Wise Guy

Do you remember that Listerine ad called “The Bold Type?” This commercial pitched its mouthwash by claiming that people who used Listerine were more inclined to be bold, confident, and successful. “The Bold Type” of people, they argued, were those who were likely to take risks, engage in food fights, or to get messy, get creative, and be happy about it! By extension, they suggested that if you used Listerine, you too would be willing to dance spontaneously, talk your way into a VIP area, do cartwheels, or try new things. But they could have just saved time by showing a picture of Guy Kawasaki. That’s because Kawasaki is the very definition of “The Bold Type.”

His willingness to explore new challenges and be spontaneous has led him to take up surfing at the age of 62, take on a job he wasn’t qualified for (and succeed!), and drop out of law school, among other things! This book documents his life and the philosophy that brought him success, along with the quirky anecdotes which have prompted him to label himself a “wise Guy.” (Get it?)

No matter what our lives are like growing up, they shape us for better or worse. Whether we learn that we never want to be like our parents or we hope to emulate their example, our families pass on vital life lessons which mold the people we become. And the same is true for Kawasaki, whose great-grandparents — on both his mother and father’s side! — emigrated to Hawaii from Japan in 1890. Kawasaki’s parents, therefore, were born in Hawaii and raised as American citizens and thus, so was he. But the legacy of his great-grandparents’ dream became an integral part of their family identity.

None of them had had it easy; for example, his father Duke had to step up and become the primary provider for his family at the age of 14. As a result, his education was minimal at best, but he did secure the opportunity to study — briefly — at the Berklee College of Music in Boston! There, he founded a band called Duke Kawa’s and honed his musical talent by learning to play the flute, clarinet, and saxophone. That’s also where he met the Canadian bandleader Guy Lombardo, and their friendship was so memorable that he treasured the name Guy for many years to come, ultimately bestowing it on his only son.

As a result of these life experiences, the family culture into which the author was born was characterized by the values of hard work and dreaming. And by telling him the story of his parents, grandparents, and great-grandparents, the author’s family taught him that anything was possible if he dreamed big, refused to give up, and made the most of every opportunity life offered him. And these values have informed the author’s worldview to this day.

As we discussed in the previous chapter, Guy’s parents and grandparents had worked hard to make a life for themselves in America. Everything they had, they had earned through years of sacrifice and hard work. Unfortunately, however, this meant that they had been unable to pursue a quality education. And as a result, it was vitally important to them that Guy and his sister Jean receive the best. Guy internalized this family value as well and applied his best efforts in his education. This allowed his natural aptitude for academics to shine and therefore, it was no surprise when his sixth-grade teacher, Trudy Akau, called his parents to tell them Guy was gifted. As a result, she suggested that he would benefit from a more advanced environment, one that could prepare him for superior academics and success in college.

So, with Miss Akau’s glowing letters of recommendation, Guy applied to Honolulu’s two premier prep schools, Punahou and ‘Iolani. (Fun fact: former president Barack Obama was a graduate of his first choice, Punahou!) When Guy was accepted by ‘Iolani, however, the momentous success was bittersweet: although there was no question that Guy would receive a superior education and be well-prepared for the future, the opportunity came with a hefty price tag. With tuition costs of $1,250 a year, this was an almost crippling cost for Guy’s parents, whose combined yearly income amassed a mere total of $20,000. But because they were determined for their son to succeed, the Kawasakis made even more sacrifices and somehow came up with the money.

It turned out to be one of the best decisions they ever made. Because not only did ‘Iolani prepare Guy for success, it opened the door for him to make connections with his dream school, Stanford University. However, despite his private prep-school education and his natural aptitude, Guy wasn’t necessarily a shoe-in for Stanford. Like many gifted kids, he felt torn between the pressure to devote himself to academics and fit in with the real world. As a result, this conflict often caused him to neglect his studies or at least fail to apply himself fully. So, by the time Guy graduated from ‘Iolani, his GPA was a mere 3,4. To give you an idea of how Guy’s grades lined up with Stanford’s admissions requirements, their minimum GPA for undergrad acceptance is 3.96. This requires applicants to be at the top of their class and Guy certainly was not.

