The Rollins and Jeggle structures are the billionaire version of something that genuinely scales down: ownership sits in an entity, so the entity’s balance sheet, creditors and tax attributes are distinct from yours. In Ontario with a private software company, the working equivalents are a holdco above the opco, a discretionary family trust holding the growth shares, and eventually an estate freeze that caps your value and passes future growth to the trust. The genuinely large prize is the Lifetime Capital Gains Exemption on QSBC shares — which, with a trust and the right beneficiaries, can be multiplied across family members on an eventual sale.

The catch that nobody puts in the headline: QSBC status is tested on the asset mix, and the usual disqualifier for a profitable small software company is exactly the thing success produces — cash and portfolio investments accumulating inside the opco. The 24-month test means a company that fails today cannot be fixed on the eve of a sale.