Love him or Hate him, His Business Skills are Next Level.

Politics aside lets look at the Dons business venture’s and how he made his fortune.

Born into a Wealthy Family

I don’t want to take the credit away from Donald. There are plenty of people that are born into a wealthy family but don’t have the smarts to do anything with it.

Donalds initial start in business came from taking over his fathers real estate Company in 1971, who made a fortune building and selling property to soldiers in World War 2.

Donalds father Frederick had built condos, apartment buildings, FHA backed housing and other real estate.

Did you know Real estate has made more millionaires than any occupation? Crazy to think about. Especially if you got into it in the early days which Trump did.

First Investment’s a Killer!

He’s first investment would go on to be his most successful. A rundown hotel he partnered up with Hyatt to buy for $1M.

The neighbourhood was also in shambles and so he worked with the council to come up with a plan to rejuvenate the whole area and later went on to sell his share for $142M! Crazy!

They say your first million is hard to make and it becomes easier after that but making $142M is just ridiculous.

He did this again with 40 Wall Street.

Bought it for $1M but today it’s worth $500M!

The Apprentice

One of my all time favorite shows.

16 people chosen to take part in a reality TV series where the winner would help run one of Donalds companies.

Sounds pretty cool doesn’t it?

To go from a real estate mogul to having a popular reality show isn’t easy so you gotta give him credit to making it to 15 seasons!

You have to also give it credit for the entertainment value..

Throughout the Apprentice Donald made it a point to show off his lifestyle, he’s billion dollar status and generally the difference of living standards money could buy.

Although the TV Show was a completely different venture, Trump made it a point to sell himself as a ridiculously successful business man in a completely different social class to the rest.

A big way to market himself as the ‘go to’ guy for business education.

Every episode had him in the bossman seat where he’d, with two words, fire you in an instant.

The reward for winning challenges were 9 times out of 10, a look at his lifestyle.


A chance to go to some island in his private jet

A chance to see his mansion

A chance to see his up and coming business or new apartment complex

He still made the show to be entertaining as the major focus though. One thing I did enjoy was seeing the teams complete their tasks on a daily basis. They were given a budget and a day to get things completed. The hustle was real.

At the end of each TV show, they’d all meet at the boardroom where one person would get ‘fired’ and would have to leave the show.

I actually liked the Dons no BS attitude during this part of the show. The ability to just be straight up and tell he is contents what he liked what he hated and why they’d make a good or lousy employee.

Like the time he fired 4 people at once.

His later seasons would go on to include some pretty big name celebrities which he would also fire!

Using celebrities in a TV show does wonders in utilising their fanbase as a marketing tool. Kind of like Guest Blogging. Each celebrity would have their own mega fanbase Donald could use to increase viewership to his show and further market himself.

Smart guy.

But remember, at the end of the show he’d have to fire a celebrity! What do you think of when you see big Don fire famous celebrities? Doesn’t it make you wonder how much bigger than they, he is?

I’m not pointing all this out to say that he’s vain or arrogant, I’m pointing this out to show you how he positioned himself to eventually become the 45th president of USA.

Donald made it a point to market his lifestyle, he’s billionaire status and power throughout the show which ultimately served as a great platform to increase his popularity.


WWE was, and in many instances still is one of the biggest PPV entertainment ‘sports’ in the world.

Many people have used it in the past as a launchpad to get that demographic to follow them.

Like the time Maywhether came down to give the Big Show a taste of his boxing skills.

Donald Trump came down for a short series. Let’s look at what he did though.

He shaved Vince McMahons hair off! Who’s Vince? The CEO of WWE….

Ok, admittedly he got stunnered by Stone Cold Steve Austin but hey, he’s Stone Cold Steve Austin he does whatever the F$% he wants lol.

All These Successes, what About Failures?

An entrepreneur is almost never successful straight away, for the rest of his life.

Did you know Donald Trump was in bankruptcy 4 times? At one time he was down $3Billion!

How he handled the distribution of finances at that time, no one knows. Many people say he transferred his personal debt to the businesses and left many investors to take the hit.

But the bottom line is this guy took massive risks. Risks that could leave him on the streets but risks that could make him win huge.

Of the things he’s tried but you haven’t heard of,

  • Trump Steaks
  • Trump Wine
  • Trump the Board Game
  • Trump Magazine
  • Trump University

He would eventually go on to pull him self out with clever money management and realising success in other venture.

The Apprentice made him $1M PER episode and it went on to do around 185 episodes!

Not to Mention his Book, ‘the art of the deal’, that would go on to sell over 1 million copies and staying almost a whole year in the number 1 best seller spot!

Trump Now

Many big entrepreneurs eventually end up licensing out their products.

Trump licensed out his name. Many of his products aren’t even owned by him but use his name and pay him a massive licensing royalty/fee.

Continuous annual income and no financial risk, why not as long as these companies maintained a good rep, why not?

The Trump we see now was a serial entrepreneur not afraid to put his money on the line.

He gets attacked a lot for ‘taking a small loan of a million dollars’ but it’s not easy turning $1M into billions of dollars. Sure he had the connections, the initial money but plenty of business smarts had to come with it or he wouldn’t have made his money.

So How Did Donald Trump Get Rich? – Lessons Learned

Like I said, I’m leaving politics out of this one.

If you haven’t watched The Apprentice, you should, it’s a great show!

Also here’s some quick lessons you’ll learn watching him,

  • Risk is part of the game. Want to play it safe your whole life? Chances are slim you’ll make it anywhere in business
  • Never stop the hustle. To come back from billions in the whole is no easy feat.
  • Real estate is not always a bad or slow investment!
  • Collaborate with others to leverage and aim higher
  • Put yourself out there, your name, your ideas, etc
  • Experiment with other ventures

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Written by Mateen