What I Learned from “The Art Of The Deal”

With the election of Donald Trump (your president and mine!), I decided that it has become increasingly relevant for us all to read some of his books to get an idea of how the man “ticks”.

And so I picked up The Art of the Deal. Having done so, I can say that I’m glad: for while some of the book should be looked at skeptically (as should some of what Trump is saying in his presidency), as a whole, this book will provide some pretty solid advice on business and life in general, as well as, perhaps inadvertently, reveal some details about Mr. Trump himself .

This article does not seek to be a review of the book, so much as it is an article enumerating what advice one can glean from this best-seller, advice useful in both business and life in general:


1) Think Big. Most people are afraid to go for what they want, they’re afraid to succeed. “My father built low income housing, and at first I took up that mantle. When I was in Queens, I wanted Forest Hills. And I eventually realized Forest Hills wasn’t fifth avenue. So I looked towards Manhattan”. In other words, think incrementally big, don’t just go from 0-60: keep the end goal in sight, but realize you don’t go from zero to hero overnight. There is also an unspoken implication of “Aim big, because even if you fail, you’ll still bottom out higher than you would have if you didn’t try at all”.

2) Protect the downside and the upside will take care of itself. “People call me a gambler-I don’t gamble. I prefer to own the slot machine. The house always wins!” Or in other words, go in expecting the worst: And taking precautions against the worst. If you live with the worst, the good takes care of itself. You can’t hit a home run every time you go to bat-you should try to, but you should ensure that you at least hit the ball. He gives an example of his Atlantic City casinos: he made sure to get his gaming license and clear up all the paperwork before construction began.

3) Maximize options: Don’t get too attached to your current project. Most deals fall out so put a lot of balls in the air. In addition, make contingency plans for each deal. For example, if the license didn’t come for the AC casino, he’d still be able to sell the building and make profit.

4) Know the market (and act accordingly to it). He names various film makers, they each work in their own genre, but they each know how to hit that sub-demographic. And how do you know your market? He does his own surveys and draws his own conclusions.  “If I’m thinking of buying a property, I ask the man on the street about the area”. Ask lots of questions until you’ve formed an image of the area you’re buying in. And then you can begin to decide. Consultants charge a lot of money-be your own consultant.

5) Use leverage. The worst thing you can do in any deal is to seem eager, desperate to do it. And that goes for any interaction with another person, you always want to seem aloof. Leverage is a position of strength, you want to have something the other guy wants, so he seems eager and desperate. You must convince him the best thing he can do is sell to you.

6) Location can be enhanced. “I feel the most misunderstood aspect of real estate is the old adage ‘location, location, location’. Location is important, but even if your location isn’t that great, you can make it great with promotion and psychology. Even if you have a bad location, you make it good by making it fashionable.

7) Publicity is important, but don’t pay for it. “The press is always hungry for a good story…if you’re a little different, bold, outrageous, controversial, you will be written about”. And of course, all publicity is good publicity. When talking to the press, don’t lie, and don’t be on the defensive. “When a reporter asks me a tough question, I turn the tables  on him-when he talks about the negatives of my building, I tell him the positives of it. When they ask me why I only sell to the rich, I tell them that I benefit everybody-thousands of jobs, and I add to the tax base”.

8) “If you’re right, you gotta take a stand or else people will walk all over you”-this advice is what any good parent would tell their child, but what makes this advice interesting is that this pugnacious attitude has been associated with Trump well before his presidential run, and in many ways seems to paint his actions as a politician.

9) “Deliver the goods.” You can exaggerate and bluff all day, but there’s a time when you gotta show products of your labor. And now you know why I always use myself as a model in my fitness articles-showing that I practice what I preaching is my form of “delivering the goods”.

10) “Contain costs.” Spend what you have to for a good product, but not more than that. Every penny counts because pennies become dollars. If a contractor overcharges Trump for even a few thousand, he’ll confront him. “The day I don’t make a 25 cent phone call to save 5,000 is the day I retire”. Saving money isn’t really difficult, you shouldn’t have a problem with it.

11) Enjoy your work. Self explanatory. He likes doing this (Every aspect of being a tycoon, including the boring administrative stuff), and that’s why he succeeds at it, because he gets enjoyment from being a tycoon. I, myself, am not really one for business and money-grubbing, but what I do enjoy is teaching losers like I used to be how to be better men, which is why I happily provide you with at least two articles a week.

Those 11 tenets would be good enough, but there are even more lessons that the book can teach. Lessons that are not explicitly enumerated, but can be gathered with a little bit of critical reading:


1) “You can’t be innovative if you’re too structured”-I think the key here is “TOO structured”, you want to find a happy medium between being a total pedant and being so disorganized you can’t accomplish anything. Think of it like music: the greatest composers know when to utilize musical theory and when to break the rules, but when you ignore the rules completely, you get the atonal garbage they make nowadays.

2) “Learn from the past, plan for the future, focus on the present”. It seems fairly obvious, but many men struggle with this, either ignoring everything but the present or focusing too much on the past. Have a backup plan and “supplies” (whether literal or metaphorical) for the future, learn from your mistakes, and deal with your current problems.

