Billionaire Mark Cuban has heard every version of “how would you start over?” But in a Wired “Tech Support” Q&A in 2023, someone finally raised the stakes.
“You have six months to make as much money as possible,” he said. “All you have to start with is a phone and $500 in cash. What are you doing?”
“That is the best question I have ever been asked in my entire adult life,” Cuban said. And then he gave a step-by-step answer that didn’t include flipping phones, trading crypto, or launching an app.
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“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.”
He wasn’t joking. For the first three months, Cuban said he’d live on commission — focusing on one goal: becoming the top-performing salesperson in the building. After that, he’d cash in.
“Three months in, when I’ve demonstrated that I am the best salesperson in the history of that company, I’m going to walk into my boss’ office and I’m going to tell him or her: ‘You’re either going to pay me this amount of money to keep me, or I’m going to start my own business selling this stuff,'” he said. “That is exactly what I would do.”
Cuban built his career on this mindset. Before becoming a billionaire, he sold garbage bags door-to-door at 12, launched MicroSolutions out of his apartment, and made $5.7 billion selling Broadcast.com to Yahoo. From cold calls to billion-dollar exits, his pitch has always been his power.
And on “Shark Tank,” it wasn’t the backstory or the business plan that sealed the deal — it was the pitch. Cuban told GQ in 2023, “You’re not trying to convince people. You’re trying to help them.”
Not everyone’s built for sales. And not everyone wants to talk their way to the top. That doesn’t mean they can’t still be part of the next big thing.
