How I Built This with Guy Raz - The Ringer: Bill Simmons

Episode Date: February 13, 2023

Wherever Bill Simmons is, he’s obsessed with helping his team win. During 14 tumultuous years as a creative force at ESPN, that meant launching a slew of influential projects that blended sports and pop culture—including the documentary series 30 for 30, the podcast The B.S. Report, and the multimedia blog Grantland. Today, it means growing his own company, The Ringer, into a major player in the media landscape, with over 50 sports and pop culture podcasts. From his earliest days as one of the most popular sports writers in America, Bill’s journey has had all the drama and conflict of a memorable game, with plenty of good and bad behaviors to learn from...including his own.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Airbnb.ca slash host. It's the single hardest thing I've ever had to do. I never really want to do it again. I think I blacked out a couple times during it. You're making decisions on every single conceivable thing and you're missing some stuff too. Like, all right, health insurance, how do we do that? Office. How do we do that? Oh, we need desks. How do we do that? Oh, we got to hire people. Oh, this person turned us down. Oh, my God, who's going to be our accountant? You're just trying to survive. You're basically like Tom Hanks and Castaway. You've built your little raft and your goal is to just get over that first wave and you get out there. And then you're like, holy shit. Now what? Welcome to How I Built This, a show about innovators,

entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz. And on the show today how a bitter falling out with ESPN led its star sports writer and broadcaster Bill Simmons to build his own $250 million media company, The Ringer. Bill Simmons did not set out to become an entrepreneur. He was certainly entrepreneurial, but for much of his career, he was perfectly happy being entrepreneurial inside a bigger company, which was the Sports Network, ESPN. And it was at ESPN where Bill would make his mark, essentially as a content machine. First as a sports writer for ESPN.com, and then later as the architect of the network's hugely

popular sports and culture blog, Grantland. Bill was one of the creators of 30 for 30, the acclaimed ESPN documentary series, and he launched ESPN's first successful podcast, The BS Report. And Bill might still be at ESPN today if it weren't for a nasty podcast. breakup that happened in 2015. Just a few months after he left the network, the incredible blog he built there, Grantland, collapsed, and no longer exists. But that same year, Bill began to build something entirely new from scratch, his own media business called The Ringer. It was modeled on all the things he felt he couldn't do at ESPN. It's a pop culture, sports, and tech website, and a network of more than 50 podcasts. In 2020,

just four years after he launched the ringer, Bill sold it to Spotify for roughly $250 million. And along the way, he had to learn how to become a business guy, not just the creative guy. Bill grew up in the 1970s and 80s in Brookline, Massachusetts, in the shadow of the Boston Garden Sports Arena. His dad was a school administrator who loved sports, and from an early age, Bill grew to love them too, as long as it was Boston sports. Yeah. Well, Boston, I think, is one of the biggest sports towns. And we had four teams.

And I cared about all of them. And I was an only child. So we just watched everything. And I watched everything. And I just kind of became my thing. And the biggest thing, I think, was my dad took me that he got one season ticket to the Celtics for the 73, 74 season. So this is actually his 50th year. Wow.

And he used to kill. carry me in, which he could, because I was like, I turned four that first season. So he... You were not an additional ticket. He would carry you in, like, hand luggage. Yeah. And, you know, the ushers and stuff, they started to know who I was. And they used to let me walk on the court before the games and I could stand under the hoop and I could rebound. And that was really like the 75, 76, 77 season. There was, I think it was 75 playoffs. Havlicek was hurt. And I used to walk over the... This is crazy now. No, nobody.

do believe this now. I really did. I used to walk over the bench, talk to the coaches. And there was this picture of me and Havlicek. He was on crutches with, I think, the assistant coached. I'm kind of looking up at him. And they put it on the, I think it was the front of the sports section in the Harold. And it was like, you know, little kid asked Havichick was ready to play. And so that was like amazing. It's crazy. It's totally crazy. Stuff like that. The first game I really remember was I went to the famous game six of the 76 finals with my dad. It was they were playing Phoenix. Oh,

that was a triple overtime. Yeah. Yeah. It became the most famous modern NBA game. Right. It probably still is. Yeah. But that game started at 9 o'clock and I was six years old, you know, and I fell asleep

around the third quarter. It was like 11 o'clock. It was like almost the latest had been up. So actually, I was sleeping across like two people because we knew everyone in our section. And then sometime in the overtime when everybody had to stand on every play, like, I just kind of, they had to wake me up. And I kind of like came out of this haze and saw the second and third overtimes. But we got home at like 1.30 in the morning. And I remember Charlie's Angels was on. There was like a reruner Charlie's Angels at one in the morning.

And I was just like, is this what happens late at night? Like, yeah. After that game, I was like, I'm all in for the rest of my life on anything with this team. So, I mean, it's amazing because you You can't imagine today. I mean, they wouldn't even let somebody come in with a baby without a ticket today, I don't think. Maybe under two, I guess. But, like, I mean, they're massive billion dollars in the 70s. Like, the NBA was like, probably wasn't even as big a deal as like MLS is today. You know, that was one of the things I loved about the league was it was still so, I don't want to say underground, but it just like, it was like kind of the stepchild of the sports scene.

You know, all the other sports felt bigger. It's the same way, like, if I decided right now. that I wanted to write a book about, I don't know, major indoor lacrosse, they would let me in, right? Right. They'd be like, great. Come on. This sounds good. Come in, you have complete access.

And that's kind of where the NBA was. Yeah. But, you know, you go to the late 70s, early 80s, the league had a lot of issues. And there were guys that just would get big contracts and stop trying. And the league was heavily black in the 70s, which was a real issue for the networks for whatever reason. It's kind of crazy to look back now. but it was like, you know, and Halberstam wrote about this and breaks of the game. The league had this real issue of how do you sell a black sport to weigh fans, which now seems crazy.

But in the 70s, that was the narrative. And then Bird and Magic showed up. And that changed it, yeah. That flipped it. You were clearly super close with your dad from an early age. And I know your parents split up when you were in like eighth grade. No, I was younger than that. I was fifth grade when that happened.

So, yeah, it was the end of the 70s. And then you and your mom eventually moved to, you're an only child, you moved to Stanford. Connecticut. Tell me about, wow, I mean, your dad's your sports buddy. And you moved away from Boston. Yeah. So I moved to Connecticut. And that was a culture shock for 19 different reasons.

But, you know, I used to go back. I used to take the train to see my dad every the weekend. I spent summers with my dad and stuff like that. So I would still come back. I'd come back for playoffs and things like that. But it wasn't totally the same. Yeah. You mentioned this book by David Halberstein

The Breaks of the Game. And I know that book played a seminal role in your kind of teenage years. You've written about this book a lot and referenced it in your books and writing and your columns. You consider it to be one of the greatest, if not the greatest sports book

ever written, The Breaks of the Game. How much of that book do you think kind of began to influence you, even as a teenager, and thinking, like, I want to be a sports writer. I want to write about sports teams for a paper. I think though, I read it every year to just kind of remember why I like writing and reading.

Even though he had a totally different style than I did, it really helped me as a writer because with however stand it was the curiosity, right? He really wanted to figure out what's going on with this league? Is this league going to make it? The coolest thing about it was he would dive into these different characters. And I felt like, you know, after you read that book enough times, they just feel like people that became like your friends in a weird way. Yeah.

So when you moved to Connecticut, is this also like when the wheels started turning in their head, like that you could do this, that you could become a writer? Yeah. When I moved to Stanford, I went to Greenwich Country Day in eighth and ninth grade, which was like one of the best schools in New England and was a completely different animal than I went to public schools in Brookline, you know, and I was smart, but it wasn't like this school was. This school was really competitive. And at the end of eighth grade, in the English, we had to write this essay as part of the final exam that they called the Pearl. And it had to be tied

in some sort of personal thing with the book we read. And it was scored up to 40. And the teacher who had been there, who became, you know, one of the most important people for me, he'd never given a 39 out of 40. 38 was always the highest thing. So I wrote this piece. And it was actually about my grandmother. And he gave a 39. And he told the class, like, this is the first 39 I've ever given. And I'm going to read it to you right now. And he finished.

