This is the single mechanic in this edition that maps cleanly onto a founder of a private Ontario company. Wolfe Herd is doing the public-market version of something you can do privately: exchanging a position for shares in a new holding entity instead of selling it.

The Canadian equivalents:

• Section 85 rollover — transferring shares or assets to a corporation on a tax-deferred basis in exchange for shares of that corporation.
• Section 86 or section 51 share exchange, the machinery of an estate freeze: you exchange your common shares for fixed-value preferred shares, new commons are issued to a family trust or the next generation, and all future growth accrues outside your hands at today’s value.

The timing question is the whole of the value: a freeze is worth doing before the growth, not after.

This week: pull your current share register and a rough fair market value for the company, and book a conversation with a Canadian tax accountant about whether a freeze makes sense now or after the next valuation step.