Garage Blog

9 Movies Every Entrepreneur Shouldn’t Go Another Day Without Watching

With another Oscars come and gone, we’re reminded of how powerful cinematic interpretations of our lives can be. While we’re often used to provocative or emotion-based subject matters grace the screens year after year, topics that tackle the professional realm shouldn’t be left unnoticed.

In honour of this universally transcendent medium we call film, we’re listing some of the most essential ones that entrepreneurs should watch to full immerse and make sense of the world they live in.

Don’t see a film you think should be on the list? Be sure to leave it in the comments below!


We’re starting off with what is perhaps the most well-known documentary about the corporate world in the last two decades. This film, which is based on award-winning reporting by Bethany McLean and Peter Elkind, explores the collapse of the Enron Corporation through its many actors of deception and greed, making it the most deliberate exploration of business ethics and corporate corruption of recent memory.


When it comes to competition, no one is more familiar than that of the entrepreneur. Based on an award-winning play of the same name, this film takes a intensely fast-paced and extreme approach to depicting the dynamics of competition in business through tactical negotiation, and manipulation as it follows four real estate salesmen battling it out for the top.


While some may roll their eyes at the inclusion of this film, we’re here to argue that the film takes important perspective on relationship building, power dynamics, and climbing the career ladder - no matter how dramatised. After all, many of us do think of our superiors as being a little evil from time to time, right?


While most know this film as a legal drama (or for Julia Oscar’s Best Actress Win), it’s in fact another potent exploration into the very important topic of business ethics or corporate social responsibility. It not only deals with the issue head on from the perspective of its victims, it also addresses the very real and relevant issue of gender biases and discrimination in business, and the resolve in which allows women to overcome them.


While most wouldn’t categorise this film under ‘business’, its relevancy is all too clear when you take a step back to consider its themes of leadership, power & influence, and long-term vs. short-term strategy. Ultimately, the relationship between a gang of criminals working to pull off a lucrative heist prove not-so-different from that of a startup team working to pull off a new project. Amirite?


You saw this one coming. There’s no way we can leave the story of the inception of what is the most successful social platform ever off this list. While the film itself is overdramatised in Hollywood fashion, the story itself is of struggle and resilience - one that every entrepreneur can relate closely to. Most importantly, it aptly portrays what a modern tech startup, in the way that we perceive them today, must do in order to succeed.


Another tale of sacrifice and dedication, this true story really hits home in telling a story of one man’s unwavering dream of making a better life for himself. While the film can be slightly overly sentimental at times, it does justice to an honest portrayal of the highs and lows of entrepreneurial life, of which giving up seems all to easy to do, and the prospect of it all paying off, impossible.


While this film is strictly speaking a sports movie, it in fact tells a compelling story of innovation that entrepreneurs can relate closely to. It tells the true story of Billy Beane, the General Manager of the financially struggling baseball team Oakland A’s. The resulting theme centres around his innovative approach to making ends meet, which is a task entrepreneurs are all too familiar with.


No film list about the business world would be complete without this 1987 classic. The story follows one of the most compelling characters in recent cinematic history Gordon Gekko: provocateur of greed to say the least. The question of morality comes to a head when his protegé Bud Fox is faced with a decision that would no only define his career but character. The film explores the themes of wealth, fame, and how we succumb to these excesses.

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