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.
...They could be nervous that Bill might leave. I'm not sure about that -- for all the griping about creative control, I suspect he likes the comfy cash position and brand association. Otherwise, he would have left at his last contract renewal, when he had lots of other ways to go.
That said, the state of the world has changed dramatically in even the year or two since then. Rather than looking for a multi-million dollar deal from a Fanhouse or a Yahoo or a CBS or a Fox, there are plenty of opportunities for Bill to strike out on his own.
If he did -- like, tomorrow -- I'm pretty sure he could create millions of dollars of revenue for himself (not to mention autonomy), virtually overnight. I would hope he sees that, but only chooses to ignore it -- in favor of other competing drivers that keep him happy where he is. (And there are plenty of them, both intrinsic and explicit.)
All that said, ESPN execs would be wise to remember the lesson of the Washington Post and Politico. Politico's founders came to the Washington Post FIRST, explaining their great idea. The Post passed; the guys found outside investment and launched their own company, which has nimbly beaten the Post at its own game, in its own backyard.
I'm not saying SimmonsCo would beat ESPN -- then again, it doesn't have to. Bill's departure wouldn't hurt ESPN's revenues; Bill's new independent company would create new value -- the best kind. Still: ESPN would miss not only Bill's popularity but his creative energy on projects he engages on -- see his key involvement in "30 for 30."
And so here's my free consulting advice to ESPN:
Approach Bill with an offer of funding and equity to create his own company -- NOT an ESPN subsidiary, but a stand-alone company that simply creates a financial stake in SimmonsCo for ESPN. Maybe that would satisfy Bill's entrepreneurial jones -- while still allowing ESPN to enjoy the upside.
Or maybe Bill really does say "Eff it," walks away from ESPN with nothing more than his talent and his personal brand and tries to make it as a sports-media entrepreneur. There is plenty of investment money out there that would probably pay big -- even overpay -- to fund Bill's dream. (Bill should just amble down his nearest L.A. freeway to would-be content mogul Jay Penske's office, as Penske tries to figure out what he'll do with the uber-URL fan.com.)
As we talked about last week at the blogs conference in Las Vegas, it's not just about quality -- it's about distribution. Now, between the consumer interest in Simmons (going directly through the front door) and the high potential interest of distribution partners (who can put his content in front of a lot of people -- like ESPN did when he came over from AOL), he will be on to something... potentially something very big.
Want a great example of a personal brand combined with some very savvy content strategy? Huffington Post. I actually think that Simmons could pull off something similar -- if not at HuffPo's magnitude -- provided Bill had the right folks working on the strategy and technology sides.
I'd be curious to see how far that can go for him. My guess is far enough, at least to make him happy. Bill says he's not afraid to fail -- it would be a shame to see him waste that fearlessness by not taking the chance.