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The Wolf of Wall Street. Photo by Warner Bros.

Top 25 Must-Watch Entrepreneur Movies That Will Inspire You

Entrepreneurs, like the rest of us, require inspiration from time to time. What better way to get inspired than to take a break and watch some thought-provoking films?

Regardless of where you are in your entrepreneurial journey, watching movies about the human condition and how adversity can be overcome through sheer mental fortitude, perseverance, and discipline will provide you with much-needed inspiration. Or just pure serendipity combined with luck!

1. The Shawshank Redemption (1994)

This film depicts how two imprisoned men bond over time and eventually find redemption through acts of common decency.

A successful banker is imprisoned after being found guilty of his wife’s murder, which he did not actually commit.

Watching how he copes with his ordeal and makes friends with other inmates, particularly a wise long-term inmate named Red, will inspire you more than anything else.

Key Takeaway: Small changes that add up over time can have the greatest impact.

2. The Social Network (2010)

After being dumped by his girlfriend, Mark creates Facemash, a campus website that allows site visitors to rate the attractiveness of female students.

Facemash’s popularity prompted him to launch Thefacebook, a social networking site.

It is one of the best business movies for entrepreneurs because it follows an idea from conception to initial funding, handling resulting lawsuits, and eventually becoming Facebook.

Key Takeaway: Everyone began small. To be successful, all you need to do is start taking small actions consistently, which will eventually lead to something big.

3. Becoming Warren Buffett (2017)

https://youtu.be/PB5krSvFAPY

This is a documentary film about Warren Buffet, a legendary investor with a net worth of more than $60,000,000,000.

Regardless, watching how he lives his life will undoubtedly touch your heart. Furthermore, this documentary depicted him beautifully as a husband, father, investor, and philanthropist.

The film will depict his humble lifestyle, including how he still lives in his modest home in Omaha and drives to the office every morning to manage his company.

It will show you how an ambitious, numbers-obsessed boy from Nebraska became one of the world’s richest and most respected men, the people who helped him along the way, and his unique mind, which will help you understand what is truly important when money no longer has meaning.

Key Takeaway: You can embrace principles of decency and integrity that will help you become a better version of yourself.

4. The Pursit of Happyness (2006)

This film depicts beautifully the financial insecurity of a common man, Chris Gardner.

He uses all of his savings to build bone density scanners, but they are too expensive to sell as an alternative to X-ray.

Fortunately, he is chosen as an intern at a brokerage firm; however, this does not please his wife, who leaves for a job in New York.

How broken Chris handles his son and everything with a smile will make you cry, but this film will also leave you with the strong message that no matter how bad things get, you should never give up.

Key Takeaway: One of the most important lessons this film teaches is that money cannot buy love or happiness.

5. The Big Short (2015)

This film tells three separate but loosely connected stories about the mortgage housing crisis in the United States.

Michael Burry is an eccentric hedge fund manager who discovers the insecurity and risk associated with the housing market in the United States.

To profit from this situation, he proposes creating a credit default swap market that would allow him to short the housing market.

Meanwhile, Jared Vennett comprehends Burry’s analysis and decides to enter the market in order to profit from the sale of swaps to firms.

Mark Baum, a hedge fund manager who recognizes how collateralized debt obligations (CDOs) have received AAA ratings, joins Burry and places a large bet – shorting the financial sector.

Finally, Charlie Geller and Jamie Shipley, two investors, invest in swaps. They initially make more money than Burry and Baum by shorting higher-rated AA mortgage securities, but later try and fail.

Burry ends up producing nearly 500% returns for investors who stick with him through the collapse of the housing market.

Key Takeaway: One of the most important lessons you can learn from this film is that you should never trust professionals without first doing your own research.

6. October Sky (1999)

This is an extraordinary story about a young boy who dreams of working in a local coal mine like his father. Everything changed in October 1957, when Sputnik, the first artificial satellite, was launched into orbit.

You will be inspired further by how this event inspired Homer Hickam, who went on to become a NASA engineer against his father’s wishes.

From small rockets to failures and experiments to winning the school science fair, participating in the National Science Fair in Indianapolis when everyone was against him would be a visual treat.

Key Takeaway: You must have one dream, work on it, and never give up until you achieve success.

7. Wall Street (1987)

This film’s plot revolves around Bud Fox, a junior stockbroker who aspires to work with Gordon Gekko, a legendary Wall Street player.

He tries everything he can to meet him, and eventually Gekko becomes his client.

Bud becomes wealthy, but soon realizes that Gekko’s plans will result in the layoff of the entire Bluestar staff.

He reveals everything to Wildman in secret and forces him to purchase a controlling interest in Bluestar at a significant discount.

Later, he assists legal authorities in building a case against Gekko in exchange for a reduced sentence.

Wildman will eventually offer him a job with Bluestar after he completes his prison sentence.

Key Takeaway: You will be taking two essential lessons from Wall Street. First, money never sleeps. Second, time is actually money.

8. Steve Jobs (2015)

It will take you behind the scenes of the digital revolution, through three iconic product launches, culminating with the introduction of the iMac in 1998.

