Today’s guests are Wes Gray, Co-CIO of Alpha Architect, and Brent Sullivan, Editor of Tax Alpha Insider, which is the only publication focused on taxable portfolio strategy.

In today’s episode, Brent Sullivan and Wes Gray discuss how to handle concentrated stock positions. They explore the complexities around 351 ETF exchanges, what investors need to know when participating to adhere to tax laws. To close, they examine the rise of tax-managed long-short strategies and how AI may transform tax planning and portfolio management.

(0:00) Starts

(1:18) Brent Sullivan's background

(3:36) Handling concentrated stock positions

(7:32) 351 to ETF conversions

(14:49) Regulatory scrutiny & IRS enforcement

(27:39) Rebalancing, tax implications and practical advisor advice

(34:09) Future ETF seeding predictions

(39:01) Comparing ETF seeding and portfolio consolidation strategies

(45:48) Long short strategies

(52:23) Brent Sullivan's book and conference

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Past guests include Ed Thorp, Richard Thaler, Jeremy Grantham, Joel Greenblatt, Campbell Harvey, Ivy Zelman, Kathryn Kaminski, Jason Calacanis, Whitney Baker, Aswath Damodaran, Howard Marks, Tom Barton, and many more.

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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

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