The Pale Fire mechanic — Šenkypl and Barta selling a 7.8% stake to their own holding company for $76.2M of cash — is the single most attractive-looking move on this page, and in Canada it runs straight into section 84.1 of the Income Tax Act. That provision exists specifically to stop a shareholder from extracting corporate cash as a capital gain by selling shares to a non-arm’s-length corporation; it can recharacterise the proceeds as a deemed dividend and grind the paid-up capital of what you receive.

The Czech structure does not map and the arithmetic that makes it work for them does not survive the border. There are legitimate Canadian routes to a holdco layer — a section 85 rollover, an estate freeze, a crystallisation of the exemption — but they are built the opposite way round from a cash sale, and every one of them is a planned, documented transaction, not a trade. The useful takeaway is the negative one: if a structure’s appeal is that it turns corporate cash into a personal capital gain, assume it has already been legislated against here.