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Then, he landed his first job in tech as a PC software salesperson at a company called Your Business Software. But in an old blog post, which Cuban recently shared on Twitter, the billionaire revealed he almost didn't land the consequential role. The interviewers weren't impressed, Cuban wrote, until he answered one question: "What do you do if a customer has a question about a software package and you don't know the answer?" "Ding ding ding… [the interviewer] just loved the answer." Cuban didn't know it was a trick question, so he answered it honestly, stumbling into the correct answer.
Selling a company for billions of dollars didn't immediately upgrade Mark Cuban's life. "When I sold my company for billions of dollars, to go and celebrate, I was on a Southwest flight," Cuban told ABC News earlier this year. In 1999, Cuban and his Broadcast.com co-founders sold their company to Yahoo for $5.7 billion in stock. "That served me a long, long time." Buying a private jet "was my all-time goal," Cuban told Money in 2017.
Before Cuban made his fortune, he experienced what it feels like to be truly broke in his early 20s. In Cuban's experience, the biggest misconception about getting, and staying, super rich is that money automatically changes you in a big way, he told Kennedy: "Everybody thinks that money changes you. Everybody thinks that money changes you. "No matter the scale, having more money than you did when you were broke changes you some," said Cuban. Don't miss: Mark Cuban doesn't want his kids to be 'entitled jerks'—here's his parenting strategyLike this story?
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