A Faster Way to Answer Your Money Questions

You know those money questions that pop into your head when you look at the credit-card bill or notice another subscription charge?

How much is going to subscriptions each month? Why was the bill so high? Is too much cash sitting in the wrong account?

Then there are the bigger questions, where the answer depends on several numbers. What would it take to retire two years earlier? Would it make more sense to pay down the mortgage or invest the money? Is there anything to do before the tax year ends?

Checking one of them can mean logging into several accounts, opening statements, sorting transactions, and comparing numbers. By the time you have seven tabs open, the quick check has taken over your Saturday.

So you close the tabs and tell yourself you’ll come back to it later.

A few months ago, I shared prompts for using AI to think through money questions. Since then, ChatGPT has introduced Finances, which can connect to the accounts you choose, keep your balances and transactions updated automatically, and surface recurring charges, upcoming bills, and changes in spending without you having to gather the information each time.

This post:

Finances is a feature inside ChatGPT that is currently available to U.S. Plus and Pro subscribers.

You choose which accounts to connect through Plaid, a service used by thousands of financial apps. Finances can then show your balances, transactions, subscriptions, bills, investments, cash flow, and net worth in one place.

Connecting an account only allows ChatGPT to review the information you choose to share. It does not give ChatGPT control over the account. It cannot move money, pay bills, make trades, or change your account settings, and you can remove the connection at any time.

If you do not have Finances or would rather not connect an account, you can still use the prompts in this issue. Enter the numbers yourself or upload a statement after removing your name, account number, and other identifying information.

I have used it to:

I use the results to organize the information and think through my options. AI can run the numbers, but it does not know my priorities or which tradeoffs I am willing to make.

Start with the everyday questions. How much are your subscriptions costing? Have any prices increased? Why was the credit-card bill higher this month?

Finances can review your transactions and pull out the charges that deserve a closer look, saving you from working through every statement line by line.

Try:

The result is a shorter list of things to check. If it finds something you want to cancel or dispute, you can ask it to help draft the email.

For perspective, ChatGPT Plus currently costs $20 a month, so finding one unused subscription at that price would cover the monthly plan.

Some financial issues are easy to miss because nothing forces you to check. You may have cash sitting in a low-interest account, overlapping investments, or a fund with a higher fee than you realized.

To review fees and idle cash, try:

A cheaper fund is not automatically better once taxes and transaction costs are included. Use the response to identify what needs more research.

You can also use AI to look for tax questions throughout the year, while there may still be time to act:

This is not a substitute for your CPA or tax attorney. It can help you spot questions during the year, while there is still time to act, instead of discovering them during tax season when some options may have already closed.

Questions such as retiring earlier, paying down the mortgage, or taking time away from work involve several assumptions and personal priorities.

Instead of looking for one perfect answer, ask AI to show you what could happen under different conditions.

Try:

You can ask ChatGPT to put the results into a spreadsheet or chart, then change the assumptions and see how the outcome shifts.

I recently used this approach to work backward from the profitability I wanted for one of our properties. It helped me compare renegotiating with our current property management firm against finding another firm that could lower our expenses.

AI gave me the numbers and options to consider. The final decision still depended on my priorities and the tradeoffs I was willing to make.

Before using an AI analysis to make a financial decision, ask it to review its assumptions:

Asking AI to plan a vacation or suggest a recipe feels very different from connecting a financial account. Your transactions, balances, and investments reveal a lot about your life, so it makes sense to be cautious.

You decide which accounts to connect through Plaid. If you disconnect an account, OpenAI says the synced data will be deleted from its systems within 30 days. Past conversations remain in your history unless you delete them separately.

Your conversations with Finance follow your regular ChatGPT data settings. If you do not want your conversations used to improve the models, go to Settings → Data Controls → Improve the model for everyone and turn it off.

You can skip the account connection and enter rounded numbers yourself or upload a redacted statement. Remove account numbers, Social Security numbers, tax IDs, and other identifying information.

No financial connection is completely risk-free. I’m comfortable using AI as a second set of eyes because I still decide what to share and what to do with the information. You may feel differently, and that’s okay.

If your spouse is not comfortable connecting an account, you can still connect your own accounts and enter estimates for their income, savings, and investments or upload a redacted statement. You will have a partial picture, but it can still help you compare broad retirement scenarios and prepare better questions for your adviser.

If you are the hesitant one, you do not have to connect everything. Start with rounded numbers or one redacted statement, then decide whether you want to share more.

Choose one money question you have been meaning to answer and try the prompt above that comes closest. Use an AI tool you already have, enter rounded numbers yourself, or upload a redacted statement.

You do not need to solve the entire question today. Look for one useful insight, one number to check, or one better question to ask.