And then it was like silent because it was good. Everybody was silent for like three seconds after. And I was like, wow, this could be my thing. But it wasn't until college that I was really like, wait, could I actually just do this? Yeah. I know that when you went to college in Western Mass, College of Holy Cross, You did sports writing, you were to the school paper, but you majored in Middle East politics. Where did that come from?

Yeah, I was a poly-side major. Look, I can't defend this, and I don't even understand why I thought this way, but I was like, maybe I'll go to law school. So I was like, all right, I'm going to do that. And when I got to college, I wanted to have a sports column, and I went to see, and by the way, I was really lucky in this respect. They had a spot for me, and I wrote them a sample column, and they were like, we're going to run it this week. Yeah. Like, great. And then the next week it was like, I have this other idea for a column.

They were like, all right, let's run it. And so every issue of the newspaper in the four years I was there, I had a column. And you were writing about what? It was mostly real sports, like professional sports, and then sometimes college sports. So like, I started going after our basketball coach, George Blaney. He was this guy who had kind of peaked in the late 70s, and he would screw up games. And I started, I wrote a couple of columns critical about him and it got huge waves on campus. And I was like, our, this is interesting.

Because this is me and my friends all talking about like we think this guy sucks. And he probably didn't suck. You know, we're college kids. We don't know any better. You were writing this about the sports coach in the paper. The basketball coach, yeah. And he probably was not happy about that. Oh, he's furious.

And then I got that column to the. point that it was a conversation piece on on Friday. Yeah. And by the end of my freshman year, I was like, this is, I'm good at this. Like, this is something's going on here. And it became a huge part of my college career. And did you, I mean, if you go back and read your columns and you're probably really grateful they're not online, I'm assuming they're not online, because I'm sure there's

stuff in there that you're embarrassed by or you look at the copy now and it would be crap, but you have to write crap for a long time. in order to write good stuff. Yeah, it takes, I mean, it's like a decades-long process to feel good about what you're writing about. I think the thing back then was I was funny. And that I was weaving pop culture and even back then. And that was the stuff people had mentioned me over the weekends.

Like I would make a joke about some Brady Bunch episode. Yeah. And then I'd go to get, I don't know, coffee or food or whatever. And I would notice a lot of people reading my column just when I was walking around. I was like, ah, this is cool. Yeah. So after you graduated from Holy Cross, I guess you went on to be you to Boston University to get a journalism degree. Yeah. And when you were done, you wanted to be a sports writer, like a professional sports writer. Yeah. You're really naive at that point because you just, I was like, I had this great column in my college newspapers, so then I'll graduate and I'll go to grad school and then the Boston Globe will give you a column and it'll be great. I'll have a column by the time I'm 25. And then two years later, you're at a newspaper. or organizing, you know, the pizza run for that night and taking high school scores. And you're like, what happened?

Where's my column? So you get a job at the Boston Herald basically, you know, covering high school sports? Covering high school sports and doing like all the grunt intern work. Yeah. And I ended up doing that for three years. And the third year I started writing for the Boston Phoenix, too, and got to write some really good columns and features for them. Why did you, before you get there, I know that you really hated your time.

time at the Boston Herald. This is like the sort of early the mid-90s. And I can imagine what it was like probably people smoking in the office still. And it was like just angry. There was no smoke in the office. They would all go outside. Outside, okay. But I was more fascinated by that because it would take three minutes to get outside,

eight minutes to have your cigarettes. It was like these 15-minute breaks every 45 minutes. And I'm just looking around going, these people don't care. What is happening? I probably didn't handle it great either because I really did feel like I was better than anybody there except for maybe one or two people. And, you know, I was just of the mentality like talent should win. But I think of how I would have, the me now would have seen that person. Just like, oh, God.

Cocky, cocky, obnoxious. I was like, fuck this guy. Who does this guy think he is? But I really felt like I was good. And there was no path. And I just, I remember I spent two weeks. I pointed out this whole Sunday thing for the Sunday paper, this whole page that I wanted them to give me.

And it was like it had like a 600 word calm. It had these lists. It looked a lot like kind of what the internet would look like 10, 12 years later. Yeah. It was modeled like EW. Entertainment Weekly had that little EW, the hot list. Yeah. So there was like that version of that.

It had a little mailbag thing, which I stole from Letterman. It was all these different things that I liked. Just a bunch of things like on a printed page. It would basically be like a static web page. printed. Yeah, and I still have it. Oh, they published it? They ran it? No, no, they didn't publish it. Oh, but you mocked it up for them. I mocked it up and I actually laid it out like a newspaper page. Like on Cork Express or whatever. Yeah, and I was like, just give me this one page and I'll kill it for you guys. And they just didn't want to do it. So you start to wonder, like, is this meant to be? And I just was looking around going, man, I will still be doing this three years from now. I'll be in the exact same spot because none of these.

these people are going to leave. Yeah. By the time I started my own thing in 97, and I was able to get on Digital City, Boston, and write my column for that, I felt like it happened like probably three years too late for me. Like I really wish it had been like 24-year-old me instead of 27-year-old me, but better late than never, I guess. You quit the Herald after three years to basically freelance and then start writing this column for basically an AOL-affiliated website, right?

Yeah, but that hadn't even, I didn't even, I didn't even, know that was happening. I thought I could freelance. I was like maybe I can write scripts. Do you quit with no plan? Yeah. And I was like, and I'm going to work in a restaurant, bartend. But you wanted a column. That's really what you wanted. You wanted to be able to kind of resurrect what you were doing in college. Yeah, because I felt like the way that the columns and the way that sports media was back in the time was very like, it was way more adversarial. It was way less fun. And some of the writers that I had grown up with. They really seemed like fans first. And I was like, why don't people do that anymore? So it was basically like I kept thinking who is writing a sports com

from me and my friends. And then when I had the Digital City column, which I felt like was like my last chance and I threw myself into it. And by the way, this was a time we should mention when almost nobody read the internet. Like 97, very few people are reading, I mean, AOL subscribers maybe, but it wasn't like, oh, there's this guy Bill Simmons. There he is, right in this column. Like, nobody knew who you were. No, I had, it was AOL only, the first 18 months, Digital City. So none of my friends could read it at work. Nobody could read it on the World Wide Web. You had to have an AOL subscription. And you were only writing about Boston sports? It was a combo of Boston sports, but also like big stuff. I was doing mailbags. I remember

the third column I ever did was a running diary of the NBA draft. Like the sixth column I ever did. was the worst 30 sports movies of all time. Right. And my friends couldn't read it at work. So I would mail them the columns, and then they would mail it to a couple people. Email it. Email it to them. I'm sorry, email it, yeah.

And within about 18, maybe 12, 15 months, I don't know, there started to be this email chain and I would get these emails from people I didn't know, can you add me to the list? So I had this email list that I would send out. Like 100 people. Yeah, it might have been more than that. It might have been like 200. Yeah. It was getting some attention locally, especially.

because I used to make fun of the media members all the time. Let me ask you about that. I mean, you know, you've talked about this, that, like, you would meet these reporters, right, who were covering these legendary teams and you'd be like, oh, my God, they don't understand. They have the best job in the world and they're miserable. And, like, how is it possible that these sports writers, like, hate their jobs? They're, like, they're living the dream. Was that your perspective?

Yeah, it wasn't all of them. It was a couple of them. I remember there was somebody that covered the Celtics. and I would go and sit in my dad's seats because we were mid-court at that point. And the reporters were still sitting at the press table at mid-court. So you're right there. You're just picking up everything. You're feeling a ball on the parquet floor.

Yeah. And I remember watching them and they weren't even watching the game. They were either like sending emails or working on whatever their piece was. I didn't even know what they were doing. And I was just like, if I had that job, I wouldn't do anything other than watch everything that was happening for two plus hours and then put that in my column. Like, how do you not do that? So it was little stuff like that, but there was also like the sports radio scene at that time

was just reprehensible. It was just so negative and so they just thrived on the negativity. So being able to turn the tables on that and have fun with that, make fun of that, became part of it. One of the things I'm curious about it is, right? I mean, Boston always thought of itself as like this kind of underdog town. And frankly, that just got all quashed in the 2000s because Boston started dominate all sports. Yes.

Right. But in the 90s, like, everybody kind of sucked. And so you can understand why there was a lot of negativity on the radio and stuff. But you were, I mean, Boston's also like a brawler town. And you were going after some of these sports writers. Did they ever, you must have gotten threatened or like people wanted to hit you or punch you? I mean, did that ever happen or were you ever, like, confronted? No, I knew that people didn't like me.

