Career Do-Over: Interview with Serial Entrepreneur Guy Kawasaki

By J.T. O'Donnell Guy Kawasaki is a serial entrepreneur. What's that? It's a person who has started several successful start-ups. What I love most about Guy is that he isn't afraid of sharing his secrets to success. He's honest and funny (when you read his answers you'll see what I mean). While others might want to keep their insights close to the vest, Guy shares and gives daily to his followers via Twitter and his blog, which is called, How to Change the World. In fact, Guy was one of the first people I ever followed on Twitter. I learned about him through his latest venture,, a site that lists the best blogs by category. is like an online magazine rack and I highly recommend it as a place to look for insightful resources - especially, when it comes to your career. CLICK HERE to visit Alltop's Career Section. Here's what Guy had to say about his own career: 1) What did you study in college, and then, knowing what you know now, do you wish you had studied something different? If so, what would it be and why? I tried to be a pre-med, but I fainted during a tour of the Stanford Medical Center--I am not making this up. Plus, I couldn't handle all the math and physics courses that doctors need to take for God-knows-what reason. In my quest for an easy major, I found psychology, and the rest is history. With hindsight, maybe I should have majored in computer science so that I could know when entrepreneurs are bull shiitake-ing me although it's not clear that I would need a computer science background since entrepreneurs are lying whenever their lips are moving.
2) Tell us your career journey post-graduation through now in less than 200 words. Then tell us: If there was one thing you could do differently in that journey, what would it be?
After graduating with a psychology (not pre-med major) from Stanford I "attended" the UC Davis School of Law for only two weeks because I just couldn't stand it. I may be one of its most famous almost-alumni! Maybe if I had stuck to pre-med, House would be based on me. Or Denny Craine if I had been a lawyer.
After that, I went to UCLA to get an MBA. I got into UCLA and Northwestern, but my mama didn't raise no fool and below zero winters weren't in the cards for me. While at UCLA I worked part-time counting diamonds--literally counting diamonds. While my buddies went into investment banking and consulting, I stayed with this jewelry manufacturing firm and got the greatest lesson in selling that a person could. Much of my success is because I learned how to sell in the jewelry business--not to mention my command of Yiddish. From the jewelry business I went to Apple after a short stint in a software company. It was short because the company was acquired, and it moved to Atlanta. Atlanta held as much appeal to me as Evanston, Illinois, so I went to Apple because of nepotism (that is, my college roommate hired me), started a few software companies, went back to Apple, started Garage Technology Ventures, and also created an "online magazine rack" called Alltop. Oh yeah, in 1994 I turned down the opportunity to interview for the CEO position of Yahoo. That was a $2 billion mistake. Are you sure you want to interview me? 3) Name 1-2 things you've learned to date about career that you think young professionals (ages 18-40) would want to know. 1) Your first few jobs after college don't really matter so chill out. You're aren't going to stay at these jobs very long unless you are total suckup who wants to be the youngest--albeit miserable--partner in some New York firm. I didn't exactly plan to go from counting diamonds to funding tech startups if you know what I mean. 2) Ultimately, if you're living right, kids will bring you the greatest joy in life. Certainly, your greatest joy will not come from money, houses, cars, boats, whatever. In fact, I could make the case that all of these are barriers to true joy. At the end of the day, you really should do what you love to do not what makes the most money. Guy Kawasaki is a founding partner and entrepreneur-in-residence at Garage Technology Ventures. He is also the co-founder of, an ³online magazine rack² of popular topics on the web. Previously, he was an Apple Fellow at Apple Computer, Inc. Guy is the author of nine books including Reality Check, The Art of the Start, Rules for Revolutionaries, How to Drive Your Competition Crazy, Selling the Dream, and The Macintosh Way. He has a BA from Stanford University and an MBA from UCLA as well as an honorary doctorate from Babson College.