Building Bold Ventures: Mark Cuban on Strategy, Storytelling, and Impact

Mark Cuban, a native of Pittsburgh, PA, a graduate of Indiana University, and now a Dallas, TX resident has always been an entrepreneur. 

From selling and trading baseball cards, selling garbage bags and magazines door-to-door, to starting a business buying and selling stamps at age 16, there have been few years in his life when he wasn’t starting or running a business. 

After graduating from IU, a friend suggested he come to Dallas. Off Mark went to live in “The Village” with five roommates, getting only the floor in the corner of a bedroom as his new “home.” Starting as a bartender, he was not there long before he got a job at one of Dallas’ first retail software stores, Your Business Software. 

He spent nine months doing everything from learning how to code, supporting and installing every type of business software and of course, making sure the store opened on time. That went well until he made the executive decision to turn over the store opening duties to a peer so he could pick up a check for a sale. 

He was fired. 

Mark decided it was time to start on his own, the next day, MicroSolutions was founded… 

With no money and still sleeping on the floor, Mark was relentless until he found his first customer, Architectural Lighting, who fronted him the money for the software they needed. That advance was all Mark needed. Over the next seven vacationless years, MicroSolutions became a national leader in Systems Integration and custom applications for local and wide area networks, making it near the top of LAN Magazine’s LAN 100. 

Growing to 80 employees, never having a losing month of operations and nearly $36M in annualized sales, in 1990, MicroSolutions was sold to CompuServe, a subsidiary of H&R Block for $6M. 

At that point Mark “retired ” to investing in public and private companies.  His knowledge of the networking industry led to success and brought returns of 80 percent and more each year. He used that track record to briefly build a hedge fund, for which he got an offer he couldn’t refuse and sold within 12 months. 

After a brief stint in LA to have fun taking acting classes and doing fortunately long-forgotten commercials and B movies, he returned to Dallas. 

During a lunch with a college friend, Todd Wagner, they discussed how they might use “this new thing called the internet” to listen to broadcasts of IU basketball games in Dallas–at that time, an impossibility. Using his knowledge of networking and Todd’s extensive background on law and business, they started Audionet.com, the first commercial streaming company in the world. 

AudioNet grew quickly and soon became Broadcast.com, adding video and much more, going public in July 1998 with what would be the largest first day jump in share valuation in the history of the stock market! Broadcast.com was the largest multimedia site on the internet, without a close second. After being pursued by multiple possible acquisitors, Broadcast.com was sold for $5.7B in stock to Yahoo Inc. 

Once the deal closed, Mark became concerned that the internet stock boom could become a bust, so he hedged his stock, putting on a long short collar that would go on to be called “one of the top 10 stock market trades of all time.” 

It was at the same time Mark purchased the Dallas Mavericks for $285M. The Mavs would have the second-best record in the NBA during his ownership tenure, got to the NBA Finals in 2006, and won the World Championship in 2011. 

Mark changed the nature of ownership of a professional team. He sat with fans. He took a vocal stand on officiating, getting fined millions of dollars. He also led to significant changes in how teams were operated. He was the first to bring in Player Development coaches. At the time he was criticized, but it is now done by every team. He had the NBA change the clear path rule to 2 shots and the ball after showing the league the math behind the incentives to foul. He added mics to the rim of the American Airlines Center, expanded in arena entertainment and fan engagement. He considers his greatest failure during his tenure as Governor of the Mavs to be his inability to help the NBA improve the officiating, despite spending more than $3M in fines. 

Mark sold majority control of the Mavs in 2023, but continues to be actively involved with the team. 

In addition to the Mavs, Mark continued to be active as an entrepreneur and investor. Along with Phil Garvin, in 2001, they started HDNet and HDNet Movies, the world’s first all High-Definition TV network. 

That started the path for Todd Wagner and Mark to focus on building the first fully integrated media and entertainment company. Adding Landmark Theaters, starting 2929 Productions, HDNet Films and Magnolia Pictures, Todd and Mark set a new entertainment path. 

The first movie Mark personally greenlit, in 12 minutes, all via email, was “Enron: The Smartest Guys In the Room.” It went on to be nominated for an Academy Award. The next movie, from 2929 Productions, was “Good Night and Good Luck,” nominated for six Academy Awards. 

Mark and Todd teamed to create a variety of firsts: the first movie released on TV, theaters, and on DVD, came from 2929 Productions, as were the first movies released to hotels branded as “While in Theaters.” 

Landmark Theaters was sold in 2019, HDNet not long after. Magnolia Pictures and 2929 continue to thrive. 

Mark’s accomplishments extended to other areas as well. 

He first appeared as a “Shark” on ABC’s Emmy Award-winning hit business show “Shark Tank” in 2011 and quickly established himself as one of the most popular and tough Sharks throughout his tenure, investing millions of dollars in hundreds of small businesses. He’s been nominated nine times for an Emmy for “Shark Tank,” which includes four times for Outstanding Host of a Reality or Competition Program and won the Emmy as an Executive Producer in 2024 for Outstanding Structured Reality Program. The vast number of companies he’s invested in are featured on www.markcubancompanies.com. His last appearance on the program will be during season 16 in May 2025. 

In 2015, in response to vestibular issues he was experiencing, he partnered with the doctors who currently operate DizzyAndVertigo.com to integrate Vestibular Rehabilitation software and VR Goggles to create a solution that offers an alternative to special devices that cost $190K. The solution continues to be used and has helped thousands of people get relief from dizziness. 

In 2019, Mark co-founded Costplusdrugs.com.  Its launch on Jan 19, 2022, with transparent pricing and a limited markup, has fundamentally changed the pricing of medications in the USA. 

Other awards Mark has earned include being named to the Texas Business Hall of Fame, the Horatio Alger Award, the SXSW Hall of Fame, Ernst and Young Entrepreneur of the Year, and GQ Man of the Year. 

He is married and lives in Dallas with his wife and three children.

Lucas Shaw is the managing editor for media & entertainment at Bloomberg News, overseeing a global team that covers businesses such as Hollywood, music, video games, and social media creators. He is the author of the weekly newsletter Screentime and a regular contributor to Bloomberg Businessweek magazine. A native Angeleno, Shaw is a weekly guest The Town podcast, as well as frequent guest on National Public Radio.