Wise Guy

Introduction

Guy Kawasaki's "Wise Guy" is an engaging memoir that offers valuable life lessons from a true Silicon Valley pioneer. As one of the original Apple employees who helped launch the Macintosh, Kawasaki has had a front-row seat to the tech revolution. But this book is about much more than just his professional accomplishments. It's a deeply personal account of his upbringing, relationships, challenges, and the wisdom he's gained along the way.

Born to Japanese-American parents in Hawaii, Kawasaki's story is one of seizing opportunities, taking risks, and constantly reinventing himself. From his early days selling jewelry to becoming Apple's chief evangelist to learning to surf in his 60s, Kawasaki's life has been defined by bold moves and a willingness to try new things. Throughout the book, he reflects on the mentors, friends, and family members who shaped him, offering heartfelt tributes to those who believed in him and pushed him to reach his potential.

What makes "Wise Guy" stand out is Kawasaki's honesty and humility. He's quick to acknowledge his mistakes and shortcomings, using them as teachable moments. The book is filled with practical advice on everything from public speaking to parenting, all delivered in Kawasaki's trademark straightforward style. It's clear that his goal is not just to recount his own story, but to inspire readers to live their best lives and make a positive impact on the world.

Let's dive into the key lessons and memorable stories from this Silicon Valley sage.

A Family of Dreamers

Kawasaki's journey begins with the story of his family's immigration to America. His great-grandparents left Hiroshima, Japan between 1890 and 1900, seeking better opportunities in Hawaii. They were part of a wave of Japanese immigrants who came to work on sugar plantations, earning just $1 a day. While the work was hard, it offered an escape from the increasing militarization of Japan at the time.

The Kawasaki family settled in Honolulu, where Guy's father Duke was born. Duke's early life was marked by tragedy when his mother Alma died during childbirth. At just 14, Duke became the family breadwinner. Despite limited formal education, he developed a passion for music, learning to play multiple instruments and even befriending famous bandleader Guy Lombardo (after whom the author was named).

On his mother's side, Kawasaki's grandparents were also Japanese immigrants to Hawaii. His mother Lucy had a unique experience, being sent to school in Yokohama, Japan in 1939. She returned to Hawaii on one of the last ships to leave before the attack on Pearl Harbor in 1941.

Guy and his sister Jean were raised in a multicultural, working-class neighborhood in Honolulu. His parents worked tirelessly to provide for their children and instilled in them the belief that anything was possible with hard work and determination. This immigrant work ethic and optimism would shape Kawasaki's approach to life and become a cornerstone of his success.

The Power of Mentorship

One of the recurring themes in "Wise Guy" is the impact of mentors and teachers who saw Kawasaki's potential and pushed him to excel. Two educators, in particular, played pivotal roles in setting him on the path to success.

In sixth grade, Kawasaki's teacher Trudy Akau recognized his abilities and convinced his parents to apply to prestigious private schools in Honolulu. This led to Kawasaki's acceptance at 'Iolani School, a college preparatory institution that would dramatically alter the course of his life.

The annual tuition of $1,250 (equivalent to about $8,000 today) was a significant financial burden for Kawasaki's parents, who were making around $20,000 a year. But they believed in the value of education and made sacrifices to afford it. Kawasaki credits this decision as the first step on his path to Stanford University and his eventual career in Silicon Valley.

However, Kawasaki's academic performance at 'Iolani wasn't stellar. His GPA was just 3.4, and his SAT scores were unremarkable. It was his college counselor, Dan Feldhaus, who saw beyond the numbers and encouraged Kawasaki to aim high. Feldhaus convinced him to apply to Stanford, believing in Kawasaki's potential despite his middling grades.

To Kawasaki's surprise, he was accepted to Stanford, along with the University of Hawaii and Occidental College. While he was initially drawn to Occidental for its strong football program, his father insisted he attend Stanford for its academic reputation. This stern guidance from his father proved to be another crucial turning point in Kawasaki's life.

The lesson here is clear: sometimes others can see our potential more clearly than we can ourselves. Kawasaki's story is a testament to the power of mentorship and the importance of having people in our lives who believe in us and push us to reach higher.

The Courage to Quit

One of the most valuable lessons Kawasaki shares is that quitting isn't always synonymous with failure. Sometimes, it's a necessary step toward finding your true path.

