A star "talent" branching out on his own with the risk of less income over the near-term, but for greater opportunity in the long-term (financial and freedom from the bosses above) is a pretty common occurrence. Not sure what would be crazy about it. Grantland was supposed to be his "branching out." They basically said "Hey Bill, Page 2's traffic is literally all being driven in by you how about we fund and let you run an entire site based on the premise." He seems to have been given quite a bit of freedom on Grantland, whether he will admit it or not. He's not getting into a situation where he's making more money by leaving ESPN/Grantland when his contract is up, the only thing he will get is a little more freedom. Which I understand valuing that but he seems to have plenty other than being able to swear on his podcasts and threaten ESPN. It was a theoretical branching out that is really just him running a small department under the ESPN/Disney umbrella. Which he's getting paid more to do than he would be making if he started his own site without ESPN/Disney's funding and ability to drive in traffic. That's my point, he's not going to be able to make as much money by starting billsimmons.com. And again, that ignores the point that pretty much every "star" that left one big corporation to start their own business goes through that same exact issue. In the short-term they take a hit, but it helps that they have already earned a lot of money and presumably have a sweet nest egg and very little nut. And in the end they leave for freedom from their corporate overlords and the opportunity to potentially become overlords themselves.