Stage 3
RSU & Equity Compensation
Stock compensation creates concentrated positions and tax timing decisions that most content handles poorly. The default answer for RSUs is almost always: sell at vest and diversify.
These frameworks help you evaluate whether holding is actually justified — and how to handle the withholding trap, concentration risk, and multi-year vesting schedules.
Core rule: Your income and career are already tied to your employer. Holding RSUs adds a second layer of employer exposure to your portfolio. Evaluate holding as a standalone investment decision — not as loyalty or optimism.
RSUs vest as ordinary income. Holding is a new investment decision. How to evaluate it — concentration risk, tax timing, withholding traps.
ESPP Strategy
SoonThe 15% discount is guaranteed return. When to sell immediately vs hold for qualifying disposition.
ISO and AMT
SoonIncentive stock options can trigger AMT on paper gains. How to model before exercising.
RSU Sell vs Hold Calculator
SoonAfter-tax comparison of selling at vest vs holding concentrated stock for various time horizons.