The timing couldn’t have been tighter. This year, it was announced that media multi-hyphenate and erstwhile ESPN personality Bill Simmons was selling The Ringer, the podcast-heavy digital outlet he launched in 2016, to Spotify. The deal was finalized on a Friday in March. The following Wednesday, Tom Hanks and Rita Wilson tested positive for COVID-19, as did Utah Jazz player Rudy Gobert. Almost overnight, entertainment and sports — The Ringer’s primary coverage areas — ground to a halt and the world as we knew it suddenly ceased to exist.
Spotify’s acquisition, reportedly valued at up to $250 million, was chiefly driven by The Ringer’s strong on-demand audio operation anchored by Simmons’s wildly popular eponymous podcast. It was the latest head-turning move in Spotify’s aggressive push into podcasting, which has come to be understood as a major step in the Swedish company’s grand ambitions to become something much more totalizing than a mere music-streaming platform. But the future is hard to actualize right now. While podcasting hasn’t (yet) been hit as hard as the rest of the media industry, it still saw a dip in overall listenership as lockdowns wiped out daily commutes, one of the fundamental touch points for consumers. Many podcast businesses are bracing for more turbulence ahead.
Despite the uncertainties, Spotify appears to be pushing on with its quest for media dominance, even as it navigates shocks to advertising revenue due to the bleak economic effects brought on by the pandemic. Simmons will be deeply involved in those efforts, but for now, he’s been working to adapt The Ringer to a world without fresh supplies of sports and pop culture hooks. That’s meant leaning harder into nostalgia and evergreen material, exemplified by podcasts such as Binge Mode, The Rewatchables, and Way Down the Hole, a rewatch podcast about The Wire that’s hosted by Jemele Hill and Van Lathan. Simmons and I jumped on the phone last week to talk about those recalibration efforts along with several other things I’ve wanted to know since the deal was announced.
You sold The Ringer, and then the pandemic immediately shut everything down. How did that affect plans you had following the sale?
Yeah, it was weird to join a company and then not actually have real meetings with anybody. We’ve managed, and certainly a lot of people are in worse shape than just not being able to talk to your bosses, but it was an unusual way to start our relationship.
The biggest challenge for us is just, “When do sports come back?” There were two big reasons I went to Spotify. One was that they were going to blow out The Ringer — make it bigger, all that stuff. But the second was, they wanted me to figure out their global sports strategy with [Spotify head of studios and video] Courtney Holt, who’s my boss and who reports to [Spotify chief content officer] Dawn Ostroff. That was one of the tasks that we had this first year, and that’s impossible to figure out when we don’t know when sports are coming back. We’ve been able to figure out some stuff, but just not knowing when anything is going to come back is paralyzing.
With sports mostly on hold, what’s Plan B?
From a Ringer standpoint, we were pretty well positioned for a lot of the stuff going on right now. That goes back to the Grantland days: We try to think outside of the box and get creative during dead spots on the calendar. There are stretches — mid-February, two weeks in August, maybe the last week of July — when there is, like, nothing going on. So we get creative, like: “Oh, this would be a good week to do a theme week. This would be a good week to double down on this.” With The Ringer, nerd culture and nostalgia culture are things we’ve been good at, and I think I’ve been really good at. You look at something like The Rewatchables and Binge Mode, the Book of Basketball pod, The Watch, things like that — we go backwards a lot.
So once lockdowns started and sports were done and movies weren’t coming out, everybody started going backwards. We’ve been doing that for 10 years, so we were ready to go. Problem is, I think the audience is going to start to get bored of it. Going backwards has a shelf life, and at some point you’re going to need new stuff. It’s fun to react to things. We’ve had so much success on the website, and even more on the podcast side, by reacting and being there when something happens. It’s something we didn’t do at Grantland because we didn’t have to — we had ESPN.com covering news and reacting right away, so we positioned ourselves as levitating above that, taking our sweet time, doing bigger pieces.
