Most investors spend their time chasing returns. Institutional investors focus on protecting the downside—and that difference explains exactly why today’s market looks the way it does.

Rich sits down with John Azar and Francisco Herrera to unpack what really happened during the euphoric run of 2021–2022, how undisciplined underwriting and risky debt structures created today’s wave of distress, and why many so-called “broken deals” aren’t asset problems at all—they’re capital structure problems.

The conversation cuts through the noise around cap rates, rent growth, and interest rates to highlight what actually matters: buying right, underwriting conservatively, and understanding who the buyer will be years before you ever close on a deal. John and Francisco share how institutional investors think about risk, why hope is not a strategy, and how overleveraging turned strong assets into liabilities almost overnight.

Rich also dives into why relationships outperform deal-chasing, why saying “no” for long stretches can be a competitive advantage, and how disciplined operators stay durable through every phase of the cycle.

This is a clear-eyed, no-hype discussion on capital preservation, real underwriting, and what it takes to invest like an institution when the market stops being forgiving.

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Episode 491: Changing the World Through Conversation W/ Nicky Gumbel (Alpha Course)