The Ringer: Bill Simmons

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.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

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• 1:32Guy Raz?

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• 2:16Guy Raz?

  on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer. For the first time ever,

• 3:00Guy Raz?

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• 3:45Guy Raz?

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• 4:27Guy Raz?

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• 5:12Speaker 01

  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 of 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 gotta hire people. Oh, this person turned us down. Oh, my God, who's gonna be our accountant? You're just trying to survive. You're basically like Tom Hanks in Cast Away. 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?

• 5:57Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:08Guy Raz?

  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.

• 6:26Guy Raz?

  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.

• 7:09Guy Raz?

  And Bill might still be at ESPN today if it weren't for a nasty 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.

• 7:52Guy Raz?

  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.

• 8:15Speaker 01

  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, it 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 seventy-three, seventy-four season. So this is actually his fiftieth year.

• 8:40Guy Raz?

  Wow.

• 8:40Speaker 01

  And he used to carry me in, which he could, because I was like, I turned four that first season, so he-

• 8:46Guy Raz?

  You were not an additional ticket. He would carry you in like hand luggage.

• 8:50Speaker 01

  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 seventy-five, seventy-six, seventy-seven season. There was, I think it was seventy-five playoffs, Havlicek was hurt. And I used to walk over the, this is crazy now, nobody believe this now, but 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 coach. 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 Herald. And it was like, you know, little kid asked Havlicek if he's ready to play. And so that was like amazing.

• 9:33Guy Raz?

  It's crazy. It's totally crazy.

• 9:35Speaker 01

  Stuff like that. The first game I really remember was that I went to the famous game six of the seventy-six finals with my dad. It was, they're playing Phoenix.

• 9:46Guy Raz?

  Oh, that was a triple overtime. Yeah.

• 9:48Speaker 01

  Yeah, it became the most famous, modern NBA game and it probably still is.

• 9:53Guy Raz?

  Yeah.

• 9:53Speaker 01

  But that game started at nine o'clock and I was six years old, you know, and I fell asleep around the third quarter. It was like eleven o'clock. It was like some, almost the latest I'd been up. So they, 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 one-thirty in the morning and- I remember Charlie's Angels was on. There was like a rerun of Charlie's Angels at one in the morning and I was just like, is this what happens late at night?

• 10:30Guy Raz?

  Yeah.

• 10:31Speaker 01

  After that game, I was like, I'm all in for the rest of my life on anything with this team.

• 10:36Guy Raz?

  So, I mean, it's amazing because 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 seventies, like, the NBA was like, probably wasn't even as big a deal as like MLS is today.

• 10:53Speaker 01

  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?

• 11:03Guy Raz?

  Totally.

• 11:03Speaker 01

  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?

• 11:13Guy Raz?

  Sure, right.

• 11:13Speaker 01

  They'd be like, great.

• 11:14Guy Raz?

  Come on.

• 11:15Speaker 01

  This sounds good. Come in, you have complete access. And that's kind of where the NBA was.

• 11:20Guy Raz?

  Yeah.

• 11:21Speaker 01

  But, you know, you go to the late seventies, early eighties, 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 seventies, 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 in Breaks of the Game.

• 11:42Guy Raz?

  Right.

• 11:42Speaker 01

  The league had this real issue of how do you sell a black sport to white fans? Which now seems crazy, but in the seventies, that was the narrative. And then Bird and Magic showed up.

• 11:51Guy Raz?

  And that changed it.

• 11:52Speaker 01

  Yeah. That flipped it.

• 11:54Guy Raz?

  You were clearly super close with your dad from an early age.

• 11:58Speaker 01

  Yeah.

• 11:58Guy Raz?

  And I know your parents split up when you were in like eighth grade.

• 12:02Speaker 01

  No, I was younger than that. I was, I was fifth grade.

• 12:05Guy Raz?

  Fifth grade.

• 12:05Speaker 01

  When that happened. So, yeah, it was the end of the seventies.

• 12:08Guy Raz?

  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 like-

• 12:17Speaker 01

  Right.

• 12:17Guy Raz?

  You moved away from Boston.

• 12:20Speaker 01

  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 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.

• 12:36Guy Raz?

  Yeah. You mentioned this book by David Halberstam, The Breaks of the Game. I know that book played a seminal role in your, you know, 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 or a paper?

• 13:05Speaker 01

  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 it's named, 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?

• 13:25Guy Raz?

  Yeah.

• 13:26Speaker 01

  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.

• 13:37Guy Raz?

  Yeah. So when you moved to Connecticut, is this also like when the wheels start turning in your head, like that you could do this, that you could become a writer?

• 13:47Speaker 01

  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 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.

• 14:31Speaker 01

  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?

• 15:00Guy Raz?

  Yeah. I know that when you went to college in Western Mass, College of Holy Cross, you did sports writing, you were a sports editor, you worked at the school paper, but you majored in Middle East politics. Where did that come from?

• 15:13Speaker 01

  Yeah, I was a poli sci 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 or...

• 15:20Guy Raz?

  Yeah.

• 15:20Speaker 01

  So I was like, alright, I'm gonna do that. And when I got to college, I wanted to have a sports column and I went to see... And by the way, this, 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 gonna run it this week.

• 15:35Guy Raz?

  Yeah.

• 15:35Speaker 01

  I'm like, great. And then the next week, it was like, I have this other idea for a column. They were like, alright, let's run it. And so every issue of the newspaper, in the four years I was there, I had a column in.

• 15:48Guy Raz?

  And you were writing about what?

• 15:49Speaker 01

  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, alright, this is interesting. Like, 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, but...

• 16:21Guy Raz?

  You were writing this about the sports coach in the paper?

• 16:24Speaker 01

  The basketball coach, yeah.

• 16:25Guy Raz?

  And he, he probably was not happy about that?

• 16:28Speaker 01

  Oh, he was furious.

• 16:31Speaker 01

  And then I got that column to the point that it was a conversation piece on, on Fridays.

• 16:37Guy Raz?

  Yeah.

• 16:38Speaker 01

  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.

• 16:47Guy Raz?

  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. Cause I'm sure there's stuff in there that you're embarrassed by. Or you'd 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.

• 17:05Speaker 01

  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 would mention me over the weekends. Like I would, I would make a joke about some Brady Bunch episode.

• 17:23Guy Raz?

  Yeah.

• 17:23Speaker 01

  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, this is cool.

• 17:33Guy Raz?

  Yeah. So after you graduated from Holy Cross, I guess you, you went on to BU, to Boston University, to get a journalism degree.

• 17:41Speaker 01

  Yeah.

• 17:41Guy Raz?

