Executive Corner
Estate Planning for Executives, Founders & Equity-Rich Professionals
Sophisticated strategies for concentrated stock, RSUs, ISOs, 10b5-1 plans, founder shares, and pre-IPO equity. The estate planning challenges that don't fit a generic playbook.
Why It's Different
Why Executives Need a Different Approach
Generic estate planning advice assumes diversified portfolios, ordinary income, and no trading restrictions. Executives face a fundamentally different set of constraints — and opportunities.
Concentrated Stock Creates Outsized Exposure
A single equity position representing 50–90% of net worth distorts every aspect of estate planning — from the size of the taxable estate to the basis step-up strategy. Diversification constraints mean estate planners must work around positions, not just through them.
SEC Trading Restrictions Constrain Timing
Section 16 officers, 10% holders, and anyone in possession of MNPI face blackout periods and short-swing profit rules that can make gifting shares at the optimal time legally impossible. Rule 10b5-1 plans must be architected with estate transfers in mind from the start.
Lock-Ups & Vesting Complicate Gifting
Transfer restrictions, vesting schedules, and post-IPO lock-up periods can make it legally impossible — or economically irrational — to gift shares that appear on paper to have low value. Planning must align with restriction expiration windows and anticipate acceleration clauses.
Each Equity Type Has Unique Tax & Gifting Rules
QSBS, RSUs, ISOs, and NQSOs each carry different income tax treatment, basis rules, and gifting implications. ISOs cannot be gifted to trusts without triggering disqualification. QSBS exemptions require careful structuring. One-size-fits-all advice causes expensive mistakes.
The $15M Permanent Exemption Changes the Calculus
The One Big Beautiful Act (OBBBA) permanently raised the federal estate tax exemption to approximately $15 million ($30M per couple). For many executives, federal estate tax exposure has diminished — but state taxes, income tax planning, and dynasty trust opportunities remain critical. The planning window is open; acting is still wise.
Coordination With Legal & Compliance Is Mandatory
Any estate transfer involving company securities requires sign-off from securities counsel, compliance officers, and often the board. Estate planning attorneys who don't understand this dynamic create plans that look good on paper but cannot be executed. The best plans are built with the entire advisory team at the table.
Guides & Resources
Executive Corner Guides
In-depth guides covering the planning strategies, legal structures, and tax considerations that matter most to executives and founders — written for sophistication, not simplification.
10b5-1 Plans for Estate Planning
How insider trading rules intersect with gifting strategies, and why your trading plan needs to account for your estate plan from the outset — not as an afterthought.
Read Guide Wealth TransferSLATs for Executives
Spousal Lifetime Access Trusts as the executive's go-to wealth transfer vehicle — what they are, when they fit, the reciprocal trust doctrine trap to avoid, and how to fund them with equity.
Read Guide Stock & EquityEstate Planning for Concentrated Stock
Strategies for executives sitting on a single stock position worth millions: exchange funds, charitable remainder trusts, hedging structures, variable prepaid forwards, and direct gifting.
Read Guide State TaxState Estate Tax 2026
Official 2026 figures for New York, Massachusetts, Illinois, Washington, and New Jersey — and why the federal $15 million exclusion does not erase state tax or create state portability.
Read GuideQSBS Stacking via Trusts
Multiplying the $10M QSBS exclusion by gifting qualified small business stock into irrevocable trusts — mechanics, limitations, and IRS scrutiny considerations.
RSU Estate Planning
How to structure estate plans around unvested RSUs — including what happens at death, income tax consequences, and trust strategies that work with your equity plan documents.
Founder Equity Pre-IPO
The narrow window to gift founder shares while their 409A value is low — GRATs, SLATs, and IDGTs funded with pre-IPO equity, and the transfer restrictions that complicate the strategy.
SPAC Sponsor Estate Planning
Founder shares, promote structures, and earnout provisions in the de-SPAC context — and why standard estate planning templates fail to account for SPAC-specific equity mechanics.
D&O Considerations
How D&O insurance policies and indemnification agreements affect estate planning — including clawback risks, indemnification obligations that survive death, and estate administration complications.
Audience
Who This Is For
Executive Corner is written for professionals whose estate planning complexity goes beyond a typical wealth management client — people with equity compensation, trading restrictions, and liquidity constraints at the center of their financial lives.
Quarterly Executive Estate Planning Briefing
Tax law updates, planning windows, and case studies — for executives and their advisors. Quarterly, no fluff. When the law changes in ways that matter to your equity comp, you'll know first.
Quarterly emails only. No spam. Unsubscribe at any time.