After graduating from Stanford in 1976, Kawasaki followed the expected route for many Asian-American students at the time: he enrolled in law school at the University of California, Davis. However, he quickly realized that law wasn't for him. The confrontational teaching style and the prospect of a career he wasn't passionate about led him to make a bold decision: he quit after just one week.

This decision was terrifying, particularly because of the potential disappointment it might cause his parents. To his surprise, they were understanding, telling him that as long as he made something of himself by age 25, everything would be fine.

This experience taught Kawasaki an important lesson: it's okay to change course when something isn't working. Quitting law school wasn't a failure; it was a necessary step in finding his true calling.

After leaving law school, Kawasaki enrolled in an MBA program at UCLA. It was here that he stumbled upon an opportunity that would prove invaluable: working part-time in the jewelry business. This experience, which might have seemed unrelated to his studies, actually provided him with crucial sales skills that would serve him well in his future career at Apple.

The jewelry business taught Kawasaki the art of old-school bargaining and salesmanship. He learned how to convince skeptical buyers and close deals under pressure. These skills would prove instrumental when he later had to convince software developers to create products for the then-unproven Macintosh platform.

Kawasaki's journey from law school dropout to jewelry salesman to tech evangelist illustrates an important point: our paths are rarely linear, and what might seem like a detour can often provide us with unexpected skills and experiences that prove valuable later on.

The Lucky Break at Apple

Kawasaki's entry into the world of technology came through a combination of luck, connections, and being in the right place at the right time. His Stanford friend Mike Boich introduced him to the Apple II computer, which Kawasaki found revolutionary compared to the typewriters he'd been using.

When Boich later told him about an opening at Apple, Kawasaki jumped at the chance. In September 1983, he joined the Macintosh Division as a "software evangelist." This role involved convincing software and hardware manufacturers to create products compatible with the yet-to-be-released Macintosh computer.

Kawasaki readily admits that he wasn't the most qualified candidate on paper. His background in psychology and business, along with his experience in jewelry sales, didn't seem directly relevant to the tech industry. Even Steve Jobs was skeptical, telling Boich that he was staking his own career on the decision to hire Kawasaki.

However, Kawasaki quickly proved his worth. His years of experience in jewelry sales turned out to be surprisingly relevant to his new role. The job of a "software evangelist" was essentially a sales position, requiring him to convince skeptical companies to take a chance on an unproven product. Kawasaki's ability to build relationships, communicate effectively, and close deals made him an ideal fit for the role.

Kawasaki attributes his success at Apple to several factors. First, the innovative nature of Apple's products created a natural buzz that helped draw people in. Second, the timing was perfect, as personal computers were just starting to take off in the mid-1980s. But most importantly, Kawasaki loved the work, and his passion and enthusiasm were contagious.

This experience taught Kawasaki several important lessons:

1. Sometimes, unconventional experience can be your greatest asset.
2. Passion and determination can often outweigh technical qualifications.
3. Being in the right place at the right time is important, but you need to be prepared to seize opportunities when they arise.
4. The ability to build relationships and communicate effectively is crucial in any field.

Kawasaki's lucky break at Apple set the stage for his future success, but it was his hard work and adaptability that allowed him to make the most of the opportunity.

Navigating Corporate Politics

Kawasaki's time at Apple wasn't always smooth sailing. His experiences there taught him valuable lessons about corporate politics and the importance of understanding the bigger picture.

By 1986, Kawasaki had been with Apple for three years and was up for a promotion. This would have included a seat on the board of directors, a raise, stock options, and a company car. However, his superior, Chief Operating Officer Del Yocam, opposed the promotion.

The reason? While Kawasaki had excellent relationships with smaller companies, three major software companies - Microsoft, Lotus, and Ashton-Tate - disliked him. Kawasaki initially saw this as a badge of honor, believing it was his job to challenge these competitors. However, Yocam understood that Apple needed alliances with these larger companies to succeed.

At the time, Kawasaki was furious about the decision and nearly quit. Looking back, however, he believes Yocam made the right call. This experience taught him the importance of seeing beyond his immediate role and understanding the broader strategic needs of the company.

The situation with Ashton-Tate further illustrated the complexities of corporate decision-making. Apple needed a relational database to make the Macintosh viable for business use. When French developers created a promising database called 4th Dimension, Apple initially moved to acquire it. However, they backed out of the deal under pressure from Ashton-Tate, who didn't want competition for their own product.

This decision alienated Kawasaki, along with the French developers. In response, they decided to publish 4th Dimension independently. On April 1, 1987, Kawasaki left Apple to become the CEO of ACIUS, the company behind 4th Dimension.

