So You Wanna Be Rich? 13 Revealing Traits of the Most Successful Entrepreneurs

15 min read

So You Wanna Be Rich 13 Revealing Traits of the Most Successful Entrepreneurs

So, you wanna be rich and a successful entrepreneur? Great!

Whenever I coach entrepreneurs, they almost always ask one question:

“How do I become a rich and successful entrepreneur?”

As brash and bold as this question may sound, it gets to the point.

To become a rich and successful entrepreneur is a driving factor for most people.

And you know what, there’s nothing wrong with this.  In fact, this desire drives innovation, productivity, and the conveniences we enjoy.

So you wanna be rich?  Let’s look at 13 revealing traits of the most successful entrepreneurs.

A Quick Few Things Before We Start

In my past two posts, I talked about:

What’s easy to miss are the traits embedded in the 26 principles.

Success leaves clues, lots of them.  And you should take advantage of this.

I’m fortunate to cross paths with talented entrepreneurs, millionaires, and billionaires.  We’ve broken bread and shared our stories.

Unsurprisingly, the same pattern emerges when I’ve researched other insanely successful entrepreneurs.

This post is the genesis of the 13 revealing traits of the most successful entrepreneurs.

Here’s how you can get the most out of this post:

  • Read the entire post.
  • Identify the traits that best describe you and figure out how to do more of this.
  • Recognize the traits you don’t exhibit and find out if you can incorporate this into your routine.
  • Understanding each person is unique, focus on your strengths.
  • Realize there is no magic pill for success.

I’ve yet to meet a successful entrepreneur who has all 13 of the traits I discuss.

That’s good news for you.  If these successful entrepreneurs can do it, so can you.

All this said, here are the 13 traits that of the most successful entrepreneurs.

1.  Frustrated by the Status Quo

Insanely successful entrepreneurs are quick to challenge and change the status quo.

Changing the status quo was one of my primary motivators for starting Embanet.

Like most MBA programs, I found myself involved with a significant amount of teamwork.  In my particular case, my team decided to meet before, during, and after class to get the most of our program.

And by the way, did I mention this included weekends as well!?

My MBA team stumbled upon the perfect recipe for how to become the most miserable people in our program.

Tensions rose.  Tempers flared.  There was the talk of breaking up the group.

Our grades suffered, and I felt our health wasn’t far behind.

And this drama was only three weeks into a 2-year program.

The writing was on the wall, and it wasn’t good.

Insult to injury, I learned that my experience was common.  What doesn’t kill you makes you stronger, right?

For me, the situation was unacceptable.  I didn’t buy into the part of this is how it is.

I decided to make a change.  And I did.

The system I created gave my team and myself back our time, health, and happiness.  We enjoyed the program and earned straight As.

Imagine that!

An Empire Built From Challenging the Status Quo

Before we continue, I have a question for you.

Take a look at the two images below.

Virgin Money Lounge Successful Entrepreneurs

Virgin Money Lounge2 Successful Entrepreneurs

And now, a one-question quiz:

The images above are from:

(A)  The pages of the Robb Report Ultimate Homes Magazine

(B)  The lobby of a bank

If you selected (A), you’re in great company, but you’re wrong.

The two pictures above are from the lobby of Virgin Money.

Virgin Money is a bank started by Richard Branson for those of us across the pond.

No introductions are needed for Richard Branson.

An insanely successful entrepreneur, Branson built his empire by changing the status quo.

You can read more about Richard Branson in this Kissmetrics article.

Branson thrives on challenging the status quo, from banks to cell phones to music to space.

Branson gives the people what they want and in return, profits.

It’s a win-win.

2.  Decidedly Determined

Insanely successful entrepreneurs are decidedly determined.

Not convinced?

