Travelers’ executives can retain zero and still be enormously long the company through unexercised options, pension and salary. You cannot diversify a private operating company by selling 4% of it. But the measurement discipline from Section 4 does carry over: the number that matters is the share of your total net worth tied to one entity, and for most founders of a private software company that figure is well above 80% without anyone ever having chosen it.

The structural lever that exists in Ontario and has no US analogue in the filings above is the lifetime capital gains exemption on QSBC shares — roughly $1.25m per individual, indexed — which requires the company to pass asset tests both over the preceding 24 months and at the moment of sale. Excess cash and passive investments accumulating inside the opco are the usual thing that quietly fails those tests years before anyone looks.