Straight From the Shark

Business Lessons from Mark Cuban
Dustin Wells - EO Austin

Article by:

Dustin Wells
EO Austin

Dustin Wells is the Chapter President of EO Austin and CEO of Headspring, a software solutions firm catering to Fortune 500 brands. Fun fact: Despite now owning a fast-growing technology company, Dustin actually earned a degree in Fine Arts at the University of Texas, where he studied jazz and percussion. Contact Dustin at [email protected].

As a chapter, we’re committed to hosting the best learning events around, the kind that give our members the tools they need to excel in business and life. During the recent South by Southwest (SXSW) Interactive festival, we had the chance to host an event with none other than Mark Cuban. One of the most successful entrepreneurs around, Mark is known for being the founder of, an enthusiastic owner of the National Basketball Association’s (NBA) Dallas Mavericks and a no-holds-barred investor on the television series, “Shark Tank.”

It’s safe to say that Mark has a lot of insight to offer fellow entrepreneurs, so landing him as a speaker was a huge win. He didn’t disappoint. Mark shared stories about his first business endeavor (door-to- door trash bag sales) and his investment approach (he’s invested in more than 80 startups, some based solely on email pitches), as well as anecdotes about a few of his more memorable experiences (getting to bump Magic Johnson from a flight). All in all, he was funny, uncensored and entertaining ... and he also left me with several lessons that I’ll be applying in my own entrepreneurial journey:

Content—and context—is critical. We achieved the ultimate trifecta for this learning event: a charismatic and highly credible speaker; relevant information for our audience; and perfect timing during SXSW Interactive, an event that has business owners from around the world ready to soak up as much knowledge as humanly possible. Whether you’re looking to fill a room, craft an inspiring blog post or land a contributed article in Forbes, that perfect storm of tailored content and contextual relevancy is critical to cutting through the clutter.

Above all else, be authentic. Mark is one of the world’s most successful entrepreneurs and billionaires, running a multitude of businesses and serving as the centerpiece of an entrepreneur-focused television show. Yet, he showed up to the event in jeans, a t-shirt and sneakers, which he immediately kicked off when he got onstage. In business, where investors put their money behind people more than products, Mark exemplifies two characteristics that are vital for success-hungry entrepreneurs: He exudes passion for his business, and he is unapologetically himself.

Be prepared for the unexpected. As with running a business, it’s not often that things go exactly as planned. While we were expecting a short, solo presentation of sorts, Mark instead asked me to join him onstage for a more informal Q&A session. I never expected to be sitting barefoot on a stage, having a friendly conversation with Mark Cuban! It was unexpected, and required the kind of adapting that’s necessary in entrepreneurship— but the result was an even more interesting and unique experience than we could have hoped for.

Recognize the difference between selling products and selling experiences. As one of the most active and enthusiastic team owners in the NBA, Mark recently announced that the league is wrong about how it conducts its business. It’s not selling basketball … it’s selling the emotional roller-coaster that is watching, ‘live’ sports. Regardless of your industry, customers buy outcomes, results and experiences— not products. Market and sell accordingly.

Don’t forget to have fun. After his first successful business exit, Mark chose to invest not in a big house or flashy new car, but a lifetime pass on American Airlines, saying that the card served as a reminder to “party like a rock star.” Entrepreneurship is a long and bumpy road, but it’s important to step back from the day-to-day grind every once in a while, recognize your successes, and above all, enjoy the ride.

17,000+ Members

213 Chapters

60+ Countries

Stay Connected

Fill out the contact information below to receive EO's newsletter.

    Conditions of EO Membership Application and Renewal:
    Every member who applies or renews their membership agrees to comply with the Policies and Procedures, Bylaws and Code of Conduct of Entrepreneurs' Organization. Current members must complete the online renewal form acknowledging review of the organization's Policies and Procedures, Bylaws and Code of Conduct.