Blogger Interviews: Will Leitch -- he wears pants

We're running a segment here at The Big Picture where we'll interview some of the biggest names in the sports blogosphere. What's the point? Well, these guys spend countless, thankless hours writing, so a little recognition from time to time is well warranted. Think of this as the blogger's version of a reach-around or something.

Joining us today is Will Leitch who is considered a pioneer in the sports blogoshphere. He's the editor of Deadspin, which is the most successful sports blog, well, ever. Leitch is also a published author, having penned the books Catch and Life As a Loser. We highly encourage you to check them out. (We've read Catch, which was incredibly entertaining. Haven't gotten to Life as a Loser yet, but plan to). Will looks a little something like this, but clothed looks more like this, seen here inquiring what Kordell Stewart is doing for dinner. Please help us in welcoming Will, and behave yourselves in the comments.

1. The rundown:

Name: Will Leitch
Age: 31
Location: Brooklyn, NY
Occupation: Editor, Deadspin.com
Favorite team: St. Louis Cardinals, Arizona Cardinals, Illinois Fighting Illini
Links to your favorite all-time posts you've written. (3-5)
Pretty much anything involving Carl Monday, which I will confess is my favorite story on the site.

2. Take us through a typical day of blogging for you.

Well, I wake up at 7 a.m. and start digging in. The first post goes up at 8:45, and they’re spaced out throughout the day from there. I take a break about 2 p.m. and go to the gym, because no one’s ever at the gym at 2 p.m. I live alone, not in my parents’ basement, and I do wear pants.

3. A lifetime ago, you worked as a sports reporter. We suspect there are some aspiring journalists reading this who'd give their left leg for a job at a major newspaper or sports magazine. If you will, please take us through your career starting at your days in Champaign. So, we're curious about internships, first jobs, etc.

Well, when I went to the U of I, I spent every day at the Daily Illini; I was one of those annoying lifers who was a part of the newspaper clique that no one else could enter. (Sorry.) I covered the basketball and football teams for the DI and the St. Louis Post-Dispatch, and then I moved to Los Angeles to work as a film critic for a year. (Which, deep down, is still probably my dream job.) I moved to St. Louis to work for The Sporting News for a year and a half, and because I’m a pretentious schmuck, I packed my bags and headed to New York in January 2000 to Be A Writer. After odd jobs ranging from working as a Web producer for The New York Times On The Web to being a secretary for a doctor, I eventually started The Black Table with some friends of mine, and that ended up leading to Deadspin. I’d always worked as a journalist, but found it frustrating. Not the work; I always loved the work. It was just difficult to get anyone to read it.

4. When, why and how did you get out of traditional sportswriting? Did you have the job at Deadspin lined up at this point, or were you facing unemployment? Also, traditional sportswriters have to deal with these little filters we've come to call editors. How liberating is it writing without a filter?

Oh, I have a filter; the readers are the best possible editors, because they call you on your shit immediately and in the most public possible forum. It makes you be on your game all the time, which is exhausting but absolutely worth it. I had been out of “traditional sportswriting” for a while when I started Deadspin. I was actually covering Wall Street for a trade publication called Registered Rep., and still doing The Black Table of course.

5. Take us through how Deadspin was created. You approach Gawker? They come to you? Meet in the middle? Sleep with the upper management? Did your work at The Black Table factor in at all?

Yeah, the BT was the main factor; they had seen my work over there and we were all trying to figure out a way to do something together. (I’d like to note that all four BT editors, all of whom were working boring trade pub jobs when we started it, have great gigs now. Eric Gillin is at Esquire, Aileen Gallagher is at New York Magazine, and … well, I’m a blogger. There’s three of us doing well, anyway.) They had approached me about doing Oddjack, the gambling site AJ ended up doing, but my dirty secret is that I don’t like gambling on sports and figured that made me a terrible candidate. So I wrote up a long proposal to sell them on the idea of a sports site. They were initially skeptical, but I gave them enough alcohol to the point that they finally gave in.

6. OK, so Deadspin comes into existence. How the hell did it have so much success at first? The content obviously speaks for itself, but still, how'd word get out initially? And a piece of advice, if you will, for some smaller sites how to build a steady readership.

Honestly? It was just like any other site. Gawker didn’t put out some big publicity rush or anything. Basically, they told us that we were on our own. Having seen Oddjack struggle -- despite AJ’s excellent work there -- I knew that I couldn’t count on them just giving me unlimited rope. It’s not an art project. So I just figured I’d do my best to kick ass at it every day and hope people eventually noticed. It helped that I was posting more every day than anybody else was. I had that advantage. Because there hadn’t been that many sites like that up to that point, people started noticing. SI did a story on Deadspin, and then the Times, but those really weren’t huge traffic spikes initially. The whole thing grew mostly organically, which is really the only way to do it. You have to be patient.

7. Dream job? Go.

Being able to wake up every day and write about whatever the hell I want. So not that far from what I have right now, I’ll confess.

8. "You're with me, Leather." Ever think that was going to take off the way it did?

No way. When you look at the early posts, I almost downplayed it too much. In retrospect, it should have been obvious; it’s the perfect tweaking-ESPN catchphrase. Someone told me the other evening that they had no idea that “You’re With Me Leather” originated on Deadspin. They just thought it had been around forever. That’s just amazing to me.

9. There are all sorts of wonderful blogs out there. A few you'd recommend?

Agh, just so many. I really can’t narrow them down; it would be like asking which type of food I would recommend. There’s something for every taste.

10. Any interesting job offers after building yourself up as a top blogger?

A few, but none that would be even remotely as much fun as this is.

11. Most rewarding parts of blogging? Most frustrating?

I really don’t get frustrated by anything anymore. This is an unbelievable opportunity, and I try to keep it in perspective. Some people get really worked up when the “mainstream” media takes one of their stories and doesn’t credit it, but it just doesn’t get me too riled up. I mean, the site is founded on not taking sports too seriously. That extends to the site as well. I mean, it’s a blog. It’s hopefully funny and can hopefully shed some light on the world of sports, but you can’t get carried away. Like sports, it’s supposed to be fun, and it is. It can, however, wreak havoc on one’s personal life. I’ll admit to that.

12. We'll get you outta here on this: There's this little football game about to be played in Miami. Give us a winner and also a player who's bound to get into some mischief on South Beach.

I think the Colts are going to win…and Jim Sorgi is totally gonna get arrested with crack.

(Past interviews; also found on right sidebar: Dawizofodds; Matt Ufford; The Mighty MJD; Jamie Mottram; The Big Lead; The Cavalier).