The Art of the Deal

by | 2019-05-22 5:22pm Asia/Tokyo

The Art of the Deal

by 2019-05-22 5:22pm Asia/Tokyo

Anybody learning about success wants to hear stories about the successful. We talk to successful friends and family and study their behavior, looking for their secrets. However, for those with high ambitions, friends and family often don’t model the level of success we are looking for. They may be successful in many ways, but not in the precise way that scratches our itch.

Billionaire President Donald J. Trump provides an undeniable example of life success in his book, The Art of the Deal. While Trump is a unique character with an exceptionally high tolerance for pressure—making his level of success difficult to replicate—his story has some lessons for those of us aspiring to do great things. Here are some lessons I learned from The Art of the Deal.

  1. It’s important to talk to lots of different people and get their opinions.
  2. To take on vicious people, you need to be vicious yourself.
  3. Attention is everything.
  4. Feelings don’t care about your facts.
  5. Play the games people want to play.
  6. Relationships don’t need to be deep to be meaningful.

It’s important to talk to lots of different people

One of the most important things that Trump does is talk to lots of people. He says that asking everyone for an opinion is a natural reflex for him. Learning the feeling of the public at large is an important part of his success. He once owned an apartment complex. After buying and renovating it, it became very successful.

One day, Trump was walking around the place and asked one of the areas residents how he was. The man whispered to Trump that he should sell the apartment. When Trump asked why, the man said that the neighborhood was declining. Lots of bad folks were hanging around. After looking around town and talking to more people, Trump sold to a sloppy company that didn’t do the same. The apartment began to lose residents shortly after the sale.

Trump has filled this book with the many accounts of his relationships with other people. Sometimes, he says things like, “nearly everyone I talked to opposed the deal” or “everyone I talked to agreed”. Trump talks to anybody and everybody. If you want to achieve higher levels of success, you have to talk to more people.


To take on vicious people, you need to be vicious yourself.

In business, Trump says that he tends not to trust people. That’s probably because people in business can be vicious. When it came to building in New York city, Trump says it took total focus, a kind of neurosis, to be successful. But, Trump says, he loved to go against them and beat them.

Trump often had to deal with businessmen and politicians that would lie or undermine him. He had several fights with the mayor of New York city, Ed Koch. Trump won every fight and loved it. He once had a falling out with Barron Hilton, who sold Trump a Hilton hotel which Trump called the Trump Castle. Trump wanted to resolve their problems over lunch in NYC. Barron said he would be delighted to have lunch the next Monday. Monday morning, Trump received a letter informing him that he was being sued by Barron. Trump filed a counter-claim exceeding Barron’s claim.

One time, Trump hired an apartment manager named Irving. Trump describes Irving as follows:

Irving was sixty-five years old and a real character. He was one of the greatest bullshit artists I’ve ever met, but in addition to being a very sharp talker and a very slick salesman, he was also an amazing manager. Irving was the kind of guy who worked perhaps an hour a day and accomplished more in that hour than most managers did in twelve hours.

Irving was the most capable person for the job, but there was one problem: upon investigation, they found out Irving had a long history of theft. How did Trump feel about that? He decided to take a risk.

With Irving I had a dilemma: he was far and away more capable than any honest manager I had found, and so long as he was in charge, no one under him would dare steal. That meant I only had to keep my eye on him. I used to kid Irving. I’d say, “We pay you $50,000 and all you can steal.” And he would act all upset. If I’d caught him in the act, I would have fired Irving on the spot, but I never did. Still, I figure he managed to steal at least another $50,000 a year. Even so, I was probably getting a bargain.

If you’re not vicious, it’s difficult to imagine making that kind of judgment call.


Attention is everything.

In a section called Get the Word Out, Trump says that it’s important to draw attention to whatever wonderful product you have. He prefers to do things that are a little controversial to gain the attention of the media. The media, by nature, wants something sensational. He writes that “people may not always think big themselves, but they can still get very excited by those who do.” In interviews, if he is asked to defend himself, he instead reframes the issue in a positive way, effectively turning free, negative press into positive press for him.

