Episode Details

In a wild ride through NYC real estate, Harry Macklowe’s “midnight demolition” in 1985—torn down four buildings overnight without permits or utilities shut off—became legendary. It’s the ultimate “ask for forgiveness, not permission” play, echoing tactics seen in tech and beyond. Macklowe’s rollercoaster career reveals how developers thrive on risk, often making money not just from sales but from fees and performance bonuses called “promotes.” It’s a high-stakes game where obstacles are launchpads, and a good joke—or a Catskills one—might just be the secret sauce.

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