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10 Must-See Movies for Entrepreneurs

HostPapa Blog / Business  / 10 Must-See Movies for Entrepreneurs
14 Aug

10 Must-See Movies for Entrepreneurs

Movies can be a great way of escaping the grind of everyday life, but some movies can provide much more than that. They can inspire us, they can teach us a life lesson, or they can stir up something inside of us that we didn’t even know was there. That’s why sometimes watching the right movie can motivate you to complete that big project; or remind you why you left the “comfort” of 9-5 in the first place.

The HostPapa resident cinephiles have been hard at work, and compiled a list of 10 must-see movies for entrepreneurs – have you seen them?

Office Space (Mike Judge, 1999)

Office Space has become an absolute reference for all office workers tired of having to report to an incompetent, greedy manager. If you’ve ever needed motivation to move on to greener pastures, this one fits the bill. The movie’s hilarious characters are so relatable, you’ll surely see yourself in one of them – although hopefully you’re not Milton.

The Hudsucker Proxy (Joel & Ethan Coen, 1994)

Innovation is difficult. Having a good idea is hardly ever enough when you have to fight against conformists and competition, and figure out the right way to make people see what it is that you’re aiming for. This Coen brothers’ masterpiece of dark humour is a perfect reminder of why you always have to keep pushing forward.

Revolver (Guy Ritchie, 2005)

This one might be a tough pill to swallow, but follow along. Guy Ritchie’s Revolver is probably his least known movie – it’s also the least fun. Unlike his blockbusters, Snatch and Sherlock Holmes, it’s not an action-driven roller coaster ride. No, this one will make you uncomfortable, make you wonder what on Earth are you are watching, and it might even make you want to stop following this blog. But push through… it’s worth it. One of the most important things when running your business is to check your ego at the door. It’s not about what makes you feel better, or what you’ve done before; it’s about what works. Few movies show you the work it takes to be truly humble, and those that do, always risk not doing it as well as Revolver.

Monsters University (Dan Scanlon, 2013)

No, no, we’re serious. Grab your kids, make some popcorn and watch Monsters University. While your kids laugh at the nonsensical lives of these immature animated monsters, you can think about what’s really happening. Here you have a couple of guys with a dream, who think they have all the answers on how to get there, but it doesn’t work. Every seasoned entrepreneur knows that in business, sometimes the direct route isn’t always available. So, you have to adjust your plans and take a couple steps back, but never lose sight of the goal – just like Mike and Sully. And, like Mike and Sully, maybe what you’re really missing is the right partner. Think about it. You’ll also get a kick out of it… those monsters are hilarious!

The Shawshank Redemption (Frank Darabont, 1994)

This is a classic movie that’s made it to pretty much every Top 10 list out there, business-related or otherwise. Few stories are as inspiring as the tale of Andy Dufresne (Tim Robbins) who worked for years and years and years to achieve a single, clear objective, even if it meant crawling through a river of $4!t – to come clean on the other side. Sometimes the task at hand is unpleasant, sometimes the plan takes longer to happen than you thought; but if you’re willing to put in the hard work, it’ll pay off in the end.

Glengarry Glen Ross (James Foley, 1992)

If you could only watch one business-related movie ever, it should be this all-time classic.  With an all-star cast, including Al Pacino, Jack Lemmon, Alec Baldwin, Ed Harris, Alan Arkin, and Kevin Spacey, this movie is a take off of David Mamet’s Pulitzer Prize-winning play regarding real estate schemes and scams of the 1980s. The great thing about this movie is that the application to your business is right there, from the start. Always Be Closing. Whatever your business is, you need sales; so whatever you’re doing, whatever your industry is: Always Be Closing. It’s a tough world out there, and sometimes it’ll be ugly… very ugly. But the good leads belong to the closer so… you guessed it: Always Be Closing.

Barbarians at the Gate (Glenn Jordan, 1993)

Based on the best-selling book by Bryan Burrough and John Helyar, this story focuses on the management buyout attempt of RJR Nabisco and the greed of Wall Street. The leveraged buyout was, at the time, widely considered to be the ultimate example of corporate and executive greed. If you want to know about 1980s-style leveraged buyouts, where executive managers raise funds against assets to take over a company, then you must see this film. Barbarians at the Gate stars James Garner as RJR Nabisco CEO F. Ross Johnson, and James Pryce as KKR’s Henry Kravis.

