The Art of the Deal: Summary & Review

the art of the deal

Trump: The Art of the Deal (1987) is the autobiographical account of Donald Trump, taking us through Trump’s Machiavellian mindset and business moves as he strikes deals and grows rich.

Bullet Summary

  • Enjoy life: life is fragile and success doesn’t change that. Do what you’re passionate of
  • Do your best. And if it doesn’t work, move on without regrets
  • Promote yourself. But also make sure you deliver the goods

Full Summary

About the Author: Donald Trump is an American magnate and businessman. He started out in real estate, then expanded with media and show business, and he eventually entered politics. Some people thought his run for the presidency was in jest. It wasn’t.

Introduction: He Does It For The Pleasure

If you get the latest version the introduction is from Trump himself and he uses that space to make a political point.
I will skip that part and go straight to the juiciest bit. Here is the quote from the original version:

I don’t do it for the money. I got enough. Much more than I’ll ever need. I do it to do it. Deals are my art form. Other people play beautifully on canvas or write wonderful poetry. I like making deals. Preferably big deals. That’s how I get my kicks.

And now let’s start:

Passion For Work is Key to Success

Donald Trump opens the book by explaining how much he works.

He usually arrives at the office by 9 and leaves the office by 6. Up until here, it might sound like a typical employee workday. But he rarely stops for lunch and when he goes home, he often continues making and taking calls until midnight.
And it goes on all weekend as well.
He makes at least a dozen meetings a day and at least 50 calls.

Trump also has his own special version of “mindfulness” and focus on the present.
He says:

I try to learn from the past. But I plan for the future. By focusing exclusively on the present.

And, most of all, he wants his work to provide fulfillment. He says:

That’s where the fun is. If it can’t be fun, what’s the point.

How to Get to The Top

Trump says of his style of deal-making:

I aim very high and then I just keep pushing and pushing and pushing to get what I’m after. Sometimes I settle for less than I thought but I still end up with what I want.

#1. Deal With the Top

Trump says that at a certain point at the beginning of his career, he wondered why so many of his deals fell through.

Then he realized that it was because he wasn’t dealing with the top guys. Anyone in an organization who’s not the founder or at the top is an employee.
And employees won’t fight hard to make things happen.

They’ll speak to their boss, and if their boss says no without even looking at it, they’ll drop it.
Employees fight for their salary, bonus, or salary increase, not for making things happen.

#2. Think Big

Trump says:

Think big. I like thinking big. To me it’s simple: if you’re going to think anyway, you might as well think big. Most people think small. Because most people are afraid of success, afraid of making decisions. Afraid of winning. And that gives people like me a great advantage.

What a shark mindset.

That is why Trump didn’t exactly follow in his father’s already successful footsteps. His father was a developer of affordable and rent-controlled housing in New York boroughs.
But Trump wanted Manhattan and fifth avenue, the central locations.
He wanted to build something big and monumental.

The quote of this part:

I could earn a modest return. But then again, modest isn’t my favorite word


#3. Total Focus

Trump says that one of the keys to thinking big is total focus. He says:

I think that one of the keys of thinking big is total focus. I think of it almost as a controlled neurosis, which is a quality that I’ve noticed in many highly successful entrepreneurs.
They’re obsessive, they’re driven, they’re single-minded. And sometimes they’re almost maniacal, but it’s all channeled into their work. Where other people are paralyzed by neurosis the people I’m talking about are actually helped by it.
I don’t say this trait leads to a better life, or a happier life. But it’s great when it comes to getting what you want.

Trump is talking about the single-minded focus on “more, more, more” and “win, win, win”.

#4. Protect the Downside

If you know my summary, I rarely quote straight from a book.
And yet I find many passages of The Art of The Deal so compelling that it’s hard not to quote them.

It’s been said that I believe in the power of positive thinking. In fact, I believe in the power of negative thinking. I happen to be very conservative in business. I always go into the deal anticipating the worst. If you plan for the worst—if you can live with the worst—the good will always take care of itself

I agree, and I have grown to consider this mindset such an important part of the success that I added it to my “Ultimate Power” eBook.

Protect the downside and the upside will take care of itself

#5. Don’t Gamble

Protecting your downsides also means you don’t gamble your money.
Trump says:

People think I’m a gambler. I’ve never gambled in my life. To me, a gambler is someone who plays slot machines. I prefer to own slot machines. It’s a very good business being the house.

As Warren Buffet said: “gambling is a tax on ignorance”.

