The Meb Faber Show
The Meb Faber Show
Welcome to The Meb Faber Show, where the focus is on helping you grow and preserve your wealth. Join us as we discuss the craft of investing and uncover new and profitable ideas, all to help you grow wealthier and wiser. Better investing starts here.
Meb Faber
PodcastAI
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The Tax Alpha Arms Race (w/ Wes Gray & Brent Sullivan) | #622

Mar 13, 2026 • 57 mins

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.

Key Points

  • Tax-managed long-short strategies offer significant tax advantages and can generate consistent losses for tax purposes, making them popular despite potential higher costs and added complexity.
  • The ETF seeding strategy using section 351 is gaining traction, with predictions of more widespread adoption, particularly among large asset managers looking to streamline and lower costs for diversified portfolios.
  • The IRS's scrutiny of potential tax-free diversification abuses underscores the importance of adhering to the intent of tax laws and maintaining economic substance in transactions to avoid regulatory risk.
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