8 Movies Every Aspiring Entrepreneur Must Watch

8 Movies Every Aspiring Entrepreneur Must Watch

Movies have been made on just about any topic. From blood-thirsty serial killers who manage to stay ahead of the police long enough to extraterrestrial beings craving for a piece of the human experience. You’ve probably also watched movies on crazy conspiracy theories, creepy ghosts and haunted sites, politics of betrayal, the art of war, love and romance, to mention but a few.

Entrepreneurship is yet another topic that’s been widely explored by filmmakers. There are tons of movies depicting entrepreneurs as they undertake their daily endeavors in a bid to achieve their ultimate goals – wealth creation and financial independence.

The one common feature with movies on entrepreneurs is that they all emphasize the fact that success doesn’t happen overnight. You’ve got to pull all the stops, sometimes go for broke, to earn it.

We’ve prepared a list of the top 8 movies every aspiring entrepreneur must watch.

1. Jerry Maguire

Director: Cameron Crowe

Producers: Cameron Crowe, James L. Brooks, Laurence Mark, and Richard Sakai

Starring: Tom Cruise, Cuba Gooding Jr., Renée Zellweger, Kelly Preston, Jerry O’Connell, Jay Mohr, and Bonnie Hunt

Release Date: December 13, 1996

Running Time: 139 minutes

Jerry Maguire is an inspirational film about budding entrepreneurs who believe in their ability to strike it out on their own. According to the movie, sometimes one good customer and sheer determination are all you need to launch a successful entrepreneurial venture.

The protagonist in the film is a highly influential sports agent named Jerry Maguire (Tom Cruise) who works for a successful company. Maguire is fired from the company after advocating for his belief that sports agents need a more personal touch, which means fewer but reliable clients.

Although his beliefs cost him his lucrative job, Maguire eventually establishes a successful sports managing agency. He starts off with only one client that believes in his ethos – a volatile footballer named Rod Tidwell (Cuba Gooding Jr.), and his former co-worker Dorothy (Renée Zellweger) as his only employee.

2. Rounders

Director: John Dahl

Producers: Joel Stillerman and Ted Demme

Starring: Matt Damon, Edward Norton, John Turturro, Famke Janssen, Gretchen Mol, John Molkovich, and Martin Landau

Release Date: September 11, 1998

Running Time: 121 minutes

Rounders is a film about the underground and often unpredictable world of high-stakes poker. The movie’s title actually means a person who travels from city to city in search of high-stakes card games.

In the film, two friends have to find and win high-stakes poker games so they can pay off a huge debt. The friends are a New York City law student and talented poker player Mike McDermott (Matt Damon) and his childhood friend Lester “Worm” Murphy (Edward Norton).

The director of Rounders succeeds in highlighting one crucial success lesson – the importance of sacrificing something good in order to pursue something greater.

3. Pirates of Silicon Valley

Director: Martyn Burke

Producers: Steven Haft, Nick Lombardo, and Leanne Moore

Starring: Noah Wyle, Anthony Michael Hall, Joey Slotnick, John DiMaggio, and Josh Hopkins

Release Date: June 20, 1999

Running Time: 95 minutes

Pirates of Silicon Valley is a biographical drama television series that explores the rivalry between Steve Jobs of Apple Computer and Bill Gates of Microsoft Corporation as they struggle to build their respective technology empires. The focus of the film is on the implications of this rivalry in the development of personal computers.

Pirates of Silicon Valley brings into focus the value of believing in your dreams and following through with them regardless of your age and experience. In the movie, you’ll watch how a 20-year-old managed to change the fortunes of a huge corporation like IBM.

Another valuable lesson in this movie is that you shouldn’t fret when someone else copies your ideas. Instead, what matters is how well you put your ideas into practice. After all, competition is part and parcel of the corporate world.

4. Boiler Room

Director: Ben Younger

Producers: Jennifer Todd and Suzanne Todd

Starring: Giovanni Ribisi, Vin Diesel, Nia Long, Nicky Katt, Scott Caan, and Ben Affleck

Release Date: February 18, 2000

Running Time: 120 minutes

If you’re an aspiring entrepreneur seeking to learn valuable concepts in the field of sales, you might want to begin by watching Boiler Room. The movie is about young and ambitious American brokerage schemers who employ hyper-aggressive marketing tactics to peddle stocks to unsuspecting buyers.