#6. Keep Your Options Open

An effective technique with which you protect your downside is by maximizing your options.
Always keep several balls in the air, says Trump, because invariably some deals won’t happen, even when they seem very promising.
And, it might happen, sometimes it won’t make sense for you to pursue a deal another ball in the air becomes more promising.

Similarly, when a deal happens he always thinks of several different approaches to make it work.

This is an exchange Trump has with a real estate broker:

Donald Trump: The bid sounds low. If you can get them higher, I might be interested.

But then, he adds:

The truth is, I really don’t wanna sell the yard at any price. To me those 100 acres overlooking the Hudson river are the best undeveloped real estate site in the world.
On the other hand, I don’t want to rule out anything.

#7. Ask Everyone for Opinion – But Not Consultants

Trump believes in his instincts and he rarely hires consultants or “number crunchers”.
While he admits they are the best in their business, he sounds slightly disparaging towards an experience he had with McKinsey for example.

On the other hand, Trump believes in asking opinion to people.
For example, if he’s thinking about buying a property he asks the people living around the area. He asks the cab drivers. He asks about crime, schools, and shops.

He says he’s learned more from conducting his own research that way than from hiring any consulting firm. That way, with a feel “on the ground”, he can then build and use his own instincts.

This approach, Trump says, is quicker and action-oriented. Consultants take a long time and a lot of money for a result that has little or no conclusions.

Further, Trump says:

When it comes to making smart decisions, the most  distinguished committee working with the highest paid consultants doesn’t hold a candle to a group of guys with a reasonable amount of common sense and a lot of money on the line.

#8. Look Out After Your Money

Trump believes in spending what you need to spend -and what you have to spend-.
But not more.

And he believes in looking after his expenses and not throwing money around.

He learned from his father that every penny counts. Because “before too long, the pennies turn into dollars.
He says:

To this day, if I feel a contractor is overcharging me, I’ll pick up the phone, even if it’s for $5k or $10k, and I’ll complain. People say to me, “what are you bothering for, over a few bucks?”…
My answer is that the day I can’t pick up the telephone and make a 25 cents call to save $10k is the day I’m going to close up shop.

And then another great quote:

The point is that you can dream great dreams. But they’ll never amount to much if you can’t turn them into reality at a reasonable cost.

#9. Take Care of Appearances

Trump makes the case that how you present your assets makes the whole difference.

I loved this quote so much that I recited it more than once in my life.
Says Trump:

I can always tell a loser when I see someone with a car for sale that is filthy dirty. It’s so easy to make it look better. It’s no different in real estate.

He then adds it wasn’t applying as much in NY where people would buy almost anything. But it’s a mistake to be lulled by good times: markets always change.
And as soon as there is a downturn, cleanliness becomes a major value.

On another occasion to make his site look busier and faster-moving, he gave the order to find all the available bulldozers and make them move around on fake tasks.

#10. Get Great People and Push Them Hard

Trump says that a huge of what brings success is getting the best people and then pushing them to do their best job.

He says:

My philosophy is always to hire the best from the best.

He adds later:

Hire the best people from your competitors, pay them more than they were earning and give them bonuses and incentives based on their performance.
That’s how you build a first class operation.

Even if his ex-wife Ivana Trump who was managing his castle, says:

The castle is doing great. But I still give Ivana a hard time about the fact that it’s not yet number one. I tell her she’s got the biggest facility in town, so by all rights it should be the most profitable.

Trump seems to have a business-like approach to his intimate relationships too. He loves the fact that Ivana is “almost as competitive as he is”, and then adds: “I can say this much: I wouldn’t bet against her”.

That’s probably not the approach for what most people would consider a good relationship.

Stick With What You Know

On a deal that seemed good on paper, Trump pulled out at the last minute because he didn’t have a good feeling about it.
He says:

That experience taught me a few things. The first is to listen to your gut, no matter how good something looks on paper. The second is that you’re generally better off sticking with what you know. And third that sometimes the best investment are the ones that you don’t make.

Get Leverage: Provide Something Others Want

Trump says that if the other party realizes how badly you want something, you’re dead.

The best place to negotiate is from a position of strength, and you get that with leverage.
Leverage means to have something the other party wants. Or better yet, needs. Or, best of all, simply can’t do without.

That’s not always the case of course, and that’s where imagination and salesmanship come in: convincing the other party it’s in his best interest to make the deal.

Trump provides a few great examples in The Art of the Deal. My favorite was his move with the founder of Tiffany.

Leverage Information Advantage

Trump was often able to scoop up deals because he had information that the other party didn’t have.

