‘An entrepreneur has to adapt to change:’ Q+A with Mark Cuban on building a business

Entrepreneur, investor and media proprietor Mark Cuban is well known for his affiliation with the Dallas Mavericks, being a “shark” investor on the television show Shark Tank, and for being a self-made billionaire. 

He’s not shy in sharing his best advice about what it takes to be a successful business person, having made headlines like “What Advice Would Mark Cuban Give His Younger Self? His Answer Applies to Nearly Every Entrepreneur” and “Mark Cuban: Top advice for young people starting a business.” Today he has launched his first class “Win Big in Business” on the learning platform MasterClass.

In his class on MasterClass, he’ll share in-depth lessons in business, how to spot opportunities for disruption, case studies from his most famous companies, and career moments from ownership of The Mavs to his affordable medicine business Cost Plus Drugs. Members will get a look at why he sold his majority stake in the Dallas Mavericks while staying on as president of basketball operations, why he chose not to run for president of the U.S., how Cost Plus Drugs has disrupted a legacy industry, and his method for evaluating potential investments on Shark Tank. 

He’s been an entrepreneur since the age of 12 when he sold garbage bags door-to-door. Later on, he took advantage of the dot-com boom, co-founding Broadcast.com, which he later sold to Yahoo for $5.7 billion. 

We asked Cuban why he’s decided to do the MasterClass, what other advice he has for entrepreneurs, and how leaders can reach their maximum potential. 

Answers were edited for clarity and flow, with additional tidbits from the MasterClass for each question.

Why did you decide to make a class on MasterClass and what do you hope members get out of it?

I love helping entrepreneurs reach their dreams. It’s the exact reason I have done Shark Tank for 15 years. I’m excited to teach MasterClass members and hopefully inspire them to do even more. I hope members walk away from the class feeling inspired to go out and crush it. Being an entrepreneur can be all-consuming. I want to let them know that I had to grind it out and if they do the same amazing things can happen for them. 

I give details that I haven’t shared before about what’s worked for me, and the support I’ve given portfolio companies like Wondry Wine, the Mavs and Fireside. For this, I worked closely with the MasterClass team to identify case studies from my companies and big career moments to show a different take on spotting opportunities. There’s some sort of lesson to be learned from every experience in life.

Wondry Wine, a Black-owned wine label, made $1.1 million in revenue in 2023, a noticeable jump from its 2022 appearance on Shark Tank, when the owners told investors they had $250,000 in 11 months of lifetime sales, including $60,000 in profit. The couple’s pitch landed them $225,000 of Cuban’s money in exchange for 15% of the Dallas-based company. Duo Whitney and Chaz Gates are featured in Cuban’s class on MasterClass. “We use the term business life coach because working with Mark as a mentor, sometimes his advice is very different than what we expect,” said Chaz Gates. “He’s that voice of reason or parent that steps in.”

You talk a lot about spotting opportunities for disruption. Is that a good place for an entrepreneur to start to build their own business?

Definitely. I’ve been able to see around corners because of my commitment to always learning. When you can focus and learn, you can spot new opportunities and sometimes that leads to massively disrupting an industry. 

Cuban says in his class on MasterClass: “When I walk into a room, when I walk into a business, when I read about something, I always ask myself: could I do a better job? If I think I can, and I’m willing to put my money where my mouth is, I go for it.” For example, he describes how buying the Dallas Mavericks back in 2000 wasn’t to be in the business of basketball, it was to be in the business of entertainment. “You go to a game not to watch the game, you can do that at home. You go to a game to feel the energy, yell, scream, to let it out. We have to be the answer to ‘what do you want to do tonight?’”

The top job advice I always hear is to go out and network. In this class, you say it‘s not as useful as one might think. Why is that?

Everyone has to work in the way that is best for them. But in my experience, networking is just OK. Focusing on learning and gaining expertise goes much further toward enabling success for entrepreneurs. 

Extract from Cuban’s class on MasterClass: “A lot of people talk about networking. ‘Go out there and network!’ It can help in sales or to get a job … but let me just tell you a secret of rich people. Their best ideas, they ain’t telling you. They’re keeping them for themselves. If there were short cuts, everyone would just do them.”

Aside from networking, Cuban encourages workers to get comfortable with the interview process. Cuban admits he is “horrible at hiring and interviewing people.” But when he does do it, he asks questions like what’s one thing you’ve failed out, what’s one thing you’ve succeeded at, why did you leave your last job, what’s the best culture of a company you’ve worked at, who’s the best manager you’ve ever worked for. “I want to get them talking about their positive or negative experiences so that I can understand whether or not they are going to be a fit.” One tip for employers he has? There are no home run hires. “The biggest mistake I see my portfolio companies make… ‘we just hired this fantastic, incredible, amazing, stupendous person to be our new director of marketing, of sales, head of revenue generation.’ They get so excited, and I just drop my head and say ‘oh fuck, here we go again.’”

In the class, you share how you hate corporate buzzwords like KPI – something we’ve reported on too including how it can be a barrier to entry in the business world. Do you think a new entrepreneur has to tackle this learning curve?

If it’s industry-specific, you do have to learn it. But if it’s general buzzwords, you hurt yourself using them. I would rather work with someone who has original thoughts, rather than trying to pretend they are knowledgeable by using those buzzwords.

Extract from class: Another tip for those seeking success in the business world when you’re not sure about something? “Google it. Read every single thing about that idea, companies in that business, their financials. Whatever you can find,” he says.

You mention entrepreneurs have to optimize processes, what are your thoughts on AI to do that?

An entrepreneur has to adapt to change. As technology continues to evolve, it’s increasingly important to work with the technology and leverage it to your advantage. AI can be a great tool to do that. 

A part of that requires trust, though. “In this day in age, the number one product or service for every single company in the world, no matter what it is you’re actually selling, is trust,” says Cuban. 

You figured out entrepreneurship at the early age of 12. Could someone enter the business world at 40, 50 or 60 years old instead?

Of course they can. Age ain’t nothing but a number. If you know your stuff and are prepared, you can do anything. 

But, he does admit that he approaches business a little differently now that he has three kids. “At some point in every one of our lives, we realize the most valuable asset we own is our time,” says Cuban in his class on MasterClass. “Are you willing to give up the time, are you willing to go to your family and say there is not going to be work-life balance anymore? Those are the things that tend to stop us more than anything. Now for me, with three kids, I value risk differently. My most valuable asset is time.”

Any golden tips to share for succeeding at business?

I partnered with MasterClass because I want members to get an edge. You never know where that one bit of knowledge that could help your business comes from. Hopefully this class will propel members to help them reach their goals and dreams. 

To end his class on MasterClass, Cuban discusses income inequality. As a tip for employers, he says to give shares of stocks to employees. “That’s how things will change in this country,” he said. “That’s what I, as an entrepreneur, always encourage, if not demand, from my companies to give stock to every single one of their employees. If things turn out great, everyone celebrates. It’s not hard. You just have to do it.”