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Money, Bills & Benefits

Build a portfolio plan from brokerage exports

Claude Code read a directory of brokerage CSV exports and notes, researched funds, and produced buy, stop-buying and hold lists with a tax-loss harvesting partner fund for each.

Done withClaude Code

What they did
Matt Stockton pointed Claude Code at a directory with brokerage CSV exports, a typed scratchpad of other balances, and a detailed goal prompt covering constraints, strawman targets and "ask me questions exhaustively". Claude wrote Python to parse and classify holdings, then built a gap analysis. Over several sessions he refined constraints, and a CLAUDE.md file carried context between them.
How it went
It produced a ten-section plan with a four-phase action plan, tax payback tables and fund research. He's nearly done executing it. A self-rating of 7.5/10 surfaced improvements, such as using tax-free accounts for the overweight position.
Worth knowing
The goal prompt mattered most. Include constraints, such as accounts you won't touch, and ask Claude to critique its own plan. It took a few evenings across multiple sessions.

Try it yourself with Claude Code

Read the brokerage CSV exports and notes in [folder path]. Research the funds I hold and give me three lists: buy more, stop buying, and hold. For each fund you suggest selling at a loss, name a similar partner fund for tax-loss harvesting and explain the reason. Write the result to a file called portfolio-plan and don't make any trades.

Read the original ↗

Source: mattstockton.com · Feb 10, 2026

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