Capitolo 1
The Wisdom Collector's Guide to a Meaningful Life
Have you ever wondered what it would be like to learn life lessons from someone who worked alongside Steve Jobs, turned down the CEO position at Yahoo!, and taught himself to surf at age 61? Guy Kawasaki's "Wise Guy" isn't your typical memoir-it's a collection of stories that offer practical wisdom gained through decades of experience in Silicon Valley and beyond. Unlike many business luminaries who focus on grand achievements, Kawasaki zeroes in on the small, pivotal moments that shaped his thinking and career. The book has earned praise from tech titans and cultural icons alike, with Richard Branson calling it "a blueprint for a life well lived" and Arianna Huffington describing it as "essential reading for anyone seeking to create their own path." What makes this book particularly compelling is how it transforms seemingly ordinary experiences-from childhood encounters to boardroom battles-into profound insights that readers can immediately apply to their own lives.
Capitolo 2
From Hawaii to Silicon Valley: The Journey Begins
Guy Kawasaki's story begins with his grandparents' immigration from Japan to Hawaii in the early 1900s. His paternal grandparents left Hiroshima to work as contract laborers on Hawaiian plantations for $1 per day-choosing hard labor over military conscription in Japan. His father Duke, who began working at age 14, eventually became a state senator for twenty years despite lacking a college education. He created Hawaii's Office of the Ombudsman to help "the common man" and filled their home with books, instilling a love of learning in his son.
On his mother's side, Lucy Kawasaki (under five feet tall but incredibly strong-willed) dedicated herself to her family after studying in Yokohama and fortunately returning to Hawaii on one of the last ships before Pearl Harbor. She taught Guy to "always leave a place neater than you found it" and never to take mistreatment from anyone.
Growing up in working-class Kalihi Valley near a housing project, Guy wasn't wealthy but had parents who invested heavily in their children's futures. The family's immigration story taught him three crucial lessons: change a losing game by taking action, remember the opportunities you've been given, and document your family history while your elders are still alive.
His educational journey took a pivotal turn when sixth-grade teacher Trudy Akau convinced his parents to send him to 'Iolani School, a private college-prep institution, rather than continuing in the public system. Despite the financial strain ($1,250 yearly tuition on a $20,000 income), his parents made the sacrifice. Without Akau's intervention, Kawasaki likely wouldn't have attended Stanford or met the person who later introduced him to Apple.
At 'Iolani, AP English teacher Harold Keables had the greatest impact through his demanding standards. His rigorous writing correction process-circling errors, citing grammar rules, and requiring precise rewrites-instilled a precision that influences Kawasaki's writing to this day. These educational experiences taught him that the toughest teachers are often the most valuable, and that one person's intervention can completely alter a life's trajectory.
Capitolo 3
The Power of Inspiration: Finding Motivation in Unexpected Places
Kawasaki's ambitions weren't driven by lofty ideals like world peace or human rights, but by simple, proletarian goals that nonetheless provided powerful motivation. His father's love for Cadillacs-big, powerful, air-conditioned cars with leather seats-was a point of pride even though they lived in a poor area. This seemingly shallow motivation-wanting to drive nice cars-drove him to study and work hard. Later, seeing parents arrive at Stanford in exotic cars like Dr. Nobuyuki Kawata's metallic-blue Ferrari 275 GTB further expanded his sense of what was possible.
In 1987, his wife gave him a copy of "If You Want to Write" by Brenda Ueland, which influenced him more than any other book. Its essence is simple yet powerful: if you want to write, ignore critics and naysayers-especially your internal ones-and just write! This book empowered him to think freely and boldly, enabling him to write his first book, "The Macintosh Way," despite not considering himself an "author."
Even negative experiences served as inspiration. Being robbed twice in high school by "mokes" (Hawaiian slang for tough guys) left him feeling fearful and cowardly for not fighting back. Though he lost only a few dollars each time, these experiences motivated him to study hard and work diligently-he never wanted to ride a public bus again or live in a high-crime area.
