A week ago ESPN refused to resign Bill Simmons to a new contract. Mr. Simmons has spent 15 years with ESPN and created some of ESPN’s most edgy content platforms by not being afraid to challenge rules and break new ground. We believe that he’s the sports entertainment version of Howard Stern. There are many similarities in their careers and we will list a handful of them below.

Secondly, we strongly believe that with Mr. Simmons being available on the open market, his next move will decide how we will be enjoying sports and pop culture commentary in the future. Unlike Stern who left the mothership of terrestrial radio for an over leveraged high tech satellite company (somebody has to pay for the rockets), Simmons will be able to create and run a new media company in the friction free content distribution age of YouTube, Snapchat and Periscope.

First A Comparison Of Media Titans

An uninformed critic of Howard Stern might believe that the only thing he talks about is sex or bodily functions. In closer inspection, Mr. Stern has created an ecosystem of talented contributors and an interview format that is second to none when it comes to engaging, truthful celebrity interactions. In a similar way Bill Simmons has been able to elevate and deepen the sports conversation from a fan’s perspective. Both men have rabid fan bases who look forward to every interaction and smaller but extremely vocal detractors who believe they cross a line with their honest curiosity.

Here is a list of similarities these men both share:

Their Loyal Producers


Gary Dell’Abate vs David Jacoby

They both have surrounded themselves with highly competent and extremely loyal producers. Mr. Dell’Abate is the executive producer on the Stern Show and has worked with him for almost 40 years. He also hosts his own radio program on the channel that provides meta commentary around things that happened on the main show. David Jacoby is one of Mr. Simmon’s producers and himself has created and run several new meta podcasts. It is only a matter of time before Jacoby joins Simmons at his new venture. (The Jalen Jacoby podcast from May 18th even hinted at it)

Their Overweight Gambling Obsessed Friends


Artie Lange vs Sal Iocano

Mr. Lange spent 8 years as an on-air contributor on the Stern Show. His gambling exploits were well featured. Mr. Iocano (Cousin Sal) joins Simmons throughout the NFL football season on a weekly podcast where betting lines and strategies are discussed and established. Both Artie and Sal have shown a penchant for self abuse with Artie battling his demons of alcohol and heroin, while Sal has shown blind and unfulfilling reverence for Tony Romo, the Dallas Cowboys and the baseball NY Mets.

Their On Air Friends

Whack Pack vs Bizarro Whack Pack


The Stern Show has had a stable of on-air talent from a collection of misfits since the beginning. These people seem to exist only to serve in Stern’s universe and all have distinct voices and stories outside of society’s norm. From Eric the Actor (RIP) to Beetlejuice to Hank the Angry Dwarf and High Pitch Eric, each person provides a definitive viewpoint. In Bill Simmons created universe, he’s been able to assemble a group of regulars who are on the exact opposite of the society norm scale. Bill surrounds himself with bestselling authors and some of the greatest thinkers of our day. Malcolm Gladwell, Nate Silver, Chuck Klosterman, Wesley Morris, Chris Connelly and many more join the podcast or contribute articles to discuss sports and pop culture. Simmon’s group of regulars could be assembled to form a New Media Algonquin Round Table.

Their Fines and Suspensions


Howard was famously fined by the FCC for inappropriate things said on the nation’s public airwaves. He’s been chided by his superiors and left terrestrial radio for the friendly uninhibited airwaves of satellite radio. Bill Simmons has been suspended by the ESPN network a few times when he’s challenged sports leaders and players. Calling the NFL Commissioner Roger Goodell a liar earned him two weeks unpaid suspension just recently.

Found Mainstream Legitimacy on Panel Driven National TV


Howard Sterns tenure at “America’s Judge” on America’s Got Talent on NBC has brought Stern attention and new fans on national TV. His honesty and straight opinion have been corner stones to his radio show for decades, but now kids and families get to see his brilliance. Bill Simmons career was mostly spent on ESPN.com writing 20,000 word essays covering sports from a fans perspective. His gig working on ABC’s NBA Countdown for two seasons brought a much larger audience who might not have ever read his columns.

They both went to Boston University. They both use their dad’s regularly as on-air talent. They both have deep ties with Jimmy Kimmel. They have no fear of trying other media formats (cartoons or TV specials) to give their fans new ways to enjoy them. The comparison goes on and on.

Bill Simmons Could Break Open The Paid Micro Content Market

His decision is similar to what Howard Stern had back in 2006. Stern left terrestrial radio for the new and unproven market of satellite radio. When Howard Stern joined Sirius, they had fewer than 500k paid subscribers and were in the middle of a fierce battle with their competitor XM. 9 years later, XM has been acquired by Sirius and over 27.7 million paid subscriptions are processed each month. Every major car manufacturer has satellite radio built in and its clear that with Howard’s influence and audience, they were able to thrive on satellite and put terrestrial radio on life support.

Bill Simmons has the same level of potential by joining an online streaming content company. Netflix. Hulu. Facebook. Periscope. Bill Simmons will be working at one of these companies by the time the NFL season comes round in the fall. It shouldn’t be Fox. It shouldn’t be NBC. Bill Simmons greatest impact and revenue potential will come from where the younger demographic spends most of their time. And that’s not sitting in front of a television.

Will he take the plunge and try a paid subscription model for his content? Would you pay 50 cents to download a podcast? This is something that Tim Ferris has been experimenting with and has been having tremendous success. Only Bill Simmons has an audience that could scale this to a HUGE revenue generation machine.

The worlds largest hotel company doesn’t own any hotels (AirBRB). The worlds biggest taxi company doesn’t own any cars (Uber). And Bill Simmons could build the worlds largest sports entertainment organization and never have to pay for licensed live sporting events.

So our prediction is he spends the summer traveling with his family. Grows a beard. And come October rolls out something that will have reverberations throughout sports media.

Bye for now.


We were alerted to an especially cogent article written 6 years ago before Simmons started Grantland for ESPN. It suggest that a new media entity with Howard Stern, Bill Simmons and Adam Corolla. To quote:

Couldn’t Stern, Simmons, and Carolla start an entertainment website next year with streaming shows, podcasts, sports columns, etc and charge users $2 a month for access? They couldn’t get 500K – 1 million subscribers? New media, baby!

The Future of Media – Howard Stern, Bill Simmons, Adam Carolla