  And when you were done, you wanted to be a sports writer, like a professional sports writer?

• 17:47Speaker 01

  Yeah. You're really naive at that point. Cause you just, I was like, I had this great column in my college newspaper. 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.

• 17:59Guy Raz?

  Right.

• 18:00Speaker 01

  And then two years later, you're at a newspaper organizing, you know, the pizza run for that night and taking high school scores. And you're like, what happened? Where's my column?

• 18:10Guy Raz?

  So you get a job at the Boston Herald, basically is, you know, covering high school sports?

• 18:15Speaker 01

  Covering high school sports and doing like all the grunt intern work.

• 18:19Guy Raz?

  Yeah.

• 18:20Speaker 01

  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.

• 18:30Guy Raz?

  Why did you, before you get there, I know that you really hated your time at the Boston Herald. This is like the sort of early to mid 90s. And I can imagine what it was like, probably people smoking in the office still. And it was like, just angry.

• 18:43Speaker 01

  No, it was, there was no smoke in the office. They would all go outside.

• 18:46Guy Raz?

  Outside, okay.

• 18:47Speaker 01

  But I was more fascinated by that, cause it would take three minutes to get outside, eight minutes to have your cigarette. So 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?

• 19:02Speaker 01

  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, that me now would have seen that person.

• 19:18Guy Raz?

  Just like a cocky, cocky, obnoxious.

• 19:20Speaker 01

  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.

• 19:27Guy Raz?

  Yeah.

• 19:28Speaker 01

  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 column. It had these lists. It looked a lot like, kind of what the internet would look like 10, 12 years later.

• 19:45Guy Raz?

  Yeah.

• 19:45Speaker 01

  It was modeled like EW, Entertainment Weekly had that little EW, the hot list.

• 19:50Guy Raz?

  Yeah.

• 19:50Speaker 01

  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.

• 19:55Guy Raz?

  Just a bunch of things, like on a printed page. It would basically be like a static webpage, but printed.

• 20:00Speaker 01

  Yeah. And I still have it.

• 20:02Guy Raz?

  Oh, they published it? They ran it?

• 20:03Speaker 01

  No, no, they didn't publish it.

• 20:05Guy Raz?

  Oh, you, but you mocked it up for them.

• 20:06Speaker 01

  I mocked it up and I actually laid it out like a newspaper page.

• 20:10Guy Raz?

  Like on Quark Express or whatever.

• 20:12Speaker 01

  Yeah. And I was like, just, just give me this one page and I'll kill it for you guys. And they just didn't want to do it. So that you start to wonder, like, is this meant to be? And I just was looking around going, man, I, I will still be doing this three years from now. I'll be in the exact same spot because none of these people are going to leave.

• 20:31Guy Raz?

  Yeah.

• 20:32Speaker 01

  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.

• 20:47Guy Raz?

  You quit the Herald after three years.

• 20:50Speaker 01

  Yeah.

• 20:50Guy Raz?

  To basically freelance and then start writing this column for basically an AOL affiliated website, right?

• 20:58Speaker 01

  Yeah, but that hadn't even, I didn't even know that was happening. I thought I could. Freelance, I was like, maybe I can write scripts.

• 21:05Guy Raz?

  Do you quit with no plan?

• 21:06Speaker 01

  Yeah, and I was like, and I'm gonna work in a restaurant bartend.

• 21:10Guy Raz?

  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.

• 21:15Speaker 01

  Yeah, because I felt like the way that the columns and the way the 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 column for 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.

• 21:49Guy Raz?

  And by the way, this was a time, we should mention, when almost nobody read the internet, like 97, very few people were reading. I mean, AOL subscribers maybe, but it wasn't like, oh, there's this guy Bill Simmons, or he is writing this column. Like, nobody knew who you were.

• 22:04Speaker 01

  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.

• 22:16Guy Raz?

  And you were only writing about Boston sports?

• 22:18Speaker 01

  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.

• 22:30Guy Raz?

  Right.

• 22:31Speaker 01

  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.

• 22:38Guy Raz?

  Email it, email it to them.

• 22:39Speaker 01

  I'm sorry, email it, yeah. And within about 18 months, 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.

• 22:52Guy Raz?

  Like 100 people?

• 22:54Speaker 01

  Yeah, it might have been more than that. It might have been like 200.

• 22:56Guy Raz?

  Yeah.

• 22:56Speaker 01

  It was getting some attention locally, especially because I used to make fun of the media members all the time.

• 23:01Guy Raz?

  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?

• 23:21Speaker 01

  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 midcourt. So you're right there.

• 23:39Guy Raz?

  Yeah.

• 23:39Speaker 01

  You're just picking up everything.

• 23:41Guy Raz?

  You're feeling the ball on the parquet floor.

• 23:43Speaker 01

  Yeah, and I remember watching them and they weren't even watching the game. And they were either like sending emails or working on whatever their piece was. Or 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.

• 24:20Guy Raz?

  One of the things I'm curious about is, right? I mean, Boston always, always thought of itself as like this kind of underdog town. And frankly, that just got all quashed in the 2000s. Cause Boston started to dominate all sports.

• 24:32Speaker 01

  Yes.

• 24:32Guy Raz?

  Right? But in the 90s, like, everybody kinda 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 sportswriters. Did they ever, you must've gotten threatened or like people wanted to hit you or punch you or? I mean, did that ever happen? Or were you ever like confronted?

• 24:55Speaker 01

  No, I knew that people didn't like me. I also, I think I probably went too far with some of this stuff.

• 25:01Guy Raz?

  Yeah.

• 25:01Speaker 01

  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 twenties. I was mad 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?

• 25:24Guy Raz?

  Yeah.

• 25:24Speaker 01

  So I had no.

• 25:25Guy Raz?

  No editor.

• 25:26Speaker 01

  Yeah, I had nobody. It was just me.

• 25:28Guy Raz?

  Just posting it up. You'd write it and post it and that was it. There was no filter.

• 25:31Speaker 01

  Yeah.

• 25:32Guy Raz?

  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?

• 25:45Speaker 01

  Not necessarily by the end. I think the big watershed moment for me was. The Red Sox traded for Pedro Martinez and 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 nine o'clock in the morning and the newspapers didn't have it till the next day. And that was kind of my voila moment for the internet. Everybody who's on the early days of the internet probably had a voila moment. For me, that was it where I was like, holy shit, like. The internet's gonna win.

• 26:17Guy Raz?

  Yeah.

• 26:17Speaker 01

  I had my column up 18 hours before the Boston Globe column. That's 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 like, what's that?

• 26:37Guy Raz?

