Bill Simmons is most well known as one of the creators behind ESPN’s 30 for 30, but is also recognized for his successful column, “The Boston Sports Guy,” and his contributions to ESPN The Magazine. Gus Ramsey, program director for Full Sail’s Dan Patrick School of Sportscasting, led a discussion with Simmons, and the two addressed how much the media has changed since they first started at ESPN, and how exploring new mediums can pay off.

Know What Value You Can Bring To the Table

When Simmons accepted the opportunity to start the BostonSportsGuy.com website, it was during a time when people profoundly distrusted the internet and opted for newspapers or watching ESPN. Not only was news slow at the time, but Simmons claims that everything reported was somewhat dull and appeared negative. “It seemed like there was a window for someone in their 20s to reach out to other people in their 20s, so that’s what I really focused on.” When BostonSportsGuy.com was born, Simmons didn’t have the means for access to press interviews or games, but what he did have was the perspective to write like someone talking about sports to a friend. Simmons’ fan-based approach started with 100 email subscribers and grew to over 10,000 readers a day on his website in the '90s.

Eventually, ESPN took notice of Simmons’ work and hired him to write columns for their magazine, and start up their website. Simmons tells students, “When you can only do one thing it makes you less valuable. People that are valuable to us can do three or four things, or can turn things on the fly.”

Don’t Be Afraid to Go Against the Grain

Not only did Simmons adapt to writing for new mediums, but he also recognized all forms of criticism that came with the change. Now, with the integration of social media, the role that readers play has shifted, and Simmons believes, “Twitter is probably the worst thing that has happened to writing. If you make a mistake [...] or you write something dumb, it's like a mob comes after you.” Simmons’ columns were written to spark a reaction and get people talking.

Although his style was known for pushing the envelope from a fan’s perspective, it was common for him to receive pushback for not facing the people he would write about. Regardless of what people have to say about him, Simmons embraces criticism as a sign that he is resonating with his audience and notes, “If you are getting a reaction, but you are putting thought into what you wrote, that’s where you want to be.” As an important takeaway for students, Ramsey and Simmons agreed that it is nearly impossible to have a 100% approval rating in whatever degree of work you choose.

Be Thinking About What’s Next

Simmons is constantly thinking about how he can grow and evolve. In addition to his extensive column work, Simmons also released two books. As Simmons' writing became more experimental and ESPN’s 30 for 30 was successful, he decided he needed to challenge himself further by starting his own company. And, in keeping up with the evolution of media, he also discovered an interest in podcasts. Simmons explains, “I never wanted to keep doing the same thing for too long because I feel like at some point you can’t win [...]. It doesn’t really matter to people because you are always as good as the last year.” Although he didn’t know what he was doing at first, he kept practicing interviewing and within two years was a pro. The podcast started with his friends and connections from ESPN recording out of his home studio. Now, he says, “I’ve done so many of these at this point, you could drop me from a burning building and give me a headset and give me some random actor, and I can go.”

Click here to watch the full interview with Bill Simmons.
Click here to learn more about the Dan Patrick School of Sportscasting at Full Sail University.