15 Movies Every Entrepreneur Should Watch for Inspiration

The life of an entrepreneur consists of constant change and activities. Running a business involves dealing with changes, surprises, and challenging situations daily.

Entrepreneurs experience stress in managing their businesses and people. They may also need help to sustain their revenue. As an entrepreneur, you may wonder whether your experiences in the industry are typical. And you may also wonder if other entrepreneurs face the same challenges as you.

Due to difficulties and circumstances, some businessmen feel like giving up and quitting their dreams of having a successful business. According to research, in 2021, 20 percent of small businesses failed in the first year and 50 percent within five years.

The idea of trying something several times only to be met with defeat every time may sound highly discouraging. But as an entrepreneur, your life will feel like a roller coaster. One moment, you are riding the high of a successful product launch. And in the next moment, you’re doubting your entrepreneurial endeavors.

Some entrepreneur movies can inspire you if you are having difficulty running your own business or achieving success. Typically, movies are created to entertain, but some are made to inspire people.

Some of these inspiring movies are based on real-life stories. These stories may motivate you to achieve your dreams of a successful business.

Here are some movies every entrepreneur should watch to be inspired to continue pursuing their dreams.

Key Takeaways Many entrepreneur movies show the life of successful business people and their challenges. Several entrepreneurs fail due to morally questionable decisions they have made. Films about businesses often inspire many entrepreneurs, especially young ones, to never give up on their dreams of owning a successful business.

1. The Social Network (2010)

Do you know the story behind Facebook and how it started? “The Social Network” shows how the most popular social media platform, Facebook, was created by Mark Zuckerberg while studying at Harvard.

Plot

In 2003, computer genius and Harvard undergrad Mark Zuckerberg started working on a new concept that became a global social network, Facebook. He created a website to rate female students at his college after his girlfriend dumped him.

After six years, he became one of the youngest billionaires. Still, his unparalleled success resulted in personal and legal issues.

He received two lawsuits, one from his former friend and the other from the Winklevoss twins, who believe that Mark Zuckerberg stole their idea.

Why watch the film?

“The Social Network” shows how Facebook started and reminds you that many big companies started from small beginnings. It showcases the challenges, successes, and complexities of starting and scaling a tech company. It also offers lessons on innovation, leadership, and perseverance.

2. Wall Street (1987)

“Wall Street” is an all-time classic business movie showing the dark street where the mantra is “Greed is Good.” Oliver Stone directed the film, which tells a story of ambition and man’s desire for wealth.

Plot

In the 1980s, Bud Fox, an ambitious stockbroker on Wall Street, does whatever he can to reach the top. Inspired by the unsparing corporate raider Gordon Gekko, Fox tempts Gekko to mentor him by providing insider trading.

As Fox becomes involved in fraudulent schemes and greed, his decision eventually affects the livelihood of his righteous father. Faced with this dilemma, Fox questions his loyalties.

Why watch the film?

Young entrepreneurs are often lured by greed, encouraging them to make morally reprehensible decisions. “Wall Street” is a cautionary tale about how ambition and desire can lead us down an unethical path.

3. Glengarry Glen Ross (1992)

Starring Al Pacino, Kevin Spacey, Jack Lemmon, and Alec Baldwin, this film is adapted from an award-winning play that shows the life of real estate salespeople in a tumultuous sales season.

Plot

The film shows two days in the lives of four real estate sales associates who must compete when the corporate office sends a motivational trainer and threatens them that everyone will be fired except the top two at the end of the week. 

Shelley Levene does everything he can to get better leads than his boss, John Williamson, but he fails. When Dave Moss, his coworker, suggests a plan to steal these leads, things become complicated for the sales associates.

Why watch the film?

“Glengarry Glen Ross” is a great entrepreneur movie that will inspire you to use your wits to survive and thrive in a high-pressure business world, especially in real estate sales. The film has been used to train salespeople to become better sellers as it teaches them the proper and improper ways to sell.

