E316: How Family Offices Design Portfolios for 30-Year Outcomes
How I Invest with David Weisburd
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
David Weisburd
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E316: How Family Offices Design Portfolios for 30-Year Outcomes

E316 • Mar 3, 2026 • 29 mins

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 people systematically underestimate how hard success actually is
  • The real meaning behind the 10X Rule
  • Quantity vs. quality — why reps create excellence
  • How omnipresence builds brand power
  • The psychology of follow-up and rejection in sales
  • Raising over $2B directly from retail investors
  • Why retail capital can be more powerful than institutional money
  • The real estate + Bitcoin hybrid strategy
  • Illiquidity as an investment advantage
  • Tokenization vs. going public
  • Lessons from addiction, ego, and resilience
  • Why exceptional performance requires extreme repetition

Guest Bio:

Grant Cardone is the CEO of Cardone Capital, a private real estate investment firm managing over $5 billion in assets. He is the author of eight business books, creator of thirteen best-selling business programs, and CEO of seven privately held companies generating approximately $750 million in annual revenue. Over the past three decades, Grant has advised companies on sales expansion, profitability improvement, and operational scaling through disruptive marketing and training systems.

Recognized by Forbes as one of the top social media business influencers in the world, Grant built a global brand by embracing omnipresence, repetition, and relentless follow-up. Through Cardone Capital, he has raised billions from retail investors and continues to innovate with new financial structures, including real estate and Bitcoin hybrid vehicles and tokenized asset strategies.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].

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 Grant Cardone:

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

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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