Trap Your Opponents

Then he would try to get a commitment before the other party would catch wind of the situation.

For example, when he was buying the land for Trump’s tower, he signed a letter of intent. When the seller put on the contract the usual “prior to board approval” clause, he gave it back to him saying nonchalantly that he wanted to sign the LOI to move quicker.

Then, once he had the letter of intent, he later threatened to go to court when the seller wanted to back out of the contract.

Since the seller needed cash, Trump had them.

It’s About Best Deal, NOT Location

Trump says that buying properties is not about location.
He writes:

Perhaps the most misunderstood concept in all of real estate is that the key to success is location, location, location. Usually, that’s said by people who don’t know what they’re talking about. First of all, you don’t necessarily need the best location. What you need is the best deal.

Of course, if you have a great location you might need less promotion. But a bad deal in a great location is still a great deal.
And you can further enhance an area where you’ve done a great deal with great promotion.

Trump’s Approach to HR

Trump’s philosophy is that if you catch someone stealing you must go after him very hard.

However, he made an exception once.
Here was the power move genius: Trump had an extremely capable supervisor who’d also make sure nobody under him would steal.
However, that was also because he was a con-man himself with a tendency to steal.
But Trump thought: I only need to keep an eye on him, and he would make sure everyone under him does not steal.

So he kept him on board.

How to Deal (or “use”) the Press

In the course of The Art of the Deal Trump uses and leverages the press in many different ways.
Let’s see:

#1. Spin Questions into Positives

Trump says it’s best to give truthful answers to the press and not to get defensive.

But you will always get asked tough questions, and what you do at that point is spin around your answer to give something positive.

He says:

Instead, when a reporter asks me a tough question, I try to frame a positive answer, even if that means shifting the ground.

For example, if someone asks me what negative effects the world’s tallest building might have on the West Side, I turn the tables and talk about how New Yorkers deserve the world’s tallest building, and what a boost it will give the city to have that honor again.

When a reporter asks why I build only for the rich, I note that the rich aren’t the only ones who benefit from my buildings.
I explain that I put thousands of people to work who might otherwise be collecting unemployment, and that I add to the city’s tax base every time I build a new project. I also point out that buildings like Trump Tower have helped spark New York’s renaissance

I have already noted in the past Trump used this technique in How to Win a Debate. You can see him using to defend against his allegations of sexual assault:

And of course, also check out:

#2. Promote With Bravado

Trump says he uses bravado to promote.

I play to people’s fantasies.
People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular.

Basically what he’s saying here is that otherwise timid people love a leader who sounds self-assured and larger than life.

“Playing to people’s fantasies” is a law that Robert Greene borrowed for his “The 48 Laws of Power“, by the way.

#3. Use Sensationalism for Coverage

Sensationalism and bravado will also give you bigger coverage:

They’re always hungry for a good story, and the more sensational the better (…) The point is that if you are a little different, a little outrageous, or if you do things that are bold or controversial, the press is going to write about you.

#4. Denigrate Competition

Trump says he is very competitive and he’d do nearly anything to win -without legal bounds-. Sometimes that means denigrating the competition, and that’s what he would do.

In The Art of The Deal, Trump talks about a few interesting public power moves he pulled to score a win.

In some of those cases, picking a quarrel not only served to eliminate a competitor but also to promote a site he was working on.

#5. Use Press as Pressure Point

Trump also used the press to put pressure on people.

For example, he was about to scoop up a great deal in Manhattan for a piece of land where he would later build his Trump Tower.
But rumors began circulating before he signed. He was afraid that competitors would rush in and drive up the prices.

So when the press called him up asking if he had bought, he said “yes”.

Trump also says that the press works particularly well with politicians.

How to Leverage Threats

Trump is trying to help an old woman who is about to lose her farm to bank repossession.
He calls the banker to see what he can do, but the banker replies there is nothing he can do, the farm is going to be auctioned and no one is going to stop it.

“That really got me going”, says Trump.
That’s his reply:

You listen to me, if you do foreclose, I’ll personally bring a lawsuit for murder against you and your bank on the ground that you harassed Ms Hill’s husband to his death.

All of a sudden, the bank officer sounded very nervous and said he’d get right back to Trump.
Trump says:

Sometimes it pays to get a little wild.

It does indeed.

Deliver the Goods

Trump says that a big show is important, but ultimately you also gotta deliver the good.

He uses the examples of two presidents: Carter and Reagan. They had the guts and balls of aiming high and that’s what got them there. But eventually, people started catching up on the fact there was little substance behind them.

