Bill Simmons

At 55 years old, Bill Simmons has this physical status:

For eight years following grad school, Simmons lived in Charlestown working various jobs before eventually landing a job at ESPN. The September after grad school, Simmons started working at the Boston Herald as a high school sports reporter and editorial assistant, mainly "answering phones... organizing food runs, [and] working on the Sunday football scores section." Three years later he got a job as a freelancer for Boston Phoenix but was broke within three months and started bartending. In 1997, unable to get a newspaper job, Simmons "badgered" Digital City Boston of AOL into giving him a column, and he started the web site BostonSportsGuy.com while working as a bartender and waiter at night. He decided to call his column "Sports Guy" since the site had a "Movie Guy."

Originally the column was only available on AOL, and Simmons forwarded the column to his friends. He began receiving e-mails from people asking if they could be put on his mailing list. For the first 18 months, Simmons would send it to about 100 people, until it became available on the web in November 1998. The website quickly built up a reputation as many of Simmons' friends from high school and college were e-mailing it to each other. In 2001, his website averaged 10,000 readers and 45,000 hits per day.

In the summer of 2002, Jimmy Kimmel had been trying to get Simmons to write for his new late-night talk show, Jimmy Kimmel Live! which was to premiere after the Super Bowl. Simmons refused for most of the summer because he did not want to cut back on his columns and move to the West Coast away from his family and Boston teams. Kimmel kept on "badgering" him and by mid-September Kimmel had him "on the ropes." It was crucial for Simmons that he could write for the show and on ESPN.com and in ESPN The Magazine, which was possible because of the Disney connection with ESPN and ABC. He has also stated that he joined the show because he was burned out from his column, felt he needed a change, and always wanted to write for a talk show.

Simmons left Boston and moved to California on November 16, 2002 and began working in April 2003 as a comedy writer for the show. Simmons called it "the best move I ever made" and said it was one of the best experiences of his life. He left the show in the spring of 2004 after a year and a half of writing for the show. He wanted to focus full-time on his column, since his writing was starting to slip and he did not have enough time to work on columns or even think about them. Simmons remained in California.

Simmons gained fame as "The Boston Sports Guy" which earned him a job offer from ESPN in 2001 to write three guest columns. His second column was "Is Clemens the Antichrist?" which became one of the most e-mailed articles on the site that year. Becoming one of the most popular columnists on the site, Simmons was given his own section of ESPN.com's Page 2, which helped both himself and Page 2 gain widespread popularity. In the first sixteen months which Simmons wrote for Page 2 the viewership doubled. In late 2004 ESPN launched an online cartoon based on his columns which Simmons later called a "debacle" and decided to stop. Simmons wrote a column per month for his page titled "Sports Guy's World."

As a lead columnist, Simmons was one of the country's most widely read sports writers and is considered a pioneer of sportswriting on the Internet. His readership grew steadily over the following years. In 2005, according to ESPN, Simmons' column averaged 500,000 unique visitors a month. According to comScore, Simmons' column had averaged 1.4 million pageviews and 460,000 unique visitors a month between June and November 2009.

In 2007, Simmons and Connor Schell conceived the idea for 30 for 30, a series of 30 documentaries commemorating the 30th year of the "ESPN era." Simmons and Schell took special interest to "stories that resonated at the time but were eventually forgotten for whatever reason." The series premiered on October 6, 2009, with "King's Ransom" directed by Peter Berg. Simmons served as executive producer on the project until he left ESPN in 2015.

On May 8, 2007, Simmons began a podcast for ESPN.com called Eye of the Sportsguy. On June 14, 2007, the podcast was changed to The B.S. Report with a new theme song written by Ronald Jenkees. Simmons created one or two hourlong podcasts a week, generally carrying one theme throughout, talking to everyone from sports and media notables to his friends. The B.S. Report was regularly the most downloaded podcast on ESPN.com averaging 2 million downloads a month. In 2009, The B.S. Report was downloaded more than 25.4 million times.

