OptionsAhoy MCP server

This is a helper that lets your AI do real tax math on stock options and RSUs instead of guessing. It works out things like when to exercise ISOs, whether to sell or hold NSOs and RSUs, and whether your shares qualify for QSBS. It is handy if you get equity from your employer and want numbers you can actually check.

What this MCP server does

You describe your situation in plain words: how many shares, your strike price, the current price, your income, your state. Your AI passes those details to this helper. The helper runs the tax math on OptionsAhoy's engine, covering federal rules plus all 50 states and DC. Then it hands the result back to your AI, which explains it to you in the chat.

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What you can do with it

• Build a multi-year ISO exercise schedule that lowers your AMT bill
• Compare selling NSOs at exercise versus holding for long-term gains
• Decide whether to sell RSUs at vest or hold them longer
• Check whether your shares qualify for QSBS tax-free treatment
• Measure how concentrated you are in one stock and what selling down costs
• Price a protective put, collar, or put spread for your position
• Plan which RSU lots to sell and when to hit a target amount

Try asking your AI

• “I have 50,000 vested ISOs at a $4 strike and the stock is at $90. Married filing jointly, $300,000 income, California. Should I exercise all now or spread it out?”
• “5,000 NSOs at an $8 strike, stock at $75. Sell at exercise or hold a year for long-term gains? Single, $250,000 income, California.”
• “1,000 RSUs vesting at $200. Sell at vest or hold another year and a half? Married filing jointly, $300,000 income, New York.”
• “I bought founder stock in March 2020 and I am selling in March 2026 for a $5M gain. Is it QSBS, and how much is tax-free?”

What it gives back to you

You get back clear numbers: your after-tax amount, the tax you would owe, and a recommended plan. For schedules it shows how many shares to exercise or sell each year. For comparisons it shows both options side by side with the dollar difference. Your AI then explains what the numbers mean in the chat.

Before you start

Who it's for

People with employee stock options or RSUs who want to plan exercises and sales without hiring a tax advisor for every question.