Check this out.  An aspiring author found herself in this situation:

  • Clinically depressed, divorced, and mother of a newborn baby
  • Lives on welfare
  • She has no support network when her mother passes away
  • Money is so tight our author rents out her apartment only to rent a smaller and cheaper place for herself and her baby
  • It took five painstaking years to finish her book
  • Rewrites her first chapter 15 times in response to rejection from publishers
  • Is told her book is too long, complicated, and of no interest to the target market
  • She never gives up and finally finds one publisher who agrees to buy the rights to her book for a scant $4,000
  • Five torturous years end up generating $800 per year
  • The author continues to push for her book

So let me ask you something.

Would you have lasted, or would you have quit shortly into this miserable nightmare?

Quitting was not an option for JK Rowling and her book Harry Potter.

Parents and children the world over can count their blessings on Rowling’s determination.

For more details about Rowling’s story, you can read my post.

Rowling took her dream to publish a children’s book and turned it into a billion-dollar empire.

The picture below is from an interesting article by MoneyNation.   Rowling’s financial success, chronicled by MoneyNation, is an interesting read.

JK Rowling Net Worth Successful Entrepreneur

Rowling’s determination made the difference.  As a result, Millions worldwide enjoy Harry Potter books, movies, and merchandise.

Nice done, JK Rowling!

Determination Built Embanet Into A 8 Figure Business

Launching Embanet and growing it was no accident.

Like Rowling, there were many obstacles.

I found that many of my biggest successes followed the most challenging times.

I had no money or resources.  Determination taught me that riches come ‘resource’fulness and not ‘resources.

I had many failures.  Determination taught me to play the long game, be patient, and wait for my day to arrive.

I had little to no progress in the early years.  Determination taught me how to take my game to the next level so I could compete and win.

The truth is, I wasn’t ready on many levels.  Determination prepared me for the success that was waiting for me to arrive.

Let determination be your guide and friend.

3.  Successful Entrepreneurs Are Creative Problem Solvers

Elon Musk So You Wanna Be Rich Successful Entrepreneur

Every successful entrepreneur I’ve met is a creative problem solver.

Elon Musk has a unique way of thinking that enables him to solve problems.

In case you’re wondering, this is the same Elon Musk who co-founded PayPal, launched Tesla and created SpaceX.

And Musk is warming up.

Examples of Musk’s brilliance include:

  • PayPal busts opened the doors for eCommerce by providing a safe and secure payment system.
  • SpaceX figured out how to build a rocket for NASA at 2% of the traditional costs. (Article here)
  • Tesla reduces the costs of battery packs from $600 per kilowatt hour to $80 per kilowatt-hour. (Video here)

How does Musk do this?

Musk attacks problems with out-of-the-box thinking using something called First Principles Thinking.

Musk explains First Principles of Thinking in this interview with Kevin Rose.

Want to become a First Principles Thinking master?  This Business Insider article by Drake Baer is a must-read.

Craving to learn more about the man himself?  This book is a must-read, Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future.

4.  Detailed About the Details

“If you don’t understand the details of your business you are going to fail.” – Jeff Bezos

Jeff Bezos launched in 1994 and forever changed online eCommerce.

According to this article, Amazon has:

  • 300 million customers
  • $136 Billion in revenue
  • 45,000 robots in its warehouses
  • 44% of web shoppers search for Amazon first

So, how did Bezos go from zero to hero?

Bezos is detailed about the details.

And the details don’t stop at Bezos, according to this article.  Amazon’s ideal employee is both introverted and detail-oriented.

The Everything Store book should do the trick for an in-depth look at both Bezos and Amazon.

What If I’m Not Detailed About the Details?

Jon the club!

When it comes to details, I’m not your guy.

So how did I grow Embanet if I’m not detailed about the details?

My personal philosophy is focusing on strengths and disregarding weaknesses.  After all, why waste valuable time on a weakness when I can make a strength even better?

My reputation at Embanet preceded me in this area.  When I was ready to hand off a project at Embanet, the team would dive for cover and hide.

And for a good reason.

