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What’s the Most Important Thing to Understand About Captives?

April 14th, 2026

1 min read

By Warren Cleveland

Hero image What’s the Most Important Thing to Understand About Captives
What’s the Most Important Thing to Understand About Captives?
2:05

I keep hearing about captives, but honestly, I have no idea how they work or where to even begin. What's the most important thing for me to Understand First?

You don't need to understand everything. That's the first thing I want you to hear, because the captive industry has spent years making this feel more complicated than it is. The complexity serves them. It keeps agents dependent. It keeps agents quiet. And it keeps agents from having conversations that would make them less dependent on carriers who don't particularly care about their relationship with their clients.

Here's what actually matters to understand first.

A captive is an insurance company owned by the businesses it insures. Instead of paying premiums to a carrier and watching every dollar disappear, the business funds its own insurance company. When losses are low and the business performs well, the money they paid in comes back to them as underwriting profit. They own the company. They get the result.

That's it. That's the core idea. Everything else, the structure, the different types, the collateral, the fronting carrier, the actuarial process, all of it builds on that one concept. You don't need to understand all of it before you start having conversations. You just need to understand it well enough to open a door.

Here's how simple the first conversation can be. You've been paying insurance premiums for years. In that time, how much has ever come back to you? The answer is zero. What if there was a structure where your performance actually determined what you kept? That question doesn't require you to know what a domicile is. It doesn't require you to explain reinsurance. It just opens a door.

The agents who wait until they feel like experts before they start talking about captives are the ones whose best clients get the conversation from someone else first. You don't need to be the expert. You need to be the person who started the conversation.

Get in. Learn as you go. We'll back you up on every question you can't answer.

It's always your client. Never ours.

Warren Cleveland

Warren Cleveland launched Captive Coalition after firsthand experience as an independent agency owner revealed a major gap in the market: agents lacked access to the knowledge and resources needed to compete with large brokerages offering captive insurance solutions. Warren brings over a decade of insurance leadership—including as President of ReNu Insurance Group—and a career that spans aviation, real estate, and commercial insurance. His mission is to ensure agents stay in control, keep their best clients, and confidently lead with captives. Warren Cleveland, ACI, CIC, AAI