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An Average Traveler

I was born in Hollywood, Calif. — truly a shocking notion if you know how unstruck I am by stars.

My father was a trial lawyer. He taught me the power of articulate persuasion. We’d sit at the dining room table and take sides of a debate. He would argue me into a corner, then at some point say, “Switch,” and I’d have to defend the opposite position. He would then deftly argue himself out of the corner he had just painted me into.

My mother had multiple sclerosis. By the time I was 13 she was in a wheelchair, and she was bedridden when I went to college. She passed away in 1986. A huge responsibility fell to me at an early age as the oldest of three kids. I balanced the household checkbook at 13. I had a special driver’s license at the age of 15 to take my siblings around.

I picked up fencing in high school partly because it attracted the craziest bunch of people. I helped start my high school team, recruiting students with the pitch, “Wouldn’t it be fun if you learned how to stab your friends?” I went to the Junior Olympics when I was 16 or so and lost every one of my bouts. But I got better. When I went to Harvard I made the varsity team, was later elected captain, and in 1983 won a slot on the collegiate All-American team. In fencing, you have to think three moves ahead. It turned out to be good training for corporate life.

I went to Harvard thinking I would major in physics. I liked the pulleys-and-levers part but not the extensive math. Computer science was a bit of a backwater of academia then, but I liked the game of solving programming problems. I’d be pumped at 3 in the morning when I found bugs in programs.

In 1985, after I had graduated from college, I was co-founder of a company called CenterLine Software, which made programming and testing tools that we sold to software developers. In 1998 the other owners and I sold half the assets, and the other half became CenterLine Development Systems, which was headed by my wife, Caroline.

That same year, Caroline and I were planning a vacation in Mexico, and I started looking online for unbiased opinions about a particular hotel. What I got was a thousand sites showcasing exactly the same gorgeous picture and the very same descriptive paragraphs.

It took a lot of time, and some advanced Boolean logic in my search queries, but eventually I found a write-up from a couple who’d stayed at the hotel I had in mind, with pictures that showed rusted chairs and a beach not up to our expectations. I had dodged a bullet.

Later Caroline suggested I build a Web site to help other travelers in similar situations. “Just keep it easy to use and honest,” she said. TripAdvisor and its other Web sites now attract more than 75 million monthly visitors...