My projects had serious implementation challenges due to a lack of details.

Now, when it came to vision, I rocked the house.  Implementing the vision was a different story.

Henry Ford said it best:

“Vision without execution is just hallucination.”

To compensate, I ensured that I surrounded myself with detail-oriented people.  The people I hired were better and smarter than me in the required areas.

5.  Motivated by Failure

So you think only losers fail?

Think again.

Successful entrepreneurs have mastered turning failure into a massive success.

Think Abraham Lincoln, Albert Einstein, The Beatles, and Oprah Winfrey, to name a few.

How does a successful entrepreneur get motivated by failure?

Start by reading this post.  You’ll learn ten questions and five strategies to transform failure into brilliant success.

And while you’re at it, take a look at the ‘Famous Failures’ picture below, compliments of

Famous Failures So You Wanna Be Rich Successful Entrepreneurs

Every successful entrepreneur I’ve met or researched has learned to welcome failure.

For successful entrepreneurs, failure is their teacher and friend.  Failure provides the unbiased truth.

Harsh as the truth may be, it’s an opportunity to improve when you fail.

10 Questions That Helped Me Transform Failure Into Massive Success

Embanet failed for the first thirty-six months.

Some of the bigger failures included:

  • No revenue in the first 18 months
  • An unreliable service from hardware failures
  • Inability to scale
  • Lack of consistency in the customer experience
  • Remaining the industry’s best-kept secret for many years
  • Not having the services required for customers to be successful
  • An inexperienced staff with poor training

And I’m still warming up.  The smaller failures could fill volumes.

As each failure happened, the frustration, pain, and embarrassment were intolerable.

In the beginning, it was me and my business partner who picked up the pieces.  Later, there was a small team that helped.

The following ten questions helped transform each failure into a success:

  1. How did this happen?
  2. Looking back, what could I change that would have led to a better outcome?
  3. Is there anything I can do right now to turn the situation around?
  4. Who can I turn to for an outsider’s perspective on my failure?
  5. What assumptions did I make, and were they right?
  6. When could I have changed to avoid failure?
  7. If I could do it all over again, what would I do and not do?
  8. What have I learned from this situation?
  9. Going forward, how will I prevent this failure from happening again?
  10. Who can help identify blind spots in my thinking, assumptions, and behavior? Select someone who knows me well.
Embanet’s Results From Massive Failures

Although it didn’t happen overnight, every failure made Embanet stronger. The results speak for themselves:

  • Embanet became the trusted advisor and golden child of the industry
  • Embanet had one of the highest net profits in the industry
  • One of the highest enrollment, retention, and profits for online programs
  • Tier 1 educational institutions
  • Some of the highest-quality students in the industry
  • A proven and effective system to graduate online students
  • High profits for educational institutions

Embanet went from zero to the hero because of failure.

I’ll leave you with a magnificent quote from Robert F. Kennedy:

“Only those who dare to fail greatly can ever achieve greatly.”

6.  Takes Risks

Successful entrepreneurs take the risk.

That said, let me dispel a common myth.  Successful entrepreneurs are more averse to risk than big risk-takers.

How can this be, you ask?

Great question.

Successful entrepreneurs are masters who take calculated risks.

An entrepreneur’s mind is a strange and wonderful thing.  Successful entrepreneurs think of everything that can go wrong and address those issues.

Case in point: Twitter’s founder, Jack Dorsey.

Issie Lapowsky has a wonderful article on Jack Dorsey and the launching of Square.

You can read this post on the story behind Square.

Before Square, accepting credit cards was expensive, confusing, and riddled with hidden fees.

Dorsey wanted to level the playing field with an easy and cheap service for small businesses.

Before starting, Dorsey came up with a manifesto titled ‘140 Reasons Why Square Will Fail’.  The title was a humorous one, playing off Twitter’s 140-character limit.

The manifesto was anything but light-hearted.  For every reason Square should fail, Dorsey and the Square team had an answer.