Boiler Room (Ben Younger, 2000)

The film is about a fly-by-night company called J.R. Marlin and how a college dropout gets recruited as one of their brokers. J.R. Marlin is small investment firm off the Long Island highway, and it’s packed full of Wall Street wannabes that couldn’t cut it. The story focuses on the ambition of Seth Davis (Giovanni Ribisi), a recent graduate who gets sucked into the cult-like sales “boiler room” atmosphere of the scam firm. The movie also stars Vin Diesel and Ben Affleck.

Citizen Kane (Orson Welles, 1941)

The incomparable Orson Welles writes, directs, and stars in this all-time classic film. It shows off his complete creative brilliance. The movie is about a fictional publisher, Charles Foster Kane (Orson Welles) who emulates the real-life world of newspaper publisher and business tycoon William Randolph Hearst. The movie plays off of Hearst’s controlling personality and follows how he built his empire through his interpersonal relationships, while characterizing some aspects of his actual life. The whole movie stems from the last word spoken by Kane: “rosebud”. What is so important to be the last word of such a powerful, influential man? This movie won’t give you a straight answer; but you don’t need one. The question is whether Kane was happy with (or in spite of) everything he achieved as a business tycoon. Are you happy with your achievements? To put it in simple terms – your life goals should drive your business goals – not the other way around.

Tommy Boy (Peter Segal, 1995)

The late Chris Farley teams up with David Spade in this classic comedy about a family business on the brink of bankruptcy after its owner dies and makes the maybe not-so-wise business decision to give the company to his buffoon-like son, Tommy. To save the business, Tommy (Farley) and the former owner’s assistant Richard (Spade) head out on a road trip to close vital sales. This is an ultra-funny movie that proves the need for all business owners to have a proper succession plan in place!

Trading Places (John Landis, 1983)

An instant Wall Street classic, this movie stars Dan Ackroyd as Louis Winthorpe III, a top executive for a commodity trading firm, and Eddie Murphy as Billy Ray Valentine, a homeless beggar. The film focuses on a key question: is a person’s character shaped by nature or nurture? As a result of a bet by two power-hungry business owners, Louis is stripped of his job and made homeless, and Billy Ray takes over his job. The owners bet each other to see if the characters would end up in the same situation as before their lives changed – with Billy Ray ending up homeless again, and Louis becoming a successful businessman. Or, would the situation change them to accept the new role they’ve been handed in life? The movie provides simple but effective business advice such as: don’t judge a book by its cover, take advantage of opportunities that are presented to you, and don’t fall back into old habits. While the business decisions made in the movie would probably sink a company in real life, the principle is there, along with lots of laughs.

Ocean’s Eleven (Lewis Milestone, 1960 / Steven Soderbergh 2001 )

Whether it’s the Danny Ocean of the 1960s (Frank Sinatra) or 2000s (George Clooney) the business mindset remains the same: create a clear objective, surround yourself with the right people for the job, and it will get done right. Both movies are about assembling a team of 11 people – all experts in their fields – to pull off a giant Las Vegas heist. While your business is hopefully more legitimate than that of Danny Ocean’s, the idea that you need a trusted and highly skilled team to accomplish great things holds true. A one-man (or one-woman) show is possible for starting up a small business, but a successful entrepreneur recognizes that he or she is not the best at everything. Handing control over to experts can be the best decision to help a business flourish.

So, while business is not necessarily “like the movies”, there are some valuable lessons that can be learned from even the least expected movies, like Monsters University and Tommy Boy. Do you agree with our list? Are there any that should have made the list – besides Wallstreet obviously… that’s already in too many lists! Tell us by commenting below.

Alexandra Sparks Hudson

Alexandra is an important part of the HostPapa content team. She lives in Montreal, reads excessively, is passionate about SEO and loves fashion. Her friends call her Sparks. You can too.


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