systems that are complex enough, will exhibit recurring tendencies independent of all the parts. So. This technium that we have, this ecosystem, all the technologies in the world, has certain behaviors that are independent of us humans, the creators, and independent of the parts. And so the question is, what are the general tendencies? What are those wants in the sense of the tendency of a plant is to lean towards the light? Color to want. And so that was my question was, well, with this system, what is it want? What are those tendencies? Part of what I concluded was that the tendencies were basically an extension of the same tendencies

• 49:57Speaker 02

  in evolution of biological systems. And in a certain sense, this technium was the seventh kingdom of life. It's an extension and acceleration of the same forces that made life, that evolved life on the planet and that made self-organized systems of stars and planets and elements. I see the origins of technology back in the Big Bang. It's not human ingenuity. We are just the vehicles. We are just the sexual organs. We're just helping it replicate. When a beaver makes a dam and birds make nests, those are technologies in a certain sense. They're outputs of the mind. And so I see the cosmic arc of the story of technology,

• 50:41Speaker 02

  which begins with the Big Bang and self-organizing systems and elements and stars and planets that have the sufficient, just right amount of gravity and water and other things that this most remarkable molecule of DNA can evolve out of. And then DNA can self-replicate until we have minds. And there are many minds. And out of the minds come other possible forms that can't be done with just water-based tissue. And so I'm imagining that there's technology in other planets throughout the galaxy somewhere and that they're all kind of following this thing of making more and more possibilities.

• 51:23Speaker 02

  And I think that's what the big story in the end about what technology brings to the universe, which is increasing possible ways of being, increasing possible forms, increasing possible ways Of living, each one of those are improbable. So that's the point of it. The most universe is going towards heat death is the probable outcome. Flat, uniform, gray, heat death. Are these strands of the improbable, which are galaxies and stars and elements and planets and minds and technology. And it's all improbable and self maintaining. It keeps making things more and more improbable as long as it keeps going.

• 52:06Speaker 02

  And that's the infinite game that we're involved in is trying to keep the game going, making as many possibilities as possible. And for us humans, for me, to equip every person born with the tools, water and healthcare, and they would need to realize their unique improbable gifts to the world. And the more improbable you are, the more likely you're authentic to what it is that you can do. So in a certain sense, what we're aiming for are improbable lives.

• 52:36Patrick O'Shaughnessy?

  Wonderful idea. Do you think that here to draw the timeline of technology? It seems like we've harnessed information with the printing press. We've sort of harnessed energy with oil and fossil fuels and that maybe we're about to harness intelligence with AI. Is that a clean progression? And is it fair to put AI on the same scale as those other two?

• 52:58Speaker 02

  Yeah, I mean, I think ultimately it'll be even bigger than those other two. Intelligence is not the only thing necessary to get things done. But in fact, evolution itself is a kind of learning. If you abstracted out the topography of things that learn are similar to the things that evolve. Evolution is learning. Our brains are doing similar kinds of mathematically, abstractly, they're very, very related. Learning and evolution are very, very analogous. So a mind is an accelerated version of evolution. It's learning much, much faster than evolution can itself. So we're accelerating evolution with a mind. And so that's very, very powerful when you can accelerate evolution.

• 53:40Speaker 02

  So all the things that we see, all the good things that we've seen evolved on this planet, we're accelerating those processes. Now and making things that are dry and silicon or other materials. And so that's very exciting. That's a huge, huge, powerful force that we're unleashing for the first time on the planet. Okay. And so I think it's way beyond fire and even our own invention of language. In the long term, we're just at the very, very beginning. We haven't really done very much comparatively to what we'll be doing. But it is momentous moment where for the first time we're figuring out what it is. And as humans, this is big because we evolved with other Setian beings.

• 54:23Speaker 02

  There are a lot of other Neanderthals and beyond when we were evolving. But at least for the past 50,000 years, we've been the sole Setian being on the planet.

• 54:32Patrick O'Shaughnessy?

  The hegemon.

• 54:34Speaker 02

  We're now going to go back to having other Setian beings. And we don't know today why we're the only ones. Was it deliberate or was it accidental? We don't know, but we're going to have to share the world with other Setian beings in some ways. And we don't even know what that looks like or feels like. But that's another momentous threshold in our planet. But again, that's very long term. In the short term, we have AI of a very, very narrow sense of pattern recognition and pattern generation. We've synthesized one type of cognition, which is pattern recognition, pattern generation. And all the things we're seeing today, only because we synthesized that one single kind of cognition.

• 55:14Speaker 02

  We haven't been able to synthesize deduction, symbolic reasoning, all the other kinds of things that we do in our own brain. We haven't been able to synthesize yet. So we're still at the very beginnings of this. I think one of the things that it affects us in the long term, say the next century, is that we're going to be undergoing a century-long identity crisis as a species. Going back to the individual of like, what is it you want to be? Why you're here? What do you do that nobody else can do? Now we're going to ask that at the species level. What are humans for? Why are we here? What are we good for? What can we do that others can't? And then we have genetic engineering where we can actually change our own bodies. And so what is that we want to become?

