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."