Retire Smarter with Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®
Retire Smarter with Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®
Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®
How to Rebalance a Highly Appreciated Portfolio Without Selling: The 351 Exchange Strategy
19 minutes Posted Jun 11, 2026 at 9:04 am.
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Many investors have highly appreciated stocks and ETFs they would like to diversify, simplify, or replace, but selling those investments can create a significant capital gains tax bill.
In this episode, Tyler Emrick, CFA®, CFP®, discusses the 351 Exchange Strategy, a little-known tax-efficient planning opportunity that may allow investors to exchange appreciated stocks and ETFs into a diversified ETF without first selling and realizing capital gains taxes.
Tyler covers:
What a 351 Exchange is and how it works
The difference between a 351 Exchange and a traditional exchange fund
Rules investors must satisfy before qualifying
Which assets qualify and which assets do not
ETF eligibility requirements
How highly appreciated ETF portfolios may be consolidated into a diversified ETF
How concentrated stock positions may fit into a 351 Exchange strategy
The potential benefits of reducing concentration risk without immediately triggering capital gains taxes
How 351 Exchanges compare to tax-aware long-short strategies and other tax-efficient diversification techniques
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