Billionaires in America have big wallets, but they also have big egos. Many have a tendency to think that success in the business world will smoothly translate into success in politics — if you climbed the ladder to the top of a Fortune 500 corporation or created a global retail chain that nets billions of dollars in revenue every year, perhaps you would think running the country would be a cakewalk too.

Ross Perot, the eccentric billionaire from Texas, ran for president as an independent twice and claimed nearly 20 million votes, more than 18.9 percent of the popular vote, in the 1992 election. Former New York City Mayor Michael Bloomberg has been flirting with a presidential candidacy for more than a decade. Tom Steyer, the California hedge fund titan, dreamed about a White House run all last year, before eventually deciding it would be better for him to focus his efforts and $40 million of his money to the impeachment of President Trump. Trump, of course, used his personal wealth and salesmanship in the real estate and celebrity worlds as proof that he could clean up Washington and throw the dead weight overboard.