A summary of facts released to media outlines Win's offending – a sole trader operating under the name Win Building.
Between November 2017 and September 2019, Win employed eight workers and deducted PAYE from their wages and filed PAYE returns with the Commissioner of the Inland Revenue, accounting for the deductions from employees' wages.
But for each month within that period except the months May and July 2018, Win did not pay the deducted amounts to the IRD by the due date.
The amount of the assessed PAYE deductions not paid by the due date totalled $226,763.26. Late payments amounting to $49,958.86 have reduced the assessed amount to $176,804.40.
"Analysis of the Win Building bank account showed that on 19 occasions there were funds available to pay the PAYE by the relevant due date, or at least make a part payment. However, those funds were instead used for other purposes such as personal expenditure."
Win was also found to have not paid $133,084.64 in GST and $18,951.79.
It amounted to $328,840.83 in unpaid taxes.
Analysis of his bank accounts found that Win used the Win Building account for "significant personal expenditure over the tax periods in question".
"Examples of the expenditure include Uber and Uber Eats, debt recovery services, cash withdrawals, drawings and overseas transactions in the USA, Mexico, and Australia totalling $224,942.23," the summary of facts says.
Win was adjudicated bankrupt on August 20, 2020 and there is "no prospect" of the PAYE, GST or income tax debts now being paid.
The maximum penalty on each charge laid under the Tax Administration Act 1994 is five years imprisonment and/or a $50,000 fine.