Insights
Field notes.
Written by the principals · Not by marketing
Notes on structure, sequence, and timing, written for people who already understand their own finances and want the reasoning rather than the reassurance.
All notes
46 notes
The Vesting Calendar You Did Not Set
Restricted stock is taxed on delivery, on a schedule an employer chose, at a withholding rate set by statute rather than by your circumstances. Almost every lever sits before the vest date.
On the Order of Operations
Preservation, protection, and growth are each well-trodden ground. Almost nobody runs them in sequence, and the order turns out to matter more than the individual decisions.
The Limit Nobody Models
A large first-year deduction is worth very different amounts to two taxpayers with the same income this year and different income next year. The provision that decides it moved against taxpayers in 2026, and almost nobody has noticed.
The IRS Is Moving From Blanket Programs to Case-by-Case Review
Standardized enforcement programs are giving way to specialist offices, self-service compliance is becoming something a third party can verify rather than take on faith, and new savings vehicles keep opening for investment before their governing rules are final. Read together, they describe a durable shift, not a news cycle.
The Closing Window and the Permanent One
The investment credit, its adders, and permanent 100% bonus depreciation still combine powerfully. But the begin-construction deadline for wind and solar has now come and gone, and that quietly changed which projects are worth looking at.
The Stack, and the Question Beneath It
Historic credits, state historic credits, New Markets allocation, and tax increment financing can combine into an unusually favorable capital stack. They can also make a bad project look financeable.
New Markets: A Subsidy Delivered Sideways
A program that subsidizes a developer through an investor, now permanent for the first time in its history. What the mechanism is, where the benefit is created, and how it reaches the people who fund it.
Withholding Is Not a Tax Plan
The rate your employer applies to a vest is a statutory default, not a calculation of what you owe. At this income level the gap is routinely six figures, and it arrives with a penalty attached.
On Concentration: The Argument You Least Want to Hear
The tax cost of selling is the reason most holders never diversify. It is also the reason the position keeps growing relative to everything else they own.
The Thirty-Day Window
The 83(b) election has no extensions, no late relief, and no second attempt. It is also sometimes the wrong thing to file.
Qualified Small Business Stock and the Discipline of Five Years
Section 1202 is the most valuable provision available to most founders. In 2025 it split into two parallel regimes, and which one applies to you depends on a single date.
Before the Window Closes
Almost everything worth doing ahead of a liquidity event has to be in place before the event is announced, and much of it before it is contemplated.
Aligning the Plan to the Vest Schedule
An offsetting position has to land in the year the income actually spikes. Overshoot it and the excess does not simply wait for you, it arrives diminished.
Elections Made a Year in Advance
Non-qualified deferred compensation defers tax on money the executive has already earned. The regime governing it is unusually unforgiving, and the penalty for failure falls on the participant rather than the company.
Material Participation Is a Records Question
Whether a loss offsets your salary or sits trapped against passive income turns on seven tests. All of them are satisfied with contemporaneous records, and none of them with intention.
At Risk: The Question That Decides Whether a Deduction Is Real
Two investors can write identical checks into an identical structure and deduct very different amounts. The variable is what each of them genuinely has at stake.
Your Entity Was Designed for a Company You No Longer Run
The structure was chosen at formation to solve a smaller problem. The business changed underneath it, and almost nobody goes back.
Reasonable Compensation, and the Case You Would Have to Make
There is no formula and no safe percentage. There is a position you would have to defend, and most owners have never written it down.
The K-1 That Arrives Whether or Not the Cash Does
Pass-through income is taxed on allocation, not on distribution. In a growing business the gap between the two comes out of your personal balance sheet.
Electing Out of the Installment Method
A sale paid for over several years is taxed over several years unless the seller says otherwise. There are sound reasons to say otherwise, and a decision made by default is not one of them.
The Largest Deduction Most Owners Never Take
A defined benefit plan can generate a deduction several times the size of anything available through a profit-sharing arrangement. The constraint is rarely the law. It is the employee census and the willingness to commit.
Risk, Genuinely Transferred
A captive insurer is a real structure with real uses. The small-company election attached to it has produced a decade of litigation, and the cases turn on a question the marketing rarely addresses: whether the arrangement was insurance at all.
