Guy was born in Honolulu, Hawaii in 1954. His family lived in a tough part of Honolulu called Kalihi Valley. They weren’t rich, but he never felt poor because his parents made many sacrifices. His mother was a housewife, and his father was a fireman, real estate broker, state senator, and government official during his long, distinguished career.
Guy attended Iolani School where he graduated in 1972. Iolani is not as well known as its rival, Punahou because no presidents of the U.S. went there, but he got a fantastic and formative education there. (Punahou is “USC,” and Iolani is “Stanford.”) Guy owes his writing career to Harold Keables, his AP English teacher. Keables taught him that the key to writing is editing. The fact that Guy has written thirteen books (or one book thirteen times) would shock and delight Harold Keables.
After Iolani, Guy matriculated to Stanford. He graduated in 1976 with a major in psychology which was the easiest major he could find. After Stanford, Guy attended the law school at U.C. Davis because, like all Asian-American parents, his folks wanted him to be a doctor, lawyer, or dentist. He only lasted one week because he couldn’t deal with the law school teachers telling him that he was crap and that they were going to remake him.
The following year Guy entered the MBA program at UCLA. He liked this curriculum much better. While there, he worked for a fine-jewelry manufacturer called Nova Stylings; hence, his first real job was counting diamonds. From Nova, its CEO Marty Gruber, and his Jewish colleagues in the jewelry business, Guy learned how to sell, and this skill was vital to his career.
Guy remained at Nova for a few years until the Apple II removed the scales from his eyes. Then he went to work for an educational software company called EduWare Services. However, Peachtree Software acquired the company and wanted Guy to move to Atlanta. “I don’t think so” was his reaction because he couldn’t live in a city where people call sushi, “bait.” Luckily, his Stanford roommate, Mike Boich, got Guy a job at Apple. So one could make the case that Guy owes Mike everything. When Guy saw what a Macintosh could do, the clouds parted and the angels started singing. For four years Guy evangelized Macintosh to developers. He also met his wife at Apple during this timeframe–Apple was very good to Guy.
Around 1987, Guy’s job at Apple was done because Macintosh had plenty of software by then, so he left to start a Macintosh database company called ACIUS. It published a product called 4th Dimension. To this day, 4th Dimension is a great database.
Guy ran ACIUS for two years and then left to pursue his bliss of writing, speaking, and consulting. He wrote for MacUser, Macworld, and Forbes. Guy calls these the “Wonder Years” as in “I wonder why I deserve such a good life.” In 1989, Guy 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. They created an email product called Emailer and then a list server product called LetterRip.
In 1995 Guy 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.) Guy’s job on this tour of duty was to maintain and rejuvenate the Macintosh cult.
In 1997, Guy 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 Ventures; it is a venture capital firm and makes direct investments in early-stage technology companies.
In 2004, Guy worked at Garage and then he began writing and speaking. Eventually he started another company with Will Mayall and Kathryn Henkens. This company created a website called Alltop–for “all the topics.” It aggregates RSS feeds and organizes them into topics such as photography.alltop.com, Macintosh.alltop.com, and social-media.alltop.com. It also publishes human-interest stories that elicit the reaction, “Holy kaw!”
Then in 2013, Guy became a special advisor to the CEO of the Motorola division of Google. In 2014, Guy resurrected the title “chief evangelist” and joined a Sydney-based company called Canva. This company provides an online, graphic-design service. Its goal is to democratize design. If you need graphics for social media, flyers, posters, infographics, business cards, or book covers, check it out.
In 2015 Guy was appointed to the board of trustees of the Wikimedia Foundation. He joined Wikimedia in order to help democratize knowledge.