September 22, 2025

#175 -Guy Kawasaki - "Wiser Guy" : Apple's Former Chief Evangelist on Mission-Driven Leadership, Surfing at 71, and Where Motivation Comes From

46 minutes

Episode: Built Not Born

Guest: Guy Kawasaki - Former Apple Chief Evangelist, Author of "Wiser Guy"

Host: Joe Ciccarone

Release Date: September 22, 2025

🎯 Power Quote

"Your true scorecard isn't measured in dollars, followers, or fancy titles. It's measured in lives changed, relationships strengthened and personal growth achieved. I hope you made people's lives better. I hope the world is better for you having lived in it." - Guy Kawasaki

📖 Episode Overview

Apple's former Chief Evangelist Guy Kawasaki returns to share wisdom from his new book "Wiser Guy" and reveals the leadership lessons learned from Steve Jobs, the power of saying yes early in your career, and why he started surfing at 60. From getting mistaken for Jackie Chan to learning the high road from his father, Guy delivers actionable insights on motivation, sales mastery, and building a remarkable life.

Key Topics Covered:

Mission-driven leadership vs. being an asshole
The foundation of great teachers and mentors
Why motivation doesn't matter (but being motivated does)
Sales fundamentals and the power of empathy
Punch up, never punch down leadership philosophy
Regret analysis and taking bold action
Learning new skills later in life
Measuring impact over money

⏰ Timestamps with Emojis

🍎 [00:00] - Opening & Steve Jobs "Think Different" Story

Guy recalls being in the room when the iconic "Think Different" campaign was previewed
The moment Steve Jobs said "Don't give one to Guy" in front of everyone
Guy's response: "Steve, it's okay because I don't trust you either"
Why this probably cost him $250 million

👔 [08:15] - Mission-Driven Assholes vs. Regular Assholes

The distinction between people who are assholes for themselves vs. for a mission
Steve Jobs as the ultimate mission-driven asshole
Why Melanie Perkins from Canva proves you don't need to be an asshole to succeed
The chicken-and-egg question: Does being an asshole make you successful, or does success make people tolerate your behavior?

👩‍🏫 [15:30] - The Teacher Who Changed Everything: Trudy Akau

How an elementary school teacher in Hawaii altered Guy's entire life trajectory
The moment she told Guy's parents he had potential and should leave public school
From potential "ghetto guy" to Stanford graduate because of one teacher's intervention
How to become a "Trudy" in someone else's life

🌺 [22:45] - The Gardener Story: Taking the High Road

Getting mistaken for the gardener while trimming his hedge in an affluent SF neighborhood
His father's surprising reaction: "Statistically, she was right"
Why being Japanese American in Hawaii vs. mainland created different perspectives
The lesson in giving people the benefit of the doubt

🏎️ [28:20] - The Jackie Chan Moment

Driving a Porsche, feeling like hot stuff, getting asked by teenage girls if he's Jackie Chan
Guy's life goal: someday having Jackie Chan get asked if he's Guy Kawasaki
Why you've got to get your motivation where you can find it

🚗 [32:10] - What Really Motivated Guy: Cars, Not Changing the World

The Porsche ride in high school that made him want to study harder
Getting robbed twice on the bus and vowing never to live in poverty
The Stanford friend's family with the Rolls Royce, Ferrari, and Arizona Biltmore lifestyle
"Forget changing the world, you gotta change the car"

✅ [40:25] - The Power of Saying Yes Early in Your Career

Why Guy said yes to counting diamonds during MBA school
How seemingly random experiences (jewelry sales) prepared him for Apple evangelism
Learning hand-to-hand combat sales skills
When to transition from saying yes to everything to being selective

🤝 [46:50] - Sales Fundamentals: Empathy Over Everything

The one thing that separates great salespeople from mediocre ones
Why great salespeople think about the customer, not their quota
The importance of believing your product is genuinely good for the other person
Why Guy could never sell Microsoft Windows

👆 [52:15] - Punch Up, Never Punch Down

True strength means challenging those above you, never belittling those with less power
How you can judge someone's character by how they treat "powerless" people
The pragmatic and moral reasons to avoid punching down
Why punching down is a sign of weak ego and overcompensation

