Route A
Open window, with pre-clearance
Trade only while your company’s window is open and the general counsel’s office has cleared it in advance.
Executive wealth briefings
Concentration, liquidity and planning briefings for leaders who already run complex businesses. Plain language, stated assumptions, and models that run in your browser: nothing you type into them leaves it.
Read the briefing. Run the model. Then send a brief to the desk and meet a licensed advisor whose practice is executive wealth management.
Illustrative. Weeks 12–13 before a quarter ends and weeks 1–4 after it are shaded as a typical blackout. Your company’s insider trading policy sets the real dates.
Read or run a model
Start with a briefing or a model to frame your question.
Answer a few questions
Four short steps: where you are, your finances (ranges are fine), your goals, how to reach you.
Brief, then confirm
The desk confirms the details with you directly, then introduces a licensed advisor whose practice is executive wealth management.
Find an advisor
Equity compensation, deferred pay, change-in-control terms and board duties all interact. A licensed advisor whose practice is executive wealth management can bring them into one plan. Send a brief on your position and the desk will confirm the details with you before any introduction.
Areas advisors help with
Concentration feels like conviction until a share-price drop lands on the whole balance sheet. The glide-path model below shows what a drop costs today and at your target.
Try the modelManaging Concentrated Stock Position Risk Without Signaling
It is usually an unsecured promise from your employer. The haircut model prices that risk in, so the balance on paper stops being the number you plan around.
Price the riskDeferred Compensation Plans: Weighing the Real Tradeoffs
Severance and accelerated equity can cross a line where a 20% excise tax switches on. The cliff model shows where the line sits and what happens either side of it.
See the cliffGolden Parachute and Severance Tax Planning for Departing Executives
Reducing a position takes trading windows, and windows are finite. Set today’s share, a target and the number of windows you can use, then stress the share price.
Sold per window
4.4% of net worth
Stress hit today
-19% of net worth
Stress hit at target
-7% of net worth
Simplified: prices stay flat between windows, proceeds are reinvested outside the stock, and taxes and trading costs are ignored. A 10b5-1 plan or your company’s policy may change how and when you can sell.
Want an advisor to pressure-test these numbers?
The desk can introduce a licensed advisor whose practice is executive wealth management.
Two more models: deferred compensation and the change-in-control cliff →
20 briefings across 4 areas. Each is written to be read in a single sitting.
RSUs, options and ESPPs; AMT exposure from ISO exercises; and timing vesting around mergers, secondaries and IPO lockups.
Three instruments, three different tax mechanics, three different risk profiles. Treating them as interchangeable 'equity comp' is the first mistake most executives make.
Exercising incentive stock options can trigger a tax bill on paper gains you have not actually realized in cash. The alternative minimum tax is where that happens.
A merger, secondary offering, or IPO lockup expiration can collide with your normal vesting calendar in ways that concentrate both tax liability and market risk into a single quarter.
10b5-1 trading plans, deferred compensation elections, board compensation tax treatment, and charitable structures such as donor-advised funds.
A properly adopted 10b5-1 plan is one of the few legal ways insiders can trade during a blackout. Adopting one at the wrong moment defeats its own purpose.
Deferring income to a lower future tax bracket sounds simple. In practice, an unsecured promise from your employer carries a risk most executives underprice.
Cash retainers, equity grants, and committee fees for board service are taxed differently than most directors assume — and the self-employment tax question surprises people every year.
Donor-advised funds and charitable trusts get pitched as tax hacks. They are actually structural decisions about control, timing, and irrevocability worth understanding on their own terms.
Concentrated stock positions, change-in-control severance and excise-tax exposure, and disability and key-person insurance.
Executives face a real conflict: reducing concentration is prudent risk management, but selling company stock can be read by the market as a lack of confidence.
A change-in-control severance package that looks generous on paper can trigger an excise tax that quietly claws back a meaningful share of it.
One protects your household income. The other protects the company's balance sheet. Executives who only think about one leave a real gap in the other.
The California rules that sit beside an executive package: residency and remote-work tax, community property, Prop 13 and inherited property, 1031 exchanges, disability and SDI, public pensions, banking, first-home help and small-business tax.
California runs one of the only state-mandated short-term disability programs in the country, and it works nothing like private long-term disability coverage. Understanding the difference — and the gap between them — matters for every California worker.
SDI benefits are largely tax-free, but the retirement-savings side effects of a leave are easy to miss until a 401(k) statement shows a gap that never got made up.
California's community property system shapes both divorce settlements and a lesser-known estate-planning advantage: the double step-up in basis available to married couples.
California doesn't use a simple day-count test for residency. Remote workers who move but keep meaningful ties to the state risk being taxed as full residents long after they thought they'd left.
Proposition 13 caps how fast a property's taxable value can grow — but that cap resets when ownership changes, which is exactly what makes inherited property a distinct reassessment question.
Federal 1031 rules let real estate investors defer capital gains tax through a like-kind exchange — but California adds a clawback that keeps tracking deferred in-state gains even after the replacement property, or the owner, leaves the state.
Credit unions and banks both offer federally insured deposits, but their ownership structures create real, practical differences in rates, fees, and eligibility that are worth understanding before choosing where to keep savings.
CalHFA's assistance programs use two very different structures — deferred silent-second loans and shared-appreciation loans — and understanding which one you're signing up for matters as much as qualifying in the first place.
Both are defined-benefit pension systems built around a formula rather than an account balance — and a 2025 federal law repealing WEP and GPO just changed the Social Security picture for many members.
California layers its own franchise tax on top of federal small-business taxation, and entity choice, retirement plan design, and estimated tax discipline all carry real, California-specific consequences.
A simplified map of the three positions an insider can be in. Your company’s insider trading policy, and its counsel, decide the details.
You want to reduce a position.
Route A
Trade only while your company’s window is open and the general counsel’s office has cleared it in advance.
Route B
A written plan adopted while you are not aware of material nonpublic information, with a cooling-off period before the first trade. When you adopt it matters.
Stop
Do not trade and do not tip. Speak to counsel before anything else.
Read: 10b5-1 Trading Plans Explained: Structure, Timing, and Common Missteps →
Ready when you are
A short brief, a call from the desk, then an introduction to a licensed advisor whose practice is executive wealth management.