Greatest Business Lessons in Gangster Movies
Everyone loves a good gangster movie. The best ones are packed full of criminals who are ruthless, cunning and sometimes downright vile. But they know how to get the job done. At least until they're sent to the pokey or snuffed out.
Before then, they run successful businesses, make tons of cash and create empires. While the enterprises are illegal, it is possible to take their unethical behavior, flip it, and learn something.
These are the best business lessons from notorious fictional gangsters. See how they translate into the real, slightly more ethical world we live in.
'F*** You, Pay Me.'
Where it's from: Goodfellas
Who said it? Henry Hill (Ray Liotta)
The scene: A restaurant owner, hard up for cash after the unwillingness of Tommy (Joe Pesci) to pay his own tab (and also beating the poor guy in the head) makes a deal with mob boss Paul Cicero (Paul Sorvino) for protection. Big mistake.
Ray Liotta, as Henry Hill, voices over the iconic scene while liquor is being moved in and out of trucks.
"Now the guy's got Paulie as a partner. Any problems, he goes to Paulie. Trouble with a bill, he can go to Paulie. Trouble with the cops, deliveries, Tommy, he can call Paulie. But now the guy's got to come up with Paulie's money every week. No matter what.
Business bad? F*** you, pay me. Oh, you had a fire? F*** you, pay me. The place got hit by lightning, huh? F*** you, pay me."
Watch part of the scene.
Business Advice From Henry Hill and the Goodfellas
People are always looking for free business, and this is the mantra that everyone has to live by.
It's especially true of freelancers, who are often asked for free samples, favors or low-buck spec work that should be paid for. Ditto with attending meetings and doing research. And who can forget about being paid in exposure? F*** you, pay me.
Science fiction author and freelance writer John Scalzi has a wonderful blog post/rant about the topic that's pretty well-known among the freelance writing community. It's titled "A Note to You, Should You Be Thinking of Asking Me to Write For You For Free." Here's a taste:
"Did you wake up this morning and say to yourself 'You know what? A New York Times bestselling author who has been working full-time as a writer for two decades, who frequently rails at writers for undervaluing their own work in the market and who is also the president of a writers organization that regularly goes after publishers for not paying writers adequately is exactly the person who will be receptive, through lack of other work or personal inclination, to my offer'? And if you did, what other dumb things did you do with your morning?"
You should read the whole thing. Trust us. This is one offer you don't want to refuse.
'A Man Who Doesn’t Spend Time With His Family Can Never Be a Real Man.'
Where it's from: The Godfather
Who said it? Vito Corleone (Marlon Brando)
The scene: In one of the early scenes from "The Godfather," Vito Corleone chastises and slaps Johnny Fontane (Al Martino) for crying and not acting "like a man." He then asks him if he spends time with his family. Johnny responds with a yes.
"Good. Because a man who doesn't spend time with his family can never be a real man," the Godfather responds, dusting off the singer. He tells Fontane he would make the Hollywood big wig giving him trouble "an offer he can't refuse."
Watch this scene from "The Godfather."
Sage Advice From Vito Corleone
Casting the whole "real man" part aside, the core of this quote has to do with the importance of being at home, present, and spending time with loved ones.
It's an especially important piece of work and business advice in the digital age, where work follows us from the office to the bathroom at home thanks to smartphones and virtual work platforms like Slack.
All work and no play won't just make a person boring. Overwork can be bad for your health. So remember to unplug every once in a while.
'It's Not Personal, Sonny, It's Strictly Business.'
Where it's from: The Godfather
Who said it? Michael Corleone (Al Pacino)
The scene: After being beat up by a corrupt police captain, a bruised Michael Corleone calmly talks about shooting him at a restaurant. His reaction is in stark contrast to the hotheaded Sonny (James Caan), who is ranting and raving about taking revenge. Michael echoes this later in "Godfather III" when advising his nephew to never hate his enemies.
It's one of the greatest scenes in "The Godfather" trilogy, marking Michael's entrance into the criminal world, and you can watch it here.
Michael Corleone's Sage Advice, Applied to Business
If there were an official ranking of most-used quotes about business from any movie, this would be number one. Often quoted as "Nothing personal, it's just business" (a saying allegedly coined by a mob accountant), this is a pretty self-explanatory phrase but an important one.
