Lessons from movies about entrepreneurship

Movies can be much more than simple entertainment. And this is especially true for the small business owner who looks for advice and inspiration, as the day-to-day of managing a business can be very challenging. 

Regardless of the state your business is in, you, the business owner, will still need inspiration and insight from time to time. What better way than to get this from legendary entrepreneurs from the comfort of your home? 

Here are the 10 best movies about entrepreneurship for entrepreneurs.

Moneyball (2011)

Moneyball movie poster, courtesy from Sony Pictures


With a screenplay written by Aaron Sorkin and Steve Zailian, Moneyball tells the story of how Billy Beane implemented the concept of the same name for the small league baseball team Oakland Athletics in the early 2000’s. This breakthrough method went against traditional scouting in the sport, as it placed no emphasis on the physical attributes of the athlete, but only the likeliness of the player to get on base and hit.

With the task of building a new team under a significantly smaller budget and having great last season names transferred to other teams, Billy Beane (Brad Pitt) then met the under-appreciated 25-year-old Peter Brand (Jonah Hill), who introduced him to the concept of Moneyball. He was instantly hooked, but all his experienced scouts doubted him. To that Billy said, “adapt or die”, and “never once lost faith” in his idea for change.

Though the Oakland A’s started the season on a losing streak, Beane’s new players weren’t being played by coach Art Howe (Phillip Seymour Hoffman). He decided to risk his job and pulled a few more strings to indirectly force the coach to cast the lineup he intended. He did the unthinkable, and transferred two key players to other teams, including one who had the potential of being an All Star. Though the Oakland A’s lost the final game of the season, they beat the world record of winning 20 games in a row.

Moneyball is about doing what everyone may believe is a mistake, except you. It’s about faith and the courage to stick with your guts. You can watch Moneyball on HBO Nordic.

The Big Short (2015)

The Big Short movie poster, courtesy from Paramount Pictures

Directed by Adam McKay, The Big Short portrays the story of how a group of people foresaw the US housing and mortgage market crash and managed to profit out of it.

Though the movie displays heavy economic jargon through its entirety, there is a lesson for entrepreneurs in the story it portrays. And this comes from its leading entrepreneur, Michael Burry (Christian Bale), who was the first to realize a big opportunity in an unseen flaw: the US housing market was overvalued. In fact, the US housing market was always seen as a safe bet, with its CDO market worth 226 USD in 2006. However, Burry’s breakthrough insight was that the entire market was based on risky mortgages.

It is possible to make large profits by predicting a given product will fail. And you can transfer this risk to someone else’s hands, as long as you pay them. That is what Michael Burry did, and with him many other investors who were convinced by him. The banks happily accepted Burry’s investments, and the risk, because they were adamant the housing prices would continue to rise.

When the market collapsed, the banks were forced to pay him, and he alone made 750 million USD from the crash. Though the 2008 crisis had terrible consequences for millions of Americans, Michael Burry tried to make his contribution fruitful from what proved drastic to millions of people. He contacted the government and offered to explain how he got his prediction, but he was unanswered, and later audited and questioned by the FBI.

The Big Short shows how a handful of talented men were able to make gains from a worldwide crisis. Though it can be seen as a story of opportunism, it is also a tale of how a few can shake a whole system by seeing a flaw that none witnessed before. And how a single flaw changed the lives of millions. You can watch The Big Short on Netflix

Steve Jobs (2015)

Steve Jobs movie poster, courtesy from Universal Pictures

Steve Jobs is a biopic around the former co-founder and CEO of Apple Inc. The movie is centered around the backstage of 3 key-product launches, where Jobs’ flaws are exposed, especially his insensitivity towards co-workers and family members. Despite this, it can be easily argued that his flaws are greatly overshadowed by his qualities and talents, which made him a great entrepreneur.

Then, what made Steve Jobs (Michael Fassbender) a great entrepreneur? It is a fact, that Jobs, as many other entrepreneurs in this list, such as Ray Kroc and Billy Beane, was not the inventor of the Mac. He benefited from a network of great minds working alongside him, but that is where his greatest talent came from: coordinating talents with incredible tenacity and a mind for what makes business attractive to the public. An example of this comes from the Lisa launch of 1984, where he made it mandatory for the computer to say “hello” during the presentation. The idea behind it was to break against the Hollywood representation of computers until then, most notably in 2001: A Space Odyssey, and to show instead a friendly and eye-pleasing instrument. Jobs’ belief that the computer should be seen as a work of art is partially what still makes Apple computers very attractive to consumers.    

Though entrepreneurs often do not “create” but instead, in Jobs’ words, “play the orchestra”, their contribution to society is immeasurable. It is through their work that their product becomes larger than life and able to become much bigger (and transformative) than the original creators intended or anticipated. Such is the power of innovation, you can always make it greater, and bigger. 