4. The Founder (2016)

This film explores the life of Ray Kroc, the founder of McDonald’s, and his creation of the biggest fast-food restaurant chain worldwide.

Plot

The movie is set in the 1950s and follows Ray Kroc, a struggling milkshake machine salesman, as he comes across a unique and efficient fast-food restaurant run by the McDonald brothers, Dick and Mac, in San Bernardino, California.

Ray is amazed by the innovative “Speedee Service System” they have developed, which revolutionizes how quickly and efficiently food is served. Impressed by the potential of their concept, Ray convinces the McDonald brothers to let him franchise their brand.

Why watch the film?

The movie highlights seizing opportunities and hard work. It provides insights into entrepreneurship’s challenges, triumphs, and controversies, making it a thought-provoking movie for aspiring entrepreneurs and business professionals.

5. The Wolf of Wall Street (2013)

The “Wolf of Wall Street” follows the real-life story of Jordan Belfort and his rise and fall as an entrepreneur. It also shows how his firm, Stratton Oakmont, was involved in penny stock trading and securities scams, which drew the attention of the FBI.

The spectacular performances by Leonardo DiCaprio, Margot Robbie, Jonah Hill, and Matthew McConaughey will keep you entertained as Martin Scorsese brilliantly directs the film.

Plot

In 1987, Jordan Belfort took an entry-level job at a Wall Street brokerage firm. While in his 20s, he founded his firm, Stratton Oakmont.

With his trusted lieutenant and a group of brokers, Belfort makes a great fortune by deceiving wealthy investors. Despite the excessive lifestyle Belfort and his associates led, which included drugs, sex, and other extravagances, the FBI and SEC were eventually successful in their pursuit of his illegal activities.

Why watch the film?

Many entrepreneurs are driven by greed, have no empathy toward other people, and live a life of extreme corruption, which may lead to their downfall. Jordan Belfort is the best example of what type of an entrepreneur you shouldn’t be.

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6. Jobs (2013)

The movie “Jobs” lays out the inspiring story of Steve Jobs of Apple fame. It shows how he overcame many obstacles and failures to achieve great success. Despite facing difficulties, Jobs never wavered in his pursuit of excellence.

Plot

College dropout Steve Jobs and his friend, Steve Wozniak, started a revolution in home computers by inventing the Apple 1 in 1976. He created the device in his parent’s garage, eventually changing the world forever.

Steve Jobs is seen as a visionary; however, his term as Apple’s leader and co-founder is challenging. And this results in his eventual ouster from the company.

Why watch the film?

The movie focuses on the rise and fall of Steve Jobs in achieving this tremendous success. It depicts his difficulties with relationships, failures, and betrayal before becoming the founder of this empire.

“Jobs” is considered one of the best entrepreneur movies ever as it tells the unseen side of the aching pain and failures of the most successful business leaders.

7. The Big Short

“The Big Short” shows the story of three people who were able to predict and earn from the American financial crisis of 2007-08. It is recognized for utilizing unconventional techniques to explain complicated and tedious financial concepts, such as collateralized debt obligations (CDOs) and subprime mortgages.

Plot

In 2008, Wall Street guru Michael Burry discovered that several subprime home loans would likely default. So he bets against the housing market by investing more than $1 billion into credit default swaps.

This gets the attention of banker Jared Vennett, hedge-fund specialist Mark Baum, and other opportunists. These men make a great fortune by taking advantage of the impending economic crisis in America.

Why watch the film?

“The Big Short” is a must-watch if you seek to understand the financial crisis of 2007. It serves as a lesson to business people and entrepreneurs, demonstrating the value of having conviction and taking risks to pursue success.

8. Pirates of Silicon Valley (1997)

The movie “Pirates of Silicon Valley” tells the rivalry between Bill Gates and Steve Jobs from 1971 to 1997. It shows the work of the two most successful entrepreneurs in the world, their brilliant minds, their struggles, and the betrayals they experienced in the business world.

