Simply Money presented by Allworth Financial

By Simply Money

June 5, 2026

On this episode of Simply Money presented by Allworth Financial, Bob and Brian put AI to the test, asking ChatGPT some of the most common financial planning questions—from Roth conversions and Social Security timing to concentrated stock positions and paying off a low-rate mortgage. They break down where artificial intelligence gets it right, where it falls short, and why context, personalization, and human judgment still matter when making major financial decisions.

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This story originally appeared in Simply Money

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