Ah well, that means his effective tax is 49.3% (T + C becomes...

Ah well, that means his effective tax is 49.3% (T + C becomes A$747,594) and to pay for this he has to sell 4,983,960 shares, so after all this he ends up with only US$158,544 cash + 769,947 additional shares, with a final total of 8m shares. Hardly seems like much of a sell down to me.

He should have progressively exercised the options in smaller amounts over several years to keep the tax level below 37% and moved out of California to Alaska, Tennessee, New Hampshire, Wyoming or Florida. Alternatively, he should have put them in the name of an off-shore vehicle in for example, the Caymen Islands (or even a company incorporated in Australia), and exercised them through that incorporated vehicle, me thinks.