Movies: Six Inspirational Movies For Entrepreneurs

There are a lot of movies out there about people who “make it.”

It’s just one of those story tropes we humans seem to love. The outsider, the underdog, the kid who gets bullied at school—when we see stories about how people with humble beginnings go on to win the day, the girl and/or a thick stack of cash, it’s fun!

It’s kind of weird then that there actually aren’t quite as many movies about entrepreneurship. For whatever reason, filmmaking hasn’t settled on too many ways to tell compelling stories about entrepreneurs.

But there are exceptions. Pretty good ones, at that.

If you’re looking for some money-making motivation, here are six inspirational movies about entrepreneurship. And if you’re looking for practical inspiration in how you can put your entrepreneurial mind to work, check out It’s all about helping you build that road map.

1. Catch Me If You Can

Catch Me If You Can is not strictly about an entrepreneur. It’s about an unusual man who happens to have a genius for getting what he wants through weaving convincing stories. It’s based on a true story and it provides a fascinating window into just how easily it is to make people believe in you if you believe in yourself.

While it doesn’t chart the trajectory of an entrepreneur per se, so much about this character’s experiences are oddly relatable from an entrepreneurial point of view.

We get to see him solve problems out of the box, weaving realities around him as new situations arise. He’s quick, creative and always looking for that next opportunity. He’s not exactly likable, but it’s impossible not to admire him!

His adaptability and cleverness can’t fail to inspire.

2. Rogue Trader

Rogue Trader is another movie based on a true story. It charts the rise and fall of a bank employee who single handedly destroyed a bank through financial mismanagement and a series of catastrophic decisions.

It’s definitely a cautionary tale for entrepreneurs, but there’s a lot more to this movie than a simple warning about what not to do.

It’s a fascinating insight into the psychology of taking one step too far. How a series of reasonable decisions can rapidly snowball into a completely unreasonable and unjustifiable situation. The movie is also wonderful at showing the emotional dimension of money and how difficult it can be to make sensible decisions when it comes to building a fortune.

Ewan McGregor’s acting is awesome too.

3. Erin Brockovich

Let’s continue our run of “based on a true story” movies with Erin Brockovich. The beginning point of this movie is almost the complete opposite of entrepreneurism. An impoverished woman with few prospects secures a low-paying job for a local lawyer.

Erin Brockovich, to all appearances, is a person destined to the daily struggle of “just getting by.”

But then she stumbles on an intrigue. I won’t give it away, but through a series of discoveries, Erin suddenly becomes all kinds of fired up, and suddenly everything changes for her. The pieces just fall into place.

Erin Brockovich is a story about someone who stumbles across something they passionately believe in—and then pursues it relentlessly.

The portrayal of someone succeeding through gumption and backbone is inspiring to watch, and it’s a great reminder for entrepreneurs of the kinds of qualities you need to get things done.

4. The Devil Wears Prada

This movie is about an entrepreneurial anti-hero. Miranda Priestly is an awful person in so many ways, but she’s also powerful, successful, indomitable and at the top of her game.

This movie is, first and foremost, just a bucketload of fun. It’s about how both good and evil can lie at the heart of the pursuit of excellence, and sometimes they’re hard to distinguish from one another. It’s delicious to watch the characters representing these extremes duking it out on the screen.

On a more practical level, this movie also explores how your personal and professional ethics can collide in unexpected ways—always a good theme for those of an entrepreneurial disposition to have floating around in the back of their ambitious minds!

Oh and Meryl Streep. Wow. She owns the role. She’s simply amazing to watch.

5. Office Space

Office Space is just a deliciously fun movie about how much office life can, to put it bluntly, suck giant weenies. If you’ve decided to go it alone and escape the nine to five grind, this movie is a great one to set in reserve in case you ever need a reminder about why you decided to leave that world for good.

One extremely cool take home from this movie is how easy it is to pursue dreams that won’t actually make you happy. It places a big question mark over pursuing money for its own sake. There’s more to success and there’s more at stake to life than making money.

This movie also features one of the most perfect depictions of a horrible boss in the history of cinema. If none of these other themes float your boat, it’s worth seeing for that alone.

6. Forrest Gump

Some readers just groaned. I get it. A pretty hefty chunk of this movie is self-indulgent, corny and (for many) just kind of irritating.

The thing is, it’s also the perfect convergence of the classic underdog story and how entrepreneurial success can come from the weirdest of places. To me, this makes Forrest Gump not just watchable, but incredibly entertaining.

Forrest Gump is simultaneously an idiot and a genius. He constantly misinterprets what’s happening around him, but somehow at the same time he captures the exact essence of his time and place. He sees things with strange clarity and, ultimately, this places him on a path to success—not just financially, but in finding what makes him truly happy.

Gump is, in ways, the quintessential entrepreneur. He’s dauntless, he knows what he wants and he has a knack for ignoring the voices that would bring him down.

Stories about the heart of entrepreneurial enterprise are out there. I like these movies because they don’t try to offer any kind of advice on how to make money. There are plenty of resources out there which can do that. These movies instead tell fascinating stories about flawed people who bend the rules, choose their own path and ultimately bring something unique to the world.

Speaking as an entrepreneur who wants to find a unique road in this world, that’s pretty cool to watch.


Updated: January 7, 2019 — 8:38 am