Solomon’s position rests on three things you do not have and cannot manufacture: compensation paid in a liquid public stock, an employer that withholds at full marginal rate on delivery, and a market that lets him convert any number of shares on any day. Your concentrated exposure is shares in a company you control, where there is no vest, no withholding event and no bid.

The honest Canadian analogue is a different question entirely. For a private-company owner the live issue is not how much do I sell but whether the shares will qualify for the lifetime capital gains exemption when you do — reported at roughly $1.275 million for 2026, indexed from the $1.25m floor, and applying only to qualified small business corporation shares. Confirm the current-year figure with your accountant; the indexation moves it.