Skip to main content

«  View All Posts

Do Captives Only Work for Large Businesses?

April 12th, 2026

1 min read

By Warren Cleveland

Hero Image Do Captives Only Work for Large Businesses
Do Captives Only Work for Large Businesses?
2:10

My Client Has Heard the Word Captive Before, But Thinks It's Only for Huge Companies. How Do I Correct That Without It Becoming a Lecture?

Your client isn't wrong about where captives came from. For a long time, captives were exclusively a Fortune 500 tool. Large corporations with deep balance sheets, internal risk management teams, and millions in premiums. That was the landscape for decades. So when your client says that's not us, they're working from information that was once accurate.

What's changed is the structure. Group captives changed everything.

Here's how you explain it without turning it into a presentation. You don't correct them directly. You just reframe it.

Something like this: you're right that captives used to be for the big guys. What's different now is that group captives let businesses pool together, which means the threshold is a fraction of what it used to be. If you're spending $250,000 or more on workers comp, general liability, and auto combined, you're in the conversation. That's it.

Then stop talking. Let them do the math. Most business owners spending at that level know exactly what they're paying, and the moment they realize they qualify, the whole dynamic of the conversation shifts. They went from "not my world" to "tell me more" in about thirty seconds.

What you don't want to do is launch into a full explanation of how group captives work, how risk is pooled, how the fronting carrier operates, and what the difference is between an A/B structure and a quota share. None of that. That's the lecture version. You've lost them by slide two.

The job in this conversation is simple. Move them from that's not for us to I didn't know I might qualify. That's one sentence and a question. Everything else comes after.

We've got resources that make this easy. A simple one-pager, a calculator that shows the numbers in five minutes. You don't need to explain how captives work to get your client curious about them. You just need to show them the door.

We'll help you walk them through it from there.

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