I also, I think I probably went too far with some of this stuff. Yeah. You know, I look back. I'm like, I was way too hard on whatever. But at the time, you know, you're in your 20s. I was mad at and I didn't have a column. And I really resented a lot of the people that I felt like had spots that I didn't. And so I feel like if I could go back, yeah, there's some stuff I'd probably take back.

I was literally on my own, right? So I had no... No editor. Yeah, I had nobody. It was just me. Just posting it up. You'd write it and post it and that was it. There was no filter.

Yeah. I'm wondering when you were writing this column, right, your goal was to still get a print column. It was like you were thinking of like this web column as the path to getting in the Boston Globe or somewhere else, right? Not necessarily by the end. I think the big watershed moment for me was the Red Sox traded for Pedro Martinez. I can't remember what year it was. But I remember I wrote a piece about it and put it up.

And the trade happened probably like 9 o'clock in the morning. And the newspapers didn't have it until the next day. And that was kind of my vala moment for the internet. Everybody who's on the early days of the internet probably had a voila'a moment. For me, that was it where I was like, holy shit. Like the internet's going to win. Yeah. I had my column up 18 hours before the Boston Globe column.

That advantage is just too substantial. And so I really, I was all in on the internet after that. And, you know, the internet was weird back then. You would tell people would ask what I did. And I was like, I wrote this column, Digital City, Boston. People are like, what's that? Yeah. It's this website on AOL.

And they had this look kind of like, is that real? Do you get paid to do that? And, you know, I've talked about this before, but the most important thing that happened with the internet and sports writing was when Peter Gammon's got hired by ESPN. He had the most important baseball column. Yeah. He was the baseball god of writers.

And it was the single most important baseball column for 25 years. Yeah. When it went to ESPN.com. ESPN.com. Yeah. People like my dad who were kind of resistant to the internet, that was the moment where people were like, I got to figure out this internet thing.

I want to read gamins. And once that happened, that was the Neil Armstrong moment. for sports writing. Yeah. It gave the internet credibility and the internet just didn't have it before. Yeah. And ESP and I think with the game it's higher and then they started page two and they kind of realized like we have this opportunity and they don't get enough credit for that.

They were the ones that saw the opportunity. Sports Illustrated was the dominant sports magazine. Right. And Sports Illustrated missed it. Like they completely effed up the internet. A little like how Rolling Stone missed with MTV in the 80s. Yeah. Sports Illustrated missed.

with sports in the late 90s, early 2000s. They should have owned all of this. They had all the best writers, and this should have been theirs, and they just missed it. And now it's just a brand owned by some private equity firm. Right. But that's the thing. If you miss your moment, man, sometimes it doesn't come back. ESPN grabbed it.

And they started page two, and they didn't ask me to be in it. And honestly, that was a blow to me because I was like, I can't believe, like, even they're not trying to ask. So maybe I'm in the wrong spot, but then ultimately it kind of came around. And they gave you a shot to sort of guess column, like I guess around 2001, just to write a couple of columns, right? No, it was one. They asked me to write one column. And this was the, is Roger the Antichrist, about Roger Clemens? That was the second one.

Okay. The first one was after Nomar got hurt. And I wrote a Red Sox column. And that crushed for them. So they asked me to do another one. So I wrote about Clements. And at that time, ironically, the Boston Herald was trying to get. get me to come back and do this like internet calm that some of it would appear in the newspaper.

And I went to ESPN and I said, hey, I've loved writing for you guys, but I don't know if I'm going to be able to keep doing this because I think I'm going to do this Boston Herald thing. And the way my career had gone to that point, they were going to say, all right, well, good luck. But this was the one time when they were like, wait, wait, hold on a second. and they brought me to Bristol and then they offered me the chance to write for them and work for them and it all amazingly worked out

thanks to John Walsh and some other people who was the editor of ESPN at the time yeah and you know that that was it I think everybody has you know if you're successful in whatever you're going to have those three to four moments that you need somebody to believe in you in the right time

or somebody to see some sort of thing you did at the right time and that was one of my moments When we come back in just a moment, how Bill branches out into podcasting, film, and even comedy writing, and why, after 14 years, he walks out of ESPN on bad terms. Stay with us. I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2001, and Bill has a new job at ESPN, and finally his own column. And now he's more than just the bottom.

Austin sports guy. He's now writing about national sports for a section of ESPN's website called page two. It basically becomes their version of like a higher end sports commentary place. Yep. And they went out and they got Halberstam, they got Ralph Wiley, they got Hunter S. Thompson. Wow. God, I forgot about that. Oh, my God. But when I got there, my goal was like, I want to lead page two and I have a piece. You know, you had that one spot where it was like best piece of the day leads the spot. And it was such a rush to be on that page the same day when like Halberstam wrote something or Hunter S. Thompson.

And the column started to do well pretty much immediately. Like I could tell because I had my email address at the bottom and just the amount of emails I was getting. But I still really didn't have a sense for how big it was because they weren't telling me anything. And I didn't really fully understand probably until September, October when I started asking like, hey, can I can do this? They were like, great. We'll send you right now. I was like, oh, I have a little juice now. Yeah.

What was it about? Because I know you mentioned like this experience you had as a younger columnist when you went on like a sports show and you were sitting across from like the Boston Globe sports writer. And like during a commercial break, you're like, hey, what's your favorite? I don't have a favorite. I forgot about that. Yeah. That surprised you that like reporters covered sports were almost like people who covered politics who were like I don't vote. right and you saw that and you just you couldn't understand it i couldn't understand it but that's the way

it was back then i understand pieces of it like i understand yeah you have to stay attached and you have to be objective right but i never understood why somebody would be covering sports if they didn't love sports and if you love sports you have to have a favorite something you can't just be an atheist a sports atheist basically you have to have a player you love or a team or whatever and i remember like 2000 and 2001, I must have been to 55 Red Sox games, something like that, because I was like, I just want to be there. I feel like just watching us on TV, it's not good enough. Yeah. My whole thing is like, do the work.

Yeah, I felt like I could outwork a lot of the people I was competing against, especially like I was watching Rick Riley at the time, Sports Illustrated, and he was an excellent writer, and he was just writing one column a week. And you could kind of tell he was phasing out of sports. And you could see that with a lot of people as they got old. or I even now like I watch football every Sunday I watch it for 10 hours I could cheat and pretend I watch the games and do shortcuts and I don't people are going to notice on my podcast I still watch basketball all the time and you you watch hours and hours of it every yeah I wake up in the

morning and I watch fourth quarters of games that I didn't see because I just feel like the moment you stop doing that you should just quit yeah but what's interesting to me is that like the way the game has played is you've got to get access. And these sports teams, these franchises, they really, they'll punish reporters who they don't like. And then that reporter's punished. They're not getting the same access that the competing reporter is getting. And so it becomes a game. It's all stage man. It's just like a White House press conference. It's actually worse, much worse than that, because they really do control access in a crazy way. Yeah. But one of the things that, I mean, you were doing in your column and have done is like, you go after.

players. You go after owners. You go after coaches. And that meant that you, I guess, just accepted that you would not get access. Yeah. But what's weird is that changed and I started getting access. I thought like when I got to ESPN, I remember talking to John Walsh about this a couple of times. And he's like, totally be critical, but be fair. Don't be mean. And don't say anything that you wouldn't feel if you ran into the person, basically. And I look back, the stuff in the first five years. I just think sports column writing was different. It was way more performative.

It was a lot like political science, actually, where you argue a case. Like what's an argument you would have made? All right, here's one that I actually made. It's probably in my archives. You can't win a title with Peyton Manning. Brady is Bill Russell and Peyton Manning's Will Chamberlain. He's going to put up these records, but he can't actually win.

So it really started out as like a conversation you just have with friends on the sofa. Like Peyton Manning can't, he's never going to win a championship. Tom Brady, he is going, like... Yeah, or a coach X is terrible. Right. But the other thing is, you know, I'm always trying to stand out. And I just want people to come back to read me. And the only way they're going to keep coming back is if I'm unpredictable.

It can't just be like, here are my top 20 trades. It's like, what's the extra hook? What's the extra gimmicks? So I would... I use pop culture for some of it. I used to do like NFL preview of the season. Instead of just doing my preview, I would do quotes for, dazed and confused, and I would hand out the quotes to different things that I think would happen.

