Wise Guy

Wise Guy Plot Summary

Introduction

In the ever-evolving world of technology and entrepreneurship, few individuals have managed to shape an industry while remaining relatable and authentic. Guy Kawasaki emerged from modest immigrant roots to become one of Silicon Valley's most influential voices, creating a blueprint for modern technology evangelism and digital marketing that continues to resonate decades later. His journey traverses multiple roles—from Apple's chief evangelist during the pivotal Macintosh era to venture capitalist, bestselling author, and global speaker—all while maintaining his characteristic blend of practical wisdom and irreverent humor. What makes Kawasaki's story particularly compelling is his unique ability to translate complex business concepts into accessible insights while refusing to take himself too seriously. Throughout his career, he has consistently challenged conventional wisdom about success, emphasizing values like honesty, perseverance, and human connection over mere technical prowess or business acumen. Through his journey, we discover profound lessons about creating meaningful work, building authentic relationships, and finding purpose beyond profit in a rapidly changing technological landscape.

Chapter 1: Immigrant Roots and Educational Foundation

Guy Kawasaki's story begins with his grandparents' emigration from Japan to Hawaii in pursuit of better opportunities. His great-grandparents left Hiroshima between 1890 and 1900, during a turbulent period marked by the First Sino-Japanese War and the Russo-Japanese War. Rather than face military service, they chose to work as contract laborers for the Hakalau Plantation Company in Hawaii, earning merely a dollar per day harvesting sugar—a decision that would shape generations to come. Growing up in Kalihi Valley, a working-class neighborhood of Honolulu, Kawasaki was raised in a family that emphasized education despite limited means. His father, who began working at fourteen to support the family, eventually became a fireman and later served as a state senator for approximately twenty years. His mother dedicated herself entirely to their family, instilling in him values of neatness and resourcefulness. Despite never attending college themselves, his parents prioritized education for their children, understanding how their own limited opportunities had constrained their options in life. The trajectory of Kawasaki's education changed dramatically when his sixth-grade teacher, Trudy Akau, recognized his potential and urged his parents to send him to a private college-preparatory school. This intervention proved pivotal, as Kawasaki was accepted to 'Iolani, an elite Episcopalian prep school that cost $1,250 per year—a substantial sum for a family with a modest income of approximately $20,000. This educational leap exposed him to rigorous academic standards and mentors who would profoundly influence his thinking. Among these influential educators was Harold Keables, Kawasaki's AP English teacher, who demanded excellence and precision in writing. Keables' meticulous approach to grammar and style instilled in Kawasaki a lifelong appreciation for clear, effective communication. The lessons were harsh but invaluable—students had to identify and correct every writing error by citing the violated rule and rewriting the sentence correctly. This rigorous training would later serve Kawasaki well in his writing career, where his straightforward, accessible style would become his trademark. After graduating from 'Iolani, Kawasaki attended Stanford University, another transformative experience that expanded his horizons. The move from Hawaii to California exposed him to a world of possibilities beyond what he had known in Honolulu. At Stanford, he met Mike Boich, who would later hire him at Apple and set him on the path to technological evangelism. This period at Stanford marked the beginning of Kawasaki's understanding that his future lay not in traditional professional paths like medicine or law, but in the emerging world of technology and entrepreneurship.

Chapter 2: Finding Purpose Through Apple and Evangelism

Kawasaki's entry into Apple in 1983 came through an unusual route and with unconventional qualifications. With a psychology degree and MBA in marketing, plus several years in the jewelry business, he lacked the technical background typically expected in the computer industry. Yet when Mike Boich introduced him to the Macintosh, Kawasaki experienced what he describes as a "religious experience"—the clouds parted, angels sang, and he was utterly captivated by the revolutionary technology. Despite Steve Jobs' lukewarm initial assessment—reportedly telling Boich, "You can hire Guy, but you're betting your job on him"—Kawasaki was brought on as a software evangelist for the Macintosh Division. His role involved convincing software and hardware companies to create products for a computer with no installed base, incomplete tools, and draft documentation. What he lacked in technical expertise, he made up for with sales skills honed in the jewelry business, where he had learned to sell commodities through direct, person-to-person interaction. Evangelism at Apple was not merely selling; it was spreading the gospel of a revolutionary product that could change how people worked and created. Kawasaki approached this mission with religious fervor, turning the technical challenge of software adoption into a moral and philosophical cause. Under Jobs' demanding leadership, he learned to value excellence, honesty, and innovation. When once asked his opinion about a company called Knoware, Kawasaki bluntly told Jobs their products were mediocre and simplistic—only to discover moments later that he was speaking to Knoware's CEO. Rather than being fired for his candor, Kawasaki's honest assessment reinforced his value to Jobs, who prized authenticity and excellence above politeness. During his tenure at Apple, Kawasaki witnessed firsthand the principles that would later define his approach to business and marketing. From Jobs, he absorbed crucial lessons: that excellence matters above all else; that customers can't tell you what they need; that innovation happens on the next curve, not by improving the status quo; and that design counts profoundly. These principles became the foundation of what Kawasaki would later call "Guy's Golden Touch"—not that whatever he touched turned to gold, but that whatever was gold, he touched. After leaving Apple in 1987 to co-found ACIUS, a software company, Kawasaki would return to Apple for a second tour of duty from 1995 to 1997. During this challenging period when many believed Apple might not survive, he served as an Apple fellow and chief evangelist, preserving the Macintosh cult through initiatives like EvangeList, an opt-in email list with over forty thousand subscribers that broadcast positive news about Apple. While Jobs' return would ultimately save the company, Kawasaki's efforts to maintain the developer community and user base during Apple's darkest hours contributed significantly to keeping the company afloat until its renaissance.

