If the entity's real job is control, continuity and centralised timing rather than tax magic, then the useful question is not "how do I avoid tax like they do" but "is my structure in place before the value arrives." The billionaire version is a trust holding shares acquired in 2006. Your version is a holding company between you and your operating company, and potentially a family trust, arranged while your shares are still worth comparatively little.

The deadline matters more than the structure. Canada's lifetime capital gains exemption on qualified small business corporation shares is lost on technicalities: an asset test at the moment of sale, a 24-month holding test, and an asset test across those preceding 24 months. Excess cash and passive assets in the operating company can disqualify shares that would otherwise qualify, and purification takes two years you will not have once a buyer is at the table. A family trust capable of multiplying the exemption has to exist years before a sale, not months.