Simmons began writing a bi-weekly 800-word column for ESPN The Magazine in 2002 but convinced ESPN after three years to give him 1,200 words. On July 27, 2009, Simmons announced his retirement from the magazine but continued to write for the Page 2 website.

In October 2007, it was announced that Simmons joined the television series E:60 as a special contributor. In May 2010, it was reported that Simmons and ESPN came to an agreement on a new contract, although no official announcement was made on the terms.

Since 2009, Simmons has also been a moderator and panelist at the annual MIT Sloan Sports Analytics Conference Starting in the 2012-2013 NBA season, Simmons joined the NBA Countdown pregame show as a panelist/contributor during ESPN/ABC's coverage of the NBA. He left the show prior to the 2014–2015 season.

ESPN announced on May 8, 2015, that Simmons' contract, which was due to expire in September 2015, would not be renewed.

Simmons served as the editor-in-chief of Grantland, a website owned by ESPN covering sports and pop culture that launched on June 8, 2011. The website's name was a reference to deceased sportswriter Grantland Rice, though it was reportedly not Simmons' choice for the name. Sports blog Deadspin had previously reported in 2010 that Simmons was working on a "top secret editorial project." Some key contributors to the website included Jalen Rose, Zach Lowe, Kirk Goldsberry and Wesley Morris. In August 2014, ESPN announced that Simmons would be leaving NBA Countdown in order to produce an 18 episode primetime show for ESPN through his site called The Grantland Basketball Show-later changed to The Grantland Basketball Hour-which would debut on October 21, 2014. In these episodes, Simmons discussed NBA-related current events as well as some of his more popular sports columns with his co-host Jalen Rose. Special guests included fellow journalists, pop culture celebrities, as well as current and former coaches and athletes. Months after it decided not to renew its contract with Simmons, ESPN shut down the Grantland website on October 30, 2015.

On July 22, 2015, Simmons announced he had signed a new multi-platform deal with HBO starting in October 2015. As part of this deal, he would host a weekly talk show, Any Given Wednesday. The show premiered on June 22, 2016. It was cancelled in November 2016. Simmons's multimedia deal with the network continued, and he announced there were plans for future projects at HBO. A documentary on André the Giant was co-produced by HBO Sports, the WWE and the Bill Simmons Media Group, with Jason Hehir directing. The documentary aired on HBO on April 10, 2018.

In late July 2018 it was revealed that HBO decided to renew Simmons's contract to remain with the network moving forward.

Simmons announced the launch of his new website, The Ringer, on February 17, 2016. The site was to be run as part of his venture, the Bill Simmons Media Group, that was launched in the fall of 2015. The media group includes several podcasts focusing on different aspects of sports, pop culture, and technology today, and features writers on The Ringer website as hosts of these podcasts. The website also hired a number of staffers who formerly worked with Simmons at Grantland. The Ringer went live on June 1, 2016.

On May 30, 2017, Vox Media announced that it had entered into a deal to provide advertising sales and access to its publishing platform as part of a revenue sharing agreement. Simmons retained editorial control of the website. On February 5, 2020, Simmons announced that Spotify was buying The Ringer for approximately $200 million, with Daniel Ek describing The Ringer as "the new ESPN." Simmons stated that The Ringer will maintain content and editorial independence.

At The Ringer, Simmons serves as CEO, writing less than during his previous endeavors. He hosts The Bill Simmons Podcast which regularly rotates through conversations and interviews with Hollywood personalities, professional athletes, other media pundits, old friends, and family. Regulars include his college roommate Joe House, Sal Iacono, Ryen Russillo, Chuck Klosterman, David Chang, and Simmons' father.

In June 2020, Simmons received criticism for the lack of racial diversity in The Ringer following email comments he made to The New York Times, particularly that: "It's a business. This isn't Open Mic Night." Critics noted that Simmons employed his nephew as a producer and had created a podcast for his teenage daughter.

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