Interview: Cheryl Houser talks Generation Startup

Generation StartupPremiering at the Melbourne Documentary Film Festival, Generation Startup is a timely film about a group of young Americans who’ve elected to take the leap and start their own businesses, having recently graduated from Venture for America, an entrepreneurial programme. Adding to the intrigue is the fact that these young people have elected to undertake their task in struggling Detroit, once America’s shining symbol of industrialisation and innovation. They’re just what this city needs, but their choice of location will come with a lot of additional challenges.

Helmed by veteran producer Cheryl Miller Houser and Academy Award winning director Cynthia Wade (Freeheld, 2007), what makes Generation Startup so interesting is its focus on the human costs of building a business. This is not a film about the intricacies of managing cashflow, marketing or business strategy, it’s about what happens when people put themselves on the line in the interest of a vision. This usually means a lot of stress, frustration, sleepless nights, and occasionally a few moments of elation. But it also means that the people we watch during the film will be far stronger and wiser by the time the final credits role.

I had the opportunity to sit down with Cheryl Miller Houser, co-director of Generation Startup, before its premiere at the Melbourne Documentary Film Festival.

Congratulations on Generation Startup – it’s a great story! What’s interesting about you is that, apart from having produced a range of television shows like Biography, Dr. G: Medical Examiner, and David O. Russell’s first film, you’re a business owner in your own right. I’d like to hear a bit more about the challenges you faced in starting up your business.

Cheryl Miller Houser: After university, my career was largely about working as second in command for others and helping other people build their businesses. I didn’t have the courage to launch my own. I got to a stage where I just didn’t want to look back with regret. I wanted to be master of my destiny and tell stories that it inspired me and that I thought would inspire other people. And so I was looking at these kids in this Venture for America programme. My eldest son was in VFA and here they were 22, 23, 24 years old and they were taking big risks at a time when they really didn’t have a lot of experience and I thought that was really inspiring.

So, I launched Creative Breed with the goal of telling the stories that interested me. About four months into launching the company I met Andrew Yang, who founded Venture for America, and said to him “I’m so inspired by what you’re doing and what you’re building and by these fellows and I’d love to follow some of them in one of your cities,” and he was game to give us full editorial control and access.

What I’ve realised is that it shouldn’t have taken me three decades to get up the courage to do this because now that I’ve jumped off the cliff and am running my own company, I realise that yes, it’s a lot of responsibility and it’s scary sometimes, but it’s also so much fun. I really do think that all of us have the power to control our lives more than we think we do.

I guess that leads very well into the next question. What is Generation Startup about?

Generation Startup is about how we all need to move outside of our comfort zone. That’s how we learn, grow and evolve, and how we tap into talents and develop skills that we never knew we had. If you don’t challenge yourself then you’re always going to stay in a kind of stasis. Yes, you stumble or fail sometimes, but it’s through those experiences that you also learn resilience.

You think something’s so scary but then you do it. And then the bar just keeps getting raised higher and higher because as you conquer one fear or you conquer one challenge that you thought you couldn’t do, they get bigger and bigger.

The film is about entrepreneurship and young people building companies. But really, it’s about much more than that because most people aren’t going to launch their own companies, but we can all move outside our comfort zone and do things that are a little scary whether that’s in our personal or professional lives.

Generation Startup

Kate in training at Detroit Labs. Courtesy of Generation Startup

I note that while you’ve produced many films and television shows, this is your directorial debut. What influenced this move into directing?

I think that when one talks about producing or directing, in my career it’s always been a collaborative effort. It’s starts with conceptualising an idea and as a producer I was often one of the engines of those ideas. I mean in the case of David O. Russell’s first film, that was all David, it was his script, his vision, but in the end every movie is a team effort. A lot of what I’ve done as a producer often blurred the lines between producing and directing. In the hundreds of hours of TV I’ve done, I’ve often ended up co-writing scripts or playing a very, very big role in the edit room and shaping and crafting, and even in terms of putting together the teams.

For me whether it’s a 90-minute film, a branded video or a web series, it’s about finding great characters, drawing out the best in them when you’re shooting and then putting it together in a way that has a narrative thread. Even a two-minute piece needs a narrative thread. For me, even though I’d never had a director title before, I think that my entire career I’ve been playing a lot of roles that would fall into the director bucket just like I think that most directors also wear a producer hat.

But I don’t want to offend directors because I think that there is oftentimes a distinct creative vision that a person brings to something, so I don’t want to say that every producer is a director.

And how did you come to co-direct with Cynthia Wade whose film Freeheld won the 2017 Academy Award for Best Documentary Short?

Yeah, Cynthia’s great. When Andrew Yang gave me the go ahead, I started putting together a team and attached Cynthia as a co-director and then together we figured out what was the visual look we were going for, who was the DP we would want to work with, and then had to figure out which city we were going to film in as the VFA run in many cities. We decided that it really should be Detroit for many reasons. Detroit is so visually rich and not so long ago, in the 1950s, it was the fourth largest city in our country and a city that had become magnificent thanks to innovation and entrepreneurship. And it’s the city that had fallen the farthest of all our post-industrial cities – it was in bankruptcy when we started filming. For us, Detroit was a character in of itself.

Cynthia did the lion share of the filming – we went back to Detroit every six weeks for about a week at a time. I was primarily involved with the film through post. But we were very collaborative and I was in the field shooting sometimes and she looked at cuts along the way. With Cynthia, I was so happy to have picked someone who, firstly, has done masterful work and secondly, knew that the point of the movie lay in the stories of people who take big risks, and will struggle, learn and grow a lot no matter what happens.

