In this episode of The Edge of Risk podcast by IRMI, host Joel Appelbaum welcomes Courtney Boles, director of operations at Management Services International (MSI), one of the largest captive managers in North Carolina. Courtney brings her unique perspective on how small businesses can harness organizational alignment to maximize the success of their captive insurance programs. Drawing on her experience in both commercial insurance and captive management, Courtney discusses the importance of identifying internal champions, demystifying the captive formation process, and addressing common skepticism among business owners and their advisers. She highlights the value of communication, education, and cultural buy-in as cornerstones of long-term alignment. The conversation also explores real-world examples of successful captives, strategies for balancing emerging risks with conservative growth, and the role of innovation—from parametric solutions to artificial intelligence-driven tools—in shaping the future of small-business captives.