Great Movies you Never Knew Were About Entrepreneurs

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Over the years I have stumbled on some documentary movies that were not overtly about entrepreneurs, but turn out to be. They are various portraits of people who have managed to channel their obsession to accomplish great things. 

  • Man on Wire. this movie is about a French tightrope walker who decided at a young age that he was going to walk on a tightrope between the twin towers in NYC knowing that he would never be given permission. The movie chronicles the multi-year preparation of the mission, including recruiting a team to implement his crazy idea. Want to know the qualities of a good entrepreneur? Watch this movie.
  • Joan Rivers: A Piece of Work. This movie made me realize that Joan Rivers is a true entrepreneur. She has worked harder in her 80s than most people work over their whole career. You also get the sense of her complete devotion to her craft. 
  • Bill Cunningham New York. For more than 45 years, Bill Cunningham has been taking pictures of the fashion worn by people in the streets of NYC. Bill is so deeply devoted to his pursuit, it is at the expense of almost everything else in his life. 
  • Dark Days. Think your startup is resource constrained? Think you are resourceful? Watch how homeless people survive by building a shanty city in abandoned train tunnels underneath New York. 
  • Exporting Raymond. The founder of “Everyone Loves Raymond” works on a project to adapt the show to a Russian audience. A true exploration of what it means to “understand your customer”.
  • Can Mr. Smith Get to Washington Anymore?: About an underfunded political hopeful who runs for US congress. It is a lesson about how grassroots and clever marketing schemes can beat a better-funded incumbant. Play to your strengths and your opponet’s weaknesses. You must beleive in yourself and the mission. 
  • Into the Wind. An amputee decides to run across the entire country of Canada. A great example of the power of human determination and how to turn the many people who will doubt you.
  • Indie Game: the Movie. About a collection of solo software developers writing computer games as labors of love. The amount of sacrifice and time required to get to a success is staggering, and the mental fortitude required to endure the journey is remarkable. 
  • The Island President. The president of the tiny island nation of Maldives fights powerful countries to do something about climate change which is swallowing the shores of his country. The lesson? do not let your company’s size or resources determine its trajectory. If the problem you are solving is an important one, you can’t give up. 
  • Word Wars. About the top Scrabble players in the US. Similiar to Bill Cunningham New York– to be the best Scrabble players, they had to dedicate themselves fully, and unfortunately, at the expense of other aspects of their lives. 
  • Running the Sahara. Three dudes decide to run across the continent of Africa. That’s not a typo. 100 straight days of a marathon+ each day. Also parallels the typical startup story where hired team members don’t exhibit the same blind passion as founders and how that can cause intense friction. 
Let me know what else I missed in the comments. 
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  • William K. Lee

    Jason, thanks for a great post. After reading about these documentaries, another one came to mind: THE FOG OF WAR by Errol Morris. In this film former Defense Secretary and architect of the Vietnam War Robert McNamara reflects on some lessons gleaned from wartime. Two seem especially pertinent to entrepreneurs:

    1) Get the Data. The American administration and military leaders fell down the rabbit hole in Vietnam because they didn’t seek evidence to disconfirm their flimsy assumptions.
    2) Be Prepared to Re-Examine Your Reasoning. The US was reluctant to abandon its strategies because it meant admitting that thousands of lives and billions of dollars were spent in vain. Sometimes founders have to cut their losses and pivot.

  • jheltzer

    Excellent comment Will. I saw that one too but didn’t think about it the way that you did.

  • FYI Sight & Sound magazine published the 50 Greatest Documentaries of All Time. http://www.bfi.org.uk/sight-sound-magazine/greatest-docs

    • jheltzer

      ooh ooh, great list. Not a lot of overlap with my list of docs…going to have to add many of these to the queue. Thanks Will!

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