The media mogul you’ve (probably) never heard of

Bill Simmons, former sports writer, is the founder and CEO of American pop culture site The Ringer, which was recently acquired by Spotify for a reported $200 million.

Huge disclaimer: if you live in America or follow American sport, then you (probably) will have heard of Bill Simmons. Since neither of those are true of me - and since I’m probably going to be the only person who reads this article - the song remains the same. The title of the article would be more accurate if it ended with ‘… if you’re from the UK’, but that doesn’t look as eye-catching on the site. Please, please have mercy on my soul.

Bill Simmons’ CV is very impressive. He was hired as a sports writer by ESPN and eventually became an on-screen pundit for the channel’s live NBA coverage. He was pursued and persuaded to move to Los Angeles to write for Jimmy Kimmel’s late night talk show. His podcast, The Bill Simmons Show, is the most downloaded sports podcast of all time. He conceived and produced ESPN’s 30 for 30 documentary series. He has interviewed Barack Obama - twice. His podcast has hosted guests like Charlize Theron, Matt Damon, Judd Apatow and Paul Thomas Anderson. His latest venture, The Ringer, is a website and podcast network with 39(!) original shows that was purchased by Spotify for $200m at the beginning of 2020 – though Simmons retains creative control of the site’s output. The sale means Simmons is the first podcaster to make it on to Forbes’ Celebrity 100 list.

How does someone achieve this? Links to the American East Coast media elite? Family connections? Is it as the old saying goes, and in fact not who you know but who you blow?

Not in Simmons’ case. Born in Massachusetts, he moved to Connecticut aged 13 when his parents divorced. He attended the College of the Holy Cross, one of the oldest Catholic colleges in America (who knew that was a thing?), and graduated with a BA in Political Science in 1992. The final step of his education journey was completing a master’s degree in Print Journalism from Boston University.

So was this the stage where, free from the shackles of higher education, Bill Simmons found his audience and took the media world by storm, disrupted the old guard and ushered in a new dawn of exciting everyman journalism?

Nope. Simmons spent three years in various entry-level media jobs, ‘answering phones and doing shit work’, and propping himself up with bartending work in between. At age 28, Simmons persuaded a Boston-based digital publication, operating on AOL’s private site network, to host his column. A departure from the traditional print journalism world of his master’s degree, this was something very different. A suspicious new world known as - *lowers voice* - The Internet. Simmons probably wondered whether it would catch on, but at least it could serve as an outlet for his writing. With that, BostonSportsGuy.com was born.

Initially, Simmons shared his site with friends and, via the subsequent word of mouth, was circulating the content of his AOL-only site with a solid group of around 100 readers. I don’t imagine this word of mouth success was a devious plan packed with foreshadowing like Jesse Eisenberg’s Mark Zuckerberg in Social Network (‘question is – who are they gonna send it to?’), and I don’t imagine Zuckerberg’s partner Eduardo Saverin supplied him with the Phoenix club’s mailing list, but who knows? Maybe that’s how things work in Boston. 18 months later, BostonSportsGuy.com was now available outside of the AOL network and his following started to snowball.


“The main thing I noticed was none of them were writing about the stuff I talked about with my friends. The stuff we were doing – going to Vegas, watching football for 10 hours, playing video games – wasn’t represented”

- Bill Simmons


By 2001, Simmons’ blend of passionate sports writing (mainly on the subject of his favoured Boston teams) and pop culture references was pulling in 45,000 site hits per day. One of the techniques Simmons’ would use was to use quotes from a particular film to sum up a season, assigning each quote to a specific person or memorable incident. He would often discuss his personal life and gambling exploits. This unique approach to journalism set Simmons apart from the run-of-the-mill sports writer and, combined with his impressive following in the early days of the internet, it wasn’t long before the big dogs took notice.

ESPN – ‘the worldwide leader in sports’ – came calling, initially hiring Simmons to write three guest columns. The reception to ESPN’s new guest star was overwhelmingly positive and he joined permanently, given his own section of ESPN’s Page 2 site which doubled its readership in less than two years. At his stage, Simmons was considered a pioneer of online sports writing and his column averaged 500,000 visits per month. With his stock at an all-time high, Simmons went on to put his finger in the pie of pretty much everything you could imagine would be possible whilst working for ESPN. He co-conceived the 30 for 30 documentary series – 30 sports films to celebrate ESPN’s 30-year anniversary. The series was critically acclaimed and continued to produce films after the initial run, ultimately resulting in the Academy Award for Best Documentary for OJ: Made in America in 2017. Simmons found himself on-screen as a pundit for ESPN’s live NBA coverage, still employing the same unique approach to his role in front of the camera that resulted in a feud with the coach of the New York Knicks, Isiah Thomas.