Because of this discrepancy, it’s possible that he might never have even been considered for admission if it weren’t for the influence of his college counselor, Dan Feldhaus. Feldhaus, himself a brilliant mathematician, recognized that Guy had potential which transcended his grades. If he could just apply himself in the rightenvironment, with access to the right resources, Feldhaus knew that his student could achieve great things.

So, thanks to another glowing recommendation from a teacher who believed in him, Guy Kawasaki was accepted to Stanford in 1972. Looking back, the author laughingly reflects that if it had been up to him, he would have made a different call. Once again torn between the desire to excel or have fun, Guy was leaning toward accepting an offer from California’s Occidental College with aims of playing on their football team.

Fortunately, however, his father put his foot down, asserting that he didn’t work and sacrifice for Guy to play a sport instead of receiving an education. With his father’s support (and insistence), Guy accepted Stanford’s offer and majored in psychology. And today he knows, beyond the shadow of a doubt, that this was the right decision.

We often have a lot of stereotypes about the children of immigrants and the careers their parents expect of them. We assume, for example, that many Asian children are expected to become doctors or lawyers because these careers are widely regarded as being lucrative and successful. And the author acknowledges that — unlike most stereotypes — in this case, your assumptions are absolutely correct. Because his parents had worked hard and sacrificed to give Guy a shot at a successful future, they expected him to pursue a career that would tick both those boxes, even if it didn’t necessarily align with his interests.

So, after graduating Stanford with a degree in psychology in 1976, Guy decided that he wasn’t cut out to be a doctor or a dentist; careers that involved getting up close and personal with gross bodily fluids weren’t for him. That meant law was the only acceptable remaining option. So, immediately after he graduated with his BA, he applied for law school at the University of California, Davis and started his first semester that fall. Unfortunately, however, his law school experience immediately got off on the wrong foot.

On his very first day in orientation, Guy — along with the entire freshman class — sat in horror as the law professor told them all that they were ignorant. They didn’t deserve to be here. They would amount to nothing. That’s how Guy learned that this was UCD’s version of a pep talk. And maybe it would have inspired another student, motivated them to prove the teacher wrong, but it just made Guy angry. His frustration grew as his first week of classes employed the same style of “motivation.” Public humiliation was the most popular teaching tool, with hard-working students beingbullied by professors in front of the entire class. Attempts to learn and ask questions were mocked. Students were regularly berated without cause. And after a week of this, Guy knew that he couldn’t spend the next three years of his life here.

So, despite his fear of disappointing his parents, Guy dropped out of law school. As he packed up his dorm room and drove home, a million frightening questions raced through his head. What would his parents say when he told them? What if they never spoke to him again? What if they thought he had rejected their sacrifice? What if they were disappointed in him? Much to his surprise, however, none of his worst fears came true. His parents understood that that environment wasn’t conducive to learning and they didn’t want him to be miserable. They helped him understand that even if he had technically “failed” at law school, he was still a success because he had done the right thing. However, they still wanted him to pursue a successful career of some sort. And they still expected him to accomplish something big by the time he turned 25. That might sound like a tall order, but Guy — being the bold type — was ready to take on the challenge.

People often say that college is the best time of your life. Whether that’s because of the education you receive, the friendships you make, or the freedom of making your own decisions without the pressure of adult responsibilities, for most people, that’s true. In Guy’s case, however, the most beneficial part of his college education was the connections he made along the way. Because without the friendships he formed at Stanford, the Guy Kawasaki we know today would probably never have existed. And that’s because his Stanford buddy, Mike Boich, introduced him to Apple. Boich got in on the tech scene early and shared his love of computers with Guy.

And after Guy fell in love with the Apple II PC, Boich was the one who encouraged him to pursue his new passion for technology by pursuing a job opportunity with Apple. So, in September 1983, Guy became a “software evangelist” for Apple. In these days, “software evangelist” was code for what we now refer to as a “brand ambassador.” And although it’s pretty easy to become a brand ambassador today — Instagram ads for influencers abound! — in the ‘80s, it was a pretty big deal. In fact, it was such a big deal that Boich went to bat for Guy’s job himself, even going so far as to schedule an interview with Steve Jobs himself to convince him! And it wasn’t an easy sell. Because Guy had no qualifications or experience which prepared him for this position, Jobs expected him to fail. So, he told Boich that yes, he would hire Guy… but if he failed at the position, Boich would lose his job, too!