Trump’s Not Impressed by Academic Credentials

Trump says he was not particularly impressed by academic credentials.
He realized there was nothing particularly awesome or great about his classmates at Wharton.

What he got the most out of it, was the paper degree. To Trump, it doesn’t mean much, but it means a lot to a lot of people he does business with.

Modern Art is PR

Trump tells the story of an artist friend of his and how he made 25k in a few minutes. He took buckets of paints and splashed them over canvases on the floor.

That was it.

Plenty of collectors wouldn’t know the difference between a 2 minutes splash job and paintings he really cared about.

I always thought that a lot of modern art is a con. And that the most successful painters are often better salesmen and promoters than they are artists.

Then Trump keeps joking that the art world is so ridiculous that knowing what he knew might make his paintings even more valuable. Not that he was ever going to find out anyway… People weren’t even going to be able to tell the difference.

Show Strength With Aggressive People

Trump discusses his experience with a very tough and domineering teacher in military school.
And he discusses how he “played him”.
It helped he was a good athlete -which showed competence, I’d add-.

But mostly, Trump says, he finessed him in two ways by showing:

  • He respected his authority
  • But he didn’t intimidate him

These guys go for the jugular when they smell weakness, but if he saw the strength that wasn’t trying to undermine him, he’d treat you like a man.

Testing People

Trump says he likes testing people.

For example, he knew of a lawyer with a reputation for being a tough guy. Trump was looking for a tough lawyer.
Instead of asking him if he was tough, he tests him by saying: 

I don’t like lawyers. All they do is delay deals. They’re always looking to settle instead of fight.

When the lawyer “proved” his toughness, he told him what he needed and then hired him.

When talking to a young lawyer who looked even younger, he told him:

I’m not so sure that a lawyer as young as you are can handle a project like this.

Trump knew he was a good guy when he replied:

To tell you the truth Mr. Trump I’ve never had a client as young as you who could afford my bill.

A good way of passing the shit test.
And Trump respected that.

And Don’t Forget to Enjoy Life

Finally, Trump says:

Have fun. I don’t kid myself. Life is very fragile, and success doesn’t change that. If anything, success makes it more fragile. Anything can change without a warning. That’s why I don’t take things too seriously.

And more:

Money was never a good motivation for me, except as a way of keeping score.
The real excitement is in playing the game.
I don’t spend too much time worrying about what I should have done differently or what’s going to happen next. If you ask me exactly what the deals I’m about to describe all add up to in the end, I’m not sure I have a very good answer.
Except that I’ve had a very good time making them.

the art of the deal

The Art of The Deal Quotes

Plenty of quotes are already in this summary.
But here are a few more:

I hate law suits and depositions. But the fact is that if you’re right, you gotta take a stand. Or people will walk all over you.

On Parties:

Frankly, I’m not too big on parties. Because I can’t stand small talk. Unfortunately, they’re part of doing business, so I find myself going to more than I’d like.
And then try hard to leave early.

On politicians and money:

Eventually I realized politicians don’t care about what things cost. It’s not their money…

On the casino business:

I like the casino business. I like the scale, which is huge. I like the glam. But most of all, I like the cash flow.

On getting steady:

I dated a lot of different women by then. But I never got seriously involve with any of them. But Ivana wasn’t someone you’d date casually. Ten months later, we were married.

Talking about an architect working for him:

She is a classic. She has a mouth that won’t quit. Which is probably why she’s so good in sales. I like to tell her that she must a very tough woman to live with.

The unspoken rule among Gs:

He tells me he has a deal he’d like to discuss. He doesn’t say what it is, but with certain people… You don’t ask.

On easy returns:

Even by making this relatively minor things, I could earn at least a modern return on my investment. But then again, modest is not my favorite word.

On partnerships:

In every partnership, you’re only as strong as your weakest link.

On New York real estate:

(…) this is particularly true in New York real estate, where you are dealing with some of the sharpest, toughest, and most vicious people in the world. I happen to love to go up against these guys, and I love to beat them.

On incompetence:

Dishonesty is intolerable. But inaction and incompetence can be every bit as bad.

On cost-conscious realism:

You can dream great dreams. But they’ll never amount to much if you can’t turn them into reality at a reasonable cost.

On skyscrapers and money:

Skyscrapers are machines for making money. He meant it as a criticism. I saw it as an incentive.

On people’s strategy (and having a man open up to him):

There are times when you have to behave aggressively. But there are also times when the best strategy is to lay back.

