Modern CTO Working with Steve Jobs & Becoming a Wiser Guy with Guy Kawasaki, Chief Evangelist at Canva
Oct 2, 2025
In this engaging conversation, Guy Kawasaki, Chief Evangelist at Canva and former Apple evangelist, shares his unique experiences with Steve Jobs, who he describes as both inspiring and terrifying. He humorously recounts their infamous trust exchange and reflects on how his hearing loss shaped his perspective on life. Guy discusses the importance of humor in leadership and his mission-driven approach at Canva. He also touches on personal growth, his late-life surfing adventures, and the lessons outlined in his book, 'Wiser Guy'.
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Nepotism Led To Macintosh
- Guy joined Apple's Macintosh division through his college roommate, acknowledging nepotism.
- He notes his academic background (psychology, MBA) on paper wouldn't have been the obvious hire, but the fit worked out.
Confronting Steve Jobs
- Guy Kawasaki recounts telling Steve Jobs "I don't trust you either" during a Think Different ad meeting.
- He jokes the confrontation cost him about $400 million but frames it as a memorable, character-defining moment.
Living With Hearing Loss
- Guy reveals he is deaf and uses a cochlear implant, which improved his hearing from none to "lousy hearing."
- He shares struggles interviewing complex guests using live transcription and plans another implant for the second ear.
