Blog | Entrepreneurship

Rich Entrepreneur Poor Entrepreneur

Welcome to a new sub-brand of the Rich Dad Company, with its own forthcoming series of books, podcasts and videos.

meet your own rich dad - start your quiz now

Silly Questions

Journalist: “Why do you own a private jet?

Robert: “That’s a silly question. A better question might be: “Why don’t you own a private jet?”

Journalist: “Are you asking me; “Why don’t I own my own jet?”

Robert: “That is correct. Don’t you think that would be a better question to ask yourself…and for your readers?”

The journalist sat in silence, letting my question sink in.

Obnoxious Response

I realize my response was obnoxious. Yet I wanted to make a point. Allow me the opportunity, to explain my reasons for asking the journalist why he did not own his own jet.

In March of 2020, during the depth of the Covid-19 pandemic, this journalist had asked my executive assistant Sara, for an interview with me.

He explained he was a freelance journalist, writing an article for a magazine catering to entrepreneurs, start-ups, and “side-hustles.”

Sara set up a time, asking the journalist to forward a set of questions he wanted to ask me.

His list of questions was straight forward, questions I had been asked many, many times. His list of questions was:

  1. Can anyone become an entrepreneur?

  2. Why do 9 out 10 entrepreneurs fail in five years?

  3. Of the 1 out of 10 entrepreneurs that does survive the first five years, why most survivors work hard, stay small, and fail to grow?

  4. Why do only a few entrepreneurs get rich, and most do not?

  5. What would you say to someone, to encourage them to become an entrepreneur?

My time was tight. I was on my way to a meeting in Florida, so we agreed to meet at a private airpark where my jet, a Lear 60 was kept.

When the journalist met me at my plane, he completely forgot his list of questions. Our interview began with his question:

“Why do you own a private jet?”

And my obnoxious response was:

“Why don’t you own a private jet?”

The interview had begun.

I Am My Own Boss

The journalist let me know, he too was an entrepreneur.

“I am my own boss. I work for myself, and I only work when I want to work.”

He Hated Being Politically Corrected

He explained he once worked as an employee for a big city newspaper. He hated it. He hated being an employee. He hated being told what to do. He hated being told what stories he could cover, and what stories he could not. And he hated his boss, the newspaper’s editor.

The journalist especially hated being “politically corrected” by his editor.

The journalist’s articles were often “modified” to fit his editor’s and the paper’s “Woke,” racially unbalanced, gender bizarre, academically narrow, religiously restricted, politically liberal, and anti-Trump points of view.

The journalist said, “I was no longer reporting the new, I was slanting a newsworthy story into “woke propaganda.”

He said, “I quit my job because I want my First Amendment Rights back. I want to be a journalist able to practice my Freedom of Speech and the Freedom of the Press.”

I could only agree with him. I too want the same freedoms.

And we both agreed; since the advent of the Covid pandemic, our freedoms, especially our freedom of speech have been systemically embezzled.

We were both deeply disturbed when medical doctors were fired for questioning the sanity of Dr. Fauci. The journalist and I wondered; what was the truth about the origin of the Covid virus? Was Covid from “bats;” or “gain of function” research gone bad; or an intentional “Frankenstein” virus meant to cover up a mass financial disaster brewing in the “repo market?”

2008 Repo Market Crash

The journalist and I were both aware of a similar crash in the “Repo Market” just before the crash of Lehman Brothers, in 2008.

We were both aware that the 2008 crash in the Repo Market bankrupted many “Too Big to Fail Banks” and nearly brought down the world economy.

FYI: The “Repo Market,” is where big banks, financial institutions, and extremely wealthy families pledge their assets as security for loans…much like mom and pop’s pledge their homes, as security, for a home equity loan, or a bank secures the car you buy, as collateral for an auto loan.

Predicting the Crash on CNN

In 2008, I was on Wolf Blitzer’s program on CNN, predicting the coming crash of Lehman Brother’s days before Lehman went down. I felt confident predicting the crash of Lehman Brothers because I was aware of the crash in the Repo Market. I heard of the Repo Market crash because my favorite New York City bartender, “Bernie,” knew it was coming.

