The Art of the Deal

So, in the midst of all the excitement over the imminent Thousand Year Trumpenreich, I thought now would be a good time to read Donald Trump’s popular 1987 book The Art of the Deal. I don’t typically read books written by famous living people, partly because I prefer things that have passed the test of time, and partly because they’re often ghostwritten anyway. Now, Trump did have a coauthor, Tony Schwarz. In these situations, having a coauthor on a memoir often means that the coauthor did most of the actual work while the celebrity uses his name to sell copies. I’ll assume that this is still substantially Trump’s work just because he seems to take a hands-on approach to anything affecting his business, but it’s probably wise to keep this in mind. Also worth pointing out is that in any memoir the author is going to be selective about what he chooses to say about himself. Klemens von Metternich, for example, wasn’t self-revealing at all in his memoirs. Trump doesn’t give one a sense of hiding anything, and this is primarily a business book, not a confession, but again it’s best to be aware that any author will, consciously or sub-consciously, portray himself in the best light.

With that out of the way, overall The Art of the Deal is pretty good. It’s entertaining, reads quickly, has some interesting stories and points about both Trump himself and the business world in New York, and there’s also some decent advice. The book is divided into three parts. In the first, Trump goes through a week, outlining what he does each day, the phone calls he makes, who he meets, what public functions he goes to, and the like. It’s moderately interesting, but felt a little long; one gets a good feel for his daily routine after just a few days. This was published in 1987, but I suspect that his days haven’t changed all that much since then, despite the popularisation of computers, e-mail, and mobile phones. A former employer of mine, who owns a small business, always much preferred calling customers and vendors instead of e-mailing them, both because it was often more efficient and because it was more personable, and allowed him to try some extra salesmanship. Trump strikes me as the type of man who, even today, would rather call someone directly for the same reasons, instead of sending an e-mail and passively waiting for a response.

The second part is autobiographical, covering Trump’s early life and upbringing, as well as several pages about his father, Fred. It’s easy to see that Donald inherited a lot from his father; obviously, since Fred built mostly lower-income housing, he learned a lot about construction and real estate and got a start in the same general field from him. More than that, though, Fred clearly had a strong personality, and seems to have done business in a way very similar to his son. For example, Fred would inspect buildings he intended to buy very closely before signing anything, as Donald does, and once construction or renovations began would keep a close eye on contractors to make sure everything stayed on time and on budget, again, as does Donald.

Trump mentions that while Trump Tower was under construction, his father went to see the site for himself and pointed out to Donald several things he could’ve done to save money in materials. Donald points to this anecdote as a difference between the two of them, Fred thinking in terms of tight budgets, as opposed to Donald intentionally aiming for a much grander feeling to his building, but I sense that, once the higher-end materials were chosen, the two men would manage the project in much the same way.

The third part, the majority of the book, covers some of Trump’s major projects up to 1987, such as building Trump Tower, moving into the Atlantic City gaming industry, and renovating the Wollman ice skating rink in New York City. It’s essentially a highlight reel of Trump’s career, and whether you enjoy this book or not will largely come down to whether you enjoy reading these sorts of “war stories.” Personally, I did find the stories interesting, and Trump finds a good balance between giving us just enough information, along with his opinions on the issues and personalities involved, to know what exactly is at stake in each part of a negotiation, without getting bogged down in the minutiae that accompany deals involving millions of dollars.

Some of my favourite material is incidental to the main stories he tells. In one chapter, for example, he relates a visit to an acquaintance of his, an artist:

A few months back he invited me to come to his studio. We were standing around talking, when all of a sudden he said to me, “Do you want to see me earn twenty-five thousand dollars before lunch?” “Sure,” I said, having no idea what he meant. He picked up a large open bucket of paint and splashed some on a piece of canvas stretched on the floor. Then he picked up another bucket, containing a different color, and splashed some of that on the canvas. He did this four times, and it took him perhaps two minutes. When he was done, he turned to me and said, “Well, that’s it. I’ve just earned twenty-five thousand dollars. Let’s go to lunch.”

He was smiling, but he was also absolutely serious. His point was that plenty of collectors wouldn’t know the difference between his two-minute art and the paintings he really cares about. They were just interested in buying his name.

Those who’ve seen much of the modern art scene probably won’t be surprised. One eternally relevant passage is an observation about 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.

I’ve seen a few people refer to this book as something of a guide to business success or self-improvement. Trump certainly offers some advice here and there, but generally he simply offers, and exemplifies in most of his actions, a handful of strategies and virtues. Be self-confident, but always keep in mind how a project could go wrong and how you may be able to recover if it does; be patient, wait for the right opportunity to come up instead of jumping at every offer that comes your way, but once a good opportunity does present itself, pursue it aggressively; consider others’ advice, but ultimately it’s best to go with your instincts, and so on. As a taste, here he is talking about keys to good promotion:

The final key to the way I promote is bravado. 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. I call it truthful hyperbole. It’s an innocent form of exaggeration— and a very effective form of promotion.

One recurring theme that won’t surprise anyone who knows much of anything about Trump is his emphasis on not letting anyone walk all over him. When newspaper columnists criticise one of Trump’s projects, for example, he typically writes back. When he’s targeted with a lawsuit, even if it seems financially wiser to settle, he fights it. When a city commission or bureaucrat makes unreasonable demands, Trump does first try to find a compromise, but again, does look for an appeal if possible. Some of these controversies come across as petty, like writing to architectural critics, but Trump emphasises that the main point isn’t to win every little conflict, but to establish a reputation for strength; in the long-term, this means fewer people will try to pick fights with him, because they know he won’t simply back down. As he puts it in the first chapter, “I hate lawsuits and depositions, but the fact is that if you’re right, you’ve got to take a stand, or people will walk all over you.”

This is another one of those books that I could keep pulling interesting quotes from all day, so I’ll leave it there. The Art of the Deal isn’t a must-read, but is worth the time for anyone wanting to know a little more about the business world or, of course, Donald Trump himself.


  1. Gary West

    Richard, I very much like your commentary, finding it both insightful and enjoyable. I especially enjoyed the piece on Chesterton, who combined wit with intellect. Thanks — gary west


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