That might sound like an overwhelming amount of pressure, but having grown up with parents who expected him to be a success by 25 and who impressed the values of taking risks and persevering, Guy was prepared for the challenge. He quickly learned that to be successful as a brand ambassador, he had to sell customers on a vision. This was crucial because, at the time, Apple was more of a concept than a real business. It might have had a few products ready to hit the market, but it was mostly unfinished code and prototypes. So rather than convincing customers to believe in the success of what they had created, Guy had to inspire them to believe in something they couldn’t see. But after only six months of working with Apple, Guy was attracting customers like flies to honey. When Jobs asked about his secret for success, Guy said only that he’d realized selling customers was all about learning what they wanted.

Their customer base was comprised of techies who were looking for the next big wave of technological advances. And because Apple was new, bold, and innovative, Guy knew people would be drawn to their company if he simply hyped it up enough. So, he threw himself into generating a buzz about Apple and, thanks to his unique combination of talent and dedication, it wasn’t long before he became one of Apple’s shining stars. He continued to work for Apple for three years, rising through the ranks until he became an influential member of the company’s director board and was eligible for a promotion. He left, however, when his promotion was cancelled in an effort to preserve relations with some of Apple’s competitors.

That might sound like a bizarre choice on Apple’s part — and Guy definitely thought so at the time! — but he ultimately realized that it was the right call. That’s because Guy was so good at his job of convincing people to choose Apple instead of leading brands like Microsoft that their competitors hated him! Apple’s chief operating officer Del Yocam wisely recognized that promoting Guy and giving him more visibility within the company might be a deathwish for Apple. Because although the company was rapidly becoming a household name, Apple was still a little fish in a big pond. If a tech giant like Microsoft went after them, they had no hope of surviving. So, Yocam made a savvy political move to ensure the company’s success.

Even though Guy was angry at the time — and immediately quit to launch his own business — hindsight showed him the wisdom of this decision. And, twelve years later, when Apple went into crisis mode, Guy came back to help the company get on its feet again. Although Apple is now an international tech giant itself and it’s hard to imagine a moment when it wouldn’t be successful, that wasn’t the case in 1995. Its signature Mac computers were suddenly struggling to sell, prompting layoffs that almost crippled the company. They needed their workers to continue production but they also couldn’t afford to pay them! It was a devastating catch-22 and the fledgling start-up’s businessgurus were predicting they would go under soon. They needed some positive publicity — fast! — and Guy was perfect for the job.

So, in the true spirit of a “brand evangelist,” Guy created EvangeList; an email subscription service for Apple users, providing them with exciting updates about the company and its new products. Almost overnight, the list gained 40,000 subscribers and it turned the company around! Thanks to Guy’s leadership and the genius of EvangeList, users rediscovered their love for Apple and Macs started flying off the shelves again. But without the dedication of one bold Guy who was willing to take on an impossible challenge, it’s very likely that Apple would have gone under. In fact, without Guy’s influence, we might never have had the iPhones we love and use every day!

Guy Kawasaki’s upbringing prepared him for success. As the child of hard-working Japanese immigrants, he knew he was expected to make something of himself and he took that expectation seriously. Internalizing his family’s passion, dedication, and refusal to give up, Guy did well in school and made the most of every opportunity life offered to him. Even though his grades weren’t always the best, he had potential that his father and mentors recognized early on. Thanks to their guidance, he followed the right path from ‘Iolani to Stanford to Apple, where he would ultimately fulfill his parents’ dream of becoming successful by the age of 25.

Although neither football nor psychology nor law school proved the right fit for him, Guy quickly discovered that he was made to be a brand ambassador for Apple. Thanks to his natural gifts for connecting with others and brainstorming innovative solutions, he quickly rose through the ranks in a job he wasn’t qualified for and even went on to save the company! Guy’s story proves that you don’t have to follow a traditional model of success to make a name for yourself, you just have to be smart and follow your dreams.