I do think that 10 or 15 years ago, it took people longer to get over news moments. But in 2020, people are like, “What just happened? What’d you think?” And you have about 12 to 18 hours to jump on that before people start looking forward. When I look at stuff I did at Grantland, I wish I knew then what I know now. It’s better to be in the moment. Audiences love hearing people they enjoy reacting to something that just occurred. If you have a blend of that, plus good interviews and thoughtful narrative stuff, then you have a podcast network. But you still need stuff to react to. That’s what’s been missing.
Something notable we’ve observed with podcasts during this time is a dip in audiences, which seems to be leveling out. Have you seen a similar pattern with Ringer shows?
Only with a couple, and really mostly with the shows that reacted to stuff. Ringer NBA and Ringer NFL were “in the moment” shows. Once you remove that, those programs get hurt. But honestly, some of our other shows have either stayed pretty good or in some cases even grown a tiny bit. The Rewatchables is a good example of a show that feels even more positioned to succeed now because there’s nothing going on.
But yeah, look, it’s ultimately not awesome, since a lot of people listen to podcasts when they’re working out, when they’re commuting, when they’re in the car, when they’re going from point A to point B. If you’re home, I don’t think you’re necessarily less likely to listen to podcasts, but podcasts are competing against other things — hundreds of channels, streaming services … all this stuff cannibalizes each other.
And the other thing is just that there are more podcasts. More content, more people in the space. The products are better. You’re competing against more shows. When I launched the BS podcast in 2007, I was really the only sports podcast that was prominent for a few years until ESPN started to get traction with the fantasy podcast. Even with Grantland, we had nine of the ten biggest podcasts at ESPN. It just wasn’t a space that a lot of people were in. Now you look at the charts, you have all these pods that are targeted to specific audiences. There’s what, 800,000 podcasts now? So it makes sense that audiences would, for the bigger properties, stay the same or maybe slightly go down. I’m not making excuses; I just think it’s the reality of it. We definitely crested from 2018 to 2019 as our shows got better, and our audience has stayed pretty much the same for, I would say, the last seven, eight, nine months.
You mentioned that part of the reason behind the sale to Spotify was that you were going to lead the charge for global sports. When Spotify CEO Daniel Ek first talked about the deal, he mentioned feeling that they bought “the next ESPN.” What is Spotify’s goal with sports?
That was nice of him to say. I think they looked at us in two ways. One is, “Could we blow out The Ringer into something bigger with more resources?” Yes. And then, “How do we figure out sports?” It’s a nut they’ve been trying to crack for two years, but it’s hard to find the right team. I think they felt they had most of the right pieces in place, and the thing they were missing was that one person who had succeeded in this space and had gut instinct on what works.
For me, the domestic part is easy. I know I can help with that. The daunting part — the real challenge, which I’m excited about — is the global part. Because Spotify wants to be the dominant audio platform everywhere. That was the No. 1 reason I wanted to go there. I’m at a point in my life where I really just want to win. I’ve been in situations of all kinds over the last 20, 25 years, but the most fun I had was probably 2009 to 2014 at ESPN when we had the combination of the reach, the right people behind the scenes, the right ambition, and a lot of money. And people who are willing to take chances with it. If you look back at the stuff we attempted during that stretch, it was a cool time for the company. It’s probably something that will not happen again for them because of the way subs went backwards and everything.
Spotify reminded me of that point when I was at ESPN and a lot of the stars had aligned. The big difference is Daniel. The guy is like a genius. He might be Steve Jobs for audio. That’s what’s different than ESPN. ESPN always had different executives, an upper level by consensus. Daniel’s somebody who has real vision for how this stuff works, and he’s been vindicated in a lot of ways already. So the chance to work with somebody like that was cool.
