21 Movies Every Entrepreneur Should Watch for Inspiration

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21 Best Movies for EntrepreneursEntrepreneurs, like most people, need inspiration from time to time. And what better way to find inspiration than to take a break and watch some thought-provoking movies.

Regardless of where you currently stand on the entrepreneurial path, you’re sure to find some much-needed inspiration by watching the movies featured in this list.

Here are 21 inspiring movies every entrepreneur should watch.

21 Inspiring Movies for Entrepreneurs

1. The Social Network

Directed by David Fincher, The Social Network tells the story of how Mark Zuckerberg created Facebook while studying at Harvard and how he was later sued by two brothers who claimed he stole their idea, and his best friend who was ousted from the company.

Why watch it? It offers you a glimpse into how Facebook began and reminds you that big companies often have small beginnings. Aside from that, you have Aaron Sorkin’s brilliant script, David Fincher’s perfect direction, and a great ensemble cast.

Best Scene in the Movie: When Mark Zuckerberg meets Sean Parker for the first time.

2. Pirates of Silicon Valley

Based on the book Fire in the Valley: The Making of the Personal Computer, Pirates of Silicon Valley explores the rivalry between Steve Jobs and Bill Gates between 1971 – 1997. This movie came out in 1999, just when Steve Jobs began flourishing in his second innings at Apple. The movie ends with Bill Gates gaining the upper hand in the rivalry, but we all know what transpired next.

Why watch it? It offers a glimpse into the humble beginnings of two of the most iconic technology companies in the world and chronicles the rise of two men who totally transformed the world of technology.

Best Scene in the Movie: Steve Jobs interviews a prospective Apple employee.

3. Startup.com

If you want to learn more about the rise and fall of internet companies during the dotcom bubble, then Startup.com is the perfect movie. Startup.com is a documentary film that follows the story of GovWorks, a promising startup that failed spectacularly because of mismanagement and internal power struggles.

Why watch it? Aside from showing you the boom and bust of the dotcom bubble era, the documentary also tells you a cautionary tale of how friendships can turn into bitter rivalries because of internal politics. Massively underrated, it’s easily one of the best startup movies of all time.

Best Scene in the Movie: No clip stands out in particular, so I’d suggest you watch the movie to get the full scoop. Luckily, you can watch the whole movie on YouTube.

Related: 10 Best TV Shows for Entrepreneurs

4. Wall Street

This is the movie with the famous “Greed is good” speech, delivered by the charismatic Gordon Gekko played brilliantly by Michael Douglas, who won an academy award for his performance.

Directed by Oliver Stone, Wall Street tells the story of ambition and greed, portrayed brilliantly by Charlie Sheen and Michael Douglas respectively. The main protagonist, Bud Fox, idolizes Gekko and gets carried away by his glamorous lifestyle, only to get entangled in the vicious web of insider trading.

Why watch it? As young entrepreneurs, it’s often easy to be lured by greed and make morally reprehensible decisions. Wall Street serves as a cautionary tale of how ambition can sometimes lead us down an unethical path.

Word of advice: Skip the 2010 sequel starring Shia LaBeouf.

Best Scene in the Movie: The famous, or rather infamous, Gordon Gekko speech.

5. Glengarry Glenn Ross

A movie that stars Al Pacino, Kevin Spacey, Jack Lemmon, and Alec Baldwin (in a scene stealing cameo) should serve as motivation alone to watch this movie.

Glengarry Glenn Ross is based on an award-winning play which shows the plight of real estate salespeople during a tumultuous sales season.

Why watch it? The movie shows how it’s like to operate in a high pressure sales environment and how you need to use your wits in order to survive and thrive. Since its release, the movie has been used to train real life salesmen on how to sell and how not to sell.

Best Scene in the Movie: This ‘motivational’ speech by Alec Baldwin to the sales team. Enjoy!

6. The Big Short

Based on Michael Lewis’ book of the same title, The Big Short tells three separate but parallel stories of individuals who were able to predict and profit from the American financial crisis of 2007-08.

