The sale is not the moment that matters.
Three windows. Only one of them is the transaction.
The transaction is where the bankers and lawyers do their best work. For the family, it is the least consequential of the three windows.
The window before the sale is where the after-tax outcome is decided. Some of that work takes twenty-four months. None of it can be added in the closing month.
The window after the sale is the one most families arrive unprepared for — fresh capital, no architecture beneath it. The year that follows matters as much as the years that came before.
Four points at which the difference is made.
Each is composed in concert with the family’s existing counsel. Each, attended to in time, is worth seven figures or more in after-tax outcome.
Pre-transaction architecture, twenty-four months out.
Extending the lifetime capital gains exemption across spouse and children. Cleaning up the balance sheet so the shares qualify. Setting the share classes early enough to clear the holding periods. None of it can be added in the closing month, and the difference is most often measured in seven figures after tax.
The deal table, coordinated.
Bankers, lawyers, tax counsel, and the family convened at one table on a written cadence. Senatus holds the architecture while each specialist executes within their own mandate. Tax decisions and deal decisions arrive on the same desk, on the same day — not on separate ones.
Year one, composed for the proceeds.
Where the capital is held, and in which companies or trusts. How it is invested — written for the family rather than against a benchmark. When and how to give: where allowed, gifting shares before the sale will outperform gifting cash after. The cross-border position settled before the first reporting cycle. The architecture set for the next decade of compounding.
The estate, freshly liquid.
A balance sheet that was illiquid for fifteen years is now liquid. The estate plan written for the operating company no longer fits. Wills, trusts, powers of attorney — and a separate U.S. will if property sits there — reviewed against the new position. The work is rarely complex. It is consequential, and almost always overdue.
One mandate, held through every window.
The earlier the engagement begins, the more of the outcome is ours to shape. Whichever window we are retained on, the relationship continues into a quarterly cadence — for the years the proceeds compound.
The deal closed in March. The architecture had been composed the prior September. The first quarter after close was the calmest of the entire transaction.
Twelve adjacent audiences.
Most principals belong to more than one. The architecture is composed for the family in front of us; the descriptions below are how families most often arrive.
The Founder’s Chapter
The enterprise, the estate, and the architecture, coordinated in concert.
The Stewardship Chapter
Families two and three generations into the enterprise and the estate.
The Transition
Widowhood, divorce, inheritance, or the passage to the next generation.
Business Owners & Founders
The founder whose balance sheet lives inside the operating company.
Real Estate Developers & Principals
Entity-dense portfolios, refinancing cycles, and the passage of the book.
Medical, Dental & Allied Health
Professional corporations, retained earnings, and the practice as an asset.
Legal, Accounting & Finance
Senior professionals whose own architecture is the last to which they have time to attend.
Executives & Senior Corporate Leaders
Concentrated equity, deferred compensation, RSU cadences, and the sequencing each requires.
Technology Founders & Venture Principals
Pre- and post-exit founders, operators, and fund principals; the tax position differs at each stage.
Cross-Border Families — Canada & U.S.
Dual residency, dual citizenship, U.S.-situs assets, and the treaty work each occasions.
Women Principals & Female Heads of Household
Founders, executives, widows, and inheritors, engaged on terms of their own choosing.
Philanthropists & Family Foundations
Families for whom philanthropy has moved from line item to operating discipline.
Open the window early.
The two years before a sale are where the after-tax outcome is decided. If a transaction is in view, write to us. Inquiries are read in confidence and answered within one business day.