Chapter 3: The Art of Entrepreneurship and Writing

Following his departure from Apple, Kawasaki embarked on a journey that would transform him from a corporate evangelist to a multifaceted entrepreneur and author. His first venture as CEO of ACIUS in 1987 laid the groundwork for a career path marked by diverse entrepreneurial endeavors, including roles as CEO of Fog City Software and Garage.com. Each position allowed him to apply the lessons learned at Apple while developing his own philosophy of business built on authenticity, value creation, and human connection. Kawasaki's transition to writing began with his first book, "The Macintosh Way," written in 1987 while he was CEO of ACIUS. Composed in a closet-sized work area using a Mac Plus with 1 megabyte of RAM and an 800K floppy drive, the book explained how to "do the right things the right way" based on his experiences in the Macintosh Division. Though he initially thought he would never write another book because he had nothing more to say, this debut launched a prolific writing career that would ultimately span fifteen books and establish him as one of technology's most influential voices. What distinguishes Kawasaki's approach to business and writing is his emphasis on practical wisdom over theoretical frameworks. Through his experiences, he developed compelling insights: that the best ideas often come from simple questions like "Therefore, what?" or "Is there a better way?"; that stories trump adjectives when communicating value; and that small changes can make big differences. Rather than focusing on grand strategic visions, Kawasaki championed "clever" over "strategic," arguing that quick, incremental improvements often yield greater results than elaborate, expensive initiatives. Kawasaki's entrepreneurial philosophy also embraces serendipity and relationship-building. His role as chief evangelist for Canva, which began in 2014 after a chance interaction on Twitter, illustrates how unexpected connections can lead to significant opportunities. The Australian design startup grew from an unknown entity to a "unicorn" valued at $1 billion, with Kawasaki playing a key role in its global evangelism. This success stemmed not from elaborate planning but from Kawasaki's willingness to recognize value, take chances, and commit to a marathon of relationship-building and consistent effort. Throughout his entrepreneurial journey, Kawasaki developed a distinctive approach to business characterized by honesty, directness, and a focus on creating genuine value. He championed the importance of customer gratification, the power of finding the right reference accounts, and the necessity of focusing on benefits rather than features. Most importantly, he recognized that business success comes not from manipulation or aggression but from creating products and services that so delight customers that they willingly advocate on your behalf—what he later called the "Wikipedia/NPR Donation Test" of value creation.

