Building Wired Magazine: Kevin Kelly’s Unconventional Path from College Dropout E139

Summary

Leap Academy with Ilana Golan
Episode 139: Building Wired Magazine: Kevin Kelly’s Unconventional Path from College Dropout
Release Date: December 23, 2025
Guest: Kevin Kelly (Co-founder of Wired, Co-Chair of Long Now Foundation)

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Episode Overview

In this fascinating episode, Ilana Golan interviews Kevin Kelly, co-founder of Wired Magazine, writer, futurist, and co-chair of the Long Now Foundation. The conversation traces Kevin’s non-traditional path: dropping out of college, forging a life out of curiosity and intentional choices, and building one of the most iconic magazines in the tech world. Kelly shares key lessons from his global travels, creative ventures, founding Wired, the philosophy behind his “1000 True Fans” concept, and how the awareness of mortality has shaped his drive and optimism.

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Key Discussion Points

1. Kevin's Bold Leap: Leaving College for Experience

• Context (02:32–06:01):
  Kevin describes his decision to drop out of college in the 1970s, a time when it was considered a radical act. He felt formal education wasn’t for him—he craved real-world, hands-on learning.
• Quote:

  “I was going to trade a career that would have money... for having control over my time. I may not have money, but I will have time and I will make my art and I will do my stuff…” — Kevin Kelly (03:12)

• He was inspired by the Whole Earth Catalog, which showcased alternative, do-it-yourself lifestyles.
• Family Reaction: His parents were concerned, both for him and as eldest child influencing his siblings.

2. Adventures in Asia: The Real University

• Photography and Travel (06:40–09:48):
  With inspiration from Walt Whitman’s Leaves of Grass, a letter from a friend, and his love of photography, Kevin set out for Asia—a rare move at the time. He credits this travel (especially Taiwan and Japan) as his true education.
• Cultural Immersion:
  Experiencing radical newness, learning to navigate without English, and embracing the openness of local communities.
• Quote:

  “Asia became my college, that became my university.” — Kevin Kelly (08:47)

3. Defining Wealth: Control Over Time

• Philosophy (09:36–10:29):
  Kevin equates wealth not with money, but with time and autonomy.
• Quote:

  “That time is wealth. That’s the true wealth. True wealth is you gain control of your time. And I had that. I’ve always felt that. That I am the richest person in the room because I have control over my time.” — Kevin Kelly (10:10)

4. Serendipity & Skills: From Budget Travel to Publishing

• Early Entrepreneurial Ventures (14:37–16:41):
  After returning from Asia, Kevin created a mail order catalog for budget travel books, importing titles like The Lonely Planet Guide.
• Skill-Building:
  He learned writing by following a library book’s instructions, transitioning from photography to words, a lesson in learning by doing.

5. Magazine as a Manifesto: The Birth of Wired

• Origins (11:04–12:40, 21:45–28:46):
  Kevin and his co-founders, “all unemployable at that time,” built Wired to be the magazine they longed to read—straddling tech, culture, and innovation at a time when technology was not mainstream.
• Trouble Defining the Category:
  Wired didn’t fit existing magazine racks or advertising models. Resisted being labeled a “computer magazine.”
• Quote:

  “We’re not a computer magazine. We’re a lifestyle magazine like Rolling Stone... What about the culture around technology?” — Kevin Kelly (25:11)

6. Inventing the Future: From Guerrilla Marketing to Internet Firsts

• Marketing Innovations (27:29–28:46):
  Guerrilla tactics: distributing Wired at Macworld (even getting kicked out for not having a booth), covering buses for attention, and using color and bold design as a statement.
• Internet Pioneering:
  Wired innovated with daily online publishing and invented the clickable ad banner.
• Quote:

  “We hire for aptitude, train for skill... no one had the skills we actually needed.” — Kevin Kelly (22:18)

• Facing Skepticism:
  Early employees were wary of internet advertising; commercializing the web was controversial.

7. Highs, Lows & Legacy: Wired’s Business Evolution

• Dot-Com Era & Company Split (32:09–33:42):
  During the tech boom, Wired’s digital side was valued far more than the print magazine, leading to controversial investor-driven breakup and sale.
• Why Kevin Left:
  As the business grew, he stayed focused on editorial and creativity, avoiding burnout and refusing to relocate or be consumed by business drama.
• Editorial Philosophy:

  “I told the writers, look, you’re not writing for your grandma... Your audience is me. I read everything and I am totally bored and you have to amaze me in some way.” — Kevin Kelly (35:17)

8. The 1000 True Fans Philosophy

• Origin and Impact (37:52–42:37):
  In 2008, Kevin formalized an idea vital to the creator economy: If you have 1,000 true fans—people who buy everything you make—direct relationships can sustain creators without mass-market hits.
• Quote:

  “If you have true fans and you can sell them at least $100 worth... that’s $100,000, which is kind of a living for most people in the world... It's an alternative to having to have a million fans.” — Kevin Kelly (41:12)

• Not everyone is cut out for direct-audience management—it's a real (and rewarding) job.

9. Mortality and Focus: Living with a Countdown

• Profound Experience (44:32–48:36):
  Kevin recounts a life-changing experience in Jerusalem, where he lived as if he had only six months left. This shaped his perspective on time and priorities.
• Maintaining Purpose:
  He keeps a countdown clock to actuarially estimate his remaining days, using it to focus only on projects only he can do.
• Quote:

  “It's not depressing at all. It's very focusing... Do I want to use today to do this?” — Kevin Kelly (47:36 & 47:55)
  “Could anybody else do this? If somebody else can do this, they should. I only want to work on the things that only I can do or only I should do. And that's really, really clarifying.” — Kevin Kelly (48:42)

10. Art, Asia, and New Adventures

• New Creative Projects (50:10–52:33):
  Kevin describes his self-published book Colors of Asia, arranging travel photographs by color, defining it as “cool and useless… my definition of art.”
• China Focus:
  He shares insights from frequent travel and engagement with fans in China, including technology advances for travel (real-time translation earbuds) and stresses the West underestimates China's development.
• Quote:

  “I am big in China. And I have a new book out... It’s positive scenarios for China in the next 25 years. So I am paying a lot of attention to China. And I think people in the west... underestimate what China is doing.” — Kevin Kelly (52:33)

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Notable Quotes & Memorable Moments

• On Motivation to Create:

  “We were just making the magazine that we wanted to read.” — Kevin Kelly (00:00 & 11:16)

• On Entrepreneurship:

  “All the co-founders of Wired, all of us were unemployable at that time…” — Kevin Kelly (11:04)

• On Wealth:

  “True wealth is you gain control of your time.” — Kevin Kelly (10:10)

• On Opportunity:

  “I only wanted to work on the things that only I can do...” — Kevin Kelly (48:42)

• On Publishing:

  “Book publishers don’t have audiences anymore. And so this is a lot direct, more faster way.” — Kevin Kelly (51:08)

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Timeline of Important Segments

• 00:00–03:08: Kevin’s decision to leave college—cultural context & family impact
• 06:34–08:47: Decision to travel to Asia; how it changed him
• 09:36–10:29: Wealth as control of time
• 11:04–12:40: Origins of Wired Magazine and the “unemployable” founding team
• 14:37–16:41: Early entrepreneurial ventures in travel publishing
• 21:45–28:46: Birth of Wired, category invention, guerrilla marketing, struggles with advertising and identity
• 32:09–33:42: Wired’s split during dot-com era; reasons for leaving
• 35:17: Kevin's editorial approach: challenge and surprise
• 37:52–42:37: The concept of 1000 True Fans and its creator economy implications
• 44:32–48:36: Mortality, living with a countdown, and its impact on life decisions
• 50:10–52:33: Colors of Asia, self-publishing, and lessons from China

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Episode Insights & Takeaways

• Nontraditional Pathways: Embrace unusual routes—skills, credibility, and audiences can be built outside the system.
• Creator Economy Wisdom: Don’t aim for the masses; foster direct, passionate connections.
• Risk & Resilience: Industry-defining innovation often comes from outsiders (“unemployable” types) who break categories, ask new questions, and withstand failure.
• Purpose & Focus: Use the awareness of limited time as a focusing tool for true impact.
• Global Mindset: There’s immense value in approaching new cultures with openness and humility; the world remains much larger than any single narrative.

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Listen If…

You want to be inspired by a tale of self-invention; are curious about the intersection of tech, culture, and publishing; seek wisdom for the creator economy; or crave practical, empowering lessons for entrepreneurship and finding your unique life path.

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Find Kevin Kelly at kk.org
Colors of Asia book: kk.org/colors (Limited editions)

[All timestamps MM:SS based on episode transcript.]

Transcript

[Kevin Kelly]

All the co founders of Wired, all of us were unemployable at that time and we were just making the magazine that we wanted to read.

[Host / Interviewer]

Kevin Kelly co founded the Wired magazine. He is a writer, he's a futurist, he's now co chair of Long Now Foundation.

[Kevin Kelly]

I wasn't like anti college, it was just like this is just not for me. I needed to work on something real. I just could not sit in a classroom. I was a science nerd and an art nerd and I took all the science and math classes, doubled up and I took all the art classes. That's all I was interested in. And photography was sort of something that was a combination of those. Technology was not front page news, it was not covered by every single publication like it is now. Wired was its own new category that didn't exist. That's good news and bad news. The good news is it had no competition.

[Host / Interviewer]

The bad news is that you mentioned that you should have been dead. What was the experience? Why was it profound?

[Kevin Kelly]

I was given or took on this assignment to live as if I was going to die in six months. I did everything that I could to prepare for dying in six months. And one of the things that came out of it was.

[Host / Interviewer]

Okay, our guest today co founded the Wired magazine which I bet you all know or heard of and he is a writer, he's a futurist and he's an incredible optimist. You'll hear it. And he's now co chair of Long Now Foundation. They're building a clock and library in the mountain that will last for 10,000 years. My head is like, like how can you even think about 10,000 years? It's incredible. And I can go on and on and on and endless cool stuff that Kevin is involved with. Kevin Kelly, Tim Ferriss actually called you the most interesting man in the world if I'm not mistaken. And I can't wait to dive in. So welcome to the show, Kevin.

[Kevin Kelly]

Well, it's my pleasure, my honor, thank you for inviting me.

[Host / Interviewer]

We're going to geek out. I already told you, like we are going to geek out. But I have to say you started, if I'm not mistaken, actually dropped out of college, do not have necessarily a college or university degree and I want you to take me there. Like what were you planning to do? Did it scare you? Did it scare your parents? Take me there a little bit.

[Kevin Kelly]

Yeah, it's worth going back because in 1970, in the 60s when I was going through high school, everybody went to college, people moved to the town to go to high school, to go to college. And not going to college was a very, very deliberate act then because there was no gap year, there was no internships, there were no alternatives. It was college or nothing. And when I dropped out, it was kind of like signing up for not having a career.

[Host / Interviewer]

It's like signing up on failure. How do people take it?

[Kevin Kelly]

Yeah, so I assumed that. I mean, when I was trading, I was doing a deliberate trade in my mind. I was going to trade a career that would have money and not even wealth, but just like a livelihood for having control over my time. I was imagining that I would be doing things like building my own house from scratch, which I eventually did.

[Host / Interviewer]

Oh my God.

[Kevin Kelly]

And other things that I would do with the time. And in part, I have to say, by the time I was graduating, I had the whole Earth catalog in hand, which was for me, this alternative. It was a catalog of possibilities that were alternative to what people were expecting you to do as a career. And it said, here's a bunch of people who have taken alternative careers in their lives to build their own homes and all these other kinds of things that I wanted to do. They said it was possible. It was saying there is alternatives or there are alternatives that are possible. And that's what I believed in. I said, yes. There seems to me there are other ways. And I may not have money, but I will have time and I will make my art and I will do my stuff and I will make my things.