  Yeah.

• 26:38Speaker 01

  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 Gammons got hired by ESPN. He had the most important baseball column.

• 26:56Guy Raz?

  Yeah, he was the baseball god of writers.

• 26:59Speaker 01

  And it was the single most important baseball column for 25 years.

• 27:03Guy Raz?

  Yeah.

• 27:03Speaker 01

  When it went to ESPN.

• 27:05Guy Raz?

  Dot com.

• 27:06Speaker 01

  ESPN.com, yeah. People like my dad, who were kind of resistant to the internet. That was the moment where people were like, I gotta figure out this internet thing. I want to read Gammons. And once that happened, that was the Neil Armstrong moment.

• 27:21Guy Raz?

  For sports writing.

• 27:22Speaker 01

  Yeah, it gave the internet credibility and the internet just didn't have it before.

• 27:26Guy Raz?

  Yeah.

• 27:26Speaker 01

  And ESPN, I think with the Gammons hiring, 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.

• 27:39Guy Raz?

  Right.

• 27:40Speaker 01

  And Sports Illustrated missed it, like they completely effed up. The internet, a little like how Rolling Stone missed with MTV in the eighties.

• 27:49Guy Raz?

  Yeah.

• 27:49Speaker 01

  Sports Illustrated missed with sports in the late nineties, early 2000s. They should have owned all of this.

• 27:55Guy Raz?

  Yeah.

• 27:55Speaker 01

  They had all the best writers and this should have been theirs and they just missed it.

• 27:59Guy Raz?

  And now it's just a brand owned by some private equity firm.

• 28:02Speaker 01

  Right. But that's the thing, like if you miss your moment, man, sometimes it doesn't come back.

• 28:08Guy Raz?

  Yeah.

• 28:08Speaker 01

  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 then.

• 28:24Guy Raz?

  And they gave you a shot to sort of guest column, like I guess around 2001, just to write a couple of columns, right?

• 28:31Speaker 01

  No, it was one. They asked me to write one column.

• 28:33Guy Raz?

  And this was the, is Roger the Antichrist? Is it about Roger Clemens?

• 28:36Speaker 01

  That was the second one.

• 28:37Guy Raz?

  Okay.

• 28:38Speaker 01

  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 Clemens. And at that time, ironically, the Boston Herald was trying to get me to come back and do this like internet column that some of it would appear in the newspaper. And, 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 gonna 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.

• 29:23Guy Raz?

  Yeah.

• 29:23Speaker 01

  And it all amazingly worked out, thanks to John Walsh and some other people.

• 29:27Guy Raz?

  Who was the editor of ESPN at the time.

• 29:29Speaker 01

  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.

• 29:45Guy Raz?

  Yeah.

• 29:46Speaker 01

  And that was one of my moments.

• 29:49Guy Raz?

  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.

• 30:14Guy Raz?

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• 30:56Guy Raz?

  The agents bring speed and scale, and people bring taste, judgment, and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro annual plan. That's framer.com/built. Rules and restrictions may apply. AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off. That's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on.

• 31:41Guy Raz?

  NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new, expert-created business guide in your hands today. It's called Aligning for the Agentic Era: How AI is Changing Everyday Work. And right now, it's yours, absolutely free. Inside, you'll discover how AI could Reshape work across your entire organization and how to position your business to prosper from it.

• 32:26Guy Raz?

  If your revenues are at least in the seven figures, get NetSuite's free business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work, at netsuite.com/built. The guide is free to you at netsuite.com/built. Netsuite.com/built. Stripe is built for whatever comes next because the pace of change has never been faster than it is right now. New business models, new currencies, and new expectations for speed, reliability, and scale. Stripe builds financial infrastructure that helps businesses start, grow, and operate globally. From payments and billing to fraud protection and cross-border payouts, Stripe is built

• 33:11Guy Raz?

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• 33:52Guy Raz?

  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 Boston sports guy. He's now writing about national sports for a section of ESPN's website called Page 2.

• 34:11Speaker 01

  It basically becomes their version of like, a higher-end sports commentary place.

• 34:16Guy Raz?

  Yep.

• 34:16Speaker 01

  And they went out and they got Halberstam, they got Ralph Wiley, they got Hunter S. Thompson.

• 34:20Guy Raz?

  Wow. God, I forgot about that. Oh, my God.

• 34:23Speaker 01

  But when I got there, my goal was like, I want to, I want to lead Page 2, 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 do this?" They were like, "Great, we'll send you right now." And I was like, "Oh, I have a little juice now."

• 35:04Guy Raz?

  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 the commercial break, you're like, "Hey, what's your favorite sports team?" And he was like, "What? What do you mean? I don't have a favorite."

• 35:22Speaker 01

  I forgot about that, yeah.

• 35:24Guy Raz?

  And that surprised you, that like reporters who covered sports were almost like people who covered politics, who are like, "I don't vote," right? And you saw that, and you just, you couldn't understand it.

• 35:35Speaker 01

  I couldn't understand it, but that's the way it was back then. I understand pieces of it, like I understand.

• 35:39Guy Raz?

  Yeah.

• 35:40Speaker 01

  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 this on TV, it's not good enough."

• 36:10Guy Raz?

  Yeah.

• 36:11Speaker 01

  My whole thing is like, do the work. And I felt like I could outwork a lot of the people I was competing against. Especially like I was watching, um, 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 older. I, even now, like, I watch football every Sunday. I watch it for 10 hours. I could cheat and pretend I watched the games and do shortcuts, and I'd don't. People are going to notice on my podcast. I still watch basketball. All the time.

• 36:46Guy Raz?

  And you, you watch hours and hours of it every day.

• 36:48Speaker 01

  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.

• 36:56Guy Raz?

  Yeah, but what, what's interesting to me is that like, the way the game is played is you've got to get access and these sports teams, these franchises, they really, they'll punish reporters who, who they don't like. And then

• 37:08Speaker 01

  Yeah.

• 37:09Guy Raz?

  that reporter's punished, they're not getting the same access that the competing reporters getting. And so it becomes a game. It's all stage managed. It's like a White House press conference. It's actually worse, much worse than that because they really do control access in a crazy way.

• 37:24Speaker 01

  Yeah.

• 37:25Guy Raz?

  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.

• 37:40Speaker 01

  Yeah, but it, and 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.

• 37:52Guy Raz?

  Hmm.

• 37:53Speaker 01

  And don't say anything that you wouldn't feel if you ran into the person, basically.

• 37:58Guy Raz?

  Yeah.

• 37:58Speaker 01

  And I, 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.

• 38:08Guy Raz?

