Simmons Mulls Own Site To Go Against ‘Big Guns’

As he makes the promotional rounds for his latest book, The Book of Basketball, Bill Simmons recently made an interesting statement to the HuffPo’s Jason Pinter - via THE ARENA BLOG:

Bill Simmons

(Jared, Bill invite us to eat fresh)

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.

Two questions come out of this.

Q1) If Simmons did quit ESPN, could he establish a site that could dent the hull of corporate monolith sport sites?

A) Without distribution from one of those same corporate sites or a consistent main media presence, it’d be very difficult for Simmons to build any substantial traffic, regardless of content. Not to mention the practical matter of setting up an infrastructure to sell advertising.

More likely, Simmons would start his own thing, then farm out ad sales to another company, while striking a distribution deal with one of the major sports portals (Yahoo,, etc.). Again, not saying his site couldn’t explode on its own without that assistance, but it’d be extremely difficult.

He’s already got a huge built-in following, so for all I know he could pull it off.

Q2) Will Simmons ever leave ESPN?

A) Unquestionably yes. He’s smartly using ESPN’s unparalleled distribution to get his product out there, and when the time is right, he’ll bolt. Simmons seems to have a sharper biz acumen than some of the other ESPNers who fled Bristol and were next spotted at the bottom of the career cliff.

When he leaves, it will be for something substantial. I look forward to it.