And it was all about like that next layer of how can I get you to come back because you don't know what I'm doing next? You went to, you moved to L.A. in 2002 to go work as a writer for Jimmy Kimmel's show. He was a fan of your column. I guess he was trying to get you to move out there. And I was wondering how ESPN let you do that. But of course, they're both Disney companies. So I guess it was okay. They were like, yeah, sure, keep writing. Because they were your employer. They were paying you. but they sort of allowed you to go and work for Kimmel as well. Yeah, I felt like I was starting to worry about my column. I always felt like my column was a gateway to do something else. Never felt like it was sustainable in a real way. Something else like what, like writing movies.

Like writing scripts, working for a TV show. And I also felt like it wasn't sustainable the way I was doing it. I felt like a wrestler that is doing these crazy bumps every night. And it's like now I'm jumping from 20 feet. instead of 15. And I was writing 10, 11,000 words a week. And it was unsustainable. Like, I really started to burn out.

And Jimmy came along. I'd been in the East Coast my whole life. And I think my wife and I were just like, we were like, fuck it. Let's go. Let's do this. So I talked to ESPN. John Skipper was running the content side at that point. He wasn't running all his pin yet.

And he handled it so well and was so cool about it that I was loyal to him after that, like with anything. And so he let me do it and we moved to L.A. in November. Moved to the Lions Den, the home of the hated Lakers, the L.A. of Beat L.A. Yeah, I went to a Laker game

I think like two weeks after I moved here and it was eye-opening. And it was Kobe Shack. It was the staples just humming on all cylinders. There were celebrities all over the place. Jack Nicholson.

Yep. And I was like, this is kind of cool. I kind of get it. Like this is so different than Boston, but I kind of get it. Better food. Yeah, definitely better food, no question. How was it working for Kim? How'd you like that?

I mean, I loved him. Yeah. And I learned a lot. And working on a TV show, it was the only time other than working in a restaurant where you felt like you're really part of something. You know, writing is, I'd been on my own for five years at that point, just writing my own stuff, relying on myself, being by myself. And it was so great to be.

with other people and really funny people. Like the funniest people, other than maybe like two friends I had that I'd ever met. And all we were doing was just giving each other shit and making jokes and trying to figure out how to help Jimmy create this show from scratch. It was just the coolest experience. And I think for me, the issue was when I moved out to L.A., I didn't realize that my column was kind of making the impact that it did, really, until I moved to L.A. all these different people were talking about it and people were trying to be, you know, by ageing, all these different things.

Yeah. You didn't know. You had no idea, like, what the reach was, really. I knew a little, but the recurring refrain from everybody was, why would you give up that column? You were the number of guy at ESPN. Like, that's, that was one piece. And then the other thing was, was I really missed the column. And I really miss writing. It was the first time. I just felt like I was doing a shitty job writing it. The Jimmy job was all in every day. And I felt like the writing was going to slip away. So that was when it started to plant in my head, like, wait, did I make a mistake? And I worked for the show for, I think, a year and a half. And there were nights where I'd get, like, one joke on. Yeah. You know, and you're just like, man, what did I do today? And ESPN.com was growing.

And I had a chance to come back and be like the guy on the website, you know? And I just felt like I'd refueled my batteries a little. And I was just like, I got to give them. this one more chance. I know you, you decided to stay in L.A. Yeah. And you're back writing for ESPN. And I know you put out a book at that time.

But I want to, I want to sort of get a sense of, I mean, you're like life style, right? Like, which involves a lot, like watching a lot of sports. Like that never really changed. Yeah, the 04, I was kind of back to where I was three years before in Boston. But way better at knowing how I have. had to do stuff. And it was a really fun year. Like, I really felt like I went up a level as a writer.

And I was watching the Red Sox were on all the time. And then the Red Sox turned out to be the famous team. Yeah. And it was great. It was probably one of the two or three best moments of my career, like being able to write all the time during that journey and go into the ALCS games in Boston, games four and five and being able to write about that that night, which I still was like probably my favorite piece I ever wrote.

Did you go to the World Series that year? 2004? I went to the two home games, yeah. Wow. It was amazing. Yeah, I had, I remember, I was pretty burned out because I was writing a lot and the games were late. There was one day where I just didn't feel like I had another piece of me and this guy, John Papineck, who was the ESPN.com editor at the time, we were talking about it and I was like, I think I'm going to skip today. Like, I just, I got nothing left. Like, I need a day off. And he's like, he can't take a day off. Like, everybody is reading these pieces every day. This is the biggest story in the world.

You're all over the place, not only America, but other countries. And he was like, isn't this what you always dreamed of? And the way he put it, it was like, honestly, one of the best speeches

anyone ever given me. And I was like, he's right. What am I complaining about? This is everything I ever wanted. So I wrote the piece that night. I want to jump ahead to 2007, because I think that's an important moment.

And I remember at that time I'd just come back from being overseas for almost seven years. And there are these things called podcast, which is when you had to plug your iPod into your computer and it would download to your iPod. And I mean, it was interesting, but it seemed really niche, right? Because in 2007, podcasting was like, it was pre-Stone Age, right? Yeah. And I think this is roughly the point where you started expanding your role at ESPN, beyond. just writing into things like podcasts and documentary series. But why?

Why did you want to do that? Yeah. So I was really aware of this has a shelf life. People get tired of writers' voices. I'm going to run out of things to say at some point. I got to start adding stuff. Like, what's next? What are the next iterations for me?

And I'd been messing around with scripts and things like that. But I had, my contract was coming up at the beginning of 07. and Yahoo was trying to get me to jump over, which I didn't want to do because I was really loyal to Skipper. Skipper was the guy who was running ESPN. Skipper is running content. He wasn't running all ESPN yet. We went to the Rose Bowl and then we talked outside his hotel.

And he had offered me a figure that was more money than I ever thought I'd make in my life. And yet I still felt like I was worth 25% more. And I was like, look, I think I'm worth more and here's why. And here's what I want to do going forward. forward. Like, I want to start adding stuff. Like, I really, like, I feel like I can have a bigger impact on the company than just with the column. And he was like, I'm it. So within the first couple months, I sent them the long memo about 30 for 30. And that was in the spring right around the same time of the podcast. And 30 for 30 was, obviously people know them as documentaries, but you had this idea to do 30 documentaries to commemorate the 30th anniversary of ESPN, 30 sports documentaries. Yeah, and it even went, it went a little deeper than that. We had our anniversary coming up in 2009. I had the title, 30 for 30.

And I was like, look, HBO owns a documentary space right now for sports. We're letting this happen. Yeah. And so that was part of the framework. Let's steal HBO's corner. So we started developing that. Like a month after, I saw I was on the website and they had this, it was like an NBA podcast. It was on the website.

You clicked on it. It was on the website. So I pressed play and something weird happened. And all of a sudden they were playing the show and it was, I think it was Chad Ford talking to Danny Edge and Danny Age talking about Boston and the draft. So listen to the whole thing. And I was like, I don't understand what that was. So that was, was that a show? Was that like an interview in a locker room?

But like I kind of loved it. How do I get one of those? So I emailed the ESPN. I was like, whatever that podcast thing is, can I have one? And they were like, really? And I'm like, yeah. So they were like, all right, we'll send you some equipment. And then I started to think about, all right, what would I want to listen to?

You know, I didn't know how to interview anybody. And what I wanted to listen to was not awkward interviews with people. I wanted to listen to, like, chemistry. So I'll have my buddy Jacko come on to talk about the Yankees versus the Red Sox. I'll have my buddy Jacoby come on to talk about the real world and the new season that's happening. It was a combo of that or like information stuff with people like Rick Buecker and Mark Stein. And even though nobody was, nobody was listening. I mean, you were doing it for an audience of a tiny number of people.

I disagree. I don't. It was on the website. So I do think people were listening to it. Oh, it was on the way. Okay, it was on the way. So people were streaming it. They weren't listening to it.

It wasn't buried. Yeah, they were streaming to it. Okay, I got you. Whenever the Apple infrastructure kicked into place with the charts, I remember I was always like one of the top three podcasts. But there really weren't a lot of podcasts. It was like me and Mark Marin and a couple others. But the thing I wasn't prepared for was all of a sudden, celebrities wanted to come on.