  Mm hmm. Like, what's an argument you would have made?

• 38:10Speaker 01

  All right, here's one that I actually made. It's probably Markov's. 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.

• 38:21Guy Raz?

  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-

• 38:30Speaker 01

  Yeah, or a Coach X is terrible.

• 38:33Guy Raz?

  Right.

• 38:33Speaker 01

  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 gimmick? So I would, I use pop culture for some of it. I, like, I used to do, like, NFL preview of the season. Instead of just doing my preview, I would do quotes from Dazed and Confused, and I would hand out the quotes to different things that I think would happen. And it was like, 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?

• 39:09Guy Raz?

  You went to, you moved to LA in 2002 to go work as a writer for Jimmy Kimmel's show. He was a fan of your column and I guess he was trying to get you to move out there.

• 39:18Speaker 01

  Yeah.

• 39:18Guy Raz?

  And I was wondering how ESPN let you do that, but of course, they're both Disney companies. So I guess it was okay. Like they were like, yeah, sure. Keep writing. Cause they were your employer. They were paying you, but they like sort of allowed you to go and work for Kimmel as well.

• 39:31Speaker 01

  Yeah, I, 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.

• 39:43Guy Raz?

  Something else, like what? Like writing movies?

• 39:45Speaker 01

  Like writing scripts, working for a TV show, like, 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.

• 39:58Guy Raz?

  Yeah.

• 39:59Speaker 01

  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, yeah, 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 ESPN 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 LA in November.

• 40:30Guy Raz?

  Moved to the lion's den, the home of the hated Lakers, the LA of beat LA.

• 40:36Speaker 01

  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 Shaq. It was the staples just humming on all cylinders. There were celebrities all over the place.

• 40:51Guy Raz?

  Jack Nicholson, yep.

• 40:52Speaker 01

  And I, 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.

• 40:59Guy Raz?

  Better food.

• 40:59Speaker 01

  Yeah, definitely better food. No question.

• 41:01Guy Raz?

  How was it working for Kimmel? How'd you like that?

• 41:03Speaker 01

  I mean, I loved him.

• 41:05Guy Raz?

  Yeah.

• 41:05Speaker 01

  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.

• 41:31Guy Raz?

  Yeah.

• 41:32Speaker 01

  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, the issue was when I moved out to LA, I didn't realize that my column was kind of making the impact that it did really until I moved to LA. And all these different people were talking about it and people were trying to be, you know, by AJ and all these different things.

• 42:00Guy Raz?

  Yeah. You didn't know, you had no idea like what the reach was really.

• 42:04Speaker 01

  I knew a little, but the recurring refrain from everybody was, why would you give up that column? You were the number one guy at ESPN, like that's, that was one piece. And then the other thing was I really missed the column and I, I really missed 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 I, 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.

• 42:39Guy Raz?

  Yeah.

• 42:39Speaker 01

  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.

• 42:49Guy Raz?

  Yeah.

• 42:49Speaker 01

  And, and I just felt like I had refilled my batteries a little and I was just like, I gotta give this one more chance.

• 42:58Guy Raz?

  I know you, you decided to stay in LA.

• 43:00Speaker 01

  Yeah.

• 43:01Guy Raz?

  And you're back writing for ESPN and, and I know you, you put out a book at that time. But I want to, I want to sort of get a sense of, I mean, your like lifestyle, right? Like which involves a lot, like watching a lot of sports, like that never really changed.

• 43:18Speaker 01

  Yeah. The oh four, I was kind of back to where I was three years before in Boston, but way better at knowing how I 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.

• 43:37Guy Raz?

  Yeah.

• 43:38Speaker 01

  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 is like, probably my favorite piece I ever wrote.

• 43:53Guy Raz?

  Did you go to the World Series that year, 2004?

• 43:56Speaker 01

  I went to the two home games. Yeah.

• 43:57Guy Raz?

  Wow. It was amazing.

• 44:00Speaker 01

  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 Papenek, who was ESPN.com editor at the time, we were talking about it. And I was like, I think I'm gonna skip today. Like, I just, I got nothing left. Like, I need a day off. And he's like, you 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 had ever given me. And I was like, he's right. What am I complaining about?

• 44:45Speaker 01

  This is everything I ever wanted. So I wrote the piece that day.

• 44:50Guy Raz?

  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 podcasts, which is, you know, 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, it was pre-stone age, right?

• 45:17Speaker 01

  Yeah.

• 45:17Guy Raz?

  And I think this is roughly the point where you started expanding your role at ESPN beyond just writing and into things like podcasts and documentary series. But why? Why did you want to do that?

• 45:30Speaker 01

  Yeah, so I was really aware of, this has a shelf life. People get tired of writers' voices. I'm gonna run out of things to say at some point. I gotta start adding stuff, like, what's, what's next? What are the next iterations for me? And I'd been messing around with scripts and things like that. But that, I had, my contract was coming up, 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.

• 45:58Guy Raz?

  Skipper was the guy who was running ESPN.

• 45:59Speaker 01

  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. 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 in. So, within the first couple of months, I sent them the long memo about 30 for 30. And that was in the, that was in the spring, right around the same time of the podcast.

• 46:40Guy Raz?

  Mm-hmm. 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.

• 46:51Speaker 01

  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 the documentary space right now for sports. We're letting this happen.

• 47:05Guy Raz?

  Yeah.

• 47:05Speaker 01

  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.

• 47:18Guy Raz?

  It was on the website. You clicked on it?

• 47:20Speaker 01

  It was on the website. So, I pressed play, and something weird happened. Then, all of a sudden, they were playing this show, and it was, I think it was Chad Ford talking to Danny Edge, and Danny Edge talking about Boston and the draft. So, I listened 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 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.

• 48:02Speaker 01

  And what I wanted to listen to was not awkward interviews with people. I wanted to listen to, like, chemistry. And 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 news season that's happening. It was a combo of that, or like, information stuff with people like Rick Buker and Mark Stein.

• 48:25Guy Raz?

  And even though nobody was, nobody was listening, I mean, you were doing it for an audience of a tiny number of people.

• 48:31Speaker 01

  I disagree. I don't. It was on the website, so I do think people were listening to it.

• 48:35Guy Raz?

  Oh, it was on the web. Okay, it was on the web. So people were streaming it. They weren't listening to it.

• 48:39Speaker 01

  Yeah, they were streaming to it.

• 48:40Guy Raz?

  Okay, I got you.

• 48:41Speaker 01

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

• 49:18Guy Raz?

  Yeah.

