There’s a very fine line between a good entrepreneur movie and a great entrepreneur movie. The latter group consists of tales that are so epic, intense, and heart-wrenching that they are widely viewed as some of the greatest movies of all time. Memorable movies take you on a wild ride, and there is no ride wilder than the journey of the entrepreneur.
When most people see movies about business owners, their first thought is usually something along the lines of “I could never handle that,” or “You’d have to be insane to choose this path.”
Others, however, see these movies and think to themselves “I want that.” They want the excitement, the rewards, the power, and most importantly, the personal growth. Thanks to the silver screen, much of the world is well-aware that the brain and soul of a business owner are marvels to behold.
Perhaps this is the key characteristic of a great entrepreneur movie: inspiration. The following movies remind business owners why they chose this path and to be grateful for the crazy ups and downs they encounter every day.
Here are ten entrepreneur movies every business owner needs to see:
“There Will Be Blood” (2007)
No movie character embodies the drive, the cunning and the creativity of entrepreneurs better than Daniel Plainview, played by the legendary Daniel Day-Lewis. Set in the early 1900s, There Will Be Blood chronicles the evolution of a silver miner into a ruthless oil tycoon.
Many entrepreneurs would likely say that getting the business off the ground is the hardest part, and Plainview would certainly agree. Without employees or quality equipment, he constantly risks his life to find and excavate oil. And as the new kid on the block, Plainview must develop a disruptive business model to steal business from Standard Oil and other industry giants. This stage of the journey highlights the number one attribute of a successful salesmen: knowing your audience.
The film also shows the importance of capitalizing on the right opportunities. Plainview’s career takes off when he discovers a small, rural town with a wealth of oil under the dirt. Maintaining control of this asset, however, isn’t easy.
The average person would likely peg Plainview as a cold-hearted villain. An entrepreneur, on the other hand, wouldn’t be so sure. After all, the goal of every entrepreneur movie is to make the viewer think: Is this guy morally wrong, or is he just doing what he has to do to succeed?
What makes Plainview’s journey so universal is that you never really learn what motivates him. You don’t know why he’s working so hard. He just does it simply because it’s what he was born to do.
“Wall Street” (1987)
Wall Street made finance cool, thanks in no small part to cinema icon Gordon Gekko. The entire plot of Wall Street revolves around an illegal practice: insider trading. Played by Michael Douglas, Gekko makes most of his money by obtaining information that isn’t exactly public. This was a lot harder to do before hackers. Just ask Bud Fox (Charlie Sheen), who is tasked with literally following people around New York City to see what kind of deals are in the works. We all have to go the extra mile to get a foot in the door, right?
But you can’t blame Bud for desperately wanting to be Gekko’s friend. He dresses snazzy, has all the latest technology, and enjoys quality eats like steak tartare. Gekko’s energy is not only contagious, but also capable of skyrocketing from 0-100 in a matter of seconds. He’s the embodiment of confidence, and he showed a lot of people how they should carry themselves if they want to be successful.
Wall Street’s most significant contribution is its glamorization of the finance world. Before Wall Street, professional athletes and secret agents were the quintessential symbols of masculinity and toughness. But Gordon Gekko and Bud Fox proved that the real tough guys spend their days on the phone, getting stuff done.
In Moneyball, we are reminded that a sports team is still a business. In this true story, Oakland A’s owner Billy Beane (Brad Pitt) must somehow use a very limited budget to rebuild his team after losing several key players. His first move is strikingly similar to that of a new entrepreneur: think outside the box.
Beane recruits Peter Brandt (Jonah Hill), who has come up with an innovative, data-centric approach to assessing a player’s potential. Like countless entrepreneurs, Beane is repeatedly told that his plan is absolutely crazy and will never, ever work. It’s Beane and Brandt versus the entire baseball school of thought.
The season gets off to a bumpy start. But the pair refuse to give up on their strategy, largely because they have data on their side. Beane also realizes that his current managerial style is hurting the team. To show his faith in his players, Beane becomes more involved in their day-to-day lives and frequently meets with them to offer helpful suggestions. This emphasizes the tremendous value of transparency in business growth.
Beane’s story ultimately proves that if you’re smart enough and you believe in your ideas, a limited budget cannot stop you from reaching your goals.
“The Social Network” (2010)
The Social Network is to tech startups as Wall Street is to finance. Why work for an established company when you can get paid to wear casual clothing, indulge in illicit substances, and joke around with your friends all day? Sitting around a table cluttered with laptops never looked so fun!
