WTF with Marc Maron Podcast - Episode 905 - Bill Simmons

Episode Date: April 8, 2018

Writer, producer and podcast pioneer Bill Simmons is a man whose life, career and worldview have changed in real time with the evolution of Internet. Bill talks with Marc about some of the checkpoints in that evolution, including why he walked away from a big break in TV when he was writing for Jimmy Kimmel, why he thinks he was considered ‘difficult’ at ESPN, and why his HBO show wasn't what he thought it would be. They also talk about Magic Johnson, Grantland, Letterman, divorce, documentaries, and Andre The Giant. Sign up here for WTF+ to get the full show archives and weekly bonus material! https://plus.acast.com/s/wtf-with-marc-maron-podcast. Hosted on Acast. See acast.com/privacy for more information.

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what's happening i'm mark maron this is myTF. Welcome to it. Thank you for joining me. If you're new to it, welcome. Make sure you go check out the archives over there on the Stitcher app. You can go back and get them all. Welcome. I am broadcasting from the new garage, and I'm happy to say that the garage has been christened by tears. It happened. I don't even want to mention the guest because it actually didn't happen on Mike. It happened afterwards after a conversation where it got a little emotionally overwhelming. But tears have been shed here in the garage, and that's good. It needed that. It needed that sort of like breaking the champagne bottle on the ship's hull before it backs into the ocean. Now we have coronated. We have blessed. And this garage seems to actually have a bit of magic of its own.

This is an old house that I bought. And old houses tend to have magic if they've been around a while. I'm not going to say there's a ghost in the house, but there might be. There might be. Things have been moved. Things have fallen down and broken. So as long as I can breathe properly and no weird chasms to strange worlds open in the house,

I think I'm okay with the ghost. Maybe we can negotiate some sort of way of living together. This house was built in 1908, folks. 1908, and it's still solid, still beautiful. Getting a lot of emails. You know what? Let me first tell you that Bill Simmons is on the show today. Bill Simmons, a podcaster, a writer. You can get all his stuff at TheRinger.com. He had me on his show. Now I'm having him on mine. We're often mentioned together in articles about podcasting at the beginning.

We're very different. We have different focuses. You know, he respects me. I respect him. For me, a guy who knows nothing about sports but understands the passion. Understands it. So that's coming up soon people are emailing me asking me how the cats are adjusting to the new house are you fucking kidding me they've never been happier in their life they're not like i my old house folks honestly was 929 square feet this new house is bigger i'll leave it at that it's bigger and

these cats have they've made it they don't even think about going outside that's how comfortable they are they can each have their own room if they'd like they can sweep in different places but buster kitten is still kind of a fucking asshole and persists on beating up old man monkey and old lady fonda uh i i don't know what to do i'm not getting another kitten so he can have somebody closer to his own age to play with but uh but that's what's going on they're they're very happy they're eating they're they're healthy and uh they they seem um they seem better than they were at the old house maybe that old house was possessed by a lot of emotional baggage and, and memories

that weren't so great for the cats or myself. Maybe I'm telling you folks, I'm not, I'm not regretting, uh, leaving the old house. And, and that's, that's a lot to say because a lot happened there. I was very comfortable there, but I'm really, I'm really in this and I'm having, I'm having a hard time. You know, I need to put some time into putting this room together. And knowing me, that could go on for years. Like I went through a wave of, I moved all of my stuff from my house over here and spread it out as best I could. Really, I need more stuff.

I don't want to get just any stuff. I need more stuff. So that's going to start to unfold over time. I don't know how long it'll take.. I don't know how long it'll take. And I don't know how long it'll take to get everything in this garage that I want. But I do know I'm happy to be here. The other thing I wanted to talk about is that I neglected to mention that last week, what night was it?

Last Tuesday, that I did a show with Dean Del Rey. Dean Del Rey put on a show with a bunch of rockers. It was an evening of comedy with me and Dean and Joey Diaz and Bill Burr. And then there was a band and that band, including me sometimes, including Bill Burr a little bit, but Scott Ian, Nikki Sixx, Rudy Sarzo, Michael Devon, Josh Z played guitar, Steve Gorman played drums, Billy Rowe played guitar. And the album, here's the thing, the album that we did was all of Powerage.

That was the night. We did a stand-up comedy show and then they played Powerage straight through with a couple of other songs. And I got to sit in on Down Payment Blues, which, as some of you know was the original theme song for this podcast until we started to get panicky about it and we pulled it but I also used it on my old radio show it's one of the best songs ever Down Payment Blues by

by ACDC and I got to play that and it was pretty exciting it was me Scott Ian, Billy Rowe, that and it was pretty exciting it was me scott ian billy rowe um josh z dino singing uh mike devon michael devon on bass and uh and steve gorman on drums and i was uh i was i was elated it was fucking great man it was fucking great i guess i'm just reporting that i had a good time would that be is that okay is that okay i i had a great time i'm gonna i've decided to have more good times in my life but uh you know i don't want to sound too chipper god forbid i do want to you know make sure everyone knows i am going to be in europe next week my shows in london oslo stockholm amsterdam and dublin get tickets go to wtfpod.com slash tour also i wanted to give a shout out as they say in the game to uh the woman in my life sarah kane who has an opening

this is one of the reasons we plan the trip like this she has a big opening at the Timothy Taylor Gallery in London next week on April 18th. So now, it's my pleasure to share a conversation I had with Bill Simmons. Many of you are fans of Bill Simmons. Great podcaster, great writer. Everything is available, both his writing and podcast are available at TheRinger.com. And also the documentary Andre the Giant premieres on HBO tomorrow, April 10th at 10 p.m. He produced that and it was his concept and it was a hell of a story. I enjoyed it a lot and I didn't know about Andre. And as a guy who's involved in wrestling

in a peripheral way, I needed to know more about Andre the Giant. So it's a pretty touching documentary. So this is me talking to Bill Simmons. It's winter and you can get anything you need delivered with Uber Eats. Well, almost, almost anything. So no, you can't get snowballs on Uber Eats. But meatballs, mozzarella balls, and arancini balls?

Yes, we deliver those. Moose? No. But moose head? Yes. Because that's alcohol, and we deliver that too. Along with your favorite restaurant food, groceries, and other everyday essentials. Order Uber Eats now. For alcohol, you must be legal drinking age. Please enjoy responsibly.

Product availability varies by region. See app for details. Death is in our air. This year's most anticipated series. FX is in our air. This year's most anticipated series, FX's Shogun, only on Disney+. We live and we die.

We control nothing beyond that. An epic saga based on the global best-selling novel by James Clavel. To show your true heart is to risk your life. When I die here,

you'll never leave Japan alive. FX's Shogun, a new original series streaming February 27th exclusively on Disney+. 18 plus subscription required. T's and C's apply.

I don't really do podcasts. Turn it so it faces this way. That's good, yeah. That's better. Can you see me all right? Yeah. You don't really do podcasts? I don't really do podcasts. Turn it so it faces this way. That's good, yeah. That's better. Can you see me all right? Yeah. You don't really do podcasts? I don't.

Why not? How come you're not part of a... We should talk about this on the pod. We've been on going for five minutes. Oh, all right. I don't know how you do it, but that's how I do it. I didn't know we started. Yeah.

I just turned it on. You never know what's going to come up. No, I don't. Sorry about the noise, but that's how I do it. I didn't know we started. Yeah. I just turned it on. You never know what's going to come up. No, I don't. Sorry about the noise. I'm trying to make tea here. I've got the last vestige of the kitchen I once had in there. It's this boiling pot. Spoiler?

Yeah. The cool thing about this garage is it feels like I could be in any state in America. Yeah. It could easily be in Minnesota, like on some ice fishing lake or something. Sure, man. If that's what it takes, if you need to picture that, to make this feel more comfortable,

being a UFO. Yeah, we could be anywhere. It is a classic sort of a type of... I'm wary to call it a man cave, but it is a type of sort of a post-hippie man cave. I am, since you were in my office i'm really happy with my poster game i did some poster upgrades oh i'm really happy with how the symmetry of how they're arranged which is really proud of it a couple good ones yeah an old springsteen

1975 capital records are you big are you a big springsteen guy i i really was do we talk about that we on yours we didn we talk about that on yours? We didn't talk about a lot of stuff. We have a lot left on the- But did you listen to my Springsteen? Did you listen to my Springsteen? I did. And how was that as a Springsteen fan for you?

You can be honest. You can be honest. Now, for me, it's weird to hear Bruce talk about himself because his songs are so personal. Yeah. So it's almost like you partly think you know all the answers, and then he has answers that you don't think he's going to have, and it's disorienting.

It's almost like if I heard my wife on your podcast and she was telling you things that I didn't know, and I almost take it personally. That would happen. It probably would. She's very excited that I came here. It's happened with other people before, like brothers of people, spouses of people. Oh, yeah.

People who have known people for 30 years. I didn't know that. Yeah. Because there are weird little details about your life that why, even if it's your spouse, I mean, how's it going to come up? He's very transparent. Bruce. The live, the three album box set or whatever it was that came out in the mid-80s.

Yeah, I like that one. And it's got a couple of those stories that he tells. He's like, when I was growing up, my dad. Yeah. And basically the theme of everyone is his dad hated him. But then it would take a car accident or him not getting into Vietnam for his dad to actually realize that he's okay for five minutes. Yeah. And you just feel like crush for the guy.

Well, yeah. What struck me about him was just like how hard he is on himself. Yeah. And how dark it kind of got. And I'm not a fanatic for him, but I felt like I look back at it as one of the great events of my podcast. Oh, yeah. Going out there.

I'm sure it was. And just being around him. But I'm not like a guy who's, I've never seen him live, really. I've never been fanatic, but helps you know what i mean and i read part of the book but like when you're around him you're like there's a weight to him you know it's real i saw he was the second concert i ever went to yeah and the first one i went to was bob seger who also was long oh yeah that was 1980 and the second one was bruce and he kept playing encores for four hours yeah was the stereotype, but it really was the case of like, we're at like the three and a half hour mark and he's like, coming out again.

Where'd you see him? It was in Hartford. I think it was the Hartford Civic Center. Yeah. And the crowd was like, oh my God, what? Oh, sorry, two more. All right. He just outlasted the crowd.

He wore out the crowd. It was pretty great. So I watched the Andre the Giant thing last night. You did? They sent it to you? Yeah. Oh, cool. I watched it.

So let me understand something. Yeah. Because being not as sports-oriented at all, I think you probably are responsible in some way for sportscasters and sports radio now to be more broad-based. I think that you, because of what you've done. Like now, if you're on the road or something and they're sending you to a radio show, they're like, it's sports. But they don't talk about sports.

I think that's your fault. I'll take it. I'll take it as a compliment. Well, you know, you kind of reconfigured what a sports guy can do in a public medium because i've done a lot of sports because you walk in you're like they look like sports guys but they're like hey what's up you know let's just talk about whatever right i don't think that happened before you no i i came at a really weird time it was it was very early on in the internet i mean super why, but that's like that.

And it was just people, the way they wrote and talked about sports, it was one way. Everybody had their two newspapers or their one newspaper in their local town. Yeah. USA Today. Right. And then sports radio was just starting to really come into its own, but not really. But it was- And that was it.

