The 351 Conversion Breakdown, a 400-Acre Farm Legacy Fight, and Patterns After Seven Years

On Monday, September 28, the IRS released Revenue Ruling 2026-20 and Notice 2026-62, treating a widely used Section 351 ETF conversion as a taxable exchange. A listener who ran one earlier this year to diversify a $4.2 million concentrated position wants to know what to expect. Stephan walks through why these structures were being sold as a free lunch, what the ruling changed, and the conversation to have with your CPA.
A 400-acre family farm in Pennsylvania has been in one family since 1912. The parents, in their late 70s, have never discussed what happens to it. One sibling wants to keep farming, one wants to sell her share, and the listener in Chicago is caught in the middle. Stephan unpacks why farmland estates are their own category, the ways to equalize, and why the hardest conversation is also the one that cannot wait.
A listener wrote in after reading the Q3 Advisor Desk letter https://scholarfinancialadvising.com/newsletter-2026-q3/ and asked what other patterns Scholar has seen after seven years. Stephan adds a handful: the $10 million complexity trap, the million-dollar W-2 tax trap, the retiring-early myth, inconsistent travel spending, the “no one rents out their vacation home” rule, and why grandkids ruin financial plans.

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Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives and risk tolerance. Thanks for listening!