Influence in the Decade: Bill Simmons Keeps Mainstream Podcasting Casual and Addictive
Bill Simmons is ending this decade in a vastly different place from where he started.
In 2010, Simmons began to work on one of ESPN’s most secretive web projects ever. One year removed from executive producing the smashing debut success of the worldwide leader’s 30 for 30 sports documentary series, Simmons was in the weeds for an editorial division of ESPN that is still the best thing the website has produced to date.
So it was that the sportswriter, who became one of ESPN’s top content creators, unveiled Grantland in the summer of 2011. Featuring top talent, long-form writing, and a beautiful layout, Grantland is still regarded as one of the best websites of its kind, blending sports, pop culture, technology, politics, and more seamlessly.
This 2012 tweet from Mindy Kaling sums up the culture of Grantland pretty perfectly.
With Grantland and 30 for 30 clicking on all cylinders and Simmons continuing to write for ESPN’s Page 2 while serving as a panelist on NBA Countdown with Jalen Rose, Simmons was arguably the biggest star at the network at the outset of the decade.
But considering that he now has a contract with HBO and owns and operates The Ringer, clearly something went wrong for Simmons over the course of the decade. Well, lots of things went wrong, but if you asked Simmons, he wouldn’t take any of them back. He’d just maybe do them differently.
In 2014 when the NFL and commissioner Roger Goodell egregiously mishandled the domestic violence case against Baltimore Ravens running back Ray Rice, Simmons unleashed fury against Goodell on his podcast, The BS Report, when he dared ESPN to suspend him and said,
“I just think not enough is being made out of the fact that they knew about the tape and they knew what was on it. Goodell, if he didn’t know what was on that tape, he’s a liar. I’m just saying it. He is lying. I think that dude is lying. If you put him up on a lie detector test that guy would fail. For all these people to pretend they didn’t know is such fucking bullshit. It really is. It’s such fucking bullshit. And for him to go in that press conference and pretend otherwise, I was so insulted. I really was.”
He was completely right, but ESPN suspended him for three weeks anyway, partially because he dared John Skipper, his then-boss, to suspend him, albeit indirectly, and partially because he was going to toe to toe with the NFL and Goodell, who often bankroll much of ESPN’s content on a daily basis. The former is the only aspect of the situation that Simmons feels some regret on.
Regardless, Simmons’ relationship with ESPN only soured from here and after departing NBA Countdown, following numerous poor reviews of his performance on the show, ESPN declined to pick up Simmons’ contract in 2015. He departed the network on terrible terms and Grantland was shuttered soon after. While Simmons has since smoothed things over with Skipper on his new podcast, The Bill Simmons Podcast, and made appearances on ESPN since 2015, there still remains a bit of tension between Simmons and Disney’s top brass.
Disney, of course, owns ESPN and in a recent interview, CEO Bob Iger was asked a true or false question about Simmons by Maureen Dowd of The New York Times. She said, “You miss being Bill Simmons’ boss.” Iger responded, “False.”
As much as Iger does not miss being Simmons’ boss, the same cannot be said of the people who work for Bill himself.
One of the top attributes that can be ascribed to Simmons is his consistent ability to find great talent. During the heyday of Grantland, Simmons enjoyed having the talents of people like Zach Lowe, Andy Greenwald, Wesley Morris, and Chuck Klosterman writing for the website. Each has gone on to do great things beyond Grantland as Lowe covers basketball for ESPN, Greenwald is currently running the new USA drama Briarpatch, Morris is a top film critic for The New York Times, and Klosterman is a best-selling author. So while Simmons moved on from Grantland to found The Ringer, the spiritual successor, he may not have been able to put this specific band back together, but there were a number of key Grantland figures who have now taken on top positions with The Ringer, especially in its founding.
Simmons started The Ringer with Chris Ryan, editorial director and host of The Watch with Greenwald, Sean Fennessey, chief content officer and host of The Big Picture, Juliet Litman, head of production and host of Jam Session, and Mallory Rubin, executive editor and host of Binge Mode. Each of them were chomping at the bit to work for Simmons again and did not hesitate to trust him fully when he began this new venture.
Simmons is easily memed (just look at his subreddit) and ridiculed, but people love following along with him and even the ribbing comes from the same place where people joke around and mock their friends. At the core of it, he’s a good guy and it’s why people love working for him and making consistent appearances on his podcast. His hands-off creative strategy has come with some failures (Any Given Wednesday, his HBO talk show, is one such example), but it has resulted in far more successes.
He started one of the top movie podcasts in the world, The Rewatchables, which has attracted the likes of Bill Hader and Aaron Sorkin. He founded Ringer Books, which will publish works from Shea Serrano, “Cousin” Sal Iacono, and Claire McNear. He inked an extended contract with HBO after the success of his sports documentary niche which began with Andre the Giant, the most watched sports doc in HBO’s history. And he engineered the infamous Ben Detrick story about the former Philadelphia 76ers general manager, Bryan Colangelo, who used burner accounts improperly on Twitter.
Likewise, Simmons repeatedly endears himself to celebrity guests, recurring guests who have since joined The Ringer in larger capacities (Iacono, Ryen Russillo, Joe House, Amy Nicholson) and has proven himself to be the exact sort of boss that anyone would love to work with. He can pal around on The Rewatchables and on The Bill Simmons Podcast and on Bachelor Party with his employees who see him as a boss and as a friend.
