AI Under Management/October 9, 2026
AI Under Management

Second Opinion

ChatGPT can now read your clients’ accounts for free. Get to their questions before it does.

Tim Diemer
· 7 min read

Doctors have a new kind of patient. They sit down already holding a diagnosis, a list of follow-up questions and a treatment plan, courtesy of a late-night conversation with ChatGPT. The appointment isn’t about figuring out what’s wrong anymore. It’s about responding to a second opinion that got there first.

OpenAI says more than 300 million people a week ask ChatGPT health questions. Now the same thing is coming to money. On October 2, OpenAI started rolling out Finances in ChatGPT to its free users in the U.S. Link your accounts, investments included, and it reads the balances, the transactions and the holdings, then answers whatever you ask.

Picture that patient in your conference room. They’ve already asked whether they’re on track to retire, whether they can afford the lake house and whether their bond allocation makes sense. Some of the answers are good. Some miss the plan behind the numbers. All of them came free, from something that read their statements the night before.

Also inside: Build This: a brief on the news behind everything you own and watch, ready before the open. Asked This Week: putting AI inside the spreadsheet you already have open. And in What Moved, the FTC is looking at AI agents, and the SEC’s exam staff says annual reviews are missing changes in how firms work.

This is issue 4 of AI Under Management. It runs every other week for people at wealth and asset management firms who want real work out of this without creating a problem for themselves. If you know someone who’d want it, send it their way.

BUILD THIS

The morning brief

Before the open every weekday, Claude reads the news on everything you own and watch, and hands you one page.

1. Make your list. Every holding in your model portfolios, plus the names you’re watching, by name and ticker. Use the models, not client accounts. This runs on public news.

2. Schedule it. In Cowork, tell Claude to run the following every weekday at 6:30 a.m. Eastern, paste in your list, review what it proposes and click Schedule:

“Put together my morning holdings brief. Holdings: [list]. Watchlist: [list]. For each name, search for news since the previous market close (on Mondays, since Friday’s close). Report only what’s new: earnings and guidance, analyst rating changes, management changes, deals, legal or regulatory actions, dividend changes, and any price move larger than 3% in the last session. Start with anything I should know before the open. Then give one line per name that has news, and put every name with nothing new on a single Quiet line. Link each item to its source and give the source’s publication date. If you can’t confirm a fact or a price move from a source, say so instead of estimating. Keep it to one page.”

3. Keep it current. When the models change, click into the task and edit the list.

Analysts I work with run versions of this every morning. On one day’s news, across a twelve-stock model and a four-name watchlist, it covered all sixteen names, put eleven on the Quiet line, and caught an overnight report of Apple cutting iPhone orders, the late-day Medicare star ratings news for UnitedHealth, and why Broadcom fell more than 4%. It said plainly when it couldn’t find why Home Depot moved. Two tips. If you cover a lot of names, give each strategy its own task so every brief stays focused. And click the link before you repeat anything to a client. Price moves come from financial websites, and one auto-generated movers page had Exxon up more than 3% when the price history showed 2.71%.

THE MEMO

Second Opinion

OpenAI previewed Finances in ChatGPT for Pro subscribers in May, opened it to Plus in June and started rolling it out to free users this month. It connects through Plaid to more than 12,000 institutions and can’t move money or change anything. OpenAI says more than 200 million people come to ChatGPT every month for help with budgeting and investing.

Meta’s new agent, Muse, launched in September on the same plumbing. Plaid says Muse users can share “balances, transactions, investment holdings, mortgage information and more.” On Claude, personal finance apps such as Era and Truthifi offer connectors that let people link their financial accounts.

The patient already asked

The obvious worry is that this replaces you. A recent survey says otherwise. Betterment Advisor Solutions surveyed 1,001 U.S. investors who already work with an advisor: 75% use AI at least occasionally for financial questions, 76% would still want a human advisor even if AI could answer most of their questions, and 3% would replace their advisor with AI outright. Betterment sells to advisors, so read it with that in mind.

