Episode Details

What if the easiest alpha in public markets isn’t stock picking… but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

Highlights:

• Why “long-term” means something different for asset owners vs. traders
• Lessons from Wellington, TIFF, and investing in emerging managers
• Why fund one through fund three often generate the most alpha
• Incentive alignment and GP capital commitments
• Structural edges inside single-family offices
• The three levers of value creation: security selection, asset allocation, structural alpha
• Tax drag in mutual funds vs. ETFs
• How ETFs preserve tax alpha through in-kind redemptions
• Tail-risk hedging inside an ETF vs. private hedge funds
• Avoiding the 10 worst days — and capturing the 10 best
• Designing portfolios to reduce maximum drawdown
• Why tax deferral may be the most sustainable form of alpha

Guest Bio:

Zach Wainwright founded Twin Oak ETF Company with a singular focus: delivering innovative, institutional-quality, tax-efficient solutions to high-net-worth clients. Throughout his career at firms such as Wellington Management and TIFF, and later within a single-family office, Zach observed that taxable investors were often underserved — losing significant performance to unnecessary tax drag despite strong investment selection.

At Twin Oak, Zach focuses on what he calls “structural alpha” — leveraging time horizon, tax efficiency, and thoughtful implementation to unlock portfolio potential. His approach blends institutional rigor with family-office pragmatism, creating ETF-based solutions that aim to preserve compounding, reduce drawdowns, and optimize after-tax outcomes for long-term investors.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? 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 Zach Wainwright:

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

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 ep