In Florida a trust taking title is mostly about probate and privacy. Ontario has a probate analogue — Estate Administration Tax, roughly 1.5% on estate value above $50,000 — and an inter vivos trust can sidestep it. But the Canadian trust rules cut the other way on a personal residence: the 21-year deemed disposition treats a trust as having sold its capital property every twenty-one years, and inter vivos trusts are taxed at the top marginal rate on retained income. “Put the house in a trust” is a materially worse default here than in Miami.

Where it does transfer, and sharply, is the version that fits you: a discretionary family trust holding shares of your operating company, set up alongside an estate freeze. You freeze today’s value into preferred shares you keep; future growth accrues to common shares held by the trust; and on a qualifying sale the lifetime capital gains exemption on QSBC shares ($1,275,000 for 2026, indexed — confirm the current figure) can potentially be claimed by more than one family beneficiary. That is the Ontario version of “the buyer of record is not the person,” and the whole thing only works if it is done before the value arrives. A freeze executed after the growth has happened freezes nothing worth freezing.

FIRST STEP THIS WEEK — Write down one number: your honest estimate of what Rocky Software’s shares are worth today. That is the number a freeze would lock in, and it grows every month you wait. Then book 45 minutes with a tax accountant who does owner-managed work and ask specifically whether your shares currently meet the QSBC purity tests — 90% active-business assets at the moment of sale, more than 50% throughout the preceding 24 months. Founders routinely fail this by accumulating passive cash inside the operating company and only find out when a buyer’s lawyer tells them, at which point the 24-month clock means it is too late to fix for that deal.