Famous Risk Takers: Donald Trump

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Famous risk takers don’t come much bigger than Trump

With his billion dollar fortune, his monster hit TV show “The Apprentice”, his sprawling business empire and one of the most valuable apartments in New York City Donald Trump appears to be on top of the world.  But it wasn’t always this way.  At his lowest point Trump (sometimes known as “the Donald”) was facing personal bankruptcy with personal debts of $900M, while his business was declared bankrupt with debts of $3.5Bn.

One risk too many for Trump leads to bankruptcy

As soon as he finished university Trump went to work in his father’s real estate business.  After serving his apprenticeship he was given his first big project – the renovation of an 1,200 unit apartment complex.  Within 12 months he had completed the project and the newly renovated building was fully occupied.  Trump went on to build his real estate empire, with several assets bearing his name.

Down, but not out

By 1990 though, Trump was forced into bankruptcy when he could no longer meet interest payments on his loans.

Although Trump was forced to sell some assets and give up control of one of his buildings, he retained control of several casinos and other buildings.  This, however, wasn’t the end of his business career.  As Trump himself said: “Anyone who thinks my story is anywhere near over is sadly mistaken”.

Within four years he had almost cleared his personal debt, reduced the size of his business debt and merged several of his business interests into a publicly held company, which itself was forced to seek bankruptcy protection.

A new and more successful career

Trump shows that famous risk takers can win big as well as lose big.

Trump’s business empire currently includes:

  • Real estate;
  • Restaurants;
  • Travel;
  • A university;
  • Casinos;
  • Television.

Trump is the executive producer of the hit show “The Apprentice” as well as its star. He has also played himself in cameo roles in movies and comedy shows.

Trump puts his success down to being willing to take a risk.  He was once quoted as saying, “I like thinking big. I always have. If you’re going to be thinking anyway, you might as well think big.”


When you play for high stakes you stand to lose everything, but that doesn’t have to be the end of the game.  If you keep your wits about you, you can recover from even the biggest failure.  Here’s Trump’s own take on this:

“What separates the winners from the losers is how a person reacts to each new twist of fate.”