Wise Guy summary

Guy’s grandparents came to America because they saw it as a land of opportunity. Because they themselves had missed out on a good education, his parents understood that that was the surest path to social advancement.

They were more than happy to act on the advice of his sixth-grade teacher, Trudy Akau, when she called them and convinced them to apply Guy to two private college-prep schools in Honolulu: Punahou, the institution attended by former president Barack Obama, and ‘Iolani. The decision would change his life.

If you were an Asian- or Jewish-American kid back in the 1970s, your parents most likely had three career tracks laid out for you: a dentist, doctor or lawyer. Guy toyed with the idea of studying medicine at Stanford but soon realized he wasn’t cut out for such grisly work. A life spent sticking his hands in peoples’ mouths didn’t appeal either. That left law.

So after graduating from Stanford in 1976, Guy packed his bags and drove up to join Russell Kato, an old friend from ‘Iolani, to study law at University of California, Davis.

Guy’s romance with computing first blossomed during his time in the jewelry trade after Mike Boich, another pal from Stanford, introduced him to the Apple II home computer. Compared to the IBM Selectric typewriter he’d been using, the AppleWorks word processor was an absolute godsend. When Boich later told him there was an opening at the company making these brilliant products, Guy jumped at the opportunity.

In September 1983, he joined Apple’s Macintosh Division as a “software evangelist,” a kind of brand ambassador. It was a lucky break. As Guy readily admits, on paper he didn’t look like the right man for the job. His résumé was littered with seemingly irrelevant qualifications – his psychology degree and MBA – and work experience in unrelated fields. Steve Jobs, the mastermind behind Apple, wasn’t convinced. He told Boich that he could hire Guy but that Boich was ultimately staking his career on the decision!

Apple has long been synonymous with perfectionism, and its bosses have always been hard taskmasters. During Guy’s time with the Macintosh Division, employees were expected to prove themselves every day.

Guy did exactly that. By 1986, he’d been with the company for three years and was up for promotion. That meant not only a seat on the directors’ board but a raise, stock options and a company car. There was just one problem: his superior, chief operating officer Del Yocam, was opposed to it. Apple was still reliant on the goodwill of competitors to get its own products off the ground, and while Guy enjoyed excellent relations with smaller companies, three big names in software hated him: Microsoft, Lotus and Ashton-Tate.

Apple is such a global powerhouse today that it’s hard to imagine there was a time when it looked like it might sink without a trace. But that’s exactly what industry insiders were predicting in 1995. Steve Jobs had left ten years earlier, Apple’s signature product – Macintosh – was struggling in the marketplace, and the company was being decimated by layoffs as it struggled to steady its finances. Desperate for all the help he could get, Apple’s vice president Dan Eilers reached out to Guy.

Guy had never lost his love for Apple and agreed to take up the position of chief evangelist. His task? To preserve Macintosh’s brand image and retain the customers of its thinning user base – hardy souls who defied computing common sense and continued buying a product experts believed was about to become extinct. It was a job with Guy’s name on it. During his first “tour of duty” at Apple, he’d spent endless hours supporting user groups and knew from personal experience just how fiercely loyal Mac users could be once you won their trust.

Despite all his professional successes, Guy values his personal achievements most. Top of the list: the family he’s raised with his wife Beth, a former Apple colleague whom he first met and fell in love with in 1983. As anyone with kids of their own will know, parenting isn’t always straightforward, but it is incredibly rewarding. For Guy, that comes down to a simple fact: children teach you more about yourself and the world around you than any school, university or workplace ever could.

The most important lesson? Never judge anyone until you’ve walked in their shoes. That’s something Guy learned from his son Nate, who has dyslexia – a condition that makes concentrating on letters and numbers extremely difficult. Initially, Beth and Guy were frustrated by Nate’s poor progress in school. But then they went to an open evening during which Nate’s teachers invited them to take part in an exercise which simulated the experience of dyslexia by reversing texts in a mirror. After failing to complete a single task, Guy burst into tears – it was the first time he’d truly seen the world through his son’s eyes.

Surfing wasn’t all about painful memories for Guy, however. In fact, it not only helped him bond with his initially critical daughter, but also taught him that contrary to perceived wisdom, old dogs can learn new tricks.

If you’ve never surfed before, you might not know that there are two different types of surfing – paddle and prone surfing. In the former, the rider remains standing and, as the name suggests, uses a paddle for balance. That’s a whole lot easier than the second, more traditional variant in which the rider lies on their board before springing into a standing position as they “catch” a wave.