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Cool Dad Job: Writer, Editor, Podcaster

Cool Dad Vibe: Barstool Philosopher

Cool Dad Bona Fides: It’s easy to forget that the Bill Simmons, aka the Sports Guy, is one of the first bloggers to ever make it big writing on the internet. In only a few years in the late 1990s, he went from writing hilarious 5,000-word screeds about Boston sports on AOL — while bartending at night to pay the bills — to a cult hero for millions of rabid sports fans across the country at ESPN. And in the process, he redefined the way sports were covered in America with a conversational style and heavy infusion of pop culture references and personal anecdotes, many about his two kids. He created the popular 30 for 30 documentary series, wrote two books, and launched Grantland, an intrepid sports-meets-culture site, before a highly publicized falling out with ESPN led him to HBO and eventually, to his own publication and podcast clearing house, The Ringer. Coolest thing he does? Employ Shea Serrano.