This article is also published on

For the up-and-coming entrepreneur, it might be best to sit back and gather some information from the greats before going out into the world. Reading is one of the best ways to gather such information, but to really hammer home the core values, it’s best to try to gather that information from a different medium. Thus, the following list sets out to find the six best books of all time for entrepreneurs, as well as their film adaptations. These two companions will allow both the up-and-coming entrepreneur, as well as the experienced entrepreneur, to gather information and relax at the same time.

So, without further ado, let’s get started.

Glengarry Glen Ross (1992)

In 1984, David Mamet won the Pulitzer Prize for his play, Glengarry Glen Ross. Spanning the course of two days, the play details the lives of four desperate Chicago real estate agents who need to sell undesirable real estate to unwitting prospective buyers. It’s a difficult task to be sure, but these agents are prepared to engage in any number of unethical and illegal acts.

Based on Mamet’s experience of having previously worked in a similar office, the story shows entrepreneurs that they are not alone in the hustle and bustle of what happens when tough times come along. The play is available for purchase and can be read at anyone’s leisure, allowing time to study it line by line.

Plays are, however, a visual medium. While there are few recorded versions of the play available, there is the 1992 film adaptation available, also written by David Mamet. Filling itself with a colorful cast of characters, the film is a home run.

What happens when everything goes wrong? How do last year’s mistakes affect this year? When the pressure of earning a living becomes overwhelming, this book and its adaptation are there to remind the entrepreneur that they walk on a busy street.

The Aviator (2004)

The shadows of the giants of industry loom large over the public. Even as their names slip away, their achievements stay cemented in the public’s consciousness. This requires large leaps in the aviation field and large leaps in putting planes on film.

This film shows the steps taken by the great Howard Hughes. However, the true man remained a shadowy figure until Charles Higham’s renowned celebrity biography shined light upon him.

In Howard Hughes: The Secret Life, Higham compiles painstaking research into the paint of his compelling portrait of a unique American figure. It’s an unforgettable story that shows that the man behind the business, the entrepreneur’s true face, is often not a pleasant one.

For those who want to take another step in the madness of Howard Hughes, renowned director Martin Sorcese walks in the steps first walked by Charles Higham in The Aviator. Instead of a canvas, the film is a snapshot of the highs and lows of Howard Hughes’ life and mind. Beyond Hughes’ luxurious lifestyle and flings with iconic women, it wasn’t all fun and games. Any entrepreneur should take heed of Howard Hughes’ story, especially those who think success is the key to all of their problems.

There Will Be Blood (2007)

Before venturing into their business, every entrepreneur should be aware of what might become of their family. What will become of your children? What will they think of you?

The worst case scenario is depicted in Upton Sinclair’s novel, Oil! While being an old book first published in 1926 and already nearing a hundred years old, it’s a timeless tale that follows the son of an oil tycoon whose sympathies lie in his father’s workers. Instead of stopping there, the book expands and becomes a satire, featuring a cavalcade of characters, including senators, oil magnets, Hollywood film starlets, and a crusading evangelist. It’s the dream cast of characters for any entrepreneur, but at its heart is the disillusioned son of an entrepreneur.

Taking heed of this novel’s warning, Paul Thomas Anderson brought us There Will Be Blood. Starring Daniel Day Lewis, the film is about an entrepreneur making his way into the oil industry on a quest for wealth during Southern California’s oil boom. While Daniel’s son does appear here and there, the film keeps its focus on the oil tycoon, a hardened entrepreneur who will stop at nothing.

For the modern day entrepreneur, this film and the book that it’s loosely based on might seem to be out of date. However, it’s a timeless cautionary tale when ambition meets stubbornness and how the line between right and wrong is often a gray sea.

The Pursuit of Happyness (2006)

Never give into despair. No matter how bad things get, always look ahead, and always have a plan of action.

This is the advice of Chris Gardness. In his autobiography, he details how at the age of twenty and just out of the Navy, he traveled to San Francisco and set his sights on the competitive world of high finance. After landing a job as an intern at a prestigious brokerage firm, things began to slide downhill fast. A single father, Gardner, found himself on the streets with a very young son. Through ambition and by the grit of his teeth, Gardner transformed himself from being one of the city’s invisible people to one of its greats. In his autobiography, read through his life’s story and what went on in his head.

Once you’re finished reading the book, look at Gardner’s life from an outside perspective. The film adaptation will help you do that. Starring Will Smith in an early dramatic role, the film goes hand in hand with the book. Both book and film are a triumphant call for all entrepreneurs to never give up, always have a plan, and always have pure intentions.

The Wolf of Wall Street (2013)

Every entrepreneur dreams of making it big. How they get there and what they do with that money is up to them, but there’s no shame in longing for the fantasy of spending money like there’s no tomorrow, taking obscene amounts of drugs, and having pretty women on your shoulders at any given moment. However, before these fantasies take a hold of you, it’s best to take a step back and have a reality check.

Unfortunately, Jordan Belfot did none of these things. In his autobiography, he details the inner workings of his Wall Street firm and how he won gold but ended up spending twenty-two months in prison. He lived the dream but woke up in turmoil. Any entrepreneur would do well to take heed of his story and read about his life instead of trying to make their fantasy into a reality.

However, if you’re an adrenaline junkie who needs another roller coaster, take no further look than Martin Sorcese’s The Wolf of Wall Street. Plus, if you loved The Aviator, you’ll love how Leonardo DiCaprio seamlessly slides from Howard Hughes to the slimy Jordan Belfort.

As an adaptation of Jordan’s autobiography, the film is a heart pounding experience from beginning to end. It’s also a cautionary tale for entrepreneurs to not let their fantasies take hold of them.

Steve Jobs (2015)

Any entrepreneur should, at the very least, be aware of the great men and women who came before them. Afterall, why walk down the beaten road when you can take the road that is less traveled? Plus, gaining a few ideas and insights from those who came before never hurt anyone.

There is no larger giant in the tech industry whose shadow looms larger than Steve Jobs. Unfortunately, he never sat down and wrote us an autobiography. However, Walter Isaacson, a professor of history at Tulane, CEO of the Aspen Institute, chair of CNN, and editor of Time, took the time to write down this biography on Steve Jobs.

Based on more than forty interviews with the face of Apple himself, which were conducted over two years, plus several more interviews with more than a hundred of his family members, friends, adversaries, competitors, and colleagues, this biography is the definitive one. Being comprehensive yet easy-to-follow, Steve Jobs: The Exclusive Biography offers a riveting ride into the life of one of the most creative entrepreneurs of the modern times.

The book was such a hit that screenwriter Aaron Sorkin and director Danny Boyle took a crack at the story, and in 2015 audiences were thrown back with Steve Jobs. Starring Michael Fassbender, the film gives audiences of all shapes and sizes and from all walks of life an indepth look at three pivotal points in Jobs’ life. With these sequences, Steve Jobs both grows into the iconic figure the public knows him by and fails to live up to those expectations. For any entrepreneur, it’s a reminder that the looming shadows of the greats belong to people who were just like them once upon a time.

Let these cautionary tales hit your heart. Never let ambition cloud your judgment, never think money will solve all of your problems, and always remember to stay virtuous. Above all, let these other stories inspire you to achieve more than you originally set out to. You might surprise yourself.

Photo by Timothy Eberly on Unsplash

Leave a Reply