Square was not a shot in the dark.

Square was a calculated risk.

As of this post, the market cap of Square is $6.3 Billion.

Not bad for a calculated risk.

7.  Passionate About Trying New Things

Successful entrepreneurs are passionate about trying new things.

Founding Father Benjamin Franklin was a master of trying new things.

A few of the many inventions of Franklin include:

  • the lightning rod
  • bifocals
  • Philadelphia’s Fire Department
  • University of Pennsylvania
  • the first US Postmaster

Here are some great books about the man himself, Benjamin Franklin.

Like Benjamin Franklin, Steve Jobs was a master of trying new things.  Jobs’ brilliance was making existing things better.

The passion jobs had for trying new things brought us:

  • a user experience of simplicity and beauty
  • gorgeous, eye-popping computers
  • Apple TV
  • the iPod and iTunes
  • iPhone
  • iPad

Check out the article ’10 Things to Thank Steve Jobs For’ for Jobs’ contribution to society.

While you’re at it, you can read the history behind Apple’s products.

And why not learn the full story of Steve Jobs with these books?

And all from a passion for trying new things.

On a personal note, Embanet went from a 7 figure company to 8 figures by trying something new.

In fact, it was a single service that was responsible for the transformation.

What’s the one service, you ask?

We combined student marketing, enrollment services, hosting, course conversion, and technical support.

Was Embanet the first to develop the services?

Not a chance.  And on the marketing front, we were late to the game.

Our lethal weapon was our ability to package everything together.  Our service had little risk to our clients, was easy to use, and addressed a massive problem.

Like Dorsey with Square and Jobs with Apple, we took something that existed and made it better.

Rockstar results because we tried something new.

8.  Forgo Sleep and Pay When Excited

Lack of Sleep So You Wanna Be Rich Successful Entrepreneurs

Successful entrepreneurs forgo sleep and pay when on the hunt to make it big.

Nothing speaks to your commitment when you take a pass on sleep and pay when pursuing your vision.

If being an entrepreneur were easy, everyone would do it.

Behind the success of your favorite entrepreneur is a story of sacrifice.  A sacrifice that likely had little to no sleep and pay.

What I’m about to share is not to pat myself on the back or sing my praise.

I’m no different or special than countless entrepreneurs who do what it takes to get things done.

My sacrifices during the early years of Embanet include:

  • 4 hours of sleep most nights
  • No pay for the first three years
  • Traveling and away from my family for six months of the year
  • Friendships lost
  • Taking a pass on social events, vacations, and relaxing

Being an entrepreneur is not for the faint of heart.

I’ll be the first to share that this level of sacrifice is neither healthy nor sustainable.

Although this is required in the early days, your goal should be to get back your life as soon as possible.

9. Obsessively Curious and Creative

Successful entrepreneurs are obsessively curious and creative.

What would you say about pairing bacon with vanilla ice cream?

That pairing could only come from the obsessively curious Ben Cohen and Jerry Greenfield.

I’m talking about the legendary Ben & Jerry’s ice cream company.

Ben and Jerry cobbled up $4,000 each to launch Ben & Jerry’s.  The bank threw in another $4,000.

This $12,000 in start-up money turned into a $120 million dollar a year business.

Ben and Jerry channeled their curiosity and creativity for food and ice cream into an empire.

In April 2000, Unilever bought Ben & Jerry’s for $326 million.

This article shares how the company remains true to its roots only in Ben and Jerry’s style.

Unleash your curiosity and creativity.

Hold no shame in asking those questions you’re afraid to ask.

Your future business empire and its legion of raving fans will thank you for it.

10. Mastery of Money management

Successful entrepreneurs have a mastery of money management.

Despite popular opinion, your most valuable currency is time, not money.

Successful entrepreneurs are masters of managing their money.  As a result, successful entrepreneurs are buying themselves time to figure things out.

