Building a Family Insurance Empire: Risk, Faith, and 50 Years of Entrepreneurship

In this special in-person episode of Risk & Resolve, Ben Conner and Todd Hufford sit down with Jim Conner—second-generation insurance entrepreneur and former president of Conner Insurance—to unpack five decades of risk-taking, family business, faith-driven leadership, and hard-earned lessons. From buying the agency at age 22 with a $50,000 note to navigating acquisitions, expansion failures, carrier relationships, and generational transition, Jim shares what it really takes to build—and sustain—a family enterprise. This is a candid conversation about ownership, conviction, legacy, and why burning the ships might be the only way forward.Main Talking Points:The 1973 decision: four brothers buying the family agency with a $50,000 bank noteLessons from Jim’s father: war survivor, project-driven entrepreneur, relentless relationship builderWhy “burning the ships” shaped their mindset toward business survivalGrowing from $150K in revenue to multi-location expansion across IndianaThe risks and realities of managing satellite offices before technologyNegotiating underwriting authority and building carrier leverage (the Maryland story)Why autonomy without accountability exposed the limits of expansionFlatline years, hard cash-flow seasons, and bearing leadership pressure aloneIntegrating faith and business through CBMC, mentorship, and personal convictionThe challenges—and necessity—of generational successionWhy ownership changes everythingLegacy thinking: shifting from building a company to investing in grandchildren