Travis Makes Money — Interview with Guy Kawasaki

Episode Title: Make Money by Playing the Long Game with Reputation, Luck & Leverage
Host: Travis Chappell
Guest: Guy Kawasaki
Date: March 20, 2026

Episode Overview

In this engaging episode, Travis Chappell reconnects with legendary Silicon Valley evangelist Guy Kawasaki. Together, they dive into Guy’s storied tech career—from Apple’s iconic “Think Different” campaign, through his current work with Canva and the “Remarkable People” podcast. They explore themes of reputation, luck, the importance of being adaptable, and the lessons Guy has learned about money, privacy, and career longevity. Guy also shares insights from his latest book, "Everybody Has Something to Hide," and offers practical advice for listeners seeking long-term success with unconventional approaches.

Key Discussion Points & Insights

1. New Book: "Everybody Has Something to Hide"

[01:48–03:45]

• Motivation: Guy explains the inspiration behind his new book—privacy erosion and the societal consequences.
  • “As your privacy degrades, so does society and democracy.” (Guy, 02:13)
  • He praises Signal for secure messaging and expresses a desire to help people be safer online.
• Transparency: Guy emphasizes he’s not gaining financially from this book and has no hidden connection to Signal.
  • “This is my 18th or 19th book, and let's just say Canva has been very good to me, so I don't need to make money.” (Guy, 03:23)

2. The “Think Different” Campaign & Lessons from Apple

[03:45–05:52], [08:38–11:17]

• Inside the Room: Guy recounts being in the room for the famous Apple marketing campaign and how a legendary exchange with Steve Jobs cost him a fortune:
  • “At the end of the showing of the ads, Jay Shayat says, 'Steve, I have two copies... I'll give one to you and one to Guy.' And Steve, as only Steve would do, said, 'Don't give one to Guy.'... I said, 'That's okay Steve, because I don't trust you either.'” (Guy, 04:41)
  • He jokes: “There's Travis Makes Money and there's Guy Loses Money.”
• Apple’s Turnaround: Discusses Apple’s dire straits at the time, Steve Jobs’ return, and how the campaign and iMacs changed Apple’s fortunes.
  • “To use a Macintosh back then, you had to be a rebel. The ad absolutely caught the spirit.” (Guy, 04:52)
  • “It was this ad campaign and the iMacs—and Steve—definitely saved Apple and made Apple come back.” (Guy, 10:30)
• Career Reflection: Guy reflects on leaving Apple twice, missing out on huge potential wealth, and the value of persistence in one’s current role:
  • “Sometimes instead of looking for greener grass, you fertilize and water the grass you’re standing on.” (Guy, 12:19)

3. The Canva Story: Serendipity and Reputation

[13:18–16:59]

• Opportunity by Accident: Guy details how a Twitter mention from Canva founders led to his role as chief evangelist.
  • “That was the due diligence. That was everything. A few weeks later, they were at my house in California and Bada bing, bada bang... here we are 13 years later.” (Guy, 13:39)
• Reputation Matters: Guy credits his visibility from Apple for allowing new opportunities like Canva.
  • “If you do one thing right in your career, you can coast for about forty years... My success with Macintosh enabled Canva to know of me.” (Guy, 15:33)

4. On Luck, Leverage, & Playing the Long Game

[16:59–19:22]

• The Myth of the Golden Touch: Guy debunks the narrative that everything he touches turns to gold, emphasizing the value of resilience:
  • “It's Guy's golden touch? It's whatever is gold, Guy touches—which is a very different philosophy.” (Guy, 17:06)
• Luck & Adaptability: “I'd rather be lucky than smart. Anyway... between those two endpoints, I struck out a lot of times.” (Guy, 13:39; 17:06)
• Strategy: He shares Silicon Valley’s real secret: "We throw a lot of shit up against the wall. One out of 100 sticks. When it does, we paint the bullseye around it and declare victory."

