Trump: The Art of the Deal
Intro
I’ve had The Art of the Deal on my reading list for over a year now, but I never quite felt in the mood for it. Honestly, after watching Donald Trump on The Apprentice—firing people with a stone face and brushing off celebrities like it was just another Tuesday—and later seeing him on the debate stage, confronting politicians head-on without flinching, I felt like I already had a decent grasp of who he was.
But with recent news around tariffs and trade—especially involving Asia—I realized I needed to dig deeper. I don’t just want the headlines anymore; I want to understand the foundations: economics, foreign policy, and how deals are made (and spun). So I finally picked up the book. Here are some takeaways, surprises, and thoughts on what it reveals—not just about Trump, but about the business and political mindset behind the deal.
Eleven Key Principles
1. Think Big
Trump emphasizes the power of ambition. Thinking small limits potential, so he encourages setting bold, even outrageous goals. His belief is that aiming high brings out the best in people and attracts attention and respect.
2. Protect the Downside and the Upside Will Take Care of Itself
This is about risk management. Before making any move, Trump considers the worst-case scenario. If he can live with the downside, he proceeds. It’s a pragmatic principle focused on protecting yourself from ruin.
3. Maximize Your Options
Flexibility is key. Trump avoids boxing himself into a corner by keeping multiple options on the table. This gives him the ability to pivot, negotiate, or walk away when needed.
4. Know Your Market
Understanding your audience—whether it's customers, investors, or political opponents—is crucial. Trump stresses doing homework, paying attention to trends, and reading people accurately to shape your strategy.
5. Use Your Leverage
Leverage is power. Trump believes every negotiation involves some kind of leverage, even if it’s not obvious. The trick is to identify it and use it without revealing your hand too early.
6. Enhance Your Location
In real estate and beyond, value often depends on perception. Trump talks about “making your location better,” whether by renovation, branding, or simply creating buzz to elevate its worth.
7. Get the Word Out
Publicity is a tool, and Trump is unapologetic about using it. He sees media attention as a way to build value, influence perception, and create momentum, often ahead of any actual deal being finalized.
8. Fight Back
If attacked—legally, publicly, or competitively—Trump advises not backing down. His approach is to confront criticism head-on, and if necessary, fight harder and louder than the opposition.
9. Deliver the Goods
Once a deal is made, results matter. Trump believes in following through and exceeding expectations when possible. It builds credibility and makes future deals easier.
10. Contain the Costs
Trump watches expenses closely, even on massive projects. He advocates negotiating hard, keeping overhead low, and avoiding unnecessary spending to protect profits.
11. Have Fun
Finally, Trump claims that loving what you do fuels persistence and creativity. For him, making deals is exciting—it’s not just about money, but about the game itself.
Walter Hoving
Of all the deals Trump describes in The Art of the Deal, the one that stood out to me most was his negotiation with Walter Hoving. I wanted to highlight this deal because it revealed how Trump was able to identify and use leverage while still creating a win-win outcome. Though this wasn’t the only deal in which he did so, what made this deal especially memorable wasn’t the strategy alone, but the character of Walter Hoving himself.
His integrity stood out—not just to me as a reader, but clearly to Trump as well. Even when new information came to light that could have made the deal more profitable for him, Hoving kept his word. And after selling Tiffany & Co., he went out of his way to ensure the new owners honored the agreement. In a book full of sharp negotiations and shifting power dynamics, this was a rare moment where trust and principle held the deal together.
Context
Location: Trump Tower development on Fifth Avenue, Manhattan.
Issue: Trump wanted air rights over the Tiffany building next to his property, which would give him more flexibility in construction or future expansion.
Challenge: Walter Hoving, known to be proud and a man of taste, wasn’t easy to negotiate with.
Reputation and Trust Go a Long Way
Trump understood that Hoving cared deeply about Tiffany’s reputation. By reassuring him that Trump would treat the neighboring property with class, he built trust.
“He believed me, and that was the key to the deal.”
Trump didn’t "defeat" Hoving—he made him feel respected and involved. That’s why the deal happened smoothly.
After Trump and Hoving had a verbal understanding regarding the air rights over Tiffany’s, a new development occurred that could’ve changed Hoving’s mind.
“Just before we finalized the deal, a zoning change was proposed that would have made the air rights worth considerably more.”
This is critical. Hoving had every reason—financial and legal—to back out or renegotiate. But he didn’t. Trump respected that deeply.
“Hoving could easily have said, ‘Sorry, the situation’s changed,’ but he didn’t.”
Lesson: In some deals, especially with high-profile or legacy-driven people, trust and image can outweigh dollars.
Think Long-Term and Strategically
Even though Trump didn’t have a clear plan for the air rights immediately, he still pursued the deal because he saw potential future value.
“I had no immediate need for the air rights... but it seemed to me that someday they might be useful.”
Lesson: Acquire leverage even if it doesn't pay off right away. Strategic foresight can pay off later.
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