How To Make It In America: Dream Big Or Go Home

If you're a 20-something living in New York, traversing the downtown scene in search of big breaks and big dreams, chances are How to Make It in America is your kind of show. If you're not, the popular HBO series probably makes you wish you were.

How to Make It, created by native New Yorker Ian Edelman, chronicles the journey of two childhood friends from the Lower East Side with skyscraper-sized aspirations -- played by Bryan Greenberg and Victor Rasuk -- who set out to start their own apparel company. The show, which begins its second season on Oct. 2, offers not only a spot-on, gritty-meets-glamorous view of life in the Big Apple, but one of the more realistic portrayals of entrepreneurial life in one of the city's sexiest and storied industries -- fashion.

The first season introduced viewers to Ben Epstein and Cam Calderon and their unlikely friendship that could only be born on the streets of New York. ("We got something for everybody -- tall/short, Jewish/Latin, grumpy/cool," Cam once riffed.) Despite a longtime interest in fashion and design, the closest Ben has come to the "industry" is folding designer jeans at Barneys, while Cam constantly pursues side hustles with a success rate that still has him living with his grandmother. But a visit to a loan shark, a pricey spool of denim and a lucky break from a Japanese buyer set Ben and Cam on their way. Lake Bell, Eddie Kaye Thomas, Scott "Kid Cudi" Mescudi and Luis Guzman serve as a colorful supporting cast both on screen and in the lives of this entrepreneurial duo.

In Season 2, as their Crisp brand begins to mature, so too do the characters, and viewers can expect Ben, Cam and their crew to experience the successes and soul searching that come with a startup -- and make for compelling television.

So where did the real-life inspiration for this fictional entrepreneurial story come from? We recently sat down with Edelman, Greenberg and Rasuk to find out what it takes to really make it in America.

Ian, this is your brainchild. How did the series come about?

Edelman: The genesis of the idea was a two-pronged thing. One, a large part of it was me being born and raised in New York, skateboarding, playing pickup basketball. I just love New York and spent so much of my time on the streets of New York, where so many great stories are told. And two, my parents are first generation immigrants from Eastern Europe. On long road trips, they would always tell us these rags-to-riches stories -- cheese importers and the like. They were just so proud. These are great stories to tell.

I've lived in New York most of my adult life and I think the bar is incredibly high for shows that are set here, because New Yorkers can always spot a fake. What's great about your portrayal is that the city becomes almost another character. What's it like to use this place as your canvas?

Edelman: Hopefully there's kind of a throwback New York spirit that people can connect with. We want young people, young entrepreneurs, to connect with it and feel it reflects their experience. I grew up in Yorkville, which I sometimes call the slums of the Upper East Side -- a very nice middle class neighborhood. I always say it was flavor-free back then. I started skateboarding in sixth grade, so I'd always be downtown and that changed my experience growing up. I sort of had a real-life Cam character in my life. Skateboarding is great, especially in a city like New York, because you'll meet the world.

Rasuk: This is literally where I grew up. Forget that it was just shot in New York, because it could've been shot anywhere in New York, but it was shot in my neighborhood. I find myself always telling either Bryan or someone in the cast, "Here in this building, this happened, 10 years ago in this building, I had my first kiss." So it was cool to be around that. And also, the simple fact that Ian really tried hard -- not tried hard, he made it a purpose -- to make sure that it was portrayed the right way, the exact way how things really go down in New York.

Greenberg: No one's doing what we're doing. No one's showing the world that we're showing, on television and even films. I just don't see it. It's very specific to what people in their late 20s are going through. And it's the only thing that I read that I thought spoke to that voice that's missing. Not only does it capture the hip Lower East Side/East Village crowd, but we go into The Bronx, we go into Harlem, we go into Brooklyn, we go into Staten Island, we're hitting every borough. I feel like the canvas that we're painting on is very vast.

I sometimes describe the show as "Entourage for entrepreneurs, set in New York." Think that's a fair comparison?

Rasuk: I've never heard that before.

Greenberg: That's pretty good.

Feel free to pass that along to your marketing people.

Rasuk: [Laughs]

Greenberg: Obviously, we want to be thought of as our own show and respected for what we're trying to do, because I do feel like what we're doing has an original voice. I get it, the comparisons are inevitable -- we've got Mark Wahlberg and Steve Levinson producing it, we've got guys in their late 20s hanging out, on different coasts, half-hour show, HBO, totally get it. And I'll take it, you know what I mean? Could be worse, to be compared to Sex and the City and Entourage. Those are very successful shows. I think as time goes on, they'll see that we're our own show, our own entity.

Edelman: I would certainly understand that comparison. But I think it's a different experience. And I think Season 2 will provide an even more different experience.

Ian, when you were writing these characters, what entrepreneurial traits did you want to highlight?

Edelman: One, that it's incredibly hard -- it's impossible, it's relentless, there are a lot of small victories. And I think the takeaway is, "Enjoy the process." As cliched as it sounds, it's the journey, not the destination. All of us capitalists are focused on what you have and the show, as much as possible, tries to make it about what happens along the way.

And how did you guys prepare for the roles? Because it's a pretty accurate portrayal of startup life -- the scramble for money, the hustle, the uncertainty.

Rasuk: I remember, before we shot the pilot, I would call Bryan and be like, "Dude, I'm just sitting here, hanging out on Orchard Street, on a stoop, just watching these guys selling. When people walk by, how they would go out and scream. If you remember the first episode, the way I was screaming out to people, "Leather jackets! Leather jackets!" -- that was something I had just seen a few days before. Just little things like that. And again, giving props to Ian, his writing said a lot too. He was open to our ideas and there were a lot of things that we improvised. It was a conversation, it was that kind of work environment.

