Wise Guy Summary

"Quitting isn't failing; sometimes it's the start of a transformational journey." This profound idea underpins Guy Kawasaki's incredible life story and the lessons he's eager to share.

1. Roots of Ambition: A Family's Influence

Guy Kawasaki's family history highlights the determination and resilience that shaped his character. His great-grandparents emigrated from Japan to Hawaii in search of a better life during a turbulent time in their homeland.

They made sacrifices to thrive in a foreign land, starting with menial jobs like harvesting sugarcane. Their story instilled in Guy an appreciation for hard work and perseverance. His father, Duke Kawasaki, even became the family's breadwinner at just 14. Music was Duke’s passion, and while he pursued it, he emphasized education as a ticket to greatness.

Guy's parents embodied self-sacrifice to give him the best opportunities. They raised him in Honolulu, in a working-class multicultural environment, and taught him that anything was possible with effort. This mindset laid the foundation for Guy's adventurous spirit and achievements.

Examples

• Guy’s father worked multiple jobs, including leading a band, to support the family.
• His mother, Lucy, narrowly escaped returning to Japan before World War II’s outbreak, ensuring her children grew up in Hawaii.
• The family invested heavily in Guy’s private schooling despite modest incomes.

2. The Power of Teachers and Mentors

Guy’s teachers played key roles in encouraging him to reach higher. Without their intervention, his journey to Stanford—and later, Silicon Valley—might not have occurred.

In sixth grade, teacher Trudy Akau urged his parents to send him to a private prep school. Her belief in his potential led him to ‘Iolani School, despite the financial burden on his family. Later, Dan Feldhaus, a counselor at ‘Iolani, saw through Guy’s average grades and encouraged him to apply to Stanford.

This guidance paid off when Guy gained admission to one of the most prestigious universities in the United States. These mentors saw something in him that numbers couldn’t quantify—a lesson about looking beyond statistics to find potential in people.

Examples

• Trudy Akau’s call pushed Guy’s family to prioritize private schooling.
• Dan Feldhaus highlighted Stanford as a possibility, even with Guy’s below-average GPA.
• His Stanford experience introduced him to friends who guided his path, including a future Apple connection.

3. Quitting Can Be Liberating

Quitting doesn’t mean failure; it can be an act of courage. Guy learned this firsthand when he left law school after just one week.

Despite societal and parental expectations for careers like law or medicine, Guy realized early on that neither path suited him. His decision to quit law school might have disappointed his family, but they supported him. Their only advice: Make something of your life by 25.

This experience led Guy to an MBA program and eventually to the jewelry trade, which shaped his talent for sales. This pivotal moment shows how stepping away from what’s “expected” can open doors to meaningful life directions.

Examples

• Guy’s quick exit from University of California, Davis, law school.
• Support from his parents despite initial fears of disappointing them.
• Learning traditional salesmanship in the jewelry trade set him up for evangelizing Apple products.

4. Breaking into Apple Through a Friend

Guy’s Silicon Valley story began not through formal job applications but via a recommendation from a friend, Mike Boich. His entry into the tech world underscores the power of connections.

Despite lacking a background in tech, Guy’s sales ability impressed Apple's team. Hired as a "software evangelist," his job involved promoting Macintosh computers to software developers and users—a role that demanded his innovative and people-focused skills.

Guy’s journey at Apple, including securing developers for an untested product, wasn’t easy. His career there thrived thanks to determination and building rapport. His break at Apple proves that sometimes connections matter more than paper qualifications.

Examples

• Mike Boich vouched for him despite his non-technical background.
• Guy’s pitch focused on showing how Apple would innovate, not on its flaws.
• The Apple II word processor initially hooked Guy himself as a fan.

5. Facing Setbacks with Grace

Guy’s tenure at Apple wasn’t without frustration. He recounts the moment when his chances for promotion were blocked, teaching him lessons about humility and resilience.

His boss, Del Yocam, decided against promoting Guy, citing friction with major companies like Microsoft. Though Guy initially thought burning bridges with competitors helped Apple, he later realized that forming strategic partnerships mattered.

These disagreements led him to venture into entrepreneurship. Ultimately, his decision to leave Apple and co-found ACIUS marked a bold new chapter, leading to the database software "4th Dimension," an enduring product.

Examples

• Del Yocam’s rejection pushed Guy to reevaluate corporate dynamics.
• Guy and two collaborators developed "4th Dimension" after leaving Apple.
• ACIUS became a successful independent software company despite early challenges.

6. Returning to Apple for the Love of the Brand

In 1995, as Apple teetered on the brink of failure, Guy returned to help. His mission was to maintain its image and engage loyal Mac users during turbulent times.

To achieve this, he created EvangeList, an opt-in community that shared optimistic Apple stories and updates. This group was small but significant in preventing customer attrition at a time when the tech giant was struggling to compete with Windows PCs.

Guy’s efforts during this period reflect his belief in loyalty—not just from customers but to the brands and values one holds dear.

Examples

• The EvangeList mailing list built morale among remaining Mac fans.
• Steve Jobs’ 1997 return brought fresh ideas, including the colorful iMac.
• The user group engagement model drove lasting customer trust for Apple.

7. Family Comes First

Guy places family achievements above all else. Parenting, he says, taught him more about empathy and vulnerability than any mentor or career path.

Through his son Nate’s dyslexia, Guy learned to see the world through different perspectives—a transformative experience. His children also held mirrors to his own flaws, such as when his daughter’s honesty challenged his pride in surfing.

These lessons shaped Guy’s approach to relationships, showing how parenting enriches self-awareness and patience.

Examples

• Nate’s dyslexia made Guy reevaluate his expectations.
• His daughter’s critique taught him humility in pursuing surfing.
• Recalling his curt remark to his father reinforced the importance of kindness.

8. It’s Never Too Late to Try Something New

Learning to surf at age 62 taught Guy one valuable truth: Age is no limit when it comes to pursuing passions.

Guy struggled with surfing, repeatedly failing to master the waves. But persistence, alongside guidance from expert Jeff Clark, helped him improve. He even created his own path by using a paddleboard instead of standard boards.

His surfing journey is a microcosm of his life philosophy: effort, adaptability, and humor go a long way, even when the odds seem stacked against you.

Examples

• Struggling to match his daughter’s surfing talents initially.
• Jeff Clark’s mentorship propelled him forward.
• His unique use of a paddleboard showcased creativity in problem-solving.

9. Building Networks Over Job Applications

Throughout his career, Guy emphasizes that relationships opened almost all of his professional doors, from his early jobs to his Apple tenure and beyond.

Instead of submitting countless résumés, fostering relationships maximized his opportunities. Friends, mentors, and even chance acquaintances became his career allies.

This point carries a universal takeaway: Success often comes down to the people you invest time in, and the connections you nurture.

Examples

• Mike Boich’s recommendation built his tech career.
• Guy’s parents’ support secured his education despite financial struggles.
• Dan Feldhaus’ guidance gave him the confidence to aim high.

Takeaways

1. Build strong relationships: Invest time and effort into your network. These connections may have a larger impact on your future than formal credentials.
2. Embrace unconventional paths: Don't fear quitting or switching gears if something feels wrong—it could lead you to a better-suited opportunity.
3. Pursue lifelong learning: Whether it's a new skill or hobby, don't let age—or fear of failure—stop you from starting something worthwhile.