• 49:18Speaker 01

  I had so many things going on that I was like just thrilled about because I still had my column, but I had thirty for thirty. We were in the throes of that. And then I had the podcast and I had this basketball book that I was like, this is like my one chance to write this book.

• 49:33Guy Raz?

  Yeah.

• 49:34Speaker 01

  So I was like, I just felt like this is my moment. I'm grabbing it.

• 49:37Guy Raz?

  But in the midst of all this, tension begins to really build between you and certain managers or editors. Like in two thousand eight, you got in a dispute. 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?

• 49:59Speaker 01

  The catalyst, and I'm not saying I was a hundred percent great in all of this. And that there's some things that I think I could have been more mature about. But the the first real catalyst was when they canceled the Obama podcast.

• 50:11Guy Raz?

  What was that? Tell me that story. Yeah, I don't know that story.

• 50:14Speaker 01

  Yeah. So spring of two thousand eight, Obama was clearly headed to probably get in the Democratic nomination. And Obama's gonna come on my podcast. And to me, it was like, this would be the greatest thing that ever happened to my podcast.

• 50:29Guy Raz?

  Yeah.

• 50:30Speaker 01

  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.

• 50:47Guy Raz?

  What? Why?

• 50:48Speaker 01

  I didn't fully understand. ESPN was very worried about.

• 50:51Guy Raz?

  Bias or?

• 50:52Speaker 01

  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 gonna happen. Like, I have a chance to talk to Obama.

• 51:05Guy Raz?

  And also, he's a sports fanatic.

• 51:07Speaker 01

  Yeah. So I took that one really hard. And then there were some other stuff behind the scenes that I was getting frustrated by.

• 51:14Guy Raz?

  Yeah.

• 51:14Speaker 01

  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 respect thing to me. And it all led to, like, I told them, like, I'm taking eight weeks off, and I'm gonna 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 LLI building. They were meeting with me and Skipper and Walsh. And within five minutes, we figured everything out. And my issue was that I just never had a real conversation with them about it. I was getting quietly frustrated, thinking they knew what was going on.

• 51:49Guy Raz?

  And they didn't.

• 51:50Speaker 01

  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.

• 52:01Guy Raz?

  That's in your head.

• 52:01Speaker 01

  And you can't assume that the people, 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. And 2009 was like, one of the best years I ever had for them.

• 52:17Guy Raz?

  That year, your book comes out, tops New York Times Bestseller list.

• 52:21Speaker 01

  And 30 came out three weeks before the book.

• 52:24Guy Raz?

  Right. But you also, still, I mean, you were working for them. So ultimately, like, you were accountable to them. Like, they could, they could hold you accountable and punish you. Like, 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.

• 52:43Speaker 01

  Yeah, I guess my issue was, maybe I didn't fully realize, sometimes, the impact. You know, my profile went way up in '09.

• 52:51Guy Raz?

  So whatever you would write would get scrutinized more.

• 52:54Speaker 01

  Yeah.

• 52:54Guy Raz?

  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.

• 53:07Speaker 01

  Yeah. And by the way, they're right.

• 53:08Guy Raz?

  Yeah.

• 53:09Speaker 01

  They should feel that way. Like, I'm working for those guys. They're paying me a salary and benefits and all this stuff. And I'm representing their company. And that was something. I feel like from oh nine on, there's like a six, five year stretch there where I really felt like I loved working for that place.

• 53:27Guy Raz?

  Yeah.

• 53:27Speaker 01

  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.

• 53:34Guy Raz?

  Hmm. One of the things that a lot of people really knew you best for was, was Grantland, right? This is a multimedia website that you basically put together in 2011 and it was part of ESPN and it was, it was amazing. And you had Chuck Klosterman and Wesley Morris and Colson Whitehead, just incredible writers writing for Grantland, uh, sports and, and pop culture. And, and it became a hugely important, like, cultural touchstone for ESPN.

• 54:03Speaker 01

  Yeah.

• 54:04Guy Raz?

  Anyway, in 2011, I guess you wanted to start it, right? So you, what did you do? You met with, uh, John Skipper, who ran content at ESPN?

• 54:12Speaker 01

  Yeah. Skipper and I went out for drinks and I just was like, I have this idea. I want to do this website.

• 54:19Guy Raz?

  And you were close with him. He was super close with John Skipper.

• 54:22Speaker 01

  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.

• 54:37Guy Raz?

  Yeah.

• 54:38Speaker 01

  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, and so sketched out this whole sports and pop culture site. Cause 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. And I was like, there's gotta 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

• 55:21Speaker 01

  they just, they didn't crack the code and I, I felt like I could. And I was really influenced by. The National and Inside Sports specifically.

• 55:29Guy Raz?

  Yeah.

• 55:30Speaker 01

  And Spy Magazine.

• 55:31Guy Raz?

  Yeah.

• 55:32Speaker 01

  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.

• 55:41Guy Raz?

  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. It was, you gotta pay those writers to write that stuff.

• 55:55Speaker 01

  I, so I'm gonna disagree.

• 55:57Guy Raz?

  Okay, all right.

• 55:58Speaker 01

  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.

• 56:19Guy Raz?

  Yeah.

• 56:19Speaker 01

  You know, if you look back at, at the people that succeeded for Grantland, it was all people that for the most part were the up and comers. It was remember Brown, it was Jay Kang, it was, we had Huasoo, we had Bill Barnwell and Zach Lowe, and we had Katie Baker. You're 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.

• 56:44Guy Raz?

  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, you were running a team of people.

• 56:55Speaker 01

  Yeah, that was, uh, which, which I was ready for in some ways because I watched Jimmy do it and I watched how we did the 30 for 30 stuff.

• 57:03Guy Raz?

  Yeah.

• 57:04Speaker 01

  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.

• 57:17Guy Raz?

  Yeah.

• 57:17Speaker 01

  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 pre-game shows live for my house. And there was an energy to some of the stuff we were trying that I think, we were trying to become a digital content epicenter for ESPN. We were trying to become this playground for them that they didn't have. And I've, 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.

• 57:54Guy Raz?

  They didn't know how to monetize it.

• 57:55Speaker 01

  Yeah, they gave it away. I mean, they sold all of our podcasts advertising the subway for $750,000 a year.

• 58:02Guy Raz?

  Right.

• 58:02Speaker 01

  When we had, it was easily six, seven, eight million dollars worth of advertising we could have gotten from the pods at that time.

• 58:09Guy Raz?

  Right.

• 58:09Speaker 01

  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.

• 58:25Guy Raz?

  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.

• 58:34Speaker 01

  I'll take the dig.

• 58:35Guy Raz?

  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.

• 58:47Speaker 01

  Yeah, I did.

