The Art of the Deal is an autobiography that covers Donald Trump’s life until 1987. It’s about Trump’s achievements in real estate development.

The book reveals Donald Trump’s mindset, which is the essential ingredient in his real estate success. My intention is not to review his real estate achievements, which are already well-known.

I studied the Art of the Deal to break down his most important beliefs, which later enabled him to be a successful television personality, and then, become the president of the USA.

Here are the top 21 mindset lessons from the Art of the Deal which you can apply to your own life today and start getting immediate results.

#1) It’s Not How Many Hours You Put In, It’s What You Get Done While You’re Working

This is an early life lesson Trump learned when he was working with his father. They hired a manager for a project and he turned up to be a great manager even though he worked only one hour a day:

Ultimately, we got a fabulous man whom I’ll call Irving. 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. I learned something from that: it’s not how many hours you put in, it’s what you get done while you’re working.

What Donald Trump learned early in life translates to every endeavor you take on in life. For example, go to the gym today and watch people work out. You’ll see that 99% of the people are not even trying. Hence, they look the same even after they spend years at the gym.

I only train 3 hours a week. But I give my all during these 3 hours. As a result, I managed to completely change my physique in a relatively short time period. The hour by itself is a poor measure of productivity. If you give it your all, you can achieve more in an hour than somebody else who puts in 10 more hours.

#2) To Be a Winner, Hang Around Winners

Donald Trump’s father had built real estate in Brooklyn and Queens. Young Donald had his eye on building real estate in Manhattan. He rented a dingy, dark apartment in Manhattan just to get a feel for the area. After he moved to his Manhattan apartment, he made an important decision which would, in his words, turn out to be a great move for him, socially and professionally.

One of the first things I did was join Le Club, which at the time was the hottest club in the city and perhaps the most exclusive— like Studio 54 at its height. It was located on East 54th Street, and its membership included some of the most successful men and the most beautiful women in the world.

“You are the product of your environment” is a cliché but it’s true. The attitudes of the people around you will slyly leak into your attitudes.

Hanging around winners taught young Donald lessons that he will use all throughout his career.

If hanging around winners is not immediately possible, anybody can immediately stop hanging around losers.

#3) The Simplest Approach is Often the Most Effective

Donald Trump always liked focusing on the meat of the matter. Being virtually a nobody who built nothing in Manhattan didn’t deter young Donald from making bold moves because he knew the power of simplicity:

I had never heard of Victor Palmieri, but I realized immediately that he was someone I wanted to know. I called his representatives and said, “Hello, my name is Donald Trump, and I’d like to buy the Sixtieth Street yards.” The simplest approach is often the most effective.

Simplicity is effective because it’s conducive to action. The action is what matters. The more you complicate things, the more you will procrastinate.

A simple diet is the most effective diet for weight loss. A simple training program is the most effective program to build muscle. Always remember to K.I.S.S (Keep it stupid, simple).

#4) Looks Matter a Lot, Make It Work for You

People like to think that they make rational decisions but they unconsciously make most of their decisions with emotion. This is a weakness and winners take advantage of people’s weaknesses.

Donald Trump knew this simple fact from a very early age on, so he constantly made use of it to sell his image and his products:

As I said earlier, I’ve always had a personal thing about cleanliness, but I also believe it’s a very good investment. For example, if you want to sell a car and you spend five dollars to wash and polish it and then apply a little extra elbow grease, suddenly you find you can charge an extra four hundred dollars— and get it. 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.


I hired Der and paid him to come up with sketches that we could use in our presentations to the city and to banks. I also told him to make it appear that we’d spent a huge sum on the drawings. A good-looking presentation goes a long way.

Good looks arouse good feelings. If you present good looks with yourself or your products, people will prefer you or your products.

#5) Be an Optimist Who Thinks Negatively

Most people confuse positive thinking with optimism. Optimism doesn’t automatically equal to positive thinking. Donald Trump is an optimist, who believes in the power of negative thinking.

