But despite her incredible aptitude for business and on-air talent, Jackie has said that her financial success in these fields has left her ashamed.
"I do sometimes get embarrassed to talk about money. I hate showing off wealth. I've always been like that...I want a nice bag, car, and house, but I don't want to flaunt it," the radio host shared candidly.
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"But [at the same time] I shouldn't be embarrassed about it, so I am trying to take more ownership of that."
"As a man, they'd absolutely be owning that, and as a female, when you're single, it's quite scary to earn a lot of money, because a lot of men can be intimidated by that.
"And so your instinct is to downplay it for that reason."
In direct comparison, co-host Kyle Sandilands regularly flaunts his wealth, from the one million he spent on his wedding, to the half a million he spent on his honeymoon to the 25,000 he spent on his son Otto's first birthday celebrations.
Earlier this year, Jackie purchased a $13.5 million beachfront mansion in the affluent Sydney suburb Clovelly.
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"I am so grateful for it, I am, but sometimes I think...I wish I was just back in my 20s and trying to buy my first apartment," she also told Stellar.
"Isn't that weird? It's only a thought I had a couple of weeks ago...I don't know. I keep asking myself why I'm thinking that way."
"All I'll say is, as women, we just need to be proud a little more."