Plot

The film shows the real-life story of how Bill Gates and Steve Jobs made a difference in technology. It chronicles the birth of the two most prominent companies in the world, Microsoft and Apple, during the 1970s and how they became the most influential corporation in the IT field.

Why watch the film?

“Pirates of Silicon Valley” shows the humble beginnings of two billionaires and the most iconic technology companies worldwide. As an entrepreneur, you will be inspired by how they achieve their success and overcome their challenges.

9. American Hustle (2013)

“American Hustle” was released in 2013 and directed by David O. Russell. It is a fictionalized account of the Abscam scandal, an FBI sting operation in the late 1970s and early 1980s that targeted corrupt politicians. 

Plot

Irving Rosenfeld is a hustler who enjoys engaging in fraudulent activities like forgery and loan-sharking. However, with the arrival of Sydney Prosser into his life, his perception of the world changes significantly. 

Irving and Sydney are caught red-handed by Richie DiMaso, an FBI agent. They are forced to work undercover as part of DiMaso’s sting operation to capture a New Jersey.

Meanwhile, Irving’s unpredictable wife, portrayed by Jennifer Lawrence, may bring everyone’s world crashing down.

Why watch the film?

As an entrepreneur, watching the film “American Hustle” can provide several lessons and insights that may apply to the business world. It is a cautionary tale about the consequences of unethical and illegal behavior while offering lessons on adaptability, risk management, perception, ethics, relationships, resilience, and attention to detail.

It’s important to remember that while the film portrays a fictional story, its lessons and insights can still apply to the challenges and opportunities entrepreneurs face in their business endeavors.  

10. Startup.com (2001)

“Startup.com” is an American documentary film that follows the dot-com startup govWorks.com, which raised $60 million in funding from KKR, Hearts Interactive Media, the New York Investment, and Sapient.

Plot

The movie tells the story of failed dot-com operation GovWorks, which aimed to create an online platform that facilitates communication between local governments and their constituents, streamlining various government services and processes. It follows the story of Kaleil Tuzman, who quits his job at Goldman Sachs to start working on GovWorks with his friend, Tom Herman.

The startup raised $60 million in funding from several corporations but didn’t survive. And it became a reference for lessons learned for entrepreneurs.

Why watch the film?

“Startup.com” focuses on the consequences of incompetent management and improperly placed accents in the control of a promising company. It is a sobering tale for entrepreneurs about how friendships can turn into bitter rivalries due to internal politics.

11. Moneyball (2011)

Starring Brad Pitt, “Moneyball” is a film about the Oakland Athletics baseball team and Billy Beane, the team’s general manager. It shows how he builds his team with a limited budget to achieve excellent results in the Major Baseball League (MLB)

Plot

Billy Beane is dumbfounded by the team’s loss in the 2001 American League Division Series when he meets Peter Brand, an economics graduate from Yale University with radical ideas about evaluating players.

Beane must build his team by tricking the richer ball clubs. With Peter Brand, they prepare to challenge old-school traditions and recruit bargain-bin players.

Why watch the film?

Just like Billy Beane, most startups face challenges in which they must take risks and make tough decisions to achieve success. Often, they encounter a similar scenario when they must go against intense competition like established businesses in the market.

12. The Pursuit of Happyness (2006)

This movie is a true story based on the life of Chris Gardner, played by Will Smith, and his struggles with being homeless with his son while undergoing a gruelling 6-month unpaid internship as a stockbroker. 

Plot

Christopher Gardner invested in a device known as a bone density scanner, but it didn’t sell well. He loses his wife and apartment as he works to make ends meet.

Eventually, Chris lands a job as an intern at a prestigious brokerage firm, but the position doesn’t pay money. Therefore, the father and son pair have to live in shelters and survive many challenges. But Chris doesn’t want to give up even though he struggles to give his son a better life.

Why watch the film?

Chris Gardner experiences circumstances and challenges that make achieving his dream difficult and seem impossible. These circumstances and challenges are similar to what startups face.

