The Five Chapters
A taxonomy written in practitioner voice.
Each chapter below names a discipline, states its thesis, and unpacks the structural questions our senior strategists field in the first ninety minutes of a private engagement. The order is deliberate: trust architecture comes first because almost every subsequent decision depends on it.
I.
Trust & Estate Architecture
The drafting of revocable, irrevocable, and dynasty trusts is the substrate of every Penhallow engagement. We design structures that survive three generations of family governance — SLATs, dynasty trusts, ILITs, and grantor-retained annuity trusts engineered to compress transfer-tax exposure without surrendering administrative flexibility. Our senior attorneys hold four admissions to the U.S. Tax Court bar; our tax analysts model each structure under at least three interest-rate and appreciation scenarios before a single document is circulated for signature.
For families with multi-jurisdictional footprints, we coordinate situs selection across Delaware, Nevada, South Dakota, and Wyoming — choosing the governing law, the trust situs, and the trustee venue to optimize perpetuity, asset protection, and decanting flexibility as a single, internally consistent architecture rather than a stack of separate instruments.
II.
Business Succession & Continuity
Where a family enterprise sits at the center of the estate — operating companies, professional practices, real-estate holdings — succession planning is not a side engagement; it is the estate plan. Penhallow designs the intersection of buy-sell agreements, entity restructuring, GRATs, and intrafamily transfers so that a transition from founder to next generation does not trigger a liquidity event the family cannot absorb. We work alongside existing counsel and the company's CFO to model freeze, liquidation, and installment-sale pathways against the family's stated income needs and philanthropic intent.
Continuity also means governance. We draft family constitutions, shareholder agreements, and board protocols that give the next generation a formal seat at the table — and a formal obligation to it — long before the founder's interest transfers.
III.
Charitable & Philanthropic Structures
For families whose philanthropic intent is both meaningful and material, we structure charitable remainder trusts, lead trusts, private foundations, and donor-advised funds in concert with the estate plan itself — so that a gift to charity is not an after-thought deduction but a structural pillar. Our team coordinates with the family's existing foundation staff (or stands one up, where appropriate) to align mission, governance, and grantmaking cadence with the broader transfer-tax strategy.
Where multiple generations hold divergent charitable priorities, we design structures that allow each branch to express its intent without fracturing the underlying vehicle — preserving the family's voice across decades rather than decades.
IV.
Pre-Liquidity & Concentrated-Position Planning
A founder's net worth is often a single equity grant. We design the architecture that surrounds it — diversification trusts, exchange funds, and pre-IPO structures — so that a planned liquidity event produces a controllable, taxable outcome rather than an estate-planning emergency. Our strategists coordinate with the company's pre-IPO counsel, the underwriter, and the family's existing tax advisor in a single timeline so that 10b5-1 plans, QSBS eligibility, and trust funding are sequenced rather than improvised.
For families holding concentrated public or private positions, we model the post-liquidity portfolio inside a trust or family entity from day one — answering the question every sophisticated principal eventually asks: what does the balance sheet look like the morning after the event?
V.
Multi-Jurisdictional Compliance & Cross-Border Structures
Our clients live and hold assets in more than one place at a time. We design and administer estates that span 38 U.S. states and coordinate with foreign counsel in the United Kingdom, Switzerland, Canada, and Singapore where U.S. clients hold secondary residences, foreign trusts, or non-citizen spouses. Our compliance work covers trust registration, CRS and FATCA reporting, and the coordination of U.S. estate-tax returns with foreign inheritance and gift regimes.
For families with non-citizen spouses, we structure Qualified Domestic Trusts and treaty-based plans that preserve the unlimited marital deduction without sacrificing the flexibility of a properly drafted bypass structure. Read more on the framework we apply to every engagement — the 7-Layer Dynasty Audit™.