Regardless if you’re a seasoned entrepreneur or thinking about throwing in the white towel in regards to your 9-to-5 job, one of the best sources of inspiration for when times get tough or advice on starting a business is through movies.
I know. You probably don’t have the time to watch a movie. But, remember, you need to give yourself a break and decompress - unless you want to get burnt out. And, you can always squeeze in a flick when traveling, commuting, or when you first wake-up on a Saturday morning.
While there are hundreds of movies that entrepreneurs are fans of for one reason or another, here are fifteen movies that each and every entrepreneur loves.
1. The Social Network
Was David Fincher’s 2010 film a bit overdramatized? Sure. But, why wouldn’t we want to watch how Mark Zuckerberg went from a Harvard student to founder of the most popular social network in the world?
While the film isn’t 100% accurate, it did a solid job of showing the obstacles (like lawsuits from people claiming your idea was theirs), to meeting with investors to dealing with success in our own ways. In fact, each time I watch this I get motivated to become a better entrepreneur.
2. Boiler Room
At some point each and every entrepreneur faces a moral dilemma when they question whether it’s worth going against their values to make lots of money. And, that’s exactly what this 2000 film depicts so accurately.
Boiler Room focuses on Seth Davis, a 19 year old dropout who joins the morally questionable brokerage firm J.T. Marlin. At first, Seth enjoys the success that he experiences, but he realizes that there’s something suspicious about the firm and must decide between what’s right and wrong.
On top of that, there’s also a lot of motivational tips on becoming a stronger salesperson.
3. The Pursuit of Happyness
Based on the true story of Chris Gardner, Will Smith stars as a struggling salesman and father who literally loses everything. Does he give-up? Never. He works harder than his competitors and finally became a successful entrepreneur, investor, stockbroker, motivational speaker, author, and philanthropist.
If this 2006 film doesn’t give you goosebumps and keeps you motivated to chase your dreams, then I don’t know what will.
4. Pirates of Silicon Valley
This 1999 made-for-tv movie recalls the early days of Microsoft and Apple and the rivalry that developed between Bill Gates and Steve Jobs, along with their individual trials, triumphs, and how each “pirate” formed their empires.
There’s lots of pointers to learn for aspiring entrepreneurs on how to start a business, such as dealing with your fiercest competitors and how to execute your business idea.
5. The Shawshank Redemption
First off, this is one of the greatest movies of all-time. It’s a classic that you could watch over-and-over again. But, for entrepreneurs, the fact that Andy Dufresne, a man wrongly imprisoned for murder, always makes the best out of every situation and finally executes an escape plan, is reason enough to watch and observe Andy.
Launching a startup isn’t easy. There’s a lot of hurdles to overcome, but you still need to make the best out of every obstacle and be patient. If you do, you can finally break free from fear and hold onto hope.
This 2011 film was a passion project for Brad Pitt. Once you see it, it’s easy-to-understand why. It’s the true story of Billy Beane, the General Manager of the Oakland A’s who didn’t have enough money to put together a competitive baseball team. Because of this, Beane had to find innovative ways to piece together a winning ball club that would win 102 games and win their division.
How can you not find this story inspiring? It’s the perfect illustration of how you don’t need a lot of money to stay competitive in your business as long as you are creative and have a vision.
7. Something Ventured
This is a 2011 documentary that investigates the rise of venture capitalism in the 20th century by telling the stories of the people who founded Apple, Atari, Intel, and Cisco. Having this perspective of the investors who helped launch some of the most successful companies in Silicon Valley gives entrepreneurs better insights into what venture capitalists are looking for in startups and how to work with them in order to build a successful company.
8. Office Space
Anyone who has worked a 9-to-5 job can relate to Mike Judge’s 1999 irreverent comedy. For those who haven’t seen this cult classic, it follows Peter Gibbons, who after being hypnotized, realizes that he no longer can stand his office cubicle and starts stealing from the company. In the end, Peter realizes that he would rather work manual labor, where he’s outside and happy, than being stuck in a place that he hates.
This is a quintessential movie to motivate you to ditch that 9-to-5 job.
9. Wall Street
Oliver Stone’s 1987 classic introduced the world to the motto “Greed is good,” along with the morally reprehensible Gordon Gekko. Drawn to the lifestyle that Gekko has built for himself, young stockbroker Bud Fox does a little insider trading and loses his morality in exchange for greed and success.
This is another movie that stresses the importance of not letting greed and success get to your head. If so, you could lose the things that matter most in your life, such as your friends, family, and values.
This is another classic movie that is pretty much beloved by everyone. And, it’s easy to explain why. Rocky Balboa is an underdog boxer from Philly who suddenly has the opportunity to battle the heavyweight champ Apollo Creed.
Even when the odds are stacked against you, never give up. Work your tail off, believe in yourself, and you might just go the distance. And, the soundtrack from Bill Conti is some of the most motivational pieces of music that you’ll ever hear.
11. Glengarry Glen Ross
Not all entrepreneurs are familiar with the brutal world of sales. In fact, it can get extremely vicious and competitive. That’s what this 1992 film, which is based on David Mamet’s Pulitzer Prize-winning play showcases as it explores the harsh world of the Chicago real-estate industry.
As an entrepreneur, be prepared to get betrayed as your competitors look to gain an edge over you. Sadly, some people just cannot help themselves.
12. Iron Man
This was the movie that launched the Marvel Cinematic Universe in 2007. But, do you remember hearing that Robert Downey, Jr. based his performance of Tony Stark on Elon Musk? According to the actor, both Stark and Musk were men who “had seized an idea to live by and something to dedicate themselves to” and weren’t going to waste a moment in their lives.
On top of that, what entrepreneur doesn’t wish that they were also a billionaire tech-innovator who travels the world sharing their ideas?
13. Jerry Maguire
Just because you seemingly have everything, like a successful career and equally successful finances, doesn’t mean that you’re happy. After all, money and success doesn’t always mean that you’re happy or fulfilled. That’s what Jerry Maguire figures out after realizing that sports agents shouldn’t just be concerned about money. They should actually care about their clients and look out for their best interests.
Jerry loses everything during his journey, but he eventually finds success in both his personal and professional life. The lesson? Be passionate and never stop chasing your dream. If you do, you’ll become a successful and happy - no matter what you choose to do with your life.
14. The Big Short
I was pretty furious when I first watched this 2015 that explores how several clever individuals predicted the credit and housing bubble collapse during the mid-2000s. Why? Because it was a situation that could have been avoided - but nothing was done to prevent the bubble from bursting. Even more disturbing, it appears that we haven’t learned our lesson.
While some of the characters exploited this system, others decided to take on the big banks so that this wouldn’t happen again.
Entrepreneurs can learn a couple of things from this movie. For starters, it demonstrates how entrepreneurs are always on the lookout for new ways to make cash. This was even one of the main reasons I started my online invoicing company... I didn't realize how big the financial industry was until I watched it. On the other side, it also shows how entrepreneurs are often willing to risk it all, whether it’s their reputation or all the money in their bank accounts, in order to make difference.
15. Tucker: The Man and His Dream
This 1988 biographical film, which was directed by Francis Ford Coppola, tells the story of Preston Tucker and his mission to take on the big three automobile manufacturers with the “Tucker Torpedo”, aka the “car of tomorrow.”
For entrepreneurs, this movie has everything. It shows the passion and creativity that Tucker possess, along with his journey to secure financing, his unique marketing campaign, and the challenges of being a small company battling industry giants.
The most valuable lesson though, is that even though you have everything in place and a superior product, you still might fail when everyone is against you. Still, that doesn’t mean that you should stop trying to chase your dreams.