February 26, 2026

E313: Why the Endowment Model Doesn’t Work for Taxable Investors

32 minutes

Why does applying institutional investing frameworks often fail for taxable investors and families?

David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction—and why clarity of objectives is the real edge.

Highlights:

Why institutional investing frameworks break down for taxable investors

The rise of the taxable private-market allocator

Asset allocation vs. asset location—and the cost of getting it wrong

How taxes can erode 30–40% of gross returns

Tax-efficient structures in infrastructure and private markets

Applying the endowment model to families: what’s usually missing

The three hardest problems: sizing, sourcing, and pacing

Denominator and numerator effects in volatile markets

Continuation vehicles, co-invests, and the evolution of fee structures

Why governance and investment policy matter more than tactics

Ranges vs. point targets in asset allocation

Managing capital calls without forcing bad sales

Why ad hoc investing quietly destroys portfolios

Key-man risk, manager “genius,” and process vs. discretion

Guest Bio:

Aneet Deshpande is a senior investment professional and allocator with deep experience advising institutions and private clients on portfolio construction, private markets, and governance. His work focuses on adapting institutional frameworks—such as the endowment model—to the realities of taxable investors, with an emphasis on tax efficiency, pacing, liquidity management, and long-term wealth preservation across generations.

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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.

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Stay Connected with Aneet Deshpande:

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

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.

(0:00) Introduction

(1:00) Taxable Investors and Private Market Investments

(3:15) Endowment Model Challenges and Fee Trends in Alternatives

(9:17) Managing Liabilities and Understanding the Denominator Effect

(13:14) Governance and Best Practices in Wealth Preservation

(17:48) Addressing Governance Issues and the Perils of Random Investments

(21:37) Co-investment Trends and Algorithmic Approaches

(23:00) Navigating SPV Layers and Investment Fees

(24:05) Timeless Investment Principles and Intellectual Honesty

(27:33) Unique Traits of Successful Investors

(29:33) Analyzing Investment Manager Strengths and Strategic Planning

(32:21) Closing remarks

...more

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By David Weisburd

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