And that started like 09. Like I remember Seth Myers and I were emailing about the Steelers or something. He's like, I thought Jacko was so funny talking about blank. I'm like, you listen to the podcast? I was just like stunned that people listen to it. He's like, yeah, come on anytime you want. I'm like, you will. So I could feel like momentum with it.

Yeah. I had so many things going on that I was like just thrilled about because I still had my calm, but I had 30 for 30. We were in the throes of that. And then I had the podcast. Then I had this basketball book that I was like, this is like my one chance to write this book. Yeah. So I was like, I just felt like this is my moment.

I'm grabbing it. But in the midst of all this, tension begins to really build between you and certain managers or editors. Like in 2008, you got in a dispute. 2008, yeah. You stopped writing the column for a while. What were they about? Was it mostly about like what you wanted to write, what they didn't want you to write? What were the arguments about at that time?

The catalyst, and I'm not saying I was 100% great in all of this, and there's some things that I think I could have been more mature about. But the first real catalyst was when they canceled the Obama podcast. What was that? Tell me that story. Yeah, I don't know that story. Yeah, so spring of 2008, Obama was, clearly headed to probably getting the Democratic nomination.

And Obama's going to come on my podcast. And to me, it was like, this would be the greatest thing that ever happened in my podcast. Yeah. I also thought it had a chance to be the first important podcast ever, because nobody of any real substance had ever done a podcast. So I was like, this would be like a transformative moment for me, for podcasts, the whole thing. And ESPN squashed it. And they squashed it for reasons that.

Why? I didn't fully understand. ESPN was very worried about bias or... Seeming like they were biased one way or the other with Democrats, Republicans, whatever it was. And they were just like, well, you'd have to have equal time with the Republican thing.

And I'm like, but that's not going to happen. Like, I have a chance to talk to Obama. And also, he's a sports fanatic. Yeah. So I took that one really hard. And then there were some other stuff behind the scenes that I was getting frustrated by. Yeah.

They'd hired Rick Riley. And it was after. they had signed me and he made way more money than me and I just couldn't believe it because I was more important to them than he was. It became a respecting to me. And it all led to like, I told them like, I'm taking eight weeks off and I'm going to work on my book. But I was like ready to quit by the end of 2008 and we had this come to Jesus moment in the new L.A. Live building they were meeting with me and Skipper and Walsh. Within five minutes, we figured everything out. And my issue was that I just never had a real conversation with it about it. I was

getting quietly frustrated thinking they knew what was going on. And they didn't. And they didn't. And that was a good lesson to me as a boss eventually down the road was like, you can't assume that the people that work for you know everything. That's in your head. And you can't assume that the people of the higher ups know everything that's going on. And the best way is just to communicate with them. And a lot of people don't realize that. So anyway, it all, we ironed all that out. In 2009 was like one of the best years I ever had for them. That year, your book comes out, tops New York Times bestseller list.

And 30, 30 came out three weeks before the book. Right. But you also still, I mean, you were working for them. So ultimately, like, you were accountable to them. Like, they could hold you accountable and punish you. Like, they, you sent out some tweets that were critical of a sports station in Boston. They didn't like that. So they suspended you from Twitter.

And they could do that. Yeah. I guess my issue was maybe I didn't fully realize sometimes the impact. You know, my profile went way up in 2009. So whatever you would write would get scrutinized more. Yeah. Yeah. And also because you are an employee or were an employee of ESPN, from their perspective,

whoever has that ESPN.com email address or who's writing under their umbrella represents them. Yeah. And by the way, they're right. Yeah. They should feel that way. Like, I'm working for those guys. They're paying me a salary and better. and all this stuff, and I'm representing their company. And that was something, I feel like from

09 on, there's like a six, five-year stretch there where I really felt like I loved working for that place. Yeah. You know, I hate the Yankees, but they were like the Yankees. They were the best. And I wanted to be at the best place read by the most people. One of the things that a lot of people really knew you best for was Grantland, right? This is a multimedia website that you basically put together. in 2011, and it was part of ESPN, and it was amazing. I mean, you had Chuck Klosterman and Wesley Morris and Colson Whitehead. Just incredible writers writing for Grantland on sports and pop culture, and it became a hugely important, like, cultural touchstone for ESPN.

Yeah. Anyway, in 2011, I guess you wanted to start it, right? So you, what did you do? Do you met with John Skipper who ran content at ESPN? Yeah. Skipper and I went out for drinks and I just was like, I have this idea, I want to do this website. And you were close with him. He was super close with John Skipper. I was.

And I was like I want to do this sports culture website. I feel like from a writing standpoint, everybody's doing blogs, everybody's writing shorter stuff. And I feel like there's a zag that could be had here. I think there's a lot of good writers out there. Yeah. One of the things with me was I always kind of knew who the other good writers are, the people that weren't getting enough of a chance because I'm competitive. So you look at people like, oh shit, that person's good.

Watch out for them. And so sketched out this whole sports and pop culture site because I felt like everything was like you're a sports site, you're a basketball site, you're a movie site, you're a pop culture site. And I was like, you know, honestly, people who read my column, they're just as likely to care about the Sopranos as they were, would be about the NBA draft. I was like there's got to be some sort of vortex for all this stuff. And I felt like page two at that point had really kind of missed it. Editorially and some of the hires, like they just, they didn't crack the code.

And I felt like I could. And I was really influenced by the national and inside sports specifically. Yeah. And Spy Magazine. Yeah. And late 70s Rolling Stone. I feel like that's sitting there for somebody. And I want to do it.

I want to do it with you guys. I want to create this place. That was going to be a massive investment because you're, I mean, you're essentially getting like Vanity Fair quality writers for this website. It was going to be expensive. You got to pay those writers to write that stuff. So I'm going to disagree. One of the big premises of Grantland was that we weren't going to do it that way. And I actually went back and I studied a lot of these different places. I put real thought into it. One of the mistakes that they made was, you know, they would blow really all their budget on like expensive writers who were in

their primes or even a little past their primes. Yeah. You know, if you look back at the people that succeeded for Grantland, it was all people that, for the most part, were the up-and-comers. It was Rember Brown. It was Jay Kang. It was, we had Hwasu. We had Bill Barnwell and Zach Lowe.

And we had Katie Baker. You going down the line, we just had over and over again, we're able to find really, really good, talented, young people, Jonathan Abrams, et cetera, et cetera. And this was really, I guess 30 for 30 was kind of like this, but this really was the first time you were managing people. You were running a team of people. Yeah, that was, which I was ready for in some ways because I watched Jimmy do it and I watched how we did the 30th, 30 stuff.

Yeah. I also, I really believed in what we were doing. And to me, it wasn't just a writing site. And I think as the years pass, I think people miss some of what Grantland was trying to do because, like, we had a podcast network before anyone did. Yeah. We had a deal with YouTube. We built this little studio that we were cutting all these different videos that we were doing. We were doing March Madness, pregame shows live from my house.

There was an energy to some of those stuff we were trying that I think we were trying to become a digital content epicenter for ESPN. trying to become this playground for them that they didn't have. And I feel like we did that. And Grantland broke even, but we should have made more money. We had nine of the top 10 podcasts at ESPN during a time when podcasts were starting to make real money. And they didn't know how to monetize it. They didn't know to monetize it. Yeah, they gave it away. I mean, they sold all of our podcasts advertised in the subway for $750,000 a year. Right. When we had, it was easily $6, $7, $8 million worth advertising we could have gotten from the pods at that time. So I was getting really frustrated because you have to grow. You have to,

like we didn't have a social media editor. We didn't, we were missing all these things. And I could just see the finish line. I just knew like we were headed toward a bad place. And it was getting more and more frustrating. I want to ask you about the tension continued. And I feel like, and there's not a dig at you. I'm just curious. It's not a dig. It's maybe a critique. I'll take the Dick. Okay. I feel like you were sometimes trying to stir up shit, not just about, like, players or teams, but about, like, I mean, you posted tweets that were critical of another ESPN show,

first take. Yeah, I did. Maybe they deserved it, but like, I don't know, why would you do that? At that point, I felt like I was team ESPN, and I really, really cared about. I felt like we were winning. Yeah. We were the dominant sports platform. And that show that day, I was watching.

