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7 Business Coaching Lessons From Mark Cuban with Karl Bryan

by | In the Magazine, Karl Bryan

“I’ve learned that it doesn’t matter how many times you fail. You only have to be right once.” 

His net worth is estimated at $3.3 billion.

At this stage of his life and the amount of success he’s had… you could understand if he decided to put his feet up and relax. And yet, he’s gone entirely in the opposite direction.

Mark Cuban has invested in 37 different businesses on the hit show Shark Tank. Many of them were runaway successes but also included a few flops.

In his spare time, he owns and runs the Dallas Mavericks, Landmark Theaters, Magnolia Pictures and HDTV cable network AXS TV.

For this superstar entrepreneur, it all got started with a pair of shoes. But not a pair of Air Jordan’s nor anything to do with his beloved Dallas Mavericks.

They were a really cool pair that 12-year-old Mark Cuban told his Dad he needed. His Dad’s reply was a definitive one.

“You’ve already got a perfectly fine pair of shoes Mark. When you have a job and earn your own money, you can spend it however you want,” his dad said.

That was a lesson he took to heart. If you want something, go work for it and earn the money. And work young Mark most certainly did.

With the help of a family friend, Mark began selling garbage bags door to door. This was the beginning of his love affair with sales and business.

“I’ll never forget. They were those thin blue things. My friend charged me $3, and I sold the garbage bags for $6.  Everybody needs garbage bags, so I learned to fill a need and I learned to problem solve.

Since his initial venture, the numbers have increased somewhat.

In 1990, at the age of 32, he sold MicroSolutions to a subsidiary of H&R Block for $6 million.

His next exit was the famous transaction to Yahoo for a cool $5.7 billion for the now defunct

Cuban was 41 years old.

In 2000, with some loose pocket change from his most recent exit, he purchased the Dallas Mavericks for $285 million.

This was considered a reasonably risky purchase at the time, but the franchise is now valued at $1.4 billion.

Cuban says the best advice he ever got was from his Dad,

“Today is the youngest you will ever be. Live like it.” His point was that as we reach bigger numbers we tend to think we’re old. Then we look back and realize just how young we were and didn’t experience things we wanted to do because we felt we were old.

That’s some solid life advice…here are the most valuable 7 business coaching lessons I learned from Mark Cuban.

1. Time is more valuable than money

Time is the most valuable asset you don’t own. How wisely you use your time will have far more impact on your life and success than any amount of money.”

This should be the anthem for any entrepreneur.

Early on he’ll tell you he placed too much importance on comparing how much he had in comparison to others. Once he realized time was the far more valuable asset, things shifted. 

He started using money to create more time. Now he appreciates both of them more.

When you love what you do the amount of time you spend doing it is irrelevant.  When you stop exchanging time for money, you value your work so much more and you end up rich.

It happens organically.

You also must carve out time to THINK. 

“I still work hard to know my business. I’m continuously looking for ways to improve all my companies, and I’m always selling. Always.”

2. There’s no reason it can’t be you

No entrepreneur is immune to failure, and Cuban is proud to say he’s had his ups and downs.   

After college, he moved to Dallas where he worked behind a bar, sold software and basically did whatever it took to learn and get ahead.

At one stage he was eating ketchup sandwiches just to survive. 

Early in his MicroSolutions days, the bank called to notify him the secretary whited out the company name and replaced it with her own. She cleaned the bank account out and ran off with $80,000. That was all the money the company had.

He got mad initially but rather than give up… he just doubled down on effort.

“We didn’t die from that wound. I say it to Maverick players and I say it to everybody in business, the one thing in life you can control is your effort. If you’re willing to put in the effort to start the business and you’re willing to deal with the challenges and the fact you might starve or live like a student . . . If you’re willing to fight through those via effort and brain power, then anything is possible. There is no reason it can’t be you.”

3. Selling comes down to connecting and serving

Through hard work and perseverance, Mark learned another valuable lesson.

If you learn to sell, you can pretty much accomplish anything you want. The key to selling anything is the ability to connect with prospects while genuinely serving them and keeping the deals best interests at heart.

“You’re not trying to convince them of anything, you’re trying to show them how you’re going to make their lives easier. There are no favors involved. It needs to be a win-win for everybody.”

That being said, success takes more than just the ability to connect with people. There’s a lot of hustle involved, whether you’re selling your family, friends, garbage bags or million dollar technology deals.

Every ‘no’ gets you closer to a ‘YES’ and it’s just a numbers game. It’s just a question of making enough calls and controlling your effort.

4. Know your competitors

Often founders get tunnel vision as they fixate on growing their business. But, it’s important to stop and smell the coffee once in awhile.

