The Art of the Deal

I read this book, written by our current President when he was much younger back in 1987. I read it to try to gain insight into how he thinks and why he acts the way he does. I remember reading a news article about Dennis Rodman giving Kim Jong Un a copy of the book in 2017. If this book has been used internationally to try to understand the President, I thought I should read it too.

I think this book gives many insights into the psyche of the President.

His basic strategy of dealmaking is twofold:

  1. Aim very high
  2. Keep pushing and pushing and pushing

This strategy is exactly why he is President and why he acts the way he does, oftentimes. He aimed high and kept pushing through a large primary field and then kept pushing with large rallies around the country up until the day before the election. I think this is why he acts as he does with Congress, regarding unlawful immigration, and with foreign policy in Iran, North Korea, and even Europe.

As far back as the 1980s, Trump understood entertainment metrics from TV ratings to sporting teams attendance levels to news cycle sensationalism. I am positive this explains why he is so adept at controlling the media’s attention. He has a knack of tweeting a button-pushing tweet on a slow news day, or to fire up his base, or to get under the skin of his opponents. I doubt there has been a day since he started running for office when he was not in the news.

He wrote, “The only thing guaranteed to force [politicians] into action is the press -or more specifically the fear of the press.” The press is his weapon. He stated that applying pressure, making pleas or threats, and donating money all fall below the press in their effectiveness towards getting action out of politicians.

He shares stories of being truthful with a healthy dose of hyperbole to gain the attention of news reporters. From the time he hoped to build the world’s largest building to when he fixed New York City’s ice skating rink. We see this daily with his description of current events and overuse of adjectives such as biggest, worst ever, best, greatest, etc.

Trump does not fear judicial courts. Instead, he uses the courts and threats of legal suits as tools when needed. It seems like he thinks he has a handle on when he might win a lawsuit, and those are the ones he actually takes to court. Whether he might win or lose a lawsuit, does not hold him back from threatening a lawsuit, though. He uses the threat in those more grey situations as one to push the other side to back down.

He has a preference for complex deals. Deals where there are multiple moving pieces and the final deal remains contingent on all the other pieces falling into place. I think this is smart, as it avoids a small detail becoming an expensive or out of proportion liability. I see this in his work with the Middle East Peace Plan, North Korean denuclearization (and maybe Korea Reunification??), and renegotiation of NAFTA into USMCA.

Trump recommends dealing from strength. He says leverage (having something the other side wants, needs, or cannot do without) is the best strength you can have. With every policy he puts forth, there seems to be some obvious leverage on the table. Sometimes, it is threats (closing the Government down), sometimes it is trade-related (tariffs), sometimes it is whether he will campaign with or against the politician. “Deals work best when each side gets something it wants from the other.”  This went through my mind as I saw the latest budget deal pass Congress (I will leave my political thoughts out of this discussion).

In his book, Trump said, “Committees are what insecure people create in order to put off making hard decisions.” I think this exemplifies why his administration has had so much turnover. He wants to be the dealmaker, the decision-maker. I can’t imagine how difficult it would be to work in his White House. He does not seem to be a micromanager, but he does seem to want to know about everything and decide the important things. We see these effects when he contradicts even close Cabinet member associates. I think some people have been fired when they came across as slowing down a hard decision through committee behavior, though I have no proof.

When it comes to dealmaking, Trump says:

  1. Listen to your gut – go with instinct
  2. Stick with what you know (though it seems like he is open to learning new things to go after those..like the ice skating rink)
  3. Sometimes the best investments are the ones you don’t make (avoid bad deals – be willing to say no)

Much of the time, he avoids personal risk. If he can find a way to fund a development with other people’s money, and without a personal guarantee, he will take that deal. In this way, he can profit from the name, the management, the lease, construction, and more while if there is a financial issue, he can walk away.

Through the stories in this book, I recognize he values when people have skin in the game. He places value on action over words. He said, “What I admire most is when people put themselves directly on the line.” This is where the discussion of loyalty comes into play for him. Why he cares who joined his support and when they did so. Why he will not hire any Never Trump Republican. To him, he considers the doing as what matters. Giving time is far more valuable than just giving money.