5 Essential Movies for Entrepreneurs

A selection of films every entrepreneur could learn a lesson from.

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The Social Network (2010)

Great artists leave behind a work of art that transcends time and shapes their legacy. For Da Vinci, it’s the Mona Lisa. For Beethoven, it’s his Fifth Symphony. For Aaron Sorkin, The Social Network (2010) remains the pièce de résistance in his delectable oeuvre.

The biographical drama recounts Facebook’s rise to power, primarily focusing on Mark Zuckerberg (Jessie Eisenberg) and Eduardo Saverin (Andrew Garfield), the architects of the largest social media platform in the world. The Facebook story is likely the ultimate startup tale; a journey that started with a few teenaged Harvard University teenagers setting up a social networking website for Ivy League students resulted in an enterprise that is now worth $510BN (as of June 2018).

The movie deals with the trials and tribulations synonymous with establishing a successful startup, from the initial stages of securing financing to keeping the vultures at bay when the idea bears fruit. It further examines how loyalties can shift instantaneously when billions are involved. Zuckerberg gets sued for Intellectual Property theft, and Saverin himself files a lawsuit over the unjust dilution of his shares.

The Social Network informs, enlightens, and entertains in equal measure. Laced with Sorkin’s signature scathing wit and whirlwind dialogue, David Fincher’s movie is a delight to the senses and sheds light on the inner workings of Zuckerberg, who was world’s youngest self-made billionaire, only recently usurped by Kylie Jenner.

Steve Jobs (2015)

A titan of technology, Steve Jobs was a pioneer of the personal computing revolution. Tech enthusiasts the world over hold aloft the co-founder of Apple in reverence. 8 years after his premature demise at 56, the legend of Jobs shows no sign of subsiding. On the contrary, veneration only grows stronger.

Directed by Danny Boyle (Slumdog Millionaire), the Steve Jobs movie delves deep into the psyche of its eponymous protagonist, exploring his relationships and his uncompromising pursuit of perfection. Structured unlike other biographical fares, the movie is akin to a three-act play, each part taking place 30-minutes before the launch of a major Apple product: the Macintosh (1984), the NeXT Computer (1988) and the iMac (1998).

Steve Jobs (Michael Fassbender) is questioned and denounced by every figure in the movie, and much like in real life he alienates a fair few people but remains staunchly behind his ideologies and his vision, undeterred by the torrents of critique. His decision to enforce end-to-end control of Apple products, which meant tech hobbyists could not modify and customise their computers as was the predominant trend is ridiculed in the movie.

Had he folded under pressure then Apple, as we know it, wouldn’t exist. End-to-end control is now one of the key differentiators between Apple and its competitors; it cultivates the exclusivity and desirability that Apple is now renowned for.

However, the movie doesn’t deify Jobs. His follies and foibles are laid bare for the audience to see and learn from. Steve Jobs was a remarkable man; it would not be hyperbolic to say he changed the world. And this equally remarkable movie offers an illuminating and intriguing look behind the curtains, both literally and figuratively.

Moneyball (2011)

In 2002, the Oakland Athletics were in a dilemma. The Major League Baseball (MLB) outfit had just surrendered three of their star players, were operating on a trifling budget contrasted to their rivals and still reeled from the repercussions of a dismal season a year prior. Yet they recorded one of the grandest seasons in their history, shattering records along the way. Moneyball chronicles the remarkable true to life journey.

How did they accomplish it? The answer lies in the science of sabermetrics, the empirical analysis of baseball statistics. Oakland Athletics’ general manager Billy Beane (Brad Pitt) flung out the century-old rulebook on scouting and recruitment and, along with a Yale economics graduate Peter Brand, sparked a paradigm shift in the sport.

Beane recruited players based not on their perceived talent or value, he merely factored in what the numbers reported and this induced recruitment of undervalued players that were supposedly unorthodox. Nevertheless, Beane and Brand believed in their sabermetric method and stayed the course. After initial hiccups, their numbers-based model paid dividends. Ultimately, the Oakland Athletics won 20 consecutive games, the longest winning streak in American League history.

Moneyball extols the virtues of risk-taking, going against the grain, challenging prevailing practices. If a specific method has never been tried, it also means it has never failed; innovation is the bane of failure. As Edison famously said about his failed attempts to bring the light bulb to life”:

“I have not failed 10,000 times. I have successfully found 10,000 ways that will not work.”

The Wolf of Wall Street (2013)

“I partied like a rock star, lived like a king,” wrote former Wall Sreet broker Jordan Belfort in his autobiography. Visionary director Martin Scorsese’s adaptation of Belfort’s book, The Wolf of Wall Street, is more a cautionary tale than an aspirational one. The movie depicts Belfort’s (Leonardo DiCaprio) exceedingly decadent lifestyle and its repercussions.

Belfort’s silver tongue and apathy for financial laws saw his firm Stratton Oakmont scale unfathomable heights. However, both firm and Belfort were under the surveillance of the FBI and the Securities Exchange Commission (SEC). Eventually, Belfort’s gold-plated house of cards collapsed and he was condemned to three years in prison. Belfort currently plies his trade as a motivational trainer.

The Wolf of Wall Street does a marvellous job of highlighting Belfort’s various shades of personality. While his affinity for rampant corruption and hedonism are deplorable qualities, his immense entrepreneurial drive and a proclivity for hard work are ideals to aspire to. Further, the movie portrays the toxic element of the ‘success at all costs’ attitude predominant in Wall Street and numerous large-scale corporations.

However, the exuberant debauchery and glamour camouflage a potent admonition of greed and vanity. Jordan Belfort, the protagonist of this narrative of extravagance, is a perplexing personality. A man bestowed with the gift of gab and an entrepreneurial mind, he, much like Icarus, fell prey to hubris and flew too close to the sun.

12 Angry Men (1957)

Spoilers for the film’s ending below.

Negotiation, leadership, team-building, and analysing behavioural patterns are fundamental business techniques. 12 Angry Men, a courtroom drama directed by the late great Sidney Lumet, is a masterclass in imparting those techniques and deciphering the elusive art of persuasion.

Twelve unnamed Jury members assemble to deliberate the case of an 18-year-old Hispanic boy charged with stabbing his father to death.

In the United States, to decide on criminal cases ordained by a jury, the verdict must be unanimous. In the movie’s context, this meant that all twelve members must reach the same decision. 11 men find the defendant guilty, but Juror 8 (Henry Fonda) is the sole holdout. The story thus proceeds as Juror 8, wielding his innate understanding of human behaviour and group dynamics, sows doubts in the minds of the other jurors. Juror 8’s approach is neither manipulative nor nefarious, but it proves to be very effective. Towards the conclusion, all 12 jurors agree the boy isn’t guilty.

12 Angry Men elucidates on the intricacy of group dynamics. It also spells out the skills required to be a competent communicator. During the film, the jurors that shape opinion and carry weight are the ones who remain calm and conduct themselves with grace; the others gravitate towards them. Educators and CEOs cite this movie as essential viewing for businessmen.

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