Nobody pays a marginal rate > 50% in Canada. However, this will be counted as a capital gain, since Match almost certainly bought his shares in the company. Tha

Nobody pays a marginal rate > 50% in Canada. However, this will be counted as a capital gain, since Match almost certainly bought his shares in the company. That means 50% of the proceeds will be added to his taxable income. He'll pay around 25% of his total proceeds in tax. His employees probably owned ~10% of the company, so let's say he sold his shares for $500M. He probably walked away with around $375M after tax.