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6 Unique + Motivational Movies for Entrepreneurs

By September 7, 2017 No Comments

Hollywood (and everyone else) loves glamorizing the underdog, showing off a lead characters struggle to the top and end result of amassed riches (Scarface, Blow, Wolf of Wall Street), but my favorite are the less extravagant and off the beaten path blockbusters.

Sure, you can find a motivational story in almost anything you can stream on Netflix or Amazon Video, but here’s my top list of movies you must watch. I spout references all day, usually to people who have no idea what I’m talking about, I can nearly recite some of these movies from start to finish, for good reason. Get familiar with these and get some inspiration and memorable quotes to throw around at your next sales pitch or to remind you to get your ass moving on your next lazy day.

#6 – Limitless

PG-13 | 1h 45min | Mystery, Sci-Fi, Thriller | 18 March 2011 (USA)


Limitless is a movie about wonder drug ‘NZT’, which turns Bradley Cooper from sloth-like “writer” into a stock trading, multi-language comprehending, upper class genius. It’s a dream drug and has, in my opinion, inspired a market of scammy ‘nootropic’ drug makers to come out of the woodwork, claiming to make you smarter and more focussed from some FDA un-approved pill.

The movie, though not sales related, is motivational, when he starts on the pill, he realizes how lazy he’s been and how he hadn’t been taking advantage of any of his potential, we don’t need (or have) NZT to realize this about ourselves, to start moving on a project, to finish tasks we put off, or to get our ass in gear on something we have always wished to do.

#5 – Catch Me If You Can

PG-13 | 2h 21min | Biography, Crime, Drama | 25 December 2002 (USA)

Allegedly based closely on the life of Frank Abagnale Jr., one of the most infamous con artists, Catch Me If You Can is full of quick wit and comedic sales pitches. I’m not talking product sales, but self sales. Leonardo DiCaprio swindles his way into millions of dollars of forged checks, a Pan Am airline pilot, a lawyer, and more, while constantly being pursued by the FBI. 

A lot of scenes in the movie seem to be inspired by the famous quote, “act like you’ve been there before”, which is something we all need when giving sales pitches, put on the spot in a meeting, or entering uncharted territory.

#4 – Glengarry Glen Ross

R | 1h 40min | Crime, Drama, Mystery | 2 October 1992 (USA)


One of the most famous sales movies of all time, with a bill featuring Al Pacino, Alec Baldwin, Ed Harris, Kevin Spacey, and others, you’re thrown into the world of high pressure real estate sales, the struggle of the typical suited salesmen, and the high brow ‘made it’ salesmen trying to get a fire started with a group of seemingly helpless real estate sales men at a small firm.

Plenty of scenes really drive home the difficulty and ever shifting world of sales in this Oscar nominated classic, one of the most memorable above (be wary of a few cuss words and homophobic slurs, in 1992 things were a little different, apparently). Ask anyone in a sales position that’s over the age of 30 and they’ll recite their favorite lines from Glengarry.

#3 – The Founder

PG-13 | 1h 55min | Biography, Drama, History | 20 January 2017 (USA)


The Founder is about the meteoric rise of the world’s largest fast-food chain, “McDonald’s”. Originally founded by two bothers and essentially taken over by a man named Ray Krok. The movie covers Ray’s initial struggles as a door to door salesmen and failed inventor, to his ruthless takeover of the business from the McDonald brothers and his ultimate rise to insane levels of success.

The first quarter of the movie covers the typical door in face situations most struggling salesmen go through, the rest though provides a great amount of motivation and troubleshooting of things as shown above, even the way the McDonald brothers went about creating their first successful restaurants’ floor plan and work flow is interesting and insightful.

The sad story of the McDonald brothers is a great lesson, don’t get into business with snakes, cover yourself any way you can, yet if you have an idea, have the motivation and desire to succeed, don’t let a few ‘minor details’ get in your way. Absolutely worth watching!

Entrepreneurial Quote: 
Ray Kroc: While you two boys were content to sit back and become a couple of also-rans… I wanna take the future. I wanna win. And you don’t get there by being some “aw shucks” guy sap. There’s no place in business for people like that. Business is war. It’s dog eat dog, rat eat rat. If my competitor were drowning, I’d walk over and put a hose right in his mouth. Can you say the same?
Mac McDonald: [pause] I can’t. Nor would I want to.
Ray Kroc: Hence, your single location.

#2 – Tommy Boy

PG-13 | 1h 37min | Adventure, Comedy | 31 March 1995 (USA)


Being born into a family of entrepreneurs and succesful business people, I can strangely relate to the world Chris Farley is in, Tommy Boy. Being apart of an established name is hard, especially when you’re on the outs of the business, or started late, or are thrown into a tough spot you know nothing about. No, this isn’t a joke being placed at #2.

The comedy hits the struggle of being a salesmen competing with big players hilariously yet accurately. Above is a clip we are all familiar with, trying to get a ‘yes’ from a bunch of cold called ‘no’ men who are already set in their ways. Though the scene is hilarious, that awkward sense of failure bleeds through the screen.

#1 – Boiler Room

R | 2h | Crime, Drama, Thriller | 18 February 2000 (USA)

One of my all time favorite movies, business related or not, and totally under the radar to pretty much everyone, Boiler Room. When I got my first ‘sales’ job at West Business Services right out of highschool, after my first day of training I was told to watch this TWICE before coming back the next day. I obviously had no problem watching a movie with young Vin Diesel, Ben Affleck, Scott Caan, Jamie Kennedy, and Giovanni Ribisi?!

Tons of quotes are totally memorable and inspiring, my favorite scene is above, one of which I’ve made a half-assed attempt to replicate after being sucked into a MLM presentation (sorry, Balky). There’s a few scenes with sales calls and training that though are totally unethical and never going to really happen in real life, get you ready for whatever comes your way on a call or in person.

Entrepreneurial Quote: There is no such thing as a no sale call. A sale is made on every call you make.

Either you sell the client some stock or he sells you a reason he can’t. Either way a sale is made, the only question is who is gonna close? You or him?

Now be relentless, that’s it, I’m done.

Almost-made-it’s: Wall Street, Jerry Maguire, Thank You for Smoking, Money Ball, The Company Men, Cedar Rapids, Blow, Wolf of Wall Street, Two For The Money, The Big Kahuna.

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