And everybody did it the same way. Right. It just complete like shop talk. Yeah. it it was everybody did the same way right it just complete like shop talk yeah my whole thing was you know i was on my own for four years just writing for this site that i had created and trying to figure out what worked and didn't work what the when you were on aol when i was in boston yeah well let's go back so and then i wanted to start with andre because you know i i it was an interesting choice because i know you did that you sort of masterminded the 30 and 30 on espn yeah and that

like i i have to assume that you were gone by the time they did oj made in america right i was in there for the early stages of it actually because that seems to be the sort of like the the this the what you were headed towards yeah and we knew it at the time we felt like after we had done volume two and gotten that going, and I remember the guy that I created with Connor Schell, we were driving back. We were at some million dollar arm of screening. But you're still working at ESPN. Oh, yeah.

This was like 2013. Yeah. That's when they started making the OJ doc? That was when we were thinking about it. And the big thing for us was we hit at this point with 30 for 30 where everybody just liked it yeah and it wasn't always great yeah and you kind of know that and people another great one and we're like yeah that was like b minus oh really and some of them didn't work in your mind no it's you know it's like anything else you have some great ones you have

some good ones and you have some but the premise was you would do sports like real documentaries and use real filmmakers. You use real filmmakers, but more importantly, use stuff, do concentrate on stuff that had happened in the last like 25, 30 years. That was the big inefficiency when we launched it,

which was HBO is doing Joe Lewis and Vince Lombardi and all these old guys. And it was like, we want to wanted to fab five and um but when by the time the oj thing we started you got to move it all up to date because you're almost an old guy yeah well it's funny is we had we had wanted to do oj in the first series and it was it was still too close and it was like for you can't do that story in an hour so we ended up doing was and you can't do it just about sports. No.

So we ended up doing. If you did a documentary just covering OJ's sports career, a new one, that would have been insane. Yeah, people would have been like, what is this? What about the part where he murdered people? So we did a whole thing about the day of the car chase. Yeah. And it was an hour and it was all the different things that happened on this day. And that was in the first volume. That was was really all we could have done with that story but then

after five years it's like hey how do we blow this out and the initial idea was three parts five hours oh and then it turned into what 10 parts no it was five parts he as we're probably ended up at seven hours but he took it i mean i i was there when he sent us the treatment and then we pushed it to you hired hired Ezra? Yeah, because Ezra had worked for us on the Big East. He did the Big East documentary. He's just really talented. He's great.

I talked to him about the OJ thing. I still have his treatment. It was two paragraphs. Oh, really? It was like three parts, five hours. This is what I want to do. And it was like, yeah, okay. This is what I want to do.

I want to take on race in America going back to the beginning. Well, it was race. It was celebrity. Celebrity, yeahica going back to the beginning well it was race it was celebrity so it was uh sports and then it was also a legal case and you know initially though the first multi-part one we want to do was tyson and i i was always fascinated with tyson week like shark week yeah it was like tyson week monday and just like tell it that way yeah and by the time we actually got around to seriously thinking about it he he was like too available and to see yeah he's out there he's doing Broadway plays books and it just didn't make sense to hang around at a cigar place across from the Comedy Store and sunset

yeah just like yeah he's available he just seemed like we it just didn't seem that special as right in like 2009 right as a Right. And that's when people's opinions of him were rightfully tainted but there were still a lot of people that had normalized him. Oh yeah. Yeah. But I mean what Ezra did with the OJ thing I think it's the best documentary ever and I also think like

it's really hard to follow that and I'm friends with him and I'm waiting to see what he does next. He's so smart. He understands like whatever he does comes under the shadow of this amazing achievement. And that's really paralyzing sometimes. But you weren't there for the follow through of it.

I mean, I wasn't. I was there from when we got a green light, when he went off and started working on it. But the thing with the good thing about people like ezra is they just kind of go off if somebody's really good at doing a documentary and jason hair for andre the same thing they just kind of disappear and it's almost like they go into witness protection and they dive into the footage they read everything yeah they live and breathe it and they become obsessed with it and that's i think that goes for a lot of things but especially documentaries the good ones are like we we had this problem with the first volume of 30 for 30 where we do certain people yeah and it was just part of one of seven things

they were doing right it's not gonna work it's gotta be like this is all i am doing all the time yeah because and it's a solo journey because so much of it is found footage and organization and creating a narrative. Interviews. Who do I interview? Who's good? Yeah. I'm sure it's the same thing when you do a stand-up special. It's like you can't do a stand-up special as one of the seven things you're doing.

Like you're all in. You're testing material for weeks and weeks. You're writing constantly. Sure, but at night, you know. I mean, you know, you're sort of – you can do other things. It's not as all-consuming because I don't have to book out a few hours during the day. Yeah, I guess that's true. But it's the number one thing in your mind.

Oh, yeah. Yeah, I'll book out a few hours a day to talk to myself. Right. Get on the mics with me and figure out where I'm at. Yeah. Work some material. It's really hard to do a documentary because- I love it.

I don't watch enough of them. Yeah, and it's frustrating because i did so many that i can watch them now know exactly what's right what's wrong what they should have done where the turn happens where like oh it's getting sad now well it's now i don't know what to think that moment true no but the biggest mistake people make is they keep too much yeah and people the directors fall in love with what they did so first of all did you were you pissed off that you didn't get to follow through be there for the whole oj thing or did that you left him in the middle of it no espn no it was already on i was not pissed off about that

because it was ezra's thing yeah our job was to get the series to the point where we could do something like that right to recognize somebody who's as talented as him and to give them the chance to do it and that was the last of you and ESPN yeah pretty much but when I was leaving he was working I mean I heard he'd we'd heard a couple different stories from when he was you know kind of preparing it and doing the interviews and stuff yeah then I knew I mean I knew it was going to be really good i didn't realize it was going to be great anybody who realized it was going to be or claims they thought it was going to be that good is is lying yeah it was the it was ezra going from like

one level his career to another level which happens right or usually i think you i don't think he's maybe in his late 30s or mid 30s oh is there is there actually a chart you i don't think he's maybe in the is late 30s or mid 30s oh is there is there actually a chart where i don't know the age syncs up i think he had done enough projects right it was like because i was way late on that chart yeah i think both of us were just starting to tip up now there no but i think you hit a point where you kind of you kind of know what you're doing yeah right and and i think also he had, like he must have had that moment with himself where he knew it was getting bigger and he could manage it

and it was worth following it. Yeah. Like once it started, it must have just started to open up to him at some point where he's like, this is all layering up and I'm covering all this stuff and there's no reason to stop.

There's no reason, right? The other cool thing is it's the best documentary subject I think you could really ever do, at least for sports, because it wasn't really about sports. The bad thing is I think it's convinced a lot of people, like, oh, you should do a,

this will be like the OJ thing. And it's like, this was like a special topic that hit so many different things and went in so many directions. You can't replicate this. It always happens with executives. They're like, they just, they so easily go like, no, just do that.

Yeah. You know, like- Make it four hours. OJ was four hours. That was great. Guess what? Documentaries should not be four hours. And this was an exception.

But so the Andre the Giant thing, this was like something you've been working towards for a long time? Yeah. When we came up with 30 for 30, it was on the original list. And it just, the WWE wasn't ready to outsource anything, especially him, because he's one of the biggest stars they ever had. But this is interesting, because now you're kind of doing it at HBO, who you have a big overall deal with of some kind. And this is your first documentary with them. It was one in 2015 of it was the first

one i wanted to hbo sports and this is a wrestling show yeah but it's it's not really about wrestling it's about this it's about a giant guy no it is right but it's about who knows he's gonna die yeah no i get that yeah but the form is wrestling it's not football it's not basketball it's not you know soccer it's not like and i'm not basketball. It's not, you know, soccer. It's not like, and I'm not saying, I'm certainly no longer in a position to say that wrestling is not a legitimate sport. I know. People get mad. No, but I'm on a wrestling show.

So I've had to learn, you know, and I certainly have respect for the form, but it's fundamentally about, you know, a spectacle, an entertainment. Right. But so it didn't really matter. You still, as a sports guy, were like, it's important. Andre's important. Yeah, because I felt like when I was growing up, he was one of the biggest stars we had.

But were you a wrestling kid, obviously? I was. I got into it probably when I was around 10. 10? I was the only child, so I was ready to get into anything. What year was it? So we're talking like 79, 80, somewhere in there.

I remember Andre Killer Khan broke his ankle. Were you a latchkey kid or did you have people around? What is a latchkey kid? Like by yourself in the house? I was there in the days. I really was. It was a different era.

I used to walk home from school. Right. Let myself in. What state are we talking about now? Massachusetts. Like what town? It was Brookline. where in Brookline Chestnut Hill oh okay up off route nine yeah uh-huh yeah but it's different there you walked home from school yeah like how old are you I'm 48 now I'm 54 all right so right yeah you didn't have to be afraid sometimes it's snow you walk home in the

snow we had the blizzard it was just we were the blizzard. It was just, we were out. Blizzard is 78. You just go out and be parents to you in eight hours. Yeah. We used to go to the dump and look for Sports Illustrateds and Playboys. Did you find them? Yeah, sometimes. Where was the dump in Chestnut Hill?

The Brookline Dump. It was a long walk. Yeah. You remember where the Chestnut Hill dump was? Yeah, we would go. I was like, let's go find some stuff. What were you doing in the, you were the only non-Jew in the world of Jews up there? I actually, I will say I went to a lot of bar mitzvahs in the seventh grade and did

not really fully understand it. Yeah, it was a different time. Chestnut Hill Mall. Oh, the Chestnut Hill Mall was incredible. I remember. They had a toy hobby. They sold the hockey cards and the basketball cards. Oh, that was your place?

Yeah. My best friend, Reese, I've written about this. We used to steal change from the fountain to buy cards. Oh, really? So we would hold each other. I think I was taller than him, so he would hold me and we'd reach in and grab quarters and then go buy hockey cards.

But yeah, those were the days, man. Now it's like you can't, your kid's going anywhere and it's like you have Obama. Yeah, you got full security. How's Zoe getting to school? Your grandmother's taking her and then they're picking her up at 3.15. How far is the school though? It's like 20 minutes. Well, like in Chestnut Hill, you could probably walk it, right?

Yeah, there's a lot more walking. Yeah, I remember that. It was fun because you'd have your friends and sometimes you'd just walk. Yeah, and just keep going. There was more playing. It would be like, oh, the guy in the next street, there's him and he's got his two brothers. Let's go over and play hockey all day. And now I think it's moved more toward video games, Instagram.

They can relate to people that have seen them. Yeah, kind of. Can they? In a lot of ways, yeah. But you don't get the feeling. You don't get the sense, their vulnerabilities, the humanity of the person,

the competitive nature when you're doing an actual game is different than a video game. I agree. When you're bullying somebody, you stop. Hard harder and easier well it's easier now but because you don't see the guy about to cry right you know back when you were just a shitty bully as a kid you're like oh no he's about to hey buddy i'm sorry hey bad yeah the uh

the the instagram i was a bully and i've been bullied i wanted to say i've done both sides i think everybody's been on both sides of it. The Instagram, that whole world is really, I have a 12-year-old daughter, 10-year-old son. So watching how they interact. And fortunately, my kids both have people skills. But just the little games with Instagram is really crazy. I have no idea. I don't have the kids.

