Business Lessons from The Sopranos.

For those of you who are unaware, “The Sopranos” is a classic American television series. It’s a show about many things, family, business, and relationships. I don’t like when people refer to the show, a show about the Mafia. For me, it’s a show about family. A family who, through generations, happen to be apart of the Italian-American Mafia.

There are two series that (I believe) are excellent in regards to life, business and family. The first is “The Sopranos”, and the second is “Breaking Bad”.

“The Sopranos” has literally redefined television as we know it. It has broken all rules, and set new standards for television excellence. Everything is flawless, the writing, directing, and for me, most of all, the acting.

Watching this show you’ll find yourself realizing that these characters are NOT real. The acting tricks you into thinking there is a real Tony Soprano, or any character. This show is also very versatile. Some people don’t watch the show because it’s violent, it’s not all about the violence, it’s about business, family, and many deeper things that all depend on what you, as a fan see.

In this post, I will like to emphasize the connections and lessons that one can learn about the world of business from that show. As they are particularly memorable and substantive.

On Opportunities;

In the show episode “Down Neck”, Tony Soprano starts to remember his childhood. He remembers when he first discovered that his father was part of the mafia, and he remembers how his parents interacted with each other.

Tony’s family told him that his dad was “in Montana being a cowboy” when he was in jail. Sometimes you just have to laugh and cry at the same time, you know?
Tony’s family told him that his dad was “in Montana being a cowboy” when he was in jail. Sometimes you just have to laugh and cry at the same time, you know?

In the first season episode, Tony remembers a fight that his father had with his narcissistic mother. The fight was an argument between his mother and his father. You see, his father had a “ground floor” opportunity to move to Reno and set up Mafia operations there with a long-time associate.

His mother, always negative and demanding, refused to let him go. She carried on so. She was relentlessly negative and even threatened to take the children and flee if he left.

Eventually she won.

It’s discovered later that were his father to listen to himself and not take the counsel from his narcissistic wife, that the entire family would be billionaires now.

Tony Soprano's father and uncle "Junior".
Tony Soprano’s father and uncle “Junior”.

This is a scene that has played out countless times throughout history. It is one where the father; a “breadwinner” for the family wants to seize an opportunity, but his partner refuses.

It’s a case, some might argue, that a “bird in the hand, is better than two in the bush”.

But, is it actually true?

Is it true in every event, all the time?

Tony Soprano as a young boy watching his father.
Tony Soprano as a young boy watching his father.

What is different is that when opportunities present themselves to the family “breadwinner” it is of a different form that a mere “pipe dream“. For it involves the labor and reward structure for the person who has the idea.

The difference here is that it’s not just an idea, and not just a dream. It’s a business opportunity that involves work alongside people that you know, and (perhaps) trust.

Look, if you have a dream, it’s up to you to follow it.

If you have a dream, you must follow it. Not wait for the approval of others.

Do not be held back by others, especially those you love and care for. Your selection of life partner (husband or wife) will have the biggest impact on your overall satisfaction in life. It will be more influential than anything else.

Look, if you have a dream, it's up to you to follow it. Do not be held back by others, especially those you love and care for.
Look, if you have a dream, it’s up to you to follow it. Do not be held back by others, especially those you love and care for.

Speaking about relationships…

On client relationships:

"When you're bleeding a guy, you don't squeeze him dry right away. Contrarily, you let him do his bidding, suavely. So you can bleed him next week and the week after, at minimum."

Let’s look at a tale of two designers.

One designer (Mr. Bob) was determined to maximize the profit of every project he undertook. Now this isn’t at all easy. He had to haggle over each and every charge and task into great detail and often was involved in seemingly endless arguments. He nick-picked every cent, and argued every clause.

You don't want to bleed a guy out all at once. You need to handle him suavely.
You don’t want to bleed a guy out all at once. You need to handle him suavely.

This quest was accompanied by massive arguments with clients, and yes the occasional lawsuits that would manifest from time to time.

On the other hand, (Mr. John) is a completely different designer with a completely different temperament.

Instead of fighting “tooth and nail” over every single point and issue, he would do the opposite. He tended to concede every (more or less) reasonable point to his clients. Of course, he would end up making less on each job. In fact, he would sometimes even lose money from time to time.

Which one never had repeat business? Which one worked with the same clients for decades?

Take a guess.

Do not fight over every last concession. Build a partnership of mutual respect, and bleed him slowly on your terms.

Of course, clients don’t want to be bled, but they do appreciate a little suaveness.