The Cost of Having No Balance Sheet
A capital-intensive business produces tax attributes as a by-product of operating. A consultancy produces none, and everything available has to be built on purpose.
Capacity Unused
The retirement architecture available to a high-earning self-employed professional is considerably larger than most of them use. It requires design, an actuary, and a decision before year end.
Entity Election as a Compensation Decision
Most independent professionals operate as whatever they registered on day one. The alternative is not a formality, it changes how your income is characterized.
The Professional's Exposure
For a licensed professional, the liability created by the work and the assets built from the work frequently sit on the same balance sheet, separated by an insurance policy and not much else.
Two Trusts and the Doctrine That Collapses Them
Spousal trusts are the usual answer to giving away an asset while keeping indirect access to it. Run symmetrically, they are also the fact pattern a 1969 Supreme Court decision was written to defeat.
The Tax Paid by Someone Else
A trust can be complete for estate tax purposes and simultaneously ignored for income tax purposes. The gap between those two treatments is one of the most durable planning mechanics in the code, and it works by making the settlor pay a bill that is not theirs.
What a Minority Interest Is Actually Worth
A non-controlling interest in a private entity is worth less than its share of the underlying assets. That proposition is ordinary commercial sense, it is worth a great deal in transfer tax, and it is defensible only where the entity is real.
Where Trust Income Is Taxed
A non-grantor trust reaches the top marginal rate at a level of income that would barely register on an individual return. The rules that move income out to the beneficiaries are therefore not administrative detail, they are most of the planning.
Insurance Held Outside the Estate
Life insurance proceeds are generally free of income tax and routinely subject to estate tax. Whether the second applies is decided by who owns the policy, and by when that ownership was arranged.
Real Property Only
The like-kind exchange survived the 2017 legislation in a narrower form, and on a timetable that does not bend. Most failed exchanges fail on the calendar rather than on the law.
What a Cost Segregation Study Does Not Do
A study reclassifies parts of a building into shorter recovery periods and accelerates the deduction. It does not create a deduction, does not make a loss usable, and does not survive a sale without consequence.
The Hours Nobody Documented
Real estate professional status turns rental losses from suspended to usable, which makes it one of the most valuable positions available to a high earner. It is also among the most frequently claimed without the records that sustain it.
Seven Days, and What Turns On Them
A property let on short stays may not be a rental activity at all for passive loss purposes. The position is legitimate, it is narrower than the version circulating online, and it does not depend on real estate professional status.
The Same Deal Is Worth Less in California
A state that will not follow the federal rules does not merely shrink your benefit. It changes which kind of position is efficient for you at all.
Three States That Will Not Follow
California, Illinois, and New Jersey each break the central federal planning move, and they break it in three different ways. Only one of the three is a timing problem.
The Workaround the States Built
The federal cap on deducting state and local tax was answered, in most states with an income tax, by moving the liability to the entity. The election is usually worth making and it is not automatic, not uniform, and not always correct.
Leaving a State Is a Question of Proof
A change of residence is asserted on a return and established in an audit. The states that matter most here are the ones least willing to accept the assertion, and the evidence they want is generated during the year, not afterwards.
Bonus Depreciation Is Permanent. That Changes the Question.
For several years the correct advice was to move before the percentage stepped down. That pressure is gone, and its removal is itself the planning point.
The Truth About Non-Cash Charitable Contributions
The category with the widest gap between what is marketed and what survives examination. What a defensible contribution actually requires, and why most of what is sold does not meet it.
The Deferral With a Fixed End Date
The opportunity zone program offered three benefits on three different timetables. Two of them closed on dates that have passed, and the deferral itself was always scheduled to end on a date set in the statute.
The Surtax That Sits Above the Bracket
A separate levy applies to investment income above a threshold that has never been adjusted for inflation. Whether particular income is caught turns on a question most people answer by assumption: how the taxpayer participates.
The Basis That Has to Be Tracked
Two well-known routes put money into a Roth account above the income limits. One is defeated by a rule that aggregates accounts most people forget they have. The other depends entirely on what an employer's plan document happens to permit.
The Deduction That Became a Listed Transaction
Conservation easements are a legitimate and long-standing provision. The syndicated version, sold on a multiple of the capital contributed, is a different thing, and its history is the clearest available account of how these arrangements end.
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