5. Podcasting & Lifelong Learning

[19:42–22:36]

• Passion for Podcasting: Guy describes his “Remarkable People” podcast as his best work, despite being underappreciated:
  • “I think I'm doing the best work of my career on my podcast... I was born and made for podcasting.” (Guy, 20:05)
• Notable Guests: Jane Goodall, Neil DeGrasse Tyson, Margaret Atwood, Tony Fauci, Francis Collins, and more.
• Learning Prevents Cognitive Decline: Hosting a podcast keeps Guy sharp at 71:
  • "52 times a year, I gotta learn something new. I think I am delaying dementia." (Guy, 22:29)

6. Startups: The Two Imperatives—Build or Sell

[24:26–25:58]

• Cutting Through the Noise: Guy shares his classic startup advice:
  • “You're either building stuff or you're selling stuff. Everything else is bullshit.” (Guy, 24:43)
  • Applies this insight to the Apple origin story with Wozniak and Jobs.
• The Three-Legged Stool: For tech startups, ideally add a third “adult supervisor” to balance engineers and salespeople.

7. Pitching, Clarity, and Founder Pitfalls

[22:44–24:17]

• The 10/20/30 Pitch Rule: Origin story of his famous pitch deck concept, born out of suffering through countless bad startup presentations:
  • "Slides...you should show up with ten slides."
• Frustration with Ignored Advice: “People say they love my book... and then it's 60 slides, ten-point font, and they need two hours... How the hell are you showing up with 60 slides?” (Guy, 24:17)

8. Sales: The Real Foundation

[25:58–27:39]

• Respect for Sales: Both agree that sales is at the heart of any organization.
  • "Regardless of what you do, you are in direct benefit of somebody who's picking up the phone and selling somebody something." (Travis, 27:05)
• Overcoming Rejection: Door-to-door sales stories and the relentless pursuit required to succeed.

9. Giving Back & Personal Motivation

[28:04–28:53]

• Moral Obligation: Guy feels a responsibility to give back.
  • “I feel like I've been very fortunate and I have a moral obligation to leave this earth better than I found it.” (Guy, 28:04)
• Free Book Offer: Guy offers a free Kindle copy of his book to listeners—email everybodyhassomethingtohide@gmail.com to receive it.
  • “It ain't about royalty and money anymore. I just want people to preserve their privacy.” (Guy, 28:53)

Notable Quotes

• On Privacy:
  “As your privacy degrades, so does society and democracy.” — Guy Kawasaki (02:13)
• On Career Decisions:
  “Sometimes instead of looking for greener grass, you fertilize and water the grass you’re standing on.” — Guy Kawasaki (12:19)
• On Luck and Reputation:
  “I'd rather be lucky than smart… My success with Macintosh enabled Canva to know of me.” — Guy Kawasaki (13:39; 15:33)
• On Startups:
  “You're either building stuff or you're selling stuff. Everything else is bullshit.” — Guy Kawasaki (24:43)
• On Giving Back:
  “I feel like I've been very fortunate and I have a moral obligation to leave this earth better than I found it.” — Guy Kawasaki (28:04)

Timestamps for Key Segments

• [01:48] — Guy's new book & privacy motivation
• [04:32] — The Think Different campaign story (& $250M missed opportunity)
• [08:38] — Reflections on Jobs, Apple, and transformative campaigns
• [13:18] — How a Canva Twitter mention led to evangelist role
• [15:29] — Evaluating opportunities: due diligence & reputation
• [17:06] — Playing the long game: luck and the myth of “golden touch”
• [20:05] — Podcasting as legacy work
• [22:29] — Lifelong learning and preventing cognitive decline
• [24:43] — Startup essentials: building, selling, and adult supervision
• [28:04] — Giving back: moral obligation and free book offer

Memorable Moments

• Guy’s candid Steve Jobs story: A revealing and humorous insight into the personality dynamics at Apple that also serves as a lesson in corporate trust (and missed financial windfalls).
• Admission of Mistakes: Guy’s transparency about striking out, failing, and not always choosing winners demystifies tech success and encourages resilience.
• Free Book Offer: Concrete generosity—Guy offering his new Kindle book for free to promote privacy, not profit.

Takeaways for Listeners

• Privacy is more relevant than ever, and tools like Signal (and Guy’s book) can help you protect it.
• Sometimes, the best opportunities come from building a strong reputation and staying open to serendipity.
• Success is often about taking calculated shots, being willing to fail, and learning from every attempt.
• In any business or startup, focus on providing real value—through building products and actually selling them.
• Giving back isn’t just a feel-good move—it’s a responsibility for those who’ve found success.

To claim a free copy of Guy’s book on privacy, email:
everybodyhassomethingtohide@gmail.com

For more inspiring stories and practical money-making advice, subscribe to the Travis Makes Money podcast.