How to make AI analyze my portfolio?

Yes, an AI assistant can analyze your portfolio — and it is one of the most useful things to do with one. The question is what data it works from. There are two ways to give an assistant your holdings, and they produce very different results.

The problem with pasting a CSV

The usual approach is to export positions from your broker, paste the spreadsheet into a chat, and ask. It works, up to a point, and the point arrives quickly.

• It is stale the moment you export it. Prices, cash and pending orders move; the file does not.
• It is missing most of what matters. A positions export rarely includes tax lots, cost basis per lot, dividend history, realized gains or transaction dates — exactly the fields that questions about taxes, income and performance depend on.
• It has to be redone every time. Each new question means a new export, or an answer based on last week's file.
• It puts your finances in a chat log. A spreadsheet of everything you own, pasted into a conversation, is a document you no longer control.

Connecting your account instead

With Light Horse the assistant reads your account directly. You add Light Horse as a connector in Claude, ChatGPT or Grok, approve access once through OAuth in your browser, and from then on the assistant can call the account's tools itself: positions, balances, transactions, transfers, open orders, statements and tax forms, and live quotes for any symbol.

Analysis is read-only by nature — the assistant is fetching and reasoning, not acting. Nothing in your account changes unless you ask it to place an order, and orders are previewed and confirmed before they are placed. You can disconnect the connector at any time from inside the assistant.

What you can ask

These are real questions people put to a connected assistant. Copy any of them as a starting point.

Concentration and diversification

Look at my positions. What share of the portfolio is in my top five holdings, and how much of it is effectively one bet on semiconductors?

The assistant pulls positions and quotes, works out weights at current prices, and can look through sector and industry exposure — including exposure hidden inside ETFs.

ETF overlap

I hold SPY, QQQ and VGT. How much do they overlap, and what is my true dollar exposure to NVDA across all three?

Holdings for US-listed funds are published on Light Horse's ticker pages, so the assistant can expand each fund into its constituents and add up what you actually own. The ETF Look-Through Exposure Report prompt does this end to end and renders a report.

Dividend income

How much did I receive in dividends over the last twelve months, by month and by position? Which holdings pay the most relative to what I have invested in them?

Transaction history includes every dividend payment, so this is a question about your actual cash flow rather than an estimate from published yields. For the forward-looking version — whether a dividend is safe — see the Dividend Safety prompt.

Cost basis and unrealized gains

For each position, show cost basis, current value and unrealized gain or loss, and flag anything I have held for less than a year.

The holding-period flag matters for taxes; the assistant can separate short-term from long-term positions once it has your transaction dates.

Performance against a benchmark

How has my account done year to date compared with SPY? Account for my deposits and withdrawals so the comparison is fair.

Transfer history lets the assistant allow for cash you added or removed, which a simple start-to-end comparison gets wrong.

Reading your statements

Open my most recent monthly statement and summarize the activity — trades, dividends, fees, and anything unusual.

Statements and tax forms are available to the assistant as documents, so "what was this fee" or "find my 1099 for last year" is a question, not a search through a downloads folder.

Ready-made prompts

The Prompt Library collects prompts like these with a sample result, an estimated token cost and the full text to copy.

What AI cannot do for you

Being clear about the limits is part of using the tool well.

• It is not investment advice. The assistant can describe what you own and how it has behaved. It does not know your goals, your other accounts or your risk tolerance unless you tell it, and it is not a registered adviser. Light Horse is a self-directed brokerage; the decisions are yours.
• It can be wrong. Language models make arithmetic and reasoning errors, particularly over long series of numbers. Treat totals as a first pass and check anything you would act on.
• It works from what it can see. Your account data is complete; market and fundamental data are as good as their sources. Ask the assistant where a figure came from if it matters.
• It is not a substitute for tax advice. Wash-sale and holding-period logic have edge cases. Use the analysis to prepare questions for a professional, not to replace one.