Weiss wrote and directed his first film, Amongst Friends, in 1993. Since that time, he has been nominated for three Primetime Emmys and nine other nominations over the course of his career. With six successful seasons as a writer/producer for Entourage under his belt, Weiss’ latest venture is making headlines: the HBO “dramady” How to Make It in America, which he also writes and produces.

There are some autobiographical undertones in the series, and viewers catch a glimpse of some of Rob’s early struggles growing up in New York. The show, which aired its first episode in February, follows two enterprising friends in their late 20s as they hustle their way through New York City, determined to achieve the American Dream. They strive to make a name for themselves in New York’s competitive fashion industry.

Ben Epstein (Bryan Greenberg) and business partner Cam Calderon (Victor Rasuk) use both their knowledge and their street smarts to bring their ambitions to fruition. Cam’s cousin Rene (Luis Guzman), who is trying to market his own high-energy drink named Rasta Monsta (which he describes as “better than Viagra”), is another colorful character, as is Ben and Cam’s well-connected friend Domingo, played by Kid Cudi. Lake Bell plays Ben’s ex-girlfriend Rachel, who is concentrating on her career and a new boyfriend. Other notable characters are Edie (Rachel’s boss, played by Martha Plimpton), Gingy (Ben and Cam’s artsy friend, played by Shannyn Sossamon), and David Kaplan (Ben’s high school friend who is now a successful hedge fund manager, played by Eddie Kaye Thomas).

While interviewing Weiss and hearing about his days as a student at Parsons, The New School of Design, where he studied both fashion and film, I realized that it is his own hunger, ambition, tenacity, and New York-rooted instincts that provided much of the inspiration for the story lines in How to Make It in America. Weiss’ characterization of the central figures in this program no doubt spring from his own personal journey through the America that he grew up in during the 1980s. You can almost hear an echo of a young Weiss’ voice in the banter of the characters, which is why critics have hailed that How to Make It in America “couldn’t be more genuine—not just a loser’s fantasy of what it’s like to be a player.” Certainly today no one could call Rob Weiss a “loser;” he made the American Dream a reality. But despite all of his successes, he is the type of guy who never feels satisfied. He strives constantly to achieve more everyday. With all of the success he has achieved, he is still approachable and as real as they come.