Show Notes
My guest this week, Jeremy Roll, is a full-time professional passive investor with more than two decades of experience allocating capital across multiple real estate cycles. He is relentlessly data-driven, deeply immersed in macro and capital markets, and unapologetically conservative in how he thinks about risk.
That combination matters right now.
Jeremy is not trying to predict the next rate cut or headline shift. He is focused on something far more useful: where we actually are in the cycle, which assumptions quietly failed in 2025, and why capital remains sidelined despite constant talk of opportunity. His view of the market heading into 2026 is sober, unsentimental, and grounded in how cycles really work.
The overarching thesis of our conversation is simple but uncomfortable: predictability broke, patience was rewarded, and many investors learned the wrong lesson.
We discuss questions that serious investors and sponsors should be asking themselves now, including: Why did "survive till 25" fail so completely? Why have interest rates stayed higher than most expected? If there is so much capital on the sidelines, why isn't it moving? Why hasn't price discovery fully happened yet? Where does real opportunity actually come from in a slow-moving reset? What was the real mistake behind floating-rate, value-add deals? How should investors evaluate sponsors after the last three years? Jeremy also draws a sharp distinction between heavy value-add investors, who are already active, and value-oriented investors, who face the very real risk of being too early. He frames today as closer to late 2009 or 2010 than 2011: the light is visible, but the reset is not complete.
This is not a conversation about hype, shortcuts, or timing the exact bottom. It is about discipline, incentives, and understanding why doing nothing for long stretches is sometimes the most rational strategy.
If you invest in commercial real estate or allocate capital to those who do, this episode will help you think more clearly about what actually matters heading into 2026.
*** In this series, I cut through the noise to examine how shifting macroeconomic forces and rising geopolitical risk are reshaping real estate investing.
With insights from economists, academics, and seasoned professionals, this show helps investors respond to market uncertainty with clarity, discipline, and a focus on downside protection.
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