Simmons, Klosterman, and why writers write

In a recent “B.S. Report” podcast, Bill Simmons and guest Chuck Klosterman started talking about their upcoming ESPN-backed website project, which led into a fascinating discussion of what writing and publications inspired them when they were younger, where they see writing going on the web, and more broadly, what motivates them as writers.

Check it out here. The exchange starts at around the 29:30 mark… The more general discussion of why they write starts at around the 35 minute mark. You don’t have to be into sports or pop culture to find their exchange interesting.

New media Sports Guy rises as old media sinks

Bill Simmons, the 'Sports Guy'A few weeks ago, New York Times did an interesting profile of one of my favorite writers, Bill Simmons, better known as ESPN’s “Sports Guy.”

It includes some interest background on the early days and his rise to becoming a model of a new breed of columnist that broke a lot of the conventional rules of the news business:

At the time, Mr. Simmons was 28, making $50 a week as a contributor to America Online’s Digital City Boston, he recalled in a recent interview. “My goal was to make the welcome screen,” he said.

Barely a decade later, he has proved that prediction true: He is the Sports Guy on, where his column has an estimated 1.4 million page views a month; his weekly podcasts have been downloaded 21 million times this year via iTunes; and his new book, at 700-plus pages, “The Book of Basketball,” reached No. 1 on The New York Times nonfiction best-seller list last week.

That Mr. Simmons is perhaps America’s most famous sports columnist, with a salary said to put him among a tiny elite of sports commentators, is a tribute to his undeniable work ethic and fascination with his subjects: sports, popular culture, lists, himself, basketball, his friends and family, and his readers.

Perhaps most interesting was how his early struggles to make a career as a writer pushed him to the web:

“I tried to break in conventionally — but it didn’t matter how good you were, you had to wait 10 to 12 years to get a column,” he said in an interview. He wrote for a while and even spent a year bartending before giving the Internet a shot. “The Web site was a way to get out all the frustration of not having a column.”

Over the years, the Internet has prevailed over print — in July he stopped writing his column in ESPN’s magazine. “I got bored with the space of it,” he said, “of having to write 1,200 words, and with a deadline six days in advance. It is impossible to write a great sports column six days in advance.”

Simmons’ approach and style reflect his roots on the web. His stories are punchy, timely, light, and filled with pop culture references and hyperlinks. When he wants to, he writes long: his columns can run anywhere from eight to 20 pages, depending on his whim. He devotes columns to “mailbag” question and answers from readers. His podcast (“The B.S Report”) rivals his column for popularity. He tweets a lot.

But it’s not just a matter of using the right tools and and media. It’s also clear that Simmons has a passion and love for his work. I think this makes a difference. When you read his column or listen to his show, it’s evident that he’s having fun.

Simmons uses the full range of modern media to build a community of readers and listeners. He’s a good example of a modern approach to journalism and writing that breaks many of the established “rules.” He shows that the newspaper business may be shrinking, but the market for good, smart writing remains strong.

Check out the rest of the NY Times profile here.

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