RSUs are taxed as income the day they vest, and most employers withhold at a flat 22%, well below what many employees owe. ISOs can trigger alternative minimum tax on shares you haven’t sold. Without a plan, stock grows into most of your net worth and the tax arrives in one bill.
Employees of public and late-stage private companies with RSUs, options or ESPP, especially anyone with a vest, IPO or tender offer in the next two years.
A vest-by-vest calendar with the tax on each
Withholding top-ups and estimated payments set to your real bracket
ISO exercise modeling, including AMT
ESPP sale timing (qualifying vs disqualifying)
A written plan to reduce a concentrated position over time
Coordination with your employer’s trading windows
First meeting
We read your grant agreements and build the vest calendar.
Before each vest
Sell-or-hold decision and withholding checked.
November
ISO exercise amount set against AMT for the year.
Every year
Concentration target reviewed; diversification continues.
Selling enough shares at each vest to cover the tax the 22% withholding misses.
Exercising ISOs in December up to the point where AMT begins.
Bringing one company’s stock from 60% of net worth to 25% over three years.
Examples describe typical situations, not the results of any specific client. Outcomes depend on your circumstances.
Should I sell my RSUs when they vest?
What is AMT and why does it matter for ISOs?
My company is private. Can you still help?
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