With the girls and if somebody's not in the group picture because they all went to the mall, their feelings are hurt. It's like, it's this whole more elaborate way to hurt other people's feelings that you really have to be careful of. I can't imagine what it's like to have kids

and have to explain to them something. I will say that I had close to me on my podcast the other day and we were talking about the Parkland kids. And how sophisticated they are. Yeah, very. With their kind of children of social media who are actually the first ones that understand how to harness its powers and mobilize.

Yeah, and also want to do that. Yeah. Organize. I don't know. Yeah, it's kind of fascinating because this assumption that millennials are just these useless, self-involved idiots. They're not. They're really smart. I have a lot of them that work for me they work really hard and they're really smart and they're just

different than the generation that came before them but your generation was different than your parents and yeah these but this is what happens right but the fact that they you know they organized in real time with each other to do something politically relevant uh it was sort of like oh maybe there is hope there's this glimmer that maybe there is hope and also the way they handle trolling and stuff where it's the first generation somebody comes at them and they'll just cut the person's knees off almost like a comic at the comedy store where they're like oh you're gonna heckle me yeah boom and they raise the stakes yeah yeah my i'm i'm gonna i can't handle the trolling i'm

too sensitive for it like i really am like i really like you know it's if i'm so you get heckled even now and it's heckling is different if i'm on stage i can eviscerate somebody yeah but like just the sort of anonymous nobody right you know on twitter you're taking you know because you can't really defend yourself because you're going to get into a clusterfuck right you know that it's not they've already won just by you reading it yeah yeah as soon as you respond it's over but in a club you know you get a laugh or you just knock them out it's easy you know it's different different dynamic yeah so how long does it take to learn how to cut their knees out some guys don't uh don't do it at all you know some guys some guys don't, you know, it's not important to them to sort of

nurture that skill. I think it's important. I did it innately because, you know, crowd work is fun. It can be funny and you have to be able

to defend yourself. But some comics are like, God, they won't engage with it. I'm always amazed and it's something like, obviously,

I worked with Kim a long time ago he can handle himself when we were launching the show yeah and he could but it took him I don't know how many years

in act one to learn what to do when a joke didn't work which was Carson's like greatest skill right Carson was always just that weird beat

he was the funniest when a joke failed yeah that's when it became funny yeah because he rode with whatever and he made fun of the audience yeah and Kimmel it took a while oh yeah just to get the reps of oh that didn't work the way I thought and they reacted this way I'm gonna twist this and still make it and still

save it and now he's the best at it well all those guys yeah I think he's very good because he can sort of really handle like um uh trolls you know what i mean like he like he likes online and stuff he's very good at handling trolls yeah like because they they kind of creep me out yeah he he he is very aggressive yeah of it which i think is an interesting way to play but it's working and also he's very emotional now he's sort of grounded in an emotional place and he's being very honest. So let's go back. Chestnut Hill, you're like an only child. Yeah. So where's your mom and dad?

I think he said only child like I was like in the- Like a weirdo? Yeah, in the army or something. Well, they kind of freak me out a little bit because I always assume- I'm freaked out by only children. Yeah? Well, I always assume that like, and I'm always proven wrong, that there's an inordinate amount of pressure on the only child you know in a sort of subverted

way from the parents because you're the only shot they have like yeah i think that's part of it and i think there's a little narcissism that kicks in because kind of the world revolves around you to some degree yeah it's i i just watch watch, like what my daughter and my son, like watching them interact, that it's so important that you kind of learn, you have to learn, it sounds like a cliche,

but you learn how to share. Yeah. You learn how to get your feelings hurt. Yeah. Like they're super mean to each other and then it's fine

and they just, you develop kind of a thick skin. And you didn't? Well, you're an only child. Like everything is new and especially like back then, you don't have the internet or anything like that, and you're learning how to interact with people

either at school, family functions, or when you're out, or just from TV and shit like that. And TV had a huge impact on kind of every thought I had growing up because I watched a lot of TV, and I felt like those characters were my friends. And your your parent where were your folks my parents they got divorced when I was nine and eventually but like two two years later my mom moved to Connecticut yeah so I lived with my dad

for a couple more years what he did was like Kramer versus Kramer uh he worked in a school system eventually he became a superintendent for a long time. Oh, yeah? Main guy? Yeah. Overseeing the whole system? Yeah. Massachusetts? Superintendent. Not just an intended, a superintendent.

Was he a Massachusetts guy? Yeah, he was. Did he talk like one? He's been there almost 50 years now. Yeah, it's funny. He's got this, he can't say certain letters anymore, which is like a Boston thing. Like L's and R's are really tough.

It's just the L's are gone. Like we've had- Ah. Like the Portland has this guy, Damien Lillard, and my dad won't even try to say his name. He just calls him like Dame. The guy in Portland, Dame. Yeah. Lillard's like, no chance.

Both of your folks are around still? Yeah. That's nice. Yeah. All right. So you're in Massachusetts for a little while, and then your mom takes you to Connecticut. How old are you? Yeah.

So I go there in eighth grade, which was tough. Going back and forth every other weekend to see my dad in Boston. On the train? Still going back. Yeah, by yourself? Yeah, check. See, you could do that. Buy the New York Post.

Have a book. Get some roast beef sub. Take the train. And I tried to get there in time for whatever the Friday night Celtic game was, because Larry Bird was playing back then. We had season tickets, so I was like, a lot of it was like, oh yeah, I'll go back this weekend. Then Friday game, Sunday game, I'll get to see two games.

And then eventually I was able to drive when, you know, back then it was 16. What is it now? I don't know. I was 15 in New Mexico. I was 15. So when I got my license, I could just zoom back and forth and go back for games.

From Hartford to? It was like, it was, it was Stanford. Two and a half hours? Stanford? Two and a half half which i always tried to make in two and probably should have died yeah at some point yeah i drove those roads so much i'm the mayor man the mayor was like remember that video game pole position yeah yeah hugging the turns oh yeah because that was the quickest way yeah so all right so you're running back and forth you're taking the train by yourself and then like so it's all sports with you all the time? I love to write.

So I was always, I love sports and I like to write. And eventually it just kind of collided when I was in college. Yeah, you started what you, like you. I started, I had a column the senior year, the last year I was in high school. I went to Holy Cross in Worcester. Worcester. Worcester. Is that a good school?

It is a good school. But when I went there, it was very sports heavy. And they still had, they were kind of weeding out the scholarships as I was there. But when I was there, it was very sports. And there was a lot of the guys there were guys who were good in high school. And there was a big intramural scene. It was just different. Why that school?

You applied to that? You got a scholarship? My dad went there. Oh, he did? Yeah. So you were a legacy? My dad and two uncles. And I really wanted to go to Georgetown.

I didn't get in. Oh. Yeah. So this is the one you got in. Every time I hire somebody from Georgetown, I always get excited. I'm like, I hired a Georgetown person. I just hired somebody with the jersey. I was like, yeah.

What was it about Georgetown? Look at me now. I just, somebody with the germs. What was it about Georgetown? Look at me now. I just did Georgetown. Now they're working for me. I got a Georgetown person. No, it's tough though. I wanted to go there because they had great basketball and I liked Washington. Yeah.

And I just kind of got my heart set on it. Washington in terms of the city or the- Yeah, the city just seemed cool. Were you interested in politics? No, not at all. Yeah. You just liked Boston. When I went to college, I wanted to be- It's kind of like Boston. No, not at all. Yeah. I actually, when I went to college,

I wanted to be, it's kind of like Boston. I want to be a sports agent. Oh really? I did. Uh, I, my first major I think was,

I don't remember if I settled on it, but I ended up doing poli sci. Yeah. Yeah. That's, I, that was my first one. Did you,

so you didn't do well in high school. You did all right. Not good enough to get into Georgetown. I was one of those like high SATs, but didn't have good study habits person. Yeah smart but not motivated did you get the teachers tell your parents that? Yeah he's a gifted writer I just wish he worked harder there's a lot of that. It would be nice if he turned assignments in on time.

Yeah so in college it all kind of fell into place because I didn't write. Did you write for the paper in high school? I did the last couple years, but it was different. I didn't know what I was doing. In college, it was like, I saw the column I wanted, I went in, I badgered the guy to let me try. I wrote the first issue the first year, gave me a column, it was called The Ramblings.

Yeah. And I wrote that one and it was good. And from that point on, I never missed all four years. I wrote a column every time. And I used to, on Fridays. Was it weekly or daily? It was weekly. The newspaper came out on Fridays and I would go to the cafeteria to get food on Fridays and I would see people reading it.

And I was like, yeah. You know, it's like anything else. You're like, you know, when you're good at something, you really, when you feel, especially like somebody like me, I'm an only child. I don't know what the hell's going on. And I'm like, I know I'm good at this. Yeah.

And you just kind of, that's like, I want to do this. And did you get another, it's sort of, it's sort of like the Andre story. What else is he going to do? He's a giant.

What else is he going to do? Yeah. It is a little like that. Yeah. It, it wasn't a huge campus, but it definitely started to have an impact. And I started feuding with the guy who ran the,

uh, college was named father Brooks. Yeah. So I was calling him father Crooks. started to have an impact and I started feuding with the guy who ran the college was named father Brooks yeah so I was calling him father Crooks in my column and uh and who's the other guy oh it was like father Markey I was calling him father malarkey yes they were they were getting rid of scholarships I was calling father Crooks and father malarkey so you starting shit I was starting shit and I got called in once and i was like this is good this is let me get paid for this the power of journalism yeah it was good though it was fun and at some point i just realized i think i could do this and get paid for it but taking a position

like those seem like that you were you taking a position politically on campus were you were you actually other than just calling them names, were you? Yeah. Back then when you wrote sports columns, it was a lot more abstract and you would have more fun with it. Now it's very first person, here are my feelings. Sure. Here's my take. But didn't you do that? I did some of that.

But back then, part of the art of writing the column was to try to mess around with it and come up. Try to say what you were saying, not in the way people would think you were going to say it. So I created characters for them and did that whole thing. But you seem to like to start shit. Yeah, sometimes. I would like to start shit when it's justified. To me, it's like there's two types of people who do this, especially now. It's the people that start shit just to start shit.

Right. I think a lot of local sports radio hosts are like that. Yeah. But I think when you start shit, if you really believe what you're saying, it's a little different. Yeah. And I always try to,

whenever I'm writing or talking on a podcast, to me, it's got to be genuine. And it's always how I feel. I might be wrong. I might not have all the facts that I needed when I made the assessment. Right. But I genuinely feel

that way so you started your so your style started to unfold in in college or not quite yet no in college it did because i was trying to write a little bit from the fan perspective and and and meld that with some other things who did you like reading like journalistically it was all kinds of people but this hunter s so when i was in Boston, they had these, we just randomly had a couple of awesome sports columnists, Ray Fitzgerald and Lee Motville. And they did not write the typical sports column. Who were they writing for?