It was first take. It was Richard Sherman. brought on to debate Skip Bayliss, who was one of the hosts. And it was just this really vicious segment. They went out of it in a nasty way. And it was content that I thought was beneath us. And should I have sent an email over a tweet? Sure.

Yes. It really came from like profound disappointment. Yeah. And should I said that out loud? No. Fair enough. All right. I mean, so you've got, I mean, the thing is like Grant Land, right?

It wasn't profitable, which I, I don't think is a problem at all because it was certainly it was culturally important and it brought people into ESPN who would otherwise may not have come into ESPN. Did ESPN, did you feel like they recognize that? But you realize like the profitable thing is insane to me. Okay. I know I know you're hung up on that. It doesn't matter. No, no, but that was a criticism we took and it's like, wait a second. We're a startup inside a company that makes billions and billions of dollars. We're bringing in an incredible amount of talent where, you're, in the forefront of all these things that they should care about going forward, like podcasts,

like streaming video. Yep. And you're worried that we break even? Right. Like, we're doing great. And we should be making more money than we did. So I was always like, what is that criticism? But did they value it internally for like the cultural impact that it started to have?

Did you feel like people at ESPN are like, hey, Bill, like, we're getting like, you know, more women coming to the side and we're getting like, you know, younger people. Like, was anyone saying that? I think Skipper felt that way. I think my big mistake tactically. was ESPN is a huge company and most of it said on the East Coast. And I think the success we were having over on the West Coast, we didn't want to deal with anybody else.

We were just doing our thing. Oh, they hated you guys for that. Yeah, we had ESP in the magazine that, you know, I left. And we had ESPN.com that could kind of control whether they sent us promotion or not. And they always considered us as an adversary. So it started to feel like we weren't on the same team. You know, I look back, I was definitely doing too many things. I think when you're doing too many things, you just feel like you're on a hamster wheel

and you're mad at everybody half the time. And for me, I was like, I was running Grant Land. I was right in my column. I was doing my podcast. I was on NBA countdown. Which is a television on TV. Yeah, it was the basketball show that's before and after the games. And I was doing 30 for 30 with Connor and John Dahl.

And it was like that, I look back and that was like insane. Why was I working like that? It all kind of comes to a head in 2014. You are on the podcast, the BS report. Yeah. And went after Roger Goodell, the NFL commissioner for he had said, basically said that Ray Rice, the player for the Ravens, who's videotaped beating his wife, Goodell said that they weren't aware of it or they didn't know about this or something like that. And they did. They knew.

The Rice has told them. Yeah. No, he lied. And you went after him. And you called him a lying liar sack of lying, lying, lying, et cetera. I don't even think that's what got me in the most trouble. It was that I stupidly dared ESPN to like, and if you think I'm wrong, you know. Oh, you dared them. You said if you think I'm wrong or fire me or whatever. Yeah, it's like, yeah, come get me. But explain why ESPN would have been worried about you calling Goodell a liar. I mean, they're an independent sports network. Why would they care?

I think there was a tone I had in that that went probably too far. But, I mean, they called your bluff though, right? I mean, ESPN. suspended you in 2014. Yeah. I mean, in some ways, they kind of had to because it's like when the star athlete starts going after the owner of the team, right? The owner of the team has to decide, well, am I, you know, am I going to? It was stupid.

It was a mistake on my part, but I think that thing that really got me was that I got suspended without pay for the first two weeks. And I already felt like I was underpaid for them and I was killing it for them. And it was kind of irreparable after that. I think everybody kind of knew where it was going. But I was really loyal to everybody at Grantland and what we had created. And I didn't want it to affect Grantland. So I was publicly, I was just trying to make it seem like everything was fine.

I was still doing my job. But it was just getting unsustainable. When we come back in just a moment, how Bill branches out on his own and discovers the joys of not having a boss and all the frustrations of being one. Stay with us. I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. So it's September of 2014, and Bill is suspended from ESPN for three weeks. And even though he'll eventually go back to work there, it won't last for long.

So I get suspended. Yeah. And one really interesting thing happens that I wasn't prepared for. Everybody is reaching out with some sort of business idea or, hey, when you leave. And I'm hearing from like rich guy circles and people I didn't even know. Like come, I'll invest in you. Start something new.

Yeah. If you're going to start something new, can we talk? Or hey, I work for here. We'll take you tomorrow. So it was weird. On the one hand, it was the worst professional experience in my career. And really, really devastating to just like, I felt so bad for the Grinland people because I had like 50 people underneath me.

now all of a sudden everything's in flux and I have to figure out how to manage that and handle that. You felt bad. I mean, you didn't walk out of there like, screw these guys. You actually were quite sad during that time. Oh, yeah, really upset. When I finally went back to work, we had a meeting and we had all of our staff in there. And Dave Jacoby, who I was really close to, who ran audio and video for us, he basically had to talk for me because I couldn't talk. I was so upset. So that was the shittiest part. But then the flip side of that was just all these people that came out like, hey, if you're ready to get out of there, like here I am. But that was surprising to you.

That was the fact that people came to you, that got you thinking, well, maybe I could do this. Maybe I could leave this home, this place that I've been at for 14 years. Yeah. I mean, look, it was the amount of people and it was the types of people, like famous investors and people. And I was like, holy shit. And we talked, my agent talked to Skipper, and we were transparent about like, hey, Bill has a chance to like start his own thing. Like there's no question he could go on and do that. Is there a way for me to stay?

Maybe Grantland, he, we go 50-50 on Grantland going forward where he gets a stake in that and so on and so on. And we did talk about that a little bit. But there was so many people trying to undermine me and Skipper at that point that it just wasn't going to happen. And then they had a whole plan for Grantland. They brought in Chris Connolly to be the. editor who wasn't really involved with Grantland. I don't feel like Grantland should have been done in six months. Yeah, because it lasted six months after you left. Six months. And the culture became so bad, so quickly that people started to leave. And then you could just see the writing on the wall. But like,

the stuff that we built for them, the writers that we had, we had nine of the ten biggest podcast that they had. We had this whole YouTube digital culture. We had a huge video library for them. We were in the middle of all the places you need to be. It's totally crazy to me that they would have just let that IP evaporate like that. It's crazy. It's actually an insane business decision. It's an insane business decision. Just sell us to somebody else. But they honestly thought that they could just take it over and it would be fine. But that's what you think when you have people that aren't creative in leadership positions where they just think, oh, we'll move somebody else in it's like, that's not how this shit works. When you finally left, were you like energized? Were you like, yes, I'm going to.

going to start. Were you kind of sad? Well, the way it went down was terrible. There was this other thing that happened the day before they announced that they weren't renewing my contract where I went on Dan Patrick's show. They asked some question about Goodell. Dan Patrick did. And I made a joke about, like, I'm not sure he has, what's the phrase? The sticker fortitude, whatever.

But everybody's like hyper sensitive to any sort of me versus Goodell that they could put in the headlines. So people write the news story. Right. And Skipper saw one of the news clips, and he got mad. And then I got mad that he got bad. And they had been planning to have me on the NBA draft again because it had done really well. And I emailed them.

I was like, hey, you know, I'm pretty busy. I've decided I'm not doing the draft. And that was when they just, they leaked to the New York Times that they weren't going to renew my contract, which at that point, I knew I wasn't coming back. They knew I wasn't coming back. But we could have handled it, I think, on both sides with some dignity. and they just didn't. And it was just like, this sucks. I can't even go into the office

and say goodbye to everybody I worked with. When you left ESPN and you started to think about what you could do, you were already kind of thinking about it. You had this blueprint. You had Grantland. It was a pop culture site. It was YouTube.

It was podcasts. And podcasts were really what was generating most of the revenue. Was that in your head? You were like, I know what to do. I know how to create something like this. Yeah. So there were two separate things going on.

One is I knew I wanted to do The Ringer as a company. And I had the four people from Grantland that eventually we all decided to work together that would help me build the website. And I knew I was going to make real money for my podcast that would be able to help pay for anything. But I was trying to figure out the TV side of it. And the thought was like, could I get heavily involved with HBO sports? And could I create an interview show for them and, you know, went down that path. And I think the mistake looking back was I was so mad at how the ESPN thing ended that I just tried to do everything all at once. And it was both things suffered.