Previously, I’ve learned about the importance of attention from Mike Cernovich, Scott Adams, and Robert Cialdini’s work. Trump’s story provides ample evidence to support them.

More and more, I’ve come to realize that attention is the currency on which all human relationships are transacted. Attention is something that Trump has in unusually large quantities. His store of attention is so vast that it allows him to juggle complex business deals and personal media defense while maintaining his close relationships and managing his empire, all without going crazy or dropping dead in exhaustion. His success, I believe, is not only a function of his tolerance for conflict, but also of his store of attention he can give others, as well as his own voracious appetite for attention. He is an attention generating machine.

Attention looks like it will be the main topic of Cernovich’s next book, Audacious. I anticipate that Trump’s vast stores of attention, which he regularly empties and refills, may make a cameo appearance in Audacious.


Feelings don’t care about your facts.

There are many stories in Art of the Deal in which Trump talks about belief.

When the board of Holiday Inns was considering whether to enter into a partnership with me in Atlantic City, they were attracted to my site because they believed my construction was farther along than that of any other potential partner. In reality, I wasn’t that far along, but I did everything I could, short of going to work at the site myself, to assure them that my casino was practically finished. My leverage came from confirming an impression they were already predisposed to believe.

In other words, the facts didn’t matter. In fact, we almost take for granted that getting people to believe false things is both the norm in business dealings, and that it’s unethical. That may not be an entirely unfounded stereotype. After all, as I wrote before, Trump himself tends to distrust business people.

However, what is or is not a false thing is often not clear. Take the example above. After negotiating a contract with Holiday Inn’s, they scheduled a Board of Directors meeting at the build site for the casino Trump was going to build. Trump writes:

Rose [CEO of Holiday Inns] scheduled his annual board of directors meeting in Atlantic City so that the board would have an opportunity to see the proposed site and also to assess our progress in construction. It was the latter that worried me, since we had yet to do much work on the site. One week before the board meeting, I got an idea.


I called in my construction supervisor and told him that I wanted him to round up every bulldozer and dump truck he could possibly find, and put them to work on my site immediately. Over the next week, I said, I wanted him to transform my two acres of nearly vacant property into the most active construction site in the history of the world. What the bulldozers and dump trucks did wasn’t important, I said, so long as they did a lot of it. If they got some actual work accomplished, all the better, but if necessary, he should have the bulldozers dig up dirt from one side of the site and dump it on the other. They should keep doing that, I said, until I gave him other instructions. The supervisor looked a little bewildered. “Mr. Trump,” he said, “I have to tell you that I’ve been in business for a lot of years and this is the strangest request I’ve ever gotten. But I’ll do my best.”


One week later, I accompanied top Holiday Inns executives and the entire board of directors out to the Boardwalk. It looked as if we were in the midst of building the Grand Coulee Dam. There were so many pieces of machinery on this site that they could barely maneuver around each other. These distinguished corporate leaders looked on, some of them visibly awed. I’ll never forget one of them turning to me, shaking his head, and saying, “You know, it’s great when you’re a private guy, and you can just pull out all the stops.”


A few minutes later, another board member walked over to me. His question was very simple. “How come,” he said, “that guy over there is filling up that hole, which he just dug?” This was difficult for me to answer, but fortunately, this board member was more curious than he was skeptical. The board walked away from the site absolutely convinced that it was the perfect choice. Three weeks later, on June 30, 1982, we signed a partnership agreement.

Question: Was Trump acting unethically? After all, he was purposefully trying to make the board of directors believe he was further along in construction than he really was. The fact was that he was still two years away and still had nothing to show anybody. Was he lying?

Trump calls what he did “truthful hyperbole”. In the world of building, Trump was the rare person that could build on time and on budget. He had a long reputation for doing so. However, that meant that even if Mike Rose, CEO of Holiday Inns (who had come to Trump to make the partnership), trusted Trump’s abilities, Trump had to convince a group of reasonably grizzled veterans that he could pull off a miracle. The law of numbers says that at least one of them is going to show some skepticism. To prevent any delays from the board, Trump put on a show to put all doubt to rest. It was a show of truthful hyperbole.