Steve Jobs shows first-hand how entrepreneurs are fighters with a vision. They never settle. And their relentless dedication is what makes them achieve greatness. You can watch Steve Jobs on Viaplay

The Aviator (2004)

The Aviator movie poster, courtesy from Warner Bros. Pictures

Legendary director Martin Scorsese’s The Aviator depicts Howard Hughes’s rise and fall. Hughes (Leonardo DiCaprio) was a wealthy businessman who dabbled and changed the course of the aviation and the film industries. Partly, his undying dedication to his vision made him incredibly successful, that despite some failures along the way, such as aircraft H-4 Hercules (which was unable to get fully airborne), he never once admitted failure

In a few scenes in the movie, Hughes demanded to his employees that the rivets on his plane be placed exactly right to make the aircraft more aerodynamic. His attention to detail and perfectionism is highly valued in an entrepreneur, as the quality you impose on your own product generates a higher final value, and potentially flawless result. And not only was Hughes an innovator, with immense persistence, and perfectionism, he knew how to properly delegate tasks to a hand-picked selected team. This is a quality he shares with Steve Jobs, as the ability to coordinate the talent that surrounds you as an entrepreneur is crucial, as it can make you (and your company as a whole) stand out immensely. 

Howard Hughes was a risk-taker with a vision. He was able to see the risks, but he was devoted to his own success. Though he spent his last years shut off from society, Hughes’ tale of ambition, persistence, and ultimately success – beyond the laughter and criticism from both the film and aviation industries – immortalized him as a great entrepreneur. More than a man fighting his demons by the end of his life, The Aviator shows a leader that despite his struggles, will never have his victories taken away. You can watch The Aviator on Netflix.

The Wolf of Wall Street (2013)

The Wolf of Wall Street (2013), courtesy from Paramount Pictures


In several ways, Martin Scorsese’s The Wolf of Wall Street is more of a cautionary tale of what not to do in entrepreneurship – considering his later imprisonment. However, there are several lessons you, the entrepreneur, can learn from his meteoric rise to success.

From the start of the movie, when Jordan Belfort (Leonardo DiCaprio) goes to lunch with his colleague, he is driven to do things bigger, and go higher. Even when he loses his job and goes to a much smaller firm, it’s his determination to never settle that inspires his teammates and ends up with the founding of Stratton Oakmont. This is also seen when he teaches his colleagues how to sell, and never take no for an answer.

His relationship to his colleagues is another reason why he was so successful. When giving a speech to announce he was leaving the firm, he shares the story of Kimmie, who came to him asking for a job and a 5 thousand advance so she could pay her son’s tuition. Jordan reveals he gave her a check of 25 thousand dollars instead, and the biggest proof for the viewer to witness that his trust paid off was to see she became a successful woman, wearing a “3 thousand dollar Armani Suit”. That is how Jordan kept his employees motivated and loyal to him, which has tremendous importance for a business to succeed.

Though he went to prison for 22 months on charges of money laundering, Jordan Belfort is now a motivational speaker for entrepreneurs and his net worth is still of 100 million. As he said it himself, “do it differently each time. One day you will do it right. Failure is your friend”. And that is why the Wolf of Wall Street has its higher power of inspiration: Belfort’s ability to reinvent himself even after reaching rock bottom. Failure should never be an option for the entrepreneur, only a setback. You can watch The Wolf of Wall Street on HBO Nordic

Wall Street (1987)

Wall Street movie poster, courtesy from 20th Century Fox

Oliver Stone’s 1987 classic Wall Street tells the story of Bud Fox (Charlie Sheen), a broker who is hungry for success, becoming the pupil of mogul Gordon Gekko (Michael Douglas). This is yet another story of how an entrepreneur’s break might come just by meeting the right person. And this is Wall Street: where friendship quickly ends in battle and betrayal between the two protagonists.

There are, however, important lessons to be learned from Gordon Gekko. Early in the movie, he assures Fox about the power of information. Without information, every battle would be uncertain, and potentially lost. And Gekko’s hunger for certainty is what makes him a figure of power: he does not invest unless he knows he will win. But what does it take to know?

In Gekko’s mind, greed is good. Greed works, as it is the fuel for how our daily lives are based. It is clear to the viewer that there is a clear limit to the benefits of greed in Wall Street. 

More than a direct lesson, Oliver Stone’s classic sets questions in the viewer’s mind once the credits roll. What is the cost of greed without meaning or a moral payback? What do we lose when we gain more money than we ever imagined? Is it worth it? You can watch Wall Street on Prime Video

Jerry Maguire (1996)

Jerry Maguire movie poster, courtesy from Sony Pictures Releasing

Contrary to the majority of the films in this list, Jerry Maguire, directed by Cameron Crowe, is a heartfelt journey about a sports agent (Tom Cruise) who loses everything after writing a 25-page mission statement for his company, suggesting they choose to focus on their clients, and not the money. 

After having a career on the limelight and reaching success at a young age, Jerry finds that only two people will follow him and his new ethos: Rod Tidwell (Cuba Gooding Jr), a B-list NFL player, and the accountant Dorothy (Renée Zellweger). 

