Book Review: How to win at the sport of business by Mark Cuban

Mahi Sall
10 min readFeb 1, 2021


When the student is ready the teacher appears

Meet your coach now if you are ready to take the lessons…

Pic: Amazon

This book is for you if:

  • You are an entrepreneur regardless of the stage you are currently at;
  • You are a young professional or fresh grad feeling lost in finding your calling;
  • You help anyone of the preceding groups e.g. as a mentor, coach, etc.

Imagine playing a sport that has no end, no set rules, every opponent is looking to take you down as fast as he or she can. Worse you may not all your adversaries… Well, that’s the sport of business, the ultimate sport. It is the core idea of this book, which is a collection of blog posts written by the author. It covers with brutal honesty the fundamentals of starting and running a business, the challenges entrepreneurs face, and is packed with battle-tested business and life lessons straight out of the author’s own journey.

PART ONE: The Dream

I did it too. I would drive by big houses and wonder who lived there — every weekend I would do it. What did they do for a living? How did they make their money? Someday, I would tell myself, I would live in a house like that. I read books about successful people. In fact, I read every book or magazine I could get my hands on. I would tell myself that one good idea would pay for the book and could make the difference between me making it or not.

Such are the opening words of part one of the book in which Cuban tells the multiple short-lived jobs he took after graduating from Indiana University, the mindset he developed while going through tough times, and his humble beginnings as an entrepreneur after being let go from his club bartender job in Dallas.

You may want to pay a close attention to the lessons and anecdotes coming up in the lines ahead particularly if you are currently stuck in a job that you hate, considering making the entrepreneurial leap or at the helm of an early-stage startup.

Finding meaning in struggles:

Stars seldom align. Far often than not, the path to one’s dream job will not be a straight line. After graduation Cuban took multiple jobs but none did fit his dream job’s template. Whenever the going got tough, he rationalized and told himself I am still at school but now I get paid while learning. In his own words:

We all want our dream job or to run our own companies. The truth? It is a lot easier said than done. We need jobs that pay the bills, and we can’t wait out the search for the perfect situation.

Hunting for new ideas or the power of reading

Cuban was a voracious reader, always on the lookout for new ideas that he hoped would give him the edge. He wrote:

I would continually search for new ideas. I read every book and magazine I could. One good idea would lead to a customer or a solution, and those magazines and books paid for themselves many times over. Some of the ideas I read were good, some not. In doing all the reading I learned a valuable lesson. Everything I read was public. The same information was available to anyone who wanted it. Turns out most people didn’t want it. Most people won’t put in the time to get a knowledge advantage.

Resourcefulness is the ultimate resource — Tony Robbins

After being fired by his employer, Cuban decided to start his own business — unprepared and with no resources. He landed his first customer using a non-orthodox yet powerful sales arbitrage technique. This is how the deal unfolded:

Architectural Lighting (prospect) was looking for a time and billing accounting system to allow them to track their work with clients. I don’t remember the name of the software package I told them about, but after going out to meet with them it came down to this: I offered to refund 100% of their money if the software didn’t work for them, and I wouldn’t charge them for my time for installing and helping them. In return, they would put up the five hundred bucks it would take for me to buy the software from the publisher, and I could use them as a reference.


Partnering up with capable people and hiring missionaries as opposed to mercenaries can go a long way in any startup venture.

Cuban compensated for his lack of organizational skills by teaming up with someone who was gifted with the missing expertise. He also succeeded to convince a friend then waiter at steakhouse to take a pay cut and join him. The chemistry between the two got so good that they moved onto his next venture together. Speaking about mercenaries, Cuban learned his lesson the hard way: he tells the outrageous story of how their secretary managed to defraud $83k out of the $85k the company had at the bank before disappearing for good!

The foundational layer of starting a business does not end with part one. Let’s now turn the page onto part two to discover the additional pieces, and Cuban’s rules for startups and 12 mantras for success.


Success in the sport of business is all about having the edge Cuban wrote. As an entrepreneur you will make mistakes and experience failures. The key is to learn from them, from those of other people around you and from the best in your field. The only thing you can control is effort as measured by the goals you set and results you get instead of the number of hours you spent at work. In the end it will not matter how often you failed. In business Cuban wrote you only have to be right once. How does one get it right? The next lines provide some clues:

  • Learn to preempt competition by always asking yourself how someone could take you out of business. Is it Price, Service, Ease of use?
  • Operate as though you were going against the Googles or Facebooks in your industry. Watching the best taught me how to run my businesses he wrote;
  • Be honest with yourself, know what you are good at and where you need help. Seek feedback to figure this out;
  • Know what the core competencies of your business are and double down at being the absolute best at executing them;
  • Learn to let teammates take the ball and run with it, aka delegate;

About raising capital, Cuban teaches that there are only two reasonable sources of capital for startup entrepreneurs: their own pocket and those of their customers. Coming from a shark, this may sound crazy but here is how he backs it up:

Far more often than not, raising cash is the biggest mistake you can make. The minute you ask for money, you are playing in their (investors) game — they aren’t playing in yours. You are at a huge disadvantage, and it’s only going to get worse if you take their money. The minute you take money, the leverage completely flips to the investor. They control the destiny of your dreams, not you. Investors don’t care about your dreams and goals. They love that you have them. They love that you are motivated by them. Investors care about how they are going to get their money back and then some.