Directed by Adam McKay (best known for the Anchorman franchise prior to this movie), the movie features Oscar-worthy performances from Christian Bale and Steve Carell.

The film is also noted for employing unconventional techniques to explain complex and supposedly boring financial concepts like subprime mortgages and collateralized debt obligations (CDOs).

Why watch it? If you ever wanted to learn the real reasons behind the financial crisis of 2007-08 and not be bored to death at the same time, then you need to watch The Big Short.

While it serves as a cautionary tale for entrepreneurs, it also highlights the importance of risk-taking and conviction. Very few individuals would bet against the gigantic housing market at the time, but the characters in this movie (based on real people) do just that, despite facing mockery and ridicule from the entire financial community.

Best Scene in the Movie: Mark Baum (Steve Carell’s character) meets a shady CDO manager.

(Side note: The Big Short by Michael Lewis is one of my favorite business books of all time. If you liked the movie, I’d urge you to read the book as well. If you’re looking for more business books, check out this list of my 75+ favorite business books.)

7. The Wolf of Wall Street

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

Brilliantly directed by Martin Scorsese with stellar performances from Leonardo DiCaprio, Jonah Hill, Margot Robbie, and a spectacular cameo by Matthew McConaughey (right at the peak of his “McConaissance.”)

Why watch it? Jordan Belfort is the perfect example of what an entrepreneur shouldn’t be. He was driven by greed, having little to no empathy towards the people he was duping, and lived a life of extreme debauchery which eventually led to his downfall.

Best Scene in the Movie: Matthew McConaughey describes what it takes to be a stock broker.

(Interesting Trivia – The chest thumping and humming performed by McConaughey was improvised and actually a warm-up rite that he performs before shooting a scene.)

8. Boiler Room

If you can ignore the fact that Vin Diesel plays a smooth-talking stockbroker in the movie, you’re going to enjoy this. And if you enjoyed The Wolf of Wall Street, you’re going to enjoy Boiler Room even more as it is loosely based on Stratton Oakmont, the fraudulent stock trading company founded by Jordan Belfort.

The characters in the movie worship Gordon Gekko from Wall Street and make their living manipulating gullible people into buying penny stocks. You know exactly where this is headed!

Why watch it? Aside from exposing you to interesting cold-calling tactics, Boiler Room is ultimately a cautionary tale for young entrepreneurs to not be swayed by the lifestyle of the rich and famous to make morally questionable decisions.

Best Scene in the Movie: The Group Interview!

9. Fyre: The Greatest Party That Never Happened

Fyre festival was supposed to be the greatest music festival ever. Organized by Billy McFarland and rapper Ja Rule, the “luxury music festival” was promoted on Instagram by celebrities and social media influencers, including Kendall Jenner, Bella Hadid, and Emily Ratajkowski. The only problem? It was all a scam, devised by MacFarland who had a history of starting up fraudulent business ventures.

Netflix’s documentary Fyre: The Greatest Party That Never Happened gives us an exclusive behind-the-scenes look at the ill-fated music festival.

To grasp the scale of this fraud, you have to watch the documentary as it includes some shocking revelations from Billy’s unfortunate team members, the festival goers who were stranded on the island, and the heartbreaking tale of a Bahamian restaurateur who had to spend $50,000 of her own life savings to pay her staff who were preparing and serving meals to the stranded festival goers. Luckily, she created a GoFundMe page after the release of the documentary where she was able to recuperate the lost amount, thanks to the sympathy and generosity of people who were moved by her tale in the documentary.

Why watch it? Aside from being hilariously entertaining, it’s a cautionary tale for young entrepreneurs about making promises and not delivering a good product. Billy MacFarland was a dubious character who made misleading promises and misrepresented facts just to sell expensive tickets to an affluent audience. He had no experience, skills, or even the attitude to manage a music festival of this scale and magnitude.

