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He doesn't get to "keep every penny". There is such a thing as personal income tax, and in Canada is going to be over 50%.

Hopefully, the deal was structured with some stock, or paid to a corporate entity. Because if he received a cheque made out for $575M, most of that money went to tax. If it was made out to his personal corporation, he'd just have to pay corporate tax on it, which is about half as much. But would still be over $100M.

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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.

This would count as capital gains, so (33% federal + 14.7% provincial) / 2 would be closer to 23.85%.

That's not counting the portions that fall under lower tax rates, or the lifetime capital gains exemption of $750,000.

If he did structure it under a holding company, he could better spread out the payments over a number of years so that more of it could fall under lower tax rates.

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