15 Movies Every Entrepreneur Must Watch

Entrepreneurs aren’t known for having a lot of downtime. But sometimes, all of us just want to relax on the sofa with a movie.

So we’ve picked our fifteen all-time favorite movies for entrepreneurs – movies with messages, warnings… and great storylines as well!

Entrepreneurs can find inspiration from these entertaining and thought-provoking titles.

1. Wall Street (1987)

Who could forget Michael Douglas as Gordon Gecko and his famous ‘greed is good’ speech? This movie follows the fortunes of young stockbroker Bud Fox, played by Charlie Sheen, as he entices Gecko into mentoring him by providing insider information. Bud is embroiled in greed and underhanded schemes, eventually threatening the livelihood of his honest father.

Why should entrepreneurs watch it? As eager entrepreneurs, it may seem easy to be lured by the promises of fast money and greed. Oliver Stone’s Wall Street is a cautionary tale about not putting ambition before ethics.

2. Glengarry Glen Ross (1992)

From a screenplay by David Mamet, the machinations behind the scenes at a real estate office during a turbulent sales season are examined, with Alec Baldwin giving an award-winning performance.

Why should entrepreneurs watch it? The movie shows a high-pressure sales environment and what you might need to do to survive and thrive. Since its release, it has been used in real life to train salesmen how to sell.

3. Jerry Maguire (1996)

“Show me the money!” When a sports agent writes an ill-received memo and is fired, he decides to open his own agency to test his new philosophy.

Why should entrepreneurs watch it? It is packed with practical advice for when you launch a startup – and gives examples of pitfalls too.

4. Pirates of Silicon Valley (1999)

A semi-humorous film about the men that made the world of technology what it is today. Noah Wylie as Steve Jobs and Anthony Michael Hall as Bill Gates struggle through college, founding their companies and taking ingenious action to build up the global empires of Apple and Microsoft.

Why should entrepreneurs watch it? To take heart from the humble beginnings of even the biggest of players.

5. Rogue Trader (1999)

Nick Leeson is an ambitious investment broker who takes every opportunity he is given by the enormous Barings Bank. He single-handedly manages to bankrupt this, one of Britain’s largest banks through illegal trades and covering up losses.

Why should entrepreneurs watch it? It shows how money can drive all sorts of behaviors and shows that accumulating power and money does not make a person indispensable.

6. Boiler Room (2000)

Giovanni Ribisi stars as Seth Davis, a college dropout trying to win back his father’s approval. He takes a position as a trainee stockbroker at JT Marlin, but soon begins to question the legitimacy of the firm.

Why should entrepreneurs watch it? Interesting cold calling tactics abound, but the film is ultimately a cautionary tale for entrepreneurs not to be swayed from making morally sound decisions.

7. Startup.com (2001)

This documentary examines the rise and fall of real-life startup GovWorks, a startup with a promising future that raised $60 million from multiple sources, then imploded from mismanagement and internal power struggles.

Why should entrepreneurs watch it? Capital growth techniques, team building and management skills are touched on, but the film also cautions prudence when entering business with friends.

You can watch the full documentary on YouTube here.

8. Catch Me If You Can (2002)

Tom Hanks as FBI agent Carl Hanratty and Leonardo DiCaprio as Frank Abagnale Jr. are brilliant in this Steven Spielberg movie about a nineteen-year-old man who successfully forges millions of dollars worth of checks while masquerading as a pilot, a doctor and a legal prosecutor.

Why should entrepreneurs watch it? See Frank Abagnale Jr. use all six of Robert Cialdini’s psychological principles of influence – reciprocity, commitment and consistency, liking, social proof, authority and scarcity. Good marketers use these principles every day.

9. The Aviator (2004)

Directed by Martin Scorsese, this film depicts the early days of legendary director and aviator Howard Hughes’ career from the late 1920’s to the mid 1940’s. The Senate hearing scenes are particularly good and once again, Leonardo DiCaprio gives a great performance as Howard Hughes, with Cate Blanchett and Kate Beckinsale providing his love interests in the forms of Katharine Hepburn and Ava Gardner.

Why should entrepreneurs watch it? Howard Hughes succeeded despite serious mental illness, germophobic and obsessive-compulsive. He is a role model for entrepreneurs to succeed even when the physical odds seem to be against you.

10. Lord of War (2005)

An arms dealer (Nicholas Cage) is confronted by the morality of his work as he is being chased by an Interpol agent. The film charts the rise and fall of Yuri Orlov who starts in the early 1980’s selling guns to mobsters in his local neighborhood through to the early 1990’s when he forms a partnership with an African warlord and his psychotic son.

Why should entrepreneurs watch it? Despite Orlov’s dubious morality, his qualities of ambition, tenacity and the ability to tolerate risk demonstrate the things entrepreneurs need to succeed.

11. Thank You For Smoking (2005)

This satirical comedy follows the machinations of Nick Naylor, played by Aaron Eckhart, the spokesman for Big Tobacco, who spins on behalf of cigarettes while still trying to remain a role model for his pre-teen son.

Why should entrepreneurs watch it? This movie teaches you that it is possible to sell anything as long as you have the data to back yourself up, and the persuasiveness to woo your audience.

12. The Pursuit of Happyness (2006)

No list of entrepreneurial movies would be complete without Chris Gardner’s story of triumph over tribulation. Gardner completes an unpaid internship with a stockbroker even as he tries to sell a device he has invested heavily in that doesn’t sell as well as expected, and takes care of his son while also being homeless.

Why should entrepreneurs watch it? Triumphing over adversity, Chris Gardner overcame unbelievable odds to achieve his dreams – but it’s not that different from what most fledgling entrepreneurs face.

13. The Devil Wears Prada (2006)

A smart, sensible graduate (Anne Hathaway)  lands a job as an assistant to Miranda Priestly (Meryl Streep), editor-in-chief of a high fashion magazine, and receives quite a few on the job lessons in hard negotiation and hard choices.

Why should entrepreneurs watch it? The movie will encourage you to take the plunge and chase your dream job, as well as teaching you about the cut-throat world of high fashion.

14. The Social Network (2010)

This film charts the rise of Mark Zuckerberg and how he invented the global phenomenon that would become Facebook while studying at Harvard. But for Zuckerberg, success leads to personal and legal complications when two brothers who claim he stole their idea sue him, along with his friend and co-founder who was squeezed out of the business.

Why should entrepreneurs watch it? Take heart from the fact that enormous companies often have small beginnings.

15. The Wolf of Wall Street (2013)

Based on the true story of Jordan Belfort, the movie follows his rise from wealthy stockbroker to his fall involving crime, corruption and the federal government as his firm, Stratton Oakmont is found to have engaged in penny stock trading and securities scams.

Why should entrepreneurs watch it? Because Belfort is the perfect example of what an entrepreneur should not be. Driven by greed and with no empathy for those he was conning, his debauched life eventually led to his downfall.

So, what do you think?

Did we get all the best entreprenur movies? Did we miss any? Let us know in the comments, and happy watching!






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