Top Ten Films Every Entrepreneur Should Watch: Great Strategies From Unconventional Characters

Top Ten Films Every Entrepreneur Should Watch: Great Strategies From Unconventional Characters
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Pretty Woman - Negotiating

prettywomanRichard Gere wants something. Julia Roberts has it. She also knows its worth, and has a good idea of what the financial status of Mr Gere’s character Edward, is. This puts her in a strong position cause she knows the market.

Upon negotiating a deal whereby Vivian (Roberts’ character) will spend a few days being Edward’s “beck and call girl” rather than just spending the night with him, the two begin to talk numbers. She makes a bit of a mistake by voicing her math and thoughts, but ends up stating a reasonable price of $4,000. He counters with an offer of $2,000 and she refuses. Of course they meet in the middle. The conclusion to the scene shows that they were both prepared to have gone with the other’s deal, but ultimately they are both happy.

Be flexible in your negotiations, but know your limit. Know as much about the status of the person you are dealing with, as well as the current market situation, and you will be in a strong position.

Calendar Girls - Unique Selling Point

calendargirlsOK, so I’m not suggesting you pose nude for your company calendar like the ladies of the WI did in Calendar Girls, but you can certainly take a lot from this film in regard to establishing your USP. It’s all about twists on an original idea really.

The WI always produced a yearly calendar of them baking cakes, crafting and the like, but really needed something that would sell more than a few copies in order to make money for the local hospital. What other calendars sell well? Nude ones! And so the two happily are combined. Ladies of a certain age posing in the altogether, being subtly covered by cream buns, flowers, or some balls of yarn, so still keeping a somewhat traditional element.

Think about your business idea – has it been done before, what makes you different? Take your idea and turn it on its head – play with it. Whatever the result you might be pleasantly surprised. It’s not about seeing what is doing well in your market, it’s about making your mark. Imitators will never be as successful as those with original ideas. As the ladies from the WI are testament, if you have a truly individual idea, the marketing of the product becomes so much easier.

Casablanca - Running the Show

casablancaRunning a bar in a politically unstable environment wouldn’t be everyone’s idea of a good business and there are a whole ton of lessons you can take from this movie. Offering a product or service that no one else dares to, but that you know others want is going to mean success, but trouble. You have to be prepared for that, and a little headstrong. Rick (Humphrey Bogart), knows he is always in the right and declares “I stick my neck out for nobody.” He is also a man of high ethics though and will not stand for any nonsense.

Pick your fights. You won’t win all of them, but if you stick to your personal morals and treat everyone fairly you are going to earn respect. If people respect you, they don’t mess you around.

Anchor Man - Dealing with the Competition

anchormanRon Burgundy is the most successful news anchor in town, until the lovely Veronica Corningstone arrives on the scene. Rather than seeing her abilities, he just sees that she is a good-looking woman, and goes into what he thinks is a charm offensive. He completely underestimates her as competition though (in fact he doesn’t even see her as competition), and this becomes his undoing. As she quietly goes about her business in a professional manner, even impressing the misogynistic editor, Ron shows himself to be less competent by comparison.

The two try to outwit each other in a series of childish pranks that does neither of them any good, but ultimately Ron is the one to fall as he takes it so personally while Veronica retains her professional head.

Never underestimate your competition. Never assume that you are the best. Keep on top of your game and strive to improve, rather than expecting the same approach you’ve adopted in the past is always going to see you through.

Godfather - Project Management

godfatherDon Corleone could teach us all much about business, but I believe it’s in the area of project management where the Godfather excels. After all, making someone an offer they can’t refuse, in the way the Godfather does, is not going to win you any sales contracts!

Project management the Don Corleone way is based on respect, nurturing relationships and knowing how to handle difficult members of the family. Using violence in your venture is not one I’m recommending, and for the most part the Godfather achieves what he does based on quiet assertiveness - he leaves the aggressive side to others.

This is a great lesson to learn – leave the bits you aren’t so good at for someone else to do. As an entrepreneur you believe in your venture 100% and know it inside and out, so are likely to spend most of your time trying to do everything rather than trust it to others. Delegation is a hard thing to learn, but is a simple one to enact and will improve your venture’s chance of success hugely. You are not an expert in everything, just as the Godfather isn’t. Be the puppet-master and leave those who have the expertise in their own areas to get on with doing it.

Cocktail - Securing Funding

cocktailOne of the trickiest parts of getting any venture off the ground is funding. While Tom Cruise’s character Brian Flanagan goes about his career route in an unconventional way, he eventually gets something right. At the start of the film he is an enthusiastic bartender and cocktail entertainer and he is happy doing just that. Through various twists and turns he realizes that it is more than just fun, it is really his passion.