[Host / Interviewer]

Was there a lot of no's from people around you or the family and what are you doing now? It's a little more common now. You see a lot more of it. It wasn't as common when you did that.

[Kevin Kelly]

No, it wasn't. I didn't meet anybody who had gone on to career that had dropped out until Silicon Valley when people started to do it more often. My parents were very concerned about it because I was the eldest of five. They were afraid of the influence I would have on my siblings. They weren't concerned about me. They realized that I was just sort of on my own path the whole way. They wanted the others to go. And I made it clear I wasn't like anti college. It was just like, this is just not for me. And I had the same conversation with my three kids when they were getting to that age, because my wife is Chinese, she's overeducated the whole way. And so this was the one area where we had some disagreement. And basically I took my kids to the side. You don't actually have to go to college. There's actually a way you do have to do something. So if you can come up with a program, internship, if you have some art you want to do, if you want to travel, whatever, you give us a program and we'll support you for that year.

[Host / Interviewer]

That's power.

[Kevin Kelly]

But if you don't have anything, then you have to go to college.

[Host / Interviewer]

And was there a moment where you decided that? Was there an evolution of things?

[Kevin Kelly]

I was very unhappy. I did a year college, and it was grade 13, and I was sitting in the classroom. What I needed to do was I needed a gap year. I needed an internship, I needed a project. I needed to work on something real. I just could not sit in a classroom again. And so I was doing all kinds of things. I had all kind of projects I was doing at college. And I realized I don't need to be here to do that because I'm just. I just can't sit in. I can't sit. I gotta make stuff. I have to do stuff.

[Host / Interviewer]

So when do you decide to travel all the way to Asia? Because that was not common in those days either.

[Kevin Kelly]

No, that was huge. Huge. I'd never even eaten Chinese food before. I never had chopsticks. No, no. I mean, literally, I'd only eaten at a restaurant a couple times in my whole life. I mean, I didn't meet people who were coming back from Japan. Nobody. This was very, very, very, very rare. And what happened was I decided to do photography. I was doing photography in high school, which was at that time, very, very technical. So the only way you did photography, you did the chemistry. So I was a science nerd and an art nerd. I had both. And I took all the science and math classes, doubled up, and I took all the art classes. That's all I was interested in. And photography was sort of something that was a combination of those. To do photography then you had to do the chemistry, the optics, all things manual. It was very, very technical. And that's what I was doing. And I decided to follow more of that. So I did a residency where we worked for three months. And I did photography every day. Developing and doing it in a photography residency, upstate New York. And I started to do things, and I did a whole year of reading books, the great Western canon books. And I read Walt Whitman's Leaves of Grass. And it blew my circuits because I was seized by the desire to travel. From reading that poem, this ode to America, and all the kaleidoscopes of occupations and people doing stuff, it's like, oh, I just need that. And. And at the very moment my best friend from high school wrote me a letter saying he was studying Chinese in Taiwan to become a missionary and that I should come visit him. And I thought, okay, I want to photograph. I'll go to Taiwan to photograph. Having no clue what that actually meant or anything. I'd never been out of New England, and I went through Hong Kong and arrived. It was like my mind was just so, so blown in so many ways.

[Host / Interviewer]

It is a different world.

[Kevin Kelly]

It was on another planet. So that became my college, that became my university. Asia did.

[Host / Interviewer]

Is there fear, though? I don't know how to make them a dime. I don't know how I gonna sleep the next day. Like, is there fear there?

[Kevin Kelly]

No, there wasn't fear. And particularly Taiwan or later Japan were some of the best places because they were perfectly safe. There was, like, no crime. And they also have a very different sense of privacy where I could basically walk into anybody's courtyard or shop or factory. And even though I was Martian, there was no sense that I was trespassing. I would just arrive and walk into things. So that maybe influenced me where there was this sort of welcoming wait.

[Host / Interviewer]

So you walk into things and you stay there?

[Kevin Kelly]

No, no. I mean, actually finding hotels was hard because I couldn't read the signs. There was no English anywhere. So I have to decipher. I have to learn the characters for a hotel. And I would be looking around. I couldn't really even ask. I had a couple hundred dollars. I later went to Japan and hitchhiked for five months, staying at youth hostels. I had only enough money to pay for the youth hostels was like, I don't know, three or four dollars. And you could eat all the rice you could eat in the morning. And hitchhiking for free. So I didn't have money, but I had time. And that time is wealth. That's the true wealth. And people confuse that with the rich riches of money. True wealth is you gain control of your time. And I had that. I've always felt that. That I am the richest person in the room because I have control over my time.

[Host / Interviewer]

Well, I think of wealth as freedom of choice. And I think that part of it is time. Part of it is just the fact that I can choose to be in Asia. And I think that bug, you know, we'll talk about it, because you find yourself in Asia, like, you actually have a map, a really cool map on your website of all the different areas that you've been. And it's Fascinating. So what are some of the big lessons that you feel like prepped you for later on? And how did you get into editing and publishing? What was that journey like?

[Kevin Kelly]

I really was unqualified to do what I wound up doing. And by the way, all the co founders of Wired, all of us, were unemployable at that time.

[Host / Interviewer]

I love that.

[Kevin Kelly]

No, we absolutely were. Nobody would have ever hired us. And we were just making the magazine that we wanted to read. I was on the path to become, like, a professional photographer. And I was very interested in, I thought, working for National Geographic, and I was showing them my work, working with the photo editor there. And I was on a track to shoot for them professionally because my work was good enough and I had an interest. But what I realized after hanging around the professional photographers was I didn't actually want their job because they were on assignment and they were often photographing things that they didn't really want to photograph. They didn't have total control over it. Some of them had more control than others, but they were often still shooting things that had to be shot rather than they wanted to be. And I just decided that I didn't want to be, that I liked the kind of freedom of choice to choose what I wanted to photograph with and then I would do something else. And I started to write a little bit about my travels after I came back and I started to have an interest in writing. So I did what anybody would have done at the time. I went to the library and got a book about how to write magazine articles.