These experiences taught Kawasaki several important lessons about navigating corporate environments:

1. Sometimes, what seems unfair in the moment may make strategic sense for the company.
2. It's important to understand the bigger picture and how your role fits into the company's overall strategy.
3. Corporate decisions often involve complex trade-offs and competing interests.
4. Setbacks can sometimes lead to new opportunities if you're willing to take risks.

The Return to Apple

In 1995, Apple was facing a crisis. Steve Jobs had left a decade earlier, the Macintosh was struggling in the market, and the company was hemorrhaging money and employees. In this dire situation, Apple's vice president Dan Eilers reached out to Kawasaki, asking him to return as chief evangelist.

Despite the company's troubles, Kawasaki's love for Apple had never faded. He accepted the position, tasked with preserving the Macintosh brand image and retaining its loyal user base. This was a perfect fit for Kawasaki, who had spent years building relationships with Mac user groups during his first stint at the company.

To bolster the spirits of Apple's dedicated fans, Kawasaki created EvangeList, an opt-in email list featuring positive news about Apple and Mac, along with product announcements from developers. The list grew to over 40,000 subscribers - a significant number for the time. EvangeList played a crucial role in keeping the Apple community engaged and loyal during the company's darkest hours.

Kawasaki's efforts helped keep Apple afloat, but the real turning point came with Steve Jobs' return to the company in 1997. Jobs streamlined the product line and introduced the colorful, all-in-one iMac. Kawasaki notes that only a visionary like Jobs could convince the world that repackaging a computer in eye-catching colors was revolutionary.

This experience taught Kawasaki several important lessons:

1. Loyalty and passion for a brand can be powerful motivators, even in difficult times.
2. Communication and community-building are crucial for maintaining customer loyalty.
3. Sometimes, returning to a previous role or company can provide new opportunities and challenges.
4. Visionary leadership can transform a struggling company.

Kawasaki's second stint at Apple reinforced his admiration for Jobs' leadership style and vision, which would continue to inspire his own approach to business in the years to come.

The Joys and Challenges of Parenthood

Despite his professional accomplishments, Kawasaki considers his family to be his greatest achievement. He met his wife Beth, a fellow Apple employee, in 1983, and together they've raised a family that has taught Kawasaki invaluable lessons about empathy, kindness, and self-reflection.

One of the most profound lessons came through his son Nate, who has dyslexia. Initially, Kawasaki and his wife were frustrated by Nate's struggles in school. However, their perspective changed dramatically after attending a parent-teacher evening where they participated in an exercise simulating the experience of dyslexia. Unable to complete even a single task, Kawasaki broke down in tears, finally understanding the challenges his son faced every day.

This experience taught Kawasaki the importance of empathy and the danger of judging others without truly understanding their circumstances. It's a lesson he's carried with him in all aspects of his life, reminding him to approach people and situations with compassion and an open mind.

Parenting also taught Kawasaki about self-reflection and personal growth. When his daughter Nohemi bluntly told him he was bad at reading waves while surfing, it stung - not just because of the criticism, but because it reminded him of a similar comment he had made to his own father years ago about his piano playing. This full-circle moment made Kawasaki reflect on the impact of his words and actions, teaching him to be more mindful and respectful in his interactions with others.

Kawasaki shares several key insights about parenting:

1. Children can be our greatest teachers, offering lessons in empathy, patience, and self-awareness.
2. It's crucial to try to understand the world from your child's perspective.
3. Our words and actions as parents can have a lasting impact, for better or worse.
4. Parenting often involves facing our own shortcomings and working to improve ourselves.

Learning to Surf at 62

One of the most inspiring stories in "Wise Guy" is Kawasaki's decision to take up surfing at the age of 62. This adventure not only helped him bond with his daughter but also taught him valuable lessons about perseverance, adaptability, and the importance of continuing to learn and grow at any age.

Kawasaki started with paddle surfing, which involves standing on the board and using a paddle for balance and propulsion. He was making good progress when his daughter Nohemi developed a passion for prone surfing - the more traditional style where the surfer lies on the board and then stands up to ride the wave.

Wanting to share in his daughter's hobby, Kawasaki decided to try prone surfing as well. It was a humbling experience. His attempts were often clumsy and provided amusement for onlookers. However, Kawasaki persevered, even seeking guidance from Jeff Clark, a legendary surfer known for conquering the massive waves at Mavericks.

