I'd ____ Bill Simmons
If I had money, I'd fund Bill Simmons' next venture.
If I owned a company, I'd hire Bill Simmons.
I'd also work for Bill Simmons (the likeliest of these three scenarios).
Why? Because I'm drawn to people who are curious, ambitious, and versatile. Because I respect people who aren't afraid of speaking truth to power, but who also use power to speak truth. Because there are few people bold (or arrogant) enough to say, "I know what's good and I'm going to surround myself with good people, empower them, and lead the way." As Seth Godin has said, "If your standard is to never be called arrogant, you've probably walked away from your calling."
There aren't many willing to lead because it comes with hassle and risk. But Simmons started Grantland and championed 30 for 30. There aren't many people who are good at one thing who say, "I'm going to try something else!" Remember Simmons' transitions to podcasting and television? Few people have that dogged determination and work ethic, but never lose that folksy, playful way of relating to just about everyone. That's how Simmons can write a beautiful ode to the family dog or describe a life-altering trip to the Azteca that stays with the audience for years.
Despite his flaws and gaffes, and certainly notwithstanding today's news that he's parting ways with ESPN, I believe he's the best and safest bet in sports media. If there were 10 Bill Simmons working in sports, I'm not sure any of us would ever get anything done. And that's why I can't wait to see what's next.