Kevin Kelly - Be Generous and Unique

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 Floundermode. 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 open AI, cursor, perplexity, versel, plaid, and hundreds of other winning companies all have in common? The answers that they're powered by today's sponsor work OS. 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. Work OS 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, Work OS is the fastest path to becoming enterprise-ready and on-lock growth. It's essentially striped 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. Work OS 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 Oshanasi 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 join Colossus.com. Patrick Oshanasi 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. 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 so 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 for 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. 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 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 in 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. 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. 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 would have been easier if this goes back to the subtitle of my book. It was to my wish had known earlier. I wish I'd known this earlier that that's sort of the framing of a good life is to think 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 8 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 your journey. And I think that 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 can be doing that every day and not even have this articulation of trying to come to some essence of ourselves. But I think it's helpful if we can articulate it that way. 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? It's a great question. I haven't done that exercise, but let me 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, it'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 part of like branding exercise in marketing, which is that you actually want to control the message rather than having people interpret it. And so we learned this at Wired that we actually 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. And so I think if I was 30, 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 view. 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 30, 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, sir, if I'd never really done it very seriously, and I think that would have accelerated the clarity ahead of the choices that 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. 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 who 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 people's 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? It's possible that all the candidates, the Jesus was one who, the day before he died, was most authentically himself. I think you're right. A lot of people 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 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 authentically is going to be slightly different and weird. And the way I'd 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 Steve Jobs metrics. If they aren't different than they haven't really achieved that thing of being authentically unique. Or 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 who's 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 their family don't even know who they are, but they are 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. 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 counter forces are enormous. So what in your experience are those things that most commonly stop people from getting down this path? 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. 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 is 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 seed job. So a lot of people want to be Steve Jobs. Wrong? First of all, 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 an 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 is 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. Well, whatever it is. And you're saying, I don't think that's successful. And part of it is you're educating people about that. Other people so that you have the kind of support that you need 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. Do you think that surrender is 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. Yeah. And I have a little bit of wisdom in the book saying, you know, the thing that made you weird as a kid, it make you great as an adult if you don't lose it. And the problem is that most of the time you're losing, you get to beat out of you. You're a 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 paradigm. There's a lot of paradise. But one of the weird paradox is that you cannot truly become yourself by yourself. You can only become unique with the help of everybody else. That is the paradox. All right. It's like it's not like you're going to become unique on your own. No, it never happens. It takes everybody to make you unique. You can't 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 going to ignore everybody that anything says and you're on your own. You're not going to get there. Why do you suggest that people prototype their life versus drawing up grand plans? 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, 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. And so that's the one other 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 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 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. 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. Is that another cut at this your advice, 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? It's very close because follow your bliss for most people. They don't know what to bliss is and it kind of is paralyzing. But you master something in 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. And it's necessary, but not sufficient to get things done. What in your life do you think you most mastered? But 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 of 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 was happening. A land in the city. And I could tell over here, there's going to be something interesting happening. Kind of like the old Polynesian navigators, you could see the waves intersecting. I could see waves of people moving in certain directions. I could just pick up little posters. Let's like those geoguester 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. Is that a pretty obscure mastery? But from that photography, visual storytelling, that could lead to other things. It might be was a Napoleon movie where his skill was tasting milk. It's a very rarefied mastery, but I think more generally I have mastered it wired in a horse in the newsletters. I'm mastering a sense of trends. I would say a sensibility of the future. A future sensibility. My mentors like Stewart Brand was very good at this. And my partner at QuilTool's Mark Franfelder are very good at 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. I had a whole chapter on digital money. I gave that chapter to Steven Levy and the first issue of wire 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. You had to describe the energy signature of those things when you spot them or feel them. How do you encapsulate that in words? 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 breath 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 breath to the possibility space that it suggests. And secondly, I think there is some detection of how fast things are being uncovered, like 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 in 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 the sense of well, there's nothing discovered that we could kind of imagine is scaling up into something bigger. And so you're looking at the recent past to see what's the rate of new things. 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. You can't describe it well or easily. Right. And so that's another sign that it's worth paying attention to. I love those ideas. It's 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 do they play out in your own life? Absolute above that idea. So it's related to another piece of advice in the book, which is actually talked with this with David Allen, the Get Things Done Guy, which is that there's a kind of a mispronunciation 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 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 can flate lots of things in the word work. That sounds bad. Yeah, there's often very negative, but then you have the great masterworks and great work. And so we have both meanings. We're sometimes conflated, maybe we 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. How do you think about money and thoughts so much about work and self-expression and all these things and not following other's 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 to concept the thing, how you relate to it. In general, I'm very bored by money. I find very, very bored. One of my things about crypto, my son and my son-in-law, we're 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. You can't talk about making money, saving money, whatever it is. Let's talk about crypto without talking about money. It was a 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 with 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 of what money is. It's like gasoline for your car and the purpose of the gasoline for the car is to drive around. But you're not driving around the gas station 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 is completely imprisoning and a burden. Basically, it's a burden because it ends up owning them or for some other reason. 