If you find yourself getting too worked up about a work-related matter, just repeat the phrase in your head. On the flip side of things, the advice also applies if you need to do something for work that will upset someone else.
This quote has some deeper meaning as well. Because of the serious delivery of the words by Al Pacino in the movie, the sarcasm of the line gets overlooked. Of course, making his bones was going to be personal for Michael. Just like everything he did in the family business from that point forward.
In fact, in the book by Mario Puzo, Michael did say it was personal, and not business, to Tom Hayden (Robert Duvall), after Capt. McCluskey broke his jaw.
"Tom, don’t let anybody kid you. It’s all personal, every bit of business. Every piece of s*** every man has to eat every day of his life is personal. They call it business. OK. But it’s personal as hell. You know where I learned that from? The Don. My old man. The Godfather. If a bolt of lightning hit a friend of his the old man would take it personal."
At the same, there can be value in getting personal with team members to build trust, rapport and empathy, and behind any successful business is a line of professional personal relationships.
'Whenever Anybody Says They're a Little Concerned, They're Very Concerned'
Where it's from: The Irishman
Who said it? Frank Sheeran (Robert De Niro)
The scene: Whispers (Paul Herman) orders Frank Sheeran to burn down a laundromat in Delaware. De Niro, in a voiceover, says, "Whenever anybody says they're a little concerned, they're very concerned. ... And if they say they're more than a little concerned, they're desperate."
Watch the scene.
The Wisdom of Frank Sheeran, Applied to Business
While the stakes in "The Irishman" are high — that laundromat almost gets Sheeran killed — and mobsters in Martin Scorsese movies like to talk about felonies with the casualness of ordering dinner, there's some good advice here for the real world.
At work, if a boss or higher-up says they're "a little concerned" about something, your ears should perk up. What's the issue and how do you deal with it?
And if they're "more than a little concerned," take a lot of notes.
'The Guys That Last in This Business Are the Guys Who Fly Straight. Low-Key, Quiet. But the Guys Who Want It All, Chicas, Champagne, Flash — They Don’t Last.'
Where it's from: Scarface
Who said it? Frank Lopez (Robert Loggia)
The scene: After Tony Montana (Al Pacino) strikes a deal with Alejandro Sosa (Frank Shenar) without Frank Lopez's consent and then tells Frank to expand his business, Frank gives Tony these words of advice. It's advice that, had Tony listened, he still would be alive.
Of course, Frank later tries to kill him, so it's also a warning.
Frank Lopez's Sage Advice, Applied to Business
This is one of those pieces of advice about not burning the candle at both ends. It's also a good tip to not spend beyond your means, spend on a flashy new car to impress your coworkers, or burn all your money on hookers and blow.
For this example, we'll look to Travis Kalanick as a cautionary tale. Kalanick was forced to step away from Uber as CEO amid claims of rampant sexism, where he fostered a virulently toxic work culture and generally was "a terrible person" (his own words used to describe himself, allegedly).
Of course, he still got the golden parachute, because that's how CEOs roll. But if you don't have access to that, as most of us don't, then it's not a good idea to introduce these life choices into your career path.
'I Don't Want To Be a Product of My Environment. I Want My Environment to Be a Product of Me.'
Where it's from: The Departed
Who said it? Frank Costello (Jack Nicholson)
The scene: It's the first line of dialogue in the film, spoken by Frank Costello (Jack Nicholson) in a brief, racist monologue.
The Rolling Stones' "Gimme Shelter" plays in the background while we're introduced to the sociopathic Costello.
The opener also shows us a young Colin Sullivan (Matt Damon's character), whom Costello is grooming to become his mole in the Boston Police Department.
Check out the film's entire five-minute opening scene.
Terrible Business Advice From Frank Costello
Speaking of workplace culture, the sentiment that the environment being a product of one's actions is something that every founder and manager should consider.
In Costello's case, he's a paranoid lunatic who fosters a culture of fear and double-crossers. Take away the guns and the drugs. and put him in the role of CEO or a top-level manager, and you'd get the same results (just a lot less murder, hopefully).
