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A $500k tax debt & Meghan’s “favour”: The curious case of Jackie O’s bestie

Days after announcing she was set to interview Meghan, Duchess of Sussex, Gemma O’Neill is making headlines

On March 11, media executive Gemma O’Neill – the talent manager and “bestie” of Kyle and Jackie O Show star Jackie O – declared on the Her Best Life podcast that it had been a “big week”.

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“If you’re listening in Australia, you’ll probably understand what I’m referring to there and it is to do with my bestie, Jackie,” she told her listeners.

“I’m not going to talk about that at all because it’s Jackie’s story to tell – it’s not my story to tell,” she added.

Of course, Gemma’s words were carefully chosen – a reaction to the fascinating furore surrounding Jackie’s future at radio network ARN.

The radio host’s contract was “terminated” by the radio network after Jackie gave notice that she “cannot continue to work” with her co-presenter Kyle Sandilands.

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As Jackie later made clear, the matter is now being addressed through legal channels, so it’s no surprise that her bestie wasn’t keen to weigh in.

Fast-forward a mere six days, however, and it seems that Gemma is embroiled in a story of her own – one that has piqued the curiosity of those following the Kyle and Jackie O saga from the start.

Gemma O'Neill and Jackie O at the Marie Claire Women Of The Year Awards 2024.
Gemma and Jackie O at the Marie Claire Women Of The Year Awards 2024. (Credit: Getty)

For on the very day that Jackie O was having her on-air spat with Kyle Sandilands, it has emerged that Gemma – whose talent agency Gemmie Agency has collapsed reportedly owing $543,548 to the ATO – reportedly wrote to administrators informing them that she couldn’t repay the company debts because she has no available personal savings, limited income and had not been able to refinance her Sydney apartment.

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Documents available publicly on ASIC confirm that the company formerly known as Gemmie Agency Pty Ltd, went into liquidation on 25 November 2025.

News.com.au reported that a statutory creditors’ report filed by administrators Grant Thornton Australia (GTA) on February 24 2026 revealed that the debts incurred by the agency came in contrast to a seven-figure commission paid to the agency by one “key client” between October 2023 and March 2024.

The twist comes just days after it was revealed, with much fanfare, that Meghan Markle will appear in conversation with Gemma at a three-day Her Best Life Retreat held at Coogee’s ritzy InterContinental Hotel in April.

The $3000-a-ticket schmoozing session was organised by Besties Australia Pty Ltd – a different company – one co-founded by Jackie and Gemma and registered by Gemma, who serves as director/secretary, in October 2022.

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The event was spruiked as an opportunity for “powerful conversations, relaxation, laughter and unforgettable experiences” and Meghan’s appearance created something of a stir – not least because Gemma previously said the Duchess was headlining the event as a “favour”.

“I’m going to answer probably something that I think would feel fairly obvious, ‘Oh it must be costing you a fortune to have Meghan come to your event’,” Gemma said as she announced the duchess’ participation on March 11.

“Um, no guys, I think you all know, the community knows, I don’t have that kind of money guys. That’s not on the cards for me.

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“But what I will say is that she is effectively doing this as a favour to our mutual friend.”

Gemma O'Neill
While Jackie has stepped away from the Besties brand, Gemma is set to interview Meghan. (Credit: Instagram/herbestlifepod)

Those seeking one of the 300 tickets were instructed to “register your interest for a ticket at herbestlife.org” and in order to receive an “early access code” customers needed to be subscribed to the Her Best Life mailing list.

However, some would-be attendees of the event told Woman’s Day that they never received a code despite signing up for the newsletter – sparking questions about how the tickets were allocated. 

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“Just registered but couldn’t find the VIP code anywhere,” one frustrated shopper shared on the Her Best Life Pod Instagram page.

“Hey lovely, the early access code was sent to those listeners on our mailing list! If you’re not already subscribed to that, join at www.herbestlife.org,” came the reply from Her Best Life.

“I have subscribed but didn’t get the code word?” another commented. “I’m desperate to attend this event. My life is so full on and traumatic and I would do anything to have a weekend where I can focus on me.”

“Joined but no code given,” another added.

Woman’s Day understands that the code was delivered to current listeners of Her Best Life podcast through a mailing list.  

If you were not on that list, there was no way to get a code.  However, it’s understood that getting a code did not enhance ticket chances and many people who received tickets to the Her Best Life Retreat did not receive a code.

An update on the Her Best Life web page now states: “This intimate weekend is limited to just 300 people. Ticket allocation now exhausted. Register to be on the standby list if any more become available.”

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