[Host / Interviewer]

Really? Oh, my God, yes.

[Kevin Kelly]

And I followed the procedure and I wrote my first article and it was accepted. That's how I learned. And that's what I got into reviewing and culturing at Whole Earth. Whole Earth was the resource that I wish I had earlier in life. And it was the precursor to the Internet. So before there was Internet, there was Whole Earth, which was really the only place you could kind of find useful, practical information. And again, going back to, like in high school, the thing about then was the lack of information, the poverty, the desert of ignorance was huge. There was no way to look something up. If you wanted to know how to do something, start a business or build a deck on your home or where would you go? Where would you go? And that was beginning to change with the Horth cattle. And that's why, because I was a maker. I was a kid making things, and I just needed that information and it wasn't there. I didn't have older brothers. And so when that started to arrive. That's where I really thought that there was something happening.

[Host / Interviewer]

I want to take you there. And it's funny because we literally just had Jimmy Wales, the co founder of Wikipedia, on which is kind of funny because he's mentioning also there was nowhere to look for information. But I want to take you. Like at some point you're moving from maybe publishing from time to time and traveling and correct me if I'm wrong, but then you start driving, you create this hacker conference 1984. I don't think we even knew what entrepreneur is. The name didn't exist. Hackathons, things like that didn't exist. How did you even think of that? What got you intrigued by it?

[Kevin Kelly]

When I came back, I hiked the Appalachian Trail with my two brothers. Two of my brothers, I have three brothers. And it was just after I was back and I was part of the trip was to reconnect with them as adults. We were all very close, just a year apart, but also for me to kind of like think about what I wanted to do. And I remember on this hiking along, we had lots of time at night sitting around the stove. And I came up with the idea that I would do something with travel because I was like the only thing I really know more about than anybody is budget travel. I know that. So I started both to my own little business to have a mail order catalog of budget travel guides. These travel guides that I knew about from traveling in Asia. One was put out by this Australian couple, Tony and Maureen Wheeler. They had a little book, it was called the Lonely Planet Guide. Oh my God.

[Host / Interviewer]

I didn't realize that. Oh, that was my bible.

[Kevin Kelly]

They're printing it in Singapore. And then there was this other guy who had Europe through the back door and Asia through the back door. His name was Rick Steves.

[Host / Interviewer]

So cool.

[Kevin Kelly]

And so I had his little book and then I had the Indonesian guy by this guy named Bill Dalton who had Moon Publications. So I was importing these little self published guys at the time who had their own little self published stuff. And I had a mail order catalog of all these cool books that you could not find in bookstores or libraries. And so I was starting a business. I worked in a science lab. I had an Apple II computer, which I was, they had for data. I was learning to use that. And so I came through it that way. I was hippie, not interested in technology and I didn't really own. I had a bicycle and a camera and a sleeping bag and that was literally all I owned. When I came to San Francisco.

[Host / Interviewer]

We need to pause for a super brief break. And while we do, take a moment and share this episode with every single person who may be inspired by this, because this information can truly change your life and theirs. Now I want to check in with you. Yes, you, are you driven? But maybe feeling stuck in your career or a fraction of who you know you could be? Do you secretly feel you should have been further along in your income, influence or impact? Do you ever wonder how to create not just a paycheck, but the life you want with a paycheck? The thought leadership, the legacy, the freedom. Because that was me. And that's exactly why I created the Leap Academy program, which already changed thousands of careers and lives. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. Aq, adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training. Check out this completely free training about ways to fast track your career and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com training. I actually have a fun fact for you, which is funny because you reminded me I didn't even think of that. So my mom wrote the first ever guides to Europe and US in Hebrew from Israel. I think that was like in the 60s.

[Kevin Kelly]

Yeah, yeah, yeah. I wrote a piece very early on 1984. I was doing a travel column for, for a magazine called New Age Journal, which was New Age stuff. It's kind of hippie ish, but whatever. But they were kind of broader. And so I had a travel column and I did this cover story for them in 84, probably wrote in 83. It was called Network Nation. And what I was doing was I was going around to all the emerging online systems and I was saying, there's a new country arising. I wrote it as a travel guide to this new country called the Network Nation. And I was doing like a travel tour guide thing as if it was a new place. And that's how I was sort of approaching it in the beginning, was as if it was a new continent. And that got me hired at Whole Earth and they were beginning to do networks. And then once I was there, things happened very, very quickly. There was a book by Steven Levy on hackers, the good kind of hackers at MIT who were kind of hacking things. And I read the book and I realized that the three generations of the people he talked about had never met. So I said, why don't we bring them together? And that was the origins of the first hackers conference. We just had a weekend and we brought them together and we just listened to them talk to each other about what was important. That was sort of the origin of later on, all the nerd conferences where you brought them together and let them talk about whatever they wanted to talk about. You were listening.

[Host / Interviewer]

I was one of the nerds. Kevin.

[Kevin Kelly]

Yeah, exactly. So that's how it began. And in the beginning, John Markoff, the New York Times writer, wrote a book which was poorly titled, which was about the hippie origins of Silicon Valley. So there was a huge overlap between the long hairs who had dropped out and started little businesses making candles or macrame. And what they were learning were business skills that you didn't get by being a manager for a big company. They're making their own little business selling pottery or whatever, and they're getting the business skills. And that transferred into the moment when they started doing tech stuff. So, like the guys on the farm, there was a whole bunch of people in San Francisco that went as kids. They went to a farm in Tennessee and they were living as communists. This was a commune. They had no money, their own money. They literally had communism working and they had families and everything. And they raised farm and their women were midwives for a fee. And the guys, they learned that they could do tech support, like CB radio and other kind of stuff. They got into the tech thing. And some of those people came back to San Francisco and were looking for a job. And those are the people that we hired to start our own online conference. So our own online conference were run by people who had grown up on communes and new tech stuff. The very, very beginning of tech stuff.

