Weiss attended Woodmere Academy with Doug Ellin, creator of the HBO series Entourage, and wrote for the show. He wrote (or co-wrote) episodes including “Aquamansion”, “The Bat Mitzvah” and “The Sundance Kids”.
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.