Donald Trump Is The Greatest Political Entrepreneur Of All Time
Maxim previously endorsed Donald Trump for President of the United States—here’s why.
Donald Trump is aggressive, abrasive and audacious. That’s why we love him. He’s the hallmark of a truly transformative leader. Here are some of the ways Trump got to the top of the heap.
Doing It His Way
Ian Fleming once wrote about superspy James Bond, “Every man would like to live this way if he could.” The same can be said for Donald Trump. In so many ways, he embodies the lifestyle Maxim readers aspire to: money, power and performance.
Trump has that rare combination of self-confidence, shamelessness and ambition. Ever since he was a rising star in the Manhattan real estate market in the 1980s, he knew better than anyone how to grab the public’s attention and not let go. He retains that same hold on the public’s imagination today.
That’s not a fluke—that’s facts. Trump has turned his name into a symbol of luxury and power. He went from zero political experience to President of the United States, making him the most unlikely success story in generations. There’s a reason millions of people want to live vicariously through him. He’s bold enough to say what’s on his mind, rich enough to do whatever he wants and influential enough to get stuff done.
So, what’s the secret to Donald Trump’s success? Let us count the ways!
Dream Big
Trump doesn’t go for lightweight microaggression. The phrase “Go big or go home” is his mantra. “I like thinking big. I always have. To me, it’s very simple: If you’re going to be thinking anyway, you might as well think big,” he wrote in his book The Art of the Deal. His childhood friend Nikki Haskell agrees. “He always thought big. Everything—big buildings and changing the landscape and changing the skyline.”
Take Trump Tower, for example. While other kids dreamed about flying to the moon or playing drums for a rock band, Lil’ Don fantasized about building a massive skyscraper on Fifth Avenue right next to Tiffany & Co.’s flagship store. When he grew up, Trump began pursuing this dream by constantly contacting the owners of an 11-story building on the site. They blew him off numerous times, but Donald was persistent. He often gets what he wants by the sheer power of his will.
Eventually, the owners caved, and Trump built the ultimate man cave—a glittering 58-story skyscraper in midtown Manhattan with his name emblazoned on the front for the world to see. Adorned with pink marble and a cascading waterfall, the Trump Tower’s atrium soon became a tourist attraction. Trump often held court in the lobby, giving interviews and cultivating his larger-than-life image.
There was also its famed golden escalator. Decades later, when Trump first announced his candidacy for President in 2015, he descended the infamous escalator to reach the podium. This grand entrance into politics has become an iconic image that people still talk about today. However, Trump’s crowning achievement was his 30,000- square-foot penthouse at the top of the building. The triplex has marble floors, walls and columns with 24-karat gold accents sprinkled throughout. The ceilings are painted with scenes from Greek mythology.
Make Sure Nobody Forgets Your Name
What’s equally as impressive during this time is how Trump stood out from the pack, even in the booming 1980s. This was a time in the Big Apple when you couldn’t throw a rock without hitting a real estate tycoon. However, none of them got half the attention of Trump. The New York tabloids couldn’t get enough of the “The Donald,” as they called him. Reporters filled up pages and pages about his real estate dealings, his homes, wives, parties, yacht, cars and plane.
Why him and not the others? Trump was a social media genius before social media was invented, an influencer before people even called it that. He created an aura of exclusivity and glamour around himself. The Trump brand was not just a name on the side of buildings; it was a lifestyle. Realizing this, Trump began licensing the Trump brand to other companies, a move that would prove highly lucrative in the coming decades. This approach allowed him to expand his brand reach without taking on the full financial risk of each project.
Trump loves golf, so after he built Trump Tower, he bought another property where he could play whenever he wanted: Mar-a-Lago estate in Palm Beach, Florida. This 126-room, 62,500-squarefoot mansion on 17 acres was his winter retreat and later became a private club. With its 20,000-square-foot ballroom embellished with $7 million worth of gold leaf, antique Spanish tiles and 16thcentury Flemish tapestries, Mar-a-Lago is still where Trump wines and dines dignitaries from all over the world.
“Mar-a-Lago represented both the pinnacle of luxury and the achievement of a dream, and it became a trophy property in every sense of the word,” Trump has said. But Trump wasn’t done there. He had his sights set on the Plaza Hotel, a New York City landmark that he could see from the window of his penthouse. “How can I live without it?” he told a colleague. “It’s right in my backyard.”
He paid $407 million for it, the largest sum ever paid for a hotel. Later, he said in an interview. “To me, the Plaza was like a great painting. I have many assets like that, and the end result is that they are always much more valuable than what you paid for them.”
Rule The Land, Sea And Skies
Trump’s properties aren’t the only possessions worth drooling for. Trump’s diverse and impressive car collection is also a thing of beauty. His fleet has included a Rolls-Royce Silver Cloud, a MercedesBenz SLR McLaren and a Lamborghini Diablo VT Roadster, which he purchased as a 50th-birthday gift to himself.
The only drawback of owning these cars? Trump can’t drive them himself. That’s right. According to the Former Presidents Act of 1958, ex-presidents are not permitted to drive on public roads. But Trump can still be a passenger in one of his rides; he just needs Secret Service behind the wheel. Never one to be landlocked, Trump also expanded his posses sions to the sea. He purchased a 282-foot superyacht, which he renamed “Trump Princess.” This floating palace featured a disco, movie theater, helicopter pad and gold-plated sinks.
In a move straight out of The Art of the Deal, Trump acquired the Princess for $29 million from the Sultan of Brunei. At first, the purchase seemed out of character for Trump. He’s not a water person and has never owned a yacht before. But Trump saw the vessel’s value beyond just a personal plaything. It was the perfect networking tool. He invited Hollywood stars, political leaders, CEOs and diplomats on board as guests. The yacht was said to have 150 telephones (this was before the smartphone) and satellite communications so the VIPs could make deals from the high seas.
Not satisfied with having his name floating in the ocean, Trump would later buy a Boeing 757 worth $100 million. He called it Trump Force One, a precursor to the actual Air Force One he flew in during his presidency. The red, white and blue aircraft, with a giant Trump emblazoned across the cabin, has two Rolls-Royce RB211 turbofan engines and comfortably seats 43 people. It has a dining room, bathroom, shower, bedroom, guest room and galley. In Trump style, many of the fixtures are plated in 24-karat gold, including the seat belts.
The Trump Org’s aviation department also owns a fleet of Sikorsky S-76 helicopters. Each one is outfitted with fancy, comfortable interiors, refreshment centers and live map displays. As always, the Trump aviation logo adorns the exterior.
Throw Some Bangers
When it comes to hosting a party, Donald Trump has always believed you either turn it up to 11 or pull the plug. For his 42nd-birthday extravaganza at the Trump Castle Hotel & Casino in Atlantic City, the celebration began with a 15-foot spaceship launching from the stage, complete with smoke and lasers aimed at Trump and then-wife Ivana. Dancers performed a version of Michael Jackson’s “Bad” with the lyrics reworked to honor The Donald. He took it a notch up for his 50th birthday. According to a report in Australia’s “The Courier-Mail,” the bash for 400 guests included a “chocolate cake decorated with icing images of all of Trump’s buildings and a sugar figure of Don, dressed like Superman with a money sign on its chest.”
Make Hollywood Beg For It
The early 2000s saw Trump’s fame reach new heights with his foray into reality television. The Apprentice, which premiered in 2004 on NBC, skyrocketed Trump to a new level of fame and cemented his image as a tough, successful businessman in the minds of millions of viewers. The show gave Trump a weekly platform to showcase his business and leadership style. The catchphrase, “You’re fired!” became synonymous with Trump and revealed his knack for creating memorable, impactful messaging. Another Trump one-liner—“Make America Great Again”—would become his rallying cry for millions of frustrated voters.
“My brand became more famous as I became more famous, and more opportunities presented themselves,” Trump said.
Lead The Free World
As Trump began to consider a run for political office, he understood earlier than most the power of social media to make a beeline to his audience. He used Twitter to communicate directly with the public, bypassing traditional media channels.
“I love Twitter…it’s like owning your own newspaper…without the losses,” Trump tweeted.
This strategy allowed him to control his message and respond quickly to events, once again setting the tone for a new era of political communication. Even after being banned from Twitter, Trump launched his own social media platform, Truth Social, to connect with his audience. Like “You’re fired!” Trump’s political messaging in 2016 was simple memorable slogans, such as “Drain the Swamp” and “America First.” The red MAGA hat became an iconic symbol that transcended typical campaign gear to become a cultural touchstone.
In 2016, 62,984,828 American voters said, “You’re hired” at the ballot box. Overnight, Trump went from his penthouse on Fifth Avenue to the top of the world. He did this with virtually no help from the traditional political party system. In fact, most Republicans wrote him off. We’re not ready to write off Trump in 2024. Smart money says you should never bet against a wild card. “The show is Trump, and it is sold-out performances everywhere,” Trump has said. We expect plenty of people to show up to cast their ballot for Donald Trump on Election Day. You can bet on it.
Trump’s American Dream Playbook
So, what makes Donald Trump so memorable and impactful? There are many reasons, but a few stand out as being particularly Trump-esque.
Brand Consistency: Trump has always associated his name with luxury, success and power, whether it be in real estate, television or politics.
Media Savvy: Trump has demonstrated a keen understanding of media dynamics, often generating coverage through bold statements or actions.
Simple, Memorable Messaging: From “You’re fired!” to “Make America Great Again,” Trump has excelled at creating catchy phrases that stick in the public consciousness.
Personality-Driven Marketing: Trump has made himself the center of his brand, using his magnetic persona to attract a loyal following.
Direct Communication: Trump has prioritized talking straight to his audience, bypassing traditional media channels and political jargon.
Leveraging Luxury: Throughout his career, Trump has used his luxurious lifestyle as an aspirational representation of his success.
This article appears in our November/December 2024 issue. Click here to subscribe to Maxim magazine.
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