[Host / Interviewer]

Yeah, because it was way back. Like, I mean, again, I was a kid, but I think even when you co founded Wired magazine, it was 1993, the web was literally like, we help invent the web. Exactly.

[Kevin Kelly]

Not the Tim Burns Lee protocol, but like the click through ad banner that was Wired. Wired invented that. So all those kinds of the daily publishing. So we were right at the present of trying to make that work. And we were hiring people. Okay. Nobody was trained to web designers. It was like, who do you hire?

[Host / Interviewer]

So how do you get something like this off the ground? Again, this is a magazine. It's insanely tricky. People will say it's impossible to get funding, impossible to market. How do you even make that happen?

[Kevin Kelly]

There was two parts. There was the magazine, but we were also doing the online side. So from the very beginning, we had a daily website. Who knew how to program a website? Nobody. Where do you even get the people to do that? So we are training people. So I had this little phrase, we hire for aptitude, train for skill, because nobody had the skills that we actually needed. It was not a very good time to raise money. And we had plenty of near death experiences. And in fact, we had a failed ipo, which is why Wired was broken up and the digital side sold separately from the magazine side.

[Host / Interviewer]

Can I take you there for a second, Kevin? I know that we have a lot of people that they want more. They're seeing maybe some things. There's AI. There's like all these changes now, but it scares the heck out of them to jump in and do it right because there's a lot of fear, like, will it work? What if it doesn't? Like, so can I take you back in time to somewhere around 1993 or maybe a little before? Where is your headspace? Do you understand how risky it is? Or you're just so optimistic that you just take me there for a second.

[Kevin Kelly]

So I was already editing a magazine, and I bet the CFO that I would never see any money from Wired. I bet him a dinner, said, this is very, very unlikely to succeed. But out of all the ideas, I'd said, this is the most promising one. Because Lewis and Jane, Louis Rosetta, Jane Metcalf had done a prototype of the magazine that had funded Nicholas Dingapani at Media Lab, had given him some money to do a prototype. And when I saw the prototype, I realized that this was going to work. Louis had a great thing that he said that sold me at that instant, I was already editing a magazine already. And so he said, I want to make a magazine that feels like it was mailed back from the future.

[Host / Interviewer]

Wow, I love that.

[Kevin Kelly]

And I said, okay, let's go. All right.

[Host / Interviewer]

Oh, so good.

[Kevin Kelly]

That's the one I want to work on. But I felt that this was very unlikely to succeed just because I knew enough about magazines. My dad actually worked for a magazine. Oh, wow.

[Host / Interviewer]

Okay.

[Kevin Kelly]

I grew up on magazine. I was a magazine junkie. No, I literally was. I was a total magazine junkie. I knew magazines besides travel. The thing I knew a lot about was magazines.

[Host / Interviewer]

So tell me about the beginning. Because again, the beginning, like, there's still no funding.

[Kevin Kelly]

Everybody brought their own computer in, which were not just laptops. They were big things. You had to bring your own computer. We were bimonthly at the very, very beginning for the first year, every other month. The problem was Wired was this own new category that didn't exist. That's good news and bad news. The good news is they had no competition. The bad news is that the people who put the magazines out on the racks don't know where to put you, and the salespeople don't know where to sell ads to. So they wanted to put us next to Bite magazine, which had pictures of chips on the COVID It was a computer magazine. No, no, no. We're not a computer magazine. We're a lifestyle magazine like Rolling Stone. And they said, well, Rolling Stone's a music magazine. No, no, no. Rolling Stone is not about the music. It's about the culture around music. What about the culture around technology? So there was a really big struggle.

[Host / Interviewer]

You're inventing a category, which is insane.

[Kevin Kelly]

And the thing about magazines is they're a weird thing, is because the real customers are not the readers, it's the advertisers. Okay. And so you're having to sell to the advertisers and what kind of advertisements want to be in the magazine. And Lewis was very adamant. He says, I want the liquor ads, I want the clothing ads. And they're saying, it's a computer magazine. And they're saying, no, no, no, this is different. This is a lifestyle magazine. And this is going to be the new lifestyle technology. And see, technology is teenage kids in the basement. No, no, no, no, this is different. We're going to make the nerds cool. The nerds are not cool, but we're going to make them cool. So it was a huge struggle to convince people that there was something there. And then because technology was not front page news. It was not covered by every single publication like it is now. It was completely left to a computer magazine that was talking about bits and bytes.

[Host / Interviewer]

But you have this incredible idea to launch it in the Mac World conference, if I'm not mistaken. And that's an insane understanding of marketing. Where did that come from?

[Kevin Kelly]

That was Louis. Louis was a really good guerrilla marketer. He loved that he had the whole thing of covering the buses. That was where he wanted to put his advertising dollars, make a big scene. He was really good at that kind of guerrilla marketing. And actually, we were kicked out of Macworld.

[Host / Interviewer]

Really? Why?

[Kevin Kelly]

Because we didn't have a booth. We couldn't afford A booth. We were doing guerrilla piggybacking on other people's booths that would allow us. And then actually, I stood out front with my daughter handing out magazines to anybody who came by. Walking by, we were passing out these. That's what we were doing. Just passing out the issues. And people would see these thing. And it felt like it was mail from another planet because it was in color. It was crazy. And there were things running this way and that way. It was sometimes hard to read. And it was like, what do you guys. I mean, what are you talking about? It was just, like, crazy. So that was 100% Lewis's guerrilla marketing genius. But it's a long road between getting attention to actually getting the money.

[Host / Interviewer]

Very long road. Is there a wife that says, done, let's cut the BS and start making money in a different way? Or no?