😔 [58:30] - Regret Analysis: Action vs. Inaction

Daniel Pink's Regrets Project findings
Why people regret not taking risks more than taking risks and failing
The evolutionary vs. modern context of risk-taking
How social relationships factor into regret patterns

🏄‍♂️ [65:40] - Learning New Skills at 60+: Surfing and Hockey

Started surfing at 60, hockey at 44 (both because his kids were interested)
Why he reverses the typical parent approach - he takes up what his kids love
The mental barriers people create about learning later in life
Still surfing literally every day at 71

🌊 [72:20] - Business Lessons from Surfing

"If you don't try to catch a wave, you'll never catch a wave"
Why waiting for the perfect wave means never catching any wave
The mental complexity of surfing as a metaphor for business decisions
How surfing teaches you when to stop analyzing and just go

👨‍👩‍👧‍👦 [78:45] - Staying Present as a Parent

How his parents modeled being involved and present
The theory of taking up what your kids love instead of making them love what you do
Why he draws the line at wing suiting (his son's hobby)
Being at the game vs. being at the game on your phone

🌍 [85:10] - Measuring Impact Over Money

Keeping score by lives changed, not dollars accumulated
Why Trudy Akau is more remarkable than many famous billionaires
The difference between remarkable people and famous/rich people
Making the world a better place as the ultimate scorecard

💎 [90:25] - Lightning Round

Who he'd spend a day with: Nelson Mandela (dead) or Jane Goodall (alive)
His life mantra: "Empower People"
Why he'd never get a tattoo (sagging skin would distort the font)
What would be on his gravestone: "Empower People"

📚 [95:30] - Closing & What's Next

Hope for readers after "Wiser Guy": learn from every story and experience
Upcoming book: "Signal for Dummies" (December/January)
Where to find Guy: Remarkable People podcast
His guest list: Jane Goodall, Neil deGrasse Tyson, Margaret Atwood, Angela Duckworth

🔥 Key TakeawaysOn Leadership & Character:

Mission-driven vs. ego-driven: Great leaders are assholes for the mission, not for themselves
Punch up, never down: True strength challenges those above, never belittles those below
Give people the benefit of the doubt: Assume positive intent rather than looking for offense

On Career & Success:

Say yes early, be selective later: Accept opportunities when starting out, even if they seem unconventional
Learn from every experience: Diamond counting led to Apple evangelism through sales skills
Motivation source doesn't matter: Whether it's cars or changing the world, just be motivated

On Sales & Influence:

Empathy is everything: Great salespeople think about the customer, not their quota
Believe in your product: You must genuinely think what you're selling helps the other person
Hand-to-hand combat experience: Direct sales teaches skills that translate everywhere

On Personal Growth:

Regret analysis: People regret inaction more than failed action
Learn at any age: Started surfing at 60, still going strong at 71
Reverse parenting: Take up what your kids love instead of forcing them into your interests

On Legacy & Impact:

Measure lives changed, not dollars earned: True scorecard is impact on others
Teachers can change everything: One person believing in you can alter your entire trajectory
Empower people: Simple two-word life philosophy that drives all decisions

📖 Featured Book

"Wiser Guy: Lessons from a Life" - Available everywhere August 18th, 2025

Guy Kawasaki's latest book sharing wisdom from his journey from Hawaii public schools to Silicon Valley legend.

🎧 Previous Guy Kawasaki Episodes

Episode #136: "Steve Jobs, Surfing and the Power of Thinking Remarkable"
This marks Guy's third appearance, tying the record with Seth Godin and Donald Robertson

🔗 Connect with Guy Kawasaki

Podcast: Remarkable People
Book: Wiser Guy (By Guy Kawasaki)
Upcoming: "Signal for Dummies" (December 2025/January 2026)

🏷️ Tags

#GuyKawasaki #JoeCiccarone #Apple #SteveJobs #Leadership #Sales #Entrepreneurship #Surfing #WiserGuy #RemarkablePeople #BuiltNotBorn #Motivation #CareerAdvice #PersonalGrowth #Mentorship #Legacy #Philly

Views expressed by guests do not necessarily reflect the views of the host.

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By Joe Ciccarone

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