The fact was that Trump really had nothing to show. Managing the feelings and emotions of the board, which were tuned for skepticism, bullshit detection, and disappointment, was the key to Trump’s success in that deal.

Was it unethical? Well, if he had failed, then it would have been reasonable to say that he was misleading the board to commit fraud. As it turns out, construction finished on time and under budget. Trump worked a miracle. He convinced the board, through truthful hyperbole, to relax and make a good deal.

Truthful hyperbole inhabits a gray zone of human behavior that few people have the stomach or desire to occupy. However, Trump practically has his home base set up in a gray zone. This is a high level technique that you can only deploy if you have a long history and are confident you can bring the same, consistent results.

Getting people to believe things you want them to believe has many uses. Let’s talk about Irving, the shady apartment manager. Trump writes,

I’ll give you an example of how Irving worked. You’ve got to understand that we are talking about a short, fat, bald-headed guy with thick glasses and hands like Jell-O, who’d never lifted anything in his life beside a pen, and who had no physical ability whatsoever. What he did have, however, was an incredible mouth.


As I mentioned, in the early days we had a good number of tenants who didn’t believe in paying rent. Sometimes, Irving would go out and collect himself. He’d ring the doorbell, and when someone came to the door, he’d go crazy. He’d get red in the face, use every filthy word he could think of, and make every threat in the book. It was an act, but it was very effective: usually they paid up right then and there.

One day, however, Irving had an unusual encounter with a woman and her daughter while on his rounds. Then…

About an hour later, Irving and I were sitting in his office when this huge guy, a monster, maybe 240 pounds, burst through the door. He was furious that Irving had cursed in front of his daughter, and he was ready to strangle him for coming on to his wife. The guy had murder in his eyes.


I expected Irving, if he had any sense, to run for his life. Instead, he started verbally attacking the man, flailing and screaming and chopping his hands in the air. “You get out of this office,” he said. “I’ll kill you. I’ll destroy you. These hands are lethal weapons, they’re registered with the police department.”


I’ll never forget how the guy looked at Irving and said, “You come outside, you fat crap, I want to burn grass with you.” I always loved that phrase: “burn grass.” And I thought to myself, Irving is in serious trouble. But Irving didn’t seem to think so. “I’d fight you any time you want,” he said, “but it’s unlawful for me to fight.”


All you had to do was look at Irving to know those hands were hardly registered weapons. But Irving was very much like a lion tamer. You’ve seen these guys, maybe 150 pounds, who walk blithely into a cage where there’s a magnificent 800-pound lion pacing around. If that animal sensed any weakness or any fear, he’d destroy the trainer in a second. But instead the trainer cracks his whip, walks with authority, and, amazingly, the lion listens. Which is exactly what Irving did with this huge guy, except his whip was his mouth.


The result was that the guy left the office. He was still in a rage, but he left. Irving probably saved his own life, just by showing no fear, and that left a very vivid impression on me. You can’t be scared. You do your thing, you hold your ground, you stand up tall, and whatever happens, happens.

Obviously, Irving wasn’t getting anyone to believe that he was dangerous. However, he effectively got the other man to believe that it was dangerous to attack Irving. Changing the 240-pound man’s anger into fear was a product of changing what he believed. At first, he believed he could intimidate Irving, and he believed that threatening Irving was worth his time. Irving showed no feelings of intimidation, and he reminded the man that it probably wasn’t worth it to start a fight.

Understanding and managing people’s beliefs and emotions is absolutely critical to success. You can’t brush them off as irrelevant to reality because beliefs and emotions are real to the person that has them. People often forget or ignore facts and are controlled by their feelings. People will even become even more defensive if they are presented with facts that prove them wrong. Their feelings don’t care about your facts. If you want peaceful, quick, amicable resolution to conflicts or to get good deals done fast, it’s often better to appeal to emotions rather than facts.


Play the games other people play.

