Chrisley made the majority of his fortune in real estate. The reality star previously owned an investment firm, Chrisley Asset Management, which expedited "the loss recovery and liquidation of non-performing commercial and residential assets," according to Crunchbase, which notes it was founded in 2002 but folded in 2008 following the collapse of the property market. Just a couple years before Chrisley Knows Best premiered, the businessman filed for bankruptcy after amassing close to $50 million in debt (via Forbes).

"He guaranteed a real estate development loan and it failed," his attorney, Robert Furr, told People at the time. "He was on the hook for $30 million. If he hadn't had that happen, he would have been fine, financially." As Distractify notes, there were plans to open a department store called Chrisley & Co. in Atlanta, but they crumbled in the face of the family's mounting debts. As a result, they were forced to curb their extravagant lifestyle.