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AI vs. robo advisers: How they stack up against each other — and human financial advisers

Genna Contino at MarketWatch compared AI tools, robo advisers and human financial planners, and asked where each one belongs. The line from our conversation that stuck with readers: once you get to a certain point, you traditionally outgrow a robo adviser.

Robo tools are good at what they were built for. Automated rebalancing. Low-cost index exposure. A single account with a single, simple goal. That is not a knock on them. It is a description of what they are for, and for a 28-year-old with a Roth IRA and a target date, it is often the right answer.

Complexity does not stay simple, though. A house sale. A parent's death. A business exit. An inherited IRA that comes with a ten-year distribution clock most people never hear about until it is already running. Those are not inputs. They are decisions with tax consequences and emotions attached.

I told MarketWatch this directly: I do not want to have to explain to an AI chatbot that my wife just died. Some conversations need a person who can sit in the moment with you, not process it as data.

The real question was never AI versus human. It is whether the tool you are using now can flex when your life gets more complicated than the app was built for.

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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