14 Movies Every Entrepreneur Should Watch for Inspiration


14 Movies Every Entrepreneur Should Watch for InspirationEntrepreneurs, 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 14 inspiring movies every entrepreneur should watch.

Top 14 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 of 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 was flourishing in his second innings at Apple.

Why watch it? It offers a glimpse into the humble beginnings of two of the most successful technology companies in the world.

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. The only documentary in this list, Startup.com 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.

Best Scene in the Movie: Watch the whole movie on YouTube (seriously!).

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4. Wall Street

This is the movie with the famous speech “Greed is good”, delivered by the charismatic Gordon Gekko played brilliantly by Michael Douglas.

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 William 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 how to sell and how not to sell.

Best Scene in the Movie: This ‘motivational’ speech by 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 79 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.

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 stock-broker 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 mortally questionable decisions.

Best Scene in the Movie: The Group Interview!

9. 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 this movie and his performance earned him his second Oscar nomination.

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!

10. 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.

11. 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 Golden 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.

12. 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 Steve Jobs’ biography, watch this movie.

Best Scene in the Movie: Jobs confronts Sculley.

13. 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.

14. 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: Chris Gardner is hired!

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 movies that you think are must-watch for entrepreneurs? 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.

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  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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