It’s been nearly a decade since Bill Simmons worked for ESPN. Since leaving the network, Simmons has built his own publishing empire, forming The Ringer in 2016, which was later acquired by Spotify in 2020. Whenever a high-profile personality departs from ESPN, there is always chatter about how difficult the journey ahead might be and whether they will find success elsewhere.
On Monday afternoon, Simmons appeared as a guest on The Herd with Colin Cowherd to promote his HBO series Celtics City. During the conversation, he took a jab at those who doubted his and Cowherd’s ability to thrive after leaving ESPN.
“Look at this! Two guys that used to work for the Worldwide Leader still doing well,” exclaimed Simmons during the interview. “Funny how that happens, huh?”
Simmons, now 55, recently signed a contract extension with Spotify for a reported minimum of two years. Under this new deal, he will continue hosting The Bill Simmons Podcast while maintaining his role as Spotify’s head of talk strategy.
Meanwhile, Cowherd, 61, remains a prominent voice in sports media. After departing ESPN in 2015, he has continued to host his daily radio show, which is simulcast on FS1. Additionally, in 2021, he founded The Volume podcast network, which has since attracted major talent, including Nick Wright, Shannon Sharpe, and Draymond Green.
“Everyone says, ‘Oh, you can’t leave there!’” Simmons said, prompting laughter from Cowherd. “‘Oh no! Can’t leave the Worldwide Leader! Your whole life’s gonna fall apart!’ Guess what? We’re fine.”
Simmons’ comment was both a dig at ESPN and a response to skeptics who believed he and Cowherd would struggle post-ESPN. Cowherd’s laughter reinforced the idea that they have both done more than just land on their feet.
Simmons initially joined Spotify in 2020 when the streaming giant acquired The Ringer for approximately $250 million. At the time, CEO Daniel Ek was focused on expanding Spotify’s portfolio beyond music, aiming to build a stronger foothold in the podcasting industry.
By acquiring The Ringer, Spotify secured a well-established brand with a dedicated audience—one that Simmons had cultivated over many years, dating back to his ESPN days and the launch of The Ringer in 2016.
Beyond Simmons’ own podcast, Spotify has continued to invest heavily in exclusive content, securing major deals for The Joe Rogan Experience and Call Her Daddy.
Looking ahead, The Ringer is set to further expand its podcast lineup while integrating more video-based content into its programming. Meanwhile, Simmons reports directly to Roman Wadenmüller, who currently oversees Spotify Technology SA’s podcast division.
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