The documentary also serves as a reminder for entrepreneurs who invest a huge amount of money in marketing and advertising without making any investment in improving the product. Fyre had great marketing, thanks to the enormous fan-base of the social media influencers, but the event itself was so mismanaged that it’s amazing MacFarland and Ja Rule thought they could get away duping their customers like this.

Best Scene in the Movie: That would be event producer Andy King’s shocking confession. King became a viral meme on Reddit and Twitter after the documentary. A clip of this on YouTube will probably be taken down because of copyright issues, so I’m not linking to it here. You’d need to watch the full movie on Netflix. In the meantime, watch the trailer below:

Side note: Around the same time this documentary was released on Netflix, Hulu released its own documentary on Fyre festival called Fyre Fraud. Although the Netflix documentary is better, Hulu’s Fyre Fraud features an interview with Billy MacFarland who does his best to dodge difficult questions in a totally cringeworthy manner.

10. The Aviator

Yet another Scorsese-DiCaprio collaboration in the list. The Aviator is a biopic of Howard Hughes, the eccentric billionaire who overcame all the odds to become a famous businessman and successful film director, while coping with his gradually worsening OCD. DiCaprio is brilliant in the movie and his performance earned him his second Oscar nomination. It’s also one of the best biography movies of all time.

Why watch it? Howard Hughes didn’t just compete with rival companies with deep pockets and movie moguls with powerful connections, but fought his own internal battle with a debilitating mental illness like OCD. Despite so many obstacles, he remained passionate about aviation and built a powerful legacy. He is the perfect role model for fledgling entrepreneurs who have to overcome numerous obstacles in life to achieve great things.

Best Scene in the Movie: The Senate Hearings!

11. Moneyball

A fan of baseball? No? Never mind! Moneyball has less to do with baseball and more to do with Oakland A’s GM Billy Beane’s unique tactics to overcome the odds stacked against his team.

Faced with limited budget, Billy Bean (Brad Pitt) decides to take the untested sabermetric approach towards building his team to achieve incredible results in the Major Baseball League (MLB).

Why watch it? Billy Bean had to adapt to survive. He knew Oakland A’s couldn’t compete with the big guns in the league because they didn’t have deep pockets. As such, he had to take risks and make tough decisions to achieve good results. Most startups face a similar scenario when they go up against stiff competition from established businesses in the market. Billy Beane’s success story at Oakland A’s shows that success can be achieved through risk-taking and inventiveness.

Best Scene in the Movie: Billy Beane describes the problem at Oakland A’s.

12. The Founder

The Founder is a biopic of the American fast-food tycoon Ray Kroc. Starring Michael Keaton, the movie tells the story of his creation of McDonald’s fast-food restaurant chain, which became the biggest restaurant business in the world. It also stars Nick Offerman and John Carroll Lynch who play the McDonald brothers, the original founders of McDonald’s.

Why watch it? Despite being a controversial figure, Ray Kroc’s story is an inspiring one for entrepreneurs. He was a travelling milkshake mixer salesman who eventually transformed McDonald’s into a global franchise, making it the most successful fast food company in the world. It’s the biopic that narrates the rise of one of America’s most influential businessmen and perhaps the most recoginizable fast food brands in the world. At the same time, you feel for the original founders of McDonald’s, the McDonald brothers, who were dealt a bad hand and eventually forced out of business.

Best Scene in the Movie: Ray Kroc orders a meal at McDonald’s for the first time.

13. Margin Call

Yet another movie about the 2007-08 financial crisis, but this time it’s from the perspective of an investment bank deep in the crisis. The plot of Margin Call revolves around key people in a large investment bank and the actions they take over a 24-hour period during the initial stages of the financial crisis.

Although the fictional investment bank has no name in the movie, many believe the actions taken by the firm are too similar to the ones taken by Goldman Sachs and Merrill Lynch during the crisis.

Why watch it? Greed is never good, despite what Gordon Gekko says. Entrepreneurs must remember this at all times. Margin Call tells the story of a corporation that is steeped in greed and dishonesty. Like Wall Street and The Big Short, this movie is also a cautionary tale about the corruptive power of greed.