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. What's the difference between those two? 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. 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 or a house for whatever. You haven't spent any of that money yet. Tomorrow it's 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 getting factor for what most people want to do. There's a great scene and think it was a Wall Street or this guy going to Wall Street and his whole goal is 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 in McDonald's for six months, save enough money to buy a motorcycle to ride across China. You don't need to go into 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 misplace hurdle. Imagine there's not enough money because in fact, what we know about innovation is that all the real breakthroughs come from the places where there's not enough money. Startups. The reason why I start up 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. It's actually the benefit. And that's why when young people are starting off, they have very little resources. They don't understand they actually have an advantage over the established companies. That lack of resources is an advantage to them. 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 create tours. 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? Yes. I have slowly included, maybe this is a changing of the mind that almost any virtual or quality or talent can be improved. There's 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 climbed 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. 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 Brianine and I called gumthinkables to inhabit those kind of improbable worlds is a skill that has to be learned. It has to be regained. 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 with the consensus is that's a variable skill. And that kind of overwhelms our ability to imagine crazy weird stuff because we're not really rewarded for that. 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. 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 just because AI is capable of these orthogonal, weird directions that is very difficult for humans to let go of that much easier. So working with them to help us inhabit the possibility space in a different way, then we find it hard on our own because of our education and biases and capabilities. So that's what I see as one of the roles of some of the AI is assisting us in our imagination. I'd love a case study and imagination. When you think of the most imaginative person you've ever encountered, who comes most immediately to mind? What was their story? I know some writers, so fiction writers, who naturally can just go off and 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, we've never thought of that. They are, I believe, have trained themselves to do that. Like Marvin Miske, who was a very imaginative guy who used to pretend 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. Okay, well, what did it say about music? Why are you people so affected by music? It 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. I used to love that an Nintendo 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. Yeah. So there are various forms of imagination. But the point is that the possibility of space for ideas is very, very, very, very large. It's probably the largest possibility space that we can imagine. And we tend 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 ten steps away, it doesn't help anybody. There's nobody there. 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. But if you can't get to it in a couple 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. It 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 have 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 just adjacent possible that people talk about it. 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, you'll be a lot more useful if you could do something that was more adjacent. 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 rights of passage a lot. And it seems like the modern world is as low on different kinds of rights 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 a thousand years from now. Why do you think that's the case and what would be your prescription for changing it? I think traditional cultures are full of rights of passage. I have three kids now. I'm grown young adults and one of the things I know by kids who I learned was that they crave one of you 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 very uncertain process. It's very scary. They don't know what it means to be 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. 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 rights of passages are things that help that anchoring and something that they can return to even when things get scarier and certain 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 rights 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. And so rights of passage and rituals are something that have been medetted 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. This is the beauty of Burning Man. Burning Man as a ritual and the joke was always re-burned 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. If 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, or pizza on 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. And 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 is looking forward to it, if relying on it, having it be there, and that is the foundation of a stable development in their own personality. And so right to passage is another aspect of that. I think we found that just you have to invent them. You can use really just 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 or the passage that we did as a family. We had a bunch of rituals that we would do. And they became again another anchoring thing or kids understanding of themselves. 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 rights to passage for our kids. Let's say parents for the kids. Any other exercises for the family that you would recommend? 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, they're a definition of success. They're a definition of successful life. Well, the people that they want to respect are those they're 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 ranger 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 where you'd gratitude rounds and things. There's a lot. There's actually a good book called The Secrets of Happy Families by Bruce Eiler. 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. I'm just like, okay, that's fine. That's good. I understand that. That's part of my identity. And so you can do that. 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. Yeah, I'm not very good. I think you need to talk to Esther Peral who says in this couple's 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 something 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, then you say, is there more? And there's usually more. And then they go, rack second round, you listen all the way through. 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. 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 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. 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? I think I said it was a why person who said 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 necessary, I think? I mean, true, necessary and kind, right? Right. So if it's on 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 sinus strength. And you can't really be too kind. If you have a choice between being right or kind, you'd 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. It's like, wow, that's really powerful. That's what matters. Do you think that humans are naturally kind? I do. There's a great book called Human Kind 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 that the opposite in my own experiences 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. 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, that's true for everybody, than where does it come from, right? I mean, 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 your 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%, but every person who does this will tell you that the happiness and the satisfaction and your life's well-being will increase by 10 fold 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. I have a background in philosophy, and so I can't help myself, but focus on your advice that's very big and grandiose 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? 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 look for it. I repeat that to myself all the time when I'm putting things back, okay? Put it back where I first look for it. That's a bit of advice. 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, and so I use that to say no, I'm just imagining, okay, would I get tomorrow morning to fly whatever it is or to go into the, or to meet whatever it is, and if it isn't resounding, yeah, then it's a no. 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. 