Leonardo DiCaprio in The Wolf of Wall Street

There is plenty of advice out there for budding entrepreneurs to read, but sometimes watching something can be a lot more informative and there are a lot of lessons to be gleamed from the industry leaders of the silver screen. This selection of must-see films for entrepreneurs and small business owners alike can offer a crash course in some of the do’s and definite do not’s of running your own business, no matter what field you are working in. Watch all of these and you’re guaranteed to learn a thing or two. How many of these have you seen? Did we miss your favourite business flick? Let us know in the comments below!

Wall Street (1987)

Oliver Stone’s classic film depicts the financial excess and ‘greed is good’ attitude of 1980′s Wall Street in all it’s lurid detail. The plot follows Bud Fox, a junior stockbroker played by Charlie Sheen, who is desperate to break into the upper reaches of the financial elite. He is taken under the wing of the notoriously ruthless broker Gordon Gekko (Michael Douglas) and exposed to a world of material wealth beyond his dreams, but it comes at a moral cost as Bud is encouraged to embezzle funds and participate in dubious insider trading to get ahead. This forces him to seriously consider whether or not it is the right career for him. A highly entertaining film with a strong takeaway for entrepreneurs that money isn’t everything and real success never arrives overnight unless it has a price.

The Social Network (2010)

The ultimate tale of the modern day startup, David Fincher’s re-telling of the Facebook story (based on Ben Mezrich’s book The Accidental Billionaires) attracted huge acclaim from everyone other than Mark Zuckerburg. The film depicts the rise of the social networking website, from the conception of ‘The Facebook’ in Zuckerburg’s (uncannily portrayed by Jesse Eisenberg) Harvard dorm room and the early struggles and subsequent legal battles with co-founder Eduardo Saverin and the Winklevoss twins, who claimed Zuckerburg had stolen their idea.

While the accuracy of the events shown in the film have been disputed, it offers a valuable lesson to entrepreneurs in the value of loyalty and choosing choose their team members wisely, not to mention being careful to not allow power to affect their decision making abilities.

The Wolf of Wall Street (2013)

The true story of New York stockbroker Jordan Belfort (played by Leonardo DiCaprio) was a runaway success, netting $392 million at the box office worldwide and quickly becoming one of the most iconic films of recent years. The film shows the dangerous side of business success, as Belfort is embroiled in fraud, corruption, drugs and all manner of other illegal activity. While it is a cautionary tale, it also serves as an inspirational one for entrepreneurs – as Belfort rises to this position from meagre beginnings, starting off selling penny stocks and rising through the ranks of Wall Street using little more than his natural charisma and incredibly persuasive salesman techniques. There is plenty of wisdom to be taken from the story of a man who run the gamut of having nothing, having it all and then having nothing again. An absolute must see for anyone with aspirations towards big business.

The Pursuit of Happyness (2006)

This 2006 drama is the true story of Chris Gardner, the American stockbroker who now owns Gardner Rich & Co and is a multi-millionaire – however, things weren’t always so great. The film depicts the time Gardner (played by Will Smith) spent homeless on the streets of San Francisco with his young son. A truly inspiring story, rather than accepting his fate, Gardner accepts an unpaid brokerage internship with a competitive firm and tries to earn some money on the side by selling medical devices. Despite being much older and less academically qualified than the other interns, Gardner’s work ethic prevails and he ultimately lands his dream job. Very few films sum up the importance of determination for budding businessman quite likes this one.

Jerry Maguire (1996)

This drama with Tom Cruise as the titular character has become an iconic piece of 90′s cinema, and the story still has lots of valuable lessons for entrepreneurs. Maguire is sacked from his position at a high flying sports agents firm after he decides to take a more honest, less aggressive approach to his work. He decides this is a chance to start his own firm which can adhere to his new approach – we see the struggles involved in starting a new business and finding clients – but ultimately he becomes more successful than ever. A good story to remind us that all of the hard work involved in the daily grind of running a business is ultimately worth it.

Moneyball (2011)

On first glance this story of a struggling baseball coach who comes up with an innovative way of ranking players may not seem like a goldmine of business advice, but there are lots of transferable ideas here. Like most startup founders, the Oakland A’s coach Billy Beane (played by Brad Pitt) is working on a shoestring budget despite desperately needing to bring in more resources. How can he build a winning team without the mountains of cash available to the bigger teams who keep buying up all his best players? He looks deeper.

Beane turns to statistical data to try and uncover players who are performing consistently well without ever being noticed. Inevitably this system is a huge success – indeed it is widely used in many professional sports today, and the real life Beane is considered something of a pioneer. There are plenty of lessons here for businesses, namely that looking to do things in a new way (particularly with data) can often lead to a way of working which allows you to compete beyond your financial constraints.

Glengarry Glen Ross (1992)

Glengarry Glen Ross is a classic business drama (based on David Mamet’s award-winning play) detailing the questionable sales tactics of a group of estate agents based in Chicago, featuring an incredible cast featuring Al Pacino, Alec Baldwin, Ed Harris, Kevin Spacey and more. When a new motivational trainer arrives in the office and announces that all but the top two salesmen will be fired at the end of the week, it launches a bitter underhanded rivalry between colleagues desperate to generate more sales. The film is well known for popularising the phrase “Always be closing” – a mantra of many enthusiastic salespeople. It also serves to give a fascinating insight into the ferocious and expletive laden, dog eat dog mentality which pervades many industries and the problems such a work environment can breed.

Up In The Air (2009)

This comedy-drama, starring George Clooney and Anna Kendrick, tackles the human side of the credit crunch which saw many people laid off from long term jobs. Clooney plays Ryan Bingham, a “corporate down sizer” employed to fly all over the country to deliver people the news they have been made redundant.

As part of the financial tightening, even Bingham’s job is under scrutiny as the firm considers delivering such bad news by video conferencing rather than flying him all over the country. It is up to him to try and convince his superiors this is news which needs to be delivered personally. The film is an excellent reminder to business owners for the importance of maintaining relationships within their company, and that staff are people rather than just numbers.

Startup.com (2001)

This documentary follows the story of e-commerce website GovWorks, an American startup founded by Kaleil Isaza Tuzman and Tom Herman, at the tail-end of dot come startup phenomenon. It is an amazing story of a company which began as a 2 man idea with no money and went on to become a company with 200 employees and generate funding of $50 million within 12 months. Far from being sorted, things go downhill from there.

The site struggles to compete with better funded competitors and the two founders begin to butt heads on numerous issues.  Within 3 years of formation, they burned through all their funding and were forced to sell to a large corporation. This is a great lesson in the value of planning, financial management, employee relations, and just about everything else which has to be monitored in launching a successful business. You can learn a lot from watching the business mistakes of others.

Rogue Trader (1999)

This film tells the true story of Nick Leeson, a British trader (portrayed here by Ewan McGregor) who worked for London’s Barings Bank in the 90′s and whose irresponsible trading ultimately led to the collapse of the company.

After promising beginnings with Barings, Leeson is appointed to work as the General Manager of the Trading Floor for the Singapore International Monetary Exchange. This new found power gets the better of him however, and before long Leeson is gambling with the company funds and is concealing a staggering £800 million worth of losses in a secret account. A fascinating cautionary tale which shows the impact which individual actions can have even within huge multi-national companies.