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Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries” where we ask interesting people to open up about the role money has played in their lives.

In 2007, I’d just finished my third feature, entitled Prince of Broadway. It was about an immigrant from Ghana selling knockoff purses and sneakers on the streets of Manhattan. It cost $46,000 to make, and I financed the movie out of my own pocket. I decided to make a pretty risky gamble. I put all the money I had — around $100,000 — into the release of this film. I decided to pay the costs for the release. We got my film in to some very prestigious theatres around the U.S. including the Angelika Film Center in New York City. A lot of money went to advertising, too. A New York Times ad alone can cost thousands. It felt crazy to drop that much of my own money into it, but I believed in the film (which had done well on the festival circuit) and wanted to invest in my own work. I was certain I’d make some money back.

But I was dead wrong.

Prince of Broadway bombed in theatres. I put $100,000 into its release, and made $28,000 in return. One of the worst investments of all time. It was a real low point. I started smoking cigarettes again. I was like, “Shit, I can’t believe it. After all this time and effort, where am I?” I was literally nowhere, having just spent all my money, without a dollar left in savings. I thought that was the end of my filmmaking career. But in some ways, it was actually just the beginning. Even if you lose money putting a film in theatres, there can be value in having your work widely seen. Critics write about it; a movie becomes eligible for certain awards; industry decision-makers get exposed to your films and see what you’re capable of. While Prince of Broadway hadn’t done well commercially, the reviews were great. Plus, we had a Spirit Award nomination. Suddenly, people offered to finance my next film, Starlet, for $250,000.

* * * *

I fell in love with film at a very early age, growing up in New Jersey. My mother brought me to a series at the local library where they were showing clips from the Universal Monster films like James Whale’s Frankenstein. Soon, I discovered Star Wars and Close Encounters of the Third Kind. In high school, it was RoboCop and Die Hard. I didn’t understand the way that the studio system worked but dreamed that one day I’d make blockbuster films of my own.

At the tail end of high school and beginning of my four years at NYU, I was gravitating toward independent films — the work of Spike Lee, Jim Jarmusch, Richard Linklater, and Steven Soderbergh. Just being in NYC was a film education on its own. I’d go to MoMA, Lincoln Center, Anthology Film Archives, and all these great New York art theatres that played the best of world cinema and independent film, and I started falling in love with movies that leaned more on human stories than special effects. By the time I graduated NYU, I understood that I couldn’t afford to go out and make an action blockbuster like Die Hard as my first film. And creatively, my love for independent movies was leading me someplace different.

So, I took all the money I’d saved from my job as the audio/video producer at a publishing company, plus a bit more I’d earned making a couple of commercials, and at age 25 made my first feature film. It’s called Four Letter Words, and it’s a personal story about young men in suburbia, USA. We shot on 35mm film, and most of our $50,000 budget was spent just buying the film stock. To get the movie made we had to beg, borrow, and steal; I really don’t know how we did it. After a few years, in 2000, the film was accepted into the South-by-Southwest Film Festival. I was like, “Oh my God, I can’t believe it!” It was incredibly validating. Just to have the film programmed at South-by-Southwest meant everything to me.

Four-Letter Words was well-received and even got a small distribution deal, but that didn’t mean I was suddenly rich or that people were coming out of the woodwork to bankroll my next film. Quite honestly, we lost every cent that was invested in Four-Letter Words. But there was still a way forward. In the span of just a few years, the economics of independent filmmaking had undergone a radical shift. The Dogme 95 movement of the late nineties changed things for me. This Danish film movement created by filmmakers Lars von Trier and Thomas Vintenberg began to show that powerful films made on tiny budgets, and even shot on standard definition mini-DV videotape instead of expensive film stock could be accepted by critics and audiences. Now anyone with a camera really could go out and make their own film. So, a fellow filmmaker Shih-Ching Tsou and I made a film for just $3,000, called Take Out, about a Chinese restaurant deliveryman. We had a tiny cast and no crew — our main actor, Charles Chang, helped out as our third crew member. Our only real costs were food, subway fare, hard drives, and blank videotapes.

My hope is that the more stories that are told about marginalized communities and subcultures, the more awareness will spread, and the less marginalized they’ll continue to be.

The movie got into Slamdance and some foreign film festivals. We were thrilled. But we didn’t realize the importance of premiering your film at the biggest festival possible. I’ve learned a lot since then about festival strategy. The smaller festivals don’t attract buyers or distributors; they’re not really a marketplace. Where you premiere your film to a large extent dictates the success of the film. A small distributor picked up Take Out, but did not have the resources to immediately get it out into theatres, and as badly as I wanted people to see the movie, I didn’t know what else to do besides start working on a new movie.

