The best movies about real business, not Hollywood’s idea of business

Cover of "Jerry Maguire"

Eric Ries likes to asks audiences who has seen a movie about a startup.  Normally everyone has seen “The Social Network”. But, quoting a recent profile:

“Perhaps Ries’ most important message was that the same democratization of entrepreneurship has been tied to a glorification of the profession. His description of the films “The Social Network” (as a modern image) and “Ghostbusters” (as an “old school” image) illustrated entrepreneurs building from the ground up.

“He described the Hollywood recipe. Act 1: a protagonist with a bold idea and excellent timing for the idea. Act 2: a brief montage focusing on the struggles on writing code or battling some ghosts. Act 3: a tidy conclusion featuring earning tons of money or saving lots of people.

“But Ries, an expert on startups, revealed the uncut version—the vast majority of a startup experience lies in Act 2. He then asked why it doesn’t make it into the movie. His answer? It’s too boring. He admitted no one would want to watch a seven-hour fight with his cofounders.”

In the real world, the montage is where ff Venture Capital and our founders live.  What movies actually show what happens in the montage, where companies get built?

Media and entertainment is a $1.9 trillion global industry, but I find most of the content is, well, misleading.  I googled ‘best business movies’, and was disappointed in what I found.  I’ve found many movies that are set in a business setting, but most are wildly unrealistic about how business actually works.  In the real business world, there are definitely a lot of funny moments, but they don’t usually involve vicious mocking of other people (the preferred mode of humor of many movies).  In the real world, there’s very little sex in business (although I heard rumors about a certain Bear Stearns conference room).  There’s little violence, except sometimes the verbal kind.  And the people are dramatically less attractive.  Movie protagonists may work in business, but the plot usually has nothing to do with how business works.  Wall Street (1 and 2), Wolf of Wall Street, etc., are about aberrations, not the norm.

Similarly, the typical romance movie is: boy meets girl, boy has fight with girl, boy & girl make up and live happily ever after…. as opposed to the real way people find a spouse.  “Love Actually” shows the exact opposite of love, actually.

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Over the years I’ve collected a short list of movies which I think relatively accurately reflect how business and people function, and which you can learn from.  This is an amazingly short list, when you consider how fecund the media industry is.  What other movies do you recommend?


Boiler Room – Newbie learns how to sell stocks. Meaningful insight into how sales (and greed) works; some irrelevant sex and violence thrown in to sell tickets.

The Company Men* – employees of a large company get outsourced.

The Devil Wears Prada* – young woman comes to New York and scores her dream job as the assistant to one of the world’’s biggest fashion magazine editors, but struggles to balance the demands of her new role with her prior identity and relationships.

I Don’t Know How She Does It – A working mother at a financial management firm, struggles to juggle marriage, children, and a high-stress job. When she earns a new account that requires frequent travel and her husband receives a promotion, both spread themselves thin to achieve their career goals.  The film highlights the double standards applied to many women.  (referral from Raffi Sapire)

Bitch in Business – Hilarious music video about life as a woman in business; I know numerous women who’ve received feedback verbatim like that in the video (NSFW).

Glengarry Glen Ross – brilliant film which will teach you a lot about sales

The Imitation Game* – Profile of Alan Turing, a brilliant mathematician who’s clueless about humans; I’ve met many people “on the [autism] spectrum” in the tech industry. (Similarly, Adam is a unique realistic romance film about a man with Asperger’s Syndrome, which we really liked; if you work in tech, this will give you insight into some of your coworkers.)

Jerry Maguire: A sports agent is fired from a prestigious sports management firm after pulling an all-nighter to draft and distribute a mission statement to the whole Company detailing how they should be doing business. Faced with the sudden termination and loss of clients, Maguire starts up his own sports management firm with only one client employing the values expressed in his ‘mission statement’.  (Suggestion from Herb Moore.)

Julie & Julia – a half-documentary about Julia Child, a pioneering female entrepreneur.  It’s also one of the very rare Hollywood movies that accurately portrays a happy marriage.  Having a strong personal relationship makes running a company much easier…and your relationship with your business partners has many parallels with a marriage.

Margin Call – impressive debut film about the 2008 financial crisis which accurately captures the culture of both Wall Street and large corporations in general.

12 Angry Men – A single man persuades a jury to collectively change their mind about the guilt of an alleged criminal.  The movie has some valuable lessons in persuasion; I saw this as part of a business school case study.

El Metodo (The Method) – Spanish movie about a job interview.  I loved this movie, which brutally but realistically displays corporate politics.  It has one totally extraneous sex scene which doesn’t fit the plot at all, which was clearly thrown in because someone thought it would sell more tickets.

Office Space – Comedy about a widely hated company in the midst of downsizing many of its staff; this classic movie resonates with a lot of people. (Referral from Daniella Norwood, my web designer, owner of Ella J Designs.)

The Reluctant Fundamentalist – Drama about a young Pakistani man chasing Wall Street success.  Illustrates an inner conflict between his American Dream, a hostage crisis, and the enduring call of his family’s homeland. (referral from David Frankel)

Up in the Air – a HR professional spends virtually all of his time traveling for business; this is a great movie of what your life will be if your #1 priority is work



Here are a few documentaries I recommend which show what happen in the montage:

Barbarians at the Gate – fictionalized version of the battle for RJR Nabisco

Food Inc. – if this doesn’t make you follow a Michael Pollan diet, nothing will

The Insider –  profile of Jeffrey Wigand, a tobacco whistleblower – a realistic movie about an unrealistic era: the first dot-com bubble

Office Tigers* – Profile of my former client, OfficeTiger, a pioneer of the Indian outsourcing industry*

The Triumph of the Nerds: The Rise of Accidental Empires* – explores the development of the personal computer in the United States from WWII to 1995

Rogue Trader – about former derivatives broker Nick Leeson and the 1995 collapse of Barings Bank

Salesman* – the life of the door-to-door salesman

Something Ventured: Risk, Reward, and the Original Venture Capitalists* – history of the VC industry

The Big Short

Too Big to Fail – Portrays the financial crisis of 2008 and the powerful men and women who decided the fate of the world’s economy in a matter of a few weeks. Provides a behind the scenes look as to how some of America’s most impactful decisions were made.  (referral from David Frankel)


One other category of movies I’m particularly interested in are science fiction movies which realistically show the foreseeable future.  I’d highlight:

Black Mirror* – the dark side of science and tech.  Very, very dark.

Her – romance between a man and a machine (voiced by Scarlett Johansson) set in the not-distant future, which is realistic about men, women, romance, and machines (except in the real world, Scarlett would have had a perfectly realistic video avatar synced to her voice)

Minority Report – Spielberg specifically tried to display technologies which realistically could be developed in the near future, and he succeeded

* = I haven’t watched the film personally, but have had it recommended to me

Update: I was also recommended to see The Founder and The Banker (Apple film).

 Cross-posted in Forbes.

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