A philosopher that I respect named Stefan Molyneux believes, as I do, that states are unethical entities that should be abolished. Taxation is money taken against the will of the taxed through the use of force. It is legalized theft. Money the state has is not its money, it is the money of those that the state has stolen from.

Furthermore, we are angered when we see how taxes are used to engage in war and imperialism abroad in our name. We believe that it’s unethical to engage in any form of aggression at any level. When our money is stolen from us and used to kill people, we are disgusted and infuriated. Our taxes are blood money.

Typically, us anarcho-capitalists prefer to boycott the democratic system because we view it as inherently corrupt and evil. It is the dictatorship of the 51% and participating in the system legitimizes and maintains the credibility of the state. We typically would stay on the sidelines during political elections.

Yet, typical of Molyneux, he did something that most other anarcho-capitalists didn’t do: he engaged in political activism during the 2016 US presidential elections. Our choices were between the evil we know, Hillary Clinton, versus the evil we didn’t know, Donald J. Trump. He saw the lies and sheer, overwhelming negativity and bias against Trump in the media. He realized that the election of Trump would be like a battering ram to the forces of power that supported the welfare/warfare state. If Trump were elected president, the media’s legitimacy as unbiased arbiters of truth would be damaged, if not outright torn down. If the people could see through the lies and Trump could defeat the political and media elites, it could be the beginning of a turnaround in human history. We might finally be able to turn the masses toward liberty and virtue, little by little.

At the very least, it was possible that we could avoid more wars started by blood-thirsty ghouls in Washington.

Molyneux’s activism was unpopular with anarcho-capitalist purists. However, many did cheer from the sidelines as Trump brought a fury of punches like a gattling gun to the media establishment which they hated almost as much as the political establishment. Yet, many still preferred to boycott the system, rather than try to reform it. They enjoyed the show, but it was still just a show to them. Nothing would change with a Trump presidency anyway. The establishment wouldn’t allow it.

Whether they were right or not, I don’t know. However, Molyneux’s activism was undoubtedly a deciding factor in Trump’s victory. Whether Trump did anything else good afterward, his mere defeat of Clinton was enough to make it worth it for him. Using the system to defeat the system worked.
I was apathetic to the elections until Molyneux began his activism. However, Trump’s election showed that it was possible to use the system to get the message of liberty out into the world and into the attention of the general public. How many millions of Trump loyalists were exposed to Molyneux’s peaceful parenting and philosophy material? How many people we nudged closer toward a freedom-mindset?

It was not the first time, however, that Trump had shown that success lay not in boycotting or attacking the system directly, but in playing the same game everybody else was playing. Trump speaks at length about how he and other New York City builders had to play politics to get zoning changed, tax wavers, low-incoming housing subsidies, grants, etc. If you want to be a successful builder in any major city, you have to play the game.

That game includes getting some tax advantage. Subsidies are tax money given typically to corporations to give them a competitive advantage. Anarcho-capitalists call those subsidies blood money. Trump calls them a part of doing business.

Yet, Trump’s argument and role modeling is undeniable. Not only was he successful thanks to tax waivers and low-income housing subsidies, but following the early successes in his career, he managed to give the government in New York a black eye several times. He showed not only how ineffective or how corrupt it was, but he showed how corrupting it is. He modeled the ideal behavior and outcomes one might see in a truly free economy like Molyneux and I envision it.

And he could not have done so if he hadn’t taken blood money.

And if he had not taken that blood money, we might stuck in another war thanks to Hillary. Instead, Trump transformed that blood money into peace talks with North Korea, canceled trade deals, and renegotiated deals with other countries. We have yet to know what other anarcho-capitalist-friendly actions Trump may take thanks to taking blood money early in his career.

Trump shows that there is value in playing the game even if you hate the game and the players. Flipping the table or going home does nothing but subvert any possibility of changing the course of history.


Relationships don’t need to be deep to be meaningful.

Trump’s life is a whirlwind of human interactions. At the time of writing, Trump would have 50-100 phone calls a day and talk to dozens of different people about complex deals or simply to thank them for their help. No doubt, as president, things have not slowed down. It is impossible to have a “deep” relationship with so many people. You also cannot predict whether a relationship will be long-lasting or fleeting.

