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.
Drives chance-of-shortfall · default 30%
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 | $109,048 | $111,357 | $112,141 | $119,083 |
| Wealth @ target | $722,357 | $719,710 | $718,290 | $715,881 |
| Chance of shortfall | <0.1% | 0% | 2.4% | 4.0% |
Feasible
$400,017 net by 08/01/27
Total tax: $109,048 (federal $58,211, state $36,091, NIIT $14,747)
Schedule · Recommended
| Sale date | Shares | Tax | Net | Cumulative |
|---|---|---|---|---|
| 07/18/26 | 3,164 | $272,468 | $280,012 | |
| 07/31/26 | 20 | $1,726 | $281,785 | |
| 08/31/26 | 100 | $8,684 | $290,681 | |
| 09/30/26 | 100 | $8,735 | $299,611 | |
| 10/31/26 | 100 | $8,787 | $308,574 | |
| 11/30/26 | 100 | $8,839 | $317,569 | |
| 12/31/26 | 100 | $8,892 | $326,599 | |
| 01/31/27 | 100 | $8,946 | $335,663 | |
| 02/28/27 | 100 | $8,994 | $344,758 | |
| 03/31/27 | 100 | $9,049 | $353,888 | |
| 04/30/27 | 100 | $9,102 | $363,051 | |
| 05/31/27 | 100 | $9,157 | $372,249 | |
| 06/30/27 | 100 | $9,210 | $381,481 | |
| 07/31/27 | 100 | $9,266 | $390,748 | |
| 08/01/27 | 100 | $9,269 | $400,017 |
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 3,516 shares worth $418,901 at the projected target-date price, invested for the next decision.
You solved for a cash target. The beta optimizes your full portfolio across multiple goals and market scenarios, not just one funding need.
Request beta access →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. At each step it picks the block with the highest conversion benefit: after-tax-and-interest cash now, minus what those shares would be worth held to the deadline. That funds your goal from the holdings least worth keeping, such as a position projected to decline, while retaining the ones expected to grow. It refines 100 → 10 → 1 share blocks until the target is hit; on single-stack inputs the loss vs the true wealth-maximizing optimum stays within 1–2%. The search is deterministic: the 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, CO, CT, 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).
AI assistant integration
Use this from Claude, Cursor, or VS Code
Ask your agent:
“I need $400K after-tax in 3 years from my equity stack. What is the minimum-tax sell schedule?”
With the OptionsAhoy MCP installed, your agent calls equity_funding_plan and returns the same after-tax answer this calculator computes.
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.