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Interview with Bill Simmons, Author of The Book of Basketball

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It is not hyperbole to say that Bill Simmons, aka The Sports Guy, is probably the most popular sportswriter in the country. And he got there via a path that, in the 1990's, was unconventional to say the least: he found an audience on the Internet. Simmons launched his "Boston Sports Guy" column on the web in 1997, following a stint at the Boston Herald. Since then, Simmons has cemented his place as one of ESPN.com's featured columnists and one of the most unique voices in our culture. For the twelve readers unfamiliar with his work, Simmons mixes a pure love of sports (often with a slant towards his hometown of Boston), while possessing the biggest infatuation with pop culture this side of "I Love the 90's" (which Simmons has appeared on). Writing from the voice of the common fan (with a vantage point from his home rather than the press box), Simmons has inspired numerous imitators, drawn the ire of sports icons like Elgin Baylor and Isiah Thomas (as a Knicks fan I consider that something to be proud of), while proving that an intimate knowledge of "Beverly Hills 90210" does not preclude a successful writing career.

Simmons's first book, Now I Can Die in Peace, a collection of columns about the years leading up to the 2004 Red Sox World Series title, was a New York Times bestseller. A former writer for "Jimmy Kimmel Live," he is currently serving as executive producer of ESPN's "30 for 30" documentary series, and runs the B.S. Report podcast where he has interviewed everyone from Chuck Klosterman to NBA Commissioner David Stern to "Mad Men" star Jon Hamm. Bill's new book, The Book of Basketball (which Amazon's editors call, "A 700-page work of hoops genius that would make Dr. James Naismith beam proudly -- and probably blush.") will be released on October 27. His ESPN.com page can be found at The Sports Guy's World, his Twitter page at Twitter.com/sportsguy33 and his personal site can be reached at Sports Guy Unplugged.

JP: You've talked about your struggles as a young, aspiring sportswriter and how entrenched veterans among other issues made it impossible for younger writers to make their mark. If you had started 10 years later, with the newspaper industry in the state it is in today, how do you think your career would have been different?

BS: I graduated college in 1992 and didn't reach a sizable audience with my column for nine solid years. If I had started ten years later, or ten years sooner, everything could have happened sooner obviously. But if I had started fifteen years later? I don't know. Younger writers gravitate towards blogging and I'm not sure that would have necessarily been a good thing for me. You don't have to work at building an audience because, really, you can get a wad of traffic from established blogs right away with just one post. You're training yourself to think in shorter, more immediate bursts into putting real thought into what you want to say. And you're reading other bloggers constantly, which isn't necessarily the best way to get better as a writer.

When I was younger, I was something of a journalism/book/short story junkie and read every conceivable type of writer. I had hundreds and hundreds of books; I had every issue of Sports Illustrated and Inside Sports since 1974; I had two decades of clippings from GQ, Esquire, The National, New Yorker and other places saved in manila folders. Now, if there had been an internet back then ... would I have done all that? Probably not. I would have been surfing the 'net all day like everyone else.

And again, it's dangerous to have the ability to get an audience instantly. I started my old web site in 1997, when there wasn't the quid pro quo system of "I'll link to you if you link to me." I needed to bring readers to my site every day -- knowing that I wasn't getting traffic from other places -- and the only way that was happening was if I pushed the envelope and wrote angles that I wasn't seeing anywhere else. That constant fear of "I need people to keep coming back!" made me better in the end. So I was lucky and unlucky, if that makes sense. Remember, I gave up on writing in 1996 and nearly again in 2000 because I was so freaking frustrated, I wanted to strangle somebody. That can't be a good career path.

JP: At first you were vehemently opposed to the concept of Twitter. It's safe to say you've come around on it. What changed your mind? And do you feel like Twitter offers something that your columns, podcasts and books do not?

BS: I didn't understand Twitter. I thought it was a place where Shaq let people know that he just ate a hot fudge sundae or something. Really, it's the opposite: it's a media/marketing vehicle disguised as a social network. What other place can celebrities, writers, athletes, talk shows, music bands, companies and everyone else connect immediately with fans and/or consumers? I started my Twitter account for selfish reasons: I wanted to have a place to post updates on my book signing tour and stuff like that. I never realized that I'd have so much fun tweeting. It's become the deleted scenes for my DVD of columns and podcasts. For moments with a shelf life -- say, the Red Sox winning on a walkoff grand slam -- it's the perfect place to comment on something that probably wouldn't be saved for a column. And you know what else? It's helped my writing a little because it's a challenge to craft jokes within 140 characters -- gets your brain cells going all the time -- and I'm competitive so I like messing around with that. For a columnist like me, Twitter is like having a putting green: useless and helpful at the same time.

