John Trammell, a seasoned institutional investor leading investments for the Episcopal Diocese of New York, dives into the changing landscape of endowment investing. He discusses why top universities are offloading assets in secondary markets and how this helps manage underperforming investments. Trammell argues that a concentration strategy has fueled great fortunes, while highlighting the critical role of liquidity today. He also examines Bitcoin's emerging role in portfolios and the importance of building conviction to navigate market challenges.
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insights INSIGHT
Why Endowments Sell Secondaries
Top endowments are selling assets in secondaries to increase liquidity amid funding shortfalls.
They often unload less favored private equity investments while retaining key public equities.
insights INSIGHT
Universities' Liquidity Pressures
Student enrollment drop and government grant cuts drive immediate liquidity needs for universities.
Possible tax increases add further financial planning complexities for endowments.
insights INSIGHT
Reassessing Private Equity Exposure
Universities likely overexposed to private equity with some poor performers.
Current market and funding pressures have prompted re-examination and sales of such holdings.
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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
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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.
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.
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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
(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
How I Invest with David Weisburd