Movies and Documentaries That Will Inspire The Entrepreneur In You

Yes, you can mix productivity and pleasure

It's no secret that one of the best ways to relax is to kick back and enjoy a movie. For the business-minded, it’s not just a way to unwind, it’s also a way to learn a key life lesson or pick up a business insight or two.

Here, a list of the best movies and documentaries budding and veteran entrepreneurs alike must watch:

Jerry Maguire (1996)

This blockbuster gave us one of Hollywood's most memorable lines—"Show me the money!" It shows the struggles of Jerry Maguire (Tom Cruise), who leaves the high-octane world of corporate sports talent management in a crisis-of-conscience moment. You've got to admire Maguire's dogged determination to succeed on his own with just one stubborn and hard-headed client (Cuba Gooding Jr.) and a single mom (Renee Zellwegger) on his side.

Why you should watch it: Starting and running a business based on one's core values is crucial to your success. After all, if you don’t believe in your own product or company, how can you convince others to do so?

Moneyball (2011)

Based on a true story, the film centers on Billy Beane (Brad Pitt), the general manager of the Oakland Athletics baseball team. Beane tries to beat the bigger and richer ball clubs by using unconventional methods. His sidekick is assistant general manager Peter Brand (Jonah Hill), a geeky economics graduate from Yale, who uses computer algorithms to rate players. They build a team based on bargain-bin players that most scouts have rejected and labeled as flawed but rated well based on their analytics.

Why you should watch it: A business, no matter how small, can become great and successful with innovation, creative out-of-the-box thinking, and the proper use of data and analytics.

The Social Network (2010)

This biopic of Facebook co-founder Mark Zuckerberg (Jesse Eisenberg) traces the modest beginnings of the now multi-billion-dollar empire. The film also depicts Zuckerberg's personal and legal challenges as a startup entrepreneur when the business started growing quickly and exponentially.

Why you should watch it: Facebook is a real-life fairy tale of how the biggest of businesses can start with the simplest of ideas, and how important it is to carefully navigate the difficult journey from startup to booming business.

The Pursuit of Happyness (2006)

This is based on the true story of Chris Gardner (Will Smith), a single father who struggles to make ends meet and fails repeatedly to properly provide for his 8-year-old son (Jaden Smith). It's heartwarming to witness Gardner persevere against all odds to complete his unpaid internship at a prestigious brokerage firm.

Why you should watch it: Be inspired to persevere no matter what you are going through, and develop resilience and determination no matter the difficulties and odds you may face.

A Second Chance (2015)

In this sequel to the Pinoy blockbuster One More Chance, newlyweds Popoy (John Lloyd Cruz) and Basha (Bea Alonzo) struggle to balance their dream of starting a family while running their own business venture: an architectural firm.

Why you should watch it: You'll be encouraged to find the proper work-life balance especially if your personal and professional relationships intersect and intertwine, as in the case of a family business.

Top Entrepreneur Documentaries:

FYRE: The Greatest Party that Never Happened (2019)

This docu is an in-depth, insider look at the highly publicized failure of the highly anticipated glitz and glamour event-that-never-was—the Fyre Festival of 2017. It focuses on how founder Billy McFarland and co-founder Ja Rule turned their grand vision for a party-to-end-all-parties into a marketer's dream...which eventually turned into a complete and utter disaster.

Why you should watch it: This documentary clearly illustrates the importance of execution, logistics, and attention to operational details vs. just having a great idea and great marketing.

Startup.com (2001)

Considered as one of the top entrepreneurship business documentaries in the last two decades, it shows the real-life boom and bust of a startup (govWorks.com) during the dot-com bubble era. Two friends plan to build a website which can accept payments for all government bills, including parking tickets and taxes. Soon, they are able to raise US$60 million in funding from venture capitalists, after which the bubble bursts.

Why you should watch it: This documentary shows the ups and downs, the struggles, the tensions, and the obstacles any startup will experience, including their effect on their personal lives and relationships.

Silicon Cowboys (2016)

It's a David vs. Goliath story of how Compaq challenged IBM in the portable PC market in the 1980s, eventually becoming the largest supplier of PC systems in the 1990s.

Why you should watch it: If you're a small business going up against industry giants, this documentary is for you. Both an inspirational and cautionary tale, Silicon Cowboys will help you understand what it takes to challenge (if not take down) a Goliath.

The Startup Kids (2012)

In-depth interviews with very young web entrepreneurs from the US and Europe (including those from Vimeo, Dropbox, and Soundcloud) make this documentary an inspiring, eye-opening one for entrepreneurs of any age.

Why you should watch it: Realize that age is not a hindrance to becoming a successful business owner. Rather, it takes passion, inspiration, and a LOT of hard work.

Turumba (1981)

This international award-winning documentary by renowned Filipino artist Kidlat Tahimik (a.k.a. Eric de Guia) tells the story of a small family from Pakil, Laguna and their microenterprise of making papier-mâché figurines for the annual Turumba Festival. Their quiet lives suddenly turn into chaos when a German entrepreneur commissions them to produce 30,000 papier-mâché figures for export. The whole village gets involved in the production of the figures, and the now-growing business enterprise starts affecting their family, their ways of working, and ultimately their values and culture.

Why you should watch it: A business enterprise can affect not only individuals but a whole community, which is why it’s important to keep one's values intact as the business grows. Success shouldn't make you question your values and beliefs, much less corrupt you.

With this list of for-the-entrepreneur-in-you movies and documentaries, your downtime will not only be relaxing, but fruitful and productive, too! 

To know how to make your business future-ready, learn more at the Globe myBusiness page.