Best Scene in the Movie: Emergency meeting with the senior partners at the bank.

14. Steve Jobs

Not the one starring Ashton Kutcher, but the one with Michael Fassbender playing the iconic Apple co-founder. Directed by Danny Boyle and written by Aaron Sorkin (who also wrote The Social Network), Steve Jobs is a different sort of a biopic. It contains just 3 sequences, all depicting a pivotal point in Jobs’ life. The movie includes brilliant performances by Fassbender and Kate Winslet.

Why watch it? Though it was not as critically acclaimed as the studio hoped it would be, it’s still the best Steve Jobs biopic there is. If you don’t have the time to read Walter Isaacson brilliant Steve Jobs’ biography, watch this movie.

Best Scene in the Movie: Steve Jobs confronts John Sculley, the person responsible for getting him fired from the company he co-founded.

15. Thank You for Smoking

Want to master the art of marketing or selling just about any product? Then Thank You for Smoking is the movie you need to watch. The plot of the movie revolves around the machinations of Big Tobacco’s chief spokesman, Nick Naylor, who defends the cigarette industry in challenging situations.

Why watch it? Selling is an essential aspect of entrepreneurship and this movie teaches you that it’s possible to sell anything as long as you have data and persuasiveness to woo your audience.

Best Scene in the Movie: Nick Naylor (Aaron Eckhart) shows off his spin skills on Joan Lunden’s talk show.

16. The Pursuit of Happyness

The Pursuit of Happyness is a true story based on the life of entrepreneur Chris Gardner’s nearly one-year struggle of being homeless with his son while going through a gruelling 6-month unpaid internship as a stockbroker. Will Smith’s portrayal of Gardner earned him an Oscar nomination.

Why watch it? Chris Gardner overcame unbelievable circumstances to achieve his dreams. Circumstances that are not much different from what early-stage entrepreneurs face.

Best Scene in the Movie: After months of struggle, Chris Gardner is finally hired by Dean Witter Reynolds.

17. Enron: The Smartest Guys in the Room

Enron: The Smartest Guys in the Room is a documentary based on the best-selling book of the same name by Bethany McLean and Peter Elkind (the book is featured in my list of 75+ best books for entrepreneurs.)

The documentary examines the fall of Enron Corporation in 2001 and all the key players who were responsible for what came to be known as the Enron scandal. The film features interviews with the authors McLean and Elkind, as well as former Enron executives and employees, stock analysts, reporters, and the former Governor of California Gray Davis.

Why watch it? The story of Enron is the ultimate tale of greed and corruption. As such, it can provide key lessons to entrepreneurs and business leaders of the consequences of greed. From using faulty accounting practices to hiring unscrupulous characters in key roles, the top executives at Enron were driven solely by greed and profits, and as a result, did everything in their power to deceive the stakeholders and the general public until it all collapsed like a house of cards.

Best Scene in the Movie: No particular scene stands out, so I’d urge you to check out the documentary. You can watch the full movie on YouTube.

18. Any Given Sunday

Directed by Oliver Stone and featuring a great ensemble cast, including Al Pacino, Jamie Foxx, Cameron Diaz, Dennis Quaid, and LL Cool J, Any Given Sunday offers a behind-the-scenes look at the struggles of a fictional professional American football team.

Al Pacino plays a veteran coach who is facing the heat after having fallen out of favor with the team owner Christina Pagniacci (Cameron Diaz). This movie is a must-watch not just for Pacino fans, but also for budding entrepreneurs and sports enthusiasts.

Why watch it? I’d recommend this movie to entrepreneurs for the sheer grit and intensity shown by Al Pacino’s character in the face of adversity. He’s not just having a face-off with the unrelenting owners, but also trying to subvert a revolt from an emerging star within his team. But in the end, he overcomes all these challenges because of his inner strength and willpower to succeed.

Best Scene in the Movie: This epic speech by Al Pacino (Tony D’Amato) to his team before the start of a crucial playoff game.