But who is going to loan him the money to make his dream of owning his own cocktail bar a reality? He knows it’s an unsteady profession, and that he himself is not an attractive proposition to any would-be investors. Although he spends the film as a “Jack the lad” expecting everything to just work out, he eventually realizes that hard work is the only way to go.

In realizing this, he also shows others his passion, commitment, and hard-work ethic, which is what ultimately convinces his uncle to loan him the money.

We don’t all have relations that can help us in this way, but recognize that there are other routes besides a conventional bank loan. Securing any one of these means putting in the hard work across the board to show them your worth.

Die Hard - Be The Best

diehardDo you think there’s any point in Die Hard when John McClane feels he isn’t the best man for the job? If there is then he doesn’t show it. He has the skills, the ingenuity and the self belief to see him through the toughest of physical and emotional situations. Whether it’s saving his ex-wife from being a hostage, to blowing away the competition using an elevator shaft, he thinks on his feet and takes charge of the situation.

It’s not enough to be the best in your field, you have to know it. This confidence will also filter through to others who will start to believe it too, but be prepared to back this up with solid action – talking the talk isn’t enough on its own.

You’ve Got Mail - Being the Little Fish

youvegotmailNo one starts out as the big fish in the pond; you start small and build your way up. But getting started in business when you are a little fish can be hugely overwhelming. Meg Ryan and Tom Hanks chat online, but have never met in reality. Neither of them know that she is the little bookshop owner, and he the owner of a big bookstore chain just opening around the corner from her business. Initially, Meg Ryan dismisses the large bookstore as “nothing.” Always a mistake! Realizing too late, as her profits fall around her ears she takes action… but in the wrong way.

Instead of focusing on her own business she instead sets about to bring down the large bookstore in a variety of media events and campaigns. She gets noticed, but it doesn’t improve her business. She left it too late, and didn’t take the right action, and is forced to close her store.

What should she have done? Not everything in business has to be a fight. She should have played to her unique selling point of offering a personal service, added touches such as those adorable cloth bags and hosting events. There is no use competing with the big boys on discounts and such, cause you just don’t have the buying power. See where you can cut costs or narrow your profits. Perhaps you could take a cut if customers bought more than one item – like a 3 for 2 type offer – this way you are still offering them a form of discount, but are encouraging more sales too.

Evita - Not Being Loved But Doing It Anyway

evitaYes, I know this one is based on a true life story, but there are still worthwhile lessons for the entrepreneur to learn. Not everyone likes Eva Peron, and while she does care about this, she doesn’t let it stop her – which actually means she gets a lot of people that love her too.

There are people that think she doesn’t deserve her position in life as Argentina’s first lady, as she came from a poor background. She refuses to let her meager beginnings become the dictator of what will happen later in life and she strives for better. Although marrying well became her way of doing it, she didn’t forget her humble beginnings, and used them in order to feel empathy and make the lives better of Argentina’s poor.

Do what you feel is right, and do it in your own way. If there are people who don’t like it then tough. No one got successful by copying someone else and pandering to everyone along the way. Use your background to inspire you and push you on, not to be the excuse you give for not succeeding.

Star Wars - Blind Faith

starwarsProbably the least business-oriented film of our selected ten, but Star Wars bears a single lesson worth learning. As an entrepreneur you have to have a great product or idea, and a belief in what you are doing, but things aren’t always going to go your way. What do you do in situations like this?

“Use the force”, or in more realistic terms have total and utter blind faith in what you are doing is right, and will be successful. Not quite the Field of Dreams “build it and they will come,” as you will have no doubt done more research than just coming up with a random idea and believe everyone will want it, but a true belief in your abilities and chances of success.

On learning how to use the light saber for the first time, Luke’s eyes are covered by a helmet and he gets zapped a few times, before he truly believes in the force and eventually deflects four laser shots in a row without looking. Have faith in what you are doing, even when the odds seem stacked against you and it will pull you through the worst times.

Only Ten?

So there you have it, my top ten unconventional movies every entrepreneur should watch - quite a varied bunch, I think you’ll agree. There are no doubt others you can think of that I have left out, so please feel free to leave a comment below and help out your fellow entrepreneurs. You get out, what you put in – perhaps another business lesson worth remembering.


  • DVD images courtesy of
  • Article written using author’s film knowledge, combined with a few facts from the Internet Movie DataBase.