Despite bootstrapping) for his sole client, who needed his help to be able to support his family, Jerry is pushed towards his very best. And his commitment and dedication towards his client finally pays off, when Rod has his chance to shine in the Superbowl. Since his main objective was not his own profit, but instead to do the best for his client, Jerry got the recognition he deserved. 

That is why Jerry Maguire proves to be a classic tale of the entrepreneur: the one who dares to do it alone (and at least has one client), as long as he/she is determined, will find success. You can watch Jerry Maguire on Viaplay.

The Founder (2016)

The Founder movie poster, courtesy from The Weinstein Company

The Founder tells the story of how Ray Kroc (Michael Keaton) transformed the McDonald’s original restaurant into a global franchise.

Founded by brothers Richard and Maurice McDonald (Nick Offerman and John Carroll Lynch), Ray Kroc first came into contact with them by selling them milkshake machines that aligned with their developed concept of fast food. In fact, the brothers were the ones who developed the fast-food concept and optimized the restaurant by removing all unnecessary aspects in the way of a speedy delivery.

When Kroc suggests to the brothers that they franchise the restaurant, the brothers say they attempted this, but stopped because of quality control. However, Kroc’s belief in the potential of McDonald’s, and his dedication drove him to the point of mortgaging his house to build one of the franchises. His financial break is when he meets Harry Sonneborn, who suggests Kroc purchases the land where the restaurant sits and leases it to the franchisee. In fact, Kroc and Sonneborn were the original masterminds of the franchising system.

Success quickly follows Ray Kroc after this point, when he decides to buy McDonald’s from the brothers. In fact, Kroc’s vision for the fast-food chain was dramatically different from what the brothers intended. Though the brothers were breakthrough innovators, they did not wish to scale their business to the point they thought they would lose quality and their core identity in the process. 

And that’s how The Founder portrays Ray Kroc as a tremendously successful businessman: for his belief in the name of the business, his search for alternatives that would keep optimizing the chain, and his ruthless attitude. You can watch The Founder on Viaplay

The Social Network (2011)

The Social Network movie poster, courtesy from Sony Pictures Releasing

The Social Network begins with Mark Zuckerberg (Jesse Eisenberg), a talented Harvard student, being approached by Tyler and Cameron Winklevoss (Armie Hammer) and Divya Narendra (Max Minghella) with an offer to program a social network platform exclusive to Harvard students. Though Zuckerberg agrees to help them, he goes directly to his friend Eduardo Saverin (Andrew Garfield) with an idea to build their own (and better) platform, The Facebook. 

The pair’s network quickly gains popularity in the campus and follows through to other universities. At a point in the movie, Zuckerberg compares Facebook to fashion, which explains why the platform or its model, has not gone out of popularity: it is always changing, always adapting, and it will never be in its final version. That is one of the many reasons Facebook was and still is groundbreaking, because of the continuous addition of features and tools. As an example, as the world faces a pandemic, many businesses are forced to go into the digital market. And what is the most popular and successful platform for companies to use for this purpose? It is Facebook Business.

Similar to Ray Kroc and Harry Sonneborn, Mark Zuckerberg met Sean Parker, who believed Facebook had the potential to become a billion-dollar company and got them investments that ultimately transformed the social network into a giant business. The similarities don’t stop there, as he was also forced to settle lawsuits against the Winklevoss brothers, Divya Narendra and also Eduardo Saverin. 

The Social Network can be seen as a story of betrayal, but it can also be seen as a story of how the people we know can bring us where we want to go. Unfortunately, business doesn’t mix well with friendships. You can watch The Social Network on Netflix

Glengarry Glen Ross (1992)

More than any of the other movies in this list, Glengarry Glen Ross depicts what a company should not do in any circumstance to their employees – a high pressure, high stakes demand that is unlikely to be fulfilled even by the best sales strategy. Be warned!

Early in the movie, the salesmen from a real estate agency are informed of a sales competition, where the top salesman of the month would win a Cadillac car, the second place a collection of steak knives. However, the other salesmen would be fired. 

The men are only granted weak leads, and complain to their supervisor of the unfair request from management. The manager proves to be inflexible to their requests and refuses to supply them with the better leads – which would only be passed to the salesmen who closed deals in the first stage of the competition.

The lack of flexibility from management makes things turn for the worse, as the salesmen Aaronow (Alan Arkin) and Moss (Ed Harris) start elaborating plans within themselves to stage a theft in the office and steal the better leads, to later sell them to their competitor. But it’s when Shelley Levene (Jack Lemmon) receives a call informing him of an urgency in his family, though he was the one who arguably tried his hardest to make a sale in the unlikely circumstances he was set, he decides to stage the theft in his firm and sell the valuable leads to their competitor.

Glengarry Glen Ross provides a lesson for businesses as in never to set unrealistic objectives for a staff that does not have the necessary tools to meet those goals. Out of desperation, this can turn a salvageable situation into a hopeless, criminal, act. You can watch Glengarry Glen Ross on Prime Video or Hulu.

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