Skill, luck, and having a blast
This is going to sound obnoxious coming from somebody who went to a private prep school and an Ivy League college, but in the world of Jeopardy!, I was more of a Rocky Balboa than an Apollo Creed. I'm just a guy who likes the show. I don't follow all these message boards on how to wager for Final Jeopardy and Daily Doubles. I just love Jeopardy! And winning is far beyond anything; once you win Jeopardy! once, you can say "I'm a Jeopardy! champion" for the rest of your life. After the first game, I went backstage and told Maggie, "I won one. I don't have to do anything else now." And she was like, "Don’t say that! Go win more!" And so that's what I did.
I'll be the first person to admit that my wins were not terribly convincing. I had two games that I won in Final Jeopardy, where I got it right and the guy in first place didn't. I also had a lot of funny, Slumdog Millionaire-like moments. On the Thursday show, the category was "Islands" and the correct response was the Leeward Islands. The only reason I got it was because, when I was younger, I had spent some time sailing in the Caribbean and I was familiar with them.