Is a Section 351 Exchange a Tax Loophole — or a Legitimate Planning Tool? episode artwork

EPISODE · Jul 31, 2026 · 26 MIN

Is a Section 351 Exchange a Tax Loophole — or a Legitimate Planning Tool?

from The Investor Coaching Show with Paul Winkler · host The Investor Coaching Show

More investors are starting to ask about Section 351 exchanges, a little-known part of the tax code that can allow someone to move appreciated stocks into an ETF without immediately paying capital gains taxes. Evan breaks down how the strategy works, who may be able to use it, and why it probably won’t come up in most investors’ financial plans. He also looks at why Section 351 exchanges are getting more attention from regulators and whether they are a smart planning strategy or simply a tax loophole.  Later in the episode, Evan talks about taxes on student financial aid and what families should know about Trump Accounts.   Want to cut through the myths about retirement income and learn evidence-based strategies backed by over a century of data? Download our free Retirement Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.   This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information. Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser. 

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Is a Section 351 Exchange a Tax Loophole — or a Legitimate Planning Tool?

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