James Gandolfini is mesmerizing as Tony Soprano, a lynchpin in the Italian Mafia. However, instead of seeing Tony as just a one-dimensional thug, we see that he has a life outside of his criminal activities, and that's what makes this show different from it's competition. It's a different side to the story of criminals, that they have normal lives when not breaking the law.
James Gandolfini is mesmerizing as Tony Soprano, a lynchpin in the Italian Mafia. However, instead of seeing Tony as just a one-dimensional thug, we see that he has a life outside of his criminal activities, and that’s what makes this show different from it’s competition. It’s a different side to the story of criminals, that they have normal lives when not breaking the law.

On creative road-blocks:

"My advice? Put that thing down awhile, we go get our joints copped, and tomorrow the words'll come blowing out your ass."

Paulie’s advice to frustrated amateur screenwriter Christopher is classic. It is pretty much exactly the same as every book on creativity ever written.

Sometimes you all just need to have your joints copped, and enjoy yourself.
Sometimes you all just need to have your joints copped, and enjoy yourself.

If you’re struggling with a problem, put it aside and inspiration will come when you’re not expecting it.

While it may not be possible to follow Paulie’s prescription to the letter… heh heh … the idea that you need to reset your brain is always good strong advice.

Sometimes you all just need to have your joints copped, and enjoy yourself.

The show is mainly about Anthony "Tony" Soprano and his life as a father, husband and leader of a mob in the 21st century. The show is (as far as I know) realistic, compared to many other mafia shows and movies I have seen. The actors fit like a glove to their parts. This show made me realize how good many of these actors are in other shows and movies. This show has it all; humor, action, drama, good music, good actors, good "behind the camera" people and a good plot. The show displays all sides of the mob business; "business", private life, the cops/FBI point of view, the victims side of the story and much more.
The show is mainly about Anthony “Tony” Soprano and his life as a father, husband and leader of a mob in the 21st century. The show is (as far as I know) realistic, compared to many other mafia shows and movies I have seen. The actors fit like a glove to their parts. This show made me realize how good many of these actors are in other shows and movies. This show has it all; humor, action, drama, good music, good actors, good “behind the camera” people and a good plot. The show displays all sides of the mob business; “business”, private life, the cops/FBI point of view, the victims side of the story and much more.

On the creative professions:

"Event planning? It's gay, isn't it?"

On The Sopranos, and within that world of Dons and “Hit Men”, interest in certain things, including but not limited to event planning, fashion design, literature, and certain psychological theories, are considered awful effeminacy.

A similar macho attitude often obtains in corporate boardrooms when it comes to design, and other creative professions.

A lot of executive decision makers are comfortable with spreadsheets. Show them colors and shapes, on the other hand, and you can see the panic in their eyes.

When dealing with people of different interests and backgrounds, you need to understand that not everyone views things from the same point of view. Part of being a success is making these other fellows comfortable with their “softer” sides.

You need to deal with people on THEIR terms.

While the show has often been criticized for the negative stereotype of Italian-Americans as mafiosi, and to an extent this is undeniable, I can see so many positives from the show. The portrayal of strong family values, friendships, love and compassion; could this be present in a coarse television show about gangsters? Yes. Furthermore, other burning issues are discussed such as terrorism, social inequality and injustice, homosexuality, drugs etc. This is no shallow, dull show about tough guys and violence. It has so much more. Many of the issues we see on the show are very real.
While the show has often been criticized for the negative stereotype of Italian-Americans as mafiosi, and to an extent this is undeniable, I can see so many positives from the show. The portrayal of strong family values, friendships, love and compassion; could this be present in a coarse television show about gangsters? Yes. Furthermore, other burning issues are discussed such as terrorism, social inequality and injustice, homosexuality, drugs etc. This is no shallow, dull show about tough guys and violence. It has so much more. Many of the issues we see on the show are very real.

On professional behavior:

"You don't think. You disrespect this place. That's the reason why you were passed the fuck over."

There is a reason for corporate dress, behavior and career advice. It is a tool that separates the janitor and street garbage man from the corporate division head, and the board-room .

To fully appreciate this difference not the level of respect that the most successful people in a company place on behavior and relationships. Those that mast that behavior end up mastering that environment.

Corporate dress, behavior and career advice are tools that separates the janitor and street garbage man from the corporate division head, and the board-room .
Corporate dress, behavior and career advice are tools that separates the janitor and street garbage man from the corporate division head, and the board-room .

Corporate dress, behavior and career advice are tools that separates the janitor and street garbage man from the corporate division head, and the board-room .

On appropriation:

"Fuckin' expresso, cappucino. We invented this shit. And all these other cocksuckers are gettin' rich off us."

"Oh, again with the rape of the culture."

By his own admission, Howard Schultz was inspired by the coffee houses of Venice and Milan when he created his own little version in Seattle.

This image is just some people having a meal together right? Yet the context, and the situation, along with the understated currents running through the series creates a masterfully powerful image.
This image is just some people having a meal together right? Yet the context, and the situation, along with the understated currents running through the series creates a masterfully powerful image.

