Equity to Cash at the Risk You Set
Calculator · free · no signupDown payment in August. Tuition in September. Sabbatical next year. Tell us the after-tax target, the deadline, and the chance of falling short you accept. We calculate the optimal sell schedule that hits your goal with the most wealth at the deadline, using your stock's option-chain volatility.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Inputs
Your equity
One stack per ticker (current-employer RSUs, prior-employer holdings, index fund, etc.). Each stack has its own current price, growth assumption, and cost-basis lots.
Lots
Plan
Estimates only. Not financial advice.
Lock-in-now is deterministic (0%). Plans that wait depend on future prices; risk is near-zero when inventory comfortably exceeds the goal. Volatility: each stack's option-implied vol if a ticker is set, otherwise 30%. Lognormal model; real markets have fatter tails.
| Tax | $111,637 | $110,752 | $111,637 | $119,397 |
| Wealth @ target | $726,476 | $680,919 | $726,476 | $721,823 |
| Chance of shortfall | 2.5% | 0% | 2.5% | 4.8% |
Feasible
$400,051 net by 08/01/27
Total tax: $111,637 (federal $59,593, state $36,947, NIIT $15,097)
Schedule · Recommended
| Sale date | Shares | Tax | Net | Cumulative |
|---|---|---|---|---|
| 06/30/26 | 173 | $14,974 | $15,410 | |
| 07/31/26 | 300 | $26,124 | $42,233 | |
| 08/31/26 | 300 | $26,281 | $69,157 | |
| 09/30/26 | 300 | $26,434 | $96,180 | |
| 10/31/26 | 300 | $26,594 | $123,305 | |
| 11/30/26 | 300 | $26,749 | $150,529 | |
| 12/31/26 | 300 | $26,910 | $177,857 | |
| 01/31/27 | 300 | $27,073 | $205,289 | |
| 02/28/27 | 300 | $27,221 | $232,814 | |
| 03/31/27 | 300 | $27,385 | $260,444 | |
| 04/30/27 | 300 | $27,546 | $288,176 | |
| 05/31/27 | 300 | $27,712 | $316,013 | |
| 06/30/27 | 300 | $27,875 | $343,953 | |
| 07/31/27 | 300 | $28,043 | $372,000 | |
| 08/01/27 | 300 | $28,052 | $400,051 |
Risk vs wealth
Each dot is a possible plan. Right is riskier, up is more wealth left over.
Trajectory of cash netted
Solid line = expected. Shaded band = 10th–90th percentile under price uncertainty.
After the plan
You keep 3,627 shares worth $436,251 at the projected target-date price, invested for the next decision.
What this calculates
- Sell schedule that nets a specific after-tax dollar amount by a target date with the most wealth remaining at the deadline (after-tax cash from each sale compounded at your cash-interest rate, plus the value of the shares you keep).
- Full tax coverage: long-term and short-term federal capital gains, NIIT, and state tax (all 50 states + DC).
- Per-lot selection: the planner picks which lots to sell first based on holding period and basis to land the highest after-tax wealth at the deadline.
- Risk-aware comparison: Lock-in-now, Balanced, Hold-for-growth, and a Recommended plan that picks the highest-wealth schedule whose chance-of-shortfall stays under your tolerance, using each stack's option-implied volatility (or 30% if no ticker is set).
Multi-stack (one or more tickers, each with its own current price, growth assumption, and cost-basis lots). No FICA — sales of already-vested shares don't trigger wage taxes. No AMT — that's for ISO exercise, use the AMT-ISO tool first. Stock prices are projected from your current price using the per-stack annual growth assumption; if the stock moves differently the actual cash outcome will differ from the plan.
Read the deep dive: Cashing out stock for a goal? Convert your risk tolerance into cash. →
Methodology
Optimization. Bracket-aware greedy fill across every (sale-year, sale-month, lot) cell from now through the target date. Each candidate block is priced by its full incremental tax (federal long-term and short-term capital gains, state, and NIIT, per the running year-state) and then grown forward at your cash-interest rate to the deadline. The planner picks the highest after-tax-and-interest cell at each step, refining 100 → 10 → 1 share blocks until the target is hit. For single-stack inputs the loss vs the true wealth-maximizing optimum stays within 1–2%. The search is deterministic — same inputs return the same answer — so the recommendation is verifiable.
Tax-code coverage. Full federal code (ordinary brackets, long-term capital gains, AMT with credit recovery, FICA, Net Investment Income Tax) plus all 50 states and DC for state ordinary brackets and LTCG treatment. State AMT modeled for CA, NY, MN. Brackets reflect IRS Rev. Proc. 2025-32 and the One Big Beautiful Bill Act (OBBBA) provisions for tax year 2026. Validated against 870+ unit tests covering bracket math, AMT credit recovery, state conformity, and the optimizer's search path.
Why use an optimizer rather than asking an LLM to do the math: a benchmark of five frontier large language models on the same multi-year ISO problem found that all 15 trials overshot the achievable after-tax outcome by 2x to 20x (HackerNoon write-up).
This is one slot in a bigger plan.
OptionsAhoy lines up funding decisions, AMT exposure, and the rest of your equity choices across multi-year scenarios. Free during beta.