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Editorial

Wealth decisions that survive board week

Concentration, liquidity, and planning explainers written for leaders who already run complex businesses, plus the California household rules (tax, property, insurance, pensions) that sit beside an executive package.

Articles

Recent articles

The executive briefings connect to a tool or scenario model you can apply to your own equity and liquidity picture; the California household notes explain the rules that sit beside it.

  1. 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.

    Equity events · 4 min

  2. 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.

    Liquidity & tax coordination · 4 min

  3. 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.

    Liquidity & tax coordination · 4 min

  4. 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.

    Risk · 4 min

  5. 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.

    Risk · 4 min

  6. 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.

    Equity events · 4 min

  7. 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.

    Risk · 4 min

  8. 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.

    Equity events · 4 min

  9. 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.

    Liquidity & tax coordination · 4 min

  10. 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.

    Liquidity & tax coordination · 4 min

  11. 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.

    Insurance · 4 min

  12. 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.

    Retirement · 4 min

  13. 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.

    Estate Planning · 4 min

  14. 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.

    Tax · 4 min

  15. 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.

    Property Tax · 5 min

  16. 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.

    Real Estate · 5 min

  17. 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.

    Banking · 4 min

  18. 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.

    Housing · 4 min

  19. 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.

    Public Employees · 5 min

  20. 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.

    Small Business · 4 min

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