Equity compensation basics
The building blocks. What your options and shares actually are, and how each one is taxed.
ISOs and AMT
Why exercising incentive stock options can trigger a tax bill before you sell a single share, and what to consider.
Read the explainerNSOs vs ISOs
Two kinds of stock options, two very different tax stories. How to tell which you have and what it means.
Read the explainerRSUs and how they're taxed
Restricted stock units are taxed as income when they vest. What that means for withholding and your next return.
Read the explainerThe 83(b) election
A short filing with a hard deadline. What the 83(b) election does, who it helps, and why the clock is so unforgiving.
Read the explainerESPP taxes
Buying company stock at a discount through payroll. How the lookback works, the $25,000 limit, and how the shares are taxed when you sell.
Read the explainerThe AMT credit
Paid AMT on an ISO exercise? Much of it is recoverable over time. How the minimum tax credit and Form 8801 work, and why records matter.
Read the explainerWhen equity loses value
The tax side of a drop or a wipeout: phantom income, worthless-stock rules, Section 1244 ordinary losses, and the capital-loss limits. What to claim, and when.
Read the explainerLiquidity events
When the shares finally turn into something you can spend, and the planning that protects what you keep.
Equity at an IPO
When your company goes public, double-trigger RSUs settle and get taxed, often before the lockup lets you sell. Where the cash crunch hides and how to plan for it.
Read the explainerQSBS
Qualified small business stock can exclude a large share of gain from tax. The catch is in the qualifications and the holding period.
Read the explainerTender offers & secondary sales
Selling private shares before an exit. Usually capital gain, but a premium above fair market value can be taxed as compensation. What to check before you sell.
Read the explainer10b5-1 trading plans
A securities-law tool that lets insiders sell stock on a preset schedule. How it works, the cooling-off period, and where the tax planning fits.
Read the explainerWealth distribution and charitable giving
The phase where the question shifts from building wealth to directing it, to family, to causes you care about, or both. The 2026 rules under the One Big Beautiful Bill Act changed this landscape, and these explainers reflect current law.
Donor-advised funds
A flexible giving account that lets you take the deduction now and direct the grants later. Why bunching into a DAF is one of the most tax-efficient ways to give in 2026.
Read the explainerQualified charitable distributions
If you are 70.5 or older, you can send IRA money straight to charity and exclude it from income entirely. The $111,000 limit and how it satisfies your RMD.
Read the explainerCharitable remainder trusts
Turn an appreciated asset into a lifetime income stream while supporting a cause. How the trust works, the upfront deduction, and who it fits.
Read the explainerStrategic gifting to heirs
The annual exclusion, the new permanent $15 million lifetime exemption, and how to move wealth to family tax-efficiently under the 2026 rules.
Read the explainerGiving appreciated stock
Why donating shares you have held over a year is almost always better than donating cash, and how to do it without triggering capital gains.
Read the explainerEstate planning and the CPA
What I handle versus what your estate attorney handles, and why coordinating the tax view early saves money later.
Read the explainerKey deadlines
The dates that do not move. A quick reference for the equity-comp clocks that carry real consequences if you miss them.
Not sure which question is yours?
That is normal, and it is a good reason to talk. Helping people sort out which of these actually applies to their situation is a lot of what I do. If you are facing an equity decision or a liquidity event, here is how to start a conversation.
Become a ClientEverything in this section is general information, not tax or legal advice for your specific situation. Tax outcomes depend on your individual facts, and the rules change over time. Talk to a qualified professional (I am happy to be that person) before acting on anything here. Reading these pages does not create a client relationship.