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 worried about the future of New York City too, but I can’t say it kept me up nights, I’m basically an optimist, and frankly, I saw the city’s trouble as a great opportunity for me.

Successful people have more failures in life than successes. If you are aware that you will fail a lot, you will not bet your life’s savings on a single endeavor. Expect to fail but minimize your costs. When you succeed once, you will easily forget about the failures.

For example, go out and approach a beautiful girl today. If she rejects you, basically nothing will change in your life. If she doesn’t, you might have sex with a beautiful girl.

#6) If You Don’t Care About Your Own Money, Nobody Else Will

Humans are naturally selfish creatures. It’s simply not in our nature to care about someone else’s money, especially when that someone else is not a close friend or a relative.

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Yet, people tend to put their financial future in the hands of politicians or finance professionals. These people don’t genuinely care about your money. They only care about their money.

Donald Trump realized this early in his Manhattan real estate building career:

I discovered, for the first time but not the last, that politicians don’t care too much what things cost. It’s not their money.

Many rich people went bankrupt because they handed the control of their fortune to finance professionals. Some others went bankrupt because they made marriages without prenups. Lots of people pay more taxes than they should because they don’t inquire how to pay less tax money. Endless examples can be given.

Every penny you own is a soldier in your army to fight for your freedom. You always need to be financially literate to take care of your own financials.

#7) A 9 to 5 Job Is a Worst-Case Scenario

The most common advice you receive from childhood on is to get a college degree and then get a 9 to 5 job. While the powerful people make it seem like it’s in your best interests to jump through endless hoops to land a cubicle job, they do everything they can to avoid getting a 9 to 5 job.

Donald Trump noticed this with politicians:

If there’s one thing I’ve learned from dealing with politicians over the years, it’s that the only thing guaranteed to force them into action is the press— or, more specifically, fear of the press. You can apply all kinds of pressure, make all sorts of pleas and threats, contribute large sums of money to their campaigns, and generally it gets you nothing. But raise the possibility of bad press, even in an obscure publication, and most politicians will jump. Bad press translates into potential lost votes, and if a politician loses enough votes, he won’t get reelected. If that happens, he might have to go out and take a 9 to 5 job. That’s the last thing most politicians want to do.

A 9 to 5 job is a soul-crushing, thankless and fruitless labor to earn a living. Working a corporate job is only slightly better than being a slave (maybe not even that). Sometimes you’ve got to work a cubicle job to make ends meet but you should always look for ways of emancipation.

#8) You Can Build Anything Even When You Know Absolutely Nothing About What You Are Building

Humans are reluctant to take on new endeavors when they have inadequate knowledge and experience about the subject matter. As a result, they give up before they start.

Not Donald Trump. When he agreed to build a skating rink, he knew nothing about how to do it. But, that didn’t stop him:

Since I myself knew absolutely nothing about building rinks, I set out to find the best skating-rink builder I could. Logic suggested that the best place to look was Canada.


By the time I finished my first call, I’d made up my mind to use a brine system in rebuilding the Wollman Rink. The city, in fact, had finally come to the same conclusion. The only difference was that they first wasted six years and millions of dollars.

When you know nothing about how to build something, there’s always a chance to educate yourself. You can build your body, build a website, build a relationship, build a house etc… even when you don’t know how. Especially in the age of the internet, education is free and online. You can educate yourself on anything. If you don’t, you only have yourself to blame.

#9) Academic Achievements Don’t Mean Much

Most people are awed by prestigious schools but these schools mostly don’t live up to their hype. I graduated from one of the most prestigious colleges in the world (on scholarship) but I didn’t even bother to mention it on the about page of my website. I don’t have great things to say about most of my classmates either. To me, the whole prestigious school education thing was a major letdown.

