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Bill Simmons took to Instagram on Oct. 1 to share a post celebrating the 10th anniversary of the very first episode of The Bill Simmons Podcast.
“Ten years ago today… the start of a new journey for me,” The Ringer founder wrote underneath a screenshot of the episode. “Thanks to everyone who came along for the ride.”
What a ride it’s been.
For somebody whose reputation has always been rooted in counterculture, the Sports Guy is now one of the most mainstream figures in sports media today. He sold his company to Spotify. He’s at the center of Netflix’s first foray into podcasting. And yet, somehow, it still doesn’t seem out of place when the man who’s supposed to embody the average sports fan is also sitting front row for WWE Raw.
But while there’s no questioning Simmons’ status in a space he very much helped shape — look no further than our own ranking of the most influential members of sports media, which he tops — his place atop the industry’s pantheon wasn’t nearly as secure a decade ago as it is now. In fact, the very first episode of The Bill Simmons Podcast felt way closer to being a DIY project than it did a show that presidential campaigns would be vying to appear on nine years later.
“I have not been heard from in five months,” Simmons said at the start of the Oct. 1, 2015, episode. “I would call it a sabbatical, is that being kind?”
“I think that’s being kind,” ‘Cousin’ Sal Iacono concurred.
“America has a lot of questions,” Simmons continued. “I don’t know if I’m going to answer them right now. I have a lot of thoughts about things. But I don’t think this is the time and place. Can we talk about football?”
That’s precisely what Simmons did —and continues to do —while building The Ringer from what was effectively a startup (albeit with significant financial backing) into a legitimate mainstream company worthy of its $200 million sale price. Even after selling The Ringer in 2020, the Boston native has remained as relevant as ever, as best evidenced by the Netflix deal to host several Ringer podcasts, including Simmons’ eponymous podcast and The Rewatchables, of which he is firmly the star.
It wasn’t always a linear progression for both Simmons — hello, Any Given Wednesday — and The Ringer, which evolved from a Grantland-lite website to an audio giant now central to Spotify’s strategy. But regardless of his or The Ringer’s respective successes, the through line has always been The Bill Simmons Podcast, which has effectively replaced his old ESPN columns as his connection to his modern audience.
As he’ll be the first to tell you, he doesn’t write because his fingers “no longer work,” but the reality is that Simmons was way ahead of the curve regarding podcasting’s place in sports media. Well before Pat McAfee was leasing his own show to ESPN for millions of dollars or Joe Rogan’s endorsement was helping swing election outcomes, Simmons was hosting what was then known as The B.S. Report for the Worldwide Leader. First launched in 2007, the pre-recorded audio offerings proved to be Simmons’ most important project, which is saying something for somebody who was so instrumental in shaping the internet age of sports media.
Just like he paved the way for media members to wear their fandom on their sleeve or make pop culture references in their writing, Simmons’ podcasting presence altered the industry as we know it. In 2015, it seemed fair to wonder whether he could remain relevant without ESPN’s infrastructure. In retrospect, we now know that all he needed was access to an audio recording device, and he’d be just fine.
It’s the same model that many have followed since, including high-profile personalities like McAfee and Dan Le Batard. Ironically, it’s also what Ryen Rusillo is looking to replicate as he leaves The Ringer and takes ownership of his own podcast feed while joining Barstool Sports.
Nearly a quarter-century ago, Simmons laid the blueprint for websites like Deadspin and even this one, proving that you don’t have to take yourself too seriously when you’re writing about sports. For the last ten years, he’s been perfecting a different model, showing that a loyal audience will follow you anywhere, even if it seems like an unconventional path.
As somebody who’s so obsessed with sports legacies, I often wonder what Simmons thinks about his own. Whatever it is, a significant portion has been shaped by the last 10 years, all starting with that Week 4 episode of “Guess the Lines” with Cousin Sal in 2015.
About Ben Axelrod
Ben Axelrod is a veteran of the sports media landscape, having most recently worked for NBC's Cleveland affiliate, WKYC. Prior to his time in Cleveland, he covered Ohio State football and the Big Ten for outlets including Cox Media Group, Bleacher Report, Scout and Rivals.