Straight from the Shark: Business Lessons from Mark Cuban

By Dustin Wells, an EO Austin member and CEO of Headspring

During the recent SXSW Interactive festival, EO Austin had the opportunity to host a event with none other than Mark Cuban. One of the most successful entrepreneurs around, Mark is most well-known for being the enthusiastic owner of the Dallas Mavericks and no-holds-barred investor on the TV series Shark Tank.

It’s safe to say that Mark has a lot of experience and insight to offer fellow entrepreneurs. Mark shared stories about his first business endeavor (door-to-door trash bag sales), his investment approach (he’s invested in more than 80 startups, some based solely on email pitches) and anecdotes about a few of his more memorable experiences (getting to bump Magic Johnson from a flight).

He was funny, uncensored and entertaining — and he also left me with several lessons that I’ll be applying along my entrepreneurial journey.

  • Content — and context — is key. We achieved the ultimate trifecta for this event: a charismatic and highly credible speaker, relevant information for our audience of entrepreneurs and 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 key 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 a star of a successful 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 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 according to plan. While 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 some adapting as is typical in entrepreneurship — but the result was an even more interesting and unique experience than we had hoped for.
  • Recognize the difference between selling products and selling experiences. As one of the most active and “enthusiastic” team owners, Mark called out that the National Basketball Association (NBA) is wrong about 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, experiences — not products. Market and sell accordingly.
  • Don’t forget to have fun. After his first successful exit, Mark chose to invest not in a big house or new flashy 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 successes and enjoy the ride.

Dustin Wells is Chapter President of the Austin chapter of the Entrepreneurs’ Organization (EO), and CEO of Headspring, which provides tailored software solutions, helping Fortune 500 brands take control of their information to better serve their customers.

Categories: Best Practices EO News FINANCES


3 Responses to “ Straight from the Shark: Business Lessons from Mark Cuban ”

  1. Annette Warren on

    I agree with the lessons learned and its refreshing to read that Mark Cuban also believes in being authentic and having fun in your business. Being authentic is being who you are and trust is a huge intrinsic value in business. Having fun is the passion that drives your business and the people in it. Great article Dustin!


    The unexpected and the experience are quite important to the enterpreneur in developing a niche in any area of business.
    The unexpected keeps the entrepreneur anticipatory and opens the door for creativity and innovation which makes for uniqueness and originality.
    Experience as used in the sale of product or service pictures the customers’ need and satisfaction as the reason for the product or service.
    The impact is usually on increased as well as sustained patronage.


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