The other thing is that they don’t have a lot of competition for what their goals are. People always compare them to Netflix and where Netflix was four, five years ago. The similarities are definitely obvious. You have Spotify, which has just been hammering home on the technology and know-how side to a point now where they have this war chest, which is where Netflix was in 2014–’15, before everybody realized what was happening. Netflix had a six, seven year head start on everybody, and you can feel it. They’re the dominant video platform. Sometime mid-decade, people started to realize what was happening and were like, “Oh shit, we’ve got to come up with our own versions,” and that’s what led to where we are now with Disney+ and HBO Max and Apple TV and Amazon Prime and all these things.
Spotify is in the same position, except I don’t know who the competitors are going to be. There are pieces of different competitors, but no real rival other than Apple, and Apple doesn’t care about podcasts like Spotify does. Apple makes so much money from apps and iPhones and computers, everything else. As you’ve written about a million times, they’ve never committed to the kind of money it would take to try to turn that corner.
Podcasts still feel like an afterthought for them, for sure.
They can put out AirPods for $250 and sell out in a week. They have so many different ways to generate revenue, and I just don’t think podcasts are a huge thing for them. You look at how they’ve mobilized around Apple TV+, all the money spent on that. They’ve never done that for audio. They feel like they’re already in this space. They’re getting all the data from it, and they’re good. Which is fine; it might even be the right choice. But for Spotify, it’s a really unique chance to become dominant in the most major way.
As we were deciding whether to do the deal, I was reading different books and stuff, especially about Disney. In the ’80s, people thought they knew what Disney was, right? They had parks, animation, made some movies, made some other things. Then Michael Eisner gets in there and within ten years turns them into a completely different, much bigger company. And then Bob Iger goes even three steps beyond that. Now they’re the biggest media company we have. Do I think that could happen at Spotify? Yeah, maybe. It depends. At some point, are they going to think, “We’re killing it in audio. Should we start doing more?” You never know.
Were there offers from other companies?
No. There’s been so much misinformation and bad reporting. We never hired a banker. We never seriously talked to other companies, and anybody who says we did is lying. We weren’t trying to sell.
We formed the company in October 2015. We were young. We were trying to build something. We had a lot of success in 2018 and 2019. We were at the point where we were profitable. For me personally, I didn’t have to answer to anybody. I had just been in a really bizarre situation at ESPN, where the stars were aligned for a few years, and then all of a sudden people switched jobs and the stars were no longer aligned. From that moment on, I wanted to be in control of my own destiny. I loved what we did with The Ringer the first three years. We were not trying to sell.
Spotify has been thinking about us going back to the end of 2018, when they were beginning to get into podcasts. We had a bunch of meetings with them, and I’m a moron. I missed it. I didn’t realize they were scouting us, because we’d been pretty clear that we didn’t want to sell. When they made the Gimlet move, and Parcast, I called Courtney, because we had good conversations with them and were already developing The Hottest Take and things like that. I was like, “I like everything I’ve read about these moves that you’re making and how you’re thinking about stuff, and I think it’s worth us talking a little more seriously.” We stayed in touch, and it didn’t really heat up until September.
The only other person we talked to even a tiny bit was AT&T, because they bought HBO. HBO owned a minor stake in The Ringer, and they wanted to know what they had. And I remember I talked to somebody from Bleacher Report. There was a split second where it was like, “What would this look like?” But it was never serious, and it wasn’t even something I wanted to do.
What’s the nature of your relationship with HBO now?
I still have a first-look deal with them, and I’m still developing this music documentary series that we were really moving on — though now you can’t film anything. Like a lot of projects, it’s been pause-buttoned, but I’m just waiting for when we can keep working on that.
Spotify is an audio company. They’re beginning to play around with video again, but how does The Ringer’s website serve them?
Look, for anybody to try to buy us, you had to be all-in on everything we were doing. We’d put a lot of thought and energy into what we wanted our company to be, and what we wanted to create was a multimedia brand that did a bunch of different things: print, audio, video, documentaries, potentially other nonfiction programming.
I have a handwritten piece of paper from a month after I left ESPN. So like June 2015. It sketched out everything I wanted to do with The Ringer, and we did like 90% of it. It’s pretty cool, actually. I got suspended from ESPN in 2014, and that was when I seriously started thinking, well, I didn’t want to leave, because I couldn’t conceive of Grantland going on and me not being involved, but at the same time, I knew the forces were moving against me. That was when I really started researching everything, talking to people, and figuring out a game plan.