Perhaps the most profound lesson came from former Secretary of State Condoleezza Rice, who grew up in Birmingham during the height of racial segregation in the 1950s. She taught him never to consider himself a victim. Growing up where Bull Connor used fire hoses and police dogs to enforce segregation, Rice explained that adopting a victim mindset means surrendering control of your fate to others. When you believe you're a victim, you start acting like one, becoming dependent on others for your happiness and success.
This fundamentally shifted Kawasaki's understanding of personal responsibility. If Rice from Birmingham and he from Kalihi Valley could succeed despite obstacles, anyone can-but not while clinging to victimhood.
Capitolo 4
The Apple Years: Lessons from Steve Jobs
Kawasaki worked at Apple from 1983 to 1987, and then from 1995 to 1997-experiences that shaped his career and identity. Despite having no computer background-just a psychology degree, MBA in marketing, and jewelry industry experience-he landed at Apple through connections after seeing a Mac demonstration that left him awestruck.
Steve Jobs wasn't entirely convinced when hiring him, telling Mike Boich "You can hire Guy, but you're betting your job on him." Kawasaki succeeded because Macintosh was genuinely revolutionary, he was in the right place at the right time, his jewelry sales experience prepared him for hand-to-hand evangelism, and most importantly, he outworked nearly everyone.
Working for Jobs taught him the power of honesty. One day in 1984, Jobs appeared at his cubicle with an unintroduced visitor and asked what he thought about Knoware. Kawasaki bluntly stated their products were mediocre, boring, and not strategic for Apple. Only then did Jobs introduce him to Archie McGill, Knoware's CEO, saying "See? That's what I told you."
Working for Jobs was unpleasant and scary, but it drove everyone to do their finest work. The lesson: tell the truth-it demonstrates both competence and character. Had Kawasaki sugarcoated his assessment, Jobs would have either considered him clueless or fired him on the spot.
During his second Apple stint, Kawasaki created EvangeList, an email list with 40,000 subscribers that broadcast positive Apple news and developer announcements. Though Jobs' return and the colorful iMac line were the biggest factors in Apple's rebound, the preservation of the passionate Mac community was crucial-they continued buying Macs and developing software when others abandoned ship.
This experience taught him that people love contributing to causes they believe in, and that true evangelism requires a great product-what he calls "Guy's Golden Touch," meaning "whatever is gold, I touched."
Kawasaki's Apple years yielded eleven key lessons: only excellence matters; customers can't tell you what they need; innovation happens on the next curve; design counts; less is more; big challenges beget big accomplishments; changing your mind is a sign of intelligence; engineers are artists; price and value are not the same thing; value isn't enough without uniqueness; and some things need to be believed to be seen.
Capitolo 5
Business Wisdom: From Jewelry Sales to Silicon Valley Success
After dropping out of law school, Kawasaki entered UCLA's MBA program in 1977. During his studies, he met Lynn Nakamura who worked for Nova Stylings, a jewelry manufacturer owned by the Gruber family. She offered him a part-time job counting diamonds, which led to a full-time position after graduation instead of the typical investment banking or consulting path.
This decision proved invaluable because Nova's CEO, Marty Gruber, taught him how to sell-perhaps the most valuable skill he's ever learned. The jewelry business was brutal hand-to-hand combat, tougher than tech. Buyers would weigh your product, calculate the gold value, and offer 10% over scrap value payable in 120 days. Working at this Jewish family business taught him crucial lessons: learn to sell (because life is sales), earn people's trust, prove yourself through hard work, and diversify your acquaintances.
Throughout his career, Kawasaki discovered that innovation often happens accidentally, like when the chef at Honolulu Kitchen dropped a manapua (pork bun) into hot oil and created a delicious fried version. Many believe entrepreneurs plan their companies' evolution linearly, but the truth is that most start with simpler questions. Bill Gates likely just wanted IBM's business for the PC, while Steve Jobs and Wozniak wanted to sell Apple Is to the Homebrew Computer Club.
