Like most people, entrepreneurs need inspiration from time to time. You can find inspiration by taking a break to watch thought-provoking movies. Here are 21 Best Entrepreneur Movies Every Entrepreneur Should Watch for Inspiration.
I am struck by how inspirational movies transcend genres and styles when I reflect on the best. Some are dramatic, while others are action-packed and fast-paced.
Yet, they all have one thing in common: their ability to evoke strong emotions in me. Check out my list to find the best inspirational movies.
Great inspirational movies are my favourite. I’m transported to another time and place for 90 minutes and am invited into the lives of many wonderful, endearing characters.
I am completely absorbed in their world for that time and forget everything else. These strangers are allowed to delight, captivate, intrigue, thrill, scare, excite and delight my eyes in the big black box.
21 Best Entrepreneur Movies
They have my permission to touch my heart, yank at me and reach into my soul. Whether you are on your entrepreneurial journey, these movies will inspire you.
#1. The Social Network
David Fincher directs the Social Network. It tells the story about Mark Zuckerberg’s creation of Facebook while at Harvard.
Two brothers later sued him for stealing their idea and his best friend, who was fired from the company.
What’s the point? This video gives you a glimpse at how Facebook started and reminds us that even big companies could have humble beginnings.
Apart from that, Aaron Sorkin’s amazing script, David Fincher’s flawless direction, and an ensemble cast are all highlights.
The Best Scene from the Movie: Mark Zuckerberg meets Sean Parker.
#2. Pirates of Silicon Valley
Based on the book Fire in the Valley, The Making of the Personal Computer examines the rivalry of Steve Jobs and Bill Gates from 1971 to 1997.
This movie was released in 1999, as Steve Jobs started to prosper in his second Apple innings. Of course, we all know the movie’s outcome, which ends with Bill Gates winning the rivalry.
What’s the point? It gives a glimpse at the humble beginnings and the rise of two men that have revolutionized the technology world.
The Best Scene in the Movie: Steve Jobs interviewing a potential Apple employee.
#3. Startup.com
Startup.com will help you learn more about the rise of internet companies in the dotcom bubble. Startup.com tells the story of govWorks, a promising startup that fell apart due to poor management and internal power struggles.
Why should you watch it? The documentary shows you how the dotcom bubble and bust can affect friendships. It’s a great startup movie that is often overlooked.
The Best Scene from the Movie: No one clip stands out, so I recommend you to watch the entire movie. You can view the entire movie on YouTube.
#4. Wall Street
This is the film with the famous “Greed is good!” speech. It was delivered by Gordon Gekko, played brilliantly by Michael Douglas, who won an Academy Award for his performance.
Oliver Stone directs Wall Street, which tells the story about ambition and greed. It is brilliantly portrayed by Charlie Sheen, Michael Douglas, and Michael Moore.
Bud Fox, the main character, falls in love with Gekko and becomes entangled in the vicious web of insider trading.
What’s the point? Young entrepreneurs are often easily enticed by greed and make morally questionable decisions. Wall Street is a cautionary tale about how ambition can lead to unethical decisions.
A word of advice: Skip to the sequel featuring Shia LaBeouf in 2010. Best Scene from the Movie: The famous or more infamous Gordon Gekko speech.
#5. Glengarry Glenn Ross
This movie stars Al Pacino, Jack Lemmon, and Alec Baldwin in a scene-stealing cameo. Glengarry Glenn Ross was based on an award-winning play that depicts the misery of real estate agents during a turbulent sales season.
Why should you watch it? The movie shows what it’s like working in high-pressure sales environments and how to make it work. The movie has been used to teach real-life salespeople how to sell.
The Best Scene from the Movie: Alec Baldwin’s motivational speech to the sales team. Enjoy!
#6. The Big Short
Michael Lewis’Lewis’ book has the same title. The Long Short tells three distinct but related stories about individuals who were able to predict and profit from the 2007-08 financial crisis.
Adam McKay, best known for his Anchorman franchise, directed the movie. The movie also features Oscar-worthy performances by Christian Bale (and Steve Carell).
It is also notable for its unconventional approach to explaining complex but supposedly boring financial concepts such as subprime mortgages or collateralized debt obligations.
What’s the point? It would be best if you saw The Great Short understand the true reasons for the financial crisis in 2007-08.
It serves as a warning to entrepreneurs and highlights the importance and risk-taking of conviction.