Case in point, Sergey Brin and Larry Page of Google fame.

Long before Brin and Page were billionaires, they mastered money management.

Steven Levy’s book, In The Plex: How Google Thinks, Works, and Shapes Our Lives, is a gold mind of examples.

Google has always had the need for speed.  One of the ways to achieve this is through many servers.

Not one or two servers. But hundreds of thousands of servers, if not millions.

Most companies follow the status quo, the antithesis of Rule 1, and buy expensive servers.  Companies like DELL and IBM are only too happy to fill the order.

Not Brin and Page.  The book In The Plex shares, “Larry and Sergey proposed that we design and build our own servers as cheaply as we can.”

Google’s first CIO, Douglas Merill, shared that the disk drives Google purchased were “poorer quality than you would put into your kid’s computer at home.”

Cheap parts mean high failure rates.  Server failures are a nightmare for an IT manager.  Most companies aim for a failure rate of 4% or lower.

Google’s hardware failure rate was almost 300% higher than industry norms at 10%.

So how does Google achieve speed and reliability with cheap hardware?

Brin and Page created systems that worked around the failures.


Mirror other successful entrepreneurs and master the art of money management.

7 Hacks To Achieve Money Mastery

At Embanet, our net profits were 53%.

You read that right.

The bottom line was 53%.

For every $1 generated, Embanet kept $0.53.

Below are the tactics I used to achieve such high profits:

  1. Use internal resources wherever possible. At Embanet, all our services were in-house.  From marketing to technical support to hosting to course conversion.  Embanet charged industry rates but had wholesale pricing and full control.
  2. Sign every contract.  Even as Embanet scaled, all purchases passed by my desk.
  3. Don’t provide company credit cards to staff.  I learned this the hard way. It’s amazing what people do when it’s not their money. I changed things around. The staff that incurred company expenses paid first and submitted bills for reimbursement. Our office manager was all too pleased to see how budgets were now followed and respected.
  4. Don’t provide company cell phones. Keep in mind this was before the days of unlimited calling like we have now.  But this still applies. The staff did not like carrying two phones. I didn’t like paying hardware and carrier charges. Instead, staff who required a cell phone received a monthly payment. Everybody won. The staff kept with the carrier of their choice with a phone they liked and had one phone. Embanet eliminated cell phone contracts, naughty carriers and policing our staff.
  5. Offer incentive programs. Suppose a staff member comes up with an idea to save money.  This staff member receives 30% of the savings for the next year.
  6. Negotiate. Negotiate some more. And for good measure, negotiate. Suppliers are only too happy to help. But you need to ask.
  7. Three quotes before any purchase. Enough said.
11. Ooze Passion

Successful entrepreneurs ooze passion.

And when it comes to passion, Steve Jobs nails it when he says:

“… people with passion change the world for the better.”

The 1997 Apple video, Think Different, says it all.

Jobs could write the book on passion for design and the user experience. Where everyone was comfortable with the status quo, Jobs hated it (See Trait 1).

Think lifeless and boring computers.  Visualize clunky and  ugly operating systems.

Remember those?

Or do you remember that beautiful eye candy otherwise known as the iMac?

iMac passion so you wanna be rich Successful Entrepreneurs

Jobs oozed passion. And it was Jobs’ passion that set Apple apart and positioned it into the company it is today.

What’s your passion?

Now don’t get me wrong. Passion isn’t always enough.

But Passion is THE starting point.

Your goal is to find the intersection of where your passion is in the middle of solving a massive problem.

And if that problem affects a lot of people who will pay you to take their pain away, you’re on to something.

Read my post that outlines exactly how you can find and solve massive problems.

No Passion No Success

I have a quick story for you.  I wish my story were fiction, but sadly, it isn’t.

After the sale of Embanet, I started another business in health care.

My business partner was the same one from Embanet.

