Averaging down into your own employer’s stock is not a lesson for someone whose single largest asset is already 100% concentrated in one private Ontario company. If anything the inference runs the other way.

The portable detail is one row of his Form 4: 98.9% of his shares sit in a family trust, 1.1% in his own name. For a Canadian founder the equivalent question — are the shares held personally, or by a holdco, or by a family trust — determines LCGE multiplication across family members, creditor exposure, and what happens at succession. And like the freeze, it is a decision that must be made before the value is there, not after.