Andrew Spira appeared via audiovisual link in Waverley Local Court on Friday to make an application to dismiss the charges on mental health grounds.

The 24-year-old has admitted to twice breaching conditions of an apprehended violence order taken out by police to protect his former partner.

According to the court documents, he called the woman on multiple occasions despite being prohibited from contacting her under the AVO conditions.

One of the phone calls lasted for an hour and a half.

The court was told the couple had been together for seven years and owned an impressive property portfolio together.

Property records reveal one of their homes in Sydney’s illustrious eastern suburbs recently sold for more than $10m as the pair attempt to divide their assets.

Spira is the founder of successful business loan company Pineapple Funding, which the court heard was currently earning $1m annually.

His lawyer Elias Tabchouri said his client was16 years old when he became involved in a relationship with the woman who was twice his age.

He claimed Spira had grown up in a “horrible” and “severely toxic” environment created by a father who abandoned the family after declaring bankruptcy and a mother who abused alcohol.

Spira’s mother is Lizzie Buttrose, a former Sydney socialite and niece of media mogul Ita Buttrose.

Mr Tabchouri alleged she “totally abandoned” her son, who had been assaulted and stabbed by one of her partners during his teenage years.

As a result of his “very difficult” upbringing, he said Spira had commenced an “almost motherly relationship” with a woman 16 years older than him.

“A relationship where someone is 16 years older than another clearly has a power imbalance,” he argued.

The dissolution of their relationship had been very difficult for Spira to accept when he had relied on it so heavily, his lawyer said.

The court heard the 24-year-old has been charged with assaulting his former partner a few months after they split. He has not entered pleas to the charge.

Mr Tabchouri said the relationship began to fall apart when Spira and partner began to use drugs together.

Magistrate Jacqueline Milledge noted he had a history of drug abuse dating back to his early teens.

She said the business owner had begun drinking alcohol at just 12 years old before turning to prescription and illicit drugs at age 14.

By the time he was in his 20s, he reported taking 40 tablets a day of a prescription sedative in addition to illegal drugs such as methamphetamine, cocaine, and cannabis.

“His drug use is very, very significant,” Ms Milledge said.

Mr Tabchouri said Spira had developed psychosis induced by substance abuse, which had led to his hospitalisation earlier this year.

In the throes of a separate psychotic episode, the court heard he travelled to the Northern Territory where he is now under strict bail.

The 24-year-old has been charged with making a false foreign travel document and using false identity information to obtain an air ticket.

Police allege he used a fraudulent United Kingdom passport and fake name to travel overseas out of Sydney Airport for a business deal after becoming “deluded” into thinking an airline was “out to get him”.

Just a few weeks later, he allegedly flew to Darwin on a private plane and made illegal plans to leave the country. He has not entered pleas to the charges in NSW or the NT.

Although Ms Milledge acknowledged Spira’s “complicated” and “longstanding” diagnosis of post-traumatic stress disorder, she declined to dismiss the charges under the mental health act.

“Domestic violence breaches of (AVO) orders are very serious,” she said.

“There was no violence, but … I have to look at the fact that there were previous breaches.”

The magistrate adjourned the matter until October, when Spira will face his fate over the two breaches.

Spira’s legal team, Mr Tabchouri and Samir Karnib, told NCA NewsWire they commended their client and would continue to support him.

“What’s come out today is the terrible childhood and upbringing he’s had to endure,” they said outside the courtroom.

“The fact that he was able to be so successful in his career is a credit to him and his resilience.”

Despite the unsuccessful application under the mental health act, Spira’s lawyers said they were looking forward to “completing these matters in a way that will assist his rehabilitation”.

Originally published as Troubled past of multi-millionaire laid bare