What Would Bill Simmons Do, Cont'd

Now that Deadspin has publicly broken the story about Bill Simmons' emerging new venture within ESPN, I feel comfortable writing about it, because he is a big enough figure in sports media to make it really interesting to think about what it might be. Let's call this a follow-up post to the one I did a year ago, when Bill first started talking publicly about his ambitions beyond creating content himself.

I would classify the analysis in two categories: There's a clever, short answer and there's a grinding long answer. Let's start with the short answer:

(1) It doesn't matter what Bill does -- simply that he is doing something. Let me spin away from sports for a second, because I can think of a pretty good template:

"Peter Jackson presents [director you've never heard of]'s 'District 9.'"

The headline was Peter Jackson's association. That you'd never heard of the director didn't matter. That Jackson lent his credibility to the film was all that mattered. (That it turned out to be a great movie -- not insignificantly, made on a lean budget -- directly reflects Jackson's eye that made him so popular in the first place, of course.)

Whenever ESPN launches Bill's new initiative, the headline -- in effect -- is "Bill Simmons Presents..." It will give the project credibility. It will bring in an audience. And it will be successful.

This is the optimal scenario for Bill that I laid out last year, back when he was talking about starting his own thing: Given Bill's strengths, he is much better off letting ESPN manage the back-end and let him manage the creative part -- finding talent, shaping stories, lending his cred.

ESPN gets some credit for being entrepreneurially oriented, but not nearly as much as it should: From "PTI" and "SportsNation" and "30-for-30" on TV to aggressive entry into mobile and local to... well, whatever Bill launches in the next few weeks or months.

Part of that means giving smart people the freedom to flex -- obviously, that has become increasingly important to Bill and ESPN was wise to give him the budget and the room to do... well, again: Basically, whatever he wants.

(2) What specific forms does that take? Bill offered some foreshadowing in those interviews with the Huffington Post and Mediaite and NY Mag last fall -- he wants to encourage and develop and promote quality writing. ESPN uses a bunch of good writers already -- and obviously E-Ticket has had great success.

But Bill would presumably have the freedom to go out and find the best undervalued talent -- sports A&R, so to speak -- then use his brand and ESPN's platform to showcase their work and build their presence in the sports media ecosystem. So I think of it as a more nimble E-Ticket, a more honed version of the ESPN "Commentary" section. Bill used the analogy of "The National" -- recognizing that Deford had an abysmal sense for business.

Let's update the "National" analogy for today's media landscape. If I had to place a bet, I would say that Bill's project will be closer to a sports version of The Awl -- the reigning gold standard for quality writing by a range of talented contributors.

(I prefer "a sports Awl" to a construction of "like Page 2 used to be" -- among other reasons because Page 2's "golden era" was the product of a specific moment and specific strategy in pre-blog/pre-Facebook/pre-Twitter media history and it is folly to try to recreate it, rather than create something for today's reader and today's context.)

I suspect the "Awl" model because it is largely platform agnostic -- Bill doesn't seem to have an interest in creating the next great technology as much as he does leveraging technologies (podcasts, Twitter, web, TV) to distribute great content. The Awl model is about the writing first; ESPN, with its massive portal and platforms and reach and sales team, can handle the rest.

I have followed Bill's career for a long time -- back to the earliest posts at Digital Cities -- and I have never seen him more satisfied with something he has worked on (with justification!) than "30/30." He didn't create the content himself, but he set out a vision and helped others deliver on it. The logical next step is for him to to be a lead "show runner" -- to run his own product.

Let me echo something I said last year: I can count on one hand the number of people who could build a big, stand-alone sports-media product off their name brand -- Huffington-style (although she had the key help of some very savvy online content folks) or like Howard Stern.

Bill makes that short list. And, sure, it would have been intellectually interesting to see him strike out on his own -- how much funding could he have gotten for his own company, and how quickly? And how would he respond to the challenges of a pure start-up? But, frankly, why assume that risk when his goal is to build great products -- and ESPN will back him on it?

Ultimately, his best move was to leverage ESPN's resources to create his products (and it was in ESPN's best interests to give him that freedom and support).

Whatever Bill does next will scratch this latest entrepreneurial itch -- and will be the most interesting thing he has done so far. I suspect he is enjoying the process, and it will only inspire him to do more. That's a good thing for him personally, for the folks he is going to be working with (including ESPN) and for fans.

Looking back at my idle speculation on Bill's future from last fall, what I was really struck by was his fearlessness as it relates to failing -- not that he doesn't think he will fail, but that he doesn't mind if he fails... as long as he is taking a big swing.

Regardless of what he does, that mindset will be his greatest asset.

-- D.S.