E176: Beyond Harvard: The Financial Crisis Endowments are Facing

How I Invest with David Weisburd

John Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing. We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional portfolios, and why concentration—not diversification—created most of the great fortunes. This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today.

Highlights:

• Why top endowments are dumping assets in the secondary market
• How secondaries give institutions a way to clean up bad manager exposure
• The real reasons endowments need liquidity today
• Why some schools are now selling private equity... to themselves
• What a collateralized fund obligation (CFO) actually is
• Why John believes we’re past the Swensen model—and what’s next
• The truth about diversification (and when it fails you)
• How to build conviction to survive the toughest market moments
• Why cash is no longer a drag on portfolios
• How to cultivate a “prepared mind” for the next black swan event

-- Guest Bio: John Trammell is a seasoned institutional investor who has managed assets across public and private markets for decades. He currently leads investments for the Episcopal Diocese of New York and has previously managed portfolios for prominent family offices and foundations. John is known for his thoughtful, experience-driven approach to asset allocation, governance, and long-term investment strategy—and for his ability to distill complex ideas into timeless lessons.

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-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Trammell :https://www.linkedin.com/in/john-trammell-258723/

Links: Episcopal Diocese of New York: https://dioceseny.org/

-- Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(0:00) Episode preview (3:11) Liquidity and portfolio construction in university endowments (5:26) Pros and cons of secondary fund investments (7:09) Secondary market investment mistakes by institutional investors (9:20) Asset quality tiers in secondary investing (10:04) Execution of collateralized fund obligations (13:02) Investment governance and alumni contributions (19:54) Swenson model evolution and diversification strategies (25:14) Portfolio management: Concentration vs diversification (28:06) Assessing portfolio diversification strategies (30:15) Bitcoin's role in portfolio diversification (32:27) Cash and emotional challenges in investing (35:18) Tactical strategies during market downturns (36:23) Conviction's importance in investment decisions (39:06) Institutional views on Bitcoin allocation (51:13) Educating stakeholders on liquidity management (54:06) The importance of investment education (55:38) Embracing a prepared mind in investing (57:43) Closing remarks