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Top Movies & TV Shows for Entrepreneurs

Hollywood rarely gets entrepreneurship right — usually depicting only caricatures, stereotypes and exaggerations.

Below is a a fun list of movies and TV shows/episodes for entrepreneurs. Some are good depictions (or accurate parodies) of the entrepreneurial experience. Others are good examples of what NOT to do.

If you wanted laymen to know what the entrepreneurial experience was about — what movies would you recommend?

Here’s my list:

Tucker — The Man and His Dream (2002)

While this is not a top-10 list, arguably the best of the bunch is “Tucker” — because it really does show so many of the internal and external facets of building an innovative “big idea” in the face of skepticism and competition. The movie includes a healthy dose of the compromises (or trade offs) entrepreneurs sometimes have to make, in order to ensure that their bigger vision survives. And sadly, sometimes the vision survives, while the entrepreneur’s company does not.

Shackleton (2002)

Perhaps a surprising entry to some — but not to entrepreneurs who have tried to bootstrap a company through very difficult times. This is an epic (and true) tale of persistence, resourcefulness and leadership.

Silicon Valley (TV Series 2014- )

Of course. Of course. While technically this is a parody — Silicon Valley nails it. This is probably because the show is one of the few where the producers and writers actually consult with real entrepreneurs and others from the startup ecosystem.

Breaking Bad (TV Series 2008–2013)

Well, entrepreneurial talents can be applied to both good and bad pursuits. Lots of lessons here about market demands, dealing with competition and building a better product. Stellar episodes and scenes about strategy, finance, margins, hiring (and, ahem, ‘firing’), dealing with quirky founders and creatives, product positioning, etc etc. Enough lessons in this show, that I wouldn’t be surprised if someone created a college course about entrepreneurship, centered around Breaking Bad.

High Noon (1952)

Inspiration for the entrepreneur who feels like s/he’s all alone, trying to convince others that his/her innovation is going to take over the world.

The Social Network (2010)

While this has to be on the list — hopefully working entrepreneurs will point out to laymen how this movie depcits the cliches of entrepreneurship, than reality.

Pirates of Silicon Valley (TV 1999) — IMDb

Forget Aston Kutcher’s “Jobs”, or that other Steve Jobs movie — Pirates of Silicon Valley is a close as Hollywood gets to telling the Silicon Valley story correctly. It really does cover the nuances and personalities quite well.

Arrested Development (TV Series 2003–2006)

Inspiration for the INTRApreneur (entrepreneur inside a corporation) — dealing with incompetence inertia and just plain stupidity.

“The Office” Michael Scott Paper Company (TV Episode 2009)

The Office is fun, but not itself inherently entrepreneurial — but the 3–4 episode arc about Michael Scott leaving the company to start his own competing venture is just classic. It’s actually not a bad example of the solo bootstrap experience and everything that can go wrong (and right).

Startup.com (2001)

A dotcom era startup — filmed (for real) as is starts, takes off and crashes and burns. This is “reality TV” for a startup. Intriguing and heartbreaking at the same time.

The Aviator (2004)

There’s just something about watching Howard Hughes that’s even more inspiring than watching Steve Jobs. Sure, he started out with an inhertance, but talk about sheer innovation, risk-taking and vision — this guy had it all.

“Seinfeld” The Voice (TV Episode 1997) — IMDb

One word: Kramerica Industries. Oh wait. That’s two words.

Cosmo Kramer and his intern — saving the world from oil spills, with a large toy balloon.

Cocktail (1988)

Honorable mention — particularly Tom Cruise’s ‘dreamer’ attitude, and also for the scene where his entrepreneurship professor trashes his business plan.

Wall Street (1987) — IMDb

Not exactly about entrepreneurship — except for the scene where young Bud Fox is struggling to get a meeting with his idol Gordon Gekko. The elation he feels when he gets his first big check: every entrepreneur should know that feeling.

Risky Business (1983)

Another Honorable Mention. Remember, young Joel was part of the “Future Enterprisers” … and he movie breaks down the essentials of product design, marketing, sales and finance (and dealing with a competitor) — and the greatest product pivot of all time.

Sometimes you you just have to say “what the f*ck”…

Barbarians at the Gate (1993)

Honorable mention. High stakes finance and intrapreneurship.

Even $20 Billion Dollar corporate dealmakers can get entrepreneurial.

Jerry Maguire (1996)

Honorable Mention. Getting fired and leaving the office in flames. Starting up and competing against your old company. Failure, and redemption. Amazing how many Tom Cruise movies show up in this list.

Moneyball (2011) — IMDb

Honorable Mention — changing the status quo is not easy, even if you are the boss. Of particular interest to those who love Growth Hacking. Metrics are everything.

12 Angry Men (1957) — IMDb

Like High Noon — except you’re locked in a room — and have to persuade 11 people who have already made up their mind.

Office Space (1999)

Honorable Mention — as a reminder for any entrepreneur who forgets why they don’t want to work for a corporation.

CJ Cornell is a serial entrepreneur, investor, advisor, mentor, author, speaker and educator. As an entrepreneur, CJ Cornell was a founder of more than a dozen successful startup ventures that collectively attracted over $250 million in private funding; created nearly a thousand new jobs; and launched dozens of innovative consumer, media and communications products — that have exceeded $3 billion in revenues.

He is the author of:The Age of Metapreneurship — A Journey into the Future of Entrepreneurship

Follow him @cjcornell



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