He also learned the importance of the "second follower." While early employees are typically the first adopters of a new idea, the crucial second adopter is often the first customer. This concept proved vital at Apple in 1984 when trying to sell Macs to businesses. Peat Marwick (now part of KPMG) became that essential reference account-the only large company besides Apple using Macs. The truth was they were the only major customer, but their validation made all the difference, even though Apple provided extraordinary support that wouldn't scale.
Kawasaki's journey to becoming Canva's chief evangelist began with an improbable chain of events: his coauthor Peg Fitzpatrick used Canva for his tweets; Canva's team noticed and reached out; and the founders happened to be visiting the US shortly after. But Canva's rise from unknown Australian startup to billion-dollar unicorn wasn't luck. Founders Melanie Perkins and Cliff Obrecht recognized two crucial shifts: graphics were becoming essential for communication, and existing design tools were too expensive and complex. Rather than just taking market share, they expanded the entire market by enabling people who previously couldn't create graphics.
Capitolo 6
Values That Shape a Life: Honor, Humility, and Human Connection
Kawasaki's life has been guided by two primary goals: raising four kids who are joyful, productive, and socially responsible; and empowering people to change the world. Two remarkable experiences taught him the value of honor in business. When Steve Case's Quantum Computer Services lost their Apple contract in 1989, Kawasaki offered consulting help for $2,000 monthly plus stock options. Though he only worked briefly and never received the promised options, years later Case insisted he receive them anyway-options that split multiple times and became extremely valuable.
Similarly, after informally advising iStockphoto (without formal compensation agreements), founders Patrick Lor and Bruce Livingston voluntarily paid him 1.5% of their $50 million acquisition by Getty-triple the typical advisor compensation. These experiences showed him that formal contracts with dishonorable people are worth less than informal agreements with honorable ones.
Humility has also been a powerful lesson. In 2008, Kawasaki met Richard Branson at a conference in Moscow. When he explained he was loyal to United Airlines for his Global Services status, Branson dropped to his knees and started polishing his shoes with his coat to convince him to fly Virgin instead. That was the moment he decided to switch airlines. If a billionaire knight who owns an island and kitesurfs with Barack Obama can humble himself for business, it demonstrates how humility can be a powerful tool for success.
Kawasaki's values were tested during the 2016 US presidential election. After dinner with German friends in Berlin who drew parallels between Trump and Hitler's rise, warning "If Trump wins, it will be 1933 for America," he turned his social platforms into political feeds, despite social media experts advising against mixing business and politics. While he lost a few thousand followers, he gained tens of thousands more by standing up for his principles. Even if it had cost him followers, branding, or income, he would have still done it-that's what he'll tell his grandchildren.
Over his career, Kawasaki developed several decision-making tests that provide structure for determining right and wrong. The Wikipedia/NPR Donation Test asks whether you provide such value that people would gladly reciprocate. The Re-share Test examines whether your work is so good people would risk their reputations recommending it. The Shopping Center Test reveals relationship quality by asking if you'd rush to greet someone you spotted unexpectedly. The So-What? Test helps put "crises" into perspective by repeatedly asking "so what?" to follow consequences to their logical conclusion.
Capitolo 7
The Joys and Challenges of Parenting
Kawasaki met his wife Beth at Apple in 1983-love at first sight. They have four children: Nicodemus (1993), an economics graduate who became a UI designer; Noah (1995), an economics graduate with a passion for skydiving who joined a data analytics firm; Nohemi (2001), their "warrior woman" adopted from Guatemala who surfs and started her own media business; and Nathan (2005), "Mr. Charisma" also adopted from Guatemala, with a bold personality destined for sales.