We knew in 2015 and ’16 that the website was never going to be a massive moneymaker. It’s just the way print on the web was going. We felt like, to create a brand you have to have a bunch of pieces to that brand that people care about. We knew that the website allowed us to stay in the day-to-day and that we would have a really good website because of all the DNA we had with me and Sean [Fennessey] and Mallory [Rubin], Chris [Ryan] and Juliet [Litman]. And most importantly, we knew it’d be a way to find young talent or talent that fell through the cracks somewhere else.
It always made sense, and it still makes sense. You think about some of the people that we have hosting podcasts now, we never would have expected they would be hosting podcasts. We were able over and over again to find talent through the website, and that’s an advantage. So it’s still important to us. What happens to print in 2020 on the web? I have no idea. A lot of this stuff’s going to go to subscription, but it’s still important to us, and at every step of the way with Spotify we made that clear to them.
There was friction with the union when news about the acquisition talks emerged. Where are you in that relationship right now?
I mean, friction, I don’t know about. We recognized it in three days. And then, from a deal standpoint, there were rumors that we were close to a deal. You can’t talk about it with anybody. That’s just how business works. That’s it. There’s really no story behind it. And it sucks not to be able to tell people, but it sucks not being able to tell anybody. I couldn’t tell friends that I’ve had since I was 15, you know? It’s just the way it goes. When you’re down the road negotiating with somebody, you sign nondisclosure agreements, you can’t talk about it, period. So I don’t know if “friction” is the right word. But yeah, we’re still bargaining. It’s been ten months.
Are you interested in doing live television ever again?
I want to crush this moment that we have with Spotify. It’s always been hard for me to try to be split in five different ways. Probably the most success I’ve had with that was the 2012-’13 range, when I was running Grantland and writing my column, doing my podcast, doing 30 for 30, and then over on NBA Countdown. I got burned out in, like, I don’t know, 18 months. It wasn’t sustainable. Now I’m older, too, so that’s like having a torn ACL.
It’s funny, with the HBO show, I was really convinced that because long-form interviews were working so well on podcasts, they would work as a TV show. And now, of course, podcasts beat long-form interviews on TV. So I like where I’m at now with that. I love doing my podcast. I love the creativity of it, the format. I don’t just mean that podcast. I love The Rewatchables. I love doing the Book of Basketball stuff. I love popping on other people’s pods.
From a TV standpoint, would I want to be a talking head? Probably not. I feel like I’m a talking head now; you just can’t see it. I guess popping up on different TV shows every once in a while is something that would be fun to do, but I don’t really understand what the point would be. It’s debilitating. TV is hard. You really have to be on, and it’s harder than you’d think it would be. Especially when I was doing Countdown, we would have the pregame show for either a half hour or an hour and then a break, and it would be an an hour and a half to get to halftime, then all of a sudden you go back on and you just have to magically flip your On switch again. I was always in awe of the people who could do that. Michelle Beadle was like that. I’d never seen anything like it. Magic was like that. He had an On switch. I can do that stuff and pull it off, but it’s harder for me to juggle it with other things.
The Spotify VOD-casting thing is going to be really cool and different, and I’m excited for that. I know you wrote about it last week. Some people, for whatever reason, like watching podcasts. They just do. Spotify has the technology to combine that experience, so whether you want to watch it or you want to listen to it, you’re getting it in the same place. The goal of Spotify is, “We want you on our app — come to our app and stay there.” This is something they spent, God only knows, at least a year trying to develop the technology for it. That’s a good example of why we wanted to go there. If we were going to work with — and for — somebody else, we wanted it to be a place where they’re like, “Hey, we created this awesome technology. Can you guys be the test case for it?” It’s like, “Great, that sounds awesome.”
This interview has been edited and condensed for clarity.