The interposed vehicle
This is the week’s one genuinely scale-free mechanic. Schuurman’s CMXI B.V. and your Ontario holdco do the same structural job: the operating shares sit under an entity you control, so proceeds, voting and succession are separable from each other and from you personally. In the Canadian version a holdco lets you move surplus out of the operating company by inter-corporate dividend, hold investments corporately, and — with a family trust in the structure — give several people a claim on future growth without giving any of them your present control. That is exactly the Drew Trust pattern: beneficiary without discretion.
First step this week: write down, in one page, who holds the shares of Rocky Software today and in what proportion, and whether there is any class of share other than the one you hold. You cannot evaluate a freeze, a trust or a sale without that page, and most founders cannot produce it from memory.
The hard constraint to know before you like this too much: a Canadian family trust faces a deemed disposition on its 21st anniversary, which can trigger tax on accrued gains unless assets are rolled out to beneficiaries first. Structures built at 40 create a problem at 61. That is a planning input, not a reason to avoid it.