How Mark Cuban Sold His Way to a Billion Dollar Fortune

We all know Mark Cuban as the billionaire entrepreneur and investor he is today. But at heart, Mark Cuban is a salesman. After all, he told Wired that if he lost his entire fortune tomorrow, the first thing he would do would be to go out and get a sales job. Despite all the media coverage he gets as a television star and NBA franchise owner, there’s a lesser known story of how he came from humble beginnings and sold his way into a billion-dollar fortune. 

It all started when Cuban was a 12-year-old going door-to-door selling trash bags in the suburbs of Pittsburgh. He purchased boxes of trash bags from a friend for $3 each and sold them to his neighbors for $6. He identified a need and crafted a compelling 14-second pitch: “Hey, I’m Mark. Do you use garbage bags? I’ve got a great deal for you.” He gave out his phone number, offering to deliver more garbage bags anytime they were needed, creating what might have been the only subscription garbage bag service in the country at the time. Little did he know this was the first step on his path to building a billion-dollar empire.

At the age of 24, he moved to Dallas,Texas, and after a brief stint as a bartender, Cuban landed a job as a computer salesman at a local store. His natural sales abilities shone through, and he quickly became a top performer. However, he was fired within a year after he took a morning meeting with a potential client instead of opening the retail store. Undeterred, Cuban turned this setback into an opportunity and founded MicroSolutions, a software reselling company, in 1983.

At MicroSolutions, Cuban's sales prowess blossomed. He relentlessly pursued clients, often working 16-hour days to close deals. His tenacity paid off as MicroSolutions grew to over $30 million in revenue, scoring big deals with marquee clients like Perot Systems, one of the biggest IT companies in the U.S., founded by legendary salesman Ross Perot.

In 1990, Cuban sold MicroSolutions to CompuServe for $6 million. He netted around $2 million from the deal after taxes. However, his entrepreneurial spirit craved a bigger challenge, leading him to start exploring the burgeoning world of the internet.

In 1995, Cuban and a friend launched, an audio and video streaming service that allowed users to listen to live sports broadcasts and other events over the internet. As the company's primary salesperson, Cuban tirelessly pitched the service to potential clients, securing deals with major sports leagues and media companies, including a deal to live-stream the first ever Victoria’s Secret Fashion Show. 

Cuban's relentless sales efforts, combined with his visionary understanding of the internet's potential, transformed into a trailblazer in the streaming industry. In 1999, at the height of the dot-com boom, Yahoo! acquired for a staggering $5.7 billion, making Cuban a billionaire overnight (he claims he sat in his underwear refreshing his bank account while waiting for the money to come through). 

Throughout his journey, Mark Cuban's commitment to selling has set him apart. He embodied the qualities that every successful salesperson should strive for – perseverance, a willingness to take calculated risks, and an unshakable belief in the product or service being sold. As Mark says, “Everything goes back to sales, no matter what.” Indeed. 

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