But as we learn in the Social Network, the first version of Facebook was not started out of joy. It was fueled by Mark Zuckerberg’s anger at his recent ex-girlfriend and the female species in general. The Harvard student exposed the power of the Internet before anyone knew its capacity for spreading gossip or violating privacy. An act of revenge had created a new market. This allowed Zuckerberg (Jesse Eisenberg) to develop his vision for Facebook, down to the very last detail of a profile page.
From that moment forward, nothing stands in his way. Zuckerberg is so caught up in his vision that he neglects his friendship and business agreements with Eduardo Saverin, Facebook’s first investor. As any entrepreneur will tell you, this scenario is unfortunately common. The Social Network is a stern warning to anyone thinking of getting into business with a close friend. It also shows how success can change people for the worse.
Mark Zuckerberg knows better than anyone that growing a business can be treacherous if you’re not prepared.
“Up In The Air” (2009)
The entrepreneurial lifestyle can be lonely and unstable. It often involves a lot of traveling, arguing, and solitude. What kind of person would choose such a lifestyle?
Meet Ryan Bingham, the main character of Up In The Air. He spends the majority of his life traveling from state to state, where he gets paid to fire people (so the person’s actual employer doesn’t have to). But Ryan doesn’t mind sleeping in all these different places and not having many friends. He’s more comfortable in an airport or a conference room than a cozy living room. Sound familiar, entrepreneurs?
Ryan also doesn’t mind making strangers tear up on a daily basis. That’s what you have to deal with when you personally help people for a living. Ryan shows strength in situations that would make anyone else weak.
As the film progresses, we learn that Ryan’s lifestyle is largely attributed to a belief shared by many entrepreneurs: if you’re not growing, you’re dying. New experiences and challenges make Ryan feel alive, so why stay in one place? When work gets particularly hectic, entrepreneurs must always remember that they started their businesses because they love the process of personal growth, and that process never stops. The journey truly is the destination.
“Dallas Buyers Club” (2013)
Some businesses are born out of tragedy; or the desire to help others sharing your pain. Others are born out of innovation; or the discovery of a cheaper, more effective way to meet the needs of a niche market. When you combine the two, you get the Dallas Buyers Club.
It’s 1985, and Ron Woodroof (Matthew McConaughey) is diagnosed with AIDS and given 30 days to live. He quickly learns that AZT (the most prescribed AIDS medication at the time) is not going to be much help. But Ron doesn’t give up; he’s convinced there’s a better treatment out there somewhere. He ends up meeting a rogue doctor who has developed his own, all-natural medication that appears to be significantly safer and more effective than AZT.
The treatment is not FDA-approved. But like Mark Zuckerberg, Ron does not let legalities stop him from selling the treatment to the scores of other AIDS patients who have seen no results from AZT.
The true story of Ron Woodroof’s life-saving business venture is a perfect example of how entrepreneurship can turn a curse into a blessing. It also demonstrates what happens when high quality products and untapped markets collide. The quality of Ron’s products is unparalleled. But since no one has heard of him, he must recruit a partner (Jared Leto) to build a public following. And when demand skyrockets, it’s not as if Ron can simply hire more workers to boost production.
Anyone who has started a brick and mortar business from the ground up can relate to the story of the Dallas Buyers Club.
“Glengarry Glen Ross” (1992)
You’d be hard-pressed to find an entrepreneur who doesn’t know the phrase “ABC: Always Be Closing.” This immortal sales mantra comes from Glengarry Glen Ross, which is based off a Pulitzer Prize-winning play by David Mamet. At the beginning of the film, a group of real estate salesmen are told that the two lowest sellers in the office will be fired at the end of the month.
The news is broken by Alec Baldwin, who says “ABC” to remind the team that they should never let a potential client off the phone until they have done everything in their power to close the sale. Owners of sales-centric businesses have likely given their teams similar advice. They’re trying to prevent their salespeople from submissively accepting responses like “Let me think about it” or “I have to talk to my wife/husband first.”
If you’ve spoken to a cold calling salesperson, you’ve probably heard some of the aggressive tactics used in Glengarry Glen Ross. Sales is not for the light-hearted, as we learn throughout the team’s desperate quest to save their jobs. Losing out on a potential sale is a blow to your self-worth.
Another timeless aspect of the film is the strategic emphasis on the product’s emotional and psychological benefits. Top seller Ricky Roma (Al Pacino) doesn’t just sell houses. He sells the lifestyle that comes with owning property in a desirable area.
