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3 Must-See Movies For Entrepreneurs

Get ready to grab some popcorn and be entertained and inspired with some top entrepreneurial movie picks.

I reached out to several Minnesota venture capitalists, angel investors and founders with the following question: what is your favorite entrepreneurial movie and why? The answers crossed a variety of movie genres from romantic comedy to documentary to musical and spanned decades of movie history. Each choice depicts a unique perspective of the entrepreneurial journey. Happy watching!

The Greatest Showman

This movie came up as a favorite for several investors and entrepreneurs alike. The musical is a theatrical peek behind the scenes of P.T. Barnum’s life as he built the Barnum & Bailey Circus. Throughout the movie, Barnum experiences the highest highs and lowest lows of building a company. It’s insightful for entrepreneurship because it shows how massive ambition, salesmanship, hiring and general business execution ebb and flow with the ups and downs founders feel in their business life and in their personal life.

A recruiting lesson from the movie seems to particularly resonate with. A song in the movie between Barnum (Hugh Jackman) and Phillip Carlyle (Zac Efron) called “The Other Side” is like a mini masterclass in influencing someone to join a young startup team. Barnum’s persistence is apparent as he paints a picture for his recruit of the better life that would unfold by taking the position. Ultimately, the two men negotiate and close the deal, representing a turning point in Barnum’s company.

You’ve Got Mail

Reaching way back in the movie archives is a classic story of a big box store coming into town and squeezing the local shop out of business. The viewer is taken on a journey watching Meg Ryan, the owner of a charming specialty children’s bookstore, lose market traction and eventually shut down her business in the face of a large bookstore conglomerate owned by Tom Hanks.

Lessons for entrepreneurs abound in the movie as Ryan wrestles with the idea of whether to ask for help to save her business (do you let your customers know you’re struggling?), and there’s a poignant scene where the two founders discuss the, “It’s not personal, it’s business” trope.  

While the technology is certainly out of date (the entire plot revolves around AOL’s email and Instant Messenger), the themes of competitive pressure and changing customer demands are timeless.  

The Pursuit of Happyness

Chosen by Precious Drew, a Minnesota native investing in Black entrepreneurs through the Northwestern Mutual Black Founder Accelerator, “The Pursuit of Happyness” depicts the ugly reality of an entrepreneur’s journey to reach success when all odds are against them.

Precious says “The Pursuit of Happyness” is her favorite movie in this category because it encompasses a wholesome view of the entrepreneurship journey. There are peaks and valleys and times when things are stagnant. During the lows, the lead (Will Smith) exudes five key traits that are necessities for any entrepreneur: tenacity, self-awareness, time management, persuasiveness, and a willingness to take risks.

“The Pursuit of Happyness” will bring to light a new lesson about entrepreneurship, sacrifice, and resilience each time you watch it. Despite the difficulties of entrepreneurship, the film serves as a reminder that bad things don’t last forever and we, as entrepreneurs, are the authors of our own stories.

More to Watch

Several other movies were shared for their depictions of true entrepreneurial stories, some fictionalized and dramatized and others documentary-style films. What movies would you add?

  • Joy: “Joy” follows the journey of an inventor and consumer product pioneer.
  • Something Ventured: A documentary diving into the early venture capital investments of several iconic companies such as Cisco, Intel, and Atari.
  • Social Network: Based on the book “The Accidental Billionaires” by Ben Mezrich, this movie shares the origin of Facebook.
  • Molly’s Game: “Molly’s Game” details the life of a world-class skier who uses her network to build a poker empire.
  • The Founder: A portrayal of the rise of McDonald’s restaurant empire.
  • Steve Jobs: This film covers 14 years of the life of Steve Jobs, co-founder of Apple.
Elizabeth Caven
Elizabeth is an experienced entrepreneur-turned-fintech-investor. When not working with startups, she can be found remodeling old homes with her husband or embarrassing her four kids by cheering too loudly at their sporting events.