Chapter 4: Building Influence in the Digital Age

As the internet transformed from a technical curiosity to a central force in business and culture, Kawasaki adapted his evangelism skills to the digital landscape, becoming one of social media's most influential voices. His initial skepticism about platforms like Twitter—which he first dismissed as a forum for trivial personal updates—gave way to recognition of their potential for brand building, customer support, and competitive intelligence. This pragmatic approach to digital influence became characteristic of Kawasaki's methodology: focusing not on technology for its own sake but on its practical applications for connecting with audiences and adding value. By 2018, Kawasaki had amassed approximately twelve million followers across LinkedIn, Twitter, Facebook, Google+, and Instagram—an achievement made more remarkable by the fact that he built this following organically, without purchasing followers. His success stemmed from a fundamental insight: social media functions best as a means to an end, with the "end" being the successful promotion of products, companies, and causes. Rather than pursuing social connections for their own sake, Kawasaki viewed digital platforms as tools for earning attention through providing information, assistance, and entertainment. Kawasaki's approach to social media embodied several key principles that distinguished him from other influencers. He emphasized adding value to people's lives, likening social media engagement to the NPR model of providing great content to earn the right to solicit support. He recognized that users make instant decisions about whom to follow, comparing social media to Tinder rather than eHarmony in terms of decision-making speed. He advocated optimizing visual elements like avatars and cover photos, maintaining positivity in interactions, strategically repeating content across platforms, and constantly experimenting with new approaches. The influence Kawasaki built online translated into tangible benefits: presumed credibility that led to speaking and consulting opportunities, exceptional customer service from brands eager to address his concerns, and a flow of promotional items so abundant that he eventually began declining them. Yet more important than these personal advantages was the platform his influence provided for promoting causes and companies he believed in—from Canva's democratization of design to political activism during contentious periods in American politics. Perhaps most notably, Kawasaki demonstrated how digital influence could be leveraged for principled stands even at personal cost. Following the 2016 U.S. presidential election, he transformed his social media accounts into platforms for political resistance, contrary to conventional wisdom that advised maintaining political neutrality to preserve follower counts. While some followers objected, the response was overwhelmingly supportive, with many praising his willingness to risk his brand for his convictions. This integration of personal values with digital strategy illustrated Kawasaki's belief that influence carries moral obligations that transcend marketing considerations.

Chapter 5: Family Values and Personal Philosophy

Behind Guy Kawasaki's public persona as a technology evangelist and business guru lies a deeply personal foundation built on family values and life experiences. His marriage to Beth Kawasaki and their raising of four children—Nicodemus, Noah, Nohemi, and Nathan—represents what Kawasaki considers his greatest achievement. When asked what he wants to be remembered for at the end of his career, his answer is unequivocal: as a father, not as an entrepreneur, author, speaker, or influencer. Adoption has played a central role in shaping Kawasaki's family experience and values. While his two older sons are biological children, his younger daughter and son were adopted from Guatemala. This experience has been transformative, leading Kawasaki to conclude that adoption is "as good for the parents as it is for the children." Through adoption, the Kawasaki family expanded from what he humorously describes as "man-to-man" coverage (two parents, two kids) to "zone" defense (two parents, four kids), creating a rich multicultural household that has profoundly influenced his perspective on family and privilege. Kawasaki's parenting philosophy emphasizes presence and involvement over dictation or control. Rather than imposing his passions on his children, he has consistently followed their lead—taking up hockey when his sons became interested and later embracing surfing to share in his daughter's enthusiasm. This approach reflects his understanding that "parental control" is largely an illusion. As he puts it, parenting is essentially being "a Lyft driver and an ATM rolled into one," a role he has embraced with humor and grace while cherishing the time spent with his children. Through various life experiences, Kawasaki has developed a series of philosophical "tests" that guide his decision-making. The "Wikipedia/NPR Donation Test" asks whether you provide something of such value that people will gladly reciprocate. The "Re-share Test" considers whether your efforts are so good that others would risk their reputations to recommend them. The "Shopping Center Test" reveals the quality of relationships by asking whether you would rush to greet someone you spotted, casually approach them, or avoid them entirely. And the "So-What? Test" helps put apparent crises into perspective by repeatedly asking "So what?" until the true significance of a problem becomes clear. These philosophical frameworks reveal Kawasaki's practical wisdom about what truly matters in life. Despite his success, he maintains a grounded perspective, shaped in part by experiences like his diagnosis with Ménière's disease—a condition causing hearing loss, tinnitus, and vertigo that he came to view as "the worst of the best diseases" because while inconvenient, it isn't fatal. Such experiences have taught him gratitude, patience, and the importance of distinguishing between genuine challenges and minor inconveniences—wisdom that has proved as valuable in personal life as in business.

