HomeEntrepreneurship16 Best Movies Every Entrepreneur Should Watch

16 Best Movies Every Entrepreneur Should Watch

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One of my favorite quotes is by Zig Ziglar, “Motivation is like bathing. It works better when you do it daily.”

This is especially true for entrepreneurs. We all need some inspiration from time to time, and one of the best ways is to take a break, chill, and log into Netflix. 

Regardless of where you are on your entrepreneurial journey, here are the best motivational movies that will be sure to inspire you to push through your challenging moments, and none of them are about sports or bro-culture. These movies will surely encourage you, boost your productivity, and help bring imagination, originality, vision, and flair to your role. Well, maybe a couple of them come close. I’ll let you decide. 

Let me know what you think and share what flix you would add to the list. 

1: Office Space (1999)

Have you forgotten why you left your corporate gig? Well, this is the perfect movie to jog your memory. Yes, being an entrepreneur is tough. It’s a “You eat what you kill,” journey, but it beats cranking out weekly TPS reports daily. Take the time to remember where you’ve been to help you get to where you wish to be. 

2: Breaking Away (1979)

You might wonder what a movie about a small town-boy obsessed with cycling has to do with entrepreneurship: the answer, everything. It’s an alchemy of passion, relationship, identity, and David beating Goliath. It’s a reminder that anything is possible when you are riding with people you trust. 

3: The Princess Bride (1987)

Every entrepreneur knows that obstacles are constantly coming at you like Rodents of Unusual Size (ROUS), but you must fight through them to achieve true love, which is the one thing you can’t deny. And along the way, you need support, courage, and perhaps a miracle if you want to have fun storming the castle.  

4: The Pursuit of Happyness (2006)

Nothing is more inspiring than a true story. If you’ve “beaten the pavement,” you will relate to Chris Gardner’s (Will Smith) story of trying to make ends meet. It’s a story of love, grit, and optimism to believe that the next sale might be the one that changes everything for you.  

5: Shawshank Redemption (1994)

Success and escaping prison don’t happen overnight. Many entrepreneurs quit too soon because they expect success to happen quickly, but the ones that breakout know that it takes Andy Dufresne (Tim Robbins) like day-in and day-out perseverance. It underscores the value of a long-term vision to help you through your challenging moments when it doesn’t feel like you are making any progress. 

6: A Wonderful Life (1947)

This holiday tradition is the perfect movie for any entrepreneur who wonders if they are making an impact. The answer is yes! The story of George Bailey illustrates what happens when you shift your perspective and redefine what it means to be the “wealthiest man in town.”

7: Joy (2015)

Like the Pursuit of Happyness, Joy is another true-to-life unlucky-to-lucky story showcasing entrepreneur and business magnate Joy Mangano. Like many entrepreneurs, Mangano’s journey (Jennifer Lawrence) has it all from her early struggles to managing her family to inventory craziness to taking advantage of her big break with QVC. 

8: Coco before Chanel (2009)

Gabrielle (Coco) Chanel’s (Audrey Tautou) was a woman before her time. Her rags to riches story will inspire everyone, but it’s significant for aspiring women entrepreneurs. Her story is about what’s possible with focus, tenacity, and grit to stay in the fight even when the odds are not in your favor. It will even challenge the traditional worldview on how men and women should behave as they pursuit corporate success. 

9: Willy Wonka and The Chocolate Factory (1971)

This classic from the ’70s has a key entrepreneurial lesson: make sure you surround yourself with people you trust. With entrepreneurial success, you might be in the same position as Willy Wonka (Gene Wilder): Who runs your company next? This film is a beautifully bizarre tale that reinforces the notion that work works when you have purpose, fun, and integrity. It’s the best way to your Golden Ticket. 

10: Money Ball (2011)

You might think this is a baseball movie, but it is so much more than that. It’s about having the courage to change even when everyone thinks your are crazy. It shares the story of how Billy Beane (Brad Pitt) changed how we think about sports but more importantly, it’s about adapting, listening to new ideas, and shifting your perspective so you can see new opportunities.  

11. The Founder (2016)

This is the story of Mickey D’s and its founding father, Ray Kroc. You=’ll discover Kroc’s superpower of ideation and determination as he creates the greatest franchise restaurant in history. It’s a story of grit, persistence, tenacity, and resilience that will inspire any entrepreneur looking to become known for changing our culture. 

12. Wolf of Wall Street (2013)

There are some cringe-worthy moments in this film. Still, it shares meaningful lessons about success, fame, fortune, greed, and the story you tell yourself. It is also a cautionary tale of what could happen without discipline and awareness; your success can spiral down the tube faster than you created it. 

13. Glengarry Glen Ross (1992)

This is sales person’s movie. It’s where we learned who gets coffee and who doesn’t. Today, thanks to the play that became a movie, we know that coffee is for closers. Plus, it shares valuable leadership lessons on how not to lead a sales team. After all, sometimes we get the best lessons from our worst bosses.

14. The Social Network (2010)

This is a must-watch for today’s social media-dependent entrepreneur. It tells the story of the world’s youngest billionaire and Facebook founder, Mark Zuckerberg. You’ll discover how he did it from Harvard dorm room and the challenges he faced along the way, including rifts with his co-founders. 

15. Baby Boom (1987)

This is the perfect movie for the corporate warrior looking to leave the hamster wheel behind to make it independently. It’s the original boss babe movie that demonstrated that running your own business can be better than trying to crash through the corporate glass ceilings of someone else’s business. Plus, the scenes of Vermont are gorgeous. 

16. The Devil Wears Prada (2006)

This is another real-life story of a young professional driven to “make it.” Our heroine, Andy, eventually discovers that status isn’t all that it’s cracked up to be, especially if you lose identity on the way to the top rung of the ladder. Like other films, it challenges the belief that success and wealth are indicators of a happy life.

There you have it, the best motivational films that will inspire any entrepreneur to stay on their long-game journey toward success. I know I’ve leverage the lessons from these films to help me keep focused on the long game. 

So who’s ready for some popcorn and inspiration? 

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Michael OBrienhttp://michaelobrienshift.com/
Michael OBrien is a leadership and resilience expert based in New Jersey. When he's not riding his bike, he loves preventing bad moments from turning into a bad day and hanging with his family and their furry four-legged friends.

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