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Top 5 Movies Every Entrepreneur Needs to Watch

5. Blow – (2001)

One of my rogue theories is drug dealers tend to be some of the most prolific and intensely focused entrepreneurs. Our culture tends to objectify some of the more infamous “gangsterpreneurs” such as Al Capone, Pablo Escobar, and Frank Lucas. Regardless of what criminal activities they did, we’re fascinated with the riches they were able to obtain while overcoming the reach of the law. I think it’s fun to consider what if they were legitimate CEO’s of Fortune 100 companies. Would Al Capone make a good CEO or was bootlegging alcohol and masterminding criminal enterprise his only choice?

Blow follows the true story of George Jung’s rise from poverty to being one of the biggest cocaine dealers in the world,. There are plenty of both good and bad entrepreneurial lessons in this film achieving success. It’s easy for any passion filled entrepreneur to cross the line and become a greed obsessed megalomaniac. This film serves as a warning to not cross that line regardless of the nature of your business. George’s electric personality and emotional intelligence is arguably what brought him to the top of his industry. It’s fun to watch that come across on screen and analyze how he operated more closely to a corporation than a cartel.

Interesting fact: George continues to be an entrepreneur after being released from 20 years of incarceration. He’s currently writing No Domain, the official biography of John McAfee.

4. Boiler Room – (2000)

Here we have another cautionary entrepreneurs tale fictionally based on the true story of The Wolf of Wall Street. Jordan Belfort, and his pump and dump firm, Stratton Oakmont. This is a fun film with a phenomenal cast. After you see it once, you’ll find it hard to pass up when you come across it again.

It’s the classic “too good to be true” startup. Excess and greed are evident everywhere you look. Nobody questions where the money is coming from. As long as it keeps coming, everyone seems to be perfectly OK with it.

It’s an ironic story because the main character was a successful entrepreneur operating an underground casino. He sought to legitimize his life by pursuing a career on Wall St. in order to impress his father. However, the only way he could live up to the entrepreneurial standard of living he was accustomed to, was to join an illegitimate operation. Many entrepreneurs pivot back-and-forth between real world jobs and entrepreneurial endeavors (Let’s stick with the legal ones though.).

Amongst other great entrepreneurial lessons on what to do and what not to do, this film grounds you. It makes you realize there are no shortcuts to entrepreneurial life.

3. Aviator (2004)

A billionaire and one of the greatest entrepreneurs in the past 100 years, Howard Hughes, has made a lasting impact on modern society. In fact, Las Vegas as we know it would not exist if it were not for Mr. Hughes. Howard Hughes was being kept awake at night by the bright neon sign from the ‘Silver Slipper’ casino, so he bought the casino and dismantled the sign. If you are in the movie business and want to reach a similar performance, you might want to Get the best acting advice from The Actor’s Group Orlando.

For these reasons alone, this is a must watch for any business owner. This big-budget movie does a great job of giving you a taste of Howard’s life. It also highlights one of the negatively perceived traits common with high level entrepreneurs, OCD. It was his OCD that took him to the top and ultimately was the cause of his demise. As an entrepreneur, it’s extremely important to keep a good balance of your physical and mental health. This movie will give you a great reason to revisit your strategy on life balancing.

Liked the movie? Check out what happened to Howard Hughes fortune after he died:

2. Pirates of Silicon Valley (1999)

This movie tells the true story of Steve Jobs’s and Bill Gates’s rise to power in Silicon Valley and the rivalry between them. You aren’t a real software entrepreneur unless you’ve seen this cult classic. It’s such a cool story and made me realize a few things:
Xerox had no clue what they had. Unfortunately, this is the story of many big businesses that become overly bloated with red tape. They literally handed the mouse and GUI to Steve Jobs and Apple on a silver platter.
It’s fun to see the college lives of Steve Jobs and Bill Gates. You can tell they are just normal human beings who had a strong passion for technology and their competitive spirit led them on a beautiful entrepreneurial journey.
Most people have fond memories of Steve Jobs, but this movie shows the ruthless side to Steve in his relentless drive towards the top.
Apple and Microsoft continue to vie for technological domination. Their competition continues to drive revolutionary lifestyle improvements for all of humanity. When the world reflects on this time period, it will become evident that perhaps without these two tech titans, technology would not have progressed at the pace it has.

1. Flash of Genius (2008)

Odds are you haven’t seen this movie. That is precisely why it’s my top choice for “must watch” entrepreneur films. Flash of Genius is a beautiful story of David vs. Goliath. Engineering professor, Robert Kearns invented and patented the intermittent windshield wiper. This idea was ripped off by Ford and Chrysler who used it without his permission, or royalty. Robert set upon an epic legal battle for the ages in which he eventually ends up representing himself in a court of law defending the patent. Highlighting the importance of intellectual property, every entrepreneur can appreciate this film.