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

The Meb Faber Show - Better Investing

The Idea Farm

Management, Investing, Business

4.8 • 978 Ratings

🗓️ 13 March 2026

⏱️ 58 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 Feedback@TheMebFaberShow.com ----- 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). Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Welcome to the Medfavor show, where the focus is on helping you grow and preserve your wealth.
0:10.8	Join us as we discuss the craft of investing and uncover new and profitable ideas, all to help you grow wealthier and wiser.
0:16.9	Better investing starts here.
0:19.5	Metfavor is the co-founder and chief investment officer at Cambria Investment Management. Did it industry regulations, he will not discuss any of Cambria's funds on this podcast. All opinions expressed by podcast participants are solely their own opinions and do not reflect the opinion of Cambria Investment Management or its affiliates. For more information, visit camriainvestments.com. Now, are all the traitors present? Let's get started, shall we?
0:38.3	From rags to riches.
0:39.6	I'm so sick of this.
0:40.9	Working like a dog and being treated worse.
0:43.0	Yorkshire to New York.
0:44.6	Poor climbers, you and me.
0:46.2	A life dedicated to revenge.
0:48.2	Let's make this an occasion to remember.
0:50.7	A woman a substance on Channel 4 starts tonight at 9.
0:54.1	Welcome back, everybody. Today, your favorite topic. We're talking taxes. We got the chief
0:59.9	tax nerd. You guys know him, so no real introduction. West Gray, he must manage 20, 30, 40 billion
1:06.6	at this point, including one fund, over 10 billion, always with a focus on taxes.
1:12.3	He's been on this podcast, probably more than anybody.
1:14.4	But we got a new guest today, Brent Sullivan, who's an independent tax analyst.
1:20.3	He's the editor of Tax Alpha Insider, which I subscribe to, which to my knowledge is the only
1:26.1	publication focused on taxable portfolio
1:29.1	strategy.
1:30.4	And the main meme tax generator, Brent, Wes, welcome the show.
1:36.1	I'm honored to be here.
	...

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