They were writing for the Boston Globe. Yeah. And the columns that they wrote were basically thoughtful, a little bit from the fan's perspective. They weren't stuff like, Carlton Fisk is a coward and needs to go. They didn't write that stuff. So it was a little bit of that.

It was other, Roger Angel and the New Yorker, the way he wrote from the fans' perspective was a big influence. I don't know if you ever read a book. William Goldman wrote a sports book with Mike Lupica. William Goldman's the famous screenwriter. And he wrote from the fan side and Lupica wrote from the reporter side.

And it was about this year in New York sports and Goldman's fan columns. I basically just started ripping off like that style in college. Like I was like, that should work as a column. Yeah, and no one was doing that though. Nobody was, not really. It was just part of an experimental book in a way.

Yeah, and then the other thing, I was sprinkling a lot of pop culture because it was working for Dennis Miller.er yeah so dennis miller was the weekend update guy yeah and i would watch the weekend update and you would have like just these random obscure pop culture reference jokes that i just thought were like the funniest things of all time yeah you know i remember there was that one about blah blah blah it's like playing stratego with the lander sisters and i was like i get that that's a great show yeah right you've got in on it because yeah work those in you still feel like you had to be a little smarter than the average knob to get them yeah i mean like the thing about dennis you know he wasn't necessarily

my cup of tea but you had to be impressed with the lyricism and how many references he could get in and then sometimes you're like i don't even know what that is yeah i gotta go look that up i gotta to be impressed with the lyricism and how many references he could get in. And then sometimes you're like, I don't even know what that is. Yeah, I gotta go look that up. I gotta learn something today. Well, and then when somebody gets it, it's a, I remember I used to do this one liner thing.

Yeah. So it was basically, it was a column of one liners, which now would basically be, I guess, Twitter. You wouldn't even need to do it. Yeah. And one of the lines was about the three-part Hawaii Brady Bunch episode when- The mask.

When he found the weird magical- Yeah, the Tiki guy. Vincent Price kept the kids in a cave. Yeah. He kind of kidnapped them. Right. And then Mr. Brady and the Bradys, they found the kids. They freed the kids.

And then they kind of felt bad and they invited Vincent Price to the luau. Right. And I was just like, why the fuck did they invite him to the luau? He should be in jail. He kidnapped their kids kids so i did a throwaway line in that and then at a party that night a couple people like been surprised man that was some good shit you know i was like oh good somebody got it so you just kind of don't know so you kind of like you you like the uh the attention and but you were but also you're you land in jokes. Yeah. You don't know what's working.

Because the stuff that really landed was the actual columns. And if you took a take on something, or you read about Mike Tyson, or what Holy Cross was doing in their sports, or whatever. But the little throwaway lines, I always noticed people would mention those. And then when I finally- The grabbers. Yeah. And then when I finally had my own website a few years later, I started, one of the things

I knew I wanted to do was a mailbag, which I hadn't really seen done successfully as a sports column. And it was completely 100% ripped off from viewer mail. But it was email at that time. Yeah, it was like- At the very beginning. It was like, send me, yeah, early email. I was writing for an AOL only site and it was you know here's my aol address send me an email

i might answer it in my mailbag right but it was ripped off from letterman sure but they but letterman didn't invent that no but i grew up as a kid in the 80s i revered letterman and sent him viewer mail things and watched every thursday night hoping he would pick mine he never did never did but so okay so you do undergraduate at Holy Cross and you're studying political science. Yeah, poli-sci. But you're just doing mostly your preoccupied writing. You do okay in college? I finished with a 3.0, which was a miracle.

That's pretty good. I had a 2.5 after freshman year and my dad wasn't there. Did you get along with him? With my dad? Yeah. Oh, God, yeah. That's good. Yeah, he's my buddy.

I actually made him, as my column evolved, he became a character in the columns pretty much. Did he like that? I think he did, actually. Yeah. I think he kind of enjoys it now, especially because he's retired. I have him on my podcast sometimes. Yeah.

He's like stereotypical old, crusty Boston fan who's strangely hopeful but upset about stuff. Yeah, yeah. I have my dad on, hopeful, but upset about stuff. Yeah. Yeah. I have my dad on too, but it doesn't always go. It depends where he's at emotionally. It's tough.

Cause you're always going to enjoy your parents more than anybody else is going to. Yeah. Cause my parents are genuinely as endearing as they are. They're a bit disturbing. Well, that's what the one I want to have on is my mom and she refuses to come on.

Cause her, like her, her pop culture choices oh yeah her favorite movie ever is sex lies and videotape which is that's a weird isn't that weird my mom's super weird that's pretty good though yeah my mom's got a lot of weird hobbies and soderbergh's first movie i know she's just like you it's the best and but she has a lot of takes and she would be unbelievable on a podcast, but knows it and refuses to come on.

She's kind of my great white whale right now. Oh, really? Getting my mom out of my pocket. What other things is she into that's odd? She's obsessed with wine. Right now she's watching- With wine? She watches all English shows on Netflix and Amazon and Hulu,

anything that's English. But then weirdly went to like subtitle shows and she's like, I just watched this amazing Italian drama. And I'm just like, what are you talking about? What did she do while you were growing up? What was her job? What was her world? She was, initially she was a teacher slash social worker.

And then eventually just got remarried and became a mom. And then after I went to college, had this whole run as like the manager of a jewelry store in Greenwich, Connecticut. And I don't know. She's had a lot of lives. Doing the older lady business thing? Yeah. Well, she wasn't that old at that point.

Eventually got older. But yeah. And did that marriage last between her and the next guy? A while. Yeah. 30 years. He's your stepdad? Yeah.

Yeah? Yeah. Huh. Like that guy? Yeah. All right. I like everybody. Come on. You don't. You don't. 30 years he's your stepdad yeah yeah yeah huh like that guy yeah all right I like everybody dude come on you don't

you don't you can't is this where you're trying to get deep on me no I'm not trying to get deep I'm just curious I don't come from that I don't come

you know like the story's like I know that divorces my parents get divorced when I was 35 so I didn't have to deal with that you know other than you know in sort of hindsight or as a grownup.

But I've talked to a lot of people that it affects them one way or another, it doesn't, or they don't think it does. But step parents, I can't imagine, it must be just weird and difficult. I'm fascinated by kids that divorce, and I have a couple friends now who are divorced who have kids.

And I've talked to them about it, because I was like, here's what happens when you're the kid of a divorce. You have a couple friends now who are divorced who have kids and um that i've talked to them about it because i was like here's what happens when you're the kid of a divorce you can tell them you can yeah i was like you're gonna play your parents against each other you're gonna learn how to you're gonna learn two things you're gonna learn how to lie to your parents you're gonna learn how to lie to them to make them feel better about things that they you it feels like it might hurt their feelings that they found out. Yeah. And then you're going to play them against each other to get what you want.

And it really turns you into like kind of a devious person. But not, it's just instinctual. Yeah. Well, it's weird because, especially if you're an only child, you're like in the power seat. Yeah, of course. Which is ridiculous. It's all about you.

I was like nine when my parents got divorced. Yeah. But yeah, divorce, depending on when somebody gets, how was like nine when my parents got divorced. Yeah. Yeah. Divorce, depending on when somebody gets, how old you are, when your parents get divorced, I think it hits people different ways,

but I would say it's between nine and 10 is probably the single worst age. And does this advice help your friends that you're finding a little bit, but I just can't imagine that. Like when the next guy comes in, like, I just can't like, cause you're already, how old were you?

12, 13? What I've learned looking back is that you just, being a step-parent is the most thankless job there is. It's got to be the worst. It's just brutal. You're dealing with all the shitty parts of having a kid, but they don't look like you and they're not half of your DNA. And he didn't have kids?

No, he didn't. Oh, my God. And then the kid, like, it's got to hate you right out of the gate. Yeah, it's tough. It's tough. But it's fine. I had a really good experience. I think a lot of people probably could not say the same.

Yeah, the competitive element of it or, like, you know, whatever. Or, like, it ends up being, like, did you ever see the movie This Boy's Life with Leoo and yeah yeah you end up like with the denaro stepdad she's hitting you with a belt i mean that's like that's your worst case scenario but yeah where the mother enables it because yeah the mother's like i'm just so happy to be married again do whatever fucking nightmare so you didn't have to live through that no oh good so all right so you went to graduate school? I did. For journalism?

I did. I wanted to. This is a really weird era, and there's only a couple movies that have captured it. Yeah. Where like reality bites and singles and kicking and screaming and trouble. But it was like before the internet in the 90s that all these kids graduated from college, and they didn't 100 know what to do like the ones i want to be more artistic and it's like i think i want to be a stand-up comic where do i go to la and right i think i want to act all right i'll go to la i hope i meet somebody and

with writing especially like if you're trying to write about sports yeah you're really your only path was to go to a newspaper and the thing with newspapers is people are newspapers for 25, 30, 35 years and you go in and it's not a meritocracy and I spent probably three years after graduate school after graduate school working for the Boston

Herald. So you did two years in graduate school one year of graduate school. Masters in journalism in one year? Did you double up or was that just a program? It was like an accelerated program Oh and then so then you go do what you think you need to do. Get a job at a Masters in journalism in one year? Did you double up or was that just a program? It was like an accelerated program. Oh, and then, so then you go do what you think you need to do. Get a job at a newspaper. This is great.

I'll have a column in two years. Right. And then the world doesn't work that way. And then you're like, what the fuck? And I just had just a series of bad breaks. What was it like going in with the old guys? Did you have heroes there at the time? Not at that newspaper. The Globe had a couple that I probably would have liked more but um but you didn't like it was just rough it was like it was like an aaron sorkin show yeah it really was it was like

just fucking crazy yeah and uh and at some point i just realized that it i just was gonna go crazy if i stayed because it just would have taken so long and kind of gave up. And you just got into other jobs? I was like, I'm gonna freelance. And then you don't get a freelance thing for three months and then it's like, I'm gonna work. How are you gonna make a living?

I sold bartend at this restaurant that's opening up. Where was that, Boston? I was a waiter and bartender. This is in Charlestown. Charlestown. Yeah. And then did that and all of a sudden a year goes by and I haven't written anything

and that's when I started my site because it was like but were you boozing were you getting sad I was no I was doing the whole thing you do when you work in a restaurant you stay up late

you get to know people from other restaurants yeah you get to know like everybody who's in town drinking after hours oh after after after hours

like you're up till 3, 3 in the morning smoking cigarettes yeah uh waking up at doing the next day no didn't ever did that must have been around i can't say i'm so innocent with that stuff because i bet it's a different era too when i was at restaurants it was everywhere it's like the crazy chef it probably was but people knew that i was still traumatized from len bias so maybe nobody didn't offer it for me but i gotta say though it was a great year yeah and uh i feel

like everybody should work in a restaurant in their 20s for a year yeah it should be almost like going to grad school was it like a a home-owned restaurant not a chain restaurant like yeah it was like a one it was this restaurant restaurant. It had this probably 16-seat bar in the front. Regulars? It was like neighborhood regulars. Yeah, yeah. But it was cool. And then at some point, you look around, you're 27,

and you're like, am I really going to give up writing? Is this it? Yeah. Tried to get it going again. And how'd you do that? Is that when AOL came in? Yeah, so they had this site called Digital City. It was all these different little cities.

