How “X Factor” judge Simon Cowell went from 30-year-old bankrupt to music mogul

Simon Cowell went from a broke 30-year-old living with his parents to a music mogul and TV star. He shared the story of his comeback, compared smartphones to toasters and in the latest episode of the podcast “The Diary of a CEO” revealed One Direction’s only regret.

Long before “American Idol,” “The X Factor” and “America’s Got Talent,” Cowell’s first big break was signing Sinitta to his fledgling Fanfare Records in the 1980s.

He helped make the singer’s single “So Macho” a huge hit, launching his star career.

Sinitta and Simon Cowell in London in 2006.

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“I thought everything was going to be wonderful, so I bought a house, I bought a Porsche, of course, and I had a gold credit card,” Cowell told host Steven Bartlett.

“So I’m alive, and when it all collapsed I owed the bank almost £500,000,” he added, referring to the sudden collapse of parent company Fanfare in 1989.

Cowell, who later turned Westlife and Fifth Harmony into superstars, remembers telling his bank that he didn’t care if they went bankrupt because he had no job or income – just debts.

“Yes, I was bankrupt on paper, so I went back to my mom and dad,” he said.

Simon Cowell with Fifth Harmony in Los Angeles in 2012.

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A music industry insider recalls that he once tried to drive from London’s West End to his parents’ house, but only had £5 in his pocket.

“I remember thinking that was literally all the money I had left in the world and I wasn’t sure five pounds would be enough for the taxi ride home,” he said.

Cowell avoided a sticky situation by persuading a friendly banker to lend him the money he needed to pay off his debt. A lawyer friend also helped him get a job at BMG Records, telling Cowell he could pay him back later, which he did.

Simon Cowell at the March premiere of the 19th season of “America’s Got Talent.”

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Cowell used the role to launch his own record label and host popular television talent competitions that were licensed around the world.

The talent spotter and TV judge made some other colorful comments about the podcast, which we’ve edited for length and clarity:

  • On smartphones: “I hate them so much – I think they’re boring. It’s like having a toaster with you all the time. Toast is nice, sometimes it’s nice to talk on the phone, but not all the damn time.”
  • On work ethic: “If someone comes to work at me at the age of, say, 21 and says, ‘5:30, sure, I’m off and don’t bother calling me on the weekend,’ I’ll go, ‘Well, no I’ll put money on you.”
  • About the stars: “The truth is that it’s worth it. It’s not even a price to pay, it just comes with it. It’s hard work, you will become well known and you will lose a lot of your privacy. If you want to be an accountant, you won’t have any of these problems – it just won’t be as fun.”
  • On the rights to the ‘One Direction’ name: ‘The only thing I regret is that I should have kept the name. I could have done animation or whatever. If one of the band members says they don’t want to tour, maybe that will stop the others from gigging. If I belonged to that name it wouldn’t be a problem, sometimes I can be very naive and that’s because I was very, very naive, so next time it will be part of the deal.