Captives Uncovered with Warren Cleveland

Are you an independent insurance agent or agency leader looking for a smarter way to grow your business, retain more profit, and better serve your clients? In this episode, host Brent Kelly sits down with Warren Cleveland, CEO of Captive Coalition, to uncover the untapped potential of captive insurance.

Warren shares his entrepreneurial journey from aviation to insurance innovation—and explains why captives are becoming essential tools for agents who want more control, transparency, and long-term client relationships. You'll learn how to overcome misconceptions, embrace failure as growth, and understand the real financial impact of captives on your agency’s future.

Highlights Include: 00:00 Introduction to Captives and Insurance Leadership04:12 Understanding Captives: What They Are and Why They Matter10:42 The Unique Approach of Captive Coalition19:39 Challenges and Misconceptions in the Captive Insurance Space25:02 Success Stories and Empowering Agents33:17 Advice for the Younger Self: Embracing Failure39:18 Final Thoughts and Resources for Agents

Whether you’ve never heard of captives or you’re ready to take the next step, this conversation will shift how you think about risk, revenue, and relevance in today’s insurance world.

To learn more about Warren Cleveland and Captive Coalition visit their site at https://www.captivecoalition.com/.

To learn more about our programs for growth-minded agencies visit www.sitkins.com.