How to Diversify Concentrated Stock Without a Big Tax Bill

A strong market can create a new problem. A single stock or ETF grows to represent a large portion of your net worth. Now you face a difficult tradeoff: diversify and trigger a large tax bill, or hold the position and accept concentrated risk. In this episode, Tyler Emrick, CFP®, CFA®, walks through practical strategies for managing concentrated stock positions in a tax-efficient way. You will learn: How a Section 351 exchange into an ETF can provide diversification while deferring capital gains How tax-aware long-short strategies can help create ongoing tax offsets while gradually reducing a concentrated position When Net Unrealized Appreciation may apply to company stock inside a 401k How donor-advised funds and charitable planning can reduce capital gains on appreciated shares Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals. Our website: Phone: 855.TWD.PLAN Contact our team: Check out our other no-cost financial resources here: Watch the show now on YouTube:

You can listen to How to Diversify Concentrated Stock Without a Big Tax Bill online on Radio and Podcast. Open the player on this page to stream the available audio.

How to Diversify Concentrated Stock Without a Big Tax Bill is an episode from Retire Smarter by Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®.

This episode is 18:43 long.

This episode was published on Mar 12, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Retire Smarter when more episodes are available from the podcast feed.