8 documentaries every entrepreneur needs to watch
Saturday nights have long had their own ritual in my house: documentary time!, a slot marked in red on the calendar, complete, of course, with an exclamation mark. Over the years, the time I once set aside for going out and flirting late into the night has become my only free window for revisiting favourite documentaries and discovering new ones. I’m not particularly romantic, romantic comedies don’t appeal to me, and fiction isn’t a genre I often turn to either. In film, as in literature, I’m much more drawn to so-called case study formats: real stories that offer insight into different aspects of life, encourage us to learn from other people’s experiences and introduce us to perspectives we may not have considered before.
With most people in my close circle currently venturing into entrepreneurship for the first time, taking their first steps with their startups and developing their own business ideas, entrepreneurship has become a subject I increasingly explore, both personally and professionally. Two Saturdays ago, I became so absorbed in documentaries about entrepreneurship and business that I spent six hours in front of the screen almost without noticing. One title led to another, and most of the films I watched that night, along with those I return to from time to time, have made it onto this list.
Whether you’re just starting out on your own business journey, thinking about launching your own company or simply interested in stories about people who have dared to work for themselves, these documentaries offer insight into the entrepreneurial ecosystem: from big ideas and business successes to misjudgements, uncertainty and challenges that are less often discussed. For the full experience, I suggest having a pen and paper ready.
Documentaries about entrepreneurship we’re adding to our must-watch list
Steve Jobs: The Man in the Machine
One of the first people who comes to mind whenever documentaries about entrepreneurship come up is undoubtedly Steve Jobs, the man who co-founded Apple and changed the way we use technology. Although several documentaries and feature films have been made about this visionary, innovator and one of the most influential entrepreneurs of our time, my particular pick is Alex Gibney’s 2015 film Steve Jobs: The Man in the Machine. The film goes beyond his business achievements and technological innovations to explore lesser-known aspects of Jobs’s personality, his management style, his treatment of employees and the impact his ambition had on those around him. Through interviews with colleagues, friends and people who knew him, the documentary examines the line between genius, ambition and obsession, offering a different perspective on the man behind one of the world’s most recognisable technology brands.
The Inventor: Out for Blood in Silicon Valley
Another Alex Gibney film I would include on this list is 2019’s The Inventor: Out for Blood in Silicon Valley. I admit that, to me, the story of Elizabeth Holmes is one of the most extraordinary examples of how far ambition and the desire for success can go, particularly when there is no substance behind the promises. Holmes managed to persuade some of the most influential figures in business to invest in her company, Theranos, presenting technology that was supposed to make it possible to run numerous blood tests using just a few drops. She was publicly compared to Steve Jobs, and her image as a young entrepreneur poised to transform the medical industry further fuelled interest in the company. Yet the technology turned out not to work as claimed, while investors, employees and patients were subjected to deception. Through accounts from former employees, investigative reporting and company materials, Gibney traces the rise and fall of Theranos, while showing how the promise of a revolutionary innovation became one of Silicon Valley’s biggest business scandals.
Startup.com
Released in 2001 and directed by Chris Hegedus and Jehane Noujaim, Startup.com offers insight into the entire process of building a startup: from developing a business idea and raising initial capital to expanding a team, managing a company and navigating market challenges. The documentary follows two friends, Kaleil Isaza Tuzman and Tom Herman, who decide to launch the technology company govWorks.com. Their idea was to give citizens easier access to local government services, from paying parking fines to applying for various permits online. At the height of thedot-com boom, the company quickly attracts around $60 million in investment and grows to more than 200 employees. However, rapid growth also brings serious challenges: technical difficulties, mounting competition, financial pressures and disagreements between the founders that ultimately threaten the company’s survival. The film raises important questions about business partnerships, the division of responsibilities, capital management and the sustainability of a business model, showing how much an initial vision can change when confronted with market realities.
