I learned many surprising lessons from my 20 months as editor-in-chief of Deadspin, the skeptical, irreverent, hilarious, trailblazing sports outlet that entertained, offended, and educated audiences in roughly equal measure.
I learned from a cease-and-desist letter that Jacuzzi is a trademarked brand, and that the hotel room in which a world-famous soccer star was alleged to have raped a woman contained a mere “spa” or “hot tub.” I learned from inhaling Chartbeat that our very dumbest stories and our very smartest stories would always be our biggest traffic drivers. I learned from our general counsel more than I ever wanted to know about the precise limits of fair use. I learned from my coworkers — all of them brilliant and entirely deranged — that there is no limit to how hard I can laugh in a soul-suckingly bland Times Square cubicle farm. Even knowing how it all ended, I’d still take the job 100 times out of 100.
The most consequential lessons I learned, though, were about the ways in which I had misunderstood “free market” capitalism, and about what that meant for the industry that gave me my career. Those are the lessons I haven’t stopped agonizing over six years later, the ones that led to my first book but also caused scores of sleepless nights.
