You have no public stock and no Rule 10b5-1 plan to adopt, so the literal mechanic is unavailable. What transfers is the discipline underneath it: pre-committing to a schedule so the decision is not made in the moment. Colgrove’s January plan is why his October selling carries no information — and that is the feature, not a side effect.

The private-company version is a written policy for moving retained earnings out of the operating company, agreed in advance rather than decided each quarter. The structures to ask about:

• A holdco receiving tax-free inter-corporate dividends from the opco.
• The Lifetime Capital Gains Exemption on qualified small business corporation shares — this one has asset tests that often require purification two years ahead of a sale, which makes it a start-now item rather than a later item.
• Corporate-class investing inside the holdco, and a family trust to multiply the LCGE across family members.
• The unglamorous ones that actually compound: RRSP and TFSA room, and the salary-versus-dividend mix.