Managers and bosses need to be careful about what kind of expectations, attitudes and standards they tolerate and don't tolerate, as it will shape workplace culture. And some CEOs are so toxic that they hire toxic people, creating a completely noxious space to work at. Those are the places normal, non-toxic employees want to avoid.
'Nobody Knows Anybody. Not That Well.'
Where it's from: Miller's Crossing
Who said it? Tom Reagan (Gabriel Byrne)
The scene: Tom Reagan plants seeds of doubt with mobster Johnny Caspar (Jon Polito) about his trusted hitman, the Dane (J.E. Freeman), telling him "Nobody knows anybody. Not that well."
Simple and Sound Advice From Tom Reagan
In the context of the film, the quote is more than a bit sinister. Outside of the film and in a general context, it's philosophical. Just how well can we truly know someone else? But in the context of the workplace, it's pretty straightforward.
Generally, no one in the office really knows one another. Sure, everyone might get along and be friendly, but coworkers mostly remain coworkers. It's a good reminder not to get too comfortable and say something that might offend someone or be taken the wrong way.
'Brand Names Mean Something, You Understand.'
Where it's from: American Gangster
Who said it? Frank Lucas (Denzel Washington)
The scene: When Frank Lucas learns that Nicky (Cuba Gooding Jr.) is diluting his very popular of brand of heroin, Blue Magic, he confronts him about it and tells him to change its name to something else.
"Brand names mean something, you understand," says Frank. "Consumers rely on them to know what they're getting. They know the company isn't going to try to fool them with an inferior product. They buy a Ford, they know they're gonna get a Ford. Not a f***in' Datsun. Blue Magic is a brand name, as much a brand name as Pepsi. I own it. I stand behind it. I guarantee it and people know that even if they don't know me any more than they know the chairman of General Foods."
Sound Business Advice From Frank Lucas
The fascinating thing about "American Gangster" is that Frank takes actual business principals and applies them to the selling of heroin. It's like it elevates him above common criminals. One minute he's talking about ethics and the importance of hard work, the next he's blowing a hole in a guy's head on a crowded street.
There are a lot of business lessons in the film, and Frank's brief explanation about branding is one of the better ones. Some brands produce so many things they try to get by on brand name alone, but they also manufacture so many types of products that their brand name is weakened.
Keep quality paramount across the board and establish trust with the consumer.
'Never Hate Your Enemies. It Affects Your Judgement.'
Where it's from: The Godfather: Part III
Who said it? Michael Corleone (Al Pacino)
The scene: An old Michael Corleone says this to his nephew, Vincent Corleone (Andy Garcia), while the younger mafioso is raging about his intents to whack rival mob boss Joey Zasa (Joe Mantegna).
Watch the scene.
Michael Corleone's Sage Advice, Applied to Business
The third "Godfather" film might not be in the same league as its predecessors, but it's still not absolutely terrible. And it has some good old family business advice as well.
In work, there's no point to actually hating anyone or anything — an annoying coworker, boss or even a rival company. It'll just fog up your mind while you try to approach a problem or strategy to deal with that person or thing.
And who wants to carry around that extra baggage on the soul? There are more pressing matters to worry about, fix, and go home.
'In the Casino, the Cardinal Rule Is to Keep Them Playing and to Keep Them Coming Back. The Longer They Play, the More They Lose, and in the End, We Get It All.'
Where it's from: Casino
Who said it? Sam "Ace" Rothstein (Robert De Niro)
The scene: In one of the earlier voiceover scenes in "Casino," Ace explains the concept of "whales" (high rollers) while the camera focuses on a businessman who wins hundreds of thousands at a baccarat table but goes home empty-handed.
Advice from Ace Rothstein
Every casino is designed to part people from their money and, much more often than not, go home with less money than they arrived with.
While that's true for any business selling something, the quote also doubles as advice for keeping repeat customers — keep them coming back for whatever it is you offer. That could be consulting services, articles, marketing — anything you can do to show value.
Unless you're a payday loan company, this advice isn't as drastic as it is in the film, but it's worth remembering.
'Don't Get High On Your Own Supply.'
Where it's from: Scarface
Who said it? Tony Montana (Al Pacino)
The scene: Immortalized in Biggie Smalls' "Ten Crack Commandments," the original line comes from Elvira (Michelle Pfeiffer) during a scene at a nightclub.