So this is like the beginning of the internet. Yeah. Kinda. I had only had AOL, I had only had email for a year. Yeah. So 96, I got email and I had AOL. Yeah.

And you didn't have a choice really. Yeah, I didn't know what else to get. There's only a couple other ones, right? In retrospect, it had been on for people that had email since like 92, 91. I had no idea. I had no idea this whole world existed. I don't remember when I got it. Yeah.

So they had these Digital City Boston things and there was a guy, it was Digital City Boston. Yeah. And there was a guy called the Movie Guy. Yeah. And he wrote movie reviews and his picture was on there. And I was like, oh, I wonder if they want a sports guy. So I just started badgering them. And then they finally gave me a call in the spring of 97.

They built this little site for me. I edited it myself, did all that. And I was Boston Sports Guys. And it was like, I think it was $50 a week the first three months. And it was just, how many were you writing? I was trying to write, I think three times a week maybe.

But I had a whole plan for what I wanted to do. I wanted to do like, I knew I wanted to do a mailbag. I knew I wanted to do like a 30 best sports movies ever column. I knew I wanted to write about the,. I knew I wanted to do like 30 best sports movies ever column. I knew I wanted to write about the, I do a running diary of watching the NBA draft with my dad.

This is like timestamped. So I had some plans for the first couple of months. That were actually repeatable. Yeah. Refillable. A couple of gimmicks that I thought would work. And then some, you know, just have a little more attitude. Just kind of appeal to younger audience.

Because at the time i just felt like i felt like all the people in boston were not appealing to me right like they were they weren't writing or talking to people in their 20s who like sports and i was like there there has to there's a show or a writer somebody out there that's going to connect with these people and that was you you. It took a while. Yeah. Yeah. I mean, it was so early in the internet. Like the first year and a half,

you could only read the column on AOL. Yeah. And I'd have buddies at work who couldn't read it. So I used to copy paste the column and mail them to my buddies. Yeah. And then they would mail it. And then all of a sudden,

this little mail chain of the column was out. And it was like people, and then people kept asking to get on the list. And all of a sudden this little mail chain of the column was out and it was like people and then people kept asking to get on the list and all of a sudden i had this list of like i don't know 700 people or something and i'm sending it out and then one day somebody mailed me my own column like you should check this out my name is my fucking column um but that's what it was like in the 90s i mean it was like wild, wild west. When did it start to take form? When did you start to be able to get some metrics on it? Outside of like email. The big thing for me, it was funny.

There were two things. One was that sometimes that AOL main page would run a thing. So it would go from, I'd be writing from 5,000 people to like 2 million with one column. Like, whoa, hey, that was cool. Because they put it on the front? They put it on the front. And then the other thing was to get a keyword. So I had a keyword sports guy.

Yeah. And because I'm such an idiot, I thought the keyword was more important than just like maybe getting sportsguy.com, which would have been a much better way for everybody to get it. Because you were still in the AOL thing. Yeah, I was like, AOL, it's my little universe. Right. Oh, but by 2000, you could feel things opening up. And the biggest thing that happened in sports was Peter Gamins,

who was the biggest baseball writer at the time, he decided to make his column ESPN.com only. It was not available on a newspaper. You had to go to ESPN.com to get it. That was the first time people like my dad and my uncle Bob were saying. So I type in ESPN.com and then does it pop up? So you could see everybody going through the process of it. He was bringing them into the internet.

Yeah, and that's why I was like, the internet's going to happen now. Because of that guy. That and there was a trade. I've told this story before, but internet's going to happen now. I really. Because of that guy. That, and there was, there was a trade. I've told this story before, but the Red Sox traded for Pedro Martinez. Yeah. And like in 97, it was the first year I had my site. And the trade happened probably like in the morning, like 10 o'clock range. Yeah.

So I wrote a column about it. I got emails about it. Was working on another mailbag for it and like this whole news cycle what happened and then the globe comes in you know 18 hours later it's like pedro martinez has been traded it's like yeah we're all over here we've already been talking about it and that's when i really felt like newspapers were in trouble for the first time they were just late right you know it was late in like a really embarrassing gap kind of a way.

With that kind of stuff. Yeah, it's like that happened, what do you think? Yeah. And you react. And now the internet is with Twitter, 20 years later, it's like this happened, boom, here my take, and it just never ends. For better and worse, for better and worse.

But then ESPN hired me, and when they hired me, I knew. Out of AOL. Yeah, that was spring 2001 they had me write a couple pieces a couple uh guest pieces which each time i wrote them they really took off and i knew at that point they were gonna hire me and was that an exciting day yeah well for a couple reasons one was i was like 31 at that point and i don't think i had made more than 42 000 a year or something right and i i had a girlfriend i wanted to get engaged and um you know i was like wow this is meanwhile i signed like one of the worst contracts ever but that was

a job that meant security the number was big, but they owned my ass for three years in all these different ways. And I was just so happy to sign anything. And at that time, so could you tell how big your following was through AOL at all? You didn't really have a sense? I could tell stuff was happening in Boston. So like the Celtics that last the fourth year I had my site,

I could tell people in the bars and stuff like that. But it was referencing you. Yeah. No, just like people that, Hey, are you? And,

and, and people from different teams who work for different teams reaching out to me and things. So I, it was clear something good was happening. Right. But then at ESPN, when I joined ESPN,

it was, it was really the only sports website that mattered so that I joined this page that had some great writers like David Halberstam yeah Ralph Wiley Hunter Thompson was right in there at the time yeah and all of them were kind of from a different generation they're all great writers but they weren't ready did you read Hunter I read all that I mean when I was in college I read all of those right yeah um but so it's a good first person good first person oh my god the las vegas i like some of his features too oh i do too the short stuff's great yeah yeah so like at that time like you're writing you got hired espn you're you're in big company you're getting popular right yeah there was but the internet still wasn't in like you didn't see

it as huge yet no to me it was like i was still looking at it as like a a gateway to do something else yeah you know i always wanted to create like a tv series oh my god this maybe this will lead i like i'll create my own tv series right or maybe I'll get to write for Letterman. Right. It seemed like a step to do something else. I didn't see the potential of it. You wanted to write for Letterman? I just wanted,

I wanted, it didn't seem stable. Like in 2000, 2001, you tell people you wrote for the internet and they were always confused by it. They're like, you write for the internet? Do you get paid?

You know, and it did. They're asking those questions now. Yeah, I think they still are. Come full circle. Yeah. But I think, I don't know.

It just didn't seem like the greatest bet. Well, how did the relationship with Kimmel unfold? Because I wrote about him. He did this roast. Yeah. Did the shack roast. And he was really funny. And I did a column about the shack roast

and I wrote something nice about him in it. And then he emailed me and we started talking and we became friends did he read your column yeah he read it and but i mean like all these columns not just the one about him yeah yeah he had been reading my column for a few months and then i mentioned him in the column he's like oh i'm emailing this guy yeah and uh so we became friendly and we started talking and right around that same time it was summer 2002 all of a sudden abc was courting him to do that show yeah and he's like i'm gonna tell you something you can't tell anybody and i'm like who the hell am i gonna tell i live in boston yeah um he's like i think i might have a chance to get this late night show on abc yeah and uh and I want you to move out to LA and write for it.

And at that point, I'd been on the East Coast my whole life. And just, he flew me and my wife out. We went out. Could you marry the girl that you were engaged to? Yeah. Well, she was a little worried about LA because she was East Coast too. Where's she from? She's from New York.

Yeah. But we get there and there's this big there's this uh big feast he's throwing this charity feast for like the italian thing yeah and we go and it's like i'd already met his executive producer and we go and we show up my wife has her little concerns about la and there's this one of those big slides yeah that they have at like carnivals yeah and going down the slide is the guy who's going to executive produce the show and three of the juggies from the man show and they're like hey and at that point i was like i'm done she said i know she saw that

and she's never gonna want to move here but we moved there and it was great i haven't left since so but you didn't stay in television. Like, I mean. No, I didn't. I was, I worked for him for 18, 18 months. And why did you, what was the two, is your decision to stop? Yeah. I, I really loved it. I love, I love being part of a show.

I loved all the people that work for it. I love like launching something. Like I thought it was, I really believed in Jimmy. Like I really genuinely felt like he was special. Yeah. And I felt like he had a chance to do a special show. Right. And I was a child of Letterman and he was too.

And I just felt like it'd be so cool to help launch a show that becomes something. He's really gotten very good. And yeah, he really has. And the first, I don't know. We had, we probably like about nine months in we did this thing with mike tyson yeah where we flew pigeons with them with jimmy's uncle frank and i was the writer assigned to the show and the guy's supposed to edit it yeah and uh and we're on this roof in

harlem and i i just felt like i would have rather written about it than done a TV segment. And from that point on, I was like, I just felt like I had unfinished business with the comm and the internet was getting bigger. And I was like, did I, I'm writing for somebody and I'm getting like two jokes on a night or one joke or a couple ideas. And meanwhile, like I could be the lead of this website and really maybe have an impact.

So wait, they'd offered you what? They were trying to get me to come back from probably about a year in with Jimmy. But we talked. I talked to him about five or six months and I was telling him how I was feeling about everything and we had a really good... I mean, he's just a really good friend of mine. We saw both sides. I didn't want to leave the show yet, but I also felt like I was missing out on this thing that I could see.

The internet. Yeah, the internet and also like having an impact on it. I think most people's reaction was, why the fuck did you leave what you had? You had like the best gig in sports. And you just got a sense or you just saw it from the momentum of how many people were paying attention? Yeah, it was more a sense of watching what

was going on the internet and feeling like people were weren't writing the stuff i would write i just assumed when i left like i just other people would fill whatever the whatever i can say just everywhere yeah but then it really felt like there was i was like i could really have an impact right i think if i come back i think I'd put more thought in the calm. It's also hard to, you know, when you go from like you're absolutely nothing, doing nothing, to all of a sudden you're building a huge fan base. It freaks you out a little bit. You start second-guessing everything,

and you're getting really criticized for the first time. It was a lot to deal with, like just what's happening. I i'm the same guy i'm living in the same apartment i was before but now people in like australia are reading my column like what the fuck is going on yeah you liked it i liked it and i didn't like it yeah i actually didn't i i there were things i liked there are things i didn't like uh-huh so what why were you like rumored to be so difficult to the ESPN? I don't know. I'm sure I was in the early years. I think I was.

I think I was. In what way? How does that manifest itself? Being immature. But was it pushback against authority or what? Yeah, it was a lot of stuff. I was very concerned they were going to fuck with my calm. And for the first six months, they did.

They really did. They took jokes out. They took segments out. They just basically watered down the calm just enough that the outside world couldn't totally notice, but I could. And it really bothered me. And it was just, I got in this mode of just leave me the fuck alone let me write this was it one guy?

it was a bunch of guys it was just the way they worked I was nobody and they're like they're not gonna change their rules for somebody but what happened was my column started to take off

in 2001 yeah and I didn't really know that but they knew it right and all of a sudden I got enough leeway and all that stuff

but I would still battle with people there's a million things I would do over again especially all that stuff. But I would still battle with people. There's a million things I would do over again, especially now that I'm in a position of being a boss. And I've been in that position all decade. And I look back, I'm like, God, I would have hated being the boss of that person from 2001. But you just don't know any better.

