How Entrepreneur Mark Cuban Rebounds From Career Setbacks

The billionaire investor says he’s always in learning mode

August 4, 2021
Entrepreneurship, Innovation

Over a lifetime of entrepreneurship and taking risks, billionaire and NBA owner Mark Cuban has rebounded from more than a few setbacks – getting fired from several jobs early in his career, being accused and cleared of insider trading, and guiding his NBA team, the Dallas Mavericks, through social justice issues and even allegations of sexual harassment at the organization.

Those challenges have been tremendous learning opportunities, Cuban told Dean Bill Boulding in an interview streamed for Duke University’s Fuqua School of Business alumni.

For many people, Boulding said, an incident like getting fired could shatter their confidence.

“Not for me. It was the best thing that ever happened to me,” Cuban told Boulding. “I learned so much about what not to do, how not to manage, how important certain things are.”

Cuban said he wasn’t fazed even after the CEO of a software company didn’t just fire him, but also ragged on his polyester suits and hand-me-down shirts (see clip).

“I learned it’s not how you look, it’s what you can do,” Cuban said. “You just have to go out there and do the work. And if people do the work you know, maybe they’re rough around the edges – you can work on that side a lot easier than people who just aren’t motivated to do the work.”

An early entrepreneur
Cuban described his beginnings in entrepreneurship as selling garbage bags door-to-door in his neighborhood at age 12 to earn money for new sneakers. He has since started and sold digital media companies and a hedge fund, has invested in numerous startups, owns a major sports franchise and is now a leading philanthropist. One of his first firms and biggest successes,, pioneered online video and audio streaming.

Along the way, people have doubted his ideas, many going so far as to call him “an idiot,” he told Boulding. So what is it, Boulding asked, that makes Cuban such a successful entrepreneur?

“Learning, learning, learning,” he told Boulding, whether it’s teaching himself how to create blockchain smart contracts, or watching tutorials on neural networks and machine learning. “I realized early on, particularly with technology… there were the people who invented any given particular technology, and then there’s everybody else. And, once [my] invention was released, I was tied with everybody else, and from that point on, it was only a question of how hard I was willing to work to learn.”

He also pays attention to historic tech deals and how they have come about, as history might sometimes repeat itself, he said.

“Steve Jobs said it best,” Cuban said. “He said everything is remix, and that’s so absolutely true. If you look at the early days of Apple, they copied so much of what Xerox and Xerox PARC did, and Bell Labs did, and then they just extended it a little bit, in a way that they thought customers would want. And that’s really the way I look at things. You know if I look at existing technologies, I say, OK what applications can take place that aren’t being done now?”

Advocating for change
In addition to trends in business and tech, Cuban is outspoken on many other issues. Years after being cleared of insider trading by the Securities and Exchange Commission, Cuban is still challenging the commission to create clearer guidelines for investors. He temporarily stopped the Mavericks from playing “The Star-Spangled Banner” to support players’ concerns over what the anthem represents.

After reports of sexual harassment inside the Mavericks organization, Cuban said he realized his own management mistakes and committed to changing the organization’s culture. He evaluated his own interactions with colleagues and adopted the mindset that treating people equally does not mean treating them the same, he told Boulding.

“That’s actually a quote I got from a book by a woman named Joan Williams,” Cuban said (see clip). “I always thought that equality was a math equation. If I said something stupid to a white male I could say something the same exact line to a white woman or Black woman or Asian woman, and that was treating everybody equally. And that’s not the right approach. The right approach is that we’re all different, and treating people equally means giving them equal opportunity … Treating people equally means treating them individually and trying to understand who they are, what their goals are, and putting them in a position to succeed.”

Cuban is perhaps best known as an investor with a starring role on ABC’s “Shark Tank,” a reality show on which entrepreneurs propose new ventures. Despite having made lucrative investments in some of the show’s candidates, money is not why he joined the “Shark Tank” cast, Cuban said.

“I do it because it sends the message to kids and entrepreneurs of all ages that if somebody from a small-time town in Idaho or North Carolina can find their way onto the carpet to pitch to the sharks, then anybody can,” he said.

This story may not be republished without permission from Duke University's Fuqua School of Business. Please contact for additional information.

Contact Info

For more information contact our media relations team at