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What a federal trustee learned about why deals fail

By Donna Cangelosi · February 15, 2026

Deals fail for a small number of recurring reasons: no credible exit, collateral valued optimistically, and structures that leave no room for the unforeseen. The judgment that unwinds those situations after the fact is the same judgment that keeps a disciplined portfolio out of them.

Two decades in hard money, secured asset lending, and complex real estate workouts teach you to read a deal backward — from the failure point to the present.

The failure patterns repeat. A collateral value that only holds in an optimistic market. An exit that depends on a single buyer, a single refinance, or a single tenant. A structure with no slack for the unforeseeable. Each one is invisible in a good quarter and decisive in a bad one.

Disciplined underwriting is mostly the refusal to ignore those patterns when a deal is attractive in every other way — and the willingness to pass when the answer to “how does this end?” isn't convincing.

Underwriting that begins with “how does this end?” — and funds only deals with a real answer — is the practical application of Rule One: don't lose money.

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