I think, you know, I definitely wouldn't, wouldn't do it that way again. Why didn't the HBO show work in your view, by the way? You did it for one season. A couple reasons. I never 100% figured out what it was because it was basically an interview show, which I wanted it to be an interview show. I had so much success with my podcast with the long form interviews that I was like, this should be a TV show. Yeah. What I didn't count on was that it's just more fun to listen to a podcast.

You can listen it on your own time. You don't have to watch it. Right. So I never cracked the code. And I was so bummed out about it. And I really felt like, how did I fuck this up? Like, it had been my first, like, big failure in a while. Yeah.

And part of it was I'm not a comedian. I think to have a show like that, you have to have some sort of comic background in some way. But really, like, the talk show is kind of, it's this era of, like, like eight, nine years where it's kind of dead from a TV standpoint, right? And my show ended up being one of, I would say, 20 shows that didn't work. Yeah. Especially sports-driven talk shows. There's really no record of them working in the last 15 years.

I was like, I'm going to change that. And it was stupid. Did that in any way, like, shake your confidence? Because, you know, you left ESPN, you were a big star there. And probably there are some people are like, ha, ha, ha, his HBO show didn't work. Oh, there was definitely, I mean, there was two things. when I left ESPN, everybody's like, you can't leave the nest. Yes, ESPN's the reason you succeeded.

You can't leave. You're going to fall apart. And then the second thing was stuff built around, you know, with like one person at the forefront, like businesses, there was not a lot of big track record at the time. So when the HBO show failed, I think a lot of people, there were some pieces. I saw a couple of them that were really nasty. Like, oh, now it's over. And I was like, this is definitely not over.

Like, I will, I knew we had some good ringer stuff. I also knew, like, I'm going to figure out some different way to make an impact. Okay, so you're building this media company called The Ringer, and it was going to be sports and pop culture and podcasts and videos and writing. Yeah. And one thing I'm curious about is you had worked for ESPN for 14 years, and they were really running the business side. Like, you weren't controlling it, right? But now you are the CEO of a company, right? And so how did you, I mean, the learning curve is steep, right?

I mean, you had run a team at ESPN, but running a business in addition to that is a different beast. Beast is a great word. It's the single hardest thing I've ever had to do. I never really want to do it again. I can't possibly describe how hard it was. I think I blacked out a couple times during it. You're making decisions on every single conceivable thing, and you're missing something. some stuff too. Like even with the ringer. Yeah. I don't even think we had HR for the first like

year and a half, which is absolutely insane to me now. But you're just trying to survive. You're basically like you're Tom Hanks and Castaway. You've built your little raft and your goal is to just get over that first wave and you get out there. And then you're like, holy shit. Now what? And you're just thinking like, all right, health insurance. How do we do that? Office. How do we do that? Oh, we need desks, how do we do that? Oh my God, who's going to be our accountant? How do we do a website? Who's going to host it for us? Do we build it ourselves? Do we spend $5 million on a website that we knew in 2015 website behavior and websites were shifting into something else? We didn't know what that was yet. People's attention spans were getting shorter. So we knew the ringer had to be different

than Grant Land. We couldn't have 7,000, 8,000 word pieces anymore. How do we do SEO with Google? And you were trying to do this initially with a team of like four people, right? Yeah, I had four people, and it was four people that I worked great with at Grantland. And that was the big thing I learned at Grantland was like the team part of it is so important. So with the ringer, we had four people that I felt really good about. Sean was our number two at Grantland. And he was ready to run Grantland by like year three. And just editorially he got it.

So that was fantasy. Chris Ryan was like a really good ideas guy for sports and culture. and worked great with all of us. Mallory was like the best young editor we had and just like indefatigable work ethic. And then Julie Lipman was young, but like a go-getter and just like a problem-solver. And really from November on, we rented this house in this kind of crappy part of Hollywood. And we just tried to figure out, what do we want to do? How are we going to be different from Grantland?

Everyone's going to pair this to Greenland. How is it going to be different? Who do we want to get? What talent do we like? How do we do podcasts? We did the first like five months from my house. It was my podcast and was the watch with Chris and the Andy. And they would just come over. They would just get into my house. They knew the code. They would go in the back. They would record. Everyone was over all the time in my house. My kids just got used to it. My dogs got used to it. And I think quickly we realized the podcast piece of it was the meal ticket just because that was financing the whole

operation. Not all of it, but a lot of it, because we, we were a couple years ahead of people on the podcast front. Yeah. And by the time the competitors came, you had a structured audience, yeah. We were too established. Yeah. So we, and we found a lot of talent. Like, even like we had the Potsave America guys, that podcast started with us in 2016. Right. And on the way through, we, we developed a lot of stars and a lot of people that we elevated. So I'm really proud of that part. And making those podcasts wasn't expensive. No, wasn't expensive. And then the big thing for me is, did we want VC money or not? Yeah.

And they were just these extra people you had to have in your life. And they had money and they had expertise, but they also had expectations. And for us, like, we met with Benchmark, who I thought was really smart. And Bill Gurley, who's a great guy, he said something to us at one point. He's like, when we invest, we expect to make like 10 times what we put in, right? and do you think the ringer can be ESPN? And all of us kind of looked at each other, and then we talked about it after,

and we're like, we're not sure we want to be ESPN. We want to be a place that finds talent and pushes talent up a level, and we want to do great sports content and great culture content. But do we want to be like Yahoo? Like, no. Ultimately, you did raise money.

Yeah, so it was HBO put in $5 million as part of, they didn't want me to do the ringer. They wanted me to do the TV show and that's it. And I was like, you don't understand. I'm doing the ringer and I have to do the ringer. And it almost stalled the deal. So their perspective was, well, if you're going to do this, we want to have like a small piece of it.

Yeah. And we evaluated it at, I don't know, some bogus number. I think it was 50 million or 100 million. And they put in 5 million and they got 10% of it. And that was it. And that was it. You didn't raise any subsequent money after that? No.

Nothing. I knew that I could pay for stuff with the podcast. And I had, you know, I had money from the HBO deal. I had made a lot of money at ESPN. And I was just like, I'm betting on myself. Yep. And then the website, we felt like we could make money on too. Maybe not as much as you would have made in 2009,

but at least enough to be a tiny bit profitable. And all of the articles initially would be written by a collection of freelancers? No, we went, by the time we launched a website, we probably had like 40 employees. Which was in June 2016. Wow. I mean, initially you launched it on Medium, right, on that platform. Yeah. So that was one of the big decisions was do we build our own website? Yeah. It was just Medium was basically the website host.

Right. So we were there for a year, but we knew we had to get off. And then Jim Bankoff, he ran Vox. And he really wanted us to do the ringer of Vox. So this was kind of a half-ass way of doing that, where we got to kind of be on Vox. They got to participate in the profit stuff. You did a deal with them. Yeah, we did a deal with them. those partnerships initially were a way for you to kind of scale up without having to make a big investment in like ad sales or well there was one other piece we had midroll this is an ad sales company mid role yeah they just go out they work with different brands and it's like hey bill's podcast has three mid rolls they go find it they take a cut of yeah of the price and that's it how did you just help me understand how you manage that because you were i mean clearly you like

the creative stuff. You like to do the shows. You like to, you know, work with writers. You like that stuff. And clearly, I think you don't like the business side of it. No, I actually disagree. I like the business side. I think the surprising thing for me with the ringer was how much I like the business stuff. And part of it was because when we got to the ringer, Michael, you know, I think you need stuff that drives you. But I was really like, I want to come back to haunt ESPN with this. I want to build this into a business that will make that motivated you it was your michael jordan like another log on the fire no question that i understand that motivation and anger is is a really powerful motivator i understand that i'm talking more about like you've got to record several hours of podcasts a week and go to meetings

and people need your attention to approve this and what do you think about this website what do you think about this design or what about this logo that's what i mean yeah how did you do that maybe i'm a psycho but i like that stuff. I think the thing I learned at Grantland is is the delegation part. And you have to trust your inner circle and believe in your inner circle completely. At Grantland, I didn't totally have the inner circle. At the ringer, we did. You know, ultimately, I think the hardest thing for me was at ESPN, I was the boss, but I wasn't. Right? ESPN was the boss. Yeah. So I was, it felt like I was way more one of the gang, even though I wasn't. At the ringer, I was the boss. I was the one that ultimately was deciding all the money stuff.