This film will explain how the apparent failure of the Macintosh in 1984 prompted Jobs to establish a new company, NeXT.

You are moved by how he handled public criticism, being questioned about his contributions to computing history, and eventually becoming CEO of Apple in 1998.

Takeaway: Learn from your mistakes and keep moving forward.

9. Joy (2015)

She is an airline booking agent from a complicated family who is struggling financially.

Joy’s best friend encourages her to pursue her dream of creating an innovative self-wringing type mop.

From persuading a wealthy Italian to invest in her product to becoming a successful independent businesswoman, this is an excellent film for entrepreneurs to watch.

The most important lesson to take away from this film is that you can thrive even in the midst of chaos and dysfunction. All of this creates a frenetic energy to create something great from the ground up.

10. Something Ventured (2011)

This film follows the ups and downs of some of the twentieth century’s greatest companies, their hidden dramas, and the venture capitalists who backed and built them.

Interviews, archival photography, and footage of prominent venture capitalists and entrepreneurs from the 1960s, 1970s, and 1980s will also be available.

The key takeaway is that this film is full of passion, enthusiasm, and energy. It will motivate you to become an entrepreneur and teach you how to see opportunities where others do not.

11. Moneyball (2011)

The film begins with Billy Beane, general manager of the Oakland Athletics, attempting to assemble a competitive team for 2002 on a limited budget.

After the team’s loss to the New York Yankees in 2001, the majority of the current team’s star players plan to leave for free agency.

Brand, a recent Yale economics graduate, and Beane employ sabermetrics to identify and hire undervalued players.

It would be very inspiring and motivating to watch this team of undervalued players win 20 consecutive games and set a record.

Key Takeaways: The best entrepreneurial skill you can learn from this film is listening. Listening creates new opportunities. Nobody ever learned anything by listening to themselves speak.

12. Erin Brockovich (2000)

This film is about a bold and flashy woman who is a single mother and is trying to find work but is having no luck.

She forced her lawyer to give her a job as compensation for the loss after a failed lawsuit against a doctor in a car accident.

Her compensation job completely changed her life when her investigation into a real estate company turned into one of the largest class-action lawsuits in history against a multi-billion dollar corporation.

Key Takeaway: Have a clear vision of what you want to achieve, create a plan to make it happen, and then put forth an all-out effort to see it through.

This film follows Seth Davis, a 19-year-old college dropout who abandons his illegal casino and joins J.T. Marlin, a brokerage firm, in order to become wealthy.

He soon begins to make a good living. However, he gradually learns that this firm is a chop stock brokerage firm.

Later, he opens his own brokerage firm and sells shares by falsely claiming that the stock is guaranteed to rise in value.

He feels bad about defrauding people and intends to recoup enough money to assist J.T. Marlin’s victims. However, he is eventually apprehended by the FBI.

The FBI offers him federal immunity in exchange for testifying against J.T. Marlin, to which he agrees and assists the FBI in bringing strong evidence against him.

The most important lesson you can take away from this film is that a big life is not for everyone, and it is nothing to be ashamed of.

13. Start.com (2001)

https://youtu.be/ibuiUXOTE4M

This film is about two friends who, at the age of fifteen, dream of becoming wealthy by launching their own dot-com company.

They came up with the idea of an online revenue collection interface for municipal governments in their late twenties.

They were able to raise funds to turn their idea into a live product called GovWorks.com.

Unfortunately, this startup did not survive and went bankrupt, but I am confident that watching this startup film will inspire you to work on your own ideas.

Key Takeaway: This film teaches us that friends are not always good business partners, and if things do not go as planned, you may lose both the business and your friendship.

14. The Founder (2016)

This film depicts how Ray Kroc, a traveling milkshake machine salesman, suggests and persuades the two McDonald brothers, Maurice “Mac” and Richard “Dick,” to pursue the franchise business model.

Ray’s transformation from a failed attempt to build a McDonald’s restaurant in Des Plaines, Illinois, to a successful idea of franchising to middle-class investors is admirable.

He begins representing himself as the creator of McDonald’s and attempts to renegotiate his share of franchise profits, but the McDonald brothers decline.

Ray later incorporates a new company and opens new restaurants without the brothers’ permission, eventually forcing the brothers out of business.

The most important lesson of Persistence is taught in this film.

Furthermore, you can learn about the significance of legal documents.

The most important lesson of Persistence is taught in this film.

You can also learn about the significance of legal documents, brand building and protection, team selection.

15. The Commitments (1991)

The plot of this film follows the rise and fall of The Commitments, a Dublin Soul band.

How a young man with a clear vision brings together the right people for his band, puts in the work, and embraces the unknown and uncontrollable to keep the band together will have a profound impact on how you approach music, business, and life.

Key Takeaway: This film will teach you some valuable leadership lessons (Vision, authenticity, emotions, and ups and downs).

16. Jerry Maguire (1996)

This is the story of a sports agent who was fired by Sports Management International (SMI) after expressing his moral awakening.

Seeing how he tested his new philosophy with a single athlete and was humiliated in front of other athletes and sports agents will inspire you to work on your own ideas.

