In an August 2007 New York Observer interview with Ellin, he confirms that Weiss was the basis for the character of Billy Walsh, a perfectionist filmmaker who was a recurring character on the series. Ellin even asked Weiss if he'd play Walsh, but Weiss declined. Instead, the role went to Rhys Coiro, to whom Weiss bears little outward resemblance.
In 2014 Weiss partnered with Davidoff of Geneva to create the signature cigar line BG Meyer Cigar Co.; its launch was lauded by Cigar Aficionado. Deadline also reported Weiss was tapped by Sonny Barger and Fox 2000 to write and direct the feature film Hells Angels.
Weiss wrote the story and produced the film adaptation of Entourage (2015), and will executive produce the 2015 Dwayne Johnson show, Ballers.