Four golden nuggets about customers

  • Think of YAHOO as You (the customer) Always Have Other Options. Cuban warns: treat them like they own you, because they do, before adding: I make sure that all the customer service emails get forwarded to me. If someone is complaining, I want to know about it, and I want to get it fixed quickly. Happy customers might tell one person (…). An unhappy customer starts a blog, writes about how unhappy he is, takes out an ad on search engines to let people who are looking for the product know how mad he is, starts an email forwarding chain asking people to boycott the product, does a YouTube video about it and games YouTube to make it one of the Top 10 most-viewed videos … You get the picture.
  • Don’t rely on customers to create the future roadmap for your product or service. That’s your job. They can tell you the things that are broken and how they want to be made happy. Listen to them. Make them happy.
  • Convenience: make sure that your product (or service) is the easiest to experience and to sell because people generally follow the path of least resistance.
  • In sales should you take “No” for an answer? Widespread advice says you should persevere with prospects. Cuban advocates a contrarian approach: Every no gets you closer to a yes. But before walking away ask for feedback. Here is the script: thank you for taking the time to listen/read. Would you mind sharing with me what you didn’t like about the product or why you like the product you chose? Substitute service to product as it suits you.

Twelve Cuban Rules for Startups

Here are my top 6.

  1. Don’t start a company unless it’s an obsession and something you love. If you have an exit strategy, it’s not an obsession;
  2. Sales cure all. Know how your company will make money and how you will actually make sales;
  3. Know your core competencies and focus on being great at them. Pay up for people in your core competencies. Get the best. Outside the core competencies, hire people that fit your culture but are cheap;
  4. No offices. Open offices keep everyone in tune with what is going on and keep the energy up;
  5. Keep the organization flat. If you have managers reporting to managers, you will create politics;
  6. Make the job fun for employees. Keep a pulse on the stress levels and accomplishments of your people and reward them;

Twelve Cuban Mantras for Success

  1. Time is more valuable than money;
  2. Commit random acts of kindness;
  3. No balls, no babies. Translation: once you are prepared and think you have every angle of preparation covered, you have to go for it;
  4. Work hard, play hard;
  5. Don’t let fear be a roadblock, instead use it as motivation;
  6. Expect the unexpected, and always be ready;
  7. It’s okay to yell and be yelled at;
  8. Everyone gets down; the key is how soon you get back up;
  9. It’s not whether the glass is half empty or half full, it’s who is pouring the water;
  10. It’s not in the dreaming, it’s in the doing;
  11. Pigs get fat, hogs get slaughtered. Translation: in business do not be greedy, else you’ll soon find out that no one wants to do business with you anymore;
  12. You only have to be right once;

Career/Life hacks

What lessons does Cuban offer? Next lines provide an overview.

  • You don’t need to have all the answers or focus on one thing (at 21). You should be trying a lot of things until you find the one thing you really love to do and are good at. When that happens, you will be able to focus;
  • Going to college should be about learning how to learn and recognizing that learning is a lifelong endeavor. School isn’t the end of the learning process, it’s purely a training ground and beginning;
  • The greatest obstacle to destiny is debt. Financial debt is the ultimate dream killer;
  • If you can sell, you can get a job — anywhere, anytime. Sales is the most important job in every company. There has yet to be a successful company that has survived with zero sales;
  • The cheaper you can live, the greater your options. Your biggest enemies are your bills;
  • Take lots of chances. Creating opportunities means looking where others are not;
  • How to figure out if you are in the right job? If it matters how much you get paid, you are not in a job you really love. If you love what you do so much that you are willing to continue to live like a student in order to be able to stay in the job, you have found your calling;
  • Figuring out how to be the best: when you are the best at something, the demand for your services will grow;
  • Start the day motivated with a positive attitude because you are going to screw up. We all do;
  • Ultimate decision-making question: ask yourself What Will You Remember When You are 90: the regret or the satisfaction for having done it?

The Author

Mark Cuban needs no introduction. Just in case his name did not register with you, Cuban is the owner of the NBA Dallas Maverics and a shark — one of the investors sitting on the US reality TV Show “Shark Tank” where entrepreneurs pitch their business to raise funding.

My top 5 quotes from the book

1. Every no gets me closer to a yes — Mark Cuban

2. The worst evaluator of talent is a player trying to evaluate himself — Don Nelson

3. As entrepreneur, far more often than not, raising cash is the biggest mistake you can make — Mark Cuban

4. The only thing any entrepreneur, salesperson or anyone in any position can control is their effort — Mark Cuban

5. Everyone has got the will to win; it’s only those with the will to prepare that do win — Bobby Knight

My take on the book

How to win at the sport of business is one of those books I keep going back to from time to time. Not only I use it for my own sake, but I also revisit it when working with entrepreneurs. Written in a blogish style, the content is easy to grasp and the lessons/principles backed up by real-life stories. Above all the message is not sugar-coated and the book is by no means a promotional material geared to sell the reader something.

Got feedback? I’d love to hear your thoughts.



Mahi Sall

Fluent in Fintech-Bank Partnerships | Advisor | Ambassador| Audiobookaholic