Donald Trump experienced the same things as I did. He graduated from Wharton but was not impressed much with it:

I was a good enough student at the academy, although I can’t say I ever worked very hard. I was lucky that it came relatively easily to me, because I was never all that interested in schoolwork. I understood early on that the whole academic thing was only a preliminary to the main event— which was going to be whatever I did after I graduated from college.


Perhaps the most important thing I learned at Wharton was not to be overly impressed by academic credentials. It didn’t take me long to realize that there was nothing particularly awesome or exceptional about my classmates, and that I could compete with them just fine. The other important thing I got from Wharton was a Wharton degree. In my opinion, that degree doesn’t prove very much, but a lot of people I do business with take it very seriously, and it’s considered very prestigious. So all things considered, I’m glad I went to Wharton.

If you can do it on the government’s dime, do it. But, getting a student loan to attend an expensive but prestigious college is not worth it.

#10) Selling to the Poor is Not Worth the Pain You Go Through

Donald Trump’s father built real estate in Queens and Brooklyn. To Donald, doing business with poor people wasn’t worth it:

I’d just graduated from Wharton, and suddenly here I was in a scene that was violent at worst and unpleasant at best. For example, there were tenants who’d throw their garbage out the window, because it was easier than putting it in the incinerator. At one point, I instituted a program to teach people about using the incinerators. The vast majority of tenants were just fine, but the bad element required attention, and to me it just wasn’t worth it.


The second thing I didn’t find appealing was that the profit margins were so low. You had no choice but to pinch pennies, and there was no room for any luxuries. Design was beside the point because every building had to be pretty much the same: four walls, common brick façades, and straight up. You used red brick, not necessarily because you liked it but because it was a penny a brick cheaper than tan brick.

The majority of poor people may not have deserved their lot in life but some people deserve to be poor because of their bad decision making. These bad apples will drain your enthusiasm for your business. Moreover, you will be focusing on cutting the costs rather than using your imagination to improve your product. That will suck up your energy to the point of hating your business.

It’s much profitable and entertaining to sell to the rich.

#11) You Never Know Your Potential Without Taking Action

Humans have an innate tendency to preserve what they already have, rather than improve their lot in life. Improvement mandates action, so they prefer to do nothing as they fear losing what they have if they acted on their dreams. Donald Trump knew this from a young age:

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Somewhere out there are a few men with more innate talent at golf than Jack Nicklaus, or women with greater ability at tennis than Chris Evert or Martina Navratilova, but they will never lift a club or swing a racket and therefore will never find out how great they could have been. Instead, they’ll be content to sit and watch stars perform on television.

If you think like the majority, you will end up like the majority. The majority of the people suck. If you want to get ahead in life, you must take action. There are no ifs, ands or buts about it.

#12) Never Appear Desperate

Life is brutal. Desperate people get eaten alive, whether it’s fair or not. Donald Trump knew this early on, so even when he was a nobody at Manhattan with no achievements, he refused to appear desperate to make deals:

The worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood, and then you’re dead.

He even profited from other people’s desperation:

The funny thing is that the city’s desperate circumstances became my biggest weapon. With Palmieri, I could argue that I was the only developer around who would even consider buying a loser hotel in a decaying neighborhood in a dying city. With the banks, I could point to their moral obligation to finance new developments as a way to help get the city back on its feet. And with city officials, I could legitimately argue that in return for a huge tax abatement, I’d be able to create thousands of new construction and service jobs, help save a neighborhood, and ultimately share with the city any profits the hotel earned.

For example, you may be under a dry spell and haven’t had sex for months. If you show your desperation to women, you will not get sex. You may be desperate to get a job. But, if you appear desperate during a job interview, you will not get the job. That’s the way the world works. You can be desperate and that’s ok. But it’s never ok to show it.

