While many entrepreneurs and financiers boast fancier pedigrees, Guy Kawasaki still is a head-banging bruddah from a tough blue-collar neighborhood in Honolulu.
As a high school football linebacker, he slammed running backs to the turf. In hockey pickup games in Silicon Valley, he hammers opponents to the ice. And since gaining fame in the 1980s as Apple's "chief evangelist," he's earned his battle scars as a survivor in the technology realm.
"What I lack in talent, I compensate with my willingness to grind it out," says Kawasaki, flashing a huge grin. "That's the secret of my life."
Kawasaki brings his gung-ho Hawaiian spirit and laid-back generosity to technology, says Neenz Faleafine, chief evangelist at Alltop, a news aggregation website co-founded by Kawasaki.
"Guy's roots are still a part of his character and personality," she says.
Kawasaki, whose new business book, Reality Check, was released last week, is:
•An entrepreneur. His company, Nononina, last spring launched Alltop (www.alltop.com), an "online magazine rack" of sorts that lists popular websites and blogs by subject, from "Music" to the "World of Warcraft" online game.
•A venture capitalist. As managing director of Garage Technology Ventures, he makes investments up to $3 million in technology start-ups in Western states.
•A marketing machine. He's a globe-trotting speaker, author of the best-selling The Art of the Start and eight other books and a blogger who writes the popular How to Change the World blog (http://blog.guykawasaki.com).
In Reality Check, Kawasaki aims to show entrepreneurs how to learn from his failures. Kawasaki, 54, says that most executives write "glamorous biographies" that hail their successes, while ignoring their blunders. Not him.
"Reality Check is not about what Guy did well, trust me," he says. "I'm going to help a lot of entrepreneurs from making the same mistakes."
An expensive error in judgment
Look at his ill-fated Yahoo episode — one of his many investment boo-boos, he admits. When Yahoo was a tiny start-up in the late 1990s, venture capitalist Michael Moritz of Sequoia Capital, one of Yahoo's original investors, asked Kawasaki if he wanted to be CEO of the Silicon Valley firm.
Kawasaki was skeptical. He couldn't see how Yahoo's business model would generate revenue, and he declined the offer.
"I'd say that was a $2 billion or $3 billion mistake," Kawasaki says in his Palo Alto office, a short walk from Stanford University. "Now Michael doesn't call me. I can't say I blame him."
Moritz goes easier on Kawasaki, noting that no advertisers had spent a cent on Yahoo at the time. Moritz e-mails: "Guy didn't blow it — he understandably chose different paths" in his life.
Kawasaki often takes the offbeat path. Rather than study medicine or engineering like a good Asian-American kid, he earned a Stanford psychology degree and an MBA from UCLA. Hoping to please his folks, he enrolled in law school at U.C.-Davis, but hated it and dropped out.
At Apple, Kawasaki marketed the underdog Macintosh computer to hardware and software developers, who favored IBM's dominant technology. While Steve Jobs co-founded Apple, many credit Kawasaki for boosting the Mac's popularity and creating the cult of Apple, whose devotees still flock to flashy MacWorld shows to hear Jobs speak.
"Guy turned that into a reality," says Kyle Mashima, a former Apple manager and Stanford friend.