19. The Inventor: Out for Blood in Silicon Valley

Ever since I read Bad Blood by John Carreyrou, I have been fascinated with Theranos and its enigmatic founder Elizabeth Holmes.

The Inventor examines the rise and fall of Theranos, a multibillion dollar biotech company that was set to transform the healthcare industry. The documentary mainly revolves around Elizabeth Holmes, the founder of Theranos, and to some extent, the company’s COO Sunny Balwani.

The film chronicles how Holmes and Balwani engaged in fraudulent practices to mislead investors and business partners, and how both of them were more interested in marketing, promotion, and fame than in getting the actual mechanics of their technology working. They also spent most of their time intimidating and threatening former employees who had quit the company because of the deceptive practices followed by Theranos.

Why watch it? Theranos’ meteoric rise and catastrophic fall exemplifies the Silicon Valley attitude towards valuation. This should serve as a reminder to all of us to never get carried away by promises that sound too good to be true.

To tell the truth, I was a bit underwhelmed by the documentary as it’s not as compelling as Carreyrou’s book Bad Blood, which goes into greater detail into what transpired at Theranos. That said, the documentary presents a good overview of the Theranos scandal. But if you’d like to learn more about the scandal, I’d highly recommend you read Carreyrou’s book Bad Blood.

Best Scene in the Movie: Nothing stands out in particular. You’ll need to watch the documentary on HBO, and if you live in India, you can watch it on Hotstar. In the meantime, you can watch the trailer below:

20. The Great Hack

One of the most shocking scandals in 2018 was the Facebook–Cambridge Analytica data scandal, where it was revealed that Cambridge Analytica, a British political consulting firm, had harvested the personal data of millions of Facebook users without their consent and used it for political advertising purpose, including Brexit and Donald Trump’s 2016 presidential campaign.

The Great Hack is a documentary film which examines the Cambridge Analytica scandal through the eyes of people who were involved in it.

Why watch it? It reveals the extent to which our personal data is harvested by Facebook for advertising purposes. We all knew Facebook was mining our private data, but The Great Hack reveals the extent to which our privacy is violated by Facebook. And the sad part is this: Facebook got away doing this with just a slap on the wrist. As Scott Galloway writes in his book The Four, “Facebook has been weaponized; our faux outrage hasn’t translated to any tangible action, and it’s going to get worse.”

Best Scene in the Movie: No clips on YouTube that I can link to, so you’ll need to watch the movie on Netflix. In the meantime, you can watch the trailer below:

21. Becoming Warren Buffett

Becoming Warren Buffett is a documentary film about Warren Buffett and his life. The documentary examines the contrast between Warren Buffett’s expertise in investing and his personal relationship skills.

Why watch it? If young entrepreneurs can look up to just one role model for inspiration, it would have to be Warren Buffet. Warren Buffet is known for his business and investing acumen. But more importantly, his down-to-earth nature make him one of the most admirable people to look up to. If you wanted to learn the secrets behind Buffet’s success, this is a must-watch documentary.

Best Scene in the Movie: Once again, I’d urge you to check out the full documentary, which you can watch on YouTube below:

Final Thoughts

If you’re ever in need of inspiration or would just like to take a break from your hectic work schedule, watch or rewatch these movies. You’ll not be disappointed.

Did I miss any of the best entrepreneur movies that you consider must-watch? Let me know in the comments section below.

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Editor’s Note: This article was first published on July 26, 2017 and has been updated regularly since then for relevance and comprehensiveness. 7 additional movies were added to the list on November 4, 2019.

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3 COMMENTS

  1. “The Pursuit of Happyness” is a wonderful movie!!! Entrepreneur or not, it should definitely be on everyone’s list of movies to watch!

  2. I Think Acrimony is missing, TV Shows like Suits, Billions, Silicon valley should all be added. Silicon Valley is my favorites as it shows how tech guys do strive to make it. It is not what people think. that if you are into tech you will make it ASAP

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