25 Films and Shows About the Entrepreneur


Film has a long history of romancing the lifestyle of the entrepreneur and symbolically linking them to the American dream. Whether the narrative follows a businessman, a boxer, or just someone with nothing left to lose, this figure is always depicted as a person who will risk everything in pursuit of an ideal or idea. Here are 25 shows and films that tackle this theme: 


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1) Start-Ups: Silicon Valley: A reality television show about entrepreneurs is a humorous concept. One can only imagine the viewing thrills to be had from watching someone sit for hours at a computer and only move to raise a cup of coffee, argue with their co-founder about business expenses or who will be in charge of the taxes, or attend endless networking events where they give out their name and an elevator pitch on their business so many times you feel like you’re watching Groundhog Day. Point being that reality television is probably the worst vehicle for exploring entrepreneurship because the moments of true breakthrough are outnumbered ten to one by the moments of tedium and repetition. That being said, we all need a guilty pleasure, and Start-Ups: Silicon Valley is sure to give you some laughs…that it was not intending. It was cancelled after one season.

2) Shark Tank: Entrepreneurs pitch their product to a panel of sassy investors for the opportunity to gain financing.

3) America’s Next Great Restaurant: Would-be restaurateurs serve up their ideas to a panel of judges who offer the winner financial backing.

4) TechStars The Founders: A web series created by startup accelerator TechStars that chronicles companies going through the Boulder program. If you’re looking for a dose of reality free of spray tan this is probably your best bet.

5) How I Made My Millions: Successful businessmen and women tell their stories.

6) The Rise to the Top: A web series for mediapreneurs: individuals who have a “platform online, like a web show, podcast, blog, video blog (or some combination thereof) and leverage it to help people and make money.

7) Startup Junkies: A web series that follows entrepreneur Ron Wiener as he tries to build Earth Class Mail, an online postal mail service.


8) Startup.com: A film that chronicles the rise and fall of e-commerce website govWorks just before the dot-com crash.

9) Riot On! Documentary on Riot Entertainment, a 2000-era mobile game company that secured large investments and then abruptly went bankrupt.

10) The Call of the Entrepreneur: The stories of three men from very different backgrounds risking it all.

11) Beer Wars: A tale of small craft breweries trying to penetrate the saturated brew market.

12) Steve Jobs – One Last Thing: A PBS profile on the famed former Apple CEO.

13) We Live In Public: A documentary on Josh Harris, the dot-com millionaire who founded Pseudo.com and tested the effects of media and technology on identity. One of his experiments involved filming his life for six months and broadcasting it on the Internet, which resulted in him having a mental breakdown.

14) Indie Game the Movie: A documentary chronicling the lives of indie game developers, including the makers of the well-known games Super Meat Boy, Braid and Fez.

15) The Startup Kids: Documentary on entrepreneurs in the U.S. and Europe, including the founders of Dropbox and Vimeo.

16) Triumph of the Nerds: The Rise of the Accidental Empire: A documentary on the rise of the home computer, in three parts.


17) Pirates of Silicon Valley: A made for TV movie about the rivalry between Apple and Microsoft in the race for the personal home computer. Not a highly rated film, but Anthony Michael Hall of the Breakfast Club takes a turn as Bill Gates, which could be well worth watching.

18) The Social Network: On the making of Facebook, Hollywood-style.

19) Citizen Kane: The Orson Welles classic, based on the life of the newspaper magnate William Randolph Hearst. An excellent film for exploring what one must give up in the pursuit of success.

20) Ed Wood: Could there be a better example of the entrepreneurial spirit than Ed Wood, cult filmmaker who didn’t let the terrible reviews of his films stop him from making more.

21) Risky Business: A risqué example of supply and demand and the film that made Tom Cruise’s career.

22) Flash of Genius: Biographical film on the inventor of the intermittent windshield wiper, and his legal battle with the Ford Motor Company when they developed a wiper that was based on his patented ideas.

23) Jerry Maguire: A sports agent starts his own company when he’s fired for expressing his opinion.

24) Baby Boom: Diane Keaton portrays a Manhattan career woman who inherits a baby and leaves her hectic life behind to become a baby-food entrepreneur.

25) Rocky: Entrepreneurs are often compared to fighters, and none are more symbolic of the entrepreneurial spirit than Rocky, who gets back up after every blow.

About the author: Caitlin L. Conner

Caitlin L. Conner is an experienced project manager with roots in the games industry. She’s earned credits in production management, game design and quality assurance testing for ten published titles spanning the casual and MMORPG genres.

At AlleyWatch, Caitlin focuses on editorial content, writer coordination, and time and resource management. She also contributes writing on gaming and women in tech.

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