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:
(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, Foxsports.com, 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.







3:12 pm on October 22nd, 2009
Could you ever see Simmons writing for Yahoo, SI, ect? Or would he go into TV or the movie buisness?
3:19 pm on October 22nd, 2009
The thing about Simmons is that he’s a brilliantly entertaining writer. He mixes in enough pop-culture and semi-obscure 80s movies references to keep most people interested even when he’s talking about something like hockey (or soccer, or badminton, or whatever sport you don’t care about).
Wherever he ends up, he’ll keep a huge chunk of his fanbase, but he should be wary of the Howard Stern effect. Don’t assume that people will follow unless it’s still convenient and free.
3:32 pm on October 22nd, 2009
Simmons will eventually end up writing movies imho. Big money, high profile gig. Dream job.
He might parlay TV Series writing into movies. It’ll happen eventually if he pushes hard enough.
I don’t think he’ll write for Yahoo or under any other media corp banner besides ESPN unless he gets offered a ridiculous amount of money. Who knows, that might happen. Yahoo is getting seriously into the content biz, so I wouldn’t put it past them.
3:48 pm on October 22nd, 2009
And Bill will bolt Bristol before he gets involved in banging co-workers.
3:55 pm on October 22nd, 2009
He can’t leave ESPN! Who will they pick to run “The Ocho”?
4:05 pm on October 22nd, 2009
Brooks, you and Simmons should join forces…that would be a fantastic combo.
4:57 pm on October 22nd, 2009
I only pray that they use their powers for good, not evil.