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ChatGPT is ready to connect to your bank accounts. Should you let it in?

Julian Torres at MarketWatch covered OpenAI's move to let ChatGPT Plus subscribers connect their bank and brokerage accounts through Plaid for personalized money advice, and asked whether people should let it in. Privacy experts raised the obvious concerns. I raised a different one.

The fiduciary point is the part most people miss, and it sounds like a technicality until it is your data. When I take in client data, I am bound by SEC privacy rules and a fiduciary duty. I have to act in your best interest, I have to protect what you share, and there are regulators who can end my career if I do not. A consumer AI product operates under none of that. Its obligations are whatever the terms of service say this month, and the incentives behind the product are not yours.

That does not make the feature useless. Categorizing spending, spotting a subscription you forgot, drafting a budget: those are fine jobs for a tool, and the data involved is low-stakes. The line I would draw is at anything that can move money, and at anything involving a joint account where the other person did not consent to their transactions being uploaded.

Convenience is real. So is the difference between a tool that answers you and a professional who is accountable to you.

Read the full article at MarketWatch →

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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