How to use AI to keep track of your stock portfolio

The most useful way to track your portfolio with AI is to connect your holdings to an assistant like Claude or ChatGPT, then use it for a short weekly review: what's the news on what I own, what reports earnings soon, and has anything changed my reasons for owning it. The AI does the gathering and explaining. You do the deciding.

This post covers how to set that up, what a good routine looks like, and where AI helps and where it doesn't.

What "tracking" should mean

Your brokerage app already shows you prices, gains and losses. Staring at those numbers is not the same as tracking your investments. Useful tracking answers different questions:

• What happened to the companies I own this week, and does any of it matter?
• What's coming up, like earnings reports or dividend dates?
• Am I more concentrated in one stock or sector than I meant to be?
• Do my original reasons for owning each position still hold?

These are reading-and-thinking questions. That's the kind of work AI assistants are good at, as long as they have the right data.

Step 1: Give the assistant your real holdings

An assistant can't track what it can't see. You have three options.

1. Paste your holdings in. Fine for a single conversation, but it goes stale the moment you trade.
2. Upload a statement or export. Same problem, with more steps.
3. Connect your brokerage read-only. The assistant reads your current positions whenever you ask.

Option 3 is the one that makes a routine sustainable. Bywell connects Wealthsimple, Questrade, TD Direct Investing, Interactive Brokers and 20+ more brokerages through SnapTrade, read-only, and makes your holdings available in Claude, ChatGPT, Codex, Gemini and other assistants that support MCP connectors. The setup is in How to connect your brokerage account to ChatGPT or Claude.

Step 2: A 15-minute weekly routine

Pick a regular time, like Sunday morning, and work through these questions with your assistant. The prompts are examples; phrase them however you like.

1. The news check. "What's the news on my holdings from the past week? Group it by company and tell me which stories could change the long-term picture and which are noise."

Most headlines are noise: price-target tweaks, vague rumours, hot takes. Signal tends to be earnings, guidance changes, leadership changes, big contracts, regulation, or shifts in the industry. Asking the assistant to sort them saves you from reacting to the wrong ones.

2. The calendar check. "Which of my holdings, or anything on my watchlist, report earnings in the next two weeks?"

Knowing the date means you won't be surprised by a big move. You can also set a reminder for the day before. More on this in How to get earnings reminders for the stocks you own.

3. The shape check. "Show me my holdings by portfolio weight. What share is in my top three positions?"

Concentration isn't automatically bad, but it should be deliberate. A stock that has grown a lot can quietly become a large part of your portfolio.

4. The thesis check. "For my largest position, what's the bull case and the bear case right now, with sources and dates?"

If you've written down why you own something, compare the week's news against it. If you haven't, ask the assistant to help you write a one-paragraph thesis, including what would change your mind.

Step 3: Go deeper when something happens

The weekly routine keeps you informed. Events call for a closer look.

• After an earnings report: "Walk me through the latest results for this company. Did it beat or miss estimates, and what did it say about the next quarter?" See How to read an earnings report.
• After a big price move: "This stock fell sharply this week. What news came out, and when?" Often the answer is expectations, not results. Why a stock can drop on good earnings explains why.
• Before adding to a position: "Pull the fundamentals for this stock and compare them to a peer." Remember that numbers like P/E only mean something next to history and peers.

Where AI helps, and where it doesn't

AI is genuinely good at:

• Summarising a week of news across many companies in a few paragraphs.
• Explaining terms like EPS, guidance or beta in plain language, using your own holdings as the example.
• Laying out arguments on both sides of a question.
• Remembering to ask the questions you'd skip when you're busy.

AI is not good at:

• Predicting prices. Nobody is, and an assistant that sounds confident about it should make you more careful, not less.
• Knowing your full situation: your goals, your timeline, your taxes, how you'd feel about a 30% drop.
• Being right every time. It can misread a number or attach a headline to the wrong company.

So ask it to explain, not to decide. Ask for sources and check dates. For anything important, go to the primary source, like the company's own filing.

This is general information, not investment advice.

A note on tools built for this

You can do a lot of the above with a general chatbot and some patience. A connector built for personal investors takes out the busywork. Bywell's tools read your holdings with portfolio weights and allocation, your theses and notes, your goals and contribution room, and set push reminders before earnings. The assistant brings the news and figures with its own web search. It also tells the assistant to show the bull and bear case, cite sources, and not tell you to buy or sell.

What about spreadsheets and tracking apps?

Plenty of investors track their portfolio in a spreadsheet or a dedicated tracking app, and both still have a place.

• Spreadsheets give you total control over calculations, like your own return figures or a target allocation. They need manual updates and don't bring in news.
• Tracking apps show performance charts and allocation well. Many don't explain why something moved.
• An AI assistant with your holdings is best at the reading and explaining: what happened, what's coming up, and what it might mean.

They're not mutually exclusive. A common set-up is a brokerage app for trading, a spreadsheet for long-term planning, and an assistant for the weekly news and earnings review.

Keep it simple

The best tracking habit is one you'll actually keep. A short weekly review, a look around earnings, and a written reason for each position will do more for you than any number of price alerts.

If you want to set it up in a few minutes, start with Bywell's free plan.