“The Intern” (2015)
This entrepreneur movie proves that if you’re willing to learn, you can succeed at virtually any company. 71-year-old Ben Whittaker (Robert DeNiro) lands an internship at About the Fit, a fashion startup run by founder and CEO Jules Ostin (Anne Hathaway). Ben is so grateful for the opportunity that despite his age, he strives to help the company out in any way he can. He organizes messy workspaces, provides fatherly advice to his younger colleagues, and gradually removes more stress from Jules’ work and personal life.
Jules is very much the typical entrepreneur; working so much that she has little time for her family. Her relationship with her husband is beginning to deteriorate. Jules’ workload has actually become so overwhelming that the company’s investors have asked her to step down as CEO, so someone with more experience can take over. Though Jules wants to spend more time with her family, it’s abundantly clear that her company means more to her than anything. She remains heavily involved in day-to-day operations and is often the last person to the leave the office.
Entrepreneurs can see parts of themselves in both characters (DeNiro and Hathaway). Jules isn’t sure what to do because her company is so close to her heart. Ben, on the other hand, possesses the drive and curiosity that allows future entrepreneurs to take an active role at their first opportunities. A natural-born entrepreneur will shine at any company. It doesn’t matter if they have no relevant experience and cannot relate to the target customer.
“Office Space” (1999)
Few movies have captured the reality of desk jobs and corporate culture more accurately than Office Space. The employees of software engineering firm Initech feel no connection to their work. The minor inconveniences of their daily routines have become borderline unbearable. Their misery is largely attributed to the passive-aggressive managerial style of their boss.
Everyone has worked for someone like Bill Lumbergh (Gary Cole). He doesn’t raise his voice but he talks to his employees like a soulless robot. Employees are carelessly assigned more and more work as if it’s no big deal to the person who has to do it. Lumbergh literally does everything a good boss wouldn’t do. Take a lesson, entrepreneurs: If your employees don’t seem to care about their work, it might be because you conduct yourself a little like Bill Lumbergh.
One of the film’s central messages is that every job involves some sort of boring, monotonous work. But you don’t have to let these things ruin your life. Office Space taught us that the most annoying parts about our jobs are often quite funny, albeit in hindsight. And as unpleasant as your boss might be, at least he’s not Bill Lumbergh.
“Jerry Maguire” (1996)
Many entrepreneurs started their businesses to solve a major problem with the industry they’ve been working in for years. They refuse to stay complacent because they care more about their customers than making money. For sports agent Jerry Maguire (Tom Cruise), that problem is the lack of a personal relationships with his clients, which ultimately stems from juggling so many of them. Despite his financial success, Maguire feels empty because his clients can’t even remember his name.
This leads Maguire to open up his own sports management agency. He has just one client; football player Ron Tidwell (Cuba Gooding Jr.). Entrepreneurs can certainly relate to Maguire’s devotion to Tidwell, who is not easy to deal with. Anyone who runs a service-based business knows that your fist clients are treated like royalty. They must never suspect that they are not your number one priority. Maguire and Tidwell get into several heated arguments but they also believe in each other and push each other to succeed.
Watching this entrepreneur movie can make entrepreneurs re-assess their role in the lives of their customers and/or employees. Maguire is directly involved in Tidwell’s personal growth. Tidwell’s victories on the gridiron feel like a personal victory for him, as well. The point is, success is infinitely sweeter when it is the result of multiple people working together.
Entrepreneur Movies: Honorable Mentions
“The Wolf of Wall Street” (2013)
Aspiring entrepreneurs often tell themselves that they won’t break the rules or take advantage of their customers like everyone else. The Wolf of Wall Street brilliantly reveals what motivates so many good people to take this route. For one thing, it makes work not feel like “work” anymore. Buying new cars, watches and houses is a lot harder when you play by the rules. And when it’s this easy to trick someone into giving you their money, what is really to blame: your maliciousness or their foolish innocence?
The true story of Joy Mangano, the inventor of the Miracle Mop and one of the hardest working entrepreneurs ever shown on screen. Mangano overcomes a myriad of obstacles to give her product mass exposure, including her gender. No one has ever seen a product like this before. With no outside help, Mangano must figure out a new way to market it. The film also delves into the chaos of patent lawsuits and meeting unprecedented surges in demand. Once Mangano’s on top, her personal and professional rivals try to bring her right back down. You’ll be out of excuses for not starting your business after watching Joy.