Their family includes two biological sons and two children adopted from Guatemala. Adoption has been as beneficial for them as parents as it was for their children. Having Nohemi brought the joy of watching a daughter play hockey and surf. Two years after adopting her, they received a call that her brother was available for adoption, allowing them to keep siblings together. They went from "man-to-man" parenting (two parents, two kids) to "zone" defense (two parents, four kids).
Parenting has taught Kawasaki many lessons, including the importance of preparation. When his son Noah failed his driving test twice, he had the brilliant idea to drive to the DMV and watch examiners take applicants on road tests. They then practiced the exact route, and Noah earned a perfect score on his third attempt. The lesson: always prepare for tests, interviews, and challenges-there's always a way. Three factors often prevent proper preparation: arrogance ("I don't need to prepare"), laziness ("I'm too busy"), and stupidity ("I'll probably fail anyway").
He's also learned that you can only do so much as a parent. During his interview at an elite prep school, his son Nicodemus told the admissions director he wanted to play tackle football-which the school didn't offer. Later, when meeting with a UCLA vice chancellor who asked if he had questions, he only wanted to know where the hockey team practiced. Neither school accepted him. Ironically, he got into UC Berkeley without telling his parents he'd even applied. The lesson: you can hover over your kids or lawnmower in front of them, but things will work out without your interference.
Perhaps most powerfully, Kawasaki learned to empathize through his son Nate's dyslexia. At his school's open house, parents could experience exercises simulating dyslexia. Kawasaki couldn't complete any of them-not even close-and cried afterward because it was the first time he truly understood what his son experiences. The issue wasn't intelligence, focus, or diligence. This taught him to empathize with others by walking a mile in their shoes before judging.
Capitolo 8
Finding Joy Through Sports and Lifelong Learning
From seventh grade onward, sports became Kawasaki's passion. Though not naturally athletic, he compensated with determination-the story of his life generally. At forty-eight, he took up hockey after his sons fell in love with the game. His wife encouraged him to participate rather than be a sideline Silicon Valley dad on his BlackBerry. Despite never having skated before, he became obsessed, playing almost daily and taking his equipment worldwide. These experiences taught him that acquiring new skills is a lifelong process that makes you more interesting and connects you with people beyond your usual circles.
At sixty-one, he tried paddleboarding at a UC Santa Barbara summer camp, drawn by his "Jesus complex"-the desire to walk on water, whether frozen (hockey) or liquid (surfing). Initially paddleboarding was just to strengthen his core for hockey, but when his daughter Nohemi became passionate about surfing, he wanted to share her interest. Through connections, he met Jeff Clark, discoverer of Mavericks, the legendary big-wave surfing location.
After months of practice, he transitioned from paddle surfing to "surping" (using a paddleboard for prone surfing), eventually getting a custom surfboard from legendary shaper Bob Pearson. This board changed his life. By summer 2017, he was surfing twice daily, sometimes with all four of his kids-precious moments he'll never forget.
These experiences taught him that it's never too late to learn new skills and that life tends to regress to the mean. After an eye injury forced him to play hockey wearing glasses instead of contacts, he experienced an unprecedented scoring streak-six goals in consecutive games, then four, then two. He considered superstitious explanations: the expensive Jamaica Blue Mountain coffee he'd drunk, improved vision from glasses, or even the foggy glasses forcing better concentration. But eventually he returned to his usual mediocre performance.
The wisdom? Don't get too cocky when things go well or too negative when they go poorly. Life balances out-just keep working to raise your average.
Capitolo 9
The Craft of Communication: Writing, Speaking, and Social Media
Kawasaki wrote his first book, The Macintosh Way, in 1987 from a tiny closet-sized workspace using a Mac Plus with 1MB of RAM. Though he thought he'd never write another book after pouring everything he knew into that first one, Wise Guy became his fifteenth book. After fifteen books and countless articles, he's learned crucial writing lessons: Read extensively to become a better writer (especially Brenda Ueland's If You Want to Write); only write when you have something important to say, not for fame or fortune; embrace the editing process through multiple drafts; and hunt down and eliminate adverbs and passive voice.