However, you can still have meaningful relationships with people even if they aren’t deep or long-lasting. Trump hired a company called Cimco to rebuild a famous ice skating rink in NYC follow long government delays. The build took four months. The relationship Trump had with Cimco was short but sweet. He doesn’t mention any long talks between himself and the CEO. To my knowledge, Trump hasn’t built any other ice skating rinks. He may go back to Cimco in the future if he needs a lot of ice, but otherwise, their relationship ended four months after it started.

Yet, they did something important together. To this day, he can see the rink from his home in Trump Tower. It’s busy with activity. His short-term fling with Cimco brought real meaning and value to the customers who enjoy skating there.

In my life, I’ve often seen creating a “real” relationship with someone as requiring great effort and emotional investment. Yet, I’ve also mostly experienced only short-term relationships. I’ve often felt that it was pointless to talk to or try to get to know people since I would only know them for a short time. That’s a feeling that I’m trying to reform.

Trump shows a great example to follow. Every relationship has great potential, just like every person. From the customer that warned him about pending disaster at his apartment, to Dennis Rodman who went to President Trump to tell him to talk to Kim Jung Un, to Trump’s own lawyers and business partners, every relationship contains great potential. Despite Trump’s dim view of businessmen in general, he shows that there is great light, virtue, and strength hidden in humanity. It’s worth the effort to explore each human in the hopes of finding, or creating, a better humanity.



Now personally, I don’t like to judge other peoples’ work by what I believe it should look like. People like to criticize technology, TV shows, games, etc. by a standard that only exists in their heads. You’ve heard it many times before: They should have done this thing I like! Why doesn’t it have this totally awesome and useful cutting edge technology at bargain bin prices yet?! Why didn’t my favorite characters get married at the end?!

Rather, I like to judge a work on what it does and enjoy it for the value it brings. However, I do have interests and preferences that others might share. Instead of telling you what I think was bad about the book, I will tell you what the book did that I didn’t find of value to me. Maybe you might like it, though.
From the above references, you can probably see that The Art of the Deal is well written. It made boring business and lawyer talk interesting and exciting. I was happy to read to the end.

What you haven’t seen, however, is the many, many different names that are jammed pack in nearly every story. That is especially true in the first section of the book which details a week’s worth of activity in Trump’s life. I honestly skipped about 80% of that section. That probably says more about me than about the writing, but my mind simply became numb to all of the data thrown at me all at once. Even the later stories could be difficult to keep track of due to all the people and organizations that come up. Again, probably not something bad about the book, just an annoyance I had to deal with. Maybe I’m just not CEO material?

At the end of the book, Trump kind of summarizes the current condition or results of all the different deals and conflicts he was involved in at the time of writing. One thing I would have appreciated is a maybe a timeline showing the history of all of Trumps activities throughout the book. Making deals, building skyscrapers, and political battles take time. The book is organized around the deals and conflicts Trump was involved in, but much of Trump’s work was happening simultaneously. A timeline at the end could have given a nice bird’s eye view of everything and how everything progressed.

Also at the end of the book was a picture section. However, as someone who did not see the news or pictures of people and buildings in Trump’s life, I would have appreciated seeing the pictures during the telling of the stories themselves. Of course, if I had looked closely at the table of contents and known there was a picture section to refer to, I could have used it as a reference myself. But, my Kindle sent me straight to the first chapter, skipping the table of contents. Maybe I’m just a lazy bastard, but being asked to do a bunch of navigating just to keep the story straight sounds like a mistake on the author’s part.

Images of the characters involved in the story of Trump’s many dealings would have been nice, too. I can see why many of them, like Trump nemesis Ed Koch, wouldn’t have appreciated Trump making money with their images, so there was probably some practical, legal reason why they weren’t included. Still, it would have been nice.



In spite of my small complaints about the book, I felt it was well worth my time. Whether you’re interested in understanding the mind of Donald Trump, or are interested in learning lessons for success, The Art of the Deal should be on your reading list.