Holding the position through a charitable foundation
Does not transfer at this scaleSlim parked 77.6% of a disclosed stake in two foundations. The Canadian analogue — a private foundation or a donor-advised fund holding shares — exists, and donating private company shares can in principle eliminate tax on the accrued gain. But private foundations in Canada face excess business holdings rules that limit how much of a single corporation they may hold, CRA requires a disbursement quota, and the setup and compliance cost only makes sense at a level most founders are nowhere near. A donor-advised fund at a community foundation does the same job for a fraction of the overhead.
What not to copyThe thing worth noticing is not that he used foundations — it is that using them required disclaiming beneficial ownership of the shares. Control and tax efficiency pulled in opposite directions and he chose efficiency. That trade-off is identical at your scale and is the question to ask before any share moves into any charitable vehicle: what are you giving up the right to decide?