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

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)

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.

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)

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)

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

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.

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.

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

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

Episode Overview

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)

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)

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

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.

Listen If…

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

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

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Summary

Episode Overview

Key Discussion Points

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

2. Adventures in Asia: The Real University

3. Defining Wealth: Control Over Time

4. Serendipity & Skills: From Budget Travel to Publishing

5. Magazine as a Manifesto: The Birth of Wired

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

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

8. The 1000 True Fans Philosophy

9. Mortality and Focus: Living with a Countdown

10. Art, Asia, and New Adventures

Notable Quotes & Memorable Moments

Timeline of Important Segments

Episode Insights & Takeaways

Listen If…

Summary

Episode Overview

Key Discussion Points

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

2. Adventures in Asia: The Real University

3. Defining Wealth: Control Over Time

4. Serendipity & Skills: From Budget Travel to Publishing

5. Magazine as a Manifesto: The Birth of Wired

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

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

8. The 1000 True Fans Philosophy

9. Mortality and Focus: Living with a Countdown

10. Art, Asia, and New Adventures

Notable Quotes & Memorable Moments

Timeline of Important Segments

Episode Insights & Takeaways

Listen If…