But when it comes to tax a court has heard he has received the sort of tax-break most Aussies can only dream of.
Symond used a tax-free $58 million windfall to build his harbourfront mansion, referred to by locals as "Westfield Point Piper".
The four-storey house was built with tax-free cash Symond received from his company between 2003 and 2006, the Supreme Court has heard.
Details of the tax-free windfall have emerged as part of a negligence lawsuit Mr Symond has taken against the law firm which advised him on his tax and company structure.
The court heard it wasn't until after the ATO audited Symond in February 2007, that Symond paid tax on the $58 million as part of a settlement of the tax dispute - in December 2007.
As part of the settlement he agreed to pay a $568,450 penalty and $5.7 million in back taxes.
Symond, who is worth an estimated $600 million, is suing his lawyers Gadens - and former partner Ross Seller - claiming the advice they gave him on June 19, 2003, that he could draw the $58 million without paying tax was negligent.
In its defence, Gadens claims Mr Symond was aware his senior finance executives and lawyers had arranged a restructure of Aussie Home Loans so he could "draw money from the new holding company tax-free".
The restructure was considered "risky" because there was a chance the ATO would prosecute him for tax avoidance.
Mr Symond argued he would never have agreed to the controversial financial structure if he had been told he was at risk of a tax audit.
In documents filed with the court, Mr Symond claimed he told his executives David Makinson and Rob Wannan: "I can't risk any problems with the ATO. The last thing I want is for the media or the public to think I'm some kind of tax cheat."
Justice Robert Beech-Jones is to hand down his decision later this year.
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