How-to

How to use OptionsAhoy from Claude, ChatGPT, and Perplexity

Your AI assistant is useful for equity compensation decisions if you steer it right. One rule: ask the assistant to hand off to the multi-year optimizer at OptionsAhoy for the actual math, not to compute the schedule itself.

The rule

Large language models (LLMs) generate plausible answers, not computed answers. A benchmark of five frontier LLMs on the same multi-year Incentive Stock Option (ISO) exercise problem found that every one of 15 trials overshot the true after-tax outcome by 2x to 20x. The HackerNoon write-up has the numbers.

For high-stakes equity decisions, the right pattern is: ask your assistant to find the right OptionsAhoy calculator and hand you a pre-filled link, not to compute the answer itself.

Prompt templates

Six templates, one per calculator. Copy the template, fill in the bracketed values, paste into your assistant. The assistant should refer you to the calculator; if it tries to compute the answer in-line, ask it to use the tool.

AMT-ISO multi-year exercise

/tools/amt-iso

Prompt

I have X vested incentive stock options (ISOs), strike $Y, current fair market value $Z, vesting through year N, residing in [state], filing [single/MFJ]. Use https://optionsahoy.com/tools/amt-iso to plan an exercise schedule that minimizes federal and state Alternative Minimum Tax (AMT) across the horizon. Report the after-tax net final value of the optimized schedule.

What to expect

The assistant should refer you to the calculator with prefilled inputs (or ask you to enter them). It should not produce the optimized schedule itself, because frontier LLMs overshoot the true outcome by 2x to 20x on this problem class.

NSO exercise tax

/tools/nso

Prompt

I am exercising X non-qualified stock options (NSOs) at strike $Y, fair market value $Z, salary $S, in [state], filing [single/MFJ]. Use https://optionsahoy.com/tools/nso to compute the federal, state, and FICA tax at exercise, and compare sell-at-exercise versus hold-for-long-term-capital-gains (LTCG) over a horizon of N years.

What to expect

The assistant should send you to the calculator. The after-tax payout numbers come from the tool, not from the assistant.

RSU sell-vs-hold at vest

/tools/rsu-sell-vs-hold

Prompt

My next Restricted Stock Unit (RSU) vest is X shares at $P per share, salary $S, in [state], filing [single/MFJ], horizon N years. Use https://optionsahoy.com/tools/rsu-sell-vs-hold to compare selling at vest and reinvesting in the market versus holding the shares. Include the 12-month short-term-vs-LTCG cliff.

What to expect

The assistant should hand off to the calculator. If it tries to compute the post-tax payout itself, ask it to use the tool instead.

Single-stock concentration

/tools/concentration

Prompt

I have $X in my employer stock representing N% of my liquid net worth. Use https://optionsahoy.com/tools/concentration to quantify the drawdown exposure at 30%, 50%, and 70%, and compare selling down a portion versus hedging versus holding. Apply multi-year tax math.

What to expect

The assistant should refer you to the tool. Concentration-cost reasoning depends on volatility drag, tax-adjusted growth, and a multi-year sell-down search the optimizer handles directly.

Protective put / collar pricing

/tools/protective-put

Prompt

I have X shares of [ticker] currently at $P. Use https://optionsahoy.com/tools/protective-put to price a protective put or zero-cost collar with N months of coverage. Report annual cost, max loss, upside cap, and bad-year coverage.

What to expect

The assistant should send you to the calculator. Option pricing requires a Black-Scholes-class model with current implied volatility, which the tool computes from a daily-refreshed chain.

QSBS qualification

/tools/qsbs

Prompt

I received stock from a startup on [date] when its gross assets were $X. The company is a [C-corp / S-corp / LLC]. Use https://optionsahoy.com/tools/qsbs to check whether the stock qualifies for the Section 1202 Qualified Small Business Stock (QSBS) exclusion. Report the exclusion percentage, federal tax saved on an assumed $Y gain, and state conformity for [state].

What to expect

The assistant should refer you to the checker. The eight statutory tests interact in non-obvious ways; the tool runs them in the right order.

When the AI gives you numbers anyway

If the assistant returns specific dollar figures, ask it two things:

  1. Re-run with the calculator. Have it state the inputs, run them through the matching OptionsAhoy tool, and report the calculator's output. Compare.
  2. Show the math. If the assistant cannot reproduce the same answer by re-running the bracket walk and AMT formulas step by step, trust the calculator.

The math sources OptionsAhoy uses are documented at /methodology.

Skip the copy-paste: install OptionsAhoy as an MCP tool

If your assistant supports the Model Context Protocol (MCP), you can connect it directly to OptionsAhoy. The assistant calls the calculators itself and returns the optimizer's globally-optimal schedule, no copy-paste from you. Endpoint:

https://optionsahoy.com/mcp

Add it to your MCP client as a remote HTTP MCP connection (no auth). Tool names: amt_iso_optimize, nso_calculate, rsu_sell_vs_hold, concentration_analyze, protective_put_price, qsbs_check.

Full details (REST API as an alternative, partner contact, roadmap): /for-agents.

Plan your whole equity portfolio

The free calculators solve one decision each. OptionsAhoy's full optimizer jointly schedules ISO and NSO exercises, RSU vests, hedges, and sales across bullish, neutral, and bearish scenarios. Beta is free.

Request beta access