The night before going on CNN, I asked “Bernie the Bartender” what should I say to Wolf Blitzer. Bernie simply said, “Tell him Lehmann’s going down.”

As most of you know, the crash of Lehmann was the start of the GFC, the 2008 Great Financial Crisis.

When I asked Bernie the Bartender he knew about the Repo Market and Lehmann Brothers going down, Bernie simply said:

“You have no idea how much a bartender learns, serving drinks.”

I also found out Bernie, whose bar was in New York’s financial district, was a rich man, just on what he learned as a bartender. Bernie said:

You have no idea how rich and educated I have become listening to drunks sitting at a bar.”

As my rich dad often said to his son and me:

“You not need a college degree to become rich.”

Blaming Poor People

The journalist and I both were both disgusted at how poor, mom and pop, “subprime borrowers” were blamed for the 2008 crash, rather than the richest, biggest banks in the world that were going broke.

As you may know, GFC, the Great Financial Crisis of 2008 the richest banks in the world were bailed out, yet millions of moms and pops lost their jobs and their homes.

Dé-já Vu Again

On September 17, 2019, there was another crash in the “Repo Market.”

In September 2019, Covid-19 mysteriously appears reportedly from a lab in Wuhan, China, a lab the infamous Dr. Fauci, of the CDC, Center for Disease Control, has long been associated.

My question is:

“Are the Repo market crash and Covid-19 related?

The journalist was very familiar with the “Repo Market.” He had also been a financial writer and was aware of the Repo Market. He too knew the “Repo market” was where the biggest banks in the world pledge “financial assets” for collateral, just as you pledge your house for collateral for a home equity loan or your car for an auto loan.

And most of us know, if mom and pop fail to make the payments on their home equity loan or their car payment, the bank “repos” their home or their car.

Repo My Harley

One of the lowest days of life as an entrepreneur is the day my Harley Davidson motorcycle was “repo-ed.”

Burned in my brain, is the memory of a tow truck pulling up to my warehouse, where my “start-up” was.

My first major entrepreneurial business was the first company to manufacture nylon and Velcro surfer wallets. We were extremely successful, selling wallets all over the world, but success was causing us to go broke. We could not finance the demand for our products, so I stopped paying on my Harley Davidson.

One day, a friend saw me catching a bus to work. When he found out, I had no transportation, he offered me the use of one of his “collector cars.”

The car he said I could use was a 1968, white Mercedes Benz, 280 SL, with red top and red interior. It was and is a classic collector car.

One day, I was in downtown Honolulu, sitting in a no parking zone. I was so broke; I did not have a dime or a quarter to feed the parking meter. I was waiting for a car to pull out of a parking space with some time still left on the meter.

As I sat there in the no parking zone, a friend who once worked with me at Xerox, walked past. He knew I had left the job security of Xerox to start my first business. When he saw me sitting in my friend’s Mercedes, he smiled and said:

“Congratulations, your new business must be doing very well.”

Just then, a car began pulling out of it’s parking space, with time still on the meter, so I smiled and said:

“Thank you. I am very lucky.”

I then hustled off to take the parking space with time remaining on the parking meter. I wasn’t lying. At that moment, I was flat broke, yet at that moment I felt very lucky.

Words of Elon Musk

In 2022, I was listening to Elon Musk, answering questions about being an entrepreneur. One question he was asked


“What words of encouragement would you say to a person for them to become an entrepreneur?”

Elon’s reply:

“Failure is an option here. If things are not failing, you are not innovating enough.”

I agree. I have failed and hit bottom many times. My wife Kim and I hit incredible highs, after starting the Rich Dad Company in 1997. Oprah Winfrey had me on her show and “The Donald” before he became “President Trump” and I wrote two books on entrepreneurship.


As “The Donald,” Trump said:

The image of success is important, but even more important is the ability to focus on solutions instead of on problems. That way, you'll never be thinking like a loser, and you probably won't look like one either.