Chapter 6: Sports, Surfing, and Embracing New Challenges

Throughout his life, Guy Kawasaki has demonstrated a remarkable willingness to embrace new challenges, particularly in sports and physical activities. Despite not considering himself a "natural athlete," Kawasaki has pursued various sports with determination and enthusiasm, embodying his philosophy that what he lacks in innate ability, he makes up for with persistence—a pattern that mirrors his approach to business and life in general. Kawasaki's sporting journey began with football in high school, where coaches taught him the value of hard work and teamwork. After college, he cycled through tennis and basketball before taking up ice hockey at the age of forty-eight—an unusually late start for such a demanding sport. The decision came after a San Jose Sharks game that his sons enjoyed, prompting them to express interest in playing. Rather than watching from the sidelines like a "typical Silicon Valley father... tapping away on a BlackBerry," as his wife cautioned against, Kawasaki committed to learning alongside his sons, despite having never skated before. This late-in-life hockey obsession led to remarkable experiences, including games with NHL stars Eric Lindros and Bret Hedican, and playing in venues from Doha to Bratislava. In one particularly memorable instance, Kawasaki played in Slovakia's Ondrej Nepela Arena with Peter Stastny, a Hockey Hall of Fame member. These experiences weren't merely recreational—they expanded Kawasaki's network beyond technology circles and enhanced his public persona as someone with diverse interests and a willingness to step outside his comfort zone. At age sixty-one, Kawasaki embraced yet another challenging sport: surfing. Beginning with paddleboarding during a family summer camp, he gradually transitioned to prone surfing despite initial difficulties. His approach exemplified his lifelong learning philosophy—seeking expert coaching from figures like Kainoa McGee and Calder Nold, practicing diligently, and being unafraid to take unconventional approaches, such as using a paddleboard as an introductory surfboard despite criticism from traditional surfers. Kawasaki's surfing journey also led to unexpected connections, including a friendship with world champion surfer Shaun Tomson, whom he met by chance in an Apple store. This relationship yielded mutual benefits—Tomson helping with Kawasaki's surfing, and Kawasaki assisting with Tomson's writing and speaking. Such serendipitous connections, facilitated by Kawasaki's openness to new experiences and willingness to engage with strangers, illustrate how his sporting interests have enriched his life beyond physical activity. The wisdom Kawasaki gained from these late-life athletic pursuits extends beyond sport-specific skills. He learned to follow his children's interests rather than imposing his own, to persist through initial failures, to ignore naysayers and critics, to think creatively about learning approaches, to invest in quality equipment when necessary, and to find expert coaches who can accelerate development. Most importantly, he discovered that age need not limit new pursuits—that with sufficient dedication, even sexagenarians can develop meaningful proficiency in demanding physical activities.

Chapter 7: Wisdom Through Relationships and Ohana

At the heart of Guy Kawasaki's philosophy lies the Hawaiian concept of "ohana"—family that extends beyond blood relations to encompass anyone with whom one shares deep connections. This principle has guided his approach to relationships throughout his life, creating a network of meaningful associations that transcend traditional professional boundaries. To illuminate this dimension of his character, Kawasaki invited members of his extended ohana to share stories illustrating the wisdom they gained through their interactions with him. These personal accounts reveal a consistent pattern of generosity and authenticity that has characterized Kawasaki's relationships. Bruna Martinuzzi, for instance, recounts how Kawasaki responded to her email inquiry about laptop recommendations within ten minutes, despite her being a complete stranger who offered nothing in return. This willingness to help people who "cannot help you" exemplifies what Martinuzzi considers "a measure of a person's goodness"—how they treat someone who can be of no use to them. Similarly, Peg Fitzpatrick describes accompanying Kawasaki to pick up photos at Walgreens, where he spontaneously purchased groceries for a homeless man outside the store—an act of kindness he performed without fanfare and likely didn't even remember later. This small gesture illustrates Kawasaki's philosophy of helping "when you can, where you can," focusing on tangible actions rather than becoming paralyzed by the magnitude of larger social problems. Family relationships, particularly with his children, reveal another dimension of Kawasaki's character. His oldest son, Nic, shares the powerful memory of his father attending a late-night adult hockey league game—sitting alone in the stands, watching his twenty-four-year-old son play "a meaningless adult hockey league game in the middle of the night." This dedication to remaining present in his children's lives, despite a demanding travel schedule, made a profound impression on Nic, who concluded that "no matter how old I get... I will always be my father's son, and he will always love me like one." Professional relationships also reflect Kawasaki's values of competence over credentials and genuine connection over formality. Shawn Welch, who co-authored a book with Kawasaki after responding to his public request for technical help, notes how Kawasaki "looks for competence, not a résumé" and "isn't afraid to admit what he doesn't know." This humility extends to Kawasaki's long-term professional relationships, as his editor Rick Kot describes their twenty-eight-year collaboration as one where both parties brought "not only their expertise to the table but also the willingness to put up a good fight, a sense of humor, and ultimately the flexibility to know when to capitulate." Perhaps most revealing is Kawasaki's daughter Nohemi's observation about his habit of initiating conversations with strangers while surfing, often leading to invitations to try his board or visit their home. Through this "giving spirit," she notes, he has "created a network of relationships in all sorts of different areas," teaching her the importance of generosity toward "anyone, even people you don't know."