On paper here’s what you have:

  • Lots of money in the bank
  • Two entrepreneurs who built a 8 figure company
  • A huge target audience
  • Government contracts
  • A team of experienced people from the healthcare industry
  • Both founders have a track record of huge success

This company had everything Embanet didn’t have. On paper, this company is set to hit a grand slam.

So what happened, you ask?

The company went out of business.

The company sold for pennies on the dollar.

Seven figures of investment lost.


Neither my business partner nor I had the passion.

Speaking for myself, I was greedy. I went into the business for the money.

That was one expensive lesson.

Successful entrepreneurs pour their passion into a massive problem, solve it, and prosper.

12. Soak Up Information Like A Sponge

Successful entrepreneurs soak up information like a sponge.

Let me share another story to illustrate.

Once upon a time, there was an entrepreneur who achieved massive success. This entrepreneur changed the world through technology.

This same entrepreneur was hanging out with a friend one day. As it happened, the friend lost a sale. It wasn’t anybody’s fault.

The entrepreneur couldn’t believe what he saw and vowed to solve the problem

In fact, the entrepreneur didn’t care that he knew nothing about this industry.

Instead, the entrepreneur was determined to change the status quo by thinking creatively. (Traits 1, 2 and 3).

The entrepreneur welcomed failure, was passionate about trying new things, and took risks. (Traits 5, 6, and 7).

Passion, curiosity, and lack of sleep and money led to the solution. (Traits 4, 8, 9 and 11).

You already know this entrepreneur from Trait 6.

And buyers and sellers the world over who use Square for credit card payments have Jack Dorsey to thank.

True to form, Dorsey, soaked up information like a sponge about financial services.

Although Dorsey was new to the industry, he figured it out. And in the process, Dorsey ripped the industry apart with Square.

Think about it. An outsider with zero experience and knowledge forever changed an industry.

How do you soak up information like a sponge?

Here are a few suggestions:

  • Read anything and everything relating to the industry
  • Interview anyone and everyone who is an authority in the industry
  • Speak to your target market
  • Huddle with creative people on how you can achieve your goal
  • Leave no stone unturned in your quest to learn

Knowledge is power when applied.

May you learn and prosper.

13. Decisive Under Pressure

Successful entrepreneurs are decisive under pressure.

John D. Rockefeller gives us a gem of a quote:

“Don’t be afraid to give up the good to go for the great.”

Every successful entrepreneur I’ve met or researched is decisive under pressure. Tough decisions were made. Risks were taken.

Not making a decision is making a decision. And the outcome is likely one that won’t have you smiling.

Every entrepreneur I’ve discussed in this post is decisive under pressure.

JK Rowling of Harry Potter fame, didn’t cave to the pressures of publishers to change her book.

Against all the odds, Elon Musk brought the Tesla electric car to market.

And the list goes on.

Not every decision you make works out.

In this article, Amazon founder Jeff Bezos is the first to admit,

“I’ve made billions of dollars of failures at”

Win, lose, or draw successful entrepreneurs are decisive under pressure.


So, you wanna be rich?

In this post, I’ve shared 13 revealing traits of the most successful entrepreneurs.

These 13 traits have helped to create rich and successful entrepreneurs.

As an entrepreneur, you’ll work hard.

But learn how to work smart. Wherever possible, mirror the 13 traits of successful entrepreneurs.

Work with the traits that play to your strengths.

For the traits that give you difficulty, don’t despair. Surround yourself with people who thrive in this area.

Remember, where there’s a will, there’s a way.

And speaking of a way, what’s the first action you’ll take for your business now that you know these 13 traits?

Here’s to you and your success!

Your Raving Fan,

Jeffrey Feldberg

Quote of the Day:
“All great achievements require time.” — Maya Angelou

Books For You To Read and Prosper

The Everything Store
Tesla, SpaceX, and the Quest for a Fantastic Future
Benjamin Franklin
Steve Jobs
In The Plex: How Google Thinks, Works, and Shapes Our Lives

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