Simon Cowell went through a bout of bankruptcy during the early days of his career in his late 20s. "I had started a label with about £4,000 or £5,000, and someone had backed me financially. The guy who backed me ... his company was bought by another company or something - I can't remember - and that company went bust," Cowell, 66, said during his appearance on the "How to Fail" podcast, released on Monday, January 6. "I was in debt." He continued, "I was, I mean literally, bankrupt. I owed the bank about, I think, £250,000 pounds.