Summary

Guy Kawasaki's journey from a modest upbringing in Hawaii to becoming a Silicon Valley icon embodies a distinctively American success story—one built not on inherited privilege or extraordinary genius, but on relentless effort, adaptability, and genuine human connection. Throughout his multifaceted career as Apple evangelist, entrepreneur, author, and influencer, Kawasaki has consistently demonstrated that the path to meaningful achievement lies in finding what you love, working diligently to master it, and generously sharing your knowledge with others. The central insight from Kawasaki's life is what he calls "getting high and to the right"—acquiring skills that are both unique and valuable. This principle extends beyond professional development to encompass his approach to personal growth, family relationships, and community engagement. Whether writing books in a closet-sized workspace, learning to surf in his sixties, or taking time to help strangers with no expectation of return, Kawasaki has modeled a life philosophy centered on continuous improvement, authentic connection, and principled action. His legacy offers a compelling alternative to success narratives focused solely on wealth accumulation or status achievement, suggesting instead that a well-lived life integrates professional accomplishment with personal growth, family devotion, and social responsibility—all approached with a healthy dose of humility and humor.

About Author

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Guy Kawasaki

I was born in Honolulu, Hawaii in 1954. My family lived in a tough part of Honolulu called Kalihi Valley. We weren’t rich, but I never felt poor-because my mother and father made many sacrifices for my sister and me. My mother was a housewife, and my father was a fireman, real estate broker, state senator, and government official during his long, distinguished career.I attended Iolani School where I graduated in 1972. Iolani is not as well known as its rival, Punahou because no presidents of the U. S. went there, but I got a fantastic and formative education there. (Punahou is “USC,” and Iolani is “Stanford”—but I digress.) I pay special tribute to Harold Keables, my AP English teacher.He taught me that the key to writing is editing. No one in the universe would be more shocked that I have written ten books (or one book ten times) than Harold Keables.After Iolani, I matriculated to Stanford; I graduated in 1976 with a major in psychology—which was the easiest major I could find. I loved Stanford. I sometimes wish I could go back in time to my undergraduate days “on the farm.”After Stanford, I attended the law school at U.C. Davis because, like all Asian-American parents, my folks wanted me to be a “doctor, lawyer, or dentist.” I only lasted one week because I couldn’t deal with the law school teachers telling me that I was crap and that they were going to remake me.The following year I entered the MBA program at UCLA. I liked this curriculum much better. While there, I worked for a fine-jewelry manufacturer called Nova Stylings; hence, my first real job was literally counting diamonds. From Nova, its CEO Marty Gruber, and my Jewish colleagues in the jewelry business, I learned how to sell, and this skill was vital to my entire career.I remained at Nova for a few years until the the Apple II removed the scales from my eyes. Then I went to work for an educational software company called EduWare Services. However, Peachtree Software acquired the company and wanted me to move to Atlanta. “I don’t think so.” I can’t live in a city where people call sushi “bait.”Luckily, my Stanford roommate, Mike Boich, got me a job at Apple; for giving me my chance at Apple, I owe Mike a great debt. When I saw what a Macintosh could do, the clouds parted and the angels started singing. For four years I evangelized Macintosh to software and hardware developers and led the charge against world-wide domination by IBM. I also met my wife Beth at Apple during this timeframe—Apple has been very good to me.Around 1987, my job at Apple was done. Macintosh had plenty of software by then, so I left to start a Macintosh database company called ACIUS. It published a product called 4th Dimension. To this day, 4th Dimension remains a great database.I ran ACIUS for two years and then left to pursue my bliss of writing, speaking, and consulting. I’ve written for Macuser, Macworld, and Forbes. I call these the “Wonder Years” as in “I wonder how I came to deserve such a good life.”In 1989, I started another software company called Fog City Software with three of the best co-founders in the world: Will Mayall, Kathryn Henkens, and Jud Spencer. We created an email product called Emailer which we sold to Claris and then a list server product called LetterRip.In 1995 I returned to Apple as an Apple fellow. At the time, according to the pundits, Apple was supposed to die. (Apple should have died about ten times in the past twenty years according to the pundits.) My job on this tour of duty was to maintain and rejuvenate the Macintosh cult.A couple years later, I left Apple to start an angel investor matchmaking service called Garage.com with Craig Johnson of Venture Law Group and Rich Karlgaard of Forbes. Version 2.0 of Garage.com was an investment bank for helping entrepreneurs raise money from venture capitalists. Today, version 3.0 of Garage.com is called Garage Technology Ven

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