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.