3) “Thank everybody who helps you”-Trump makes it a point to personally thank everyone who does a solid for him, and so do I. Of course, Trump thanks people that donate to his charitable funds, or somebody who helps him in repayment for something Trump did for him, whereas I largely thank people who follow me on Twitter. Not only is this just simple politeness, it also keeps you in their mind, and makes them more amenable to helping you again in the future (this sort of “double edged kindness” is characteristic of Trump’s business dealing, and will be discussed more below)

4) “Don’t hold grudges”-In his business dealing, Trump is undoubtedly brought into conflict with many people. He also remarks how people who once opposed him are sometimes brought into the Trump Organization if they are beneficial to him-“I don’t hold it against them” (Chapter 1)

5) “There’s no harm in asking about something you’re interested in”-seems simple enough, but a lot of people struggle with this-just remember, if you want to get something, just ask to see if it’s available. This applies to a job, a real estate deal, a woman, anything. And if you get rejected, no harm has been done.

6) “Listen to your gut-don’t always ‘go on it’, but consider it at least.”

7) “Go with what you know”, related to the previous example, Trump almost bought an oil company, before getting a gut feeling about it: He had no experience with oil, so what business did he have buying an oil company? He went with his gut feeling not to buy it, and the company went out of business shortly afterwards. It is here that Donald also learned “Sometimes the best investment is to not invest at all.” “Going with what you know” also applies proactively-Trump discusses how his father taught him to be knowledgeable of all parts of the construction business, down to how much an individual brick cost. That way, nobody can pull the wool over your eyes, and you can demonstrate to your workers without needing to hire consultants.

8) “Take any opportunity to promote yourself”-citing an example of a miniseries with himself in a cameo role. He has no illusions about his (lack of) acting ability, but it’ll get his name and his tower out there. And sometimes ambiguity is the key, such as “neither confirming or denying” various celebrity clients buying Trump Tower suites.

9) “People buy the name brand”: Citing an example of a painter who makes a new painting in 20 minutes and then sells it for 30,000. The painting was  abstract crap, but the name sold it. This advice, of course, ties into the promotion discussed above.

10) “Good parenting goes far”-He freely admits that his father set him on the right path-not just giving him a partial inheritance, but also teaching him many of the aphorisms discussed above. And most importantly, making him work from a young age to teach him the value of money. Considering that Donald’s kids have largely avoided the pitfalls that other celebrity children have fallen into, I think it’s fair to say that for all his flaws, Donald Trump is a pretty good parent.

11) Project strength…without being confrontational. While Trump seems to feel this is largely instinctual, he had to discover this quickly while in military school. The drill instructor was a guy who would physically enforce his will whenever a student acted out of line, but Donald earned his respect through not being intimidated by him while simultaneously respecting his authority. Personally speaking, I have had good success by deliberately using bodylanguage to project that image.

12) Always read relevant things. Trump discusses how, in college, he was the only guy reading the Federal Housing Authority foreclosure notices-which he correctly interpreted as essentially a dirtsheet of cheap properties he could buy and profit upon. Whatever your field is, never stop learning about it-I certainly haven’t stopped reading men’s blogs since I’ve become a paid blogger, nor have I stopped reading tomes on music, martial arts, or anything else I discuss here.

13) Details matter. In other words, sometimes it pays to be “persnickety” and focus on the little details, because those little details accumulate and paint a picture of your work-Trump discusses how in his early properties, he could increase an apartment’s rent by a few hundred dollars just by fixing up the place with new paint or doors. “It’s so easy to improve something.” (Chapter 4) In other words, if something CAN feasibly be improved, there’s no reason NOT to.

14) “It doesn’t matter how long you work, it’s what you accomplish in that time”. Or as he puts it in the same paragraph, “Some guys can accomplish more in 1 hour than some other guys can do in 10” (Chapter 4)

15) “Talk yourself up any way you can”-Early in his career, Trump discusses trying to get into a club where all the wealthiest of New York Society congregated. While he doesn’t exactly explain what he said, he implies that he uses any positive quality to promote himself-his youth, his energy, his skills, etc. It’s fairly typical of a man who works in real estate.

16) “Work even when having fun”-At the aforementioned club, and all other social engagements afterwards, Trump uses such frivolity as a way to make informal contacts and publicize himself. To cite one far less successful example, I myself have utilized podcast appearances to increase my viewership while also making business contacts, and will continue to do so in the future.

17) “If you want anything done, go to the top”-In other words, don’t bother asking some mid-level employee about something, ask the boss. The employee only wants his salary and doesn’t care about your efforts that are greater in scope than his job.

18) “Sheer persistence is often the difference between success and failure”-this is nothing more than a “grittier” version of “If at first you don’t succeed…”. You should all know this already.

19) “Always be ready to show up”-Opportunity knocks at inopportune times, such as when Trump is called within the hour to a meeting that sold him the building that would ultimately become Trump Tower.

20) “If you don’t know what you’re doing, admit that, and get somebody who does”-This aphorism comes up when discussing his reconstruction of the Wollman Rink. Trump doesn’t know a thing about skating rinks, so he hires people who do. Simple.

21) “You are not judged on what you start, but what you finish”.

22) “Controlled neurosis”. Many successful people are kind of “off”-they’re obsessive, fanatical, but they channel it into their work.”This trait won’t make you happy, but it’s great if you have goals you want to achieve.” (Chapter 5)

And, perhaps most importantly, the best advice for any reader:

“This is a guide to finance, but like all things, there are no guarantees, use your own discretion about your personal circumstances and act accordingly”

Larsen Halleck is best known as the fitness and nutrition writer for Return of Kings, but also writes at his own website The Barbaric Gentleman, and also makes Youtube videos

You can follow him at his aforementioned website and Youtube channels, as well as on Twitter, and on Gab

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