CHAPTER 3

CHIPPING TOWARD YOUR NEXT BIG MOVE

In May 2015, ESPN fired sportswriter, editor, and podcast host Bill Simmons. The company considered him “disrespectful.” He’d argued with his bosses, provoked controversial attention, and even publicly bashed the NFL commissioner. Oh, and then he dared ESPN to fire him over it.

ESPN took him up on that dare and let him go.

It was a $200 million mistake.

Simmons had spent 15 years at ESPN, cultivating fresh journalistic ideas, challenging incumbent thinking about impartiality, and stoking passions with his contentious writing and podcast. Nothing was traditional about Simmons. In addition to his radical use of language, he never minded giving particular attention to his favorite Bostonian sports teams, ...

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