Sherman graduated from New York University in 1985 with a Masters of Science in Counseling. From 1976-1980, he attended Edward R. Murrow High School in Brooklyn, NY.

Sherman has written for many publications, including The Washington Blade, Genre and Instinct. In the September 16, 2002 issue of Newsweek, Sherman's If Our Son Is Happy What Else Matters" was selected for the prestigious "My Turn" column. For the impact of that article, which described a homophobic attack on his family, and other advocacy efforts, Mr.Sherman and his family won the 2004 "Families of Pride" award from the Family Pride Council (later, the Family Equality Council

In June, 2008, Alyson Books published Sherman's first novel, the romantic, humorous mystery First You Fall. First You Fall received positive reviews and was the winner of the 2009 Lambda Literary Award for Best Gay Mystery.

Sherman's first podcast was The Gay Parenting Show, which ran from 2005-2007 on The Podcast Network. The Gay Parenting Show featured personal commentary and interviews with experts in the field of gay parenting, including Dan Savage, author and activist Wayne Besen and Evan Wolfson of the Freedom to Marry Coalition.

Sherman's next podcast, The Digital Photography Show, ran on The Podcast Network from 2006 to 2008. The Digital Photography Show was hosted by Sherman and Michael Stein. The Digital Photography Show was a consistently top-rated show in iTunes and was nominated for two Podcast Awards in both2007 and 2008.

In 2008, Sherman and Stein moved their show to Personal Life Media, where it was renamed Digital Photography Life". Guests on the show have included Scott Kelby, Rick Sammon and Nicholas Boothman.

After an on-again/off-again podcasting schedule, the Digital Photography Life podcast abruptly ended on September 21, 2009 with no explanation for the termination of the show.