This movie will inspire you not to give up on your dream of achieving success in business, even though life is full of challenges and hardships.

13. Aviator (2004)

The movie is a biopic of the eccentric billionaire Howard Hughes, who overcame all the challenges to become a successful film director and famous businessman. The “Aviator” is touted as one of the best biographical movies ever.

Plot

Howard Hughes, a billionaire and aviation tycoon, is a successful director and businessman, a passionate lover of Katharine Hepburn and Ava Gardner, and a pioneer who helped establish TWA as a major airline.

However, Hughes is tormented as he suffers from paralyzing phobias and depression. He fights his inner demons in a lonely room.

Why watch the film?

Aside from competing with rival companies with heavy purses and movie moguls with powerful connections, Howard Hughes also fought his internal battle with an enfeebling mental issue like OCD. However, this did not stop him from becoming an innovator. 

Through this film, entrepreneurs can learn various lessons, including balancing personal and business life, risk management, innovation and marketing, and passion and perseverance. 

14. Fyre: The Greatest Party That Never Happened (2019)

This is a Netflix documentary movie that provides an exclusive behind-the-scenes look at the ill-fated music festival. It includes some shocking revelations from the stranded festival-goers, unfortunate team members of the organizer, Billy McFarland, and the heartbreaking story of a Bahamian restaurateur.

Plot

Fyre Festival was expected to be the most incredible music festival ever. Some celebrities and social media influencers, such as Bella Hadid and Kendall Jenner, promoted it. However, it was all a scam organized by MacFarland, who already had a history of fraudulent business ventures.

Billy McFarland and his business partner, rapper Ja Rule, promised a luxurious music festival filled with celebrities, catered food, and cabanas in the Bahamas. Since social media influencers heavily promoted it on Instagram, many moneyed millennials bought tickets.

However, upon arrival, they only find an unfinished campsite and plain cheese on bread instead of luxurious cuisine. There were also no performers.

Social media and the internet were flooded with stories, pictures, and videos from the festival. The festival got cancelled, and McFarland was sentenced to six years in prison and fined for fraud.

Why watch the film?

This documentary film is a cautionary tale for young business people and entrepreneurs about making promises and not delivering a satisfactory product. Billy MacFarland is an example of an entrepreneur you shouldn’t be, as he offers misleading promises and misrepresented facts to sell high-priced tickets.

The film also serves as a reminder for entrepreneurs who invest tremendous money in advertising and marketing without improving the product. The festival had excellent marketing due to the enormous fan base of social media influencers. However, the event needed better management, and the organizers thought they could escape.

15. Jerry Maguire (1996)

“Jerry Maguire” is a movie that gives an insightful perspective on what it takes to be a sports agent. It is full of advice for entrepreneurs struggling in the business world.

Plot

When Jerry Maguire, a clever sports agent, has a crisis of conscience, he writes a sincere company-wide memo that gets him fired immediately.

Jerry establishes his management firm with Dorothy Boyd joining him. He is desperate to hang on to the athletes he represents — banking on their only client, football player Rod Tidwell. Dorothy and Jerry fall in love with each other as they struggle to make their business work.

Why watch the film?

This film is an eye-opener for entrepreneurs stuck in the money world who want to get out of a rut. It underscores the importance of authenticity and ethics in business dealings. 

Maguire’s decision to prioritize honesty, integrity, and genuine care for his clients over purely profit-driven motives is a valuable lesson for entrepreneurs. Building a business based on ethical principles, treating customers, clients, and partners with respect, and being true to one’s values can contribute to long-term success and sustainability.

Watch the Best Entrepreneur Movies To Inspire You

As an entrepreneur, you will face different challenges in the business world that may discourage you. If you need inspiration or a break from your intense work schedule, watching these entrepreneur movies may inspire and motivate you to succeed. They will also teach you important lessons in business and life that can help you achieve your dreams as a business person.

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