Although few people would have placed a bet against the massive housing market of the time, the actors in the movie (based on real people) do so despite being mocked and ridiculed by the entire financial community.
The Best Scene in the Movie: Mark Baum (Steve Carell’sCarell’s character) meets an obnoxious CDO manager.
Side Note: The Big Short, by Michael Lewis, is one of my all-time favorite business books. I recommend the book to anyone who enjoyed the movie.
#7. The Wolf of Wall Street
The Wolf of Wall Street was based on the real story of Jordan Belfort. It shows his rise and fall as an entrepreneur and how his firm Stratton Oakmont engaged with penny stock trading and securities fraud, drawing the FBI’s attention.
Martin Scorsese’s brilliantly directed film features stellar performances by Jonah Hill, Leonardo DiCaprio and Margot Robbie. A spectacular appearance by Matthew McConaughey is also included (right at the height of his ” McConaissance.
What’s the point? Jordan Belfort shows us what an entrepreneur should not be. He was driven only by greed and had little or no empathy for the people he was ripping off. His downfall was inevitable.
The Best Scene in the Movie: Matthew McConaughey explains what it takes to become a stockbroker.
Interesting Trivia The chest-thumping, humming and shaking McConaughey performs before he shoots a scene.
#8. Boiler Room
You won’t be disappointed if Vin Diesel plays a smooth-talking stockbroker. Boiler Room is a loosely based movie on Stratton Oakmont (a fraudulent stock trading company that Jordan Belfort founded).
The movie’s characters worship Gordon Gekko of Wall Street and make their living by manipulating people into buying penny stocks. Unfortunately, this is exactly where it’s headed!
Why should you watch it? Apart from showing you interesting cold-calling techniques, Boiler Room serves as a warning to young entrepreneurs not to be influenced by the lifestyles of the wealthy and famous for making morally dubious decisions.
#9. Fyre: The Greatest Party That Never Happened
Fyre Festival was billed as the best music festival. The “luxury music festival,” organized by Billy McFarland, Ja Rule and other celebrities, was promoted on Instagram by social media influencers such as Bella Hadid and Emily Ratajkowski.
MacFarland, who has a history of creating fraudulent business ventures, concocted the scam.
Netflix’s documentary Fyre: The Greatest Partie That Never Happened offers a behind-the-scenes look at the tragic music festival.
You have to see the documentary to understand the extent of the fraud.
It includes shocking revelations from Billy and his team, festival-goers left on the island and the heartbreaking story of a Bahamian restaurateur, who spent $50,000 of her life savings to pay her staff, who prepared and served festival-goers meals.
After the documentary’s release, she set up a GoFundMe page where she was able to recover the amount lost. This was thanks to the kindness and generosity of those who saw her story.
Why should you watch it? It’s hilarious and warning young entrepreneurs about promising but not delivering on their promises.
Billy MacFarland was a fraudster who misrepresented facts and made false promises to sell tickets to a wealthy audience.
But, unfortunately, he didn’t have the skills or attitude needed to manage this large and complex festival.
This documentary reminds entrepreneurs that they can spend a lot of money on marketing and advertising, but not on the product.
Fyre was able to market their product well thanks to the huge fan base of social media influencers.
However, who so poorly managed the event itself that Ja Rule and MacFarland thought they could get away with deceiving their customers.
The Best Scene in the Movie: This would be Andy King, an event producer’s shocking confession. After the documentary, King was a popular meme on Reddit and Twitter.
Unfortunately, copyright issues will likely cause a YouTube clip of this to be removed. So I won’t link to it here. To see the entire movie, you’d have to go to Netflix. You can watch the trailer below.
Side Note: Hulu also released a documentary about Fyre Festival called Fyrefraud. The Netflix documentary is superior, but Hulu’s Fyre Fraudfeatures an interview with Billy MacFarland.
He does his best to avoid difficult questions in a completelycringe-worthyy way.
#10. The Aviator
Another Scorsese/DiCaprio collaboration is on the list. The Aviator tells the story of Howard Hughes, an eccentric billionaire who overcame all odds to become a successful businessman and film director while also struggling with his OCD.
DiCaprio’s performance in the movie is outstanding and earned him his second Oscar nomination. It is also one of the most important biography films of all time.
It’s worth it. Howard Hughes did not compete with movie moguls and companies with large pockets but also faced his internal struggle with OCD, a crippling mental illness.
