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Q&A: Bill Simmons (cont.)

Posted: Wednesday March 22, 2006 5:40PM; Updated: Monday March 27, 2006 1:39PM
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SI: Interesting. When you say it was your dream, what do you mean?

BS: There's a whole generation of guys who were normal people who liked sports who wanted to go into it because these sportswriters were our heroes. We didn't know these guys were maniacs, for the most part.

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SI: So you must have been aware of their response when you first started writing. What was it like?

BS: I think back to 1998, when I had my own column, and it was dismissive, like, "Oh, he's on the Internet." It was an old guard/new guard thing. As it went along, I found that people who are in visible places now -- like you, for instance -- you actually read my piece and you have an opinion on it. Back then, it was a different age range, and they weren't prepared and they didn't know how to get online.

I didn't have any credibility, basically. I don't know if I have credibility now, but at least people have read me. That's the biggest way the Internet has changed. I'd tell people, "I have a column, I write on America Online," and they'd look at me like I had three heads. "Oooh, the Internet, do they pay you?" Like I was working on a pyramid scheme. Gradually that changed.

There were a couple bad years in there. People would cut and paste my column and nobody would know I wrote the column. My friends back then would get columns [forwarded to them] and say, "You have to read this column!" And there'd be no name, but it would be my column! It would drive me crazy.

SI: How did you get involved with AOL? Did you contact them?

BS: They had this Digital City set-up. They were trying to make an electronic newspaper. They had this Movie Guy, who did movie reviews. I'd given up on bartending and thought the only way to get into writing was to work on one of the two newspapers, work for the weekly or try to get a job at SI, and there was no Plan E. What do you do if you're a 25-year-old wannabe sportswriter? Where do you go? You have no options.

This guy on Digital City was called Movie Guy. I said, Wow, I want to do a sports [column] like this guy and I don't care what you pay me. I think the first month I made $50 a column. At the last second, I decided to call it Sports Guy, which made sense because the other guy was Movie Guy. You could only get it on AOL.

I used to forward the column to my friends, and people would e-mail and ask if I could put them on my mailing list. Eventually it was people I didn't know, and I'd send it out to 100 people. That's a lot of how it was the first 18 months. And then we were available on the Web in November 1998. That changed everything.

To me, the biggest thing that happened was when Peter Gammons went to ESPN.com full time. Until then, there was a stigma that people at newspapers would say, "Oh, they're on the Internet." People like my dad didn't know how to navigate the Web. When Gammons went to ESPN.com, it was like the top baseball information guy was on the Web and you had to go online to read him. So you had to figure out how to go online and type in www.espn.com or you wouldn't read him. And that's when I knew I was going to at least make it at some level.

Up until the winter of 2000 I was thinking about maybe quitting and going into real estate. My stepdad is in real estate and it got to the point where I was in my late 20s, I'd never made more than $30,000 a year and there was no money in sportswriting at all. And at some point you've just got to give up and have a life and I was definitely getting there. Which was frustrating, because I knew I could do this. Even in college, I knew I wanted to write a column. I knew I could do it. Basically, my first eight years out of college, I wasn't allowed to do it.

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