How I Use ChatGPT as My Investment Advisor

I trained AI to act like my investing intern - and it's scary how good it is

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My investment accounts are spread across a few platforms.
Some are mine. Some are my wife’s.

It’s messy, and I need to waste time logging into different banks to figure out how much money and investments we have.

I find that banks are extra annoying to log into because I have to keep putting in a phone verification code along with my password.

ChatGPT for Investments

The first thing I did with ChatGPT was to get all of our bank and investment accounts on one screen so I could analyse them properly.

Step 1: I Upload Screenshots of Everything

We each have different accounts at TD and National Bank. I took screenshots of my holdings in each account. (I probably had over 15 screenshots).

Here is an example of a screenshot (blurred out for my privacy)

Andrew Best Investments Blurred out (ChatGPT)

Step 2: It Gives Me a Visual Breakdown

Within seconds, ChatGPT shows me what we have. It tells me the number of shares we own in each company, the price per share, and the dividend income we earn from each stock.

Screenshot of Andrew Best Investment holdings (blurred)

I then ask ChatGPT to make a pie chart of my holdings.

This is a sample pie chart it made (not my real holdings).

Note: This is an image, so it looks a bit “off”, but if you use your real screenshots, it will work properly.

Step 3: I Ask What I’m Earning in Dividends

I like buying dividend stocks. These stocks pay me an income every month (or every 3 months), depending on the stock.

ChatGPT is able to quickly calculate how much I’m earning every month and make a chart showing how much dividend income I’m earning each month.

Remember, some months earn more than others because some stocks pay once every 3 months.

It will also tell me how much I will earn in X number of years if the dividends increase by a certain percentage every year, and if I reinvest the dividends.

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Step 4: I Ask What I’m Missing

I get ChatGPT to analyse the countries and sectors of the economy I’m invested in.

I ask which sectors I’m “overweight” in and which ones I’m “underweight”.

I ask for advice on making a more diversified portfolio in terms of international exposure.

I also ask ChatGPT to search the internet and give me a list of options for individual stocks I might want to consider purchasing, and to give me a brief overview of each one.

The ones that look interesting to me I will research further, using ChatGPT’s “deep research” feature.

I would never blindly follow ChatGPT’s advice or suggestions, but the research it provides saves me a ton of time, and it acts like a super-smart and hard-working intern.

Step 5: I Push It Further

I tell ChatGPT my age and investing goals. I tell it my risk tolerance.

I even tell it the types of accounts I have.

For example, some of my investment accounts offer tax-free growth. ChatGPT suggests which accounts I should be purchasing which stocks and why.

I also ask ChatGPT which stocks I should consider in a rising interest rate environment and why. It makes it a cross between an advisor and a macroeconomist.

Why I Keep Using It

It’s not perfect. But it’s fast. It’s visual. It keeps me thinking.
And it gives me better questions to ask — without pretending to be a guru.

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