I am beyond excited to see what Bill Simmons does post-ESPN. I know ESPN did a lot for his career, but truthfully, I think he did just as much if not more for ESPN. Without Simmons, I could see ESPN still struggling to find an online voice to match the broadcast voice it had in Stu Scott and being in a much stiffer competition with Fox Sports for broadcast dominance and with SI and SB Nation online. These are the three options I think Bill Simmons should consider (not that I have inside info):
1. Take VC money and build his own brand. This is a sexy option for someone like him who seems to want the control, but he'll ultimately have to answer to a board of directors and be expected to generate an exit within 5-10 years meaning this isn't the lifelong option most likely.
2. Take a $10mm-$20mm/year deal with Marissa Mayer's Yahoo. This is a very interesting option because Yahoo does have a solid foundation of users that aren't necessarily the most tech-savvy, but are very much into pop culture and sports like Simmons so maybe this is a way to get into tech without being expected to generate an exit or have a board of directors.
3. Go to Fox or Sports Illustrated and compete with ESPN head on. I think this is what Simmons may ultimately do. He loves sports, he loves the competition, and I could see him taking a bunch of great talent with him.
A potential 4th option would be Simmons figuring out a way to get athletes to back him on a venture; perhaps he could join Derek Jeter's The Players Journal as its editor-in-chief. Simmons mostly seems to want to rub elbows with and share stories amongst famous athletes and entertainers, so I'm betting he would entertain this option to.
Regardless of what he does, I will definitely be spending less time on ESPN.com and much more time wherever he ends up.