Better yet, he gets loans, collateralized against those unrealized gains to the current value of the gains, and then writes off the loan interest against his present and future taxes! Amazing!
Probably not. That strategy is a US strategy that takes advantage of holding the loans until death, then using the step up basis to zero out the unrealized gains and then pay off the loans.
Canada doesn't have that. At death, assets are deemed disposed, so trigger unrealized gains as taxable income on the last tax return. It often results in the estates of upper middle class people paying a lot of taxes.
But not the truly rich like Tobi who have good accountants and lawyers. He'll have moved his stock into a trust that doesn't dissolve on death.