Making It: The Rob Weiss Way

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.

Haute Living: What character do you identify with on the show and why?

Rob Weiss” I think I identify with every character on the show. And I’m pretty sure if you asked any of my partners, they would say the same thing. There are pieces of us in all of them. In my life, I’ve definitely had Ben’s insecurities, as well as his losses. I definitely identify with Cam’s spirit and his drive, and Luis Guzman’s desire to change himself and strive to do something greater, and being a boss and strong-willed.

HL: What do you believe your audience can learn?

RW: Well, hopefully if we do the denim business right, the audience will be able to start their own jean line after watching 80 to 90 episodes.

Seriously, I think that they will learn about life in New York. It’s a bit of a guide to being successful, a guide to surviving the biggest, probably toughest, but most-loving city in the entire world.

HL: As a native New Yorker who has been living in Hollywood for a long time, what most surprised you about New York City when you were scouting for locations?

RW: Nothing surprised me about New York City, that’s what’s so great about New York, because there are no shockers. You just know that it’s always evolving, always changing. No street ever looks the same way twice. I had no surprises. The city is a major character in the show, and it’s a character that doesn’t negotiate. You are going to take it for what it is. And it will allow you to shoot in it. It’s a living, breathing beast.

HL: How would you compare filming for HBO in New York to filming Entourage in Los Angeles?

RW: I think both situations are extremely similar. We’re capturing the local color and the flavor of the streets on both coasts. Entourage does the best job of anything I have seen shot in Los Angeles, truly uncovering one portion of L.A. life, which is a more polished glossy version of Los Angeles, but it does a phenomenal job of really showing that and exploring that aspect and lifestyle.

Comparatively, in New York City, we cast a wider scope of how to make it in America. There’re highs and lows. We go uptown and downtown. The West Coast show is a tremendous lifestyle showcase. And it is definitely a postcard for why to visit L.A.

HL: How do you perceive that the show will inspire struggling young entrepreneurs to pursue a path to glory?

RW: It’s not a secret that when you profile and model yourself after people who have inspired you, there are valuable lessons you can learn from watching them. There are some great filmmakers, producers, and writers who came before me who I looked up to; even if I don’t know them on a personal level, just knowing their work and their stories helped shape and mold my own personal path and journey.

So I would imagine that if we do the show right and we really do explore the realities of what its like to be an entrepreneur in New York or a hustler in New York—someone who is trying to produce a denim line or distribute an energy drink, or be an interior designer, or an architect, or a hedge-fund trader on Wall Street—anything that we try to explore, hopefully we are going to bring the element of truth to it, and people can learn from it. Maybe people watching the show can see things that they would be interested in doing or not doing. Maybe there are some cautionary tales, and maybe there are some moments of inspiration as well. I think that’s the trick to the show, to make something that’s ground level not so super-wish fulfillment, but is incredibly aspirational. To make the journey look fun, to make the struggle look fun, has always been something we wanted to do with it. We wanted to have the guys struggle and have a good time doing it.

The old adage is, the journey is the destination, and if you look at your life like that, you can’t really ever have a bad time. Despite some massive hardships and set backs you may encounter along the way, you always find your way back.

HL: How did you uncover the authentic New York super spots that are the backdrop for the show?

RW: Research. You go out, you have a good time. You spend your nights eating at Abe & Arthur’s, Avenue, going upstairs at Boom Boom Room and to 1Oak. That was the lifestyle we lived while producing the show. Downtown at Schiller’s, hanging out at The Bowery Hotel. [The show] has a great vibe of New York City. To stay true and keep it real, we actually live this life, so we aren’t a bunch of guys making a show that we don’t live. We do want it to be authentic.

HL: While filming, did you find the energy and people in NYC different from the energy and people in L.A.?

RW: Uh, yeah, there is a tremendous energy difference between NYC and L.A. I love both places, and I am proud to be able to call both cities home—New York being where I am from, and L.A. being where I live. You can’t beat New York City’s energy—the pulse of it, the rhythms of it. California, you can’t beat its calmness, its peace and serenity. There is a tremendous difference between both places and both are equally lovable.

HL: Where do we see the storyline going in the future seasons?

RW: It’s a show about people really striving to find their own version of the American Dream, and they will either find it or they wont.

HL: Why did you select New York City as the venue for the show?

RW: Seattle was not available, and we thought we would be way too hot in Louisiana.

Really, I think there is only one place that is symbolic of the American Dream, the most symbolic city in the whole world. The melting pot, multicultural, stratus from elite to struggling and poverty—maybe it’s not so impoverished anymore, but it is still a representative of everything that’s New York City. It was a very clear decision.

HL: What advice would you give a young producer who is striving to “make it in America”?

RW: You need to really know what you want to make, why you want to make it, and whom you are making it for. If you know those three things and you can really isolate it, then you can probably at least be able to explain it to someone who can help you get it done. Because everybody’s got an idea; people who actually discipline themselves and people who realize the idea, those are few and far between. You got to stick with it, you got to keep evolving, you’ve got to keep learning, and you’ve got to find your own inner voice. Your inner voice should be present in the kinds of projects that you are interested in tackling and developing.

If you are talking about a writer/producer, which is what I am, it’s just a vision. It’s saying ‘I think people would like this, be entertained by this, be interested in this,’ and it’s finding the ideas within yourself that you truly believe in.