Last Updated on: September 4, 2025

The Captive Conversation Part 3, Shoptalk Episode #191

The captive insurance
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In the third installment of our four-part series on Power Producers Shop Talk, host David Carothers and Warren Cleveland of Captive Coalition break down the fundamentals of captive insurance. This episode is designed to give agents the foundational knowledge needed to confidently discuss captives with clients. Warren demystifies the core concept, explains the different models, and provides a critical warning against the misused 831(b) tax election. They also tackle common misconceptions about size and risk, and outline the ideal prospect profile, emphasizing that commitment to risk management is non-negotiable for success.

Key Highlights:

Demystifying Captive Models

Warren Cleveland explains that a captive is simply an insurance company owned by its members, designed to let them keep the underwriting profit. He clarifies the primary models agents will encounter: Group Captives (where multiple businesses pool risk), Single-Parent Captives (for very large companies insuring their own risk), and Cell Captives (an efficient structure where a business “rents” a legally separate cell from a larger captive).

A Critical Warning on the 831(b) Tax Election

A significant portion of the episode is dedicated to a crucial warning: stay away from the 831(b) tax election. Warren stresses that this is a tax classification, not a type of captive, and has been widely abused by promoters as a tax shelter. The IRS is aggressively and successfully prosecuting these cases, and agents should advise clients that any true captive must be about insurance first, not a tax play.

Busting Common Agent Misconceptions

The conversation addresses the myths that stop agents from exploring captives. They debunk the “you’re not big enough” fallacy, clarifying that businesses spending $250,000 or more can be ideal candidates. They also tackle the “it’s too risky” concern, explaining that an agent’s job is to help the client understand and quantify the risk, not avoid the conversation entirely.

The Anatomy of an Ideal Captive Prospect

Warren outlines the three pillars of a perfect captive candidate. First, they must have sufficient premium spend. Second, the business owner must be frustrated with the traditional market and willing to take on calculated risk. Third, and most importantly, they must have a deep-seated belief that investing in risk management, safety, and training will directly improve their financial outcomes. A captive exposes risk management flaws; it doesn’t fix them.

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Kyle Houck

Captive

Captives Have Moved Downstream: Why Middle-Market Producers Must Master the Conversation—Or Get Left Behind

For most of my 20-year career, captives felt like something reserved for the insurance elite—the jumbo accounts, the Fortune-level operations, the companies with multimillion-dollar manual premiums and entire departments dedicated to risk management. If you had asked me ten or fifteen years ago whether a $250,000 account was a legitimate captive candidate, I would’ve laughed. I thought captives were reserved for companies so complex and so large that the only rational way to insure them was to build an insurance company around their risk.

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