Billionaire Mark Cuban is no stranger to being asked, “how would you start over?” However, in a recent Wired “Tech Support” Q&A in 2023, someone posed a question that raised the stakes significantly. The challenge presented to Cuban was this: “You have six months to make as much money as possible, starting only with a phone and $500 in cash. What are you doing?”
Cuban’s response to this question was met with excitement. “That is the best question I have ever been asked in my entire adult life,” he said. Instead of opting for common strategies like flipping phones, trading crypto, or launching an app, Cuban laid out a step-by-step plan that involved finding a sales job.
“I’m going to find a sales job,” he told Wired. “Because I already know that if I’m down to my last $500, and all I have is a phone, I am going to get that job and I am going to learn more about that industry than anyone on the planet.”
True to his word, Cuban explained that he would live on commission for the first three months, focusing on becoming the top-performing salesperson in the company. Once he demonstrated his capabilities, he would leverage his success to negotiate a higher salary or venture out on his own selling the same products.
This approach reflects Cuban’s career trajectory, which was built on a foundation of sales expertise. From selling garbage bags door-to-door at the age of 12 to launching MicroSolutions out of his apartment and eventually selling Broadcast.com for $5.7 billion to Yahoo, Cuban’s success has been fueled by his ability to pitch effectively.
Even on “Shark Tank,” Cuban’s pitch has been his power. It’s not just about convincing people, but about genuinely helping them. As Cuban told GQ in 2023, “You’re not trying to convince people. You’re trying to help them.”
While not everyone may have the same affinity for sales, Cuban’s story serves as a reminder that there are multiple paths to success. Whether through sales acumen, innovative ideas, or sheer determination, individuals can carve out their own unique journey to achieving their goals.
In a world where entrepreneurship and innovation reign supreme, Cuban’s story is a testament to the power of perseverance, strategic thinking, and effective communication. Aspiring entrepreneurs can draw inspiration from Cuban’s willingness to take risks, adapt to challenges, and ultimately thrive in the competitive landscape of business.
By embracing the lessons learned from Cuban’s experiences, individuals can chart their own course towards success, armed with the knowledge that determination and drive can pave the way for endless possibilities.

