In one corner is Nick Candy, the flamboyant property mogul married to Holly Valance, the singer and former Neighbours actress. In the other is Robert Bonnier, one of the most notorious casualties of the dotcom era, who decades later is still trying to make a name for himself as a technology entrepreneur. In the middle is Aaqua, Bonnier’s social media company that once aspired to be as big as Facebook.

Aaqua’s swift collapse, after less than two years, has left a trail of angry investors, including Candy, in its wake. It is the latest in a long history of acrimonious brushes between Bonnier, investors, employees, the taxman and financial watchdogs.

Bonnier, 54, is being sued by Candy, 51, over claims that the real estate investor was misled into backing Aaqua, including by a claim that Apple and other big global companies were also planning to put in money. Candy swapped a stake that he owned in Audioboom, the podcast business, for a stake in Aaqua.

Bonnier has denied the allegations, asserting in a new court filing that he had two face-to-face meetings with Apple leaders in 1999, as well as with other global business leaders.

The document is in response to questions from Candy Ventures, the businessman’s eponymous investment portfolio, with which Bonnier spoke in order to “test the Aaqua business thesis”.

Bonnier said there had been two Apple meetings in 1999. Tim Cook, Apple’s chief executive, had attended ten minutes of a get-together that had lasted three quarters of an hour, he said, while he claimed also to have met Steve Jobs, the Apple founder and one of the most famous names in technology, for an hour and a half. Aaqua was founded more than two decades later.

The introduction was said to have been brokered by “the late Thomas Lawerence who was Mr Bonnier’s most important mentor and introduced him to all the key players in Seattle and Silicon Valley”, according to the document. The subjects of the meeting included the “rapid development of the digital landscape”, “the importance of safeguarding safety, integrity and brand value” and “how old media would converge to new media and who ultimately would become the power centre”, the filing said.

• Aaqua boss Robert Bonnier sued by HMRC for unpaid tax

Bonnier did not comment when invited to explain the link between the purported meetings and Aaqua.

A spokeswoman for Bonnier said she could not comment on continuing legal proceedings, but added: “Candy Ventures has been ordered to pay indemnity costs and the damages of a wrongly granted worldwide freezing order [during the dispute].”

Bonnier also claims to have spoken about his concept for Aaqua to Bernard Arnault, the chief executive of LVMH, the luxury goods behemoth, and his family members. Bonnier claimed they had met on several social occasions, including at the opening of the first Dior store in Jakarta, Indonesia, when Bonnier set out his vision for the future of the internet, bringing together brands and communities and explaining “how the economic spoils could be shared”.

The filings report “the typical response from the individuals [at LVMH] was that this was awesome and exactly what the world requires” and they asked “how they could become part of it”.

Apple and LVMH were approached for comment.

Bonnier, a former UBS banker, made a name for himself as the chief executive of Scoot, an online directory valued at more than £2.5 billion during the dotcom boom of the late 1990s. His stake in the business was worth about £130 million before his star, and that of the business, fell early in the new millennium. Scoot’s main business was sold to BT in 2002 after it ran out of cash. He was then fined £290,000 by the City regulator in 2004 for misleading the stock market over his interest in Regus, the office services group.

Launched in 2021, Aaqua claimed it would be “a refreshingly new social experience” that would start online communities based around people’s interests, such as sport, with members getting a share of revenue generated by advertising. The company claimed it had raised $80 million in external investment. It employed 205 staff, most of them in Singapore, where the company was based.