The designers of the graphical use interface at Apple were influenced by work developed at Xerox’s Palo Alto Research Center.

And some people think that the Flintstones are just the Honeymooners except set in the Stone Age.

Imitation, influence, and iteration are crucial to design development. The only requirement is that the goal is transformation, not replication.

 The Sopranos really approaches the bloodthirst of the Gods, their cruelty, their indifference to mere mortals...and their so, so human traits mixed in with their almost unbearable inhumanity. But don't forget they sometimes show great wisdom and kindness too. The Gods and the Sopranos mingle with us mere mortals, but we say a little prayer of thanks when they pass us by. They know things we don't.
The Sopranos really approaches the bloodthirst of the Gods, their cruelty, their indifference to mere mortals…and their so, so human traits mixed in with their almost unbearable inhumanity. But don’t forget they sometimes show great wisdom and kindness too. The Gods and the Sopranos mingle with us mere mortals, but we say a little prayer of thanks when they pass us by. They know things we don’t.

Do not try to replicate. Try to transform.

On the unintended consequences of technology:

"It sounds to me like Anthony Jr. may have stumbled onto existentialism."

"Fucking internet."

Okay, advanced technology may have introduced the idea of a godless universe to the Soprano household. Many American software engineers, however, believe that advanced technology is our best proof that God exists — and that He lives in Cupertino, California.

Sure.

What ever you say.

It's just "a guy" arguing around some cardboard boxes. Right? The proper use of technology AT ALL LEVELS can create a unique and powerful venue for other purposes. You need to be able to master your craft and do so carefully.
It’s just “a guy” arguing around some cardboard boxes. Right? The proper use of technology AT ALL LEVELS can create a unique and powerful venue for other purposes. You need to be able to master your craft and do so carefully.

Technology is a double-edged sword. Use it carefully.

On commitment:

"I  came home one day, shot her four times. Twice in the head. Killed her  aunt, too. I didn't know she was there. And the mailman. At that point, I  had to fully commit."

If you’re going to make something big, make it really big. If you’re going to make it simple, make it really simple.

Or really small, or really fancy.

Any thing worth doing is worth doing well.
Any thing worth doing is worth doing well.

If you’re going after a project, if you’re trying to win a competition, if you’re serious about getting the job done, don’t bother unless you’re willing to fully commit.

On bacon and eggs;

The Chicken was involved, but the pig was committed.

Any thing worth doing is worth doing well.

On aesthetics:

"Not in the face, okay? You give me that? Huh? Keep my eyes?"

Designers like to think that it’s not about how it looks. It’s about how it works, or how it communicates, or how it changes the world. All true, except it’s also about how it looks.

Have some dignity even through the worst of life.
Have some dignity even through the worst of life.

The artifacts we make are the Trojan Horses that deliver our ideas to an unsuspecting public. Making them look beautiful — or engaging, or funny, or provocative — is anything but a superficial exercise.

We all get whacked now and then. Just make sure you get to keep your eyes.

Have some dignity even through the worst of life.
Have some dignity even through the worst of life.

On pizza

Take that shit outside! Don't ever disrespect the pizza parlor.

-Christopher Moltosanti, after getting his button in season 3

What does pizza have to do with design? What doesn’t pizza have to do with design.

Never forget the importance of pizza.

Never forget the importance of pizza.
Never forget the importance of pizza.

Keeping our creative focus:

"I'm not a cat! I don't shit in a box!" 

Uncle Junior’s response to using a bedpan. Sometimes we got to breakout of what’s expected of us and maintain some dignity.

If anyone here thinks the Sopranos is just about murder and the mafia then it skimmed over your head completely.

The pleasure of watching this show is that the barrier of the TV screen protects us. I think the writers are constantly reminding us of the moral dimension involved. The Sopranos is at the bottom of it, deeply moral. It's about actions, and codes. If you get hung up on the violence, you probably had better watch something else and leave it at that. Go drink some Kool Aid and chill.
The pleasure of watching this show is that the barrier of the TV screen protects us. I think the writers are constantly reminding us of the moral dimension involved. The Sopranos is at the bottom of it, deeply moral. It’s about actions, and codes. If you get hung up on the violence, you probably had better watch something else and leave it at that. Go drink some Kool Aid and chill.

On choice:

 "There's an old Italian saying: you f--k up once, you lose two teeth." 

Adriana in the clutches of the FBI and this time they get very serious after she is filmed disposing evidence of a crime.

She admits that Matoush the drug dealer killed someone in her office and she cleaned up after the fact even though the killing had nothing to do with her.

The FBI tell her that unless she can get Christopher to flip, she will be arrested and charged.

She tells Chris what’s happened and he tells her they’re both dead and have no way out of the predicament she’s put them in…

"That's a bad decision."