What ultimately helped Kawasaki succeed was his willingness to think outside the box. He repurposed his old paddleboard as a prone board, despite this being considered unconventional by surfing standards. While professionals might have scoffed at this approach, it worked for Kawasaki, allowing him to finally catch and ride waves.

This experience reinforced several important life lessons for Kawasaki:

1. It's never too late to learn new skills or pursue new passions.
2. Natural talent is overrated - dedication and practice are what truly matter.
3. Don't be afraid to take an unconventional approach if it works for you.
4. Seeking guidance from experts can accelerate your learning and growth.
5. Sharing in your children's interests can strengthen your bond and open up new experiences.

Kawasaki's surfing journey is a powerful reminder that personal growth doesn't have an expiration date. By maintaining a curious and open mindset, we can continue to challenge ourselves and find joy in new experiences throughout our lives.

The Power of Connections

Throughout "Wise Guy," Kawasaki emphasizes the importance of building and maintaining connections. His own career trajectory is a testament to the power of networking and relationships.

Kawasaki reveals that out of the 15 positions listed on his resume - ranging from his first job as a truck driver's helper in 1971 to his current role as a brand ambassador for Mercedes-Benz - only one came from responding to a job advertisement. The rest were the result of connections he had built over the years.

This insight leads to one of Kawasaki's most actionable pieces of advice: focus on fostering connections rather than simply submitting job applications. He suggests that most people already have a network of potential contacts in their heads - family members, friends, acquaintances, former colleagues. The key is to actively nurture these relationships and not be afraid to reach out when opportunities arise.

Kawasaki's own career provides numerous examples of this principle in action:

1. His first job at Apple came through his Stanford friend Mike Boich.
2. His return to Apple in 1995 was due to his ongoing relationship with the company and its employees.
3. Many of his post-Apple ventures and speaking engagements came through connections he had built in the tech industry.

However, Kawasaki is quick to point out that networking isn't about using people or maintaining superficial relationships. Instead, it's about building genuine connections, being willing to help others, and creating a community of mutual support and opportunity.

He offers several tips for effective networking:

1. Be genuine in your interactions. People can sense insincerity.
2. Offer value before asking for favors. Look for ways to help others in your network.
3. Stay in touch regularly, not just when you need something.
4. Be open to connecting people in your network with each other.
5. Express gratitude when others help you.

Kawasaki's emphasis on connections underscores a fundamental truth about career success: it's not just what you know, but who you know - and more importantly, who knows you and what you're capable of.

Final Thoughts: Embracing Life's Lessons

As "Wise Guy" draws to a close, Kawasaki reflects on the overarching lessons he's learned throughout his journey. His story is one of continuous growth, adaptability, and a willingness to learn from both successes and failures.

One of the key takeaways is the importance of seizing opportunities. From his parents' decision to send him to a prestigious private school to his own choice to join a fledgling Apple Computer, Kawasaki's life has been shaped by moments when he or others recognized and acted on potential. He encourages readers to be open to new experiences and to have the courage to take calculated risks.

Another crucial lesson is the value of perseverance. Whether it was struggling through his early days at Apple, navigating the challenges of parenting, or learning to surf in his 60s, Kawasaki demonstrates that success often comes from refusing to give up, even when things get difficult.

Kawasaki also emphasizes the importance of continuous learning. His career has spanned multiple industries and roles, requiring him to constantly acquire new skills and knowledge. This adaptability has been key to his success and longevity in the fast-paced world of technology and business.

Throughout the book, Kawasaki's humility shines through. He's quick to credit the mentors, friends, and family members who have supported him along the way. This gratitude serves as a reminder of the importance of acknowledging those who help us and paying it forward when we can.

Finally, Kawasaki's story underscores the importance of passion. Whether it's evangelizing for Apple products, building relationships with customers, or pursuing personal interests like surfing, Kawasaki's enthusiasm is a driving force in his life. He encourages readers to find work and pursuits that genuinely excite them, arguing that this passion is often the differentiator between mediocrity and excellence.

In conclusion, "Wise Guy" is more than just a memoir. It's a guidebook for living a fulfilling life, filled with practical advice and inspiring stories. Kawasaki's journey from a working-class kid in Hawaii to a Silicon Valley icon is a testament to the power of hard work, continuous learning, and the courage to seize opportunities. His story reminds us that with determination, adaptability, and a willingness to learn from both our successes and our failures, we can all strive to live our best lives and make a positive impact on the world around us.