And then when I went back, I had a whole plan for what I was going to do in 04. I had a really good year in 04. What happened? I was just, I knew what I was doing. When did Grantland happen? Grantland wasn't for another 2011. Oh, really?

Yeah. And that was within ESPN? Yes. My contract was up at a time when I just had a lot of leverage. So at 2004, you caught on and then you were just, you know, solid and you were making good money at ESPN. I caught on, but that, but the internet caught on. Yeah. So the Red Sox who hadn't won a world series yet, they were taken off as, you know, that whole season, that whole journey of what was happening. I was writing about them the whole season and then by the time they started coming back against the yankees

um and i was writing i was at the games i was writing about it and it felt for the first time like whatever i was writing was like genuinely important and people around the country were reading it yeah it was the same thing like like how I felt about the Boston Globe people 20 years ago. And there was, I think after one game I called, the editor in chief called me because I didn't want to write again. I was so burned out. I was up to like five in the morning writing pieces.

And the editor in chief, John Papenek, he called me and he was like, you can't stop. You got to keep going. Like everybody is reading you right now. Like you got to keep it going. This is what you wanted. And he gave me like the sports movie speech i'm like yeah everybody's reading but i was so drained and tired like but it really was a rush it was like this is what i wanted my whole life is to matter like this and to have

people read my shit and so that was the that was just the beginning of the good run all the way through. Yeah, it was fun and it was, I got to do a lot of good stuff. I had a couple contracts that come up and each time I wanted to start doing, kind of start figuring out how to use ESPN for all the potential it had.

Yeah. It was the biggest sports model that existed, but they also had all these pieces to it like when I went back in 04 one of the things I was supposed to do was write a baseball movie for them which I did and it was about to get made and then the guy who ran ESPN at the time was in an owner's booth

with George Steinbrenner who was a character in this baseball movie and he was like we can't fuck with our partners and they scrapped the baseball movie that i had spent like my whole summer writing and but at the same time you get paid for it extra i got paid for it yeah um and i did this animated series that didn't work and but i was just trying stuff because i was like this company's you know is just there and it

has money and it has resources and it has reach. And it's going to try to do movies and TV and all these different things and like, this is cool. So when I re-signed with them in 06, heading into 07, part of it was like,

I want to get more involved with, you know, the entertainment side. They had this group called ESPN Original Entertainment. A couple months later, I sent them the memo for 30 for 30. Yeah.

Which, the name was in the title. The premise for the most part was there and it was basically um centered around hbo is this monopoly on sports documentaries why yeah why don't we have it we're the worldwide leader why are we giving this up why we are documentaries we're putting so many out nobody knows which ones are good which ones aren't they have to be under a brand so people know that it's a certain thing and here's a gimmick we can use i laid most of it out and skipper and walsh the people around the company both of them were like this is great why don't you develop this and my friend connor shell who was like now runs content for espn but

at the time was pretty low down on espn films i forwarded him the email and i was like check this out and he was like this is cool and he came up with the one wrinkle of instead of four people doing it how about what if all 30 what if we went outside and got all 30 filmmakers to do the 30 and then he flew to la and we had this awesome marathon meeting in my in my little guest house in the back of the first house I bought here, and we sketched out the whole series. And then we fought to make it for, I don't know, the next year and a half until it finally happened.

And you became a TV producer. Dead. I did. And at the same time, I was writing my basketball book, which was like, it was my second book. My first one did well, but I felt like they had screwed it up. Put the columns? Yeah, it was a Red Sox book.

Why did they screw it up? They didn't release enough of them. I was going to these book signings, and they had like 25 books, and there was 300 people there. I was like, this sucks. So then when I did the basketball book, I was like, I want to make this the biggest biggest basketball book the biggest nba book it was literally it was 700 pages but so i had that coming out at the same time 30 30 was coming

out and my contract was up yeah so i used that as the leverage to do this site grant which ended up being grantland that i had always thought would be cool and i also had my podcast at the time too because i had started doing a podcast in 07 which we talked about on my podcast. And they had no other podcasts that were really resonating. But they probably didn't get it, right? They knew something was happening with mine. Because mine was getting a lot of people within like a year. But wasn't one of your problems was that they just couldn't figure out how to monetize it? They couldn't figure out how to monetize it, but they knew it was something and they knew

it was a space they needed to be. So when I had that last contract, I was like like their lead columnist i had their lead podcast i had 30 for 30 and i had this basketball book that had just hit number one so they want to lose you they didn't want to lose me it was it was just it was just it was just the perfect lining up of events but like you but you're you're fourth you couldn't have foreshadowed it it was just the way things no it was you couldn't have foreshadowed it. It was just the way things. No. You didn't have some master plan. No, but I will tell you though,

when we knew that 30 for 30, when we found out when it was going to be, I really believed in it. I really thought it was going to be a thing. Yeah. And my book was coming around the round time. And at some point early in that year, I was like, wow wow this could be good for

me my contract's up like this is this is lining up nicely it's a great feeling to where you can play something yeah i was like wow i this wasn't 100 intentional but man this is like really nice how this is lining up where you have a negotiating position yeah that's undeniable but i had the year before i thought i was gonna get fired. So that part was funny too. I was really battling with them. They were messing with my calm again. And they canceled the Obama podcast. Oh, that's right.

I'm still not 100% over. Really? Yeah, that was tough. Because I had a chance to get them before I even became president. And what was their excuse? I had a chance to get him before he even became president. And what was their excuse? Their excuse was it was at a point in the election where they had to,

they didn't want to affect it one way or the other with an ESPN thing. And if I had him, then I'd have to have. Well, they probably didn't want to affect their fans. Who the hell knows? I mean, that doesn't make sense. We want to sit this one out because we'll probably, you know. But, I mean, I could see they just didn't want to politicize one out because we'll probably you know but i mean i could see they just didn't want to politicize the platform yes right i'm saying what their garbage answer was i'm not saying what actually the reason was actually they didn't want to get political

and they were probably worried this guy was going to win and people were going to point to his pin it's like one of the reasons he won was he did this podcast and he's been yeah and you don't know like they don't know their audience in that way but you can make assumptions i was so mad we did we so then all of a sudden they they did something with both politicians later that year and they didn't even give me a heads up that i could have a chance to do the obama thing and rick riley did something with he did he filled out a bracket or did something with one of the candidates and i was so mad i had a friday column due that week it was a pics column and i handed every week and i wrote this whole column about john mccain helping me with my pics where it just skewered john mccain and i knew

they wouldn't run it yeah but i handed it in to fulfill my contractual agreement for that week yeah but knowing that it had no chance. But it was made up, right? It was all made up. And it was like, John McCain, he smells like bologna. Like, it was just, I just, I really went after him. It was a fuck you. And I knew they wouldn't run it.

So it was not going great. And then Skipper, who was running content at the time, not ESPN, we met at some, we met at this, they just built LA Live, the ESPN building. We met at this creepy conference room on the fifth floor. Yeah. I really felt like, not only did I feel like I was getting fired,

I felt like I was going to get assassinated. Like it was like one of those things that nobody around, I was like, am I going to get killed? And we just kind of hashed it out. And he was, you know, for a long time, the best boss I ever had. And we just, I was like, here's what's going on. He's like, oh, I didn't even know that.

Isn't that weird that when you have those chance meetings with the people that are really in charge, you realize just how insulated they are by underlings? Yeah, because they're delegating everything. And it's something that I'm really wary of. To save your own ass. Yeah, it's something I'm really wary of. I want to always know what's going on with people underneath me,

even if it's like the lowest level people but sometimes you just don't and you don't know and things can go a little out of control and you come in too late to it right so so yeah so another lesson yeah there's another lesson so within a year i went from thinking i was going to get assassinated to getting this giant contract extension. They were going to hire a gun to take you out. I didn't know. I was like, why isn't anybody here? Am I going to get killed? And then you renegotiated and you got Grantland.

Got Grantland, which was not named Grantland yet. And I didn't know what the name was, but I knew what I thought might work. And you were the editor? Yeah, I found all the people. And it was at a time in the internet when um everything was immediate fast fast fast and what year was that this is you're going 2010 to that end of 2009 and 2010 and it was a lot of uh you gotta react you gotta you gotta get stuff up gotta get fast gotta get traffic got a lot

and meanwhile i was writing these columns on espPN that were like 6,000 words and they were the most read columns. So I was like, this can't be true because people are still reading my columns. Right. So I thought there was a chance to create a site that had all kinds of things kind of playing a little off what I was doing with my columns with sports and pop culture, but also some good long form writing, some wackier stuff.

And really the biggest thing for me was I felt like there was a lot of good writers out there that people just weren't seeing. There was a talent thing that I think I could see. Because there was no curation. No curation. Right. And I think I could see it because i'm a writer i think it's

like how with comics you probably you can you always when somebody you feel like they're in your corner that probably means they're good yeah and i would look around and be like why isn't that person have a job yet right well wow that's weird they're using that person wrong i would use them this way and i just started kind of trusting my instincts with that and writers i liked and people i liked and if i put them under one umbrella what would that look like and you know people were not happy when we launched great land it was really wasn't why because it wasn't sports centric enough people were like fuck you why do you get to do this it really was that was the attitude that first year from who just the internet the internet that hates everything they were were like, fuck you

Bill Simmons for doing this. Yeah, why is a writer getting, why are they building a site around a writer? Huh. Why are they doing this? Yeah. It's a vanity project. Uh-huh. And, you know, we were trying to create this site that just did good stuff, that didn't take shots at other people. Yeah.

That tried all kinds of different things and would also have a podcast component and eventually some other stuff. So it was a big ambitious internet thing. Yeah, but it was within ESPN. Right. And that was another thing that made people suspicious. Right.

And then I got Closterman and we used a couple big writers for freelance pieces which made people think oh they're just they're like the Yankees they're spending crazy amounts of money we were not spending crazy amounts of money on writers at all the thing we were doing was finding young people that really had not caught the wave of their

career yet but we were going to help them get there and we weren't spending a lot of money and there was this perception that we weren't which was oh this was so frustrating. I just had to keep my mouth shut. And it was successful, right? Yeah, it was. I think by about two-

Some guy wrote for Grantland that really just unloaded on me on one piece, but it was very well written. It bothered me though. Oh, really? Yeah, I can't remember his name. We wrote a flattering thing at the ringer about you i remember yeah no this is way back it was about it was about your podcast or

something yeah i remember that so by by the time we launched grantland our staff loved you and i that's when i was like i might have to take marin out like they just have him murdered i mean i've been here to bring him to the assassination room at espn yeah i was like no fuck this guy i had the best podcast. Sure. But yeah, so it took probably a year and a half. But the big thing was we found so much talent and talent's going to win eventually. We had so many good people. And then it's almost like putting together a football team.