#13) Don’t Push Your Worldview to Other People

Donald Trump had a brother called Freddy, who aspired to do other things in life than real estate business. Father Trump and Donald Trump disagreed with his aspirations and decided to push their views on him. He couldn’t withstand the pressure of his family and became an alcoholic, then, sadly died at a young age. Donald Trump learned the hard way not to push his worldview to his loved ones:

Eventually, it became clear to all of us that it wasn’t working, and Freddy went off to pursue what he loved most— flying airplanes. He moved to Florida, became a professional pilot, and flew for TWA. He also loved fishing and boating. Freddy was probably happiest during that period in his life, and yet I can remember saying to him, even though I was eight years younger, “Come on, Freddy, what are you doing? You’re wasting your time.” I regret now that I ever said that.

Perhaps I was just too young to realize that it was irrelevant what my father or I thought about what Freddy was doing. What mattered was that he enjoyed it. Along the way, I think Freddy became discouraged, and he started to drink, and that led to a downward spiral. At the age of forty-three, he died. It’s very sad, because he was a wonderful guy who never quite found himself. In many ways he had it all, but the pressures of our particular family were not for him. I only wish I had realized this sooner.

Life is not binary. Different people want different things out of life. There is no one particular way to live a life. You have no right to decide how other people should live their lives. This is why freedom is so important.

Nobody has the right to tell you how to live your life. That goes both ways. You don’t have the right to push your worldview to other people. It’s always tempting to change other people to your liking but it’s a better idea to focus on yourself and change yourself for the better. If you want to change the lives of your loved ones, lead by example, not by nagging.

#14) If You Want to Make More Money, Sell to Women

Ask any successful salesman and he will outright tell you that people buy on emotion, not logic. And guess who is more emotional: Women.

Donald Trump figured it out early in life just by observing her mother:

Looking back, I realize now that I got some of my sense of showmanship from my mother. She always had a flair for the dramatic and the grand. She was a very traditional housewife, but she also had a sense of the world beyond her. I still remember my mother, who is Scottish by birth, sitting in front of the television set to watch Queen Elizabeth’s coronation and not budging for an entire day. She was just enthralled by the pomp and circumstance, the whole idea of royalty and glamour.

I also remember my father that day, pacing around impatiently. “For Christ’s sake, Mary,” he’d say. “Enough is enough, turn it off. They’re all a bunch of con artists.” My mother didn’t even look up. They were total opposites in that sense. My mother loves splendor and magnificence, while my father, who is very down-to-earth, gets excited only by competence and efficiency.

All women are basically the same. It’s always harder to sell to men because we are interested in practicality which is harder to provide.

#15) The Government is Incompetent

Ordinary people have this weird fascination with the government but it’s actually very easy to see that the government sucks at almost everything it tries to accomplish. Donald Trump is no ordinary person and he figured this out, again, early in life:

A lot of times, when you are dealing with a government agency on a foreclosure, they just want to get out of it as quickly as possible. They aren’t equipped to manage it.

Never rely on the government as it’s bound to be incompetent. Always rely on yourself. Better, rely on yourself and profit from government’s incompetence as Donald Trump did.

#16) Aloofness is Attractive

When Donald Trump finished building the Trump Tower, he used aloofness to sell the apartments:

With so much demand, our marketing strategy was to play hard to get. It was a reverse sales technique. If you sit in an office with a contract in your hand, eager to make the first deal that comes along, it’s quite obvious to people that the apartments aren’t in demand. We were never in a rush to sign a contract. When people came in, we’d show them the model apartments, sit down and talk, and, if they were interested, explain that there was a waiting list for the most desirable apartments. The more unattainable the apartments seemed, the more people wanted them.

People want what they can’t have. It’s one of the core traits of human beings. It kind of sucks but since you can’t change it, you better acknowledge and profit from it.

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Aloofness also works with attracting women. Aloof men get laid a lot.

#17) The Worst of Times Often Create the Best Opportunities

Ordinary people love to lament on the bad economy but winners know better. Donald Trump built casinos in Atlantic City when no one else was willing to take risks because of the bad economic conditions the city was in:

Suddenly, a city that had been very hot for several years turned very cold, literally and figuratively. No one was talking about building any more new casinos. It seemed possible that the gaming business in Atlantic City was going to prove to be seasonal at best— enough to sustain only a few casinos. In my view, however, that translated into an opportunity.

