Herskovitz was born in Philadelphia, Pennsylvania, the son of Frieda (née Schreiber) and Alexander Herskovitz. His family is Jewish. Herskovitz attended Brandeis University, graduating in 1973. He entered the AFI Conservatory in 1975, where he and Edward Zwick first met. He frequently collaborates with Zwick, with whom he runs the film and television production company The Bedford Falls Company, named for the fictional town in the classic film It's a Wonderful Life. Their most recent project is the 2010 film Love & Other Drugs. In 2007 Herskovitz ventured into the world of broadband production with the original series Quarterlife, which debuted on MySpace and a dedicated social network also called "quarterlife". It garnered enough views to be picked up by NBC and aired in 2008, but was quickly canceled.