Yet, he persevered despite many challenges and left a lasting legacy. He is a great role model for entrepreneurs who must overcome many obstacles to succeed.
#11. Moneyball
Are you a fan of baseball? No? No!
With a limited budget, Billy Bean (Brad Pitt) decides to use the untested sabermetric method to build his team and achieve amazing results in the Major Baseball League.
Why should you watch it? Billy Bean needed to adapt to survive. Because they didn’t have the deep pockets to compete, he knew the Oakland A’s could not be competitive with the other big players in the league.
So he had to take risks and make difficult decisions to get good results. Startups often face similar challenges when competing with established companies in the market.
The success story of Billy Beane at Oakland A’s demonstrates that risk-taking and creativity can lead to success.
The Best Scene in the Movie: Billy Beane explains the problem at Oakland A’s.
#12. The Founder
The founder is an American biopic about Ray Kroc, a fast-food tycoon. The movie stars Michael Keaton and tells the story of Ray Kroc’s creation of McDonald’s, the largest restaurant company globally.
John Carroll Lynch and Nick Offerman play the McDonald’s brothers, also featured in the movie.
Why should you watch it? Although Ray Kroc is a controversial figure, his story can be a great inspiration for entrepreneurs.
He was a traveling milkshake mixer salesman that transformed McDonald’s into a global chain, becoming the largest fast-food franchise in the world.
This biopic tells the story of the rise of America’s most prominent businessmen and one of the most recognized fast-food brands.
But, unfortunately, you also feel sorry for the McDonald’s brothers, who suffered a terrible start and were eventually forced to leave the company.
The Best Scene in the Movie: Ray Kroc orders his first meal at McDonald’s.
#13. Margin Call
Another movie about the financial crisis of 2007-08. This time, however, it is from the point of view of an investment bank that was caught up in the crisis.
The margin call is a story about key figures in an investment bank and their actions over 24 hours during the financial crisis’s initial stages.
Although the film doesn’t give the name of the fictional investment bank, many people believe that their actions are too similar to those taken by Merrill Lynch and Goldman Sachs during the crisis.
It’s not worth it. Contrary to what Gordon Gekko claims, greed is not good. This is something entrepreneurs must always remember. The margin call is the story of a company that is rife with greed and dishonesty.
Like Wall Street or The Big Short, this movie is a cautionary tale about greed’s corruptive power.
The Best Scene from the Movie: An emergency meeting with senior bank partners.
#14. Steve Jobs
The one that stars Ashton Kutcher is not the one with Michael Fassbender as the legendary Apple co-founder. Danny Boyle directed the film, Steve Jobs.
It was written by Aaron Sorkin, who also wrote the Social Network. The movie comprises three sequences that each depict a key moment in Jobs’ life. Fassbender, Kate Winslet and other actors give outstanding performances.
What’s the point? Although it wasn’t as well-received as the studio had hoped, it is still the best Steve Jobs biopic.
This movie is a great alternative to reading Walter Isaacson’s brilliant biography about Steve Jobs.
The Best Scene in the Movie: Steve Jobs meets John Sculley. He is the one responsible for his firing from the company he founded.
#15. Thank You for Smoking
Do you want to learn how to market and sell any product? Then, thank you for Smoking will teach you how to market and sell any product.
The movie’s plot revolves around Nick Naylor, Big Tobacco’s chief spokesperson, who defends Big Tobacco in difficult situations.
Why should you watch it? Selling an idea is an important aspect of entrepreneurship. This movie shows you how to convince your audience with data and persuasiveness.
Best Scene from the Movie: Nick Naylor (Aaron Eckhart) shows off his spin skills during Joan Lunden’s talk show.
#16. The Pursuit of Happyness
The Pursuit Of Happiness is a true story that focuses on Chris Gardner, an entrepreneur who lived almost a year homeless with his son and went through a 6-month unpaid internship at a stockbroker.
Will Smith was nominated for an Oscar for his portrayal of Gardner.
What’s the point? Chris Gardner overcomes unbelievable circumstances to realize his dreams.
Unfortunately, these are the same circumstances that early-stage entrepreneurs have to face.
Best Scene from the Movie: After months of struggle Chris Gardner is finally hired and promoted by Dean Witter Reynolds.
#17. Enron: The Smartest Guys in the Room
Enron: The Smartest Guys In the Room is an animated documentary based on the best-selling book by Bethany McLean.