Life is full of ups and downs. Ordinary people think they will prosper when the economy is good, and suffer when it’s bad. Successful people profit from both.

#18) You Can Trust Family in a Way You Can Never Trust Anyone Else

Donald Trump was already an established businessman when he got into casino business in Atlantic City. Since he lived in New York, he needed someone who can be hands-on every day. He had the power to hire the best people but he opted for his brother Robert because he needed somebody he fully trusted.

Atlantic City was the perfect opportunity. I was looking at a potential investment of $ 200 million, in a town 120 miles from New York City, where I couldn’t possibly be hands-on every day. What I needed was someone totally competent, totally honest, and totally loyal to oversee the project. There is nothing to compare with family if they happen to be competent, because you can trust family in a way you can never trust anyone else. I called Robert one evening in May 1980, we talked for several hours in my apartment, and by the next day, he’d agreed to take over day-to-day responsibility for Atlantic City. Among other things, that meant we’d both go for licensing.

The person you can trust the most in life is you. After you, your family comes. Not your friends, colleagues, boss or employees. It’s no surprise that people with strong family ties go further in life. Work hard to keep your relations with your family tight. You will need them and they will need you.

#19) Enthusiasm Alone Can Kick-Start Your Business

When Donald Trump moved to Manhattan, he never had built anything by himself. He wanted to build magnificent buildings in prime locations but since he had no track record, deals were harder to come by. He only had his enthusiasm going on for him, which was more than enough:

I think they liked my directness and my enthusiasm. I hadn’t built anything yet, but what I did have was the willingness to go after things that people in a better position than mine wouldn’t have considered seeking.

Enthusiasm is contagious. Even in the business world, people are still humans and they often make emotional decisions. If you show strong enthusiasm, established businessmen will take a chance on you.

#20) Much More Often Than You’d Think, Sheer Persistence is the Difference Between Success and Failure

Starting from the time he moved to Manhattan, Donald Trump had his eye on the location where he would eventually build the Trump Tower. Even when he had no track record, he had the temerity to start negotiations to buy the site. The owner of the site outright rejected his offer after their first meeting. But he kept on writing him letters until his deal started rolling:

I began writing letters to Franklin Jarman. First, I wrote to thank him for seeing me. A couple of months later, I wrote to ask if he might reconsider. When I got no answer and a few more months had gone by, I wrote again and said I’d love to drop by and see him again. More time passed, and I wrote another letter, suggesting a whole new way to make the deal. I was relentless, even in the face of the total lack of encouragement, because much more often than you’d think, sheer persistence is the difference between success and failure. In this case, Franklin Jarman never budged from his original position. But as it happened, the letters I wrote eventually did have an impact.

He ended up building the Trump Tower exactly where he imagined. Most people think they persisted enough and quit before they get what they want, or never persist at all. There are many things out of your control in life but your persistence is in your full control all the time. Failures and setbacks are ok but giving up is not.

#21) Have fun

No matter how competent you are, you can never predict the future. History is full of what the great Nassim Nicholas Taleb calls Black Swan events. Donald Trump is aware of this and he tries to 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 warning, and that’s why I try not to take any of what’s happened too seriously. Money was never a big motivation for me, except as a way to keep score. The real excitement is playing the game. I don’t spend a lot of 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.

Control the things you can control, let go of the things you can’t. You have no other option. Do the best you can do and have fun. Thinking about doom and gloom will not protect you and your loved ones.


The Art of the Deal is a great book that I found hard to put down. I listed 21 mindset lessons from the book but there are many more lessons inside. Everybody will have different lessons to learn from Donald Trump. I strongly recommend this book to every man, no matter his standing in life.

Culled from Lane Goodwin