Mark Cuban Says, Don't Invest In Rap, Restaurant And Liquor Companies. In a 2024 appearance on the “Club Shay Shay” podcast , the billionaire entrepreneur explained that many professional athletes make the same costly mistakes after signing their first big contract. If he were entering the league today as a player fighting for a roster spot, he said he would still be “living like a student” because “you don’t know how long it’s going to last. If he were earning $40 million, $50 million or $60 million a year, Cuban told NFL Hall of Famer Shannon Sharpe he would hire someone with a proven track record managing wealth. Trending: Want rental property income without fixing leaky faucets or screening tenants. Arrived lets you invest in rental homes starting at just $100 Instead, Cuban suggested keeping friends in other roles if needed, but leaving financial planning to professionals with years of experience. He also had a straightforward warning about the types of businesses athletes often r...