This documentary examines the 2001 fall of Enron Corporation and the key figures involved in the Enron scandal.
Interviews with McLean, Elkind, former Enron employees and stock analysts, reporters, governor of California Gray Davis, and other key players are included in the film.
Why should you watch it? Enron’s story is the ultimate tale about greed and corruption. It can be a powerful lesson for business leaders and entrepreneurs about the dangers of greed.
Enron’s top executives were driven by greed and profit. They used faulty accounting practices and hired unscrupulous people to key positions. It was a deceitful house.
The Best Scene from the Movie: No one scene stands out, so I recommend checking out the documentary. Who can view the entire movie on YouTube?
#18. Any Given Sunday
Any Given Sunday is directed by Oliver Stone. It features a great ensemble cast that includes Al Pacino and Jamie Foxx and Dennis Quaid and Dennis Diaz.
Al Pacino portrays a retired coach who finds himself in hot water after falling out with Christina Pagniacci (Cameron Diaz). This film is not only for Pacino lovers but for all budding entrepreneurs and sports fans.
Why should you watch it? Entrepreneurs will love Al Pacino’s determination and determination in facing adversity. He has to face off with his unrelenting owners, but he’s also trying to subvert the rebellion from an emerging star in his team.
He overcomes these obstacles because of his inner strength, willpower and determination to succeed.
The Best Scene in the Movie: Al Pacino (Tony D’Amato) gives this speech to his team just before starting a crucial playoff match.
#19. The Inventor: Out for Blood in Silicon Valley
Since I first read Bad Blood, John Carreyrou’s book, I have been fascinated by Theranos and Elizabeth Holmes, its mysterious founder.
The Inventor explores Theranos’ rise and fall. Who created this multibillion-dollar biotech company to transform healthcare.
The documentary is primarily about Elizabeth Holmes, who founded Theranos and, to a certain extent, Sunny Balwani, the company’s chief operating officer.
The film shows how Holmes and Balwani used fraudulent tactics to mislead investors. It also shows how they were more interested in marketing, promotion and fame than the actual technology.
In addition, ex-employees who quit Theranos’ company due to their deceptive practices were also intimidated and threatened by them.
Why should you watch it? Theranos’ meteoric rise and subsequent catastrophic fall is a perfect example of Silicon Valley’s attitude to valuation.
We should all take this as a warning to not let ourselves be deceived by promises that seem too good to be true.
The documentary was not as captivating as Carreyrou’s book Bad Blood which provides more detail about what happened at Theranos.
However, the documentary gives a good overview of the Theranos scandal. If you want to know more about the scandal, I recommend Carreyrou’s book Bad Blood.
The Best Scene from the Movie: There isn’t one standout moment. Who can view the documentary on HBO or Hotstar if you are in India? You can watch the documentary on HBO while you wait.
#20. The Great Hack
The Facebook-Cambridge Analytica Data Scandal was one of the most scandalous in 2018 first revealed that Cambridge Analytica (a British political consulting company) had illegally harvested personal data from millions of Facebook users and used them for political advertising purposes, including Donald Trump’s 2016 presidential campaign.
The Great Hack is a documentary that shows the scandal at Cambridge Analytica through the eyes and experiences of those involved.
Why should you watch it? It shows how much personal data Facebook has taken from us for advertising purposes.
While we all knew Facebook was collecting our private data, The Great hack shows how Facebook violates our privacy.
The sad thing is that Facebook could get away with this without even being criticized. Scott Galloway wrote in his book The Four that Facebook has been weaponized.
Unfortunately, our faux outrage hasn’t translated into any tangible action, and it’s only going to worsen.
Best Scene from the Movie: I don’t have any clips that I can link, so you need to watch it on Netflix.
#21. Becoming Warren Buffett
Becoming Warren Buffett is a documentary about Warren Buffett’s life. This documentary examines the differences between Warren Buffett’s investment expertise and his personal relationships skills.
Why should you watch it? Warren Buffet is the role model young entrepreneurs need to look up to for inspiration. Warren Buffet is well-known for his investment and business acumen.
However, his down-to-earth personality makes him an admirable person to look up to. This documentary is essential viewing if you want to discover the secrets of Buffet’s success.
The Best Scene in the Movie: I urge you to watch the entire documentary on YouTube again.
Final Thoughts
These movies are great for inspiration and relaxation. You won’t be disappointed. Are there any entrepreneur movies I missed? Comment below to let me know.
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