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."

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?

How about TV? You have that ongoing deal with HBO. Is that something you’d like to have another crack at?

I don’t think of it that way. I think of it more as, where can I do the best kind of work that will get seen or heard by a lot of people? The advantage I have now with the podcast is it has a huge audience, and I’m good with the fact that we can do a really good podcast and a lot of people are going to listen to it.

Obviously, the HBO show [2016’s Any Given Wednesday] didn’t work, but I’ve been thinking a lot about why, what the mindset was when we created that show. I was always thinking in 2015, 2016, [that] podcasts are a big thing. Long-form interviews really work. I’m good at them. This should work as a TV show. What we’ve seen over and over again the last three or four years is people would rather listen to a podcast. If I’m talking to whoever for 70 minutes, it’s more fun to put your AirPods in and to work out to it or drive or listen to it on your commute versus sitting in front of a television watching a few people talk to each other.

And there’s no real model the last four or five years where that works. I love [David] Letterman. I tried to watch his [Netflix] show [My Next Guest Needs No Introduction] and I couldn’t get through it. I’m trying to do whatever the best version of what I can do is. I haven’t seen a lot of TV shows where I’m like, “Oh, shit. I wish I had thought of that one.”

"I don’t understand the point of just having one strategy you’re all-in on."

It’s not just WarnerMedia. We can do that with whoever we want. The biggest thing I’ve been spending my time on the last eight months is how to grow: at Ringer Films, how we can grow nonscripted and scripted, how we can do 10-minute shows, 15-minute shows, narrative podcasts, all kind of the next level of creative stuff for those kinds of things. Because there are so many opportunities with that now. If you’re making content and it’s pretty good to really good, there’s more opportunities than ever. I feel good about the website and the podcasts. The biggest way for us to grow now is digital shows, narrative podcasts, things like that. We have a couple of documentaries going, a couple of things that we’re going to announce pretty soon. That’s like the next thing for us, because I always want the company to be like an octopus. I want us to have eight arms.

The other thing is you really have to be prepared that this might totally change. One of the smartest things we did in 2015 and 2016 when we were trying to figure out what The Ringer was as a website, the model at the time was Facebook is the most important thing, and you should optimize for that. And we didn’t trust it because first of all, you’re creating ideas and content for this algorithm that could change tomorrow. So we were like, all we can do is try to do the best stuff we can do, try to create a brand, try to at least get people to know what The Ringer is and then hopefully they fall for some of the stuff we’re doing and they like it. I’m really happy we played it that way, because you look at ’15 and ’16 and how powerful Facebook was before everybody realized not to trust them.

Yeah, how many media companies pivoted to video because of what Facebook said?

The video thing was always weird to me. In general, I don’t understand the point of just having one strategy you’re all in on. I think that’s crazy, because you never know when things are going to shift. We did Grantland, which I developed for a year and a half [in 2010 and 2011]. The whole site was devised for people to read on computers at work, on desktops. And now, by the end of this decade, you look at the traffic that we have and it’s probably 75-80% iPhones/iPads, especially on the weekends. I used to write these 8,500-word mailbags. I would never be able to do that now because everyone is reading it on their iPhone. You’d have a heart attack trying to scroll through it.

Things change fast. The eras are always shorter than you think. Now it’s the same thing with subscriptions—“Subscription time, here we go!” All right, well, maybe that’s not going to be the way it is 18 months from now. Do you have a Plan B?

How has your relationship with brands and sponsors changed?

That’s one thing we have gotten better at the last couple of years: how to deal with brands and how to take advantage of when they want to do something with us. Come up with a good idea and also understand things from their perspective. Where brands were 10 years ago when we were launching Grantland versus where people are now, it just seems like they get what we’re doing so much better. We’re in meetings now where if we’re talking about The Rewatchables [podcast], they’ve actually listened to it. They’re not nodding like I’m talking about some foreign planet, which is how I felt with Grantland the first few years.

The only people at Grantland that really got what we were doing was Subway, and they were all in. Now, it seems like a lot more people are like that. It’s cool to go into meetings where people actually understand who we are and what we do.

What’s an example of a recent partnership that has been successful?

We have a really good relationship with State Farm. I sound like a Kool-Aid drinker, but they’re just smart. We were doing this NBA draft guide. We explained it to them, and they get it. They’re like, “What if we also did a couple of videos?” Ryen Russillo did a lottery special, and we did a couple of State Farm “What if?” things in the middle. It was like a natural integration, and that was pretty cool. I like when people just get what we do and trust us because I feel like we should be trusted at this point. The days of somebody just slapping a banner on a website are long gone.