Concentrated equity, deferred compensation, and the sequencing each requires.
One employer’s stock, and the architecture composed around it.
Senior corporate leaders accumulate a balance sheet that is, by design, concentrated. Stock options, restricted units, performance shares, and deferred compensation all denominated in the equity of a single employer — granted on a calendar the executive does not control, vesting on a schedule the executive cannot accelerate, sold inside windows the executive cannot widen.
Each award, in isolation, is well-earned. The portfolio as a single position rarely is — not for lack of capability, but because the next earnings cycle is always more urgent than the review of awards already vested. The structural questions accumulate quietly until a board change, a strategic event, or a planned departure forces every one of them at once.
The work is to compose the sequencing of vest, sale, defer, diversify, and gift across years rather than around quarters — in concert with the executive’s 10b5-1 discipline, the family’s tax position, and the eventual transition out of full executive compensation.
Four reviews the next earnings cycle defers.
Each, attended to in time, is worth more than a vesting cliff.
The concentration in employer equity, sequenced down.
The mix of options, restricted units, performance shares, and deferred shares, viewed as a single position. The plan to bring concentration to a level the family is willing to hold — sequenced across years, against the company’s blackout calendar and the executive’s 10b5-1 discipline, not against a single quarterly window.
Deferred compensation, mapped against the personal balance sheet.
The deferred plan as a future cash flow with its own tax character, its own creditor risk, and its own distribution timing. Sequenced against the rest of the family’s income across the years that follow the executive role, so the plan’s payout schedule is composed deliberately rather than discovered at separation.
The 10b5-1 plan, the vesting calendar, and the tax sequencing.
The pre-arranged sale plan composed against the family’s actual liquidity needs. The exercise calendar for stock options sequenced against AMT exposure where applicable, against capital-gains treatment, and against the executive’s expected tenure. One coordinated plan rather than a sequence of unrelated transactions.
The transition out of full executive compensation.
The retirement, the next role, or the board-only chapter. The deferred-comp distribution schedule, the unvested-equity treatment, the COBRA and benefits bridge, the cash-flow architecture for the years between full compensation and full retirement. Sequenced years before the transition is announced, not negotiated under it.
The position, then the operating rhythm of the role.
Year one is the architectural review of compensation, equity, and the personal balance sheet. From there, the relationship operates on the rhythm the role permits — quarterly counsel, proactive ahead of every earnings window, every blackout, and every grant or vesting event. Existing tax counsel and corporate counsel continue under their own mandates.
For eleven years my balance sheet and my employer’s share price were the same line on a graph. The architectural review separated the two without my having to negotiate a single window. The sequencing was already on the calendar by the time the board change arrived; the tax outcome was already composed by the time it was triggered. The role kept its rhythm. The family’s position changed underneath it.
Eleven 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 Liquidity Event
Approaching, mid-sale, or year one beyond the exit.
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 generational 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.
Technology Founders & Venture Principals
Pre- and post-exit founders, operators, and fund principals.
Cross-Border Families — Canada & U.S.
Dual residency, dual citizenship, U.S.-situs assets, and the treaty work.
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.
Compose the sequencing in advance.
A career composed of grants, vests, and blackout windows deserves a sequencing composed across years rather than around quarters. Inquiries are read in confidence and answered within one business day.