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

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 assholeThe foundation of great teachers and mentorsWhy motivation doesn't matter (but being motivated does)Sales fundamentals and the power of empathyPunch up, never punch down leadership philosophyRegret analysis and taking bold actionLearning new skills later in lifeMeasuring 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 previewedThe moment Steve Jobs said "Don't give one to Guy" in front of everyoneGuy'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 missionSteve Jobs as the ultimate mission-driven assholeWhy Melanie Perkins from Canva proves you don't need to be an asshole to succeedThe 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 trajectoryThe moment she told Guy's parents he had potential and should leave public schoolFrom potential "ghetto guy" to Stanford graduate because of one teacher's interventionHow 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 neighborhoodHis father's surprising reaction: "Statistically, she was right"Why being Japanese American in Hawaii vs. mainland created different perspectivesThe lesson in giving people the benefit of the doubt

🏎️ [28:20] - The Jackie Chan...