Working with Steve Jobs & Becoming a Wiser Guy with Guy Kawasaki, Chief Evangelist at Canva - Modern CTO Recap

Podcast: Modern CTO

Published: 2025-10-02

Duration: 51 min

Summary

In this episode, Guy Kawasaki shares his experiences working with Steve Jobs at Apple and discusses insights from his latest book, Wiser Guy. He reflects on the challenges and privileges of being part of the Macintosh team during a transformative era in technology.

What Happened

Guy Kawasaki, known for his role as Apple's chief evangelist, recounts his time working under Steve Jobs during two pivotal periods at Apple, first from 1983 to 1987 and then returning in 1995. In a memorable meeting, he challenged Jobs by expressing his distrust, which led to a humorous yet costly exchange, costing him potentially $400 million. This anecdote highlights the boldness Kawasaki exhibited, deciding not to back down in the face of Jobs’ formidable presence.

Throughout the conversation, Kawasaki describes Jobs as both an inspiration and a source of fear for those in the Macintosh division. He acknowledges that despite the challenges, working under Jobs drove them to produce some of their best work. The narrative continues with Kawasaki reflecting on his unconventional path to Apple, attributing his hiring to nepotism rather than traditional qualifications, which he humorously contrasts with the expectations of Silicon Valley.

Kawasaki also shares insights about his cultural background, discussing his family's immigration story from Japan to Hawaii, and the legacy of draft dodging that shaped his grandparents' decision to move. He stresses the importance of humor, asserting that a good sense of humor is indicative of intelligence, and connects this belief to his own experiences and the nature of the people he has encountered in his journey.

Key Insights

• The importance of standing up to authority
• The duality of admiration and fear in leadership
• Cultural heritage's impact on personal identity
• Humor as a sign of intelligence

Key Questions Answered

What was it like working under Steve Jobs?

Guy Kawasaki describes working under Steve Jobs as both an honor and a privilege. He notes that Jobs inspired the team to produce their best work, creating an environment that was always exciting, albeit intimidating. Kawasaki emphasizes that anyone who worked in the Macintosh division during that time was afraid of Jobs, and those who claim otherwise are not being truthful.

How did Guy Kawasaki get hired at Apple?

Kawasaki humorously recounts that he got his job in the Macintosh division not through traditional qualifications but through nepotism. His college roommate, who was running the evangelism program at Apple, recommended him. He admits that on paper, he wouldn't have been the ideal candidate, as he majored in psychology and had an MBA in marketing, which he felt was more of a hindrance than a benefit in Silicon Valley.

What cultural background does Guy Kawasaki come from?

Kawasaki shares that he was born and raised in Honolulu, Hawaii, and his family has roots in Japan. His grandparents moved to Hawaii to escape the draft during a war between Japan and China, which shaped their decision to seek a better life. He expresses a strong appreciation for immigration, noting that without it, he might not have had the opportunities he enjoyed.

How does Kawasaki view humor in relation to intelligence?

Kawasaki believes that a sense of humor is a strong indicator of intelligence. He argues that knowing when to laugh and how to use sarcasm and irony reflects a person's ability to understand complex social dynamics. He draws parallels between political leaders and their ability to elicit laughter, suggesting that humor can often be more insightful than serious discourse.

What key lessons does Kawasaki share in his book, Wiser Guy?

In his book, Wiser Guy, Kawasaki aims to impart various insights gained throughout his career, particularly from his experiences at Apple and in the tech industry. The overarching theme revolves around the wisdom acquired from facing challenges and learning from influential figures like Steve Jobs. He discusses the importance of personal growth, resilience, and the value of humor in navigating both personal and professional landscapes.