Why Jory Caulkins Invests in Moats, Not Just Multiples
Jory Caulkins of Enduring Companies shares how trust, moats, and downside protection drive his investment decisions as an independent sponsor.
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.
More recent episodes
Grew EV 10x in 5 Years
Ben Rudman knew he wanted to work in food before he knew what investment banking was. His first independent sponsor deal, Western Smokehouse Partners, started with ~60 employees in 2018. By the time it sold 4.5 years later, it had almost 700 employees across 4 facilities and enterprise value had grown ~10x.
On the Ground at McGuireWoods 2026
Recorded from McGuireWoods in Dallas after Day 1, Niklas, Max & Will compare notes from the conference floor. Last year had ~2,000 attendees and this year felt bigger. The Minds team had ~30-40 meetings, found 3-5 qualified deal leads & ~6 prospective podcast guests. The day before, Minds hosted its annual Investor Day with 70+ RSVPs from 142 LPs and 8 portfolio sponsors attending.
32x MOIC After 100 Investors Said No
Since Kevin Ramsier's last appearance on this podcast, his firm, Sier Capital, has closed a new infrastructure platform (where Minds Capital is an investor) and exited another business that generated a 32x MOIC over a 7-year hold. The same business started with 95% customer concentration and nearly 100 investors said no.