Here were people who, you know, when you come out of university and you’re 22 years old and out in the world for the first time, you still don’t know who you are as a person. They go from knowing that elementary school leads to middle school to high school to college. This is the first time in their lives when there’s this void. You’re out in the world and no one’s telling you what to do or what your daily structure is.  But here were these kids who were intensifying that void even more, and so Cynthia and I both knew that that would make for interesting stories and for tremendous personal growth, and I knew that we would do a great job in drawing out the humanity in these characters.

Our goal was an emotional journey that would end with uplift and a call to action. It had to be positive, but also put the spotlight on things. The need for greater gender diversity. The need for greater racial diversity, like putting the spotlight on a positive Muslim figure, Labib, at a time when there’s a lot of anti-Muslim sentiment. And then also this whole idea of the disparity of income in this world… for example Labib has no safety net to fall back on if things don’t work out. Cynthia and I were on the same page regarding the stories that we were interested in. That’s why I selected her as a co-director and that’s also why she came on board the project.

You’ve mentioned that entrepreneurship is at a 25-year low among 18 to 30-year-olds in the United States. If I think about all the current conversation around startup culture, that seems quite surprising. Why do you think that is? Did doing the film give you any insights?

I mean, entrepreneurship is down in general, and there are many reasons for that, but in terms of the 18 to 30-year-olds, one reason is they’re coming out with a lot of student debt and if you have student debt you can’t take huge risks. The state of New Hampshire’s doing something innovative. They’re saying that if a graduate launches a company, they’ll pay off their student debt.

But there are different publications that have polled millennials and a lot of it is a fear of failing as well. I think that this is a generation that has had two things happen in the United States. There’s this tremendous pressure to do well, to succeed. You don’t fail. You must succeed because you must go to a good school. To get into a good school, you can’t fail. You can’t fail at anything. You must be the best.

And then secondly, I think they’re very coddled, so if you have a generation that’s been coddled and very dependent on their parents and also been told they shouldn’t fail, I think that that’s like this cocktail that leads to a generation that’s not very big on risk taking. A lot of these polls have shown that in terms of identity they see themselves as entrepreneurial, but they’re risk averse.

Generation Startup

Labib mapping Mason’s strategy. Courtesy of Generation Startup

Is this a film for people interested in startups, or is Generation Startup bigger than that? What do you hope people take from it?

What’s interesting is that the film’s emotional appeal really does make it engaging for people who aren’t thinking about entrepreneurship. But our whole distribution strategy has been entrepreneurial, so it has been licenced by a lot of companies, venture capital firms, non-profits and shown around the country at hundreds of event screenings and oftentimes bringing together entrepreneurial communities or startup communities. We’ve done a lot of screenings at co-working spaces which are kind of like this group therapy for entrepreneurs who often say “Oh, my God. It’s given me renewed inspiration or renewed determination to stick with my startup,” because startup founders always have to put on the brave face, and they have to tell their investors everything’s great and their family that everything’s great and their staff that everything’s great and it’s not great. It’s really hard!

And that, I think, is one of the strengths of the movie because we were with these young people for a year and a half, and we chose well, people who would be vulnerable and let us in.

I think a lot of entrepreneurs feel very isolated and they feel like the problems they’re going through are just them and what’s wrong with them. They keep pivoting and they can’t figure out their business plan or they can’t figure out how to scale. I think it’s gratifying for them to see a film like this and think “Wow. What I’m going through is normal.” I think that most entrepreneurs who succeed, it’s the ones who have the grit and the resilience and the determination and they don’t give up. I think that’s true with film makers also. It’s so hard to get a movie made.

I mean, the movies that get made, it’s because there’s somebody who’s so tenacious and they believe in the project and they don’t give up. I do think that there are times when you must be realistic and say, with a company or with a movie “Hey, this is something that’s not going to find an audience,” or this is something that’s not going to find a funder or a customer base. But I think a lot of people throw in the towel not for the valid reasons that I just stated, but because it just gets too hard.

We followed people who, stuck with it even though it got really hard. Take Labib, his road is hard but you really feel like he has grown so much as a person by the end of the movie. He’s going to make it because he’s resilient.

Dextina rides her bike through Detroit. Courtesy of Generation Startup

Dextina rides her bike through Detroit. Courtesy of Generation Startup

What did he and all the other people that you followed think of the film?

I went to Detroit when the film was finished and screened it for the first time publicly, and they all feel that we were very true to them and that we were honest in our portrayals of them.

Labib sent Cynthia and I such a beautiful email thanking us, and it was titled On Voice in America. It made me cry… he talked about how today when Muslims have no voice, thanking us for giving him a voice, and for letting him share his story with the world. For me what’s been moving and remarkable is to see how powerful this film is for people. As a filmmaker… well that’s why we make movies.

What’s next for you?

When I was in Chile with the State Department with Generation Startup, I learned about a coding school in which the founder takes young women 18 to 30 who don’t have formal education and puts them through a six-month boot camp to learn to code. She has an 80 percent success rate with her students which is mind blowing. I am so excited about what she’s doing with young women in Chile, Mexico and Peru, so I would love to follow a cohort of those girls for six months.

And I’m really interested in the whole area of gender and racial diversity in the tech world. I think it’s really important, so we’re developing several projects that have to do with looking at super positive role models in that world, but also stories that can get at the heart of what can we be doing as a society.

I love this startup space. I love entrepreneurs because they tend to be risk takers, visionaries, people who are willing to work really hard for something they believe in. I definitely want to keep telling their stories.

Tickets to see Generation Startup at the Melbourne Documentary Film Festival are now available.

James Curnow is an obsessive cinephile and the owner and head editor of CURNBLOG. His work as a film journalist has been published in a range of print and digital publications, including The Guardian, Broadsheet and Screening the Past. James is currently working through a PhD in Film Studies, focused primarily on issues of historical representation in Contemporary Hollywood cinema.

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