E370: What Taxable Investors Still Get Wrong About Returns
What if the biggest source of alpha today isn’t stock picking—but structuring portfolios more intelligently after taxes? In this episode, I sit down with Shang to discuss why tax alpha is becoming one of the most important themes in wealth and asset management. Shang breaks down how long-short tax-aware strategies work, why manager selection matters more than most investors realize, and how investors should think about tracking error, leverage, and operational risk. We also explore portable alpha, hedge fund tax structures, and why the explosion of tax-focused products may create as many risks as opportunities.
Highlights:
- Why after-tax returns matter more than pre-tax performance
- The hidden importance of manager selection in tax-loss harvesting
- How tracking error creates both opportunity and risk
- Why volatility can improve tax-loss harvesting outcomes
- The difference between economic substance and “tax-only” strategies
- How portable alpha changes portfolio construction
- Why institutional borrowing rates are now accessible to individuals
- The risk of “tax tail wagging the dog” in investment decisions
Guest Bio:
Shang is a fintech and investment executive with deep experience across wealth management, ETFs, and institutional portfolio solutions. He previously held senior roles at Goldman Sachs, PIMCO, and J.P. Morgan, and helped scale some of the fastest-growing ETF platforms in the industry, including Simplify Asset Management and Tema ETFs. Shang focuses on developing innovative investment solutions for advisors, family offices, and individual investors, with expertise spanning tax-aware investing, derivatives, and portfolio construction.
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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 Shang Chou:
LinkedIn:https://www.linkedin.com/in/shangchou/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
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.
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Transcript
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