Coverage
Four areas, twenty briefings, one standard: state the assumptions.
Coverage stays narrow on purpose. Each area below lists the briefings currently published and, where there is one, the model that pairs with it.
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Equity events
RSUs, options and ESPPs; AMT exposure from ISO exercises; and timing vesting around mergers, secondaries and IPO lockups.
- Equity Compensation Basics: RSUs, Stock Options, and ESPPs for Executives
Three instruments, three different tax mechanics, three different risk profiles. Treating them as interchangeable 'equity comp' is the first mistake most executives make.
- AMT Exposure From ISO Exercises: What Executives Need to Model
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.
- Timing Equity Vesting Around Liquidity Events
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.
Liquidity & tax coordination
10b5-1 trading plans, deferred compensation elections, board compensation tax treatment, and charitable structures such as donor-advised funds.
- 10b5-1 Trading Plans Explained: Structure, Timing, and Common Missteps
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.
- Deferred Compensation Plans: Weighing the Real Tradeoffs
Deferring income to a lower future tax bracket sounds simple. In practice, an unsecured promise from your employer carries a risk most executives underprice.
- How Board Compensation Is Actually Taxed
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.
- Philanthropic Giving Strategies for High Earners: DAFs and Charitable Trusts, Plainly Explained
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.
Risk
Concentrated stock positions, change-in-control severance and excise-tax exposure, and disability and key-person insurance.
- Managing Concentrated Stock Position Risk Without Signaling
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.
- Golden Parachute and Severance Tax Planning for Departing Executives
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.
- Executive Disability and Key-Person Insurance: Two Different Problems
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.
California household
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 Disability Insurance Basics
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.
- How California SDI Interacts With Retirement Planning
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.
- Community Property Rules in California Divorce and Estate Planning
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 Residency Tax Rules for Remote Workers
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.
- Prop 13 and Inherited Property in California
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.
- California 1031 Exchange Basics for Real Estate Owners
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.
- Comparing California Credit Unions vs Banks for Savings
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.
- California First-Time Homebuyer Assistance Programs
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.
- CalSTRS and CalPERS Pension Basics for Public Employees
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.
- Small-Business Owner Tax Planning in California
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.