It’s gone. Black. Nothing.

The world of “The Sopranos” was never kind to a rat, even when it was our beloved Adrianna. After revealing to Christopher that she was an informant for the Feds, Adrianna met her demise. Christopher informed Tony, who had Silvio take Adrian for a ride in what may have been the show’s best episode – “Long Term Parking.”
The world of “The Sopranos” was never kind to a rat, even when it was our beloved Adrianna. After revealing to Christopher that she was an informant for the Feds, Adrianna met her demise. Christopher informed Tony, who had Silvio take Adrian for a ride in what may have been the show’s best episode – “Long Term Parking.”

When does Adriana know she’s going to die?

Is it when Silvio drags her out of the car, pulling her into the isolated woods, so she can crawl away from him pitifully? Is it when he pulls over, not at the hospital, but in the middle of nowhere?

Is it on the car ride over there, when she hears him talking about how resilient Christopher is—and must realize on some level that he’s talking about how Christopher will be in the wake of her death, not after the foiled suicide attempt that was the excuse to get her in the car?

“Heartbreaking” is the word that kept popping up in online forums in the days after this episode aired.  Probably no Sopranos episode  pulled at the heartstrings like “Long Term Parking” did.  

I remember  two or three weeks after Season 5 ended, I caught myself moping around  the house, feeling kinda down.  This in itself was not very surprising—I  always went through a period of withdrawal after a season wrapped up.   But I felt particularly raw that summer of 2004—and then I realized what  it was: 

I was still bummed out over the death of Adriana LaCerva.

I’m not normally prone to overly  emotional responses to the deaths of fictional characters.  So why was I  so downcast over the demise of this big-haired Jersey girl?  The  answer: because David Chase wanted me to be.  

“Long Term Parking” is a  powerful, resonating hour in and of itself, but much of its resonance  also comes from its connections to long-running threads, associations  and images from over the course of the series.  Some of the bells that  ring in this hour are set off by mallets that began their swing years  ago.  Almost everything in this episode—every twist, every scene, every  line of dialogue—is anchored to something that we’ve viewed or heard or  understood in previous episodes.  

If we are shaken by “Long Term  Parking,” it is because the hour taps so deeply into our experience of  being embedded in SopranoWorld over the last 5 seasons. 

- Long Term Parking (5.12) 

Is it when Tony first calls her and tells her Sil is on his way to take her to the hospital? Is it when Christopher gets up and says he needs to clear his head before they make any big moves? Or is it when the FBI tells her it’s time to wear a wire or get Christopher to turn—or go to jail?

Me, I think Adriana realizes what’s happening on that car ride to the woods.

Adriana realizes what’s happening on that car ride to the  woods.
Adriana realizes what’s happening on that car ride to the woods.

You see Drea de Matteo’s face, and there’s a moment where her tears switch over from tears for Christopher to tears for herself, for the life she’s never going to get to lead (even if that life might have involved getting fat and moon-faced or watching Christopher grow a horrifying mullet and mostly ignore their kids as they race through a gas station parking lot).

I suspect that she knew all along this was one possible way this car trip would end.

The one-way car trip.
The one-way car trip.

I expect that she knew fairly soon into it that option B—the one ending in her death—was a larger possibility than she wanted to admit. But there’s this moment of perfect, crystalline acting, when you can see the switch flip, and you can see she knows what’s about to happen.

It would be a mistake to classify Adriana as innocent—she’s clearly culpable in the various bad things she’s done over the years, and she knows more than she lets on to the FBI.

Adriana realizes what’s happening on that car ride to the  woods.
Adriana realizes what’s happening on that car ride to the woods.

But she’s an innocent, someone who’s just a little bit naïve and lacks the sense of, say, Meadow, who ostensibly knows enough to flee this life. This life is all Adriana has ever known, and it’s all she will ever know, and even as she paints a vision for Christopher of the life they’ll lead together away from New Jersey, it seems like some part of her doesn’t really believe it, even as the rest of her is giving the hard sell.

So that leaves Adriana, in a car, somewhere on the highway in the wooded landscapes of New Jersey.

Adriana's last moments in the words of New Jersey as the leaves fall all around them.
Adriana’s last moments in the words of New Jersey as the leaves fall all around them.

The leaves are falling, and a song about California’s on the radio, and she’s imagining a point where she simply skipped town, ditched the two warring factions in her life that almost never saw her as a human being.

(The mobsters, ultimately, treat her more warmly than the FBI does, on average.)

She looks out the window, and she thinks back on everything that led to this point, all of the moments in her life that got her into this car, with the man rambling endlessly about how her fiancé is going to bounce back.

And she knows.

And it all blows away like ashes.

Mistakes, in business, can be fatal.


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