• 55:59Speaker 02

  And one of the things that AIs are going to force us to answer is because we make these AIs, we train them on humans and humans are on average sexist and ageist and racist and mean. And so the AIs are like average humans, but we say, no, no, no, no, you have to be better than us. So what does it look like? What does a better human look like? We don't have a good model for that. We don't have a consensus on that. And yet we're going to demand that our AIs be better than us. So that's going to force us in some ways to become better humans ourselves.

• 56:32Patrick O'Shaughnessy?

  Is there anything else that you think is over or underestimated about what's happening in this technological change?

• 56:38Speaker 02

  Yeah, I mean, the idea of existential threat is completely overrated. It's a fantasy. I'll tell you what's overrated. Intelligence itself is overrated. It's overrated by guys who like to think, who think that thinking is the most important thing in the universe. To get things done is not necessarily the most important. But take Einstein and a tiger and put them in a cage. Who wins? It's not the smartest guy. Why is that? Because it takes other things besides intelligence to get things done in the world. It's not the company with the smartest people that will dominate. It's not the smartest person in the room that necessarily knows what to do. Intelligence is necessary, but not sufficient to get things done in the world.

• 57:15Speaker 02

  And the people who imagine the smart genius AI thing are what I guilty of thinkism in the sense that they think that thinking trumps everything else and it doesn't. There are so many other things that you need to accomplish something to have an effect on actually making things happen, including empathy, including perseverance, all kinds of things. And so a lot of the fears of the existential threat of the AIs taking over and killing us all are based on the idea that if you have AI genius level thing, that it will overwhelm anything else in the world. But what we know is that the will to survive will always overwhelm the will to predate.

• 57:57Speaker 02

  I mean, this is why only one out of 10 predations work because the will to survive is much more powerful than the will to kill. And so it'd be really tough. Intelligence alone is not enough. So anyway, so that's overrated. I think general intelligence is overrated.

• 58:14Patrick O'Shaughnessy?

  One of the things that I remember distinctly from my teenage years was my two favorite magazines were probably Maxim and Wired, my two burgeoning interests as a teenager. And you also created so many interesting other forms of content, whether that's photography, whether that's books. What do you think explains the best, I guess I'll just call it content, media? What do you think unites the very best things that you've created? And that you've appreciated that others have created?

• 58:43Speaker 02

  One of the things I learned about magazines was that the best magazines at their best times, because magazines can outlive individuals, like the New Yorker saying, is that they work best when they're an expression of the personality of the editor. The more idiosyncratic creations are, to me, that's one of the commonalities. If you unleash the creators to really give them that room to create, unencumbered and constrained by the lawyers, by the bureaucracy, by committees, by the thought police, whatever it is, the more that that can actually be an expression of idiosyncratic creativity, to me, the stronger that is. We have that with novels, because it's a sole person.

• 59:28Speaker 02

  Usually, if they have any kind of clout, they can demand certain things. It's much harder to do with other media like a movie, because there's just so many people involved. And that's one of the reasons why I think AI is going to be hugely transformative, because we'll be able to have a 90 minute movie made by a single person, auto generating all these other characters and stuff at their command, at their direction, the director. That'll be true for games, it's true now in newsletters. The newsletters I follow are by people with very strong personalities. And we own books that you like. There's somebody with a very strong point of view. That we don't see that as much of the screen that's now the center of our lives. And I think we miss that.

• 1:00:12Speaker 02

  And I think AI will help us regain that by actually enabling individuals or very, very small partner teams to create works in this medium of the screen.

• 1:00:25Patrick O'Shaughnessy?

  When you were running Wired, and Wired obviously was like the expression of your taste and personality, what practices, what did you do to protect that? That seems incredibly desirable in any publication, that it's like the taste of the person magnified or something.

• 1:00:40Speaker 02

  Yeah, we projected by owning more than 50% of which we lost. It was a very terrible, terrible story. We lost control and that's why we had to sell. And that's when we all left. Okay, we left, not because it wasn't funny anymore, but because we lost control over it. We weren't having to report to anybody. We were just trying to make the magazine that we wanted to read and it was totally fun because we could say anything. That was one of the ways I would say is you have to retain control, ownership of it. And this goes back to, well, I was talking about articulating. For me, there was something that we were very slow to see at Wired, but I did learn that. There's a bit of advice in my book about what we learned from the advertising people, which is to get your message across,

• 1:01:25Speaker 02

  you have to simplify, simplify, simplify, and then exaggerate. There was a sense of like us coming to understand what it was that we're doing in our role and being able to, again, articulate that to the people. So this idea of the optimistic view was not something that was so evident at the very beginning, but it became evident that that was our role, that that was what we were doing in part, that that was sort of what we were about. And that helped tremendously in terms of deciding whether this is a Wired story or not. There's tons and tons of directions to go. And so being able to brand it in that sense

• 1:02:04Speaker 02

  was us being partly enabled by us articulating it ourselves and being able to do that.

• 1:02:11Patrick O'Shaughnessy?