Boiler Room’s plot is punctuated by lots of dramatic and criminal scenes. But the underlying theme is how entrepreneurs can strike it rich without necessarily putting in substantial capital investment. All you need is aggressive marketing skills and the ability to pounce on unsuspecting clients at the slightest opportunity you can find.

If executed diligently, these sales tactics can easily turn you into an overnight millionaire. Who wants to work their entire life anyway?


Directors: Jehane Noujaim and Chris Hegedus

Producer: D.A. Pennebaker

Starring: Tom Herman and Kaleil Isaza Tuzman

Release Date: May 11, 2001

Running Time: 106 minutes is a documentary film based on the real-life start-up is a dotcom start-up that raised $60 million in funding from Hearst Interactive Media, Kohlberg Kravis Roberts (KKR), Sapient, and the New York Investment Fund.

This is one of the few entrepreneurship movies that adequately addresses the topics of business financing, growth management, and team management.

Although the film is more about the boom and bust of the dotcom period, it also contains valuable tips that modern-day entrepreneurs can implement to cushion their ventures from going under. You’ll also be able to learn how friendships can be ruined by business partnerships.

6. Julie and Julia

Director: Nora Ephron

Producers: Nora Ephron, Laurence Mark, Eric Steel, and Amy Robinson

Starring: Meryl Streep, Amy Adams, Stanley Tucci, Chris Messina, and Linda Emond

Release Date: August 7, 2009

Running Time: 123 minutes

Julie & Julia is a biographical comedy-drama film that blends two stories – that of Julia Child (Meryl Streep) and Julie Powell (Amy Adams). The film basically contrasts the life of Julia Child during the nascent years of her culinary career with that of a budding New Yorker Julie Powell who aspires to cook all 524 recipes in Julia Child’s book within a year.

Julie & Julia is a story about ambitious entrepreneurs who are willing to take on a daring project. It highlights how passion and commitment can inspire you to overcome seemingly insurmountable obstacles and achieve your full potential.

The movie is recommended for film lovers looking for an entrepreneurship movie with less dramatic scenes.

7. The Social Network

Director: David Fincher

Producers: Scott Rudin, Dana Brunetti, Michael De Luca, and Ceán Chaffin

Starring: Jesse Eisenberg, Andrew Garfield, Justin Timberlake, Armie Hammer, and Max Minghella

Release Date: September 24, 2010

Running Time: 120 minutes

The Social Network is a biographical drama film that chronicles Mark Zuckerberg (Jesse Eisenberg)’s journey in founding the giant social networking platform Facebook. Much like Pirates of Silicon Valley, The Social Network portrays the early rise of tech giants in Silicon Valley.

The movie introduces you to a tenacious Mark Zuckerberg who’s determined to actualize his dreams despite all the setbacks. You’ll see how Zuckerberg conceptualized and nurtured the idea of Facebook in his Harvard dorm, ostensibly to get back to his recent ex-girlfriend.

To make his dreams come true, Zuckerberg must ignore a few financial and legal requirements. His dealings with Facebook cofounders also portrays Zuckerberg as an entrepreneur lacking emotional intelligence.

8. The Wolf of Wall Street

Director: Martin Scorsese

Producers: Martin Scorsese, Leonardo DiCaprio, Riza Aziz, Joey McFarland, and Emma Tillinger Koskoff

Starring: Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McConaughey, Kyle Chandler, Rob Reiner, and Jon Favreau

Release Date: December 25, 2013

Running Time: 180 minutes

You’ve most certainly heard of The Wolf of Wall Street, even if not already watched the movie. Considered one of the most controversial films in recent times, The Wolf of Wall Street is based on the 2007 memoir of disgraced Wall Street stockbroker Jordan Belfort (played by Leonardo DiCaprio). The movie depicts Belfort’s career as a New York City stockbroker and how he presided over multimillion-dollar fraudulent activities committed by his brokerage firm Stratton Oakmont.

The Wolf of Wall Street highlights how greed and the insatiable appetite for ill wealth can destroy overnight an empire that took years to build. Its plot is also punctuated with lots of high drama on the fastest ways to waste your fortune, from doing drugs to runaway spending on sex.

Despite all the negativity in it, The Wolf of Wall Street contains valuable investment tips and secrets of stockbrokers.


There are hundreds of films about entrepreneurs and we cannot possibly exhaust them in one article. However, the above-reviewed movies are a great place to begin your search for a sobering and inspiring film about entrepreneurship.

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