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Trump: The Art of the Deal – Lessons in Business, Bravado, and Big Wins

4/29/2025

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By William Ballard

Donald Trump’s The Art of the Deal (AFF) isn’t just a book—it’s part autobiography, part business manual, and part showmanship. Published in 1987, this bestseller provides readers with a behind-the-scenes look at how Trump became a real estate mogul and business icon, and who would later become the 45th and 47th President of the United States.

Love him or hate him, there’s no denying Trump’s knack for creating monumental deals, and this book captures his strategies, mindset, and unapologetic style.

But what makes this book stand out?



​It’s not just the lessons in negotiation—it’s the personality and humor infused in every chapter. With bold statements like “I play it very loose. I don’t carry a briefcase. I try not to schedule too many meetings. I leave my door open.” Trump’s approach is unconventional yet undeniably effective.
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Let’s explore the key takeaways from The Art of the Deal and how they can inspire entrepreneurs and business enthusiasts today. 
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The Daily Hustle: Trump’s Schedule of a Winner


​One of the most captivating sections of the book is the opening chapter, where Trump walks readers through a week in his life. From early morning phone calls to late-night deal-making sessions, Trump’s schedule is the epitome of hustle.
 
He writes, “I wake up at six and spend the first hour on the phone. I make 50 to 100 calls a day.” This insight into his daily routine showcases the importance of being proactive and relentless in pursuing opportunities. Entrepreneurs, take note: success doesn’t sleep.
 
But it’s not all grind and no play.

​Trump also emphasizes the importance of flexibility. He admits he doesn’t always stick to rigid plans, giving himself room to pivot and adapt. This balance between structure and spontaneity is a recurring theme throughout the book—and a valuable lesson for anyone trying to navigate the unpredictable world of business.  


The Power of Negotiation: Always Aim Big


​If there’s one thing Trump wants readers to master, it’s negotiation. For Trump, every deal is a game, and the goal is to win big. One of his signature techniques? Thinking big from the start.
 
He writes, “If you’re going to be thinking anyway, you might as well think big.” This mindset has driven his success in some of New York’s most ambitious real estate projects, from the Grand Hyatt Hotel to Trump Tower.
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Photo Credit: Trump.com
Trump also stresses the importance of knowing your worth and never backing down, even when the odds are against you. His confidence, coupled with meticulous preparation, often gives him the upper hand. For aspiring dealmakers, this section is pure gold.
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The Art of Selling Yourself


Trump understands that in business, your personal brand is just as important as your product or service. He writes, “I like to think of the press as a great free-ads department.” By leveraging the media, Trump has built an image synonymous with success, luxury, and power.
 
His advice to readers?

​Don’t be afraid to promote yourself. Share your achievements, tell your story, and make sure people know who you are. After all, the way you present yourself can make or break a deal.

  

Turning Problems into Opportunities


Trump’s career hasn’t been without its challenges, but his ability to turn setbacks into opportunities is what sets him apart. In The Art of the Deal (AFF), he shares how he took the crumbling Commodore Hotel and transformed it into the Grand Hyatt—a project that revitalized an entire area of Manhattan.
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Photo Credit: Trump.com
“The point is that you can’t be too greedy,” he writes. “You also have to be willing to take a loss if necessary, because then people will trust you.” This lesson in adaptability and integrity is especially relevant for entrepreneurs facing tough decisions.
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The Importance of Location (and Timing)


​If you're familiar with Real Estate deals, you've probably heard the old saying, "Location, Location, Location." And although location is important, and Trump emphasizes this importance... nevertheless, he also highlights the significance of timing. In other words, he describes times when having a great product trumps location. Knowing when to strike—and when to wait—is critical in any business venture.
 
As Trump puts it, “Timing is everything in life—and in business.” He shares anecdotes of deals that would have failed if he had been impatient or rushed the process. This timeless advice is a reminder that success often requires a mix of strategy, patience, and intuition.

  

Building Relationships: It’s Not Just About Money


Trump’s success isn’t just about dollars and cents—it’s also about relationships. He writes, “Deals are people. It’s relationships that matter.” This focus on building trust and rapport with partners, clients, and even competitors is a cornerstone of his business philosophy.
 
He shares stories of how he cultivated relationships with key players in politics, finance, and construction--relationships that proved invaluable when closing deals. For readers, this section underscores the importance of networking and collaboration in achieving long-term success.

  

Think Big, but Start Small


One of the most surprising takeaways from The Art of The Deal is Trump’s advice to start small. While he’s known for his grandiose projects, Trump began his career working on modest apartments in Brooklyn and Queens. These early experiences taught him the fundamentals of deal-making and property management.
 
He writes, “You don’t have to live a storybook life to be successful. Start with what you have and build from there.” This practical advice is a refreshing departure from the larger-than-life persona often associated with Trump.
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Managing Risks with Confidence


​In The Art of the Deal (AFF), Trump shares how he manages risks without succumbing to fear.

His secret?

Confidence and a willingness to take calculated risks.
 
He explains, “I try to learn from the past, but I plan for the future by focusing exclusively on the present.”

​For Trump, staying focused and refusing to dwell on failures is key to moving forward. This mindset is particularly relevant for entrepreneurs navigating uncertain markets or tough competition.
  

The Role of Vision and Passion


​Trump’s passion for real estate shines through in every chapter throughout The Art of the Deal. He describes his projects with a level of detail and enthusiasm that’s contagious. For him, business isn’t just about making money—it’s about creating something extraordinary.
 
He writes, “I don’t do it for the money. I’ve got enough, much more than I’ll ever need. I do it to do it.” This passion-driven approach is a reminder that true success comes when you love what you do.
  

The Legacy of The Art of The Deal


​More than three decades after its release, The Art of the Deal (AFF) continues to inspire entrepreneurs and business leaders. Whether you agree with Trump’s methods or not, there’s no denying the impact of his ideas on modern business practices.
 
The book’s legacy lies in its unapologetic celebration of ambition, creativity, and resilience. As Trump himself writes, “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.”
 
For readers looking to sharpen their negotiation skills, embrace bold thinking, or simply get a glimpse into the mind of a controversial business icon, The Art of the Deal is a must-read.
  

Final Thoughts on The Art of The Deal


​The Art of the Deal (AFF) isn’t just about real estate or wealth—it’s about mindset. Trump’s blend of confidence, creativity, and persistence offers valuable lessons for anyone looking to achieve their goals.
 
Whether you want to close your first deal, grow your business, or simply learn from one of the most talked-about figures in modern history, this book has something for everyone. As Trump says, “What separates the winners from the losers is how a person reacts to each new twist of fate.”
 
So, pick up a copy, dive in, and start thinking big. After all, the art of the deal starts with believing in yourself.
​
  

William Ballard is the founder and CEO of William Ballard & Associates, LLC. He is a serial entrepreneur and has built a successful career leading and growing organizations based, in large part, on his ability to ask great questions, speak with candor, and identify talented people with whom to collaborate.

​It’s from this foundation that William helps aspiring entrepreneurs, small business owners, and ministry leaders navigate organizational, industry, and societal changes to move their organizations closer towards their vision.
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