Three simple words that made Kyle Sandilands $100 million

While many people turn to self-help books, motivational speakers and inspiring life mantras to follow in their quests for success, Kyle Sandilands’ journey from homeless teenager to building a business empire worth $100 million isn’t quite as easy to replicate. Speaking on a recent episode of The Game Changers podcast, The Kyle and Jackie O Show’s first-ever executive producer, Paul Dowsley, revealed what he believes is the surprising secret to Kyle’s ongoing success.

Paul shared how he was part of the team that took Kyle and Jackie O from a relatively safe and family-friendly night show to landing a primetime Sydney breakfast slot in 2005. He explained how he believes the pair quickly went to number one thanks to Kyle repeatedly saying three words to his new bosses at 2DayFM: "I don’t care."

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Kyle Sandilands' secret to success

Paul and Craig Bruce, who was Kyle and Jackie O’s Content Director at the time, then detailed several incidents where the shock jock ripped up the rules of commercial radio that every other breakfast show abided by back then. Some of these rules include keeping all breaks to a tight three minutes, so the news and traffic are then reported on time.

Craig recalls Kyle telling him off-air after some live chats would go for up to 20 minutes, "I’m not looking at the clock when the [live segment] is happening, mate. I’m trying to stay in the moment. If the content is going well, I don’t care how long the news runs late by. It doesn’t matter to me."

The former content director continued: "I had all of these paradigms which were locked in place and how a show should sound, and what a breakfast show should do – and Kyle just challenged and stomped on every single one of those. I remember talking to him about the practicalities of the traffic being 20 minutes late and we’d say a motorway is blocked then by the time we air that, it’s not [blocked anymore].

"Kyle didn’t care.'I don’t care, that’s somebody else’s problem', he’d say. 'I don’t care'."

Paul, who is now a Channel Seven reporter, went on to detail how Kyle continued to rebel against the bosses by doing things such as bringing a prostitute into the studio for a live interview after meeting her at a petrol station on his way to work, or refusing to discuss the Australian Open as he has "no interest in sport" – despite the rest of the country talking about the tennis.

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The pair agreed that Kyle’s refusal to follow most rules and constantly saying "I don’t care" when bosses attempted to tame him, is what ultimately led to his success.

Since then, Kyle has used his radio earnings to build King Kyle, a business empire worth $100 million – which includes multiple drinks companies, a record label and a multi-state property portfolio. In 2023, the shock jock and co-host Jackie O went on to sign the biggest media deal in Australian history – which will see them both earn $10 million a year each over the next 10 years.

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