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.

Highlights:

Why tax alpha can matter more than active management returns
How long-short portfolios create recurring tax-loss harvesting opportunities
The hidden risks behind aggressive tax-loss harvesting strategies
Why tracking error is often a feature, not a flaw
The operational complexity most investors underestimate
How trader funds generate ordinary losses
Why the best tax strategies are tied to assets investors already want to own
The difference between tax planning and “the tax tail wagging the dog”

Guest Bio:

Brent Sullivan is an independent tax analyst, software developer, and writer focused on tax-aware investing and portfolio construction. He publishes widely followed research on tax alpha, long-short investing, and advanced wealth management strategies through his platform Tax Alpha Insider. Brent specializes in analyzing the mechanics, risks, and implementation details behind sophisticated tax planning strategies used by advisors, family offices, and institutional investors.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Brent Sullivan:

LinkedIn:https://www.linkedin.com/in/brntsllvn/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Tax Alpha Became the “Boring” Edge Investors Miss (4:03) The Strategy Making Tax Loss Harvesting Explode (7:03) Where These Massive Tax Losses Actually Come From (12:28) The Biggest Players in Tax Loss Harvesting 3.0 (14:36) The Hard Part No One Talks About: Unwinding the Trade (19:39) Why Some Families Never Unwind These Strategies (23:12) The Hedge Fund Tax Strategy Quietly Gaining Momentum (29:15) How Tax Alpha Strategies Can Fail (36:54) Why Tracking Error Isn’t Always a Bad Thing (43:11) Why He Wishes He Went Independent Much Earlier