Sometimes, however, the best takeaways can be found in fictional form – especially when Hollywood is involved. To prove it, we’ve compiled a list of the best entrepreneur movies that every aspiring business owner should watch, from real-life biopics to guerilla documentaries.
Inspiring, practical and often thought-provoking, these films will undoubtedly make you reflect, no matter where you are on your entrepreneurial journey, so get the popcorn ready and start making notes.
The Founder (2016)
With a strong focus on the ownership wrangling that defined McDonald’s’ early years, you could be forgiven for thinking that The Founder is simply a Social Network for the fast food industry. At its heart, though, this 2016 offering is less corporate drama and more character study, highlighting the dedication, persistence and, indeed, ruthlessness that is often needed to succeed in business.
The titular founder in question is Ray Kroc, a struggling 1950s door-to-door salesman who stumbles upon the original McDonald’s restaurant – and with it, an opportunity to find his own fortune by franchising it. Based on Kroc’s real-life autobiography, it pulls no punches; the man himself is not a particularly likeable or moral operator, remarking at one point that “contracts are like hearts – they’re made to be broken”. It does, however, illustrate how running a business can turn ugly when it reaches a certain size, as well as how single-mindedness and perseverance are the secrets to winning – no matter how ugly the victory.
Now, I know what you're thinking. How the heck does a 52-year-old, over-the-hill milkshake machine salesman build a fast food empire with 16,000 restaurants, in 50 states, in 5 foreign countries, with an annual revenue in the neighborhood of $700m? One word: persistence. Nothing in this world can take the place of good old persistence. Talent won't. Nothing's more common than unsuccessful men with talent. Genius won't. Unrecognized genius is practically a cliché. Education won't. Why the world is full of educated fools. Persistence and determination alone are all powerful.
The Inventor: Out for Blood in Silicon Valley (2019)
While most of the films on this list depict entrepreneurial success, The Inventor, a 2-hour HBO special first aired in 2019, is a fascinating insight into what happens when things go horribly wrong.
Produced and directed by Oscar-winning filmmaker Alex Gibney, it details the spectacular downfall of Stanford dropout Elizabeth Holmes, and her company Theranos. Having attracted over $90m in venture capital during the late 2000s, the company’s technologies and practices were found to be fraudulent, resulting in the dissolution of the company (Holmes and her former COO, Ramesh Balwani, are set to stand trial in 2020, with both facing up to 20 years in prison).
Through expert and insider testimonies, the film paints a picture of Homes’ wannabe visionary style – particularly her preoccupation with branding, marketing and media over actual product development (Holmes is regularly seen wearing a black turtleneck in imitation of her idol, Steve Jobs). In the end, though, The Inventor is about more than a narcissist with noble but flawed vision; it is a warning to entrepreneurs everywhere – and indeed Silicon Valley as a whole – that you should never believe your own hype, especially at the expense of the truth.
Stories have emotions that data doesn't, and emotions get people to do all kinds of things – good and bad.
Written, directed by and starring Jon Favreau, Chef is a less cynical insight into entrepreneurship, yet it still manages to tap effectively into the frustration that many workers feel in their nine-to-five job.
Favreau’s Carl Casper is a successful and prestigious chef pigeon-holed into serving mediocre fare, before a public argument with a food critic results in the collapse of his professional career. Naturally, Casper then proceeds to “find” his true sense of happiness, purchasing a small food truck and travelling the length of the country with his young son.
While some may find the story a little too saccharine, it nevertheless illustrates that, for many people, professional and personal fulfilment comes from going it alone and having the freedom to do what we love. This is a valuable reminder to not just aspiring business owners, but those further down the line who may have forgotten precisely why they took that entrepreneurial plunge in the first place.
I may not do everything great in my life, but I'm good at this. I manage to touch people's lives with what I do.
The Startup Kids (2012)
Crafted by two Icelandic entrepreneurs, Vala Halldorsdottir and Sesselja Vilhjalmsdottir, The Startup Kids is an exploration of the entrepreneurial mindset and lifestyle, structured through a series of interviews with real-life startup founders.
Funded entirely by Kickstarter, the film features thoughts and insights from successful tech entrepreneurs such as Drew Houston (Dropbox), Zach Klein (Vimeo) and Alexander Ljung (SoundCloud), as well as numerous venture capitalists, investors and industry insiders. Unsurprisingly, there is a wealth of inspiration, advice and – importantly – warning to be found in among the 55-minute running time, with Halldorsdottir herself remarking that the documentary is intended to motivate and enlighten aspiring young entrepreneurs.
I don’t know why anybody thinks that startups are all rainbows and sunshine.
Office Space (1999)
A satirical and somewhat fantastical take on the sheer boredom and inanity of the corporate workplace, Office Space is a walking, talking 90-minute reminder of why you left the nine-to-five behind. There’s more to Mike Judge’s cult classic than soulless bosses and violently dismantled photocopiers, though; for business owners, Gary Cole’s Bill Lumbergh is a masterclass in how not to manage your people.
While humiliating, degrading and undermining your workforce might not result in them hatching a plan to steal from you (or, worse, burn your office down), the film does illustrate how talented but disengaged employees are bad for business. If you’re not paying attention to morale, then there’s a good chance that you’re creating exactly the kind of working environment parodied here, which should be a frightening thought in itself.
The thing is, Bob, it's not that I'm lazy; it's that I just don't care. It's a problem of motivation, all right? If I work my ass off and Initech ships a few extra units, I don't see another dime, so where's the motivation?
The Wolf of Wall Street (2013)
Notwithstanding the graphic decadence and debauchery on offer in Martin Scorsese’s 2013 masterpiece, The Wolf of Wall Street is a worthy watch for aspiring entrepreneurs for one iconic reason: “sell me this pen”.
In this one almost throwaway exchange, Jon Bernthal’s Brad succinctly identifies the difference between a natural entrepreneur and the hundreds of hopeful (but hopeless) average Joes who just don’t understand the basic business tenet of supply and demand. It’s a humorous scene but one that perfectly illustrates the sales-oriented mindset of a successful entrepreneur.
Despite the extremely skewed moral compass of Leonardo DiCaprio’s Jordan Belfort, there are even some inspiring lessons to take away, too. As Belfort tells his fanatically loyal workers, “the only thing standing between you and your goal is the bulls**t story you keep telling yourself as to why you can’t achieve it” – a pearl of wisdom that every aspiring business owner should contemplate.
The name of the game – moving the money from the client's pocket to your pocket.
The Intern (2015)
In the annals of cinema history, there have been some truly great mentors: sages of truly timeless wisdom, such as Yoda, Mr Miyagi or Morpheus. But unless you’re training to fight evil Sith lords, neighbourhood bullies or rogue post-apocalyptic robots, it’s difficult to place the importance of mentorship in a startup context – unless, that is, you’ve seen The Intern.
Focusing on the relationship between Anne Hathaway’s stressed-out entrepreneur and Robert De Niro’s retirement-averse titular intern, the film slowly but gradually illustrates the benefit of having an experienced mentor behind you. It also touches on many of the challenges that a small startup typically faces, and how having a steady hand to advise you can loosen the weight of running a company. If nothing else, The Intern has a lot of smart things to say about the modern workplace, a lot of which is still relevant in 2020.
Mark Zuckerberg never brought in a CEO - and he was a teenager!
If you're still looking for more great movie recommendations, then why not take at our list of the best leadership films, too - or, if you prefer your entertainment in chunks, the best business TV shows?
In the meantime, what other movies about entrepreneurs would you recommend? Let us know your picks in the comments below.