What the Frists did — move units of the private holding vehicle rather than the listed shares, at a formula valuation, into trusts for the next generation — does not port directly. The mean-of-high-and-low pricing is a US gift-tax convention and Canada has no gift tax; what Canada has instead is deemed disposition at fair market value on a non-arm’s-length transfer, which means a transfer that costs a US family nothing can trigger a capital gain here.

The structural idea does port, as the estate freeze: exchange your common shares in the operating company for fixed-value preferred shares, issue new commons to a family trust, and all growth from today forward accrues outside your estate. This is standard Ontario practice, not exotic. The honest caveat is that the income-splitting half of the old case for it largely died with the 2018 TOSI rules — adult family members who are not genuinely active in the business are taxed at top rates on dividends from it. A freeze today is about capital gains on an eventual exit, not about sprinkling income next year.

First step this week → Pull your current cap table and a rough FMV estimate for Rocky Software, and ask your accountant one question: does freezing at today’s valuation beat freezing later, given where you think the next three years go? The answer is entirely about your growth expectation, and the window closes as the company gets more valuable.