Happened to a friend of a friend who bought his vested and super-cheap options when leaving the company, while it was still private. This was in Canada, but the

Happened to a friend of a friend who bought his vested and super-cheap options when leaving the company, while it was still private. This was in Canada, but the IRS wanted capital gain tax to be paid right away. And the cap gain was in millions, because of the current company valuation. I think he lawyered up and somehow found a way to defer the payment until the company went public. So it wasn't devastating per se, but still very unpleasant. From being an almost millionaire to a real chance of being bankrupt in a matter of days.