[Kevin Kelly]

No. It was. We began selling subscriptions, and that was enough to persuade people that this game would work, this little flywheel could work. And as it started to ramp up, so what happened very quickly, right after that was, of course, the web came Mosaic. And then the Mosaic was this, you know, the whole Netscape ipo. And suddenly people are looking around and realizing that there's money there. And so all of a sudden, the spotlight is on us. And literally every day while I was working, there would be TV crews coming through the office while we're working, asking us about, where's it going? What is it? So we were not only reporting on the news, we were in the news. And so that started to give us the attention in subscriptions. And then we were doing so well, and we started this. Lewis also firmly believed in the future of advertising online, and that was very controversial among the employees at Wired.

[Host / Interviewer]

Really? Wow.

[Kevin Kelly]

Right. Because, you know, I was involved with the. Well, going back another time where we were trying to get the. Well, this new conferencing system we made onto the Internet. The Internet was run by the nsf, and it was nonprofit, and they prohibited commercial activity on the Internet. It was prohibited by law, and they were not going to let us connect to it, which we wanted to do, because they were afraid that there would be commercial activity happening on the Internet. Commercial activity? Oh, no, no, no. And a lot of the programmers and hackers who did the coding believe that as well. And we eventually persuaded the NSF to let us become the Internet. And we became the first public access to the Internet in 89 or something. And those same people started to work at Wired in doing the programming. And when Lewis wanted to do advertising.

[Host / Interviewer]

It Was a no for them. Yeah, they didn't get it.

[Kevin Kelly]

Yeah, no, that's going to spoil, ruin, desecrate this beautiful thing that we've made. We're not doing that. And Lewis is saying it's the future of paradise. And we had our own search engine and I believe that if we hadn't broken up there was a good chance that we could have gotten to the ad auction before Google. Wow. That would have been a very different world because we again, we had our own search engine and Google was saying no advertising.

[Host / Interviewer]

Wow.

[Kevin Kelly]

They had no advertising. That's just to say that there was a lot of risk involved. We were lucky sometimes and not lucky others. And the way things were going to play out, nobody could tell, nobody knew.

[Host / Interviewer]

But you have enough certainty to continue and you have enough traction with Wired. What happens in the dot com. Where does that take you?

[Kevin Kelly]

Well, that was part of the reason why it happened. What happened was it started to get very hairy and Wired was being valued. We had a magazine that was making revenue and we had a digital side that had very little revenue. But the digital side was valued at 10x the magazine thing because it was a tech company. And during the crazy bust area, the investors, they took over the board and that was another thing. They took over the board through even though the majority of us owned majority of the stock. There was a takeover, which is hard to explain, but they succeeded and they wanted to sell the company. They panicked and they wanted to sell the digital side. And so they broke up the company and they sold the magazine to Conde Nast and they sold the digital side to Lycos. And so the magazine was prohibited from having a digital side. They gave Wired.com to the digital side and Sy Newhouse at Conde Nast bought Wired. They were investors into the company and it turned out that they were of all the people who could have bought Wired, they were the best because they did the right thing, is they left it in San Francisco and they just left it and they gave a little bit more money for editorial. But I left at that point because I didn't have control of my time. I was not going to fly to.

[Host / Interviewer]

New York and I wanted to take you there because again, sometimes we start from one reason and whether it's a passion or a belief that this is going to work and then just the sheer burnout and the level of being a co founder of something like was. So with the ups and downs that can take you down in a big way, how do you cope as a co founder?

[Kevin Kelly]

That was fine for Me, because I was not doing the business side. That was Lewis and Jane, who were doing all the business. And that was why I hooked up with Louis. Besides him wanting to do a magazine is he had a business savvy business background. He was interested in business. I made it very clear I was not going to do the business stuff. I just wanted to do editorial. And so I isolated myself from some of that craziness. And it was enough just to try and surprise the readers every month. And I did that by asking the writers to surprise me. So I told the writers, look, you're not writing for your grandma, which is what newspapers tell you. You're not writing for the 11th grader. Your audience is me. I read everything and I am totally bored and you have to amaze me in some way. And that's who you're writing to. Because I made the magazines because I wanted to read it. So I am your audience. So we're making a magazine that is going to be surprising.

[Host / Interviewer]

I love that.

[Kevin Kelly]

To me, every month. And so that was enough. And so that's what my focus was. And you know, the IPO stuff and the business and everything, that was Louis, Lewis and Jane. Yeah.

[Host / Interviewer]

We need to pause for a super brief break. And while we do, take a moment and share this episode with every single person who may be inspired by this. Because this information can truly change your life and theirs. Now, every core opportunity you will ever find is most likely from a hidden market. It's the people who think about you when you're not in the room and bring the right opportunities to you. This means that the people you hang out with truly matter. That's why we created our flagship live event in San Jose, California, in the heart of Silicon Valley. It's February 26 to 28 and it's the number one conference for reinvention leadership and careers in the United States. It has speakers like the former president of Starbucks and and many other leaders, including yours truly, myself. And I'd love to personally welcome you, give you a hug, and hear what you think about the podcast. We'll have many networking opportunities, photo opportunities, and we already know every single person after this event will go supersonic on their reputation and career. So grab your tickets quickly because this event always sells out. So go to leapacademy.com leapcon or you can search on Google Leapcon 2026. It's L, E, A P, C O N. Don't miss out. Where the most impactful leaders hang out in February. So go to leapacademy.com leapcon. I will see you there. And so I want to take you a little forward because it's interesting. In Leap Academy, we work with individuals that create what we call portfolio, career, like multiple streams of ventures, income, which we believe is the future of work anyway. But you, back in 2008, if I'm not mistaken, you published a very, very popular piece which is called A Thousand True Fans. And for those who haven't read it, basically you give artists, musicians, writers, any creators, a very clear, achievable path to making a living from their work and their passion. And now we live in this creator mentality. But that was not the case. Again, you were very, very early to see this. What made you create that? What made you write it? And I think based on some of your stories, I can already piece it together. But I would love to hear your think on it.