Unlike many people who find public speaking stressful, Kawasaki has given over fifty speeches annually since 1987 to audiences as large as 25,000. His speaking wisdom includes using white text on black backgrounds as it shows PowerPoint mastery, requesting small rooms for a packed feeling, befriending the AV team, pre-circulating with the audience before speaking, customizing your opening with audience connections, starting strong like an F/A-18 fighter jet rather than a slow A380, using maximum ten slides with at least 30-point text, limiting presentations to twenty minutes, and always telling stories.
His approach to social media is pragmatic-a means to promote products, companies and causes rather than making friends. He focuses on providing information, assistance and entertainment to earn the privilege of promoting his work. With approximately twelve million followers across platforms by 2018, being an "influencer" has brought three benefits: presumed credibility leading to speaking opportunities, exceptional customer service, and a flow of freebies he eventually started declining.
His social media wisdom includes adding value to people's lives before soliciting support; understanding that users make instant Tinder-like decisions about your content; optimizing your avatar (just your face) and cover photo; being positive or staying silent because "transparency is overrated if you're an asshole"; repeating posts despite occasional complaints; and keeping experimenting rather than blindly following expert advice.
Capitolo 10
The Power of Ohana: Building a Meaningful Life Through Relationships
Ohana is the Hawaiian word for "family" that extends beyond blood or marriage to include anyone with whom you have a deep relationship. Throughout his book, Kawasaki highlights how these connections have enriched his life and taught him valuable lessons.
Craig Stein, founder of The Hired Executive and Kawasaki's surfing buddy, recalls meeting him during a 2005 presentation at Ohio State University. He was impressed by Kawasaki's confidence in offering clients a double-or-nothing deal: if he didn't receive a standing ovation, he'd waive his speaking fee, but if he did, they'd pay double. Craig learned that the real wisdom wasn't about negotiation tactics but about committing to excellence-when you reach the top of your field, you develop a deep, quiet confidence.
Bruna Martinuzzi, author of "The Leader as a Mensch," emailed Kawasaki one night asking for laptop advice. To her amazement, he responded within ten minutes recommending a Mac with a solid-state drive and Apple Care. This simple act of kindness-helping a complete stranger who couldn't offer anything in return-made a lasting impression.
Nic Kawasaki, Guy's oldest son, recalls a December night when his father surprised him by showing up at his late-night adult hockey league game. Despite being 24 and living independently, Nic was touched seeing his dad sitting alone in the stands at 10:30 PM, watching him play "a meaningless adult hockey league game." This moment reminded Nic of his father's consistent presence throughout his life-attending countless sports events, even chartering private jets to make it to important games, and playing hockey alongside him.
Peg Fitzpatrick, Kawasaki's coauthor on "The Art of Social Media," recalls visiting a Walgreens with him. After picking up photos, Kawasaki bought milk, bread, peanut butter and jelly, then quietly gave these groceries to a homeless man outside-a thoughtful act Peg believes he probably doesn't even remember doing. This small gesture demonstrated how instead of being overwhelmed by larger social problems, Kawasaki simply helped one person with what he could provide in that moment.
Through these relationships and experiences, Kawasaki has distilled his top ten wisdoms: 1) Get high and to the right by acquiring unique and valuable skills; 2) Adopt a growth mind-set, understanding that learning is a lifelong process; 3) Embrace grit, recognizing that success requires hard work and determination; 4) Smile, as laughter makes life easier; 5) Default to yes, assuming people are good; 6) Raise the tide, understanding life isn't zero-sum; 7) Pay it forward, as good deeds are investments in your future; 8) Examine everything with skepticism but not negativity; 9) Never lie, seldom shade, as honesty sets you free; and 10) Enable people to pay you back to honor them and foster their self-worth.
His ultimate advice? Dance to your own music before life ends.
