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White Coat Investor Podcast

White Coat Investor Podcast

WCI #489: Advanced Financial Planning Q&A for Physicians

Sep 17, 2026 · 1h 15m

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In this episode, Dr. Jim Dahle is joined by financial planner Dr. Tyler Scott to work through a wide range of advanced financial planning questions. They cover whether to open a single 529 account for multiple nieces and nephews or keep them separate, and why gifting appreciated shares to an adult child in a lower tax bracket can run afoul of decades-old IRS doctrines if the money comes back to the giver. Tyler walks through the legal reasoning behind assignment of income, substance over form, and step transaction doctrine, explaining exactly where these strategies cross the line. The conversation also covers upstream gifting to parents in hopes of a future step-up in basis, including the…