[Kevin Kelly]

I had been talking about it for a long time before I finally wrote it, but it was prompted in part from one of the guys who followed me at Wired was Chris Anderson, who wrote a piece for Wired and later a book that he expanded, but it was still just a magazine article called the Long Tail. The idea of the Long Tail was that if you aggregate all the sales in that really long tail, outside of the best sellers, that that actually adds up to more than the best sellers, right? The best sellers are the head, those 2% of the head that sell really well. And then you have this long tapering tail of sales that the total of that exceeds the heads. And that was Netflix strategy. That's how Netflix was going to make money, was they were just going to give you that long tail that the other people weren't really interested in. Those were really cheap because nobody really cared about them. They were just. They weren't selling very many. They didn't have a big audience. And Chris and Netflix realized that the total audience back there of the people making, creating things for a small audience, that in aggregate, that was even bigger of a bigger audience than for the bestsellers, the big hits. And I said, well, that's really great for the aggregators, but that's not necessarily any good for the creators. They aren't being aggregated. They're still just selling 10 copies. And so I was trying to figure out what the mathematics or what the curves were for the creators at the tail. And that's when I was kind of running through the arithmetic. And so when I first proposed it, it was a theory. I was saying theoretical, this is what should be possible. But when I went to look for anybody doing it there was very few people, there were a few artists who had been with labels who had gone off the label onto their own and were trying to cultivate a direct audience themselves directly, and they were having some success, but there was only like maybe a handful in total of people who had done that. They were mostly musicians, but that's the theory. And then afterwards, after that time, there were more and more people who either tried it or were trying it. And so we have accumulated huge numbers of people who actually are able to do this, not just in theory, but in practice. And to be explicit to your listeners, the idea is that if you have direct contact with your audience and they are true fans or super fans, meaning that they will buy whatever you produce, the hardcover and the soft cover, every single song, with the CDs and the box sets and the sculpture, plus the sketchbooks. If you have true fans and you can sell them at least $100 worth of merchandise a year or artwork or whatever you want to call it, then that's $100,000, which is kind of a living for most people in the world. It's not a fortune, so you can make a living. And so the thing about that that I ended with and that I would repeat is that first of all, it's not for everybody, it's an option. It's an alternative to having to have a million fans, which you need to have with the studio or publisher label. And so because it's a halftime to full time job, taking care of your fans, interacting with fans is a job and there is a responsibility and you have to do it well. And not every creator is made for that or wants to do that or should be doing it. And creators, as they succeed, may not stay with that. They may decide that they want to. So I would say it's not for everyone, but it's a great place to start. Right?

[Host / Interviewer]

And I will say that I think in today's world, this is getting a different type of meaning, if you will, because it's better to have a thousand fans than 10,000 followers that are just not fans. Because again, the fact that they're gonna like something doesn't mean that they're gonna buy what you have to sell. So for them to actually really love you and be true fans is actually, you know, there's something a lot more meaningful there, right?

[Kevin Kelly]

And there also is, there's a more technical distinction that a lot of the followers are people that you don't have any direct contact with. So the thing about true fan, it's just not that they're supporting you, but that you have direct contact with them. That you sort of what we say, you own the audience. The audience is something that you can take with you, that you can move around, that you have. And part of the challenge on the platforms is that you don't have the audience. And that's something that I originally wrote a piece that went viral called Everything I Know About Self Publishing. And what people don't realize is the New York publishers, they didn't own their customers. Their customers were bookstores, so Random House. They had no direct contact with their readers. They didn't own the readers. They didn't have any. They had bookstores, and the bookstores were just going away. And so that's why when you take a book to a New York publisher, now, the second question after what's the book about? Is, do you have an audience? Can you bring your audience with? Because we don't have an audience. So this idea of having this audience becoming more important as the big labels and studios lose their audiences.

[Host / Interviewer]

And I'm right there on the book stuff with the audience and the publishers. So you're speaking my language right now. Yeah.

[Kevin Kelly]

Right. Right. But you have to have contact with them. You can't just be followers because those aren't.

[Host / Interviewer]

They're not going to buy your book.

[Kevin Kelly]

They're not. Yeah. They're not valuable to. Yeah.

[Host / Interviewer]

So, quick question. Kevin and Phil did. Please tell me that you're not going to talk about it, but somewhere I saw you mention that you should have been dead and that I was like, I need to talk to you a little more about it. What was the experience? Why was it profound? What happened there?

[Kevin Kelly]

This is a story of a conversion experience that had in Jerusalem on Easter morning many, many, many, many, many years ago. And I told that story on one of the earliest episodes of this American Life. And so there was an episode called should have been Dead. And the short story is that the result of this religious conversion experience was that I was given or took on this assignment to live for six months. I mean, to live as if I was going to die in six months. And I took that very seriously. And I did everything that I could to prepare for dying in six months. I was a very healthy young guy who seemed very unlikely, but I did the assignment. And part of that assignment entailed my version of it. I was surprised by what I would do if I had six months. I thought I would do something crazy and risky, climb Everest. But in fact, I wanted to go back and be with my parents. And then I decided to ride my bicycle across the US to visit my brothers and sisters who were kind of scattered. So that three month bike ride became part of this thing of riding to my death. And I tell that story with other aspects of it in this. And one of the things that came out of it was I was giving up all these kinds of things because I really was taking this idea that I wasn't going to live beyond six months and that sort of shrinking future. The idea like every day I had. And so like I didn't take my camera, which after living with my camera and being a camera was so, so hard. I was like, why am I taking pictures? Because what's it for? After six months and other things like that, where I was sort of surrendering the future and I came away from experiencing, realizing that having a future was sort of elemental foundation to human beingness, that you had to have a hope for the future, you had to have something ahead of you that, that was necessary for kind of a full human existence. And so I became much more interested in that sort of forward projection of our lives as necessary for our well being.

[Host / Interviewer]

And to me, the reason why I took you there for a second is because when I read that, and then I read about all the things that you're involved with, like counting all the species and the Long now foundation and all the cool tools that you write about, it almost feels like I need to live every moment all in it.