Success at ESPN eventually led to Simmons becoming editor-in-chief of Grantland in 2011, a site owned by ESPN but run by Simmons, with a site-wide approach for the sport & pop culture crossover content that is the foundation for his current venture – The Ringer. The relationship between ESPN and Simmons started to decline, rumoured to be due to Simmons’ criticism of senior figures at the broadcaster, and it was announced that his contract wouldn’t be renewed after 2015.

The Ringer was launched in 2016 and signalled a shift in priority for Simmons, as he stepped away from writing duties and focused more on podcasting. His podcast on ESPN, The BS Report, was the most downloaded on the network, averaging 2 million downloads per month. The Ringer’s focus on podcasting suggests that Simmons anticipated the recent podcast boom and made the right decision to move in a new direction with a fresh focus. The site now boasts 39 original shows on their podcast network.

It is via The Ringer’s podcasts, found randomly on Spotify, where I first encountered Bill Simmons. The absolute jewel in the crown is The Rewatchables, where each episode is built around a discussion on a specific ‘rewatchable’ film. Simmons is normally host, flanked by his 2 deputies, Sean Fennessey and Chris Ryan, who both joined The Ringer after working with Simmons at Grantland. These three would be what is referred to as The Classic Panel (in my head), but other Ringer employees do make appearances depending on the film. They make their way through a set of categories to dissect the film – most rewatchable scene, best quote, what aged the best and worst in the film, Simmons’ ‘half-assed’ internet research, unanswerable questions (about the plot), nit-picking, awards for overacting, casting ‘what-ifs’, career peak conversations and who ‘won’ the film, in terms of the impact this film had on the rest of their career or influence in the film industry. For me, it’s the most entertaining film podcast on offer and is a perfect balance of casual conversation, comedy and informative listening about a wide range of films. It looks like Quentin Tarantino and I agree on this, as he guest-hosted the 98th, 99th and 100th episode of The Rewatchables to cover three of his favourite films of the last 30 years. Along with The Bill Simmons Show, an honourable mention must go to The Big Picture, another film podcast on The Ringer network. Hosted by Sean Fennessey, who is often joined by co-host Amanda Dobbins, the podcast normally features a deep-dive on a film-related issue, dissects the career of an actor or director, or looks towards awards season. It’s not surprising that Spotify took the opportunity to add The Ringer to its expanding network of original content.

To understand what makes Bill Simmons appealing, it might be useful to compare him to another of Spotify’s recent big money signings. Spotify handed Joe Rogan a multi-year contract worth an estimated $100m to bring The Joe Rogan Experience exclusively to Spotify. Rogan attracts some seriously big name guests, then spends what feels like 10 hours discussing a conveyor belt of niche/ridiculous/pretentious (take your pick based on personal opinion on Rogan) topics. Rogan loves to invite his guests in to discuss things like hunting and eating raw elk flesh, and the feel of the conversation is normally extremely intense and serious, as if these are the most important discussions ever to be committed to record. Simmons’ podcast output, in comparison, is light-hearted and often feels like you are listening in to something recorded by your actual real-life friends.

A particular moment from The Rewatchables episode on Richard Linklater’s coming of age belter Dazed and Confused (a great episode in general) sticks in my mind as a direct contrast to the ostentatious conversations on The Joe Rogan Experience. The panel are discussing the scene where Matthew McConaughey’s Wooderson enters the smoke-filled pool-hall hangout in slow motion, as Bob Dylan’s Hurricane plays. One of the panel asks Bill what song he would pick for that iconic entrance, if the film was about his life. Without missing a beat, he answers “I think that one”, to the hilarity of Fennessey and Ryan. The way it plays out captures how Simmons’ carries himself – a wide-eyed everyman who loves what he has seen on screen and is happy to shamelessly wear that on his sleeve. Others in the same position would probably have a pre-meditated answer of a cool but obscure song to really show off. The team that Simmons has built around him at The Ringer is the perfect foil for this persona, and he also beefs that up by having friends and family members as regularly recurring guests on his podcast – Cousin Sal and his dad, Bill Sr., both appearing to offer their insights on the hot current affairs topics. Not something you would expect to find on many other podcasts that were just subject to a multi-million dollar purchase from one of the world’s biggest media companies.

So what’s next for Bill Simmons, after The Ringer’s $200m sale? The Swedes at Spotify reportedly see The Ringer as the next ESPN and think they can become the next voice for global sport. Considering the journey from writing his sports column whilst bartending, to a place on a Forbes’ rich list and the top of the podcast game, I don’t think we can rule anything out.

 
Previous
Previous

‘This is the first time we’ve ever played outside’