The Tax Alpha Arms Race (w/ Wes Gray & Brent Sullivan) | #622

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 ----- Follow Meb on X, LinkedIn and YouTube For detailed show notes, click here To learn more about our funds and follow us, subscribe to our mailing list or visit us at cambriainvestments.com ----- Follow The Idea Farm: X | LinkedIn | Instagram | TikTok ----- Interested in sponsoring the show? Email us at [email protected] ----- 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.  ----- Meb's invested in some awesome startups that have passed along discounts to our listeners. Check them out here!  ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).