Mark Cuban on How His First Job Led Him to Entrepreneurship — Does This Apply to You?

HOUSTON, TX - APRIL 18:  Dallas Mavericks owner Mark Cuban waits on the court prior to the start of the game between the Dallas Mavericks and Houston Rockets during Game One in the Western Conference Quarterfinals of the 2015 NBA Playoffs on April 18, 2015 at the Toyota Center in Houston, Texas.
Scott Halleran / Getty Images

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It may seem as if outspoken billionaire Mark Cuban has always been an entrepreneur — and for the most part, that is true — but like most Americans, he actually started out in the corporate rank-and-file. That didn’t last very long, though.

Cuban was able to identify fairly quickly that his true personality wasn’t really suited for corporate America and that if he was going to thrive, he would have to do it on his own. So, what were the indicators that gave Cuban his heads-up, and might they apply to you? Read on to learn more.

Cuban’s First Corporate Experience

As Cuban told Trevor Noah on his “What’s Now” podcast, he signed on with Mellon Bank immediately after graduating from Indiana University in 1981. At first, it seemed like a dream job, and Cuban felt that he fit in completely. He even felt comfortable enough to send articles to the bank’s CEO and form a “rookie club” that would meet, drink and network with upper-level executives.

All seemed to be going well as Cuban thought he was making a name for himself and helping the company to progress as well. But those days didn’t last very long. At one point, as he told Noah, his boss was yelling at him nonstop, telling him to stop with all his crazy ideas and essentially fall in line.

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That was one of the first indicators Cuban had that if he wanted to help shape and mold a company, he might have to do it himself.

Cuban’s Second Rank-and-File Job

Cuban’s second “wake-up call” was his job with a PC software retailer called Your Business Software. After working there for nine months, the future billionaire was fired in Cuban-esque fashion — for trying to make a deal.

As Cuban told the story in a 2017 podcast, he left the store unattended while closing a $15,000 deal with a client without informing his boss. Once again, his entrepreneurial spirit pushed him beyond the rules that apply to employees, and he paid the price for it — at least in terms of keeping that job. In reality, the lessons he learned there solidified his own beliefs that he should be doing things his own way.

What Are the Personality Characteristics of an Entrepreneur?

From Cuban’s experiences, an entrepreneur is someone who has their own ideas about how things should be done, and they aren’t shy about expressing them. While this can lead to problems in a corporate setting, it’s essential for survival as an entrepreneur.

As Cuban himself told WIRED in late 2023, “I was a lousy employee because I was a know-it-all…I was an entrepreneur at heart, and I always thought I had a better idea [for how to do things].”

According to the York School of Continuing Studies, these are the 10 main signs that you might be an entrepreneur at heart:

  • You feel stuck
  • You want variety
  • You want to be your own boss
  • You constantly look for new ideas
  • You like doing the hard work
  • You’re a problem solver
  • You believe in upskilling and reskilling
  • People look to you for guidance and inspiration
  • You’re organized and a good communicator
  • You’re passionate

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As you can tell by reading the list, Cuban himself has many, if not all, of these traits. 

Are You an Entrepreneur at Heart?

Many people dream about being an entrepreneur, but it’s not for everyone. Without at least some of the personality traits listed above, you might find it far more difficult than you imagine to be an entrepreneur.

However, if making your own way and being in charge of all of your decisions sounds more suited to your personality than simply showing up for work every day and doing what you’re told, you might have the entrepreneurial spirit after all. 

Of course, simply wanting to do things your own way, as Cuban described, isn’t enough to guarantee success as an entrepreneur. In addition to being passionate about your ideas, you’ve got to have the mental toughness to successfully implement them. You also need the financial wherewithal to budget and fund your dreams while ensuring that they are good ideas in the first place. 

But if you’ve got what it takes to be an entrepreneur, it can be a very satisfying life. Cuban thinks that entrepreneurial skills are beneficial for everyone, even if you don’t end up running your own company, and he recommends learning them as early as possible.

As he told CNBC Make It in 2018, “Those are skills that are valuable to everyone and are difficult to pick up in school.” His final words of advice about the subject were, “Learn about things that are interesting to you. The quest for knowledge opens up opportunity to do things you may not have thought possible.”

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