JP: The Book of Basketball clocks in at 700 pages. Was your plan to always write such a long book, or was there a point where you just said, "Screw it, this book needs to be 700 pages?"

BS: The original plan was just to blow up the Basketball Hall of Fame and reconstruct it like an Egyptian pyramid, with five levels, then figure out which players belonged in what order. As I started throwing myself into it, I realized that there was no real way to compare players from different eras without a common theme in place. So the quest shifted a little: what's that common theme? Is there a specific way to figure out why some players are greater than others that doesn't just involve stats? Why do some players end up getting underrated/overrated over time? As I was trying to figure THAT out, I realized that -- of all the sports, by far -- race plays the biggest role in the NBA, and in many cases, specifically affected either someone's career or the way we remember something as fans. So I became obsessed with that. And as I was trying to figure THAT out, I realized that there just weren't any books about how the NBA came to be.

Anyway, that's when I said, "Fuck it. I'm just going for it." I didn't care how long the book was, just that everything tied together. And it did. I really hope people aren't intimidated by the length. It's not a novel. You can jump in and out at any time. There are a ton of footnotes (that's one of the reasons the book runs long), and we didn't cram each page with words, so it reads much easier than you'd think. If you like my columns, you're going to enjoy the book. At the very least, it's a book that you can stick next to your toilet, read 5 pages at a time and finish five months from now. It will be the best five months of dumping you've ever had. Your colon is going to love this book.

JP: Your first book was a collection of columns (with enough footnotes to pacify even the most hardcore David Foster Wallace fans). This is your first book of primarily new material. What made this the right time to write this book?

BS: Well, it's about 75-80% new stuff and 20-25% stuff you have seen in some form. With more dick jokes. And I get to drop some F-bombs and make fun of announcers. And there are even more footnotes than I had in the last book; they work even better this time around. You get Network Simmons on ESPN.com; this is HBO Simmons except you don't get subjected to a gratuitous shot of my ass. Anyway, this was the right time for me as a writer more than anything. Writing is like playing golf - you have to keep working at your swing. I had been in a slight rut with the same deadlines on the same days for a little too long, and on top of that, I was constantly battling with ESPN over content in my columns. So the book was a liberating experience for me: no deadlines, no restrictions, nothing. It made me remember why I liked writing so much. At the very least, you will read this book and think, "That dude enjoyed working on this thing."

JP: What are the differences -- emotionally or otherwise -- between handing in a column and finishing a book? And what have your experiences in the world of publishing been like?

BS: I always hand things in begrudgingly and wish I had an extra two hours with the piece, so I loved working on the book because those two extra hours were always there. I could keep tinkering with chapters and trying different things. One problem: when it came time to hand the book in, that "I just need two more hours" feeling became "I just need two more weeks." It made me equally miserable. The good part was that it got me in the habit of writing every day again, which is the best thing any writer can do. I am one of those people that does everything last-minute, so in a way, a book deadline is better for me than a column deadline because you can't write a book last-minute. It's impossible. As for the publishing world, book companies are even more rigid than ESPN, which I didn't think was possible. Ultimately, it's like anything else: Trust yourself with the things you know how to do, and trust the big company on everything else. It was a little rocky at times. I kind of wish there had been cameras in the Random House offices when they found out that the book was 700 pages, just for comedy's sake. But that's the book I wanted to write, and eventually, they accepted that.

(Of course, long after I finished it, they sent me an advance copy of the hardcover and I was like, "Wow... now this is why you get a big-ass book company to do your book." It looks beautiful. It's laid out perfectly. So easy to read. I just love it. I want to just take it to parks, sit on a bench and stare at it. They did a great job. This is why you get big-ass companies to do your book.)

JP: You once said that one of the biggest things that happened to you was (Hall-of-Fame sportswriter) Peter Gammons starting to write for ESPN.com, because in essence it gave credibility to people whose writing appeared online. Do you feel completely validated, or is there a part of you that wishes you'd had a chance for a newspaper career?

