Q&A: Bill Simmons’ The Ringer Thrives by Ignoring Facebook and Betting Big on Podcasts

As the outlet celebrates its third anniversary, its founder looks back—and ahead

'I always want the company to be like an octopus. I want us to have eight arms,' says Simmons.
The Ringer

While several upstart digital media companies have been struggling, Bill Simmons has found a groove with The Ringer, his pop culture and sports outlet, which is celebrating its third anniversary this month.

After leaving ESPN in 2015—capping a 14-year stint where, among other things, he launched the Grantland sports-and-pop-culture website—Simmons created a site that was much more than just Grantland 2.0. The Ringer now boasts a whopping 30 podcasts—including The Bill Simmons Podcast, Binge Mode, The Ringer MLB Show, Bachelor Party, One Shining Podcast and Black on the Air With Larry Wilmore—which had 53.5 million downloads in May. Podcast ad sales surpassed $15 million in 2018, a number that is significantly higher this year.

The outlet has branched out into Twitter aftershows for Game of Thrones (Talk the Thrones) and Big Little Lies (Big Little Live), and a Bachelor show for Hulu (Can I Steal You for a Second?). And the site itself had 46 million page views and 9 million monthly uniques in May, according to Google Analytics.

Simmons spoke with Adweek about The Ringer’s “daunting” start, why he thinks podcast advertising is about to become a billion-dollar-plus industry, his writing and TV future and how the outlet dodged a bullet by ignoring Facebook’s algorithm.

The following has been edited for length and clarity.

Adweek: When you launched The Ringer, what was your hope for what it would look like three years in as compared to what it ended up being?
Bill Simmons: It’s been three years at the website, but it really started October 2015 when we started with my podcast and we did The Watch [podcast] and started trying to hire people. We didn’t know how to do a lot of stuff. There’s just so many things that pop up that you don’t know how to do if you’ve never done it before, and it’s pretty daunting: where to get an office, how do you do benefits, where are we going to put the website, should we design it ourselves? So it was very fast and by the seat of your pants when we launched.  Now, I look at it three years later, and we’re so strong behind the scenes. We have an unbelievable copy desk and great editors and this great editorial infrastructure. That was really important to us.

You had said early on that you were going to lean very heavily into podcasts, but I don’t think that anyone, yourself included, imagined you would have 30 of them three years in.
I’ve got to be honest, I thought this would happen. This is the biggest reason why I was battling with ESPN behind the scenes those last 18 months, because I saw what was happening with podcasts. We were at a point at ESPN where I think we had nine of the 10 biggest podcasts they had, and they couldn’t monetize them, and it made no sense to me. So I just knew. Did I think we’d have 30 podcasts in three years? I don’t know. I knew we’d have a lot.

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.

"We’re trying to create a multimedia site, and that’s why I bristle when people think all the revenue we make is from podcasts. It's just not true."

So how have you been able to monetize those Ringer podcasts in a way that ESPN could not?
Look, this was not really their fault, because they make so much money from TV and from the relationships they have. So if they get Chevrolet for like $100 million and Chevrolet becomes the exclusive car sponsorship for SportsCenter and NFL Countdown and whatever else, they’re not thinking of getting Ford for my podcast for like $400,000.

It was a boutique business for them, and it should have been, because they made the lion’s share of their money from the stuff they could sell on their biggest properties like Monday Night Football and SportsCenter and all that stuff.  So I don’t really blame them for that. I think they could have been more creative with how they outsourced it.

We hired Midroll initially to sell my podcasts and some of the other Ringer podcasts. They had a lot of relationships with different sponsors and that’s been great. As our business has evolved, we now have a balance between brands that come to us directly, relationships that we can leverage for the website and the podcast network or videos and podcasts. We’re trying to create a multimedia site, and that’s why I bristle when people think all the revenue we make is from podcasts. It’s just not true. Our website is really successful right now, and for four straight months, we’ve had our best months. From a video side, we have a ton of opportunities right now, and we’ve been exploring a lot of them. Our goal has always been to create a multimedia digital company, and after three-plus years, I feel like we’re on our way.

As all of these platforms evolved, how do you feel about the stories on the website itself?
I’m really proud of how good the website is, and I think the last thing for us is more features. I think all of us agree we don’t have enough features yet, but it’s only been three years. With the website, we made a concerted effort not to try to chase traffic with the stuff we were doing but also have a nice balance of writing smartly about stuff that’s relevant combined with stuff that we cared about.

You built your career on your long online pieces, but with so many other things on your plate, do you miss writing as much as you used to?
It’s something my dad brings up to me all the time, because he’s really disappointed that I’m not writing. I look at it like, I would never do something half assed: “Oh, it’s Thursday. I’m just going to try to write this and then go back to all the other stuff I’m doing.” For me, it’s like golf.  You can’t just be like, “I’m going to play golf today. I haven’t played in five weeks and I’m going to shoot an 80.” Writing, you really have to be in it day in and day out. With how busy we are, I just don’t feel like I can give it the kind of time where I would be happy with what was coming out.

I also wrote for 20-plus years. You hit this point where you’ve said just about everything you’ve want to say. There are times, though, where I can still see the angles and I’ll be like, “Oh, man. I wish I had like four hours to just sit down and crank this out.” But now I’ve channeled some of that creativity toward the podcasts and then also the website just giving other people ideas, which is probably my favorite thing about what we’re doing. I love handing out ideas and pieces of ideas and seeing how it goes. But yes, ideally, I wish I was writing at least once a week. Maybe it’ll come back. Who knows?

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