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Can I Tell in 5 Minutes If an Account Is Worth Pursuing?

April 10th, 2026

2 min read

By Warren Cleveland

Hero Image Can I Tell in 5 Minutes If an Account Is Worth Pursuing?
Can I Tell in 5 Minutes If an Account Is Worth Pursuing?
2:27

How Do I Know in the First Five Minutes of a Conversation Whether an Account is Worth My Time.

This is one of the best questions you can ask. Because the agents who struggle with captives aren't struggling because they can't close. They're struggling because they're spending time on accounts that were never going to work. Fix that first, and everything else gets easier.

Here's the good news. You don't need a spreadsheet. You don't need loss runs. You need to know three things, and you can find all three of them in a short conversation.

First, are they big enough. The table stakes for a captive are $250,000 in combined premium across workers' comp, general liability, and auto. If they're not there, the economics don't work. Full stop.

Second, are they willing to take some risk on themselves. And here's what that actually sounds like in a conversation. I'm tired of paying all this money and getting nothing for it. I feel like we don't file claims and we never see any benefit. We invest in training, we invest in safety, and the insurance industry doesn't recognize any of it. That's the person you want. If they're frustrated with what traditional insurance has given them and willing to bet on their own performance, you're in the right conversