Hard Truths About Trump: 5 Business Philosophies He Operates By

Business.com / Starting a Business / Last Modified: February 22, 2017

Does entrepreneur Donald Trump's unrivaled empire qualify him to run for POTUS? You decide after reading his five business philosophies.

Donald Trump represents everything wrong with business in modern America.

An unrepentant blowhard and a vicious opportunist who built his over-stated fortune by holding banks and business partners hostage, filing bankruptcy four times and host to countless other lawsuits for improprieties. He embodies arrogance and worships at the altar of greed, with no regard for ethics or the greater good.

Trump is an American icon, a fast-thinking ultra-sophisticated business savant and a throwback who defines the rugged individualism that made this country great.

He has single-handedly rescued distressed cities, bolstered local economies, creating tens of thousands of jobs in the process. Now, he’s efforting his opus: to lead our country to the same prosperity as President.

Love him or hate him, there is one thing we all agree on when it comes to The Donald, a real estate tycoon who is so successful that even his hair is famous. Multi-billionaire and 2016 GOP presidential hopeful, Donald Trump has built a brand that’s synonymous with wealth, luxury, and opulence like no one before or after him, brick by strategically placed brick.

But beyond Trump’s self-inflated ethos, past the power suits and “You’re fired!” sound bites, if we look behind the curtain on the real man and his track record in business, what will we find?

Here are five ways we might characterize Trump’s true business philosophies:

1. You Should Pull Yourself Up by Your Bootstraps, Like I didn’t.

While Trump loves to allude to how his fortune is self-made, the fact is that Donald was born into wealth. The son of real estate tycoon Fred Trump, Donald was handed the keys to the family business at only 28 years old and inherited anywhere between $40 and $200 million – not a bad start.

Related Article: Unlikely Role Models: Five Entrepreneurs You Shouldn’t Love but Do

2. When You Win, You Win. When You Lose, You Still Win.

Part of Trump’s shrewd brilliance is based on the way he tries to structure every deal to be a win or a draw for him personally, but never a loss. By relying on loans, banks, strategic partnerships, investors, and even government funding, Trump ensures that when a deal goes well, he profits enormously. But if a deal turns out to be a dud, Trump’s business partners are on the hook for the loss most of the time, not him.

3. All Debt Is Negotiable (Or “Bankrupt-able”).

Trump negotiates, renegotiates, and then re-renegotiates every debt and deal to gain an advantage. In fact, four of Trump’s businesses have declared Chapter 11 bankruptcy, including Trump’s Taj Mahal (1991), Trump Plaza Hotel (1992), Trump Hotels and Casino Resorts (2004), and Trump Entertainment Resorts (2009.). Some will argue that he was just taking advantage of our existing laws on the books and restructuring debt in good faith. Others think it is tantamount to legal theft that he keeps filing for insolvency to escape paying his debts, evade investors, and discard his obligations.  Either way, Trump’s record of bankruptcies cannot be separated from his legacy.

4. Be Your Own Walking, Talking Public Relations Campaign.

Not one to shy from shameless self-promotion, Trump unabashedly admits that the truth should never get in the way of closing a deal. He certainly has proven himself to be a master deal maker and genius negotiator, but time and time again, he has stretched the truth – or outright falsified claims – to inspire confidence and attract investors.

“Over the years I’ve participated in many battles and have really almost come out very, very victorious every single time,” said Trump at the 2011 Conservative Political Action Conference. Apparently, Trump doesn’t count his multiple business failings and bankruptcies as blemishes on his record.

By the way, Trump recently claimed to be worth $10 billion, but Forbes estimates his worth at closer to $4 billion, dropping as low as $500 million during the recession.

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5. You’re Selling Perception, Not Reality.

Trump is a maestro at building his brand. These days, the Trump name on any project signifies luxury, extravagance, and opulence. He puts his name on anything that is sturdy enough to hold it and makes sure his hotels, casinos, and buildings have impressive facades with grandiose fountains, royal atrium staircases, and shiny-faced exteriors. That’s because long ago, Trump understood two important facets of human nature:

  • People want to be associated with a winner
  • People buy the idea of something, not just the actual thing


"I play to people's fantasies," he writes. "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."

Of course, that could just be seen as great salesmanship. However, if you were a bank, investor, or someone buying into one of his signature projects with your hard-earned cash, you might prefer financial transparency and good dealings instead of Trump’s snake-oil hyperbole.

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