AI can crunch a portfolio, harvest losses, and explain an investment concept in seconds. But can it stop a nervous investor from selling at exactly the wrong moment—or understand the life behind the spreadsheet? Tom and Don test the robot-advisor promise, even asking ChatGPT to weigh in. The verdict is a useful division of labor: let technology handle repeatable mechanics, while human judgment, fiduciary responsibility, and behavior coaching remain hard to automate. Then the questions get w...