Why Jory Caulkins Invests in Moats, Not Just Multiples

Dallas-based Jory Caulkins is a Stanford GSB / Bain Capital alum with extensive experience as a serial entrepreneur, dealmaker, and operator. His firm, Enduring Companies, owns four portfolio companies, including two as the lead sponsor.

Jory discusses “trust” in great detail. He outlines why it is so important and suggests a series of tactical ways to build trust with sellers, investors, and other stakeholders. He explains the “say-do” ratio, likens trust to a bank account, and advocates for content marketing as a trust-builder.

Jory shares that his firm didn’t close a deal in 2024, despite reviewing 1,400 opportunities. Is it them or is it the market? We don’t know, but Jory takes us through how he tries to stay disciplined and only pursues opportunities that are both a good fit for him and a good business in general.

According to Jory, deal diligence can boil down to three main criteria:

• Moat: Can the business maintain and grow market share indefinitely?
• Longevity. Is there a risk the business may be disrupted?
• Asymmetry. Is the downside protected? Is there upside potential?

Listen for Jory’s insights on investment philosophy, industry trends, and business-relationship-building advice.