And it's the same thing right now at The Ringer where you try to survive the first year. And the second year you figure out who you are. And then you start adding a couple more pieces and all of a sudden it's like yeah you get a cornerback and oh now i got a right tackle and all of a sudden your team's good yeah but it's really cool it's the coolest thing i've ever been involved with well what what happened with espn and grantland how did that all come come unglued i mean that's like an hour-long answer but answer. But it was a successful site,

but it was still at a time where, you know, it wasn't completely clear how to make money from a site. Right. It was funny. They never mentioned money to me ever from like a budget, like these costs are riding too high and all that stuff. We were really responsible with what we spent stuff on. We were this boutique site that did not belong

in this giant infrastructure that ESPN had for a variety of reasons. The biggest one was their sales force, which is super successful and should be this way, is used to selling things in bulk. Yeah. And they're used to being like- To big companies. Yeah.

We got $50 million from Kia. Yeah. We got $38 million from Miller Lite. They're not used to chasing money and they certainly weren't going to sell like the mid-rolls in my podcast or anything like that. But at the same time,

would not have allowed me to use mid-roll who both of us use, which would have just made us money. And the last year I was there, my fourth year, I had one of the biggest podcasts. And I think we were making $750,000 total for the whole podcast network, for everything. We had, I think, nine of the 10 biggest podcasts at ESPN.

So when things started going south, they're like, well, your budget's high. And I couldn't get a head count the last 18 months I was there. We couldn't grow, which makes it really hard to just keep doing great stuff. And they were still adhering to the old paradigm. Yeah, they were like, look,

here's what your site brings in. And I'm like, yeah, but my site should be bringing in twice as much as this. We're doing well and we matter. And the skipper skipper had told me all along, like try to create Rolling Stone in the seventies for the internet. And that's what we were trying to do. And we were in year four.

We didn't have a web designer. We had, I think two copy editors. I had a video audio staff of four people. And meanwhile, we're cranking out podcasts left and right and videos. It was not sustainable. And that's what I was trying to tell them.

We had 50 people at the peak of Grantland, and I have 90 people at The Ringer in two plus years. It just wasn't sustainable. And so we were fighting about that. But then I had other issues because I was on the NBA show, and I didn't want to come back for the second year at all. And they talked me into coming back, and it turned out to be a disaster. What show was that?

It was the show called NBA Countdown. It's on ESPN? Yeah, it comes on before and after basketball games. But I hit a point in 2000. So you were there with the other three guys? Yeah, one of them was my buddy, Jalen. But yeah, it's just, they do it in the most missionary position, stale way possible.

Right. And you just kind of wait and take turns to speak. And I really thought I was gonna be a more creative show. It was like my worst nightmare to be on a show like that. It was just like, great point, Jalen. And here's the other thing about Charlotte. Right. And it's just like, just shoot me in the head. But when I was there in 2013 and 14,

I literally had five jobs. And I was burning out big time. Like losing your mind? A little bit, yeah. I look back now, I'm like, what were you doing? Like, I don't even remember stuff. That's what happens when you're that overwhelmed all the time. I literally don't remember stuff.

Somebody emailed me this interview I did with George Girvin, the Iceman, who's like the 32nd best player ever. And I talked to him for 40 minutes. I have no recollection of it. I don't even remember what year. I was like, how am I in this? It was like I had a drug problem and it. I don't even remember what year. I was like, how am I in this? It was like seeing, it was like I had a drug problem and it was all iced out.

Yeah, if you don't have, if you don't make any space for it to relax, you can't overload. I was running Grantland. We were doing second volume of 30 for 30. Yeah. I was doing my column, which obviously I have to research and figure out.

And you won a Peabody, right? Yeah, we won a Peabody for 30 for 30. That's a big deal. I'm doing my podcast. I never got a Peabody. Yeah, figure out what I'm doing. And you want a Peabody, right? Yeah, we want a Peabody for third. That's a big deal. I'm doing my podcast. I never got a Peabody. Yeah, go ahead. I'm doing my podcast, and then I was on this NBA show like 50 times a year. And it was just too much.

So you're about to pop. Wasn't great. Wasn't great. And then how did it all end? I spent a lot of time thinking about it, and I realized after the fact I was really traumatized by the whole thing because they reached a point where I really loved working for that place, and I really wanted it to be better. I spent a lot of time thinking about it. And I realized after the fact I was really traumatized by the whole thing. Because, like, there reached a point where I really loved working for that place.

And I really wanted it to be better. And I put, I guarantee I worked harder than anybody who was there at trying to do stuff. Yeah. And it was just so weird to be resented by that in some circles. The strangest thing that happened was Magic left the, right before i started doing the second season magic left the show he left countdown yeah he owned the dodgers he didn't have time to do it wilbon had left the show which was its own messy thing and magic left and i was like heartbroken because he was one of the reasons i came back like he's spent a year with magic johnson was amazing he's an amazing guy.

I was just trying to wrap my head around it and then the next day somebody leaked, somebody from ESPN leaked a story to a sports blog that Magic left because it had been becoming my show and there was a power struggle between me and him. Yeah. I love Magic. I was like, when that happened when people when people are leaking stuff that you work with to try to damage you that's when it goes to a whole

other level and and i just couldn't wrap my head around it because i i was thinking all i'm doing is killing myself for this company like when i finally left i had so much vacation time accrued from the last few years that I got this giant check in like December 2015. I was like, what the fuck is this? And it was like, you know, 20 vacation weeks or something for the last few years. It was crazy. Nice.

But when I got suspended, it definitely turned, which was its own issue. When was that? That was September 2014. I went after Roger Goodell on a podcast. Yeah. And it's funny because this was another example. I was doing so many different things.

Did you know it was going to happen? Did you know you were going to cause shit? No, I knew it was going to happen did you know you were going to cause shit no i knew it was going to cause i knew it was going to be called put them in a pissy situation i didn't think it was going to blow up yeah and it was one of those things where i did a podcast and then jaylen and i immediately spent six hours in the electrical closet filming all these basketball videos and we were just phones turned off the whole thing and the pod went up and it started to become a thing and by the time i got out it was like all hell had broken loose and but it was one of those things where when you're working too many hours and doing too many things you get sloppy yeah and i should have listened to that podcast i never listened to it we yeah they i two of the

people that work for me were like should you listen to this hey you sure you want to listen to something now it's fine. I trust you guys. And I never listened to it. And if I had heard it, there's like two things I would have taken out that might've made it a little more. I wanted to keep everything I said,

but I think I could have- Finesse it better? I could have finessed it. Yeah. And I didn't. And that night, the guys were in his pens like screaming at me. He was in a lather screaming at me. Yeah.

He was in a lathered up state. Yeah. I hope because of what I said on the podcast. But, yeah, it was really strange. And then everything turned. And then, like, so, like, you leave ESPN and then HBO was just there, right there, ready to go. Yeah. Well, so what happened was after I got suspended, people kind of were reading the tea leaves and I knew I wanted to go and I was trying to figure out what to do. And I wasn't sure what I wanted to do.

And I was also really burned out and I was really mad about how things, I just didn't understand why things had to go from like doing so much good stuff from oh nine to 2013 to all of a sudden it had become adversarial I just couldn't believe like things that flipped like that but did you know fundamentally that what you had created with Grant land was a a successful model and that the only thing that was really stopping you was the infrastructure of ESPN. Yeah, and it wasn't even a stopping thing. We were fine.

Yeah. But I think if you want to grow and if you're ambitious, you know, ESPN, one of the issues with ESPN is it's really hard to think on your feet with like jobs

and how to fill stuff. Yeah. Everything is a process. Yeah. And if you need a designer, it's like three months. Like if I need a designer at the ringer, I just hire a designer. I have a designer next week. Well, yeah, but that's sort of like the difference between like the internet and newspapers.

Right. I felt like the four people that I took from Grantland to try to figure out what the ringer was were people that I just worked really well with. And I thought had a good sense of kind of the same sense of talent. But I knew that I was going to be much busier this time around. I needed to have an inner circle that I just didn't have to worry about. That was the biggest thing I learned at Grantland. It's like your inner circle has to be there. So with the HBO thing, it was like I knew I wanted to do like a podcast-type interview show, and I knew I wanted to do sports documentaries and stuff

because I love doing that stuff. And then we had to rush the show. And the spirit behind what I wanted to do with the show, I actually – it's funny, it was a little similar to the Kimmel thing 15 years ago. Yeah. Where I felt like the opportunity was like, all this stuff's working on podcasts.

Why can't this work on a TV show? Yeah. Which was what? In the reality, just interviews. I felt like I had had, at that point, nine years of interviewing people, and I felt like I was had, at that point, nine years of interviewing people and I felt like I was getting pretty good at it. Right.

And I felt like this is an inefficiency on television, these awesome interviews. Why does everybody just point to Charlie Rose? There should be all types of interviews. Yeah. And the reality is now I look back, I'm like, I was already in the good spot. You and I, we have podcasts where we can interview people.

The interviews that you and I can do in this format are just going to be better than any TV interview. I mean, I had my own issues with the TV stuff. What do you mean? Well, it's just like, I knew this going in. I'm like, I'm not Jon Stewart. I'm not a performer. I'm not a stand-up.

The interviews have to carry this. This has to be a really smart show sure and it drifted toward a show that I'm still not sure what happened

the show I wanted to do what happened to the inner circle in that case maybe not a good one but but

the show I wanted to do I just and it's 100% my fault because if you don't have a have the right vision for something, or if you think you know what your vision is, and then it drifts into another place,

you can either stop it or kind of hope it works. How did it drift, though? Unfortunately, fundamentally, with a visual medium that requires people to engage their eyes and their ears. I know. You know, the continuity. Like, you know, because like with what we do here, you can almost do this passively.

Yeah, I know. In terms of take it in. So like, you know, when you got to do a song and dance, you know, in a medium that requires song and dance, and you're not a song and dance man. I found this out the hard way. I think there was ways to do it. i think it could have been once a month yeah i think it could have been loaded with interviews right and maybe it moves pivots three times and has stuff but i wasn't thinking that

way and neither were neither were they i i really felt at the time that interviews the way we're doing them on a podcast could work on TV and you quickly find out. Well now there's like Netflix as a platform is doing long form interviews with the legends, with Letterman. You know what's interesting though that? So they ran that first one, I love Letterman and Obama. I didn't watch it.

I think I would have listened to it if it was a podcast though. Which goes back to my point of like I just fucked up. haven't watched it i mean i don't what's fun about watching two people talk but when you're in the car or when you're working out or like i'm sure a million whoever's listening to this right now i'm sure they're in their car i'm sure they're at their desk or at the gym or walking their dog they're walking all this stuff painting something and when you're actually in front of a television, you know, it's got you,

especially now in the second screen era. Right, and with someone like Letterman, you just want to see him be quick. Right. I'm not looking to him for in-depth interviews. Really, though, I don't have any regrets. And my whole thing is you just got to trash it. Yeah. And it can't work every time.

It really can't. But that show went away, but you're still in business with them in a big way. I am. We have a couple cool things coming that we haven't announced yet that I'm excited about. So The Ringer just, that became the focus. Like you still are partners with HBO and you've created a podcast network. You're putting up three new podcasts a day. We're putting up like new podcasts a day.