So I just began making Prince of Broadway. When it was finished, and it began to play in festivals, I made a couple of extremely risky financial decisions. The first one was that I paid — again, out of my own pocket — to screen Take Out in prominent theatres around the country. For me, after investing years of work in making Take Out, it seemed worth it to plunk down my own cash just to get the movie seen. And while the financial returns were bleak, critics really responded to the film in the way I’d hoped. We got a 100% rating on Rotten Tomatoes, and I felt new energy around my work. So that gamble, and the one I took on Prince of Broadway paid off, if not exactly in a way I could have predicted.

Because of the critical success of those films, my next one, Starlet, would be the first time I didn’t have to bankroll one of my own films. And the star of Starlet, Dree Hemingway — whose mom is Mariel Hemingway and whose great grandfather was Ernest Hemingway — was interested in acting in my film because her manager had seen Prince of Broadway in the theatre. At the end of the day, my crazy gamble and my investment in myself had weirdly paid off. Starlet premiered at SXSW and was acquired by Music Box Films. The film went on to win a Spirit Award.

But it’s not like everything changed for me. There were still some lean times after Starlet. I wanted to make a movie about the Russian community in Brighton Beach with a $15 million budget, but couldn’t get the funding. I was trying to make The Florida Project for $2.5 million, but again, the financing wasn’t there. I was in my forties, and had to borrow money from my parents for about three months. It was really degrading. I felt really low, but I didn’t know what else to do.

Then I remembered that Mark and Jay Duplass were fans of Prince of Broadway. I reached out to them and they agreed to finance another micro-budget feature called Tangerine, about transgender sex workers in L.A. The budget was so small that we decided to shoot the movie on an iPhone. We premiered at the Sundance Film Festival, where we sold it within days. Magnolia Pictures released the film — which I didn’t have to fund myself this time around! And the movie got an incredible response from audiences and critics, and even won some awards. Nobody was getting rich off of this film — but we did see some money.

I thought having more money would make things easier, but I learned that no matter the budget, you never have enough money.

After Tangerine’s success, I was able to get funding for The Florida Project. The budget was well beyond $2 million, more than 15 times the cost of my previous film. It’s about a hidden populace of impoverished people living in the shadow of Disney World. All of my films seem to deal with people who are economically vulnerable, isolated, ostracized, and marginalized. Some are undocumented immigrants. Some are sex workers. Some are living so deep in poverty that the underground economy is the only way they can survive. Our society is so focused on money, money, money: When you look on Instagram, everybody is always showing off the things they’ve bought. We forget about the people who are exploited through our materialism — whether they’re in L.A., living in Hollywood’s shadows, or in Florida, in the shadow of a gigantic theme park.

My hope is that the more stories that are told about marginalized communities and subcultures, the more awareness will spread, and the less marginalized they’ll continue to be. I’m not a politician or a policymaker, I’m a filmmaker and storyteller. My goal is simply to put a human face on these hidden populations that often aren’t humanized, so that people feel inspired to make a better world. Sometimes shining a light on an issue is the first step toward affecting change.

I thought having more money would make things easier, but I learned that no matter the budget, you never have enough money. Things were very tight, but we were responsible, kept things on-budget, only had one hour of overtime the entire shoot. And I still found ways to make it hard for everybody! I wanted to make a movie with a lot of kids; I wanted to shoot on 35mm film; and I chose to shoot in Orlando in the middle of the summer. Those are three really difficult production challenges. But we’re happy with the results, and excited to finally put the film in front of audiences this week.

As for what comes next, it’s not like I’m being offered Marvel movies, so I don’t know that I’ll leap anytime soon into making the kinds of blockbusters I loved as a kid. These days, I look to model my career on the careers of people like Paul Thomas Anderson, filmmakers with singular visions who’ve been able to make their own films from their own screenplays. And when I think of the last 20 years — all the ups and downs in the creative and commercial process, all the money I risked on my own films — I can say that, at last, I feel a small sense of financial security because opportunities are finally coming my way. Last night, sitting on the couch with my girlfriend, I looked over and said, “You know what? I’m 46-years-old, and I finally, finally, finally have reached the point where I’m not scared about next month’s rent.” And when it comes to personal finances, that’s about the most satisfying feeling anyone can ask for.

As told to Davy Rothbart exclusively for Wealthsimple. Illustration by Jenny Mörtsell. We make smart investing simple and affordable.

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