Entertainment Freelancers and the Entrepreneurial Mindset

Timothy Cubbison
Horseless Cowboy
Published in
3 min readNov 14, 2017

“I am just a freelancer, not an entrepreneur.” This mindset permeates throughout Hollywood’s creative community but is outdated and dangerous. Regardless of how an individual is hired (i.e., employee or contractor), I would argue that the vast number of creative contributors in the entertainment industry should look at themselves as entrepreneurs. The way that they get jobs, build their reputation, and succeed has more in common with a plumber than it does with an employee at a large firm.

While the tech titans of Silicon Valley are our most visible representations of entrepreneurs, they don’t have a monopoly on the term. At its most basic, the term entrepreneur applies to anyone that organizes and runs a new business. In the freelance economy, this can easily apply to the vast majority of folks that are “Self-Employed.” Self-employed Americans accounted for 14.6 million jobs in 2014, or 10% of the national workforce, according to a Pew Research Center analysis of data from the U.S. Census Bureau.

These numbers should come as no a surprise because if we look at American history, it is a full of entrepreneurs, whether they would recognize the term or not. The original colonists of Jamestown were entrepreneurs selling their crops to a company in England. The frontiersmen and fur trappers, the homesteaders and shop owners, they were all self-employed and responsible for their own success. Likewise, the actors, directors, writers, costume designers, cinematographers, game designers, sound recordists, etc. that help create the world’s entertainment, are entrepreneurs. In fact, 17.9% of Los Angeles’ population reports self-employment income. So, I would argue that this center of global entertainment boasts more entrepreneurs than anywhere else in the country.

Adopting the entrepreneurial mindset is beneficial to freelancers because it frees them from restricting labels and allows them to confront the challenges of a changing marketplace. Instead of being a TV writer that waits around for a call from his agent, a writer can seek or create a broader range of opportunities that benefit from his particular skillset. The world of video game writing, technical writing, copy-writing, comic book writing, speech writing, etc. opens up when the writer stops defining himself by an employee label attached to a platform-specific job.

Obviously, an entertainment freelancer and the obstacles that he faces are quite different from other firms, so it is important to define the varying degrees of entrepreneurship and allow the individual to decide which level best applies to him. Accordingly, Professor James Undercofler of Purchase College/SUNY set forth the “Zones of Definition” of Arts Entrepreneurship as follows:

  • Zone 1.a — Personal Entrepreneurship
  • Zone 1.b — Adding Brand to Zone 1.a
  • Zone 2.a — Making a Career for Oneself
  • Zone 2.b — Creating a New, but Recognizable Not-for-Profit Entity
  • Zone 3.a — Create a Recognizable, but New Not-for-Profit Entity with a dual Social and Artistic Purpose
  • Zone 3.b — Create a Recognizable, but New Not-for-Profit Entity with a Social Purpose
  • Zone 4.a — Create a Totally new Not-for-Profit Entity
  • Zone 4.b — Create a Totally New Commercial Entity

I think that most entertainment freelancers fall into Zones 1.a, 1.b and 2.a, so I’ll dedicate my next article to examining them in more detail. I’ll also touch on my addition of Zone 5, which is simply to Create a New, but Recognizable Commercial Entity. One doesn’t always have to reinvent the wheel. As the author, J. Frank Dobie proclaimed, “the story belongs to whoever tells it best.” If your skills allow you to provide a service better than an existing firm, then don’t hesitate to go for it!

Timothy Cubbison is the General Manager of Horseless Cowboy, a creative consultancy that helps bridge the gap between technology and entertainment. His credits include the casting, writing, performance capture and VO production of over 1 million lines of dialogue on 50+ video game and virtual reality titles.

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Timothy Cubbison
Horseless Cowboy

General Manager of Horseless Cowboy | Creative Producer @ the Intersection of Technology and Entertainment