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Cool Dad Job: CEO of The Ringer

Latest Cool Dad Achievement: Launching a book imprint for his site and roughly 1000 new podcasts.

Simmons’s sequel to the Hall of Fame shuttered digital media venture Grantland, has steadily improved in exactly the way that Markelle Fultz’s shooting form has not. The Ringer Podcast Network drives massive listenership, but the thing really pushing the business forward is Simmons’s remarkable ability to recruit. His writers become editors and his editors become commentators and his commentators become stars (or, in the case of Andy Greenwald, showrunners). Meanwhile, Simmons continues to speak honestly about his struggles and successes raising two kids, and does it in a way that demystifies fatherhood without trolling anyone. (Worth noting: Simmons was mocked on Twitter last year by Shea Serrano, his employee, who boasted a higher Coolest Dads ranking. This year Shea Serrano has been removed from the list because the Spurs are mediocre and boring.)