[Kevin Kelly]

Is because I have a countdown clock right now on my computer. The countdown how many days I have left?

[Host / Interviewer]

But we don't know.

[Kevin Kelly]

Well, we don't know. So I take the actuarial table for someone born my year and I turn that into days.

[Host / Interviewer]

That's very depressing though, Kevin.

[Kevin Kelly]

Oh no, it's not depressing at all. It's very focusing, is very, very focusing. Because I have 5,000, 282 days to do everything that I want to do.

[Host / Interviewer]

I'm panicking just hearing this, Kevin.

[Kevin Kelly]

Every day I'm asking myself with my 5,000 days, do I want to use today to do this? So I would say I have 5,882 days. Do I want to spend some time talking to Elena?

[Host / Interviewer]

Yeah, exactly.

[Kevin Kelly]

And I say yes, yes, yes, that is what I want to do. So I think it's important. The truth is, of course, is that actually, weirdly, the longer you live, the more chance you have of living longer beyond a certain age and with medical advances. And so I haven't lost very much time in the last couple of years.

[Host / Interviewer]

So is that where the optimism comes from? No, you've been optimistic all the time.

[Kevin Kelly]

Longevity is already working in a certain sense. So I haven't been losing as many days as I would have expected. I kind of had this realization from Wired about I asked not just whether I would be good at this thing, whether I would enjoy doing this thing, and whether maybe I could get compensated for the thing. There's a fourth thing right now which I ask about every single opportunity. And that is, could anybody else do this? If somebody else can do this, they should. I don't do it because I only wanted to work on the things that only I can do or only I should do. And that's really, really clarifying. So if I have a book idea, it's like, can anybody else write this book? If I hear about someone else writing a book like it, it's like, I'm not going to do that because they're going to do the book. And so one of the things it does is that when I have an idea, I try to give it away from the very beginning. I try to give it away, my best ideas. And if I can't give that best idea away over multiple tries or years, and I still think it's a good idea, that means, oh, I have to do it.

[Host / Interviewer]

So speaking of a book, because you have multiple, multiple, multiple books now that I'm going through my first book, let me tell you, I don't know how people do this. This is like the slowest thing I've ever gone through. My patience is a bliss. But talk to me. You wrote now a new book, Color of Asia.

[Kevin Kelly]

Colors of Asia.

[Host / Interviewer]

It looks like this is if you're on YouTube. He's showing his book.

[Kevin Kelly]

I'm holding a standard sized book and I'm opening up the pages in the book, which are multiple mosaics of pictures and they're all arranged by color. It's kind of whimsical and fun where we have all the colors and organizing them by color instead of by geography does weird things to your brain. It's like following a color around the street, which is a way for you to notice things that you don't and you associate things that normally are not together. It's kind of like I was in a bookstore and part of the inspiration in San Francisco, Adobe bookstores, and they had an artist take over and he arranged the entire bookstore by color. And it was really cool. Where you had all these books that would normally not touch each other, they were now touching, but it was completely useless at the Same time, because you couldn't find anything but that. Cool and useless is my definition of art. And this is a book that nobody has been clamoring for. There's no demand for a book arranged by color, but I think it's cool and useless. It's art and I think there's a lot of inspiration for designers and it's really cool. It's a different way to travel around color rather than through geography. And so anyway, I did this book. I now have a little shopify place where I'm selling because I'm self publishing it. I decided to self publish one book a year because book publishers don't have audiences anymore. And so this is a lot direct, more faster way. I only printed 1000 for 1000 true fans. So it's a limited edition and they're going fast. I can be found at my initials, kk.org and by the way, that's my email too, kkkid.org which has been public for 35 years. And I hope to make another book next year about something weird that nobody else wants but me.

[Host / Interviewer]

But you bring this amazing love for Asia that I think is just coming through with everything that you do. And I think we feel that love, which is so special.

[Kevin Kelly]

Not only the love, but I've been spending a lot of time in China because most of my audience is in China. It's not in the US My fans are in Asia in China. And I am big in China. And I have a new book out in China two months ago that has no English translation. It's only in Chinese. It's positive scenarios for China in the next 25 years. So I am paying a lot of attention to China. And I think people in the west, and particularly American, underestimate what China is doing. I think we're going to be surprised at least once. Not just that I love Asia and love China, but I'm trying to pay attention, to understand really what's happening there. I just wrote a piece about traveling independently in China, which I suggest everybody go visit China. See for yourself.

[Host / Interviewer]

It is a fascinating place.

[Kevin Kelly]

Yeah, it's very easy to get around even with a language barrier with your app on your phone. And actually I have these new things too, which are really cool.

[Host / Interviewer]

What is that? He's showing us something.

[Kevin Kelly]

I'm holding up the earphones. You put on one here so you.

[Host / Interviewer]

Can put the Google Translate or whatever.

[Kevin Kelly]

Yeah. And I give the other one to the other one and we have a conversation in real time, English to Chinese. That's another way for me to do interviews to get around.

[Host / Interviewer]

By the way, I'm glad you said that because the first time I went there and I couldn't understand anything on the menu and there wasn't Google Translate and I'm like, oh, I don't know what I'm going to eat soon. Like this is like scary.

[Kevin Kelly]

But it's going to be good.

[Host / Interviewer]

It's been a pleasure.

[Kevin Kelly]

I hope I was useful and know that I did enjoy it and I love your spirit. So thank you.

[Host / Interviewer]

It's amazing. Kevin, thanks so much and keep doing crazy things and we're going to keep following and buying your crazy books and we're looking forward to it.

[Kevin Kelly]

Good thing.

[Host / Interviewer]

Remember, this episode is not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or Download button for this show and give it a five star review. This really means the world. Join me in helping tens of millions of individuals reinvent their career and leap into their full potential. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. Aq, adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in life, go to leapacademy. Com Training Check out our completely free training about ways to fast track your career. You'll even be able to book a completely free career strategy call with my team. So go to leapacademy.com training.