How To Win At The Sport Of Business According to Billionaire Entrepreneur Mark Cuban

by Michelle Velan

Photo by Glenn Carstens-Peters on Unsplash

How To Win At The Sport Of Business is Mark Cuban’s account of the lessons he learned and the habits he adopted that helped him change his mindset and go from broke and aimless to a focused billionaire.

I recently finished Mark Cuban’s book, How to Win at the Sport of Business: If I Can Do It, You Can Do It

It was inspiring and filled with actionable insights. In short, I loved it. Here are some of my favourite highlights and quotes from the short read.


1) It’s always the littlest decisions that have the biggest impact. We all have to make those calls to follow orders or do what we know in our heart is right. When faced with this situation, listen to your instinct and do what you know is right.


2) Everyone is a genius in a bull market. Don’t be fooled by your success if you’re just following the trends.


3) Focus and win the battles you’re in before taking on new ones. If you take on new opportunities before you’ve won the one you’re in, you’re essentially giving up. You can drown in new opportunities.


4) “Never settle. There is no reason to rush.” Take your time to find the job you like, your life partner, or anything meaningful that you’re pursuing. Don’t feel rushed by other people’s timelines.


5) Start the day motivated and with a positive attitude. Remind yourself that you’re going to enjoy the day.


6) Only start a business if it’s an obsession. If you have an exit strategy it’s not an obsession


7) Know your core competencies and focus on being the best at them. Hire top talent for people who are good at your core competencies.


8) Learn to sell. In life and business you’re always selling – to your prospects, investors and employees. To be the best salesperson put yourself in the shoes of the person to whom you’re selling. Don’t sell your product. Solve their problems. Add real value. The best salespeople are the ones that customers trust.


9) Customers want to see that you have other customers. When Mark started MicroSolutions he did the work for his first customer free – only charging them the cost of the software.


10) “Everyone has got the will to win; it’s only those with the will to prepare that do win.” Mark Cuban paraphrasing Bobby Knight. This is what he looks for in business partners and for entrepreneurs he invests in. When he was starting out in his career, he read everything he could get his hands on to learn and get a competitive edge. He assumed that since everything was available to the public, it wouldn’t give him a competitive edge, but he quickly learned that most people don’t take the time to learn. If you invest in continuous learning, you will be ahead of the game.


11) “Your customers can tell you the things that are broken and how they want to be made happy. Listen to them. Make them happy. But don’t rely on them to create the future road map for your product or service. That’s your job.”


I love this. Too often startups look to their customers for answers on everything. It’s important to get feedback and ensure you’re adding value, but ultimately you need to have a vision and conviction around it. No one wants to follow someone without vision.


12) Don’t get caught up in how many hours you work. Judge success based on having goals and measuring your results. Hard work is needed, but focus on what you get done. What do you need to do to deliver for your client? Do you understand your product gaps? How will you reach new customers? How will you get existing customers to return?


13) “Business happens over years and years. Value is measured in the total upside of a business relationship, not by how much you squeezed out in any one deal.” Many people fail because they get too greedy. Every good deal has a win win solution. He hates when people try to squeeze the last penny out of the deal. You may think you got a “good” deal but people will be looking for ways to never do business with you again.


14) Great companies start without investors. He suggested starting small and growing slowly. The minute you ask for money you’re at a huge disadvantage and the leverage flips to the investor. Investors care about how they’re going to get their money back.


Be mindful when making up numbers and calling them expected returns for the investors. Any investor worth anything knows you’re making up your numbers and they’re worthless. That’s not to say they won’t be expected or that they’re not worthwhile, it’s about being aware of this dynamic and demonstrating critical thinking when explaining how you arrived at them.


It makes sense if you can pull it off, but it’s not possible in some cases to start without investment. WeWork was so well funded that they were easily able to invest in revenue generating activities and they ended up driving competitors out of the space. The whole paradigm of many industries has changed and you have to be honest with yourself on the nature of your industry. Ideally, if possible, you want to avoid investment but it’s not always possible and if you avoid it too long, you can miss out on opportunities.


15) “The beauty of success, whether it’s finding the girl of your dreams, the right job or financial success, is that it doesn’t matter how many times you have failed, you only have to be right once.”


16) Commit random acts of kindness.


17) Time is more valuable than money. When considering if he’ll do something, he asks himself how he’ll feel about doing or not doing the thing at 90.


18) Don’t let fear be a roadblock. Everyone has it, just don’t let it hold you back.


19) Everyone gets down, the key is how quickly you get back up. There were many days where he felt unmotivated, didn’t want to do the work, but he pushed through.


20) It’s not in the dreaming, it’s in the doing. Everyone has the ability to be successful, but you have to act. Most people don’t act.

Explore the world of Wondersource with
our free resource of short and long reads