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AI agent for financial advisors

Concentrated Stock Position Agent

Reduce concentration at an acceptable tax cost within legal trading windows

Concentrated Stock Position Agent: what goes in, what the agent does and what you get

What it does

A client holds 60 percent of a portfolio in the employer's stock with large gains and sells only in short trading windows. This agent reads the client's holdings, tax lots and the employer's trading windows and measures concentration. It models staged sales over several years, gifting of appreciated shares, charitable options and hedges, and compares the tax cost and remaining risk for each. It checks the plan against blackout dates and plan rules. It reruns the models after price moves or new windows. It draws up a plan with the sales schedule and the tax estimate. The advisor approves the plan before it goes to the client. Edge case: shares with a restriction or holding period are modeled separately from freely tradable ones.

How it works

Follow the arrows from top to bottom. The orange dashed arrow is the loop: when a check fails, the agent goes back and tries again.

Start and resultWhat it doesA check on its own workWaits for your OKGoes back and retries
Yes, continueYes, continueApprovedNoNo 1 STARTS WHEN Trading window opens or price moves sharply 2 USES A TOOL Read holdings, tax lots and window dates 3 DOES Measure concentration and unrealized gains 4 DOES Model staged sales, gifts, charitable gifts andhedges 5 CHECKS THE RESULT Does each option respect windows, restrictions andrules? If not: Drop or adjust the option and remodel. Back tostep 4. 6 DOES Compare tax cost and risk reduction 7 CHECKS THE RESULT Does the best option reach the concentration target? If not: Extend the schedule or combine options andrerun. Back to step 4. 8 DOES Draft the plan and sales schedule 9 YOU APPROVE Advisor approves the plan before it goes to theclient 10 RESULT Diversification plan and schedule
Read the steps as a list
  1. Trading window opens or price moves sharply
  2. Read holdings, tax lots and window dates
  3. Measure concentration and unrealized gains
  4. Model staged sales, gifts, charitable gifts and hedges
  5. Does each option respect windows, restrictions and rules?If not: Drop or adjust the option and remodel. Back to step 4.
  6. Compare tax cost and risk reduction
  7. Does the best option reach the concentration target?If not: Extend the schedule or combine options and rerun. Back to step 4.
  8. Draft the plan and sales schedule
  9. Advisor approves the plan before it goes to the clientThe agent waits here for your OK.
  10. Diversification plan and schedule

How it decides

It chooses the schedule that gets concentration under the target with the lowest total tax and respects windows and restrictions.

  • Target concentration under 20 percent of the portfolio or the client's chosen limit
  • Sell only in open windows
  • Use highest-cost lots first when selling
  • Keep restricted shares in a separate model

Make it yours

Every agent is a starting point. You choose these settings for your own situation.

  • Concentration target (default 20 percent)
  • Options modeled (default sales, gifts, charity, hedges)
  • Lot selection method (default highest cost first)
  • Review trigger (default window open or 10 percent price move)

What keeps you in control

It always asks you first

  • Advisor approves the plan before it is shown to the client
  • Client approves each sale through the advisor

Hard limits

  • Never place trades
  • Never present advice without advisor approval
  • Never trade in a blackout period

It stops when

  • Done: Concentration at target
  • Stop: Legal restriction blocks the plan, so hand to the advisor and counsel

Set it up

We guide you through the set-up, step by step

Members get the full set-up guide for this agent. No technical skills needed: you copy, paste and upload.

10 minto set it up in your AI
5 AIsChatGPT, Claude, Copilot, Gemini, Grok
  • One set of instructions to paste into your AI, with the clicks for ChatGPT, Claude, Microsoft 365 Copilot, Gemini and Grok
  • The agent then walks you through connecting your own data, one source at a time
  • A downloadable copy with the flow chart, the rules and the full guide
Get access to this agent

An example run

What happensA client holds $1.8 million of employer stock, 62 percent of the portfolio. Selling it all would cost $310,000 in tax. The agent models three years of staged sales and gifting $100,000 of shares. Option B keeps tax to $188,000 and reaches 18 percent by year 3. A blackout blocks March. The advisor approves the plan.

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