Former Grantland writer Bryan Curtis told The Guardian in 2016,
“I’ve never had an editor like him…Bill uniquely saw that something like this could work. He either directly hired or had a hand in hiring everybody who worked there. So I think that particular, wonderful, magical combination is totally Bill…Bill was the ultimate ‘player’s coach.’ He wanted you to succeed on your own terms and find the best version of you. He pushed you to achieve that. The first question we were asked was, ‘What are you interested in?’ and ‘What’s the piece you really want to write?’ and then you did that. That doesn’t happen everywhere. Most publications say ‘What is the piece that we would like you to write that you would most like to write?’ And the second question was always, ‘What form would you like to write it in?’ Oral history? A reported piece? A sort of column that comes out of some strange and previously not accessed part of your brain? It was all at our fingertips. We could deliver it any way we wanted to as long as it was really good.”
So it comes as no surprise that Simmons recognized the union of writers from The Ringer back in August in a time when Barstool Sports’ leader, Dave Portnoy, openly and illegally threatened his employees against unionizing.
And it’s not like Grantland was a one hit wonder, either, as Simmons has enjoyed immense success with The Ringer. He may not have been able to retain the talents of Lowe, Greenwald, Morris, and more to the same extent that they worked with Grantland, but he was repeatedly been able to put new finds on an even higher pedestal from Rubin to Serrano to Fennessey to Tate Frazier to Amanda Dobbins to Ben Lindbergh. The list goes on.
While he does not write columns or books anymore, Simmons still finds plenty of writing from the new crop of talent he has cultivated and he is finding so much success from the podcasting wing of The Ringer, a facet of business that was often quelled by ESPN, even when Simmons interviewed then-Senator Barack Obama. Now that he is able to throw his full weight behind the podcasting world, he has shown how lucrative it can truly be.
Regarding the success of podcasting, Simmons told Jason Lynch of AdWeek earlier this year,
“With the podcasts, some things worked in our favor, like the industry has really grown. Sponsors are coming around, but we could feel that in 2014 and 2015, because that was the first time I felt like A-list sponsors were starting to at least stiff around with podcasts. We always believed that there was going to be more available ad money. Now as we’re heading to this end of the decade, you’re definitely seeing a shift. People spend so much money on TV advertising right now, and yet, when you think about who’s watching TV and where they’re watching it — Netflix, Amazon, HBO — there’s been a shift where younger audiences are watching a lot of TV that doesn’t have ads. And you’re also seeing like local radio and that kind of stuff. All those audiences are going down too, and what’s going up is the podcast audience. So where’s that ad money going to go? We feel like a lot of it’s going to go toward podcasts. Not tens of billions but in three years, could it be like $2 billion, $3 billion, $4 billion for the entire podcast industry? Yeah, it could.”
The 2010s definitely saw a shift with podcasting. Credit where credit is due, people like Scott Aukerman, Rosie Morris, and Marc Maron have been involved in the industry even before the 2010s came around, but there’s no denying that it got broken out entirely in the past ten years. Partially thanks to Serial and partially thanks to the fact that every single topic you could ever want to listen to has a podcast now, the industry only continues to grow.
As for my personal history with podcasting, it can be traced back to the 2013 D23 Expo. Eager for updates, the top account that people recommended following was InsidetheMagic. Finding Ricky Brigante, someone who was as obsessed with Disney as I was, really opened my eyes so when I learned that he had his own podcast, I was curious and checked it out to hear reviews of The Wizarding World of Harry Potter at Universal Orlando Resort and of Thor: The Dark World. Back then, I listened to it on YouTube. It sounds primitive, but I really didn’t know what podcasting was! A lot can change six years, especially since I have my own podcast now.
Eventually, Brigante stopped producing content and I sort of fell out of favor with podcasting until I dabbled with a couple episodes of Comedy Bang! Bang! after I enjoyed watching the television show version while on the treadmill. I still didn’t get that podcasts came out weekly, though, so it never caught on terribly.
My high school English teacher recommended Serial to me and I listened to that in just two sittings, but, as a limited series, podcasting still was not catching on for me.
That is until October 1, 2015 when my life changed forever.
As an avid supporter and follower of Simmons, I was eager to see what he would do after being freed from the shackles of ESPN. Having never listened to The BS Report, I found my curiosity piqued when Simmons announced The Bill Simmons Podcast on his Twitter feed at the turn of October in my senior year of high school. I still remember sitting in my school’s auditorium during drama rehearsal, listening to the episode he did with Cousin Sal as the two guessed the gambling lines for the upcoming week of football games. I was amazed. I loved listening to these two talking because it felt like I was hanging out with them as we all discussed something I actually knew and cared about. It was funny, it was informative, and most of all, it was topical. Football happens weekly so this podcast had to happen weekly, too. I left the website I was listening to and finally downloaded an actual podcast app. Now, there’s over forty shows I stay subscribed to.
And it’s all because of Simmons. He broke open the podcasting industry by turning it into an addiction. With three episodes a week and regular segments and guests to look forward to, I found myself craving each release of a Simmons episode. Finally, it felt like I found a form of culture I’d been waiting so long for.
And while plenty of podcasts have heaps of high production values and immense effort that goes into it, Simmons kept me addicted by keeping it casual. That’s not to say his podcasts are effortless, but rather that he was very chill and was able to have conversations with guests like you’d have with your friends. On top of it, he can talk about the Fast and the Furious franchise as easily as he can talk about the 2003 Boston Red Sox team. He can chat with his buddy from college, the president, or Charlize Theron. Every week, his podcasts could be about absolutely anything. And I’ve loved listening to all of them for the past four years and, hopefully, for many more years to come.
Ultimately, Simmons’ influence in the decade, outside of the way he shaped my cultural and sporting-based consciousness, is best defined by the fact that he trusted his instincts and allowed himself to rise from a cog, albeit a definite voice, in the ESPN machine to one of the top multimedia company leaders in the entire world. For this to happen in a decade that was arguably the best in history for Boston sports (it’s either the 2000s or the 2010s), makes it a pretty great set of years for Simmons. He’s always led the charge and he’s always been able to see the way things are going. Where will he take us next?