What changes is the meeting. A client who’s been asking ChatGPT about their portfolio shows up with the questions it raised. Why so much cash? Am I too concentrated? What am I actually paying? Those are good questions, and they come from engaged clients. Betterment makes the same point: AI use can be a sign of engagement, not drift.

And the second opinion may know things you don’t. The client’s assistant sees whatever they link: the checking account, the credit cards and, where the provider is supported, the 401(k) you don’t manage.

The catch is timing. If the client raises it first, you’re answering the second opinion. If you raised it last month, the second opinion agrees with you.

Get there first

Some clients won’t stop at questions. They’ll arrive with the assistant’s suggestions: move the cash, trim the tech, pay down the mortgage first. Some of those will be good. Others will come from an assistant that sees the balances but not the plan behind them. OpenAI’s own page says Finances “is not a replacement for professional financial advice,” but a client may weigh its suggestions anyway. Be ready to answer each one with the reasoning it couldn’t see.

So find out what they’ve been asking. At your next round of reviews, ask clients whether they’ve connected their accounts to ChatGPT or anything like it, and what they asked. The ones who have are handing you their list of worries, and it’s better on your agenda than in your inbox.

Then put the same tools to work on your side. Your client’s assistant looks at one household when they think to ask. Yours can look at everything you manage, every morning. Start with what’s public: a brief on your model holdings means you’ve read the headline before a client’s assistant explains it to them. Once your setup covers client data, a custodian connector like Schwab’s gives Claude balances, positions and transactions, enough to flag which households have cash that hasn’t moved in months, or a single position above a fifth of the account, so you can call them before they call you.

ASKED THIS WEEK

How do I use AI on the spreadsheet I’m already working on?

Put Claude inside the spreadsheet. If your day runs through Excel or Google Sheets, start here. A chat upload hands you back a new copy. The add-ins work in the file you have open.

Ask it for the formula you’d otherwise look up, or why one is throwing an error. Have it clean a messy export, sort and filter, add conditional formatting or dropdowns, or fill in a model from a template. It can pull outside data in through connectors. In Excel it shows how a number was built, with links to the cells, and changes an input without breaking the formulas around it.

Claude for Excel is on Claude’s Pro, Max, Team and Enterprise plans: install “Claude for Microsoft 365” from Microsoft’s add-in store. Claude for Google Workspace, covering Sheets, Docs and Slides, opened to paid plans as a public beta this week.

One habit: once it gets a recurring job right, turn the steps into a skill, so next month’s version is one request.

Have a question you’d like answered here? Reply to this email.

WHAT MOVED

The FTC is looking at AI agents

On September 30, an FTC spokesperson confirmed the agency is investigating OpenAI, Anthropic and other AI companies over possible risks to consumers, amid recent disclosures of AI agents acting outside what people told them to do. No action has been announced. For your firm: before anyone connects an agent to anything, know what it can do, not just what it can read. A read-only tool like Finances in ChatGPT is a different conversation from an agent that can send, buy or move money.

Your annual review is supposed to notice AI

On September 14, the SEC’s exam staff published what it found looking at advisers’ annual compliance reviews. One problem: firms that “did not consider changes in their business activities” when deciding whether their policies still fit. The alert never mentions AI. If your team started using an AI tool this year, that’s a change in how the firm works, and a review that skips it is the gap the staff described. If yours is still ahead of you, add a line for it.

Next issue in two weeks. Forward this to whoever at your firm gets handed the AI question, and reply if you want to talk about any of it.

Tim Diemer
Partner and COO, Bridge AI Consulting

This is general information about published rules and products, not legal or compliance advice. Run your own facts past your own counsel and CCO.

Know a firm that should be working with us? Refer them to Bridge AI and we’ll pay you 10% of their first year.

Tim Diemer
Tim Diemer
Partner & COO, Bridge AI Consulting

Tim built the internal AI workflows and training systems that got developers at Epic Systems using AI every day. He's a Partner and COO at Bridge AI.

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AI for wealth managers, RIAs and finance teams: what to build now, what compliance actually requires, and what moved. From Bridge AI's Tim Diemer. New editions every other Thursday. Free forever.

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