Bill Simmons and John Skipper.

While the most interesting elements in Ringer founder Bill Simmons’ podcast with DAZN executive chairman John Skipper touch on Simmons’ departure from ESPN, there’s a lot of other significant sports media content in that 100-minute runtime as well. Here’s our breakdown of some of it with timestamps. But there’s much more in the whole thing, which you can listen to here:

Around the 4:00 minute mark, Simmons (seen at left above) introduces Skipper (seen at right above), and Skipper talks about the DAZN name. “The company needed a brand that could be cleared in the entire world, which is not trivial, it’s actually harder to do than you’d think. I think the logo looks great, the DAZN. We get a little grief, guff, for the Da Zone, which I think in the U.S. probably has the most baggage. Most of the world, it’s just an odd thing. And I’m always reminded that most brands aren’t good brands until you have a good product, and then nobody cares about the brand.”

Simmons: “Don’t they always say, four letter acronyms, it doesn’t matter what the four letters are, but people remember four letters the easiest?”

Skipper: “They do, and by the way, maybe the greatest four-letter acronym of all time? ESPN. It doesn’t really mean anything anymore except sports.”

Simmons: “No, it makes no sense.”

After that, Simmons and Skipper discuss their relationship a bit, and DAZN’s new three-month sponsorship deal with The Ringer.

Simmons: “We’ve known each other for almost 20 years. There was this period where we didn’t speak.”

Skipper: “It’s amazing, we look exactly the same.”

Simmons: “We look exactly the same. My hair’s probably whiter. And this is both weird and not weird because I feel that we have such a history together. We had dinner a few months ago and talked about a bunch of stuff. I think when somebody’s in your life for two decades, you probably have some bumps along the way. We had a pretty major bump.”

Skipper: “This is like Liz Taylor and Richard Burton, we want to get married again, we are getting married again!”

Simmons: “It’s a three-month marriage.”

Skipper: “A three-month marriage, a quickie marriage.”

Simmons: “But I think both of us found we had such a history together that was mostly really good and rewarding that it would be fun to work together again, even if it was in a pretty small way.”

Skipper: “I am shockingly comfortable. There’s a slight trepidation, you and I haven’t actually done anything public for quite a long time, so I had a little trepidation, but I come in, I sit down on the sofa and it’s quite comfortable and we’re laughing about Larry Bird and Magic Johnson, and it’s great to see you.”

“It really makes me feel good to figure out some way to pay you exorbitant sums of money again. Quite deserved, it was always deserved before, it’s deserved again, and I think what you’ve done at the Ringer is remarkable and fabulous. It’s a pleasure for me. It’s like a little payback, happy payback, for Grantland. ”

Simmons: “A little bit.”

Skipper: “It’s a little recompense. You know, what you’ve done at The Ringer is really spectacular. You kind of did it again twice. It’s hard to do twice.”

Around 10:55, there’s some significant discussion of Skipper’s previous career, including working for Jann Wenner at Rolling Stone. Simmons asks how difficult Wenner was to work with on a 1-10 scale, and Skipper responds “He’s both, Jann is a one and a ten. If you walk in at the right moment, he couldn’t be more charming, he puts his arm around you and tells you how great you are. You walk in at the wrong moment, he’s difficult, moody. He did ultimately fire me. We share this in common, I was fired for insubordination.”

Simmons: “Is that true?”

Skipper: “It was! I was the publisher of Us magazine, 10 years after I started, and Jann wanted me to do some things which I resisted and thought I knew better than he did, forgetting in my mind that I didn’t actually own the magazine, he did, so I was dismissed.”

Simmons: “I don’t think I knew that part.”

Around the 12:30 mark, they talk about Skipper’s role in launching ESPN The Magazine, including working out a deal with Wenner to use Rolling Stone‘s printers and working out a deal with the U.S. Postal Service to get treated like a weekly magazine despite publishing only every two weeks. Skipper mentions that the magazine was making $30-40 million in profit annually at one point.

This then goes into a discussion of Skipper’s next role, building ESPN’s website, and he cites writers like Peter Gammons and Hunter S. Thompson as big in getting people to check it out. That then leads to him and Simmons talking about Simmons’ early days there. At the 20:30 mark, Skipper says “I’m quite proud of the fact that we were the last home for Halberstam, Wiley and Hunter Thompson. Their last work basically was on. And then we were the first national platform for you. I mean, Sports Guy was national, but you know what I mean.”

Simmons: “That was a big thing for me.”

“The weird thing was being on the same site with all those dudes. Halberstam, Breaks of the Game was my favorite book ever, Hunter was a legend, Ralph Wiley, all those dudes, and leading the page over them, I was like ‘They’re leading me over Halberstam?’ It was hard to wrap my head around.”

Skipper: “Genuinely, sincerely, those guys were really important to us, they gave us credibility, but you were the first guy who connected with who our audience was. Just like all new platforms, it was young, it was kids. At that point it was overwhelmingly male, we used to be like 90, 95 percent male, and very young.”

Simmons: “I remember when we were figuring out Grantland like nine years later, it was kind of the same model, you launch a site with some big names, but the younger people, they’re going to be the ones that carry the site. The big names give you some recognizability and credibility, but people like Dave Eggers and Gladwell, they wrote like once or twice for Grantland but we put them in the press release.”

The conversation after that then dives into subjects like ESPN’s mobile efforts, rights fees and deals with leagues, 30 for 30, the eventual launch of Grantland and more, before going to Simmons’ exit (around the 71:20 mark, discussed in detail here) and then to Skipper’s own exit from ESPN (around the 85-minute mark). But what’s transcribed above is notable for its look at the past, present and future for both Simmons and Skipper.

[The Ringer]

About Andrew Bucholtz

Andrew Bucholtz is a staff writer for Awful Announcing.