Four Movies Every Entrepreneur Needs To Watch

The Best Screen Stories To Inspire Success

Being an entrepreneur is hard work and full of risk and struggle; we all need a little boost of inspiration once in a while to keep us positive and motivated. From biographies to crime, here are the top movies every entrepreneur needs to watch that will hopefully inspire an entrepreneurial streak in you.

Pursuit of Happyness

The incredibly inspiring true story of Chris Gardner will speak to anyone who has known the struggle and constant rejection involved in the process of trying to get ahead in life and build a business. Following Gardner’s entrepreneurial spirit as portrayed by Will Smith, he sacrifices and loses everything for his business dream. Later on, a chance encounter leads him to an unpaid internship at a brokerage firm that eventually lead to him starting his own company. This biographical film proves that hard work, perseverance and grit, along with a little luck makes for a great recipe for success. The passion and sacrifice portrayed in the film is highly infectious and something every entrepreneur should be willing to embrace.

The Aviator

Before there was Elon Musk or Richard Branson, there was Eric Hughes. This biographical film captures both the personal life and business struggles of one of history's most enigmatic and glamorous entrepreneurs and aviation pioneer. The film portrays his life between the late 1920’s and late 1940’s, during which time Hughes became a successful film producer and an aviation magnate while simultaneously struggling with severe obsessive-compulsive disorder.

Watching the young entrepreneur place big bets and enjoy himself in the process reminds us of the upside of pursuing something we thoroughly believe in amidst the struggles. Besides highlighting the entrepreneur’s glamorous lifestyle, the film also reveals the private struggles that boiling beneath the surface, showing that the best among us can rally and achieve tremendous things despite our personal handicaps and struggles.

Office Space

For those needing an extra push to pursue their entrepreneurial dreams, this is the perfect movie to get your engine started. This movie perfectly encapsulating the quiet desperation of the modern cubicle-dweller and how the petty bureaucracy, structure, and drudgery of modern work are nothing short of soul-destroying. Office space does a fantastic job of satirizing the experience and serves as a constant reminder that life is way too short to spend hunched over in a cubicle. If you find yourself in a soul-destroying situation, it’s up to you to change it.

The Wolf Of Wall Street

A fine line often exists between great entrepreneurship and good old-fashioned con artistry. Leonardo DiCaprio's portrayal of scam-artist stockbroker, Jordan Belfort, drives home this point the best. While Belfort was certainly entrepreneurial in building his empire, he crossed many ethical and legal lines that catapulted him into the con category and taking many others down with him in the process. Without self-awareness and reflection, it’s easy to end up engaging in behaviours that may compromise the longevity of your business as well as the people behind it. While reaching the pinnacle of success is every entrepreneur’s dream, the film serves as a timely reminder cautioning us against the blind pursuit of wealth.


Written by
Huiling covers a diverse range of topics at Billionaire, fuelled by her passion for environmental sustainability and humanitarian advocacy. In her downtime, she enjoys getting lost in a good book and tending to her urban garden.

More Like This:

Recommended for you:

BLLNR (Billionaire) is a platform for Entrepreneurs, Business Leaders and Creatives in Singapore.

Join Our Newsletter