The Podcast King: Bill Simmons has a Voice and Reach

Podcasting is an easily accessible technology and medium. Podcasts kits are sold on Amazon and content is relatively easy to place on podcasts providers. This resulted in droves of shows that were obscure, flat, and poor in quality. Apple or Spotify are littered with shows that have gone dormant having thrown in the towel. Meanwhile, a much smaller number of popular, professional pods attract millions of loyal listeners willing to subscribe and be subjected to ads.

Joe Rogan opines on controversial topics, Mel Robbins pods to help change your life, and Conan O’Brien chats with stars and the general public. Every topic imaginable can be found and the format of podcasts is quick, easy, and digestible. When you spot someone in the grocery store with headphones, they could be listening to a cooking show. People driving are devouring true crime and political pods.

As the cream has risen to the top, it’s become a big, new media industry. You probably haven’t heard of Bill Simmons, but he saw this coming. Simmons recently sold his multi-podcast media company, The Ringer, to Spotify for nearly US$200 million plus performance incentives. He is first and foremost, a sports guy. Simmons got his start at ESPN and quickly developed an audience through a style of writing that was direct but conversational.

That ported well into the world of podcasting. The Bill Simmons Podcast is a must-listen for sports enthusiasts. He does his research, provides insights, and holds his ground. So much so, that his opinions have created feuds with everyone from Isiah Thomas to Harry and Meghan. While employed at ESPN, he was suspended multiple times. On the other side of the ledger, Simmons has written two New York Times bestsellers, collaborates with HBO, and rubs shoulders with leading sports figures and celebrities who know his words and reach carry weight.

It was on The Ringer podcast, The Rewatchables, that I discovered Simmons. It is a film review show that brings out Simmons’ personality. He is joined by a rotating roundtable of people from The Ringer discussing movies they can’t seem to stop rewatching. The films reflect Simmons’ history as a teenager in the 1980’s. Recent films covered include Fast Times at Ridgemont High, Roadhouse, and Risky Business. The discussions are illuminating as Simmon’s colleagues are movie experts but he drives the show.

He mixes sports terms and analogies, personal experiences, along with references to broader pop culture. It’s obvious he appreciates movies and television as much as sports. I have watched The Fugitive too many times to count but when Simmons and colleagues covered the film, I got more out of it than ever could have be expected.

Simmons is always good for an observation, quip, and quote, “In 1994, nobody could have predicted ‘Shawshank’ would one day be an iconic movie — and believe me, that would never have happened if Danny Glover had been Red instead of Morgan Freeman.” And he is not afraid to stray, “When I was in elementary school, we had the kid who threw chairs, the kid who stuttered, and the kid who went to the bathroom on himself … but we never had the kid who came in one day and started shooting everyone.”

I’m more pop culture than sports so also enjoy The Ringer’s The Town pod which covers the inside doings of Hollywood and The Big Picture which is a more deliberate and structured look at films and filmmaking. The latter is like taking a fascinating course. There is also What Went Wrong covering the challenges of making films and Trial By Content that ranks best movie genres. It has also addressed best first date movies and best body-swap films.

All of this proves that Simmons knows what people likes to consume in content. He has assembled professional podcasters to lead these shows and gives them room while staying in control. Each pod reflects his personality which has curiosity at the core. Simmons also knows how to monetize. This is demonstrated in his deal with Spotify where he was able to retain The Ringer Brand. And individual pods are sponsored like The Rewatchables which is presented by Pizza Hut.

Simmons is now a celebrity in his own right. Earlier this year, he was obviously thrilled to be a guest on Fly on the Wall with Saturday Night Alums Dana Carvey and David Spade. Simmons’ knowledge of this show and its influence on him was evident. He schooled the two comedians on the show’s history. Simmons was prescient when it came to podcasting but succeeds because he is passionate about the content and does the work.