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What Do I Actually Need to Know to Start the Conversation?

April 12th, 2026

2 min read

By Warren Cleveland

Hero Image What Do I Actually Need to Know to Start the Conversation
What Do I Actually Need to Know to Start the Conversation?
2:42

I've Been Putting This Off for Two Years Because It Felt Too Complicated. What Do I Actually Need to Know to Start Having This Conversation.

Two years. And in that time, someone has almost certainly been circling your best accounts with a captive pitch. You just don't know about it yet.

Here's the thing about captives feeling too complicated. That feeling isn't about captives. It's about how the industry has always presented them. Agents sit through a 101 presentation full of risk transfer terminology, fund structures, actuarial tables, and sample member data that has nothing to do with their actual clients. By the end of it, they're more confused than when they started. That's not education. That's the industry making sure agents stay dependent on captive managers who want to control the information and control the relationship.

We built something different specifically because of that problem.

You don't need to be a captive expert to start having this conversation. You need to know three things.

First, who is a fit? A business spending $250,000 or more in combined premiums across workers comp, general liability, and auto, with clean losses, who is frustrated with the traditional market and willing to invest in their own performance. That's your profile. You can surface that in a short conversation without asking for a single document.

Second, how to open the door. Not pitch a captive. Not explain how it works. Just say, there's a strategy I've been looking into that I think is worth a conversation. I'm not saying it's right for you. I don't know yet. But based on what you've told me about your insurance spend and your claims history, I think we should look at it together. That's the whole first conversation.

Third, you don't have to have all the answers. You need a partner who does. That's what we're here for. You bring us the account, tell us what you know, and we'll tell you if it's worth pursuing. We'll give you the resources to back you up in front of your client. We'll coach you through the questions they'll ask. You don't show up as the captive expert. You show up as the advisor who was thinking about their business when nobody asked you to.

The agents who waited two years and then finally started are always glad they did. The ones who wait another two years are the ones who eventually get that phone call from a client who says, "Hey, someone just brought me a captive proposal, what do you know about this?"

That's not the call you want to be getting.

Start the conversation now. We'll help you with everything else.

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