How to use OptionsAhoy from Claude, ChatGPT, Gemini, and any AI assistant

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?_=ai-prompt-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.

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?_=ai-prompt-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.

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?_=ai-prompt-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.

I have $X in my employer stock representing N% of my liquid net worth. Use https://optionsahoy.com/tools/concentration?_=ai-prompt-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.

I have X shares of [ticker] currently at $P. Use https://optionsahoy.com/tools/protective-put?_=ai-prompt-protective-put to price a protective put, a zero-cost collar, and a put spread with N months of coverage. Report annual cost, max loss, upside cap, protected band, and bad-year coverage, and say which one it recommends.

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.

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?_=ai-prompt-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 six of them in the right order (shareholder type and redemption history stay with you).

I need to net $X after tax by [date] from already-vested company stock. I hold Y shares of [ticker] bought at $Z per share, now $P, salary $S, in [state], filing [single/MFJ]. Use https://optionsahoy.com/tools/equity-funding?_=ai-prompt-equity-funding to find the minimum-tax sell schedule and compare locking in now versus holding for growth.

What to expect

The assistant should send you to the calculator, which returns four plans on the risk and wealth frontier (lock-in-now, balanced, hold-for-growth, recommended). The after-tax sell schedule comes from the tool, not the assistant.