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. Did collecting all of this advice change your mind or change you in any material ways? I'm 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 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 or 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. I'd like to spend an interview 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've 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 technology called the Technium, the stock of technology that exists in the world, and why that's such a natural extension of human beings? In brief, the main insight about the Technium, which is my term, or 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. We use computers to make everything and maybe plumbing in the farmers to make the computers. And so, where is this web? This ecosystem of technology is 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, 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 of 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 a light and color the wants? 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 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 over here. Just helping it replicate. When a beaver makes a dam and birds make nest, those are technologies in a certain sense. There are outputs of the mind. And so, I see the cosmic arc of the story of technology which begins with the Big Bang and self-organizing systems and elements and stars and planets that have 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 mines. And there are many mines and out of the mines come other possible forms that can't be done with just water-based tissue. And so, I'm imagining that there's technology and other planets that have the galaxy somewhere and that they're all kind of following this thing of making more and more possibilities. 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 or the strands of the improbable, which are galaxies and stars and elements and planets and mines and technology. And it's all improbable and self-metaining. It keeps making things more and more improbable as long as it keeps going. 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 health care and they would need to realize the 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. Wonderful idea. Do you think that you're to draw the timeline of technology? It seems like we've harnessed information with the printing press. We've 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? Yeah, I mean, I think ultimately you'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 kind of learning. If you abstract it 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. There are 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. So, all the things 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 buyer 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 sety and beings. There were 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 sety being on the planet, the Hegemon. We're now going to go back to having other sety and beings. And we don't know today why were there 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 sety and 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 sort of long term. In the short term, we have AI of a very, very narrow sense of pattern recognition and pattern generation. We synthesize one type of cognition, which is pattern recognition pattern generation. And all the things we're seeing today, only because we synthesize that one single kind of cognition. 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. And 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 while you're here? What do you do that nobody else can do? Now we're going to have that at the species level. What are humans for? Why are we here? What are we good for? What can we do? The others can't. And then we have genetic engineering. Well, we can actually change our own bodies. And so what is it that we want to become? 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, 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. Is there anything else that you think is over or underestimated about what's happening in this technological change? 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. We think that thinking is the most important thing in the universe to get things done so it's not necessarily the most important. But take Einstein and a tiger and put them in the 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 and the people who imagine the smart, genius AI thing or what I guilty of think is them in the sense that they think that thinking trumps everything else and it doesn't. There are so many of the things that you need to accomplish something to have effect on actually making things happen including empathy, including perseverance and all kinds of things. And so a lot of the fears of the existential threat of the AI is 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. I mean, this is why you only want to have 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. One of the things that I remember distinctly from my teenage years was my two favorite magazines were called 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? One thing I learned about magazines was that the best magazines at the best times because magazines, you know, live 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, the 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 soul person, usually, if they have any kind of cloud, 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, 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. 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. When you were running wired and wired, obviously, was like the expression of your taste and personality, what practices or what did you do to protect that? That seemed incredibly desirable in any publication that it's like the taste of the person magnified or something. Yeah, we projected it by owning more than 50 percent of which we lost. Very terrible, terrible story. We lost control, and that's why we had to sell this when we all left. Okay, we left. Not because it wasn't funny more, 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 wire, but I did learn that there's a bit of advice in my book about what we learned from the ad, retising people, which is to get your message across, 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 wire story or not. There's tons and tons of directions to go. And so being able to brand it in that sense was us being partly enabled by articulating it ourselves and being able to do that. You think then like it's so interesting thinking across our conversation how maybe the metapiece 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? 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, these are a really great story. We get 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, it's grugged or nah, or that's, nope, get that. And so I would kill that idea and go into the next idea. They got more ideas. Okay, so we do more ideas. But then maybe a year later that, 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. On this case, it was like, nope, I don't get it. What's the point? If it came back a third time, I have to, me trying to kill it. If it came back a third time, I would say, let me try this 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 were always my best pieces. It was like, oh, and then when I'm writing it, it's like, there's no competition. 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. 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 has in the best is highly competitive, only one number one. And you could 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, the other people find hard, the 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. 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, they can be good, establishing a field and bring credentials and believability to it in a market. But the advantage that we had at wire to is 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. Why didn't it do any category? It was like an incredibly difficult sell. New stands didn't want to carry out because there was no category. Where do we put this magazine? No, no, no, it's not 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. And I think that's where you want to aim your life, your family, your company, country. I think it's amazing that the advice in the book is somehow both counterintuitive and obvious. And just to sum up what I take from this, 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, purchasing 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? When I think of kindness, I think of a moment 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 weren't giving me dinner. And they sent a kid out, which I saw, to buy some canned food somewhere. Because they didn't have food themselves. And they took some very, very precious cash. I could just see to buy food for me, for me, unbelievably kind. It was like, I don't know, like some random person walks by your house and you're going to 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 don't remember that because they were giving not out of their surplus, but out of their basic needs. So it was not the luxury is really, really powerful. And they had no reason to do it. It was this hospitality. It was really incredibly kind. 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. It's been a pleasure. I really enjoyed this. You asked great questions. I love your spirit. Thank you for having me. If you enjoyed this episode, visit JoinColossus.com where you'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus Review, our quarterly print digital and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at JoinColossus.com/subscribe.