A short read, from the bench, on the questions now before our files.
Two notes from this quarter. The first, on the Income Tax Act and where its administration has shifted in 2026. The second, on the windows that open and close around a founder’s liquidity event.
The Income Tax Act itself has not changed in dramatic ways since the spring. The change has been in the posture of the agency that administers it. Three places, in particular, are now demanding a closer look from the families we serve.
What follows is the shorter version of the conversation tax counsel on this bench is now having across each file.
The inclusion-rate question has been deferred. It has not been settled.
The proposed change to the rate at which capital gains are brought into income was, after considerable noise, deferred. It has not been withdrawn, and it has not been replaced with a settled position. Families who were preparing to act on the higher rate have, for the moment, an extension. They do not have a reprieve.
The risk is not the rate itself, in either direction. The risk is the volatility of the rate, and the cost of restructuring a corporate or trust holding twice in a single decade because the assumption underneath it kept changing.
The architecture this question requires is not a bet on which way the rate will land. It is a structure that holds value efficiently under either — and that can be brought to a realization event without three months of emergency planning.
The 2024 changes to the alternative minimum tax are biting families who give meaningfully.
The alternative minimum tax was rewritten in 2024. The rewrite was not announced as a change to charitable giving. In practice, that is one of the places it has been felt most plainly. Families who were accustomed to giving appreciated public securities to a foundation or donor-advised fund, with the expectation that the gift would offset the gain, are now finding the result less neutral than the assumption.
The arithmetic is not unworkable. It is, however, no longer one a family can assume without running. The cost of an unrun calculation can be, on a meaningful gift, six or seven figures of unexpected federal tax.
The architecture this requires is a coordinated giving plan that is calculated before the gift is made — not reconciled afterward.
The expanded reporting regime has created a parallel disclosure infrastructure.
The expansion of trust and entity reporting obligations — including the bare-trust filings that were initially deferred and are now in force — has produced a set of disclosure requirements many families do not yet realize apply to them. The arrangements that meet the expanded definition are often arrangements struck decades ago, for reasons that had nothing to do with reporting.
The penalties for non-disclosure are not modest. The remedy is not complicated. It is, however, an inventory exercise, and an inventory exercise is not the kind of work that volunteers itself in a busy quarter.
The architecture this requires is a periodic structural review across every entity and arrangement on the family’s file — on the firm’s initiative, not the family’s. The posture is preventative.
Most founders we meet have an instinct for the timing of a transaction. The instinct is rarely wrong about whether the moment is approaching. It is, almost always, wrong about how much can be done about it once it arrives.
A note for founders and operating principals approaching, or considering, a transaction in the next twenty-four months — on what must already be in place to capture the value, and on the windows that, once closed, are difficult to reopen.
The market does not give notice.
The valuation a sector commands today is rarely the valuation it commanded eighteen months ago, or the one it will command eighteen months from now. Sector multiples shift. The interest-rate environment shifts. The composition of buyers — strategic, private equity, family office — shifts. The window in which a particular business will fetch a particular multiple is, almost always, narrower than the founder anticipates.
The architecture this requires is a structure that is ready before the window opens, not assembled after it does. Founders who begin restructuring during a live process have, with rare exceptions, already given up the cleanest path through it.
Most pre-sale planning needs eighteen to twenty-four months.
The instruments available to a Canadian founder before a transaction — the cleanup of the operating company so that the shares qualify for preferential treatment, the use of family trusts and holding companies to multiply the available exemptions, the freeze structures that lock today’s value into the founding generation and let future growth accrue elsewhere — all take time to implement properly.
The difference between a transaction that has been planned for two years and one that has been planned for two months is, on a meaningful exit, often eight figures of after-tax proceeds.
The architecture this requires is engagement of senior counsel before there is a deal — ideally before there is a buyer.
What you keep is not what is on the wire.
The wire transfer that closes a transaction is, for most founders, the most consequential single moment in their financial life. It is also, almost universally, not the moment they have spent the most time preparing for. The years before the transaction are spent on the business. The hours before the transaction are spent on the deal mechanics. The years after are spent learning, often slowly, what wealth means once the vehicle that built it is no longer present each morning.
The structural questions of the after — how the proceeds are held, in which entities, on what investment posture, with what governance, with what relationship to the next generation — cannot be answered well in the weeks following the close. They have to be answered before, in the same conversation as the deal itself.
The architecture this requires is a counsel relationship that holds both sides of the transaction in mind at once. The transaction is the moment. The decade after is the mandate.
Reach out.
A first conversation, in confidence, with the principal who would carry the work.