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As countless ESPN defectors have discovered over the years, it’s difficult to stay relevant in the world of sports media after leaving the WorldWide Leader. But Bill Simmons is putting that conventional wisdom to the test.

When Simmons launched the sports and pop-culture website Grantland in 2011, it was one of the first online verticals that was centered around a single personality. Since then, countless sites have been spawned with a similar model, from Nate Silver’s data-centric FiveThirtyEight –– which is also owned by ESPN –– to renowned NBA reporter Adrian Wojnarowski’s The Vertical on Yahoo! Sports. But now, with the creation of an entire media empire, Simmons is taking that to the next level.


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Over the last eight months, the Bill Simmons Media Group has been steadily expanding its reach. First came the return of Simmons’ podcast, which netted close to seven million listens in its first month. Simmons’ old podcast on ESPN, the aptly titled BS Report, averaged roughly 3.2 million downloads per month over its last three years.

After Simmons’ podcast relaunched in October, all focus turned to his next online endeavor, The Ringer. The site, which is an ambitious mix of analytical sports and pop-culture commentary and features many ex-Grantland staffers, started distributing its newsletter in mid-March. It went live on June 1, with writers churning out content ranging from a profile of Joe Buck to a collection of news clips that tell the story of enigmatic WWE Chairman Vince McMahon. There’s plenty of NBA coverage, too, with Simmons also contributing the occasional op-ed.

But the holy grail for Simmons came last Wednesday, when his weekly half-hour talk show debuted on HBO. By all accounts, Any Given Wednesday‘s first episode was a rousing success, as actor Ben Affleck’s profanity-laced Deflategate rant went viral within hours.

After spending more than a decade hobnobbing with Hollywood’s elites, Simmons, 46, is no longer an outsider or an underdog. He’s now arguably the most famous person in sports media, which has afforded him the luxury to try one of the most ambitious projects in the industry to date. Simmons is testing just how far the à la carte media environment can go.

To help execute this vision, Simmons brought aboard former NFL Network executive producer Eric Weinberger in November to serve as the president of his company. I spoke with Weinberger recently to see how the rollout is going so far and what the future holds for the Bill Simmons Media Group.

Alex Reimer: What prodded you to leave the NFL and start working with Bill?

Eric Weinberger: “It was based on Bill’s vision and plans to create content here. I had a great run at the NFL and loved the opportunities that it gave me. The time had come in the fall when I really started to talk to Bill about what he wanted to do –– the position that I could have –– it just intrigue me so much. It was so exciting to talk about new ways of distributing content, building a website and helping him with all of the things that we wanted to do. And then, of course, the big draw was also to get to work with a company like HBO and help Bill grow his television presence. It was too exciting an opportunity to pass on.”

AR: So you had an inkling to explore projects outside of television?

EW: “I was lucky enough that at the NFL, we grew a media group, not just a television network. So I had so many opportunities to work with documentary filmmakers at NFL films and work on NFL.com in the digital media space. This was really about Bill. This was about the creative force and visionary that he is. I was very interested in partnering up with him and learning from him.”

AR: The Bill Simmons Media Group embodies the à la carte media environment we live in: you can have Bill with you on your commute, you can read the Ringer online, you can watch his TV show live or on demand. This really speaks to the power of Bill’s brand.

EW: “It seems that he’s at the point in his life and career where he’s very knowledgable about all of the areas; he’s learned from his past; and he was still very hungry to do this. He’s willing to take risks while also being very patient. He knows that all of our platforms are going to grow –– that’s one of the great things that we’ve been doing over the last seven months. There’s a real fire to create, but it’s balanced with patience.”

AR: How do you go about designing a show around Bill, who admittedly doesn’t have a lot of TV experience and isn’t a conventional TV personality.

EW: “It starts with his two big strengths: his incredible ability to have long-form conversations with people –– whether they’re his friends, celebrities or athletes. And the second is his writing. That’s what we know the first show had. It had two great conversations and it had two to three incredibly strong ‘Bill Simmons written projects.’ We want to build it and grow around his writing and these conversations.”

AR: What’s the next big benchmark for the Bill Simmons Media Group?

EW: “We have to start exploring more on the video side. We knew that was going to come after these first milestones, but the next phase is looking at how we’re going to produce video content in the most effective and efficient way possible.

“We’ve done an NBA Draft show on Periscope, we’ve done an Ask the Thrones show on Facebook live. We’ve been exploring a lot of different video applications, and that’s the next phase.”

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