• 58:48Guy Raz?

  Maybe they deserved it, but like, oh, why would you do that?

• 58:51Speaker 01

  At that point, I felt like I was team ESPN and I really, really cared about, I felt like we were winning.

• 58:58Guy Raz?

  Yeah.

• 58:58Speaker 01

  We were the dominant sports platform. And that show that day I was watching, it was First Take, it was Richard Sherman they brought on to debate Skip Bayless, who was one of the hosts. And it was just this really vicious segment. They went at it in a nasty way. And it was content that I thought like was beneath us. And should I have sent an email or a tweet? Sure.

• 59:21Guy Raz?

  Yes.

• 59:23Speaker 01

  It really came from like profound disappointment.

• 59:25Guy Raz?

  Yeah.

• 59:26Speaker 01

  And should I have said that out loud? No.

• 59:28Guy Raz?

  Fair enough. All right. I mean, so you've got, I mean, the thing is like Grantland, right? It wasn't profitable, which I don't think is, 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 recognized that?

• 59:47Speaker 01

  But you realize like the profitable thing is insane to me.

• 59:49Guy Raz?

  Okay, no, I know, I know you're hung up on that. It doesn't matter.

• 59:52Speaker 01

  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.

• 1:00:00Guy Raz?

  Right.

• 1:00:00Speaker 01

  We're bringing in an incredible amount of talent. We're in the forefront of all these things that they should care about going forward, like podcasts, like streaming video.

• 1:00:10Guy Raz?

  Yep.

• 1:00:11Speaker 01

  And you're worried that we break even?

• 1:00:12Guy Raz?

  Right.

• 1:00:13Speaker 01

  Like, we're doing great and we should be making more money than we did. So I was always like, what is that criticism?

• 1:00:17Guy Raz?

  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 this side and we're getting like, you know, younger people? Like, was anyone saying that?

• 1:00:30Speaker 01

  I think Skipper felt that way. I think my big mistake tactically was ESPN is a huge company and most of it's set 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.

• 1:00:45Guy Raz?

  Oh, they hated you guys for that?

• 1:00:47Speaker 01

  Yeah, that we had ESPN 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.

• 1:01:03Guy Raz?

  Hmm.

• 1:01:04Speaker 01

  You know, I look back, I was definitely doing too many things. And 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 Grantland, I was writing my column, I was doing my podcast, I was on NBA Countdown.

• 1:01:20Guy Raz?

  Which is television, on TV?

• 1:01:22Speaker 01

  Yeah, it was the basketball show that's before and after the games.

• 1:01:24Guy Raz?

  Yeah.

• 1:01:25Speaker 01

  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?

• 1:01:33Guy Raz?

  It all kind of comes to a head in 2014. You are on the podcast, The BS Report.

• 1:01:38Speaker 01

  Yeah.

• 1:01:39Guy Raz?

  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.

• 1:01:53Speaker 01

  And they did.

• 1:01:54Guy Raz?

  They knew.

• 1:01:54Speaker 01

  The Rice's told them, yeah. No, he lied.

• 1:01:57Guy Raz?

  And you, you went after him. And you called him a lying liar, sack of lying, lying, lying, et cetera, et cetera.

• 1:02:03Speaker 01

  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.

• 1:02:12Guy Raz?

  Oh, you dared them. You said, if you think I'm wrong, fire me or whatever.

• 1:02:15Speaker 01

  Yeah, it's like, yeah, come get me.

• 1:02:16Guy Raz?

  But why, explain why ESPN would have been worried about you calling Goodell a liar. I mean, they're an independent sports network. Why, why would they care?

• 1:02:25Speaker 01

  I think there was a tone I had in that that went probably too far.

• 1:02:28Guy Raz?

  But, I mean, they, they called your bluff, though, right? I mean, ESPN suspended you in 2014.

• 1:02:36Speaker 01

  Yeah.

• 1:02:36Guy Raz?

  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 gonna?

• 1:02:46Speaker 01

  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.

• 1:02:54Guy Raz?

  Hmm.

• 1:02:55Speaker 01

  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 it was, 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--

• 1:03:10Guy Raz?

  Yeah.

• 1:03:11Speaker 01

  Publicly, I was just trying to make it seem like everything was fine.

• 1:03:14Guy Raz?

  Yeah.

• 1:03:14Speaker 01

  I was still doing my job, but it was just getting unsustainable.

• 1:03:18Guy Raz?

  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.

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• 1:04:47Guy Raz?

  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.

• 1:05:01Speaker 01

  So I get suspended.

• 1:05:03Guy Raz?

  Yeah.

• 1:05:04Speaker 01

  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 can... And I'm hearing from like rich guy circles and people I didn't even know.

• 1:05:19Guy Raz?

  Like come, I'll invest in you. Start something new.

• 1:05:22Speaker 01

  Yeah, start, if you're gonna start something new, can we talk? Or hey, I'm, I work for here, we'll take you tomorrow. So it was weird. On the one hand, it was the worst professional experience of my career. And really, really devastating too, just like I felt so bad for the Greenland people because I had like 50 people underneath me and now all of a sudden everything's in flux and I have to figure out how to manage that and handle that.

• 1:05:47Guy Raz?

  You felt bad. I mean, you didn't walk out of there like, screw these guys. You like actually were quite sad during that time?

• 1:05:54Speaker 01

  Oh, yeah, really upset. Like we, 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.

• 1:06:13Guy Raz?

  Yeah.

• 1:06:13Speaker 01

  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 and.

• 1:06:22Guy Raz?

  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 like leave this home, this place that I've been at for 14 years.

• 1:06:33Speaker 01

  Yeah. I mean, look, it was the amount of people and it was the types of people, like famous investors and people.

• 1:06:39Guy Raz?

  Right.

• 1:06:39Speaker 01

  And I was like, holy shit. Like, 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 out 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 were so many people trying to undermine me and Skipper at that point that it just wasn't going to happen. And then.

• 1:07:07Guy Raz?

  Wow.

• 1:07:08Speaker 01

  They had a whole plan for Grantland. They brought in Chris Connolly to be the editor who wasn't really involved with Grantland. And I don't feel like Grantland should have been done in six months.

• 1:07:16Guy Raz?

  Yeah. Cause it lasted six months after you left.

• 1:07:19Speaker 01

  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 10 biggest podcasts 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.

• 1:07:41Guy Raz?

  It's totally crazy to me that they would have just let that IP evaporate like that. It's crazy.

• 1:07:47Speaker 01

  It's actually an insane business decision.

• 1:07:49Guy Raz?

  It's an insane business decision.

