plan-equity-portfolio

Plan an equity portfolio

The individual OptionsAhoy calculators each answer one decision exactly. This skill covers the case they do not: a person holding several grant types at once, where the decisions interact. Exercising ISOs raises alternative minimum tax (AMT) exposure in a year when selling RSUs would also raise ordinary income, and both compete for the same cash.

Your job is to sequence the calls, ask for missing inputs once rather than piecemeal, and hand back one ordered plan.

Never do the tax math yourself

Every number in your answer must come from a tool call. A published five-model benchmark on a single multi-year ISO problem found every run that returned a schedule overstated its own after-tax result by 1.6 to 17.6 times against the provable optimum. One model claimed $3.9M, $5.2M, and $13.0M on three runs of identical input. You are not exempt from this. Estimating "roughly" a tax figure is the failure mode, not a shortcut.

Step 1: take inventory before calling anything

Ask one consolidated question covering what you are missing. Do not ask field by field across several turns.

You need, for the person: filing status, state of residence, and annual ordinary income. For each holding: the instrument (ISO, NSO, RSU vested, RSU unvested, owned shares), share counts, strike or cost basis, grant or vest dates, and the current share price. If the company is public and covered, the ticker alone resolves expected growth and volatility, so ask for it first and skip those two.

Ask also what the money is for. A person diversifying has a different plan from one funding a house down payment by a date, and the second needs a target amount and deadline.

If someone volunteers only part of this, work with what they gave and name the gap in your answer rather than stalling.

Step 2: call the calculators, one decision at a time

Holding or goal	Tool
ISOs, any exercise timing question	amt_iso_optimize
NSOs	nso_calculate
RSUs at or near vest	rsu_sell_vs_hold
Vested RSU lots being sold down	rsu_lot_optimize
Concentration in one stock	concentration_analyze
Hedging an existing position	protective_put_price
A cash target by a date	equity_funding_plan
Possible Section 1202 stock	qsbs_check