Ten Movies All Entrepreneurs Need To Watch

When you talk about the ‘must see’ movies for all entrepreneurs, some highly expected names get tossed around: Glengarry Glen Ross, The Wolf of Wall Street, Citizen Kane.

And these are all incredible films, but I want to dig a little deeper, visit some titles you may or may not associate with your career. Films that changed my life or altered my perspective on how I do things. Plus, these are all really fun, entertaining flicks. So not only will these titles send you home with a nice little lesson, odds are, you’ll be swept away for 120 minutes to a land of fantasy created by Hollywood’s best.


Is this about ghosts? Yes. Is it about being a successful entrepreneur? They are scoffed at by everyone that matters, until the ghosts begin showing themselves. These scientists believed in their product and ignored the criticism and in the end, they were the only one providing a service the people of New York so desperately needed. Absolutely! The Ghostbusters go against everything everyone in the city was saying and started a business catching something most people don’t believe in. They were innovative, committed, and had a bit of fun too.


Jon Favreau’s film is a call to all who are ready to make the leap to entrepreneurship. In this 2014 flick, Favreau’s character leaves his high end restaurant job as a chef to pursue his own thing. He buys a food truck and hits the road, craving his own success, all while attempting to find that balance of work and family, something we should all keep an eye on.

The Game

In this 1997 David Fincher film, Conrad (Penn) famously asks his incredibly wealthy and successful brother Nicholas Van Orton (Douglas), “what do you get for the man who has everything?” A thriller that teaches perspective. The leading character had a routine life and didn’t appreciate everything as he should and it wasn’t until his deadbeat brother showed him an alternative view, did he see the world differently. A lesson we can all use.

The Sandlot

We follow a group of boys who one summer play baseball every waking moment, until they find themselves in the biggest pickle ever. We can all relate to those summers where we spent more time outdoors than in, and how as we grew older, no matter how close we were to our friends, in the end, we all went our own way. But there is always one friend, like Benny in The Sandlot, who knows what they love and knows what they’re good at and in the end, chasing that passion leads them to success.

The Producers

Sure, your concept isn’t perfect yet, but you never know what may come of it. In this Mel Brooks smash hit (I prefer the 1967 version – Gene Wilder is brilliant) Brooks demonstrates that throwing anything against the wall and seeing if it will stick sometimes actually works. When producers Max Bialystock and Leo Bloom try to create a sure-fire flop, they end up finding the biggest success of all.

40 Year Old Virgin

What does this have to do with being a successful entrepreneur? Everything! This Judd Apatow masterpiece is all about the character of Andy (Carell) waiting for 40 years for what is right for him. Even when the pressure is on from his friends to make a move for the simple sake of making a move, he deflects and holds out. And this is exactly how we should approach business. Sometimes we are presented with jobs that, despite the pay looking great, it goes against everything we ever wanted. We should all be Andy. Don’t make a move because someone tells you you should. Wait until the right opportunity arrives. Even if it takes 40 years.

All Things Must Pass: The Rise and Fall of Tower Records

This Colin Hanks documentary follows Russ Soloman, the rebellious founder of Tower Records and how he walked to the beat of his own drum, and in turn, garnered huge success. He allowed his employees to identify and be who they were and in turn, they loved him for it. This film also serves as a good warning sign to be aware of everything in your control and even things that are not.

Begin Again

This journey shows us that a lot of times, the path to making it on your own isn’t the path you thought you’d ever take. With Dan (Ruffalo), an ousted record executive trying to find his way, he has a chance run in with a disgruntled musician (Knightley). Together, they make an odd collaboration that just seems to work. Doing everything against the grain ends up leading to personal and commercial success.

The Social Network

David Fincher stokes our brains again, retelling the story of Mark Zuckerberg and his tale of how he went about creating Facebook. This film is perfect for someone who wants to see the growth from startup to massive success (seen through the Hollywood filter). Filled with pitfalls and glam, The Social Network proves that sometimes, one has to stick to their guns, all while being flexible.

Office Space

Mike Judge’s cult classic is about Peter Gibbons (Livingston) who is fed up with his mundane, soul sucking job and one day decides he, “doesn’t want to go anymore.” This is the ultimate flick for those in need inspiration to get away from your insane boss, or any boss at all. Or if you’re one of the fortunate ones that doesn’t have to answer to anyone, this film is a brilliant demonstration of how and how not to treat your employees, cause really, no one wants to come in on Saturday.


Cynthia Johnson

Cynthia Johnson is an entrepreneur, marketing professional, and keynote speaker. She is Co-Founder at Ipseity Media, a personal brand development and management agency in Los Angeles. She is also Co-founder at Insurehound, and InsureTech Startup based in San Francisco. Previously, she was Partner & Director of Marketing for RankLab, a digital marketing agency listed in Inc. Magazine's Fastest Growing Private Companies in 2015. In July of 2015 RankLab was acquired by American Addiction Centers where she worked as their Director of Brand Development. She is an advisor to a social good company, DIVONA, as well as nGage.social, an influencer advertising startup. Cynthia is on the Forbes Agency Council, and a member of the Young Entrepreneurs Council. Cynthia was listed as top social media people to follow by Inc. Magazine, top 50 marketers on SnapChat by Mashable, top 12 Female Entrepreneurs that Inspire by Darling Magazine, and top 20 people in SEO by Guardian.