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The good. . . the bad. . . and the downright ugly.

Whether you are a seasoned business owner or someone just flirting with the idea of entrepreneurship, these films should definitely be on your watch list. From the fears and hardships associated with being a business owner to the rewards of bringing your vision to life, these movies cover it all.

So if you are in need of a good movie to watch. Tanzek Media has selected 8 movies that best depict the life of an entrepreneur. Enjoy.

Please Note: There may be very subtle spoilers included in this post. 

Jerry MaguireJerry Maguire

Synopsis: After the main character, Jerry, is fired from his job at a large sports agency he decides to build his own client base. In the process, Jerry ends up losing prospects as his attention is split, he breaks off the engagement with his fiancee only to rush into a marriage with another woman, and struggles to secure a reasonable contract for his only client.

How it Relates to Entrepreneurship: This film follows a man who struggled to build his own business after losing his job. It shows the dark side of solopreneurship that can include: disruption of your home life, competition, splitting your attention in too many different directions, and running into roadblock after roadblock on the path to success. On the other hand, it also shows how rewarding it can be to stay the course.


Daddy Day Care

Synopsis: Two men are unexpectedly laid off from their jobs and quickly become “Stay at Home Dads.” After struggling to find employment, they eventually decide to open up their own in-home daycare center. As their center grows in popularity, the head mistress at a local academy tries her best to put them out of business and gain her students back. 

How it Relates to Entrepreneurship: In this film, we see two men who suddenly lose their jobs trying to build something of their own. They have no idea what they are doing at first and are basically learning everything as they go – a concept many entrepreneurs are too familiar with. Just when they are finding a bit of success with their business, a much more seasoned competitor threatens to put them out of business. However, in the end, we see these entrepreneurs grow and discover their true passion. 


The Social Network

Synopsis: Viewers follow the journey of Harvard Undergrad, Mark Zuckerburg, as he builds a global social network and becomes the world’s youngest billionaire. 

How it Relates to Entrepreneurship: As we see in this film, growing a successful business comes with its own set of challenges. From lawsuits to issues with co-founders and broken friendships, we learn that building a billion-dollar company can be as challenging as it is rewarding. 


The Pursuit of HappynessThe Pursuit of Happyness

Synopsis: Based on a true story, this film follows a man by the name of Christopher Gardner. He invests all of his money into a “bone density scanner” that he believes will be quite profitable. However, he eventually learns that this luxury item is not an attractive purchase for physicians. He then struggles to make ends meet and finds himself living on the streets with his son while pursuing an unpaid internship as a stockbroker. This highly competitive internship can lead to a paid position only if Gardner can outshine the other interns in the midst of his struggles. 

How it Relates to Entrepreneurship: Many of us entrepreneurs have been there before – investing money in a business that you think will be profitable only to learn otherwise. Entrepreneurship can be a risky deal, but it’s okay to change paths when one is no longer working. 


Wolf of Wall Street

Synopsis: This story begins in the early 1990s when Jordan Belfort and his partner Donny Azoff start their own brokerage firm. As their team grows from a modest 20 employees to over 250, their firm quickly climbs in status. Their success leads to a stream of wild parties, trading schemes, and scrutiny from the FBI that threatens both their wealth and status. 

How it Relates to Entrepreneurship: Striking gold in your business venture is something that all entrepreneurs dream of. However, reaching such heights comes with great responsibility. Being dishonest and drawing unnecessary attention to your wealth can be very damaging to your success.


The Founder

Synopsis: A salesman by the name of Ray Kroc struggles to sell milkshake mixers to small drive-in restaurants across the U.S. During his travels, he acquires a slew of complaints about the operation of many drive-in restaurants. From long waiting times to incorrect orders, there are many things he simply does not like when it comes to fast-food restaurants. One day he learns from his secretary that a restaurant in San Bernadino, California has ordered six of his milkshake machines. It is at this point where he discovers McDonald’s – a small walk-up stand owned by two brothers. Ray eventually turns McDonald’s into one of the largest restaurant chains in the world.

How it Relates to Entrepreneurship: This film unpacks a lot of familiar situations for entrepreneurs. From building partnerships, taking risks, and expanding your business, to loyalty (or lack thereof) that can come with the territory. 



Synopsis: Viewers follow the story of Steve Jobs from a college dropout to the wildly successful co-founder of Apple.  In this film, we get to see the humble beginnings of the Apple brand transform into a booming business that has joined the stock exchange market. 

How it Relates to Entrepreneurship: We get to see how a well-known brand went from a small company operating from a garage to a massive corporation. Throughout the journey, we see the many ups and downs of building a successful business. From innovation to internal disputes, this film definitely depicts the life of an entrepreneur. 



Synopsis: A head chef quits his job at a restaurant due to his lack of creative control. He later opens up his own food truck where he sells Cuban sandwiches and yuca fries. With his pre-teen son and friend by his side, he takes his food truck cross country and finds success in several major cities. The success of his food truck eventually leads to an even bigger restaurant opportunity for him. 

How it Relates to Entrepreneurship: Many entrepreneurs decided to start their own business due to a lack of growth as an employee. We also typically begin our journey with a relatively small team. However, through trial, error, and innovation, we can build our brand into something big. 


There are many other great titles out there that tell the story of an entrepreneur, but this is a good list to start with. Feel free to share some of your best recommendations in the comments!


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