Macquarie used these options to acquire Nuix shares and boost its stake in the company to about 50 per cent. Standen told the court that any conditions over the options had been removed.

Nuix was the highest profile float of 2020 with Macquarie cashing in $575 million worth of shares as part of the sale and retained a 30 per cent stake in the business. Standen left the Nuix board just before its float.

Sheehy is arguing in the Federal Court that a 2008 agreement relating to his options in the business, and a subsequent splitting of each of Nuix’s shares into 50 shares in 2017, entitled him to 50 shares for each of his 453,273 options that remained after the Macquarie sale. He told the company in November 2020, shortly before the initial public offering (IPO) in December, that he wanted to exercise his options.

The company says he is entitled to one share per option, and that the dispute has already been resolved by the settlement of an earlier NSW Supreme Court dispute. There is also a legal question about whether a public float amounted to a “sale of the business” that triggered a right to exercise the options.

Sheehy argues he has suffered a loss of between $96.9 million and $182.4 million depending at which point he could have sold these shares. He appeared in the Federal Court witness box in Sydney on Tuesday and told the court his understanding was that “I was going to get 22 million shares” in the data analytics software company.