How To Make A Million Dollars In Hollywood
York Shackleton, 38, has gone from professional snowboard champion to movie mogul-in-the-works in just 10 years. He recently opened Endurance Pictures, a low budget film production company on Sunset Boulevard in Los Angeles. His business partner is well known in the world of mixed martial arts, former owner of the TapouT brand, Dan Caldwell (who goes by another name to friends: “Punkass”). Caldwell’s millions, coupled with a million or two that York’s been able to string together after a series of successful returns on investment has launched a new career for Caldwell, now that he’s no longer fully involved in his apparel company since selling it to Authentic Brands of Toronto.
If the name Shackleton and Endurance ring a bell, it’s because York is a distant relative to Antarctic explorer Ernest Shackleton, who captained the ship Endurance during a long voyage to the South Pole in 1914.
York considers himself an entrepreneur first, a movie maker second. He’s been turning low budget movies into million dollar profits following these basic steps.
1. Make a Sample Product
In the movie biz, that means making a movie. York’s first product was a documentary called “Las Paraditas”, a movie about prostitution in Mexico. It cost him $14,000. He got the money from Barry Goldwater III, a relative of former presidential candidate Barry Goldwater of the infamous Nixon-era Watergate scandal. He shot it all by himself. And nearly tripled his money when he sold it to a tiny foreign film distributor.
2. Learn The Boring Stuff
Even if it means taking crash courses at extension schools. For movie maker York, “Las Paraditas” led to a showing at Cannes, which led to contact with a man named Leonard Shapiro, a straight-to-video indie movie expert who was teaching at UCLA on the side. He convinced York to take classes at the school and not just to learn the creative stuff like screenwriting and film making, but also the un-glam, non-creative parts of the business, like marketing and distribution where the real money is made.
3. Show Sample Product to Potential Investors & “Door Openers”
And don’t stop. Show them what you can make, even if it means you have to keep making short movies on the cheap. The key here is to have a product with potential. “Las Paraditas” opened doors for York, who was able to work on two other low budget films after convincing individuals he could make a return on their investment. From there, he met Randal Kleiser (Grease, Blue Lagoon) who added to his network of door openers.
4. Secure Distribution
York’s relationship with Shapiro led him to Echo Bridge, a second tier East Coast/West Coast film distribution company. He secured distribution on two low-budget indie films, including his claim to fame: “Kush”, a crime drama about a group of friends caught up in a drug-related kidnapping. Once you can secure distribution, you can more easily convince investors to invest because they know part of the film is already paid for.
5. Start Small, But Make $10,000 Look Like a Million
York doesn’t make million dollar movies. He is playing on the sand lot, not the back lots of Paramount, he says. “Kush” cost him and five partners $100,000 total. It grossed above $3 million. “Roman”, a horror movie, cost just $75,000 and went straight to home video. It made $2.5 million. He recently sold both to The Sundance Channel. His latest, “1 Out of 7″, starring Vivica A. Fox, cost $500,000. Now he’s moving on up as his product returns improve.
“My early investors were just a bunch of film school friends with money in their trust funds,” he said in a phone interview with me last month. “I pitched the idea to them, and they pitched the investment to their parents.”
Trust funds are for beneficiaries only at a certain age. The funds are run by trustees, often times parents, who are in charge of the disbursements.
York and Caldwell’s new Endurance Pictures is currently filming their first studio project, a psychological thriller called “Pretty Perfect” and a love story called “Regret”, due out in 2013 and fully financed by Endurance.
Of course, there’s a disclaimer in all this. What works for one person in a vocation doesn’t work for all. Having a portfolio of work is important, but that portfolio requires lucky encounters with people who can help you achieve your goal.
York is unique, and not only because of his distant connection with the famous British explorer. He made a lot of his money as a champion snowboarder. He also has his own real estate construction business. In short, he is independently wealthy. He also lives in Los Angeles, where the bulk of the movie making business takes place. But that doesn’t take away from his business model: which can be applied to any product line, or service — having something to show, starting small, keeping your costs down and dreaming big.
I become interested in York before I even met York. I lived in an apartment in São Paulo with an Antarctic explorer named Julio Fiadi. I learned about Ernest Shackleton from him. I used to see Fiadi training for his South Pole adventures at the Pacaembu soccer stadium. He’d have about four car tires roped to his waist and he would be walking around the stadium’s parking lot.
Then there were the days leading up to this year’s Superbowl. I read this article in The Boston Globe about how Bill Belichick showed his 2002 New England Patriot team a documentary about Ernest Shackleton’s adventure. It was the coach’s way to show the team what kind of team work he expected from them. They won the Superbowl for the first time in franchise history that year.
A month later, I got an email about York. I gave him a call on a whim. When he spoke about entrepreneurship and teamwork, I figured it was a good fit to put him online here at Forbes, even here on the emerging market pages. Why not? He might be an emerging movie mogul.