Frank Lopez is rambling about lessons, the first being to "never underestimate the other guy's greed." Elvira then chimes in with, "Lesson two: Don't get high on your own supply."
Frank eyes her and mutters about how some people don't follow that rule.
Elvira's Advice for Budding Entrepreneurs
Let's be honest here. Tony is a terrible businessman, and Elvira doesn't seem to have worked a day in her life, so taking advice from them isn't the best idea. But still, the idea of not using your own product is a sound one.
It can also be applied — with a bit of a stretch — to understanding the product you create. If you're making something addicting, like a social media platform, you might not want to use it. Many social media executives don't put their digital footprint on Facebook, Twitter or other social media planforms.
OK, mainly this applies to drug dealers, but ... you gotta start somewhere?
'Today They Asked Us to Get Rid of Joe. Tomorrow, They Ask Me To Get Rid of You. Is That OK With You? 'Cause It's Not OK With Me.'
Where it's from: Once Upon a Time in America
Who said it? Noodles (Robert De Niro)
The scene: Noodles is driving a car with Max (James Woods). He's angered that Max went ahead and offed someone without telling him and asks Max to consider what that might mean in the future, when the mob bosses decide its their turn.
Then he crashes the car into a lake.
Business Advice from Noodles
It's something that many workers have learned the hard way: You're replaceable.
While we're not saying every company treats its workers like faceless drones, those that do will make it apparent. People who have been with the company for years will be replaced by someone younger and cheaper.
If the turnover rate is high, keep the resume polished and keep your eye on other possible positions.
'More Is Lost by an Indecision Than a Wrong Decision.'
Where it's from: The Sopranos
Who said it? Tony Soprano (James Gandolfini)
The scene: We know this show is technically not a gangster movie, but Tony Soprano is the most realized fictional gangster of all time. How could we not include him?
On a phone call with Johnny Sack (Vincent Curatola), Soprano subtly advises Sack about a hit that Soprano called off.
It's the same phrase Carmella (Edie Falco) told him earlier.
Business Advice from Tony Soprano
The inability to make a decision in business can be a costly move (or a non-move, in this case). Not every call is the right one, but, as Tony Soprano says, more is lost by doing nothing than anything at all.
Identify goals, consider the consequences, trust your gut and just do something — just keep moving.
'I Trust You Know Two Percent of Nothin's F****in' Nothin'.'
Where it's from: "Deadwood
Who said it? Al Swearengen (Ian McShane)
The scene: It's not a gangster movie, but we'll be damned if Al Swearengen isn't one of the best gangsters in all of television history.
While conspiring to take over the Widow's (Molly Parker) claim on gold mining area, Swearengen agrees to give E.B. Farnum (William Sanderson) two percent of the claim's worth if he can complete his part of the plan.
The plan gets shaky and later on, Swearengen snaps at Farnum to remind him he won't get paid if things fall apart.
Watch some of the best of Al Swearengen in Deadwood.
Business Advice From Al Swearengen
In the show's context, Swearengen is simply reminding Farnum that he won't get paid if he can't get the job done.
But it's also a good lesson about not pushing too much when a good thing comes your way, or being too pushy when it comes to making a deal.
Don't bite off your nose to spite your face.
'If My Answers Frighten You, Then You Should Cease Asking Scary Questions.'
Where it's from: Pulp Fiction
Who said it? Jules Winnfield (Samuel L. Jackson)
The scene: Jules Winnfield (Samuel Jackson) discusses leaving the hitman business while talking at the diner with his partner, Vincent Vega (John Travolta).
Jules says he's going to leave the life and and wander the earth for as long as God tells him to. Vincent says that means Jules will basically be a bum sleeping on the street.
But Jules, convinced they were saved by God after being shot at and miraculously surviving, tells Vincent that's where he and his partner differ.
Some Parting Advice from Jules Winnfield
Business owners and entrepreneurs have to be able to ask realistic questions about their business and be able to digest uncomfortable truths. The same is true for employees and freelancers, who need to evaluate their own strengths and weakness before jockeying for a higher position or more demanding jobs.
Like we've learned from these many gangsters, evaluating your business or yourself should be done analytically. It's difficult to not take things personally, but hey, it's just business.
And if you do things right, the world could be yours.