Top 6 Entrepreneur Movies (And What We Can Learn from Them)

By Evan Cartwright

Based on the positive response we received from our last pop culture-themed blog post, we thought we’d take a page out of Hollywood’s book and create a sequel. And what better way to continue the entertainment theme than with movies!

Here are our top 6 favorite entrepreneur films (and what we can learn from them):

1. The Pursuit of Happyness

Buoyed by a heartwarming and inspiring performance by the always-brilliant Will Smith, the triumphant story of Chris Gardner shows that education or impressive credentials aren’t a guarantee of success, but rather an unrelenting passion and refusal to let life’s obstacles keep you from success. Also, developing your people skills should be a top priority for any entrepreneur, as they can open doors that you might never have previously known or considered.

2. Citizen Kane

Often regarded as the greatest film in cinematic history, Orson Welles’ “Citizen Kane” is renowned not only for its groundbreaking storytelling and visual effects, but also the tragic trajectory of its protagonist. Charles Foster Kane, loosely based on newspaper magnate William Randolph Hearst, demonstrates revolutionary business tactics in his quest for wealth and prestige—he’s a master of PR and self-promotion whose boundless ambition allows him to ascend from an impoverished upbringing to become a powerful tycoon. However, his acerbic, uncompromising personality ultimately alienates everyone close to him and he ends up alone at the end of his life. Kane’s arc reminds us that while starting a business is a noble goal, it pays to have one’s priorities in order and remember what’s truly important.

3. Office Space

Besides generating a newfound appreciation for Red Swingline staplers and cathartic printing smashing sessions, Mike Judge’s cult workplace comedy perfectly highlights the drudgery and quiet desperation of modern cubicle dwellers. From the petty bureaucracy, to the clichéd business jargon, to the monotony of day-to-day work, Office Space does a fantastic job of satirizing white collar work and reminds us that life is too short to not go out and pursue your business dreams.

4. Ghostbusters

With the reboot coming out next month, it feels appropriate to mention everyone’s favorite paranormal investigators. Egon, Ray, Venkman and Winston (and the ladies of the new movie) are the perfect example of an innovative startup—they identify a previous untapped market, and leverage their collective knowledge and experience to fulfill a niche need. Also, the Ghostbusters show the value of having memorable and effective branding—their logo and theme song are instantly recognizable.

5. The Wolf of Wall Street

The importance of ethics is front and center in Martin Scorcese’s raunchy romp through the world of finance. The larger-than-life Jordon Belfort, as played by Leonardo DiCaprio, exhibits the perfect combination of confidence and creative sales tactics—his aggressive pitching style and ability to exploit his client’s vulnerabilities helps him develop his own successful financial firm. His also develops a unique, tight-knit business culture and inspires a near-fanatical loyalty in his employees.

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However, his excessive, hedonistic lifestyle and willingness to cut corners ultimately ensures his downfall. Belfort’s story teaches us that profitability should never be pursued at the expense of customers.

6. Moneyball

You don’t have to be a sports fan to enjoy Brad Pitt’s statistics-inspired rags-to-riches journey as the general manager of the Oakland A’s. As the underdog team with the lowest salary available for its players, Billy Beane (Pitt) facing the losing prospect of having his star players being constantly being poached for better opportunities. His unique solution is to analyze statistical data and pick players based on their stats alone to fill in gaps needed on his team. Similar to Beane, entrepreneurs should seek to take an innovative approach to an existing business model and seek to improve it.

What did you think of our pop culture choices? Did we miss any of your favorite movies? Leave us a comment about what films you think best show the entrepreneurial spirit!