Bill Simmons: The Individual & The Entity

This was originally written the day ESPN publicly announced they would not be renewing Bill Simmons’ contract.

When it comes to writing, Bill Simmons is one of the best at his craft. His ability to weave in and out of pop-culture, sports, and common fan dialects is unparalleled on the internet. This is what catapulted him into the budding star he was when ESPN offered to build a site around him in Grantland.

Simmons parlayed a weekly column into Grantland, and grew his personal brand and the Grantland brand from a website about sports and pop culture to a full fledged media entity. He rolled out multiple podcasts across many verticals (BS Report, Sports, Pop Culture, and even the restaurant/food industry), launched an Emmy-winning documentary series (30 for 30), and most recently a weekly TV show on ESPN (the Grantland Basketball Hour). What other entity could he have done this with except for The Worldwide Leader in Sports?

While Simmons is the face of Grantland, the all-star talent that could be afforded only due to the deep ESPN pockets is what grew the site to something bigger than sports and subsequently drove Simmons’ ascent as ESPN’s golden boy.

Chuck Klosterman is well…Chuck Klosterman. Zach Lowe has become one of the most well-respected basketball writers in the world, Andy Greenwald, Chris Ryan, and Molly Lambert are the new-wave of voices on pop culture, Rembert Browne was 1 of 4 writers chosen to ride on Air Force One to Selma, AL with President Obama, and the list goes on.

With all of this support, capital, and a backer in ESPN which allowed Grantland to develop without a focus on profits, even 3 years in, Simmons was complaining about lack of resources.

With all of this success, Simmons now has plenty of leverage to leave his restricting bosses at ESPN and get paid handsomely for it. But despite this, it will take a platform with reach across different mediums (organic web traffic, podcasts, video, maybe even TV still) for his multi-pronged content approach to maintain its current following. And I’m not sure there are better platforms than ESPN for Simmons.

Why does this matter when individuals have proven plenty able to garner a massive following, distribute content, and generate revenue outside of supporting platforms? Because Bill Simmons no longer views himself as an individual, he is an entity. And if Simmons wants to build the type of entity where he can cross between the worlds of sports, filmmaking, pop culture, and even get called in as a producer to a Summer Disney movie, there are few places he could land with that type of “synergy”.

So while Bill Simmons as an entity has broken up with ESPN, I wouldn’t be surprised to see the fire rekindled in the future.