BS: Totally. Before Gammons, when I told people that I wrote sports columns on the internet, they'd look at me like I had just told them, "I trade vintage porno VHS tapes." Gammons made people over forty like my dad -- people who didn't understand hyperlinks or any of that crap -- to say, "Wait, GAMMONS is online? Maybe I need to figure out this internet thing."

Anyway, I didn't accomplish one dream (writing a column for the Globe) but realized another (succeeding with a national sports column that ran 2-3 times a week, which nobody had ever done before). So I think those two things cancel each other out. I am semi-validated. Yes, I always wanted to write a column for the Globe. But if you flip it around, really, I wanted a column there because the Globe had the most readers. It had nothing to do with the Globe itself. For the last eight-plus years, I've been writing a sports column for the sports web site that has the most readers. Same dream, just realized a little differently.

(Note: All of this is total bullshit. I am still pissed that I never wrote a column for the Globe while newspapers were alive. Now it's too late. Fuck. Thanks for bringing this up.)

JP: John A. Walsh (Executive Vice-President and Executive Editor of ESPN) once said of you, "He would not have had his voice in a traditional medium. His entry point allowed him to be himself." With the decline of newspapers and onslaught of blogs, many writers are eschewing 'traditional' journalistic training. Do you feel this path is beneficial to aspiring writers?

BS: With all due respect to Walsh, who's my mentor, I disagree. I could have found that voice in a traditional medium; it's just that the medium was too traditional to ever give it a chance. You were only supposed to succeed by writing exactly like everyone else. I like that about the internet - there's no "accepted" style now. If anything, you're better off NOT writing like anyone else. The basics for aspiring writers are still in place: read as much as possible, figure out what's working for writers that you like, work at a style that combines all of those things, keep writing, keep reading, never settle for being average, and don't just say what you think but say it in a way that's fun to read and is constructed in a thought-provoking way. If you're an aspiring writer and want to blog and settle for immediacy/quantity, that's fine. Knock yourself out. That might be the right choice for you. Really, there's no right answer. It depends on the person.

I just think it's too early to say whether journalism is dying. I'd like to think that it's more alive than ever in a lot of ways. As we covered earlier, 24 year old me couldn't have gotten read in 1994. In 2009, 24 year old me could find an audience pretty quickly.That's not progress?

JP: You toured for your first book back in 2005 and will be touring for almost an entire month for The Book of Basketball. As you know, writing is a pretty solitary endeavor. Is it hard to go from the relative privacy of writing/podcasting to touring non-stop for weeks?

BS: I love it. Being a writer sucks. It's a solitary endeavor. My last tour was one of the highlights of my life. I loved meeting readers, going to different cities and everything else. And my signings are a little different: I don't have my head down just signing my name. I actually like talking to people and writing whatever they want me to write in their book. I had some four-hour signings the last time. I can't imagine doing it differently. I mean, I was a bartender/waiter 12 years ago. If you had told me in 1997 that even 5 people would be waiting online for me to sign my new book in 2009, I would have jumped around like Joe Carter in the 1993 World Series. I love it. I can't imagine why anyone wouldn't like it. The only thing I worry about is Karpal-Tunnel Syndrome -- my last tour almost caused it. I'd hate to cancel any cities because I had to fly to Alabama to consult Dr. James Andrews on tour-ending surgery.

JP: As of right now, you're a columnist, author, podcaster and now, as one of the executive producer's of ESPN's "30 for 30" series, in the TV biz. Are there any other media outlets you plan on taking on soon?

BS: You mean, besides porn? I don't know. I always wanted to create a TV series. I thought I pulled it off with something I wrote in 2007 for HBO, only they killed it, and right after they killed it, everyone who killed it got fired for being bad at their job. So does this mean I can't create a TV series, or does this mean I had horribly bad luck pitching it to the wrong people? I don't know. This is the stuff I need to figure out as I sketch out the next five years of my life. Part of me can't shake the temptation of being the underdog again -- like, launching my own sports site, hiring some talented writers and designers and trying to compete with the big guns. Like what Frank Deford did with the National. All right, the National lost $100 million. Bad example.

But I could see doing something crazy like that. I like taking chances, I am not afraid to fail, and beyond that, I am not afraid to fail violently and miserably. So anything is possible. A really good prediction would be, "Simmons is going to fail violently and miserably with a super-ambitious idea within the next five years." Lock it down.