Generation Startup
Generation Startup is one of the documentaries I enjoy returning to because every viewing reveals anew just how much more complicated the journey from a good business idea to its successful execution is than it initially appears. Directed by Cynthia Wade and Cheryl Miller Houser, the 2016 film follows six young people in Detroit who decide to try their hand at entrepreneurship after graduating from university. Over a year and a half, we follow their attempts to turn their ideas into sustainable businesses, find investors, define a strategy and cope with the uncertainty of starting a company. Its approach is somewhat reminiscent of Startup.com, as it focuses not solely on the final results but on the process of building a business, with all the successes, misjudgements and obstacles encountered along the way. Unlike the story of govWorks.com, however, this film follows several different ventures, offering insight into different ways of thinking about entrepreneurship.
American Factory
The Oscar-winning American Factory (2019) certainly deserves a place on this list. The first documentary from Higher Ground Productions, the production company founded by Barack and Michelle Obama, it won Best Documentary Feature at the 2020 Academy Awards. Directors Julia Reichert and Steven Bognar document the story of Chinese billionaire Cao Dewang and his decision to take over a former General Motors factory in Dayton, Ohio, and begin manufacturing automotive glass under the name Fuyao Glass America. The factory’s reopening brings new jobs and hope to the local community, but the arrival of Chinese management soon raises questions about differing business cultures, working conditions, productivity and union organising. At the heart of the film are the challenges of managing a company in a foreign market, from reconciling different business cultures and working standards to balancing management’s business objectives with employees’ needs.
General Magic
The story of General Magic is one I enjoy returning to; I have already watched the documentary of the same name three times, each time fascinated by the fact that, back in the 1990s, the team was working on technology we now associate with smartphones. The 2018 film, directed by Sarah Kerruish and Matt Maude, takes us back to the period when a group of former Apple employees founded General Magic, a startup with ambitions to develop the first pocket-sized communications device combining the functions of today’s smartphones. Its founders and team members included some of the most talented people in Silicon Valley at the time, among them Andy Hertzfeld and Bill Atkinson, who had previously worked on the development of the Macintosh computer. Their project, the Magic Link device, was unveiled in 1994 but failed to achieve the commercial success they had hoped for. Although the company eventually ceased to exist, its ideas and technological solutions anticipated many of the functions we now associate with smartphones. For me, the most interesting part of this story is that General Magic did not lack vision; its technology simply reached the market before the market was ready to embrace it. For anyone currently developing their own business, this documentary can be particularly useful because it highlights that a good idea and technological innovation are not enough on their own: understanding the market, recognising the needs of future users and judging the right moment to launch a product are equally important.
Jiro Dreams of Sushi
The much-loved business and entrepreneurship documentary Jiro Dreams of Sushi (2011) takes us away from the world of technology startups and Silicon Valley and into the kitchen of one of the world’s most highly regarded sushi restaurants. Directed by David Gelb, the film tells the story of Jiro Ono, the celebrated Japanese sushi master and owner of Tokyo’s Sukiyabashi Jiro, which once held three Michelin stars. His restaurant seats just ten guests and is located in an underground station, yet it was here that Jiro built a reputation that placed him among the world’s most respected restaurateurs. His business philosophy rests on an extraordinary dedication to his craft, a careful selection of ingredients, an uncompromising insistence on quality and the constant refinement of his product. From an entrepreneurial perspective, Jiro’s story is particularly interesting for the way he built a recognisable brand without needing to expand the business. His example highlights what often forms the foundation of long-term success: product quality, consistency and continued investment in what sets a business apart from its competitors.
Something Ventured
Finally, Something Ventured (2011) tells the story of investors whose decisions played an important role in the creation and development of some of today’s most influential technology companies. Directed by Emmy-winning filmmakers Dan Geller and Dayna Goldfine, the documentary traces the development of Silicon Valley’s venture capital industry through the experiences of investors who recognised the potential of companies such as Apple, Intel, Genentech and other technology pioneers. Archival footage and investors’ accounts offer a closer look at the circumstances in which some of the most significant technology companies of the second half of the 20th century emerged, from initial discussions about potential investments to decisions that could change an entire industry. For entrepreneurs considering seeking investors, it is particularly useful to understand the criteria behind investment decisions. Something Ventured reveals what investors see in business ideas and their founders, why trust and the ability to lead a team are just as important as the quality of a business plan, and how much the relationship between an investor and an entrepreneur can influence a company’s subsequent development.
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