In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.

Unlike equity investors hunting for uncapped upside, debt lenders have a fixed return and are intolerant to losing principal. This forces them to be paranoid about downside risk and worst-case scenarios. Their diligence process is often more thorough and thoughtful, providing a different and rigorous lens on the business.

To truly understand a potential financial partner, the Chomps team went beyond the supplied references. They found a founder whose company didn't succeed under the PE firm's investment. His positive review of the partner's character, despite the negative outcome, provided the most powerful signal of trust.

The most imprudent lending decisions occur during economic booms. Widespread optimism, complacency, and fear of missing out cause investors to lower their standards and overlook risks, sowing the seeds for future failures that are only revealed in a downturn.

David Cohen of Techstars advises founders to request references from a VC's failed investments. This reveals how an investor behaves during difficult times, providing a more honest assessment of their character and support level than speaking only with successful founders.

Despite headlines blaming private credit for failures like First Brands, the vast majority (over 95%) of the exposure lies with banks and in the liquid credit markets. This narrative overlooks the structural advantages and deeper diligence inherent in private deals.

To truly understand an investment's resilience, analyze its performance over a 20-year span, paying close attention to how it navigated major downturns like the dot-com bubble and the 2008 financial crisis. This deep historical analysis provides a clearer picture of stability than recent performance alone.

After working out 22 distressed joint ventures during the GFC, the key lesson was that partner quality dictates outcomes more than the deal itself. When things go wrong, good partners collaborate to find solutions, while bad partners create conflict, making even a good deal untenable.

A rising tide lifts all boats. The true test of a founder partnership emerges during downturns. Diligence should focus on teasing out traits like adaptability, humility, and accountability, which predict how a founder will react when plans inevitably go awry.