The leaders he has hired are so fantastic, so incredible, he says, that he's hung a photo of them in his office next to a poster of Larry Bird. And where did he find those editors? A place called Grantland.
As The Ringer launches, Simmons and his staff find themselves balancing a nostalgic appreciation for what is no more – ESPN shut down Grantland last year – with rule one of the ever-spreading media entertainosphere. You can't get stuck in the past.
"I'm really excited that people care about Grantland, but this is a very different project," says Ringer editor-in-chief Sean Fennessey, who, it may come as no surprise, is a former Grantland editor.
Simmons created Grantland in 2011, a decade into his 14-year run at ESPN that launched him from little-known blogger into a sports media icon. He would make millions of dollars, write best-selling books and build a Twitter following that sits at 4.9 million and rising. ESPN also benefited. Beyond his on-camera success, Simmons came up with the station's lauded, documentary series "30 for 30" and launched Grantland, a site with a stellar writing staff and a willingness to go long, whether documenting the Wu-Tang Clan or a defensive tackle from the University of Washington.
But over time, Simmons, who is not known for holding his tongue, slammed a sports talk show in Boston, ESPN (repeatedly) and the National Football League in ways his bosses didn't appreciate. They scolded him, suspended him, and took away his tweeting privileges. And last year, when contract talks broke down, they cut ties with Simmons. He signed with HBO, key Grantlanders fled and ESPN shuttered the site.
In February, the day he announced The Ringer, Simmons answered a Tweet asking what he had learned from Grantland.
And on his podcast, Simmons went further.
"Just wait till The Ringer hires a public editor for ESPN that writes for The Ringer. That's going to be very unfriendly," Simmons said.
Simmons wasn't available to talk about The Ringer this week. A spokesman said he is too busy working on his TV show, which premieres on HBO June 22. As of now, he doesn't appear to have made good on his public editor taunt.
Of the 43-people assembled for The Ringer's staff so far, seven writers will cover culture and seven will take on sports. Two writers are covering technology, with a third bouncing between tech and culture. The Ringer also has former Obama speech writer (not the film director) Jon Favreau writing about politics through the 2016 election. For Favreau, Simmons is the main reason he's signed on.
"There is something to be said for Simmons's style of writing and talking," Favreau says. "I like that it combines a little bit of sports and culture. I like how broad that is. And I also think there's an element of not taking themselves too seriously that's sort of a Simmons trait and also a trait of a lot of the writers he's worked with in the past."
Fennessey says he wants to make one thing clear about Grantland. It was not perfect. Sometimes, the editors spent too much time brainstorming how to properly respond to, say, the Manti Te'o controversy without simply punching out a smart, quick take. He believes the site sometimes wrote too much to obsessives, getting trapped in analytics. The audience could have been broader. (It's unclear how many people clicked on Grantland. Internal statistics, provided by The Ringer, stated that the site had 10 million unique visitors a month during its final year. ESPN has always pegged that lower.)
"I think we just need to rely on the things we find fascinating," Fennessey says. "It's impossible to imagine we're going to hit one one-hundredth of the interesting stories happening in the world every day. But we've made an effort to find people who have specific passions."
That includes hiring away the Wall Street Journal's Kevin Clark, whose story on the Carolina Panthers' Waffle House habit caught Fennessey's eye, or bringing back Grantland's "Game of Thrones" fanatic Jason Concepcion.
Not everyone could be rounded up. Dan Fierman, Alex Pappademas and group of other Grantlanders were hired to revive MTV News. Wesley Morris took a gig at The New York Times. Even Robert Mays, a 28-year-old sportswriter, admitted that he wrestled with whether to return to Simmons.
After Grantland's demise, Mays went to work at The MMQB at Sports Illustrated. Simmons came to him with The Ringer. That's when SI offered Mays a staff job. That was once his dream gig. Peter King, SI's veteran football columnist and MMQB czar, had a long dinner with Mays.
"Look, I think anything with Bill Simmons attached to it has a chance to be a home run," King says. "The only thing I said was is that maybe what you want to do is you want to work in a different environment and work for somebody else rather than just work for your godfather."
Mays took that to heart. But ultimately, he turned SI down.
"It was obvious the first time I was back and me and Sean and Bill are sitting in Bill's office and you think, 'This is what I do,'" Mays says. "We also talked about how it was going to be different from Grantland and what they've learned the first time around."
There is Fennessey's talk of moving faster and reaching that broader readership. Mays says that he's going to be more careful about writing a "6,000-word recap of the NFL weekend." They are also excited about a focus on podcasting, a key element of the Simmons brand, as well as having control over the site. At Grantland, Simmons served as an employee of ESPN. The newly formed Bill Simmons Media Group will produce The Ringer.
HBO has signed on as an initial investor and has a first look deal with The Ringer for scripted and non-scripted programming. The relationship has already been paying off. In April, HBO began broadcasting "After the Thrones," which featured a group of The Ringer's staffers discussing "Game of Thrones." Later this month, HBO will launch "Any Given Wednesday," a weekly show hosted by Simmons.
In reality, not everyone on The Ringer bleeds Grantland. Alyssa Bereznak, 27, who will be covering technology, has worked for Yahoo News and Vanity Fair.
She was asked, when she applied, to list her favorite writers. New Yorker staff writer Adrian Chen, The Washington Post's Caitlin Dewey and Buzzfeed's Mat Honan were mentioned. She's eager to cover Internet culture, whether the dynamics in the gaming industry or what leads to the White House quoting DJ Khaled on Snapchat.
"Tech coverage can be overwhelmingly boring," she says. "What's really encouraging is that we have such brilliant support and editors who want us to do fun and unique things. I'm terrified every day that I'm going to be bad — being a writer — but I feel as confident as I possibly can be with the resources we've been given."