The most important lesson to take away from this film is that great things take time. So be patient and have faith in yourself.

17. The Aviator (2004)

This is an epic biopic of legendary director and aviation pioneer Howard Hughes, spanning the years from the late 1920s to the mid-1940s.

The film begins by depicting his early years as the owner of R.K.O. Pictures.

He has a long relationship with actress Katharine Hepburn, who assists him by caring for his deteriorating obsessive-compulsive disorder (OCD).

His main focus, however, was on designing and marketing new aircraft. From H-1 Racer test flights to breaking the world record to founding TWA as a competitor to Pan Am airlines, he demonstrates his passion for aviation and his drive for success.

The key takeaway is that with big risks come big rewards.

18. Glengarry Glen Ross (1992)

The plot of this film revolves around four con artists who sell parcels of land to uninterested and unable to afford real estate investment customers using leads purchased by their bosses.

When a salesman from downtown holds a sales meeting and reveals the Glengarry leads, the film takes an interesting turn.

Overall, this film will assist you in learning the AIDA (attention, interest, desire, and action) model, making it one of the best movies for entrepreneurs.

The most important thing you can learn from this film is to never put off until tomorrow what you can do today.

20. Pirates of  Silicon Valley (1999)

Pirates of Silicon Valley is an original made-for-television biographical drama film about Steve Jobs and Bill Gates, two legends who revolutionized the world.

This film depicts the rivalry between Apple Computer and Microsoft and how it influenced the development of the personal computer.

The film depicts a new deal struck between Apple and Microsoft at the 1997 Macworld Expo.

You will also be able to see flashbacks of Steve Jobs’ life on the U.C. Berkeley campus, Bill Gates (Anthony Michael Hall) at Harvard University, and how they developed Apple computers and the IBM-PC.

Key Takeaway: One of the best entrepreneurship lessons you can learn from The Pirates of Silicon Valley is to prioritize innovation as the company’s top priority.

21. Margin Call (2011)

The film begins with a typical business day at an investment bank but quickly takes a turn when the head of risk management discovers a major risk in the company’s finances.

This was followed by a long night of panicked senior management double-checking everything and preparing to do whatever it took to avert the disaster.

One of the most important lessons to take away from this film is that if you borrow to invest, you may end up owing more than you’re worth.

22. Forest Gump (1994)

This film is about Forrest Gump’s incredible and unexpected life journey.

He befriends a young lady named Jenny Curran.

The man who is frequently bullied because of his physical disability develops into an extremely fast runner.

He gets a football scholarship, joins the army, wins medals, motivates people to jog, discovers a talent for ping-pong, starts a shrimping business, and eventually becomes a millionaire.

Forest returns home to be with his mother as she succumbs to cancer.

During this visit, the journey from proposing Jenny to being heartbroken, then living the next three years in a relentless cross-country marathon, to reuniting with Jenny is undoubtedly a heartwarming story with a wholesome message.

Key Takeaway: If I had to pick one lesson to take away from this film, it would be this: Life is like a box of chocolates; you never know what you’re going to get. If you know, you know!

23. The Devil Wears Prada (2006)

Andy is a recent Northwestern University graduate and aspiring journalist.

She manages to land a job as a junior assistant to Miranda Priestly, the chief editor of a well-known fashion magazine, Runway.

She was initially unable to fit into the world of fashion and was humiliated for a long time.

It is one of the best inspiring movies for entrepreneurs to see how she learns the ropes in the world of fashion, outperforms her senior assistant, and becomes Miranda’s first choice.

Key Takeaway: This film sends a strong message that if you have the courage to become a better version of yourself, no one can stop you from succeeding.

24. The Wolf of Wall Street

The Wolf of Wall Street is based on Jordan Belfort’s true story. It follows his rise and fall as an entrepreneur, revealing how his firm, Stratton Oakmont, engaged in penny stock trading and securities fraud, attracting the FBI’s attention.

Martin Scorsese’s brilliant direction is complemented by stellar performances from Leonardo DiCaprio, Jonah Hill, Margot Robbie, and a spectacular cameo by Matthew McConaughey.

Jordan Belfort is the polar opposite of what an entrepreneur should be. He was motivated by greed, had little to no empathy for the people he duped, and led a life of extreme debauchery that eventually led to his downfall.

25. The Inventor: Out for Blood in Silicon Valley

The Inventor delves into the rise and fall of Theranos, a multibillion-dollar biotech company that was poised to revolutionize the healthcare industry. The documentary focuses primarily on Elizabeth Holmes, Theranos’ founder, and, to a lesser extent, the company’s COO Sunny Balwani.

The film depicts how Holmes and Balwani engaged in deceptive practices to mislead investors and business partners, and how both of them were more concerned with marketing, promotion, and fame than with getting their technology to work. They also spent the majority of their time intimidating and threatening former employees who had left the company due to Theranos’ deceptive practices.

Key Takeaway: Theranos’ meteoric rise and disastrous fall exemplifies the Silicon Valley valuation mindset. This should serve as a reminder to all of us to never be swayed by promises that appear too good to be true.