We're putting up like six. We have like 24 shows now. Yeah. The Ringers, once the show got canceled, threw myself more in The Ringer and kind of waited to see what was going to happen with HBO because I think they were also getting the AT&T merger, all that stuff. And I think from a production standpoint, there was a wait and see thing there for a little while.

But now it seems like I think they're going to be a little more active. So as you've evolved with the internet, starting with AOL and then moving into ESPN, then finding your way to Grantland and actually creating a platform, basically. So now you're at the ringer. creating a platform for basically so now you're at the ringer now what where whereas grantland wasn't making money this is some sort of partnership where you have a lot of stake in it you're making money yeah right you're not just getting seed money from a big company no i didn't get we didn't do investors like that we it was really important to me especially after my last experience to spend the first couple years making decisions based on what was good and and just betting on talent that we liked again and taking chances and trying to figure

out what a website is in 2016 17 and 18 when things are so fast when when we were innovating the site in 2015 and the start of 2016 facebook was like the big traffic driver right we didn't trust it we just felt like what happens if they change the algorithm everyone's screwed we have to have a site that has people come to the main page we have to have a podcast network we have to be the ability to promote everything and over the last nine months it really fell into place. And it's, it's, you know,

it was much harder than Grantland. Cause Grantland, we still had the checkbook. Sure. Especially for the first year where I could be like, I like that writer. Let's get them. And,

and the infrastructure was doing stuff for us. Right. Yeah. We're talking first four months. I have my podcast. We're doing in my guest house. Yeah. And Andy and Chris, Andy Greenwald, Chris Ryan, they do this podcast called the watch pop culture podcast. four months i have my podcast we're doing in my guest house yeah and andy and chris andy greenwald

and chris ryan they do this podcast called the watch pop culture podcast they're coming over to my guest house and doing it yeah and people are just walking through my house and it's like my kids like a burglar could have walked in and taken one of my kids yeah yeah i have people they wouldn't even flinch and be like oh you must be with the podcast like yeah that's where i am as they throw them in a van. And it was just grassroots trying to figure out everything on the fly. How do we have healthcare? How do we do benefits?

Where's our office going to be? Really building a business from, you know, with a big business. It was the hardest thing. I can't even tell you how hard it is and how scary it is when you don't really know how to do a lot of it. But don't you hire people that know how to do it?

Well, that's the thing. We had a good inner circle. And I had the Grantland people that were running the site that are just great. And you got them now back. Yeah. And so I knew I trusted them. I knew at least we're going to find writers and we're going to build a culture. The biggest thing we wanted this time was

the culture has to be like lights out. You just have to have great people. Like we have great people, like really good character people that look out for each other and you can kind of feel it. That stuff, once people, the relationships build, that stuff spills in the site

and now like digital video and stuff like that, all this goofy stuff we're trying. And 2018 is like the best time this goofy stuff we're trying. And 2018 is like the best time ever to be a content producer. It's not just all the TV streaming and all that stuff, but it's all these different digital platforms and all these different ways you can reach people right away. And it's whoever has the best idea,

I think has a much better chance than maybe they did 10 years ago. The Andre doc is very good too. Thank you. How much of a part of the process in terms of editing and stuff were you there for all of that? Were you giving creative input? I mean yeah I think if you

do it correctly the director is all in as we discussed. But they also need a friend and a soundy board and somebody who can gently talk them out of stuff. Was he a wrestling fan? Yeah. Yeah, he was.

But they get lost in it and they hit a really dangerous point and they need at least one person who they trust completely. Pull them out? Well, who says to them like, I know you love that France footage, but if we just take that one part out, like, just try it.

It might not work. And they need a friend. They hit a point where they just need a friend. Comics, I feel like. They've been out on the water too long. They really do. They don't see it clearly anymore. And I identify with it because when I did my basketball book, it was so big and it hit a point where I was the only person who could see how it all fit together.

And I really needed somebody else. And it just was too hard. And it was just me. And I ended up with a 700-page book. And it should have been 500. Do people love the book, though? It seems like they do. It actually does seem like.

Because there's a million things I change already. I know. But it's one of those things where if you put that much of your heart into it that like it's got to have a pretty hardcore following my thought was the normal move would be to do two books for 350 pages each and get paid twice i'm like fuck that i'm doing one awesome book and now i'm like i should have done two books could have spread it out it would have been nice and how much do you feel in your in your uh heart and soul that that there any, you know, now that you're doing these documentaries,

or this is your first documentary for HBO Sports, is there a good healthy amount of fuck you to ESPN in this? No. What's weird about ESPN is everybody, I think pretty much, I don't want to say everybody because there's a couple people left, but most of the people that I had issues with or I feel like just ran my course with, shall we say, are gone. Oh, yeah.

And the people that are running the company now I really like, and some of them are my good friends. The guy I created 30 for 30 with runs content. Oh, yeah. That's how it works. People move up. Yeah, people move up yeah people move guys go out i i actually am buying your spin stock these days because i i think it's the most rational

higher level group they've had in a while it's a really complicated time but they're a little more equipped to i think the leadership they had before they just were people that just didn't get where shit was going like they didn't see like something like grantland we were a digital studio for them inside their company that was trying all the shit yeah and they looked at us like like it was ah this fucking thing and it was like this thing is like the future of where the internet's going yeah you should be like hey what else could you guys come up with and they just didn't see it well that's funny because it's not unlike that thing that running you had with the main guy who's insulated, is that a lot of people at those sized companies,

if they're working, they just want to keep shit the same. Yeah. And a lot of times it has to crumble in a very dramatic way for shit to change. Yeah, and I think the ESPN thing's complicated, what's happened to it. And that's why I think it's actually in really good shape now. They missed some stuff, but the biggest thing was they really underestimated the cord cutting thing. And they planned out their business for this decade,

at the beginning of this decade, thinking that they had this amount of money coming in from cable and from satellite. And when it started going backwards, I was there and I know this for a fact, they didn't know what was happening. And I have this great email that somebody sent, like the research thing, and they were trying to figure out,

I think it was 2013 or 14, why the subs had dropped. The subs are what they call like the cable and the whatever. And it was like, it was all these different reasons reasons and one of the reasons was world cup fatigue it was after the world cup it was like we we think that maybe people are it was because it was why ratings had dropped right it was like we think one of the reasons is world cup fatigue tired and then like much later in the email it's like another possibility is something called cord cutting it was like watching those internet commercials on youtube from the 1970s about watch out for child molestation

yeah um this is like this thing called cord cutting might end up being a problem and i was like yeah i think so yeah it's gonna be a major problem yeah but they're they're rallying though by in five years they'll be in ott disney will have a whole ott service that every family is going to buy because every disney movie is going to be on there and every comic book movie and well it's going to have its own platform you mean like yeah they're forming this whole and espn will be under that and what people don't understand until you have kids is the ipad and streaming services become like your virtual babysitter yeah you gotta have like as soon as your kid's old enough to be able to maneuver an ipad it's like you're

out of jail it's like i'm gonna go in the other room i'm gonna go in that room yeah and they don't care now they're like they're just like pressing buttons but as soon as that happens yeah you know we well we hope that it all ends up okay for those kids. We'll see. I'll tell you though, going back to those Parkland kids, it was the first time I was like, this generation, this might be a generation that really makes a difference and is just thoughtful about stuff and mature enough in a different way.

This is what Chuck and I talked about when we did a pod two weeks ago. The guys coming into the NBA now are these like polished guys and they're good interviews and they handle their business well and you're like how the fuck you're 19 how are you like an adult yeah and it just seems like that's starting to be what happens with this specific generation yeah they don't have they're maturing fast i think maybe because of the internet yeah because they're adapting to the pace of things into the tech you know not just the tech but to you know how to behave like a machine it's good i do go out there and act like an ambitious machine be polite see you're like me i do worry and i really i'm fanatical about with my kids i'm so worried that they're not gonna have social

skills my kids have really good social skills right now, but I always like trying to get them with people and interact with people. And when you meet somebody, shake their hand and it's stuff that you're starting not to see anymore. Well, I think that's probably, that would be the liability. I wonder how that really pans out. Where they're perfectly polite

and they know how to behave, but how much experience do they really have with engaging with people? Do they have a sense of humor? Oh, yeah. You can have a sense of humor digitally, but be the worst hang in person in person. With my son, I was letting him watch South Park

when he was like eight. All those shows. He watched Atlanta with me last night. I want him to have a sense of humor. I don't care if he's 10. I want him to know what's funny and not funny now how's he getting how's he going he's fucking hilarious oh good he's so good atlanta's a good show atlanta's a really good show really good show there's beyond comedy that thing the uh it's the show that i'm i looked forward to the

most yeah it turned out me too my girlfriend turned me on to and i was sort of like late coming to but i like donald a lot you know but i just didn't watch and then i watched the first 10 like in a day yeah and now i'm like on it you know it's funny watching with my son because i'm really hoping he's gonna laugh at a couple of the subtle parts that i would hope he laughed at and he did i'm like oh man i'm doing a good job oh good doing a good job you're doing a good job with everything man thank you and thanks for coming over by the way this was I never do podcasts I'll probably never do another one how was it

why do you you were gonna tell me why weren't you gonna tell me I don't know I always felt like I had my own podcast and it was like if I do one

then 20 people are gonna want it and then I'm just doing the same podcast over and over again and I don't know I just always felt like I have a podcast

why would somebody want to hear about another podcast well it was funny because when I started at the beginning especially i think was more of the comic driven podcast right you have to do quid pro quo yeah yeah and it actually helped i think i think it helped everybody i think what podcasts i mean podcasts have been amazing in so many different ways but how they've brought life and humanity to the comic, to the comic industry. Yeah. Not just a bunch of weird nighttime monsters.

Well, it's turned, it's turned into this like 10 years of therapy sessions with comics on each other's things crossed with some really funny stuff. Yeah. And, uh, it's such a great medium and,

and it was always the case. Like, I don't know when you've grasped it, but the first time I did one i was like this makes sense this is cool so we do this interview and then people get to it yeah this is so logical yeah and it was great i like i like the idea that you could stretch out by yourself and with people that i didn't have to be funny that i didn't have to uh to you know and then i could talk to people about me yeah yeah it's how it started we

didn't talk about you that much in this one i'm over that that was the first hundred thanks for coming thank you that's it that's the show that i want to thank bill for coming i i thought that was a great conversation engaged and nice and I also I think I'll be doing one more intro in here before the end of the month and I'm going to be on the road in Europe doing my

a few parts of the world tour you can get tickets and venue information at WTFpod.com slash tour get tickets for London, Stockholm, Oslo, Amsterdam, and Dublin.

Also the guitar thing. I'll get it going. I'll get it going. Let's give me till the beginning of May to, to get the amps up and go in and get the car guitars out here. And you know, these things take time, but give me a month

all right boomer lives It's a night for the whole family. Be a part of Kids Night when the Toronto Rock take on the Colorado Mammoth at a special 5 p.m. start time on Saturday, March 9th at First Ontario Centre in Hamilton. The first 5,000 fans in attendance will get a Dan Dawson bobblehead courtesy of Backley Construction. Punch your ticket to Kids Night on Saturday, March 9th at 5pm in Rock City at torontorock.com.

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