• 1:07:51Speaker 01

  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. And it's like, that's not how this shit works.

• 1:08:06Guy Raz?

  When you finally left, were you like energized? Were you like, yes, I'm going to start? Were you kind of sad?

• 1:08:12Speaker 01

  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 hypersensitive to any sort of me versus Goodell that they could put in a headline. So people read the news story.

• 1:08:39Guy Raz?

  Right.

• 1:08:40Speaker 01

  And Skipper saw one of the news clips and he got mad. And then I got mad that he got mad. 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 so, 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.

• 1:09:16Guy Raz?

  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.

• 1:09:38Speaker 01

  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 from 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. We didn't do it that way again.

• 1:10:19Guy Raz?

  Why didn't the HBO show work in your view, by the way? You did it for one season.

• 1:10:22Speaker 01

  Couple of 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.

• 1:10:37Guy Raz?

  Yeah.

• 1:10:37Speaker 01

  What I didn't count on was that it's just more fun to listen to a podcast. You can listen to it on your own time. You don't have to watch it.

• 1:10:44Guy Raz?

  Right.

• 1:10:44Speaker 01

  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.

• 1:10:54Guy Raz?

  Yeah.

• 1:10:54Speaker 01

  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, but really like the talk show is kinda, it's this era of like eight, nine years where it's kinda dead from a TV standpoint. Right? And my show ended up being one of, I would say 20 shows that didn't work.

• 1:11:14Guy Raz?

  Yeah.

• 1:11:14Speaker 01

  Especially sports driven talk shows. There's really no record of them working in the last 15 years. I was like, I'm gonna change that. And it was stupid.

• 1:11:24Guy Raz?

  Did that in any way like shake your confidence? Cause you know, you left ESPN, you were a big star there. And probably there are some people who are like, ha, ha, ha, his HBO show didn't work.

• 1:11:33Speaker 01

  Oh, there was definitely, I mean, there was two things. One, when I left ESPN, everybody's like, you can't leave the nest.

• 1:11:39Guy Raz?

  Yeah.

• 1:11:39Speaker 01

  ESPN's the reason you succeeded. You can't leave. You're gonna 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. And I also knew like, I'm gonna figure out some different way to make an impact.

• 1:12:11Guy Raz?

  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.

• 1:12:19Speaker 01

  Yeah.

• 1:12:20Guy Raz?

  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.

• 1:12:45Speaker 01

  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 of times during it. You're making decisions on every single conceivable thing, and you're missing some stuff, too. Like, even with The Ringer.

• 1:13:06Guy Raz?

  Yeah.

• 1:13:07Speaker 01

  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 in Cast Away. 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.

• 1:13:53Speaker 01

  So we knew The Ringer had to be different than Grantland. We couldn't have 7,000, 8,000-word pieces anymore. How do we do SEO with Google?

• 1:14:00Guy Raz?

  And you were trying to do this initially with a team of like, four people, right?

• 1:14:04Speaker 01

  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 Julia Lippman was young, but like a go getter and just like a problem solver.

• 1:14:43Speaker 01

  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 Grantland. How is it going to be different?

• 1:14:59Guy Raz?

  Yeah.

• 1:14:59Speaker 01

  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 it was The Watch with Chris and Andy.

• 1:15:09Guy Raz?

  Yeah.

• 1:15:09Speaker 01

  And they would just come over. They, 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.

• 1:15:26Guy Raz?

  That was financing the whole operation.

• 1:15:28Speaker 01

  Not all of it, but a lot of it. Cause we, we were a couple of years ahead of people on the podcast front.

• 1:15:33Guy Raz?

  Yeah.

• 1:15:33Speaker 01

  And by the time the competitors came.

• 1:15:36Guy Raz?

  You had a structured audience. Yeah.

• 1:15:37Speaker 01

  We were too established. Yeah. So we, and we found a lot of talent. Like even like we had the Pod Save America guys, that podcast started with us in 2016.

• 1:15:46Guy Raz?

  Right.

• 1:15:46Speaker 01

  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.

• 1:15:53Guy Raz?

  And making those podcasts wasn't expensive.

• 1:15:55Speaker 01

  No, wasn't expensive. And then the big thing for me is, did we want VC money or not?

• 1:16:02Guy Raz?

  Yeah.

• 1:16:03Speaker 01

  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 were like, we're not, 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.

• 1:16:46Guy Raz?

  Right. Ultimately, you did raise money.

• 1:16:49Speaker 01

  Yeah, so was HBO put in five million bucks as part of, they didn't want me to do The Ringer.

• 1:16:55Guy Raz?

  Right.

• 1:16:56Speaker 01

  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.

• 1:17:08Guy Raz?

  Yeah.

• 1:17:08Speaker 01

  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.

• 1:17:17Guy Raz?

  And that was it?

• 1:17:18Speaker 01

  And that was it.

• 1:17:18Guy Raz?

  You didn't raise any subsequent money after that?

• 1:17:21Speaker 01

  No.

• 1:17:21Guy Raz?

  Nothing?

• 1:17:22Speaker 01

  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, I'd made a lot of money at ESPN and I was just like, I'm betting on myself.

• 1:17:33Guy Raz?

  Yep.

• 1:17:33Speaker 01

  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.

• 1:17:43Guy Raz?

  And all of the articles initially would be written by a collection of freelancers?

• 1:17:48Speaker 01

  No, we had, we went, by the time we launched the website, we probably had like 40 employees.

• 1:17:52Guy Raz?

  Which was in?

• 1:17:53Speaker 01

  June 2016.

• 1:17:55Guy Raz?

  Wow. I mean, initially you launched it on Medium, right? On that platform?

• 1:18:00Speaker 01

  Yeah, so that was one of the big decisions was, do we build our own website?

• 1:18:04Guy Raz?

  Yeah.

• 1:18:04Speaker 01

  It was just Medium was basically the website host.

• 1:18:06Guy Raz?

  Right.

• 1:18:07Speaker 01

  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 at Vox. So this was kind of a half-assed way of doing that where we got to kind of be on Vox. They got to participate in the profit stuff and.

• 1:18:22Guy Raz?

  You did a deal with them?

• 1:18:23Speaker 01

  Yeah, we did a deal with them.

• 1:18:24Guy Raz?

  So all 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?

• 1:18:34Speaker 01

  Well, there was one other piece, we had mid-roll.

• 1:18:36Guy Raz?

  Mm-hmm. This is an ad sales company, mid-roll.

• 1:18:38Speaker 01

  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, of the price and that's it.

• 1:18:47Guy Raz?

  How did you, just help me understand how you managed 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.

• 1:19:03Speaker 01

  No, I actually disagree. I like the business side. I think the surprising thing for me with The Ringer was how much I liked 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 them-

• 1:19:22Guy Raz?

  That motivated you. It was your Michael Jordan, like, another log on the fire.

• 1:19:25Speaker 01

  No question.

• 1:19:26Guy Raz?

  That I understand. That motivation and anger 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.

• 1:19:46Speaker 01

  Yeah.

• 1:19:46Guy Raz?

  How did you do that?

• 1:19:48Speaker 01

  Maybe I'm a psycho, but I like all that stuff. I think the thing I learned at Grantland 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.

• 1:20:11Guy Raz?

  Yeah.

• 1:20:12Speaker 01

  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. Like, I was the one that ultimately was deciding all the money stuff. And that, 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. And, but yeah, I think it's fucking hard.

• 1:20:37Guy Raz?

  Yeah. You launched this thing in 2016.

• 1:20:41Speaker 01

  We launched a website in 2016, like the podcast basically launched in 2015. Yeah.

• 1:20:47Guy Raz?

  Right. And 2020, right before the pandemic, it was announced that you sold to Spotify.

• 1:20:55Speaker 01

  Yep.

• 1:20:55Guy Raz?

  For around $200 million.

• 1:20:57Speaker 01

  250.

• 1:20:58Guy Raz?

  Give or take 250. And I mean, it's sort of a dumb question, which is why? Because it's $250 million is 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 off 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?

• 1:21:24Speaker 01

  Yeah, it started, um, they had approached us like maybe the start of 2019, something like that. Or late, 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, 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 we didn't want, 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.

• 1:22:08Speaker 01

  I didn't want to be in another big company. And then they bought Gimlet and they bought Gimlet for like $200 million.

• 1:22:15Guy Raz?

  Yeah.

• 1:22:16Speaker 01

  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.

• 1:22:25Guy Raz?

  Yeah.

• 1:22:26Speaker 01

  So that got our wheels turning a little bit, but I still didn't want to sell. And started it, we, we lost out on a couple of people.

• 1:22:32Guy Raz?

  Lost out who went to other, other places.

• 1:22:35Speaker 01

  Talent stuff.

• 1:22:35Guy Raz?

  Yeah.

• 1:22:36Speaker 01

  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 five 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.

• 1:22:56Guy Raz?

  Yeah.

• 1:22:57Speaker 01

  My goal the whole time was always like, if I get hit by a bus tomorrow, would the Ringer 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.

• 1:23:26Guy Raz?

  Yeah.

• 1:23:26Speaker 01

  And I was like, these guys are going to be the future of audio if they already aren't now. And, and maybe this is a place that could supercharge us. But we didn't, we never shopped around. People didn't know we were for sale.

• 1:23:38Guy Raz?

  Huh.

• 1:23:38Speaker 01

  It was like Spotify or we're not doing anything.

• 1:23:41Guy Raz?

  Well, 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.

• 1:23:51Speaker 01

  Yeah.

• 1:23:52Guy Raz?

  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?

• 1:24:16Speaker 01

  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.

• 1:24:24Guy Raz?

  With like Twitter and social media and people just like.

• 1:24:27Speaker 01

  Yeah, and it's just, 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.

• 1:24:36Guy Raz?

  Yeah.

• 1:24:36Speaker 01

  I think it has made it a little more formal than it used to be.

• 1:24:40Guy Raz?

  Yeah.

• 1:24:41Speaker 01

  I definitely talked to less people than I used to.

• 1:24:43Guy Raz?

  Yeah.

• 1:24:44Speaker 01

  But at the same time, every generation has its challenges, right? And I think, to me, Twitter is causes a lot of the stuff because people can just run to Twitter and.

• 1:24:54Guy Raz?

  Yeah.

• 1:24:54Speaker 01

  I always wonder like, if we just didn't have Twitter, would some of the stuff be easier? But who knows?

• 1:24:59Guy Raz?

  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 that the ability for people to grow and develop and to become, you know, to just to learn from people who've been there before.

• 1:25:19Speaker 01

  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 creatively, we had podcasts that developed just from the Ringer office those first couple of years where like, I remember hearing this guy Danny Heifetz 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 gonna lose all of those moments.

• 1:26:01Guy Raz?

  Yeah.

• 1:26:01Speaker 01

  The spitballing is what gets hurt. You can't do it on Zoom. You can't.

• 1:26:06Guy Raz?

  Bill, how long are you committed to being part of Spotify, to being part of The Ringer?

• 1:26:12Speaker 01

  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 upon 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 is 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 and they have a huge audience.

• 1:26:41Guy Raz?

  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.

• 1:26:52Speaker 01

  Yeah, I don't know. I go back and forth on that because at one time I, I thought like, oh, Spotify, this will be it. And then I, how long am I going to work this hard? You know, and then just manage 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?

• 1:27:23Guy Raz?

  Yeah.

• 1:27:24Speaker 01

  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?

• 1:27:32Guy Raz?

  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 had to do with luck?

• 1:27:54Speaker 01

  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 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.

• 1:28:20Guy Raz?

  Yeah.

• 1:28:20Speaker 01

  Like 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 realized 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, 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

• 1:29:05Speaker 01

  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.

• 1:29:16Guy Raz?

  That's Bill Simmons, Boston Sports Guy and founder and managing director of The Ringer.

• 1:29:23Guy Raz?

  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? Like, he cheated and they should never even consider it?

• 1:29:34Speaker 01

  I think all of those guys should be in the Hall of Fame.

• 1:29:36Guy Raz?

  Really? Barry Bonds, Mark McGuire, even though they cheated?

• 1:29:40Speaker 01

  Yeah, just put it on the plaque. If I'm taking somebody to 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.

• 1:29:53Guy Raz?

  The Room of Cheaters Plaques.

• 1:29:55Speaker 01

  Cheater Room. Whatever you want to call it. Yeah, sounds great.

• 1:29:58Guy Raz?

  Son, I want to show you this inspiring room here at the Hall of Fame, the cheaters room.

• 1:30:02Speaker 01

  Yeah, son, don't do what these guys did. That's the whole point of being a museum.

• 1:30:08Guy Raz?

  Hey, thanks so much for listening to the show this week. If you want to contact our team, our email address is [email protected]. 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 dot Raz. This episode was produced by Alex Chung with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Sam Paulson. Our production staff also includes Casey Herman, J.C. Howard, Kerry Thompson, Kira Wakim, Elaine Coats, John Isabella, Chris Messina, and Carla Estevez. I'm Guy Raz, and you've been listening to How I Built This.