  Do you think then, like, it's so interesting thinking across our conversation, how maybe the meta piece of advice is your don't be the best, be the only. It seems like in business, in creating, in family, in career, in spirituality, this is the advice to end all advice. Do you think that's right?

• 1:02:28Speaker 02

  I think that's right. Again, that came from my time at Wired. We'd have story meetings every month and we were trying to make assignments to story ideas that we had. There was three editors and I'd have these ideas like, this is a really great story. We got to find a really great author, writer for this. This is a really great story. And then Nobody else in the room thought it was a good idea. It's like, I don't know, this drug or nah, or that's nope, get that. And so I would kill that idea and go on to the next idea. They got more ideas. Okay. So we do more ideas, but then maybe a year later, you know, that was a really good idea. I really think we should do this. It's still valid. This is really important. I think this would be a great piece. In this case, it was like, nope, I don't get it.

• 1:03:13Speaker 02

  What's the point? If it came back a third time after me trying to kill it, if it came back a third time, I would say, let me try it one more time. And if it got killed the third time, then I would say, oh, I get it now. This is a piece that I have to do. I have to write this one because I can't give it away. I think it's really important. I'm the only one who kind of appreciates it. And so those are always my best pieces. It was like, oh, and then when I'm writing it, it's like, there's no competition. But I've been trying to give it away for years. There's no competition. So I can just do this. And it's easy because it's me. And so there was a sense of like, okay, I'm the only. And so when I go on from that, what I learned was to always ask myself, yes, this would be fun to do.

• 1:03:57Speaker 02

  Yes, I'm really good at this. Yes, I could get paid to do it, but is there anybody else who could do it? And that's true in business as well. Because if there's someone else doing it, then I don't want to do it. I want to go on immediately to the thing that no one else is doing, the only. Because the best is highly competitive, only one, number one, and you can easily be displaced and become number two instantly. And so you want to be in this direction where you are working, doing things that you find easy, that other people find hard, that only you appreciate. And so that's true for companies too. You really want to be doing something, not trying to become another OS, another social media app.

• 1:04:41Speaker 02

  Come on, those are occupied. Those are occupied by players with network effects. You're not going to work there. You want to go in a direction that's the only. And asking yourself, if you have competitors.

• 1:04:55Speaker 02

  They can be good, establishing a field and bringing credentials and believability to it and a market, but the advantage that we had at Wired was that we didn't have any other, we were so only at the time, there was nothing else like it. And it was hard because trying to sell advertising was impossible in the beginning. That's the business, it's not subscription, but advertisers. And there was no category. Wired didn't fit into any category. It was like incredibly difficult sell. Newsstand didn't want to carry it because there was no category. Where do we put this magazine? Computer? No, no, it's not a computer magazine. It's technology lifestyle magazine. What's that? There's no category for there. So it's hard. It's really hard to be the only in that sense. But if you can, the rewards are very, very high.

• 1:05:39Speaker 02

  And I think that's where you want to aim. Your life, your family, your company, country.

• 1:05:46Patrick O'Shaughnessy?

  I think it's amazing that the advice in the book is somehow both counterintuitive and obvious. And just like to sum up what I take from this, it's the smartest strategy, even if you're trying to be selfish, is to be generous and unique. And almost everyone does the opposite of those two things, which is totally bizarre. It's also a wonderful excuse to ask you the same question now I've asked, I guess, approaching 500 times now, I've asked every single guest I've ever talked to. What is the kindest thing that anyone's ever done for you?

• 1:06:14Speaker 02

  When I think of kindness, I think of a moment many, many, many, many, many years ago, when I was traveling in the Philippines, when the Philippines was an incredibly poor, developing country. There was not even a good map to the country. There was no guidebook, literally nothing. And I was traveling, exploring there, and I arrived somewhere at night, no idea where I was going. I don't even remember why I arrived there, but what happened was some family living in a grass hut waved me in. And I remember that they went and gave me dinner and they sent a kid out, which I saw, to buy some canned food somewhere because they didn't have food.

• 1:06:59Speaker 02

  Themselves and they took some very, very precious cash I could just see to buy food for me. It was for me to eat unbelievably kind. It was like, I don't know, like some random person walks by your house and you're gonna empty your life savings to give to them. So obviously I had far more than they had and I could have bought my own food, though there wasn't really much for sale. It was like a little tiny canned fish, but it was incredibly precious. And this is what they're giving me is they're giving me like canned tuna fish with a fork. They're feeding me unbelievably kind. I just still remember that because they were giving not out of their surplus, but out of their basic

• 1:07:41Speaker 02

  needs. So it was not a luxury. It was really, really powerful. And they had no reason to do it. It was this hospitality. It was really incredibly kind.

• 1:07:49Patrick O'Shaughnessy?

  Well, I'm so thankful for the conversation today. I'm so thankful for all that you've written and put into the world. Please know it affects people like me all over the place and makes us think for the better and hopefully act for the better too. So Kevin, wonderful to meet you and thank you so much for your time.

• 1:08:03Speaker 02

  Been a pleasure. I really enjoyed this. You ask great questions. I love your spirit. Thank you for having me.

• 1:08:09Patrick O'Shaughnessy?

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