On giving:

What I admire most are people who put themselves on the line.
I am not terrible interested on why people give. Because their motivation is rarely what it seems to be. And it’s almost never pure altruism. To me what matters is the doing.
And giving time is far more valuable than just giving money.

And finally.
What’s next?

Fortunately, I don’t know the answer. If I did, it would take the fun out of it.


The dollar always talk, in the end.

The Art of The Deal Criticism

Tony Schwartz, the co-author of The Art of the Deal, has been very vocal and critical since the publication.

He said that with this book he put “lipstick on a pig” and in another interview he said that if were to write the book again it would probably be titled “the sociopath”.

Both Schwartz and the Random House head Kaminsky, which is the publisher of the book, said that Trump wrote nothing of the book.

Real-Life Applications

Lots of real-life applications in The Art of the Deal ranging from money to people’s skills to philosophy.

  • You Only Need To Do Your Best

After the loss of his UCFL, Trump says:

I wasn’t happy. But I was relieved. My attitude is do your your best. And if it does’t work, move on to the next thing.

That’s a very positive, very healthy attitude.

  • Watch Out for Sharks

There are many people out there who will leverage anything to get your hard-earned money. Watch out specifically for people who come in with a great deal for you and push you to decide quickly.


  • Promotes a Genetic View On Instincts and Deal Making

Trump says that deal-making is an ability you are born with and it’s in the genes. It’s not about intelligence though, it’s about instincts.
This is not a con, but I’m not a big believer in these “inborn instincts”.

  • Is This Really Trump?

This book shows a level of introspection, self-awareness, and zen that you’d wonder if the Trump we see as the president is the same Trump who wrote this book.
To begin with, there is no huge self-promotion in The Art of the Deal. He says he learned not to act on impulses, and that chance and randomness helped him get what he wanted.
There are no signs of Trump being a sociopath in the book and no narcissism as some authors diagnosed Trump to be.

Did he change? Was he painting himself in a better light here?
Or is it true that Trump wrote little of this book?

In either case, I see lots of differences between the two. But that’s not a con for The Art of the Deal, which is a fantastic book.

  • Sometimes Unethical

In some passages, Trump shows the deal shark that he is.
For example:

Developers are suicidal, because banks are foreclosing them. It’s a great time for a smart buyer.

But most of all, it’s when he wanted to let homeless people inside a building to force the last owners to sell low, that it crosses the line.


  • Deeper Than It Seems

The psychology and the philosophy behind The Art of The Deal are outstanding.
Trump’s analysis of the neurosis that leads to success is spot on, as his philosophy on enjoying because life is uncertain.

Trump makes a lot of reflections here which are actually quite deep. For example, he discusses of people who will never find out about their talent because they simply never tried -for lack of good fortune or courage, he says-.

  • Great Childhood Stories

There is a lot here to understand what Trump is all about.

Sometimes you have to peep through the cracks though, as he’s likely trying to give a more positive impression -as everyone else would of course!-. For example, he says he was very aggressive in school, even giving a black eye to the music teacher :S

  • Great Sales and Marketing Training

Some of the marketing and sales techniques in The Art of the Deal are best in class.
I particularly loved the way Trump frames his Trump Tower as the “place to be”. His competitor shot himself in the foot by lowering the prices and leaving Trump Tower the upper section of the market.
Then Trump used “hard to get” techniques to sell space which made people want it even more.


Guys, you might not like Trump.
I find him entertaining, but not as a leader since people like Trump make for very poor presidents.

But I loved this book, and I truly didn’t expect to agree so much with Trump.
The Art of the Deal is loaded with wisdom not just on deal-making and power moves, but also on psychology and life philosophy.

Now Trump is a special kind of man.
Trump sees life as a  competition, that’s obvious. When he realized that people in Manhattan drank a lot he thought that, as a non-drinker, “he was going to have a big advantage”.
However, it presents little of the Trump we see today.

I will not weigh in on whether or not Trump actually wrote it and if it’s a realistic portrait of Trump back then.

However, as a website on social skills and “social power moves”, I found “The Art of the Deal” to be awesome.
This is The Prince of deal-making.

And actually, it runs much deeper than deal-making.
There is a lot of wisdom here when it comes to social skills, psychology, and even philosophy.

It’s also packed with great mindsets. And if you can put down the political blinders, it’s also jam-packed with powerful quotes and hilarious expressions that will make you smile -ie.: the Italian who looked like a WASP-.

In the end, think what you want of Mr. Trump, but “The Art of The Deal” is the crowning masterpiece of over-achieving deal-makers.

Check the:

or get the book on Amazon

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