Look around at the competition and what they’re doing and offering.

Mark Cuban is never intimidated by the competition and prides himself on never slowing down and always striving to make his customers happier.

“Work like there is someone working twenty-four hours a day to take it all away from you.” 

How can you dominate the competition if you don’t know what they’re doing or offering? How can you anticipate what they’ll do in the future if you don’t track their trends? 

The only way to ensure you stay ahead is to know your industry better than anyone. This is (and takes) hard work and the good news is hardly anyone else will do it.

“It’s not in the dreaming, it’s in the doing.” 

5. Don’t be a slave to the bank

Mark is passionate about encouraging young entrepreneurs not to use debt to build a business. Especially in the early stages.

In his opinion, 99% of today’s companies should be started without an outside capital injection.

“If you take a loan, you and your customers are no longer the bosses. Your banker and investors are now the bosses. If you hit any adversity, as every startup does, the priority becomes taking care of your banker or investors. You’re no longer in a position to do whatever it takes to survive.”

Most dream of reading their name in the headline “XXXX Raises $15 Million.”

Mistakenly, this is a sign that “you’ve made it,” and most tech reporters won’t pay attention to a business that’s bootstrapped as they’re perceived to be lightweights. 

Contrary to popular belief, raising money is not an accomplishment.

Wherever possible, he always, always, always recommends that you bootstrap your start up.

6. Be nice

“One of the most underrated skills in business right now is being nice”

It’s not a surprise Mark Cuban often gets stopped on the street for selfies and to hear business pitches. He’s renowned for bending over backwards for these people, stopping to sign autographs, listen or smile.

To such a degree that his team often questions him on it. His response is that it’s easier and more fun to be nice than a jerk like so many others in the same position.

He applies this to his business life. It may seem obvious, but “nice” is necessary. Being liked goes a long way, and Mark Cuban is most certainly likable.

“It’s always easier to be nice than to be a jerk. Don’t be a jerk.”

7. What to watch in the future?

Artificial intelligence. 

“I’m telling you, the world’s first trillionaires are going to come from somebody who masters AI and all its derivatives and applies it in ways we never thought of.”

Those that crack the code on AI (and machine learning) will change the world.


They’re going to make Facebook look like a lemonade stand.

He’s currently teaching himself and learning as much as he can about machine learning, deep learning, and neural networks. Subsets of AI.

They’re going to change the nature of work.

Mark Cuban taught himself how to program in the 1980s and that led to his $6 million exit with MicroSolutions at the age of 32.

Cuban taught himself and pursued internet streaming in the 1990s that led to his $5.7 billion exit with at age 41.

So when Mark Cuban tells you he’s teaching himself AI and recently read a book called “Machine Learning for Dummies”…  it’s probably a good idea to pay attention and start reading.

So what is AI? Think of it as machines imitating and adapting human-like behavior. We’re teaching machines to ‘learn from experience’ which is how humans do it.   

The algorithms use computational methods to “learn” directly from the data provided without relying on a predetermined equation as a model.

The algorithms adaptively improve their performance as the number of samples available for learning increases (just like humans, they improve with experience).

Cuban recently read the book “Machine Learning for Dummies” and he says the best book he’s read on the subject of AI and Machine Learning is “The Master Algorithm: How the Quest for the Ultimate Learning Machine Will Remake the World” by Pedro Domingos.

The technology was originally designed to be descriptive. As it advanced, tech became a tool to become predictive.

An example of this is an algorithm someone creates to explain ‘if you do this – then that will happen.’

Now with artificial intelligence, it’s going to another level and becoming ”prescriptive.”

In other words, you will feed information and data to the machine and then the machine is capable of thinking on its own and will not only give you suggestions but multiple recommendations on what you should do with percentage outcomes.

The prescriptive nature of all this is a total game changer for the business world.

“We’re going through the process where software will automate software, automation will automate automation.”

If you don’t understand machine learning and deep learning, now’s the time to get to work, dig deep into it and get ahead of the curve.

You also risk getting left behind if you don’t. 

“There is no reason it can’t be you”

Mark Cuban

I repeat: When Mark Cuban tells you he’s teaching himself AI and recently read a book called “Machine Learning for Dummies”….  it’s probably a good idea to pay attention and start reading.

I most certainly am…

Karl Bryan

Karl Bryan gets clients for Business Coaches...period. He is the editor of The Six Figure Coach Magazine and Chairman of Leader Publishing Worldwide, home of the largest private community of Business Coaches (24 countries and counting) in the world.
His goal is straight forward… to help serious coaches/consultants get more clients and to start using the internet effectively.

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