I remember when I first came across The Sports Guy's writing. It was 1998, and I was a sophomore at MIT. On one of the few-and-far-between breaks from my engineering study sessions, I logged on to The Boston Globe's website to find a good recommendation for a restaurant. Being a sports enthusiast (as well as a sports columnist for MIT's bi-weekly campus newspaper The Tech), my attention drifted to a link in their website's sports section, which was an opinion article in which a local writer roasted his local Boston Celtics for their lackluster and apathetic play. That local writer was Bill Simmons, and his wit, humor, and constant pop culture references kept me reading to the end. Once I wrapped up the article, I shared the link with all my fraternity brothers via e-mail so that they could see how good this guy was at his craft, not to mention how spot-on he was at reaching out to the 18-35 year-old male sports-loving demograph.
Back in these days, the high-speed internet was still in its infancy, and MIT was one of the first universities to have T1 connections in all university buildings, including my fraternity house. Nearly all of the students consumed their news online, and the sources of entertainment to be gained from the internet - music, blogs, video - were growing day-by-day. Simmons - at the time a 20-something beat writer for a handful of little-known Boston publications - was one of the first in his industry to see the value of the internet as a form for exposing his original content to a wider audience. He updated his content weekly and soon gained a large following, first from the Boston area and then from across country. By the time he was offered a job to write for ESPN.com in 2001, he had a worldwide readership, as evidenced by the addresses of readers who would submit e-mails to his popular "Reader Mailbag" column.
Fast-forward to 2012, and Simmons is one of America's most established sports writers. He surpassed 1 million Twitter followers in 2010, and he was recently named the 12th-most influential person in sports - the highest ranking for a person who was not an athlete or front-office figure. In addtion, he has written a New York Times best-selling book and spawned a countless number of imitators of his witty, sarcastic, self-deprecating way with words. His most impressive accomplishment, though, remains Grantland - a digital tour de force of sports and pop culture content that is updated daily by some of the best sports and entertainment writers in each industry. Since coming on to ESPN.com, Simmons has constantly embraced evolving digital media as a futuristic toolkit to enhance his writing. While traditional journalists supplemented their writing with pictures and quotes, The Sports Guy included embedded links, video, and interactive polls in his blogs, which made his writing more engaging, animated, and edgy to his readers than the works of his peers. Grantland is the creative pinnacle of this digital evolution: podcasts, user-generated content, digital TV reviews, insightful observations on technology in sports, cross-link traffic, live open chats and one-on-one writer debates, and other goodies that keep the Gen X, Gen Y, and Millenials procrastinating for hours on end. And the best part??? It's all free to the consumer, with occasional banner ads and segment sponsorships keeping The Sports Guy's All-Star team of content providers fat and happy.
Simmons is 100% self-aware of his rise to prominence due to digital media; in fact, he has made a career of lampooning the "old fuddy duddies" in sportswriting who were slow to change their ways to adapt to emerging technology. My personal prediction is that The Sports Guy, by way of Grantland, will be on top of the game for years to come, and he will always be a regular read for me on account of our humble digital beginnings together in snowy New England.
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