Bryan, I know your character is sort of based on Ian.

Greenberg: Yeah, I'd say loosely. Style-wise, it's more Ian. It's funny, we'll show up to work and I'm in wardrobe and he's wearing the same thing and I'm like, "Dude, you know what I'm wearing today. You picked it out." But the research I did, I didn't know that much about the fashion world, so I met with some designers, I met with the guys from The Hundreds. I found their story to be very similar to what's going on and reflective of a lot of these street brands. And then Gessner, who started Zoo York, is a consultant on the show and he does all the designs -- New York City Eats Its Young, all the new Crisp stuff that you're going to see Season 2 -- that's Eli. And I talked to some of the guys at Mark Ecko's company. These guys got stories forever. It's fascinating, because you're selling denim or a T-shirt and it's not really that different. It's jeans. Really, how different can jeans be? So what I've learned about fashion, it's really branding. That's what it is. Fashion is branding. You're selling an idea, you're selling a concept, you're selling a lifestyle.

I tell real-life entrepreneurial stories for a living. It's strange to me that you don't see too many portrayals on TV or in film of what I think is just a fascinating human experience -- starting and running a company. Why do you think your show is one of the few?

Edelman: That's a really good question. That's a great question. I have no idea. Off the top of my head, I think it's a brutal process and it's hard to translate that process, to do it justice. It's a lot sexier to be a hotshot lawyer on a TV show. And from a purely TV writer's standpoint, it's not linear -- as an entrepreneur, every day is a new challenge.

Greenberg: Because everyone else is doing cop shows.

Rasuk: [Laughs].

Greenberg: It's very timely. You know, we're not living in the same time as, say, Sex and the City. The Internet was booming, real estate you couldn't go wrong, the towers were still there. This is not that time, man. The towers got wiped out, the housing bubble burst, unemployment kicked in -- and now the career mindset is you have to do a lot of jobs, you have to hustle. And that's what people are going through. They're hustling. And it's not just fashion. This show wouldn't be on the air if it was just fashion people watching it. People love it because it speaks to the American Dream of going against all odds and trying to make something happen, trying to start a business from nothing, scraping by, hustling, lying, cheating, stealing, whatever it takes to get it done.

I have a friend who started a sunglass company a couple years ago -- right in the East Village, very similar experience. Not surprisingly, he loves the show. What do you think is the takeaway for an entrepreneur like him? And viewers in general?

Greenberg: There's so much that I feel like you could take away. If it's strictly on an aesthetic level of fashion or what is hot in music or what is the cool spot in New York to go to -- if that's what you're into the show for, you could get that. But if you're talking bigger themes, my character this season is having an identity crisis. And so when opportunities come your way as a young business, you really have to define who you are and what you want your business to be. And you don't really know those things until those things get put on the table. That's when you decide who you really are. And so Ben has to figure that out. He has to figure out who he is as a man and what he wants Crisp to be. And that changes their dynamic, their friendship.

Rasuk: Especially for people like your friend, I would say the bigger theme would be when the door is shut in your face, you have to keep going. For the boys, I think they're starting to do that -- even after all the times they heard "no" and all the doors they had shut in their face -- I think the theme for me, that I hope people take away, is to keep on being persistent. There's a light at the end of the tunnel.

What do you think are the challenges facing real-life entrepreneurs today?

Edelman: It's evermore crowded, between the Internet and social media and things like Kickstarter -- the tools to reach the public have been democratized. Anyone with an idea and a computer and high-speed Internet connection can take a shot. And that's where it comes back to the determination. Because everyone has the tools now.

This is a story about a friendship and a partnership. Which is fitting, because more and more young entrepreneurs are starting businesses with friends, instead of going it alone. But it can be a tough dynamic. Can we expect this to be a challenge for Ben and Cam as Crisp grows?

Greenberg: Definitely. It's funny, because in the first season, Cam is like the street hustler. I think Cam just likes to hawk the product -- he doesn't even care about what the product is. He's like, "Oh, it's fashion? Alright, we'll do fashion! Whatever it is, let's just do it. Let's hustle." And Ben is the visionary, he actually has a goal of style and what he wants to accomplish. But I think in Season 2, the roles get reversed and Ben becomes a little more business-minded and wants to take Crisp in a different direction than Cam and Cam gets a little more artistic. The company almost falls apart this season.

Rasuk: And so does the friendship.

What else can we expect in Season 2?

Edelman: The stakes go up. I think Season 1 was "beg, steal and borrow," and I think Ben and Cam are back with a little swagger. They're back in New York. People know Crisp. There's a confidence there and a sense of identity.

Rasuk: Sexier, funnier.

Greenberg: Edgier. The slogan this year is "Dream Big or Go Home." And that's what these guys are doing. They're taking their business to a whole other level. And with that comes a lot of problems -- more money, more problems, girls, friendship issues, drama.

The three of you have strong ties to New York. What's your favorite thing to do when you're back?

Edelman: I must've walked almost every block on that island. So when I'm back, I like just walking and just re-entering the streets and energy of New York. You can walk five blocks downtown, run into seven friends, and make eight different plans. I just love getting back into it.

Rasuk: I love going back to Tomkins Square Park. I just love walking around there. I just love the cafes. Café Pick-Me-Up is one of my favorite cafes in New York. So that's one of the first things I do.

Greenberg: I just walk. I walk the streets. I'll walk the whole island, man. I love it. Run into friends. Meet someone here for a drink, then I'll go to dinner with another friend, maybe go see a play. I just love where the city takes me. I don't have to make plans -- it usually just unfolds. If you step out of your house in New York…

Rasuk: It unfolds.