They were born rich, they'll die rich. Their parents paid their way through to good grades in college. Musk bought an already established company and then retroactively called himself a "founder" of that company. His seed money came from apartheid South African emerald mines, slave labor. Trump is a "real estate mogul," which requires no skills whatsoever except having enough money to fail multiple times with poor investments, which he did. He literally would've been more successful by simply sticking the money his dad gave him in a savings account and letting it accrue interest.
Even playing "undercover boss" for a day would be too much for either of them, especially in a menial job like cashiering at McDonald's or cleaning toilets as a janitor.