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How I Invest with David Weisburd

How I Invest with David Weisburd

E375: Why Tax Alpha Could Matter More Than Investment Returns

How I Invest with David Weisburd · May 22, 2026 · 47:18

0:0047:18

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What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself?

In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-short tax-loss harvesting strategies evolved from niche institutional products into mainstream planning tools, why tracking error is often misunderstood, and how sophisticated investors think about balancing risk, leverage, and after-tax returns. We also explore trader funds, operational risk, and why tax management may matter more than active management for many investors.

Episodes: How I Invest with David Weisburd

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