Can I connect my stock options to ChatGPT to get advice on them?
San Francisco native (yes, really). @uw and Lowell High alum. I like to nerd out on fintech, stock options and taxes.
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San Francisco native (yes, really). @uw and Lowell High alum. I like to nerd out on fintech, stock options and taxes.
You can connect your stock options to ChatGPT to get advice on them with Secfi’s Model Context Protocol (MCP) server. Because private-company equity comes with a lot of uncertainty, it’s a natural progression to ask the LLM you use every day questions like:
While LLMs can help you model decisions, their estimates shouldn’t be all you rely on. Secfi’s MCP adds a layer of specificity that standard ChatGPT doesn’t have as a text-based prediction engine. However, while AI can help you model financial scenarios, you should make any major decisions with a qualified tax or financial planning professional.
The word advice gets tricky when discussing financial decisions. Language models can explain complex mechanics and help you prepare for discussions with a financial professional.
AI tools can help you by:
However, AI should not be relied upon to:
Large language models can be helpful for explaining stock option concepts and organizing decisions. But they are not calculators by default. They generate predictable text based on patterns, which means they can make calculation errors, overlook assumptions, or produce different answers to similar prompts.
Stock option math can be especially sensitive because small changes in one input can affect the entire model. For instance:
“When it comes to taking decisions about stock options, glitches can have seven-figure consequences,” says Robin Stordeur, Head of Product & Design at Secfi.
That’s why AI is most useful as a planning assistant, not a final decision-maker. It can help you compare scenarios and organize trade-offs, but the data, assumptions, and calculations still need to be checked before you act.
We wrote more about this when developing Maeve, Secfi’s AI equity assistant, which runs on the same calculation engines as Secfi’s MCP.
Secfi's MCP acts as a bridge, letting ChatGPT retrieve structured equity data and calculation tools from your profile during conversations. In the case of ChatGPT, that means you’ll add Secfi’s MCP as a connector.
We believe this approach gives you precision inside the AI assistant you already use, while Maeve remains available if you prefer a dedicated, native equity planning experience.
Once authorized, Secfi's MCP equips your AI assistant with several capabilities:
Active MCP sessions remain authorized for 30 days before requiring a reconnect. You'll need a Secfi account with your grant details added via Carta, document upload, or manual entry to access personalized calculations.
Read more: How to model different IPO exit outcomes for your equity
Connecting your equity data to ChatGPT makes exploring equity compensation planning faster and more interactive. You can run what-if scenarios, test exit valuations, and compare tax outcomes in minutes.
We feel the best strategy is to use AI to organize your options and model possibilities. Once you've mapped out scenarios, verify the numbers with a qualified tax professional or financial advisor before making high-stakes financial commitments.
ChatGPT can explain equity concepts, outline trade-offs, and run financial models when connected to structured tools. They should not replace professional tax, legal, or investment advice. As always, you should consult a tax professional regarding your particular circumstance.
Yes. Secfi's MCP connects ChatGPT directly to your Secfi equity profile and calculation engines once you authorize the session.
To model your scenario, the AI requires your grant type, number of options, strike price, fair market value, vesting schedule, exercise history, household income, and tax filing status.
AI can model exercise costs and tax scenarios, but it cannot make the decision for you. Your choice depends on personal cash flow, risk tolerance, job plans, and tax deadlines.
Yes. The Secfi MCP connects your AI assistant to Secfi's AMT calculation engine to estimate ISO exercise limits and potential tax exposure based on your tax profile. As always, you should consult a tax professional regarding your particular circumstance.
AI can help you understand when option financing applies and allow you to submit a financing inquiry through Secfi's MCP. Final eligibility depends on your company's stage and Secfi's underwriting criteria. There may be additional tax consequences of the non-recourse loan, so it is important to consult your tax professional.
The tool shown here uses artificial intelligence and is for illustrative purposes only and not necessarily indicative of future results and there is no guarantee that similar results can be achieved. The information provided by the tool is not professional advice and is not intended by Secfi, Inc., its affiliates, and Secfi representatives, to be deemed as investment, legal, tax or other professional advice or recommendations of any kind, or to form the basis of any decision to do or to refrain from doing anything. Secfi does not review the accuracy or completeness of the information provided to us within the tool.