Episode 59
Family Property Tax Traps, I Bonds vs. Treasury Ladders, and Rethinking the Prenup with Aaron Thomas
June 1st, 2026
40 mins 33 secs
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About this Episode
A couple owns three properties across two states and has been letting their adult children and grandchildren use them freely. Their CPA recently raised concerns about imputed rental income and gift tax. Stephan walks through where the real risk actually sits, why personal use among family typically doesn't trigger imputed income rules, and when the picture genuinely changes — namely, when a property is also being rented commercially. The bigger takeaway may be that it's time for a second opinion.
Next, a listener sold a business eighteen months ago and is sitting on twelve million in cash split between a high-yield savings account and a money market fund. With a two to five year horizon, is there a real case for Series I bonds, a Treasury ladder, or both? Stephan addresses the I bond purchase limits, why they can't meaningfully move the needle at this scale, and the tax efficiency case for direct Treasuries versus money market funds. He also raises the more important question hiding underneath: how much of that cash should actually be sitting on the sidelines at all.
Then in From the Field, Stephan sits down with Aaron Thomas, a Harvard Law graduate, three-time winner of Atlanta's Best Divorce Attorney, founder of Prenups.com, and author of the Amazon bestseller The Prenup Prescription. Aaron has represented more than a thousand clients in high-stakes family law cases. Together they reframe prenuptial agreements as a foundation for financial clarity rather than a defensive measure, walk through the mine, yours, and ours framework, explore how to approach the conversation without leading with the word prenup, and discuss how families with generational wealth can protect assets built over decades while still honoring the full partnership of marriage.
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