A lot has changed for Bill Simmons since he sat for an interview with Recode’s Peter Kafka back at the South by Southwest festival in March of 2015. He got fired from his longtime job at ESPN; he launched an HBO television series; he founded The Ringer on content platform Medium; HBO canceled his television series; his brave one-man assault on craven NFL commissioner Roger Goodell led to the ruin of Goodell’s previously sterling reputation [LINK/CITE NEEDED]; Medium announced it is abandoning ad-supported publication; Cris Collinsworth dunked on him; and so on. With that in mind, the two got together again for another interview, published today, to catch everybody up on what’s been going on with ol’ Bill.
It’s a very long interview! Maybe you don’t have time to read the whole thing right now. Here are some notable excerpts.
On the perception that, between HBO canceling his show and Medium abandoning his business model, his post-ESPN ventures have not had a great year:
I mean, people love to construct narrative.
On what went wrong with Any Given Wednesday with Bill Simmons, his canceled HBO show:
I’m not a performer [...] I said the same thing every time—“I’m not a performer.”
On the punishing, all-consuming artistic labor of writing a couple of sports columns a week:
I can’t do my column half-assed. I can’t just say, “Oh, I’m going to spend an hour and a half writing this, and then hand it in.” I wouldn’t ever do that. So for me, to do it correctly, I had to make sure I had the time to do it. There was no way I could really do it consistently while trying to do the TV show. The TV show was really, really hard.
On whether The Ringer makes any money:
Fuck yeah! The one thing that’s not a problem for us is money.
On whether, seriously, he’s sure that The Ringer, with a staff of 65 full-time people, actually makes money, which is not the same thing as presently having some money:
On how an informed and reasonable observer might find that claim, uh, let’s be euphemistic and call it surprising, given that Simmons’s similar claims about Grantland appeared to defy all logic and probably were not true, even though it had the most powerful media company on earth pointing a traffic firehose at its face all the time, an advantage not available to The Ringer:
I don’t know why people are so surprised by that.
Snapchat’s really interesting to me, because they’re innovative. We have a couple ideas for a show to try and create for them. I like that they seem to take the most chances out of anybody. Snapchat doesn’t give a fuck. They’ll actually try stuff.
I really like Facebook.
On speechwriter Jon Favreau, who was President Obama’s speechwriter from 2005 to 2013; famously wrote or helped write some of the most acclaimed political speeches of the 21st century; had already been profiled by the New York Times, Washington Post, Newsweek, and Esquire three years before the founding of Grantland; and then later co-hosted a podcast on The Ringer for a while:
He was writing a column every once in a while for the Daily Beast, and he’s a good writer. So when we were launching the site, I said, “Come into our world, we will figure out a writing/podcast strategy. You can leverage the podcast network we have, my podcast, my Twitter feed, all of these things. We’re going to make you a star.”
On why The Ringer doesn’t do more politics coverage, especially now:
Because we’re a sports and pop culture and tech site [and, uh, there’s nothing political about sports or pop culture or technology, I guess].
On what it’s like to be the brave pioneer who, way back in 2013, went against the tide of NFL coverage by criticizing it when literally nobody else was doing that at all:
I think one thing that’s changed since I was really going after them in 2013 and 14 is that now a lot of people do it. The worm has turned on [NFL Commissioner Roger] Goodell. I don’t think anybody’s writing about him favorably anymore.
On inventing the concept of “blogging” in 2016:
And what we’ve realized is, there’s like a three-hour window after something happened when you have to have a piece up.
Let’s say Paul George gets traded to the Celtics. At Grantland, maybe we wait until the next day to write about that. Here, we have to write within three hours, because there’s a three-hour window where I’m like, “Paul George got traded to the Celtics and I want to read everything about it.”
So the challenge for us is, how do we have a piece that goes up fast but that’s also well written. Maybe it’s short, but there’s also time and energy and thought put into it. It’s not just a word dump. We have a system now that we feel pretty good about. It took us about nine months to figure that out.
On the real actual humans who worked for him at Grantland:
But even at Grantland, there were always people around where I was like “hmm.” But here, I don’t feel that way. I feel like everybody believes in what we’re doing, and we have really good people.