Failure Is the Door to Success:

As every successful entrepreneur knows, you fail far more than you succeed.

When asked how many times he fail, before inventing the electric light bulb, Thomas Edison replied:

“I did not fail. I successfully found out what did not work, 1014 times.”

That is why Elon Musk is correct when he says:

“If you need to be encouraged to become an entrepreneur, you’ll never become an entrepreneur.”

Can Anyone Be An Entrepreneur

To the frequently asked question:

“Can anyone become an entrepreneur?

My answer is:


I often tell the story of a high school student in my neighborhood who offered baby-sitting services, while she studied for her high school classes.

Although her parents were affluent, she earned and saved enough money, babysitting, to pay for her college education, with academic scholarships, and without onerous student loans, the worst type of loans possible.

The Problem

The problem is, while almost everyone can become an entrepreneur, very few will become rich entrepreneurs.

As Albert Einstein proclaimed:

“There are only two prime motivations for all human initiatives: Fear and Longing.”

Our current school system use fear of failing as a prime motivator, saying, if you fail you won’t get a good, secure, high paying job.

Book number two in the Rich Dad series of books, is The Cashflow Quadrant, pictured below.


‘E’ stands for employee

‘S’ stands for self-employed or small business

‘B’ stands for Big Business, 500+ employees

‘I’ stands for Inside investor: I say Inside Investor because most ‘E’ s and ‘S’ s invest as outsiders, investing primarily in paper assets manufactured by the Big Banks and Wall Street, assets such as stocks, bonds, mutual funds, and ETFs, which exploded in 2008.

Rich Entrepreneur Poor Entrepreneur

ANNOUNCING, the new sub brand of the Rich Dad Company, is Rich Entrepreneur Poor Entrepreneur. This new sub brand is for people, young or old, rich or poor, college educated or not, who want to learn how to be entrepreneurs in the ‘B’ and ‘I’ quadrants.

When I asked the journalist the obnoxious question:

Why don’t you own your own jet?

The journalist operated with the education and mindset prevalent in the ‘S’ quadrant. The biggest part of that mindset is the fear of failing.

As Einstein stated:

“There are only two prime motivations for all human initiatives: Fear and Longing.”

Most ‘E’ s and ‘S’ s fear failing and long for security.

On the ‘B’ and ‘I’ side:

Most ‘B’ s and ‘I’ s fear being trapped and long for freedom.

If the same journalist wants to own his own private jet, he will need to start thinking, studying, and acting like an entrepreneur in the ‘B’ and ‘I’ quadrants, which would bring up his fear of failing and increase his longing for security.

Q: Is it possible for ‘E’ s and ‘S’ s to achieve freedom?

A: Yes. Absolutely. All it takes is awareness and financial education. In fact, all of the staff and employees of the Rich Dad Company are motivated and encouraged to be on both sides of the Cashflow Quadrant.

Rich Dad Company does not provide a 401k or IRA plan filled with stocks, bonds, mutual funds, or ETFs. All staff and employees of the Rich Dad Company are encouraged to have their own “Side Hustle” and invest in rental real estate, real gold, silver and crypto.

All staff and employees have the best of both sides of the Cashflow Quadrant. They have security and are working for their freedom.

Which is why I am excited to announce, Rich Entrepreneur Poor Entrepreneur, a sub-brand of the Rich Dad Company, with its own series of books, podcasts and videos.

Original publish date: December 30, 2022

Recent Posts

The Virtue of High Expenses and Low Income
Personal Finance

The Virtue of High Expenses and Low Income

Ever wondered if money that goes out of your expense column could actually return into your income column?

Read the full post
Understanding the History of Money is The Key to Being Rich
Personal Finance

Understanding the History of Money is The Key to Being Rich

Leveraging information to create knowledge that makes you rich.

Read the full post
Building a Successful Business

Beyond the Idea: Building a Successful Business in Today's Competitive Market

Find your purpose, give it shape through the B-I Triangle, and learn as much as you can along the way. In this way, you can be both successful and happy.

Read the full post