“We get a lot of complaints about people’s inability to get stock in enough size to make a substantial holding,” White has said.

However, people close to White who requested anonymity because they were not authorised to speak publicly said the share sales had been partially paid to his former wife, Barbara Mason. White has recently remarried.

A spokeswoman for White said he was legally prevented from responding to questions about this subject. The WiseTech board declined to comment on privacy grounds.

White has continually sold WiseTech shares he held personally and via RealWise Holdings, an investment vehicle that is 92 per cent owned by White and 8 per cent owned by WiseTech co-founder Maree Isaacs, who remains on the company’s board.

Ed John, from the Australian Council of Superannuation Investors, said on Monday the allegations were a “major concern for investors”.

John said it was “critical that the board investigates these issues on behalf of all WiseTech shareholders and responds appropriately”.

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Another influential advisory firm, Institutional Shareholder Services, also said it would consider the allegations before it provided recommendations to its clients. “Private matters are private; company matters are not, and the disclosure issues by the company surrounding its executives is obviously something we will be looking at,” said head of research Vas Kolesnikoff.

“The board needs to tread carefully here – if it did not disclose company matters relevant to shareholders, then it needs to explain. The board needs to be acting in the interests of shareholders here and preserving shareholder value.”

White owned about 50 per cent of WiseTech when the company was listed on the ASX in 2016.

Williamson role in spotlight

Leaked director correspondence also revealed governance concerns over the founder’s decision to pay former chief growth officer Gail Williamson $2.7 million – double what he was earning as chief executive – without disclosing this to investors.

In her role as an investor relations adviser, Williamson is understood to have travelled extensively with White on roadshows domestically and overseas to promote the company to investors ahead of its public listing on the Australian Securities Exchange in early 2016. Before becoming chief growth officer in 2017, Williamson spent two years as general manager of investor relations and corporate affairs.

Those familiar with Williamson’s role said she acted as a gatekeeper to those wanting to speak to White, which included the media, stockbroking analysts and institutional investors.

“Gail was the gatekeeper – you couldn’t get a meeting with Richard without going through her,” said one person familiar with the company, who was unable to speak publicly for privacy reasons. “She was very close to Richard. She grew into a very senior role.”

Another described Williamson’s role “as so all-encompassing”. The source claimed Williamson was “micromanaging” the billionaire’s life.

Her pay as chief growth officer surprised recruitment executives, who estimated similar roles would pay as much as $1 million.

“My interactions with Ms Williamson have always only been business related,” White said on Sunday.

The Herald, The Age and The Australian Financial Review are not suggesting Williamson was not deserving of her remuneration, or that she was not qualified, only that the board raised this issue with White.

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In 2019, White gave an interview to the ABC’s Elysse Morgan about attacks on WiseTech by hedge fund JCapital. The interview was a trainwreck for White. During the interview, Williamson can be heard off camera several times interrupting White to correct him.

The WiseTech founder was defending the company against claims by JCapital that the tech group, which provides software to logistics companies globally, had made a series of “disastrous” acquisitions to maintain a facade of high growth and was failing to properly integrate the firms. White rejected the allegations.

Board under pressure to produce answers

The WiseTech board is reviewing a multimillion-dollar payment to a woman in a sexual relationship with White who later made allegations about inappropriate behaviour by him. The matter was settled with a multimillion-dollar payout in March 2021, with the woman agreeing to withdraw the allegations.

The board said that White, 69, had provided the previous board with a statutory declaration denying the allegations but that some directors became aware of the allegations only on Friday.

Michael Malone, a WiseTech director, said on Monday the board was reviewing the claims. “We’d like some time to consider it, and we’ll respond via [chairman] Richard Dammery.”

Salacious details about White’s private life entered the public domain in the past month. The WiseTech founder lodged a bankruptcy notice against another former lover, Sydney wellness entrepreneur Linda Rogan, who applied to the Federal Court to have it thrown out.

Billionaire’s property empire

While Monday’s disastrous plunge in the share price wiped an estimated $2 billion from White’s personal fortune, his property empire continues to grow in value.

Although White took a $2 million hit in February 2023 when he offloaded the Vaucluse “forever” home he had purchased for Rogan six months earlier, his property holdings are now worth more than $175 million.

This includes a Palm Beach trophy home he bought in 2022 for $27.5 million, warehouses in Alexandria, rural land near Nowra, and the $32 million he spent acquiring five of the 19 luxury apartments at Eliza, overlooking Hyde Park in Sydney’s Elizabeth Street.

Some of his acquisitions, including his December 2021 purchase of Eliza’s penthouse for $15.5 million, were through a company, Icarus Property Managers, fronted by two of White’s friends, including Tony Jex, the former drummer from a little-known ’70s band called Jade in which White was the guitarist. The other director, Reg Kennedy, lives in one of the six townhouses inside White’s extraordinary compound at Bexley on which White spent $7 million redeveloping.

White alternates living in the Bexley compound and the city penthouse. In September 2023, Icarus sold the penthouse to White for $1.

The extent of White’s property holdings was revealed on September 15, 2024, when White became the sole director and shareholder of a number of companies, including Icarus, previously fronted by his friends or previous employees of WiseTech.

Three of those companies White took control over had bought three different sites in Mascot for more than $85 million.

Another of the companies White recently took over, Sentry Rock, had paid $12 million for a retreat on the Hawkesbury River.

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