And that dynamic gets a little bit different. And it kind of makes you lean toward trusting less people. But I still feel like I think we had a lot of good relationships with our talent. But yeah, I think it's fucking hard. Yeah. You launched this thing in 2016. We launched a website in 2016. The podcast basically launched in 2015.

Yeah. Right. And 2020, right before the pandemic, it was announced that you sold to Spotify for around $200 million, give or take, 250. And I mean, it's sort of a dumb question, which is why, because it's $250 million. It's a lot of money. I mean, that's incredible. But why at that point? Did you think Spotify could really supercharge us now that if they're the owners, we could take cash out of the table?

and then we don't have to worry about like the bottom line and then they can really make us even bigger. Was that, were all those things, reasons why you did it? Yeah, it started, they had approached us, like maybe the start of 2019, something like that, or late 2018 because we were doing a couple of podcasts with them. And I didn't realize they were sizing us up to possibly buy us because I'm stupid, but they came back with us four times.

And one of the times they came, this lady named Sheila came, who I thought was just part of the Spotify creative team or whatever. God forbid I was smart enough to Google her. And it was their acquisitions lady. And all I had to do, if we had just Googled her, we would have been like, oh shit, they might be trying to buy us. We were pretty naive about that. But I didn't want to be bought.

I didn't want to be owned by anybody. I didn't want to work for anybody. I loved what we were doing. And I loved not having a boss. I didn't want to be in another big company. And then they bought Gimlet. And they bought Gimlet for like $200 million. Yeah.

And we were like, wow, Gimlet makes like $10 million a year. They just got $200 million. Like, what the hell? Like, we were way more profitable than them. So that got our wheels turning a little bit, but I still didn't want to sell. And started it, we lost out on a couple people. Lost out who went to other places. Talent stuff.

Yeah. And started to feel like we were like a mid-major in the NCAA tournament. That we could be really successful. we could go 27 and 5 and win our league, but then we would go to the tournament and we would get our asses kicked by the big boys. And I thought the business that we had the first three years was still too dependent on me.

My goal the whole time was always like, if I get hit by a bus tomorrow, would the ring or survive? It would suck to get hit by a bus, by the way. So even like when we talked to Spotify, so much of the conversations were about, what about you? Well, what if you leave? And we just felt like,

We're in the middle and we were in control of our own destiny, but ultimately what was that destiny going to be? We never hired a banker. I didn't necessarily want to sell, but I was really intrigued by Spotify. And I was like, these guys are going to be the future of audio if they already aren't now. And maybe this is a place that could supercharge us. But we never shopped around. People didn't know we were for sale. It was like Spotify or we're not doing anything.

One of the things I wonder about is learning to become a manager of people. It's hard because being a founder is really different from being a manager, right? From running the company. Founder, you're just like constantly like trying to hit the next thing and just like plowing forward. But then being a manager is you've got to like look at the landscape. You're dealing with things, right? You guys had unionization, all kinds of things that happen when you're a manager that are more challenging. than being a founder.

So how did you, how have you kind of evolved as a manager? I think the climate's a little bit different now. I think it's much harder to manage in the last four years than it probably was in the 10 years before. With like Twitter and social media and people just like, I think you see over and over again where some disgruntled employee, they leave a company and then they light it on fire basically. And then I think it has made it a little more formal than it used to be.

Yeah. I definitely talk to less people than I used to. Yeah. But at the same time, every generation has its challenges, right? And I think, to me, Twitter causes a lot of the stuff because people can just run to Twitter. Yeah. I always wonder, like, if we just didn't have Twitter, would some of the stuff be easier? But who knows?

Yeah, I wonder about that, too. And also, in big companies, it's just so much more formal and the interactions are just so different. For good reasons, too. There was a lot of bad stuff that happened. But it's also taken away some of the, I don't know, the ability for people to grow and develop and to become, you know, just to learn from people who've been there before. Yeah, you made the key point. It evolved this way for the right reasons, right? But at the same time, there's been some collateral damage with it where I think office culture is much different, especially post-pandemic with not having the same kind of office culture for the stuff that, like, at least we like to do, is pretty damaging, you know, because.

Yeah. We had podcasts that developed just from the ringer office those first couple years where like I remember hearing this guy Danny Hyfetz just arguing about sports with somebody else football. And he was like an intern at that point. But I was like, this guy's good. I wonder what he'd be like on a podcast. And you're just going to lose all of those moments. Yeah. The spitballing is what gets hurt.

You can't do it on Zoom. You can't. Bill, how long are you committed to being part of? Spotify to being part of the ringer. I think I have two years left. And I am committed because I want Spotify to win the same way I wanted ESPN to win once in a time. There's a lot of the same limitations and issues in a different way.

I think ESPN was way more political and way more sinister. Spotify's not sinister, but it's also a big company that has a lot of opposing objectives. And I think we'll see how it goes for the next two years with them. But I still feel like they're the dominant music platform. they have a huge audience. But you are, I mean, can you imagine like not like two years it's done, your contract's done? Like, I would think you still want to be on your show. You still want to be talking about sports.

Yeah, I don't know. I go back and forth on that because at one time I thought like, oh, Spotify, this would be it. And then how long am I going to work this hard, you know? And then just managed it. We have 150 people, you know, like we had 50 at Grantland. I think the thing. I'm battling with is in my head I'd always thought it was over after two years from now, but I still love what I'm doing and I still, I actually feel like I'm getting better at the podcast

still and like, why would I leave? Yeah. The question for me is always going to be, can I win where I'm at? And then also like, did we take this as far as it can go? When you think about the arc of your career, right, and you clearly worked really hard. You had a plan, you were ambitious, you wanted a column, went to the web, like all these things that you did. And then, you know, you met people or certain things happened. I don't know. How much of what happened to you, do you attribute to how hard you worked and the grind and how much do you think it had to do with luck?

I think there's a third factor that's the most important. I always try to challenge myself really starting in 2006. When 2006 started, I was like, I don't want to leave 2006 in the exact same position I was in 2005. And I think I've stuck to that really for 16 years now where every single year, I wanted to look back at the end of the year and be like, oh, this is the year this happened. Yeah. Especially with content and creativity, like if you're just running it back every year, that's not sustainable. And eventually people are going to pass you and you're going to be on the outside looking in. So I think once I realize that, that helped me the most.

I think some of it was hard work and talent. And then the luck piece, like I think to just be like, oh, you were lucky. Like, what does that mean? Like, I worked my ass off for every single thing that happened. I don't understand how luck factors into that. For the most part, like, I think when people talk about luck, it almost feels like it's kind of like a loser attitude where it's like, oh, that was lucky. It's like, I don't feel like there's a lot of luck with this stuff.

Opportunity can be luck, but you still have to like nail the opportunity and you still have to put real thought into it and you still have to give a shit. And the thing I've learned over everything is the people that give a shit are the ones that succeed. That's Bill Simmons, Boston sports guy and founder and managing director of the ringer. By the way, would you defend a strong bid to put Roger Clemens in the Hall of Fame? Or do you just think he's completely compromised? He cheated and they should never even consider it. I think all of those guys should be in the Hall of Fame.

Really? Barry Bonds, Mark McGuire, even though they cheated. Yeah, just put it on the plaque. If I'm taking somebody in a museum, I want them to learn as much about the history of a sport as they could possibly learn. And to not have Barry Bonds and Roger Clemens in there is insane. And there should just be a room where it's like, hey, then we had these guys. The room of cheaters plaques. Cheater room.

Whatever you want to call it. Yeah. Sounds great. Son, I want to show you this inspiring room here at the Hall of Fame, the Cheaters room. Yeah. son, don't do what these guys did. That's the whole point of a museum. Hey, thanks so much for listening to the show this week.

If you want to contact our team, our email address is hibt at ID.wondry.com. If you want to follow us on Twitter, our account is at How I Built This and mine is at Guy Raz. And on Instagram, we're at How I Built This and I'm at guy.org. This episode was produced by Alex Chung with music composed by Ramtin Arablewe. It was edited by Neva Grant with research help from Sam Paulson. Our production staff also includes Casey Herman, J.C. Howard, Carrie Thompson, Kira Joaquin, Elaine Coates, John Isabella, Chris Messini, and Carla Estevez. I'm Guy Raz, and you've been listening to How I Built This.