Writing · Capital / Finance / Investing
From $259M to $5.6M: How Cash Flow Vanished in Just 12 Months
The Office REIT That Ran Out of Time
Office Properties Income Trust is a snapshot of everything that can go wrong in real estate when optimism outruns math.
They bought too high.
They bought too much.
They borrowed too much.
They handed out too many distributions when the sun was shining.
They assumed refinancing or a sale would always be there.
Now, the tide is out. Cash is nearly gone. Debt maturities are stacking up like planes circling a runway with no fuel left to land. Occupancy keeps falling. Bankruptcy looms.
This is not just about one REIT. It’s the same pattern we’ve seen for a century:
• Florida land boom of the 1920s.
• Overbuilt office towers in the 1980s.
• Condo developers in 2007.
• Today’s wave of syndicators who promised the moon with floating-rate debt.
The characters change, but the script stays the same.
What lessons can we learn? They’re as old as finance itself:
Too much Debt turns timing risk into existential risk.
Reserves look unnecessary, until they’re oxygen.
GP Incentives drive outcomes—bad ones can kill faster than bad markets.
Yet people keep repeating the same mistakes. Why? Because success feels like skill when often it’s just timing. And timing feels controllable when it’s mostly luck. Michael Mauboussin captures this perfectly in “The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing.” It’s one of those books that changes how you see cycles, I know it did for me.
The market makes geniuses in one cycle and fools in the next.
In real estate, location matters. But timing matters more. And the clock never stops.
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