4 Movies Every Entrepreneur Should Watch

The following four films fall into this category, and I
believe that all entrepreneurs can find something of
value to take from them:
1. Steve Jobs: The Lost Interview
One movie that first comes to mind as a good reference
point for entrepreneurs is The Lost Interview of Steve
Jobs. It’s a particularly helpful documentary for people
who are interested in starting a technology company, but
there are also valuable lessons here for all
entrepreneurs. The beauty of the documentary is in its
simplicity. In fact, it’s a stretch to even call it a
documentary; it’s better described as a largely unedited,
hour-and-a-half conversation with Steve Jobs.
I realize in advance that Steve Jobs tends to be a
controversial figure, to the point that even mentioning
his name provokes strong reactions. However, I would
like to strip away popular impressions of the man from
the quality of what he has to say in this interview. In the
film, Jobs talks very candidly, through a blend of
personal anecdote and philosophy, about the core things
necessary to start and run a successful company. One
of the things that strikes me is his ability to focus on
product quality and content as the single most important
ingredients in a company’s success. While this seems
obvious, he has an unusual ability to explain it clearly
and in a manner that resonates. The interview also
serves as a fascinating character study, having been
conducted shortly after Apple fired him as CEO back in
the 90's. He speaks with remarkable candor in the film,
making for a highly watchable and engaging
documentary.
Related: The 9 Biggest Financial Warning Signs
2. Tucker: The Man and His Dream
Another film that I’d recommend to entrepreneurs is
Tucker , which stars Jeff Bridges as Preston Tucker, a
car-manufacturing entrepreneur from the 40s. The
movie, directed by Francis Ford Coppola, is less than a
documentary but more than a typical Hollywood script. I
first saw this film in the late 80s, when I was starting
my first “big boy” company, and it gave me a glimpse at
the zeal and energy that true entrepreneurs possess.
Tucker’s enthusiasm is electric and contagious in the
film. On the flip side, the story also graphically, and
somewhat depressingly depicts the struggles that Tucker
faced in trying to compete with the auto giants in Detroit.
In a way, it can give the quintessential big-picture optic
of what it’s like to dream and start a company, spanning
across the full spectrum of emotions involved.
3. Startup.Com
Startup.com is a documentary about govWorks, a failed
startup company from the dotcom-bubble era. The
filmmakers were granted an astonishing level of access
to the company and its leadership, providing a fly-on-the-
wall perspective of a company’s meteoric rise and
abrupt fall.
The film can, in many ways, be considered a companion
to Paul Hawken’s Growing a Business . While Hawken
provides a roadmap for running a business successfully,
Startup.com is a one-stop shop in how not to start and
run a business. The film portrays the company’s
leadership as more concerned with fluff than substance,
the antithesis of the Steve Jobs portrayed in The Lost
Interview. We see the founders raising huge sums of
money and hobnobbing with Bill Clinton, while, right
under their noses, the company’s infrastructure and
product quality is collapsing. Any experienced
entrepreneur will totally empathize with the stupidity of
the entrepreneurs (since we all have made similar
mistakes), but somehow the mistakes are grandiose and
larger-than-life in scope. There’s something in this film
for every kind of entrepreneur. For seasoned business
owners it may provoke a sense of self-reflection and
humility, and budding entrepreneurs can learn from the
mistakes made by the film’s protagonists.
4. Man on Wire
The last film that I recommend is, on a superficial level,
totally unrelated to entrepreneurship. Man on Wire tells
the story of Philippe Petit, a career tight-rope walker who
wants to apply his trade on an extraordinary scale:
walking from one of the World Trade Center’s towers to
the other on a wire. The story involves the intricate plans
among the conspirators to achieve this highly illegal and
unsanctioned feat in the early 70's. To any reasonable
person, there’s no logical end point to Petit’s entire
project. Even when he attempts to describe the
motivation behind walking between the two towers, it
sounds highly whimsical. He does it, simply, because he
wants to. This deeply resonated with me as a business
owner, because, in a way, starting a business takes a
similar mindset. As an entrepreneur, you have a song
you want to sing, and you simply have to sing it, even if
it makes no sense to anyone else. It’s comforting to
know that there are others out there who share this kind
of instinct.