Online Extra: Chicago Dropout Makes Good

G2 SwitchWorks' Alex Zoghlin left high school to start his own business back in 1988. It didn't go so well, but there's no stopping a serial entrepreneur

Alex Zoghlin, founder and chief executive of G2 SwitchWorks, runs a pretty egalitarian place. The startup, which produces flight-booking software for the travel industry, does have individual offices in its headquarters on the 39th floor of the Sears Tower in Chicago. But they're either empty or function as conference rooms. Instead, everyone works in an open environment in low-walled cubicles, including the boss.

Zoghlin's own work space is a mess, with papers and folders covering almost every square inch of his desk. He has a couple of framed photos of his wife and their three young daughters, but they're laying face up amid everything else. He also has a copy of John Welch's best-selling memoir, Jack: Straight from the Gut. Zoghlin is an omnivorous reader. He says it's how he gets ideas for new businesses.

Zoghlin, 36, excuses his sloppiness by pointing out he's hardly ever in. He logged 24,000 miles in January alone, flying coast-to-coast to make sales pitches or to meet with directors or clients of his 18-month-old company. His mother, Cari, might approve -- she's a travel agent. So might his pals at his previous company, Orbitz. Zoghlin was the travel Web site's first employee and chief technology officer.

Just back from a G2 SwitchWorks board meeting in San Francisco, Zoghlin took a good part of an afternoon to talk with BusinessWeek Senior Correspondent Michael Arndt. Among the topics: His decision to quit high school when he turned 18 to try his hand at business, and how that led to a four-year hitch in the U.S. Navy. An edited transcript follows:

Tell me about your background.

I'll give you the sordid story, it's probably all on the Internet anyway. I grew up in the suburbs of Chicago, in Wilmette, Ill., the youngest of four kids. I went to New Trier High School. Debate took up a big part of my life, and at the beginning, I think I went undefeated for a few years. I was also in a rock band, playing keyboards.

My grades were bipolar: I believe I only received A's or F's. A's if I made it to class, F's if I didn't. I wouldn't go to school very often. Most people cut class to go smoke cigarettes. I cut class to stay home and play with the computer. It's kind of embarrassing now that I say it in public. I was actually president of the student body at New Trier my senior year, and then in February, 1988, I dropped out. I guess I'm impressed I made it that long.

What was your parents' reaction?

They flipped out. We stopped communicating for a year, I think.

What did you do next?

I started a computer-software company. This was the time when typing pools were just getting replaced by computers. I saw a good opportunity to build automation products for, in this case, law firms, which have to maintain lots of records.

I didn't have a lot of training in business, but my dad had always been an entrepreneur -- he had a benefits and pension planning consulting business that at one point had a couple of hundred employees -- so I probably learned the fearlessness from him.

I made a good run at it. I worked on a billing system for a large law firm that will remain nameless. I tried selling the system to a second law firm and got sued by the first firm for contract infringement. As an 18-year-old dropout who was up to his gills in loans, there wasn't a lot of recourse for me.

What happened?

I was out of business. I was licking my wounds at my house one day when I got cold-called by a recruiter from the military. They must have a list of dropouts. I laughingly said, "Give me a lawyer and we can talk." He said, "Funny you should say that, but we can actually get your lawsuit put on hold if you go into active duty."

It was either that or go back to my dad, which I was too stubborn to do, so I joined the Navy and did four years of active duty. You get to choose what you want to do in the Navy. I chose cryptology.

As I said, I had stopped communicating with my parents. I think I was in the military a year when I finally figured out this was really dumb. I had a lot of years left in my life and it was really stupid not to communicate with the people you love. I wrote them a long letter, and that was it. My dad was also ex-military -- Navy as well. I think the military was a great, great experience for me.

How did you get so knowledgeable about computers at such a young age?

My dad -- his first name is Gilbert -- always had computers in the house, starting out with a mainframe terminal and a modem on top that you put the phone into. So when he would go to work, I would sneak in -- I had memorized the numbers that he had pushed to get on the system -- and play online Star Trek. I was in that very early group that had a computer from the age of 3 on. I think it becomes a natural extension of you after a while, it becomes part of your DNA. I was very lucky.

Since your first business disaster, you've gone on to start four businesses. How's your role different here than at Orbitz or your previous ventures?

It hasn't changed that much. My role is primarily cheerleader. My job is to take the bureaucratic obstacles out of the process as much as I can. My job is, and always has been, to hire people who are significantly smarter than I am.

Your previous businesses, except for the first, have been successes, too. What attributes do you have personally that have enabled you to succeed?

I wish I had a great sound bite for you. A lot of people are technically competent, but they don't see how the technology is applied in everyday life or in business. Then you have people who are really good in business and finance, but they don't understand technology. I'm really lucky, I can connect the dots to both.

You don't stop learning when you leave school. I read a significant amount -- I've been made fun of because of all the business books I read. But you take from what works and try it in a new setting. I've had many great mentors, including my dad. My ears are never turned off. It also takes a lot of work. I have a terrible genetic defect that when I start a business, I spend all of my waking time, day and night, thinking about the business.

What would you do if one of your daughters dropped out of high school?

If one of my daughters took a page from me, it would mean that a whole lot of other decisions were not made very well, and I didn't learn from my mistakes. Like everything else in life, I would assess the situation and make the best of it. Who knows, maybe she would start the next Microsoft.

My middle daughter, Zoe, already is trouble. She's 3 years old. She's extraordinarily strong-willed -- she would rather have her way than have ice cream. My dad is always telling me: "She is you, and this is payback."

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