Feb 13, 2023 · 1h 21m · how-i-built-this
The Ringer: Bill Simmons
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, sports media pioneer Bill Simmons details his journey from an unconventional digital columnist and innovative ESPN creator to the founder of The Ringer, leading to its landmark $250 million acquisition by Spotify.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 28.5% of the talking time here. How this is scored →
Guy as informed peer 3.9 Guest teaching 3.7 Guest disagreement 2.3 Guy pushing back 1.8
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:18:45 Bill rejects Guy's luck framing as a loser attitude
Bill forcefully pushes back against Guy's question about luck versus grind, arguing that attributing success to luck is a cop-out.
Hardest push from Guy ▶ 49:45 Guy confronts Bill over attacking colleagues on TwitterGuy directly challenges Bill on whether he was needlessly stirring up internal drama by publicly trashing First Take on Twitter.
Biggest teaching moment ▶ 47:15 Bill corrects Guy on Grantland's talent acquisition strategyBill counters Guy's assumption that Grantland blew its budget on expensive established writers by detailing how they discovered and developed young talent.
Guy holds their own ▶ 4:35 Guy demonstrates command of 1970s NBA loreGuy immediately identifies the legendary 1976 NBA Finals Game 6 against Phoenix as the iconic triple overtime contest without missing a beat.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Childhood Boston Sports Fandom and 1970s Celtics Memories | 5 | 4 | 1 | 1 | Guy demonstrates sports historical knowledge by identifying the 1976 Finals Game 6 as triple overtime, while Bill enriches the story with deep context on the 1970s NBA access and racial dynamics explored in Halberstam's work. | |
| Relocating to Connecticut and Halberstam's Formative Influence | 4 | 3 | 1 | 1 | Guy guides Bill through his move to Connecticut and college writing at Holy Cross, lightly checking details like Bill's parents' divorce timeline. Bill details how his provocative college columns against basketball coach George Blaney shaped his voice. | |
| Boston Herald Frustrations and the Unprinted Page Pitch | 3 | 3 | 2 | 1 | Guy probes Bill's early frustrations and cockiness at the Boston Herald. Bill explains how he mocked up an unprinted multimedia-style newspaper page ahead of its time. | |
| Digital City Boston and the Dawn of Online Sports Writing | 5 | 4 | 2 | 1 | Guy and Bill discuss the emergence of online sports media, with Guy recognizing Peter Gammons' pivotal role. Bill details how Sports Illustrated completely miscalculated the digital transition compared to ESPN. | |
| Landing at ESPN Page 2 and Mid-Show Break | 4 | 3 | 2 | 2 | Guy asks about the access game and sports journalism norms. Bill shares how his approach of openly rooting and weaving pop culture into columns broke the traditional detached mold. | |
| Writing for Jimmy Kimmel and Covering the 2004 Red Sox | 3 | 2 | 1 | 1 | Guy asks about Bill juggling writing for Jimmy Kimmel Live while continuing his ESPN column, culminating in his return to full-time writing during the 2004 Boston Red Sox championship run. | |
| Pioneering 30 for 30 and The BS Report Podcast | 3 | 4 | 3 | 2 | When Guy suggests nobody was listening to early podcasts in 2007, Bill rejects the premise, pointing out web streaming traffic and early chart dominance before celebrity traction arrived. | |
| Rising Internal Tensions: The Canceled Obama Podcast | 4 | 3 | 2 | 2 | Guy presses Bill on his internal disputes at ESPN, specifically the squashed 2008 Barack Obama interview. Bill reflects candidly on corporate equal-time policies and his own early management blind spots. | |
| Launching Grantland and Fighting Internal Monetization Hurdles | 5 | 6 | 5 | 4 | Guy challenges Bill on whether Grantland was heavily expensive and whether Bill unnecessarily stirred up trouble by attacking First Take on Twitter. Bill directly disagrees on the budget strategy, noting they scouted young undervalued talent rather than overpaying veterans. | |
| The Roger Goodell Critique, Suspension, and Mid-Show Bumper | 4 | 3 | 3 | 3 | Guy asks why ESPN cared so much about calling Roger Goodell a liar over the Ray Rice scandal, prompting Bill to admit his public dare to ESPN management was an unforced error that fractured his relationship with the network. | |
| The Collapse of Grantland and Departure from ESPN | 4 | 4 | 2 | 1 | Bill recounts the emotional turmoil of Grantland's rapid demise within six months of his exit, while Guy expresses disbelief that ESPN let such valuable intellectual property disintegrate. | |
| The Short-Lived HBO Talk Show and Recovering from Failure | 3 | 4 | 2 | 1 | Guy explores Bill's post-ESPN stumble with Any Given Wednesday on HBO. Bill delivers a frank autopsy of why the TV format failed compared to longform audio. | |
| Founding The Ringer and Building an Independent Media Engine | 4 | 4 | 3 | 2 | When Guy suggests Bill dislikes the business side of media, Bill disputes this, explaining his drive to build The Ringer out of competitive spite against ESPN and detailing his operational boot-strapping. | |
| Sizing Up Spotify and the $250 Million Sale | 4 | 4 | 2 | 1 | Guy examines The Ringer's sale to Spotify, prompting Bill to clarify the valuation numbers and explain why seeing Gimlet's acquisition prompted them to evaluate their long-term position against media giants. | |
| Evolving Management Dynamics in the Modern Workplace | 4 | 3 | 2 | 2 | Guy and Bill discuss modern workplace culture, remote work drawbacks, and managing teams in the social media era, agreeing on the loss of spontaneous office collaboration. | |
| Long-Term Ambitions and Rejecting the Concept of Luck | 4 | 5 | 4 | 3 | When Guy asks how much of his career success stems from luck versus grind, Bill vehemently rejects attributing success to luck, calling that framing a loser attitude. They close with a lively debate on admitting steroid-era players into the Hall of Fame. |
Statements from this episode (25)
Simmons: 1976 Celtics-Suns Finals game probably remains the most famous modern NBA game
“Yeah, it became the most famous modern NBA game, and it probably still is.”
Simmons: Early Newspaper Pitch Presaged Future Internet Column Formats
“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 work column. It had these lists. It looked a lot like kind of what the internet would lo…”
Simmons: Peter Gammons joining ESPN.com legitimized online sports journalism
“The most important thing that happened with the internet and sports writing was when Peter Gamitz got hired by ESPN. He had the most important baseball column. And it was the single most important baseball column for 25 years. When it went to ESPN.com. ESPN.co…”
Bill Simmons Says Sports Illustrated Completely Fumbled the Digital Era
“Sports Illustrated was the dominant sports magazine. And Sports Illustrated missed it. Like, they completely effed up the internet. A little like how Rolling Stone missed with MTV in the eighties. Sports Illustrated missed with sports in the late nineties, ear…”
Simmons: Sports journalists cannot be authentic without personal fandom
“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 wha…”
Simmons: Writers only retain audiences by being unpredictable and adding creative hooks
“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?”
Simmons: Writing 10,000 to 11,000 words weekly at ESPN caused burnout
“I was writing 10, 11,000 words a week. And it was unsustainable. Like I really started to burn out and Jimmy came along.”
Simmons: Column writing has a shelf life as readers tire of writers' voices
“People get tired of writer's voices. I'm going to run out of things to say at some point.”
Simmons: Yahoo tried to recruit him away from ESPN in 2007
“That I had, my contract was coming up the beginning of oh seven and Yahoo was trying to get me to jump over, which I didn't want to do.”
Simmons: ESPN canceled scheduled 2008 Obama interview over political bias concerns
“ESPN squashed it, and they squashed it for reasons that... I didn't fully understand. ESPN was very worried about... Bias, or... Seeming like they were biased one way or the other, with Democrats, Republicans, whatever it was. And they were just like, well, yo…”
Simmons: ESPN paid Rick Reilly more despite Simmons being more important
“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.”
Simmons: Grantland broke even and produced nine of ESPN's top ten podcasts
“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.”
ESPN Undersold Grantland's $8M Podcast Ad Inventory For $750k, Says Bill Simmons
“They sold all of our podcasts advertised in the subway for 750,000 dollars a year. When we had, it was easily six, seven, eight million dollars worth of advertising we could have gotten from the pods at that time.”
Bill Simmons: NFL Commissioner Roger Goodell lied about Ray Rice
“And they did. Though Rice's told them. No, he lied.”
Simmons: ESPN relationship was irreparable after unpaid suspension
“I think that thing that really got me was that I got suspended without pay for the first two weeks, and I already felt like I was underpaid for them, and I was killing it for them, and it was kind of irreparable after that.”
Simmons: Long-form interviews work better as podcasts than TV shows
“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.”
Simmons: Sports-driven talk shows have not worked on TV in 15 years
“Especially sports-driven talk shows, there's really no record of them working in the last 15 years.”
Simmons: Pod Save America podcast originally started at The Ringer
“Like even like we had the pod save America guys, that podcast started with us.”
Simmons: HBO invested $5 million into The Ringer
“HBO put in five million bucks as part of, they didn't want me to do the ringer. They wanted me to do the TV show and that's it.”
Bill Simmons Was Shocked Spotify Paid $200M For Gimlet's $10M Revenue
“And then they bought Gimlet and they bought Gimlet for like two hundred million dollars. And we were like, wow, Gimlet makes like Ten million dollars a year. They just got two hundred million dollars. Like, what the hell? Like, we were way more profitable than…”
Simmons: Creative Spitballing Cannot Happen Over Zoom
“The spitballing is what gets hurt. You can't do it on Zoom. You can't.”
Simmons: ESPN was much more political and sinister than Spotify
“I think ESPN was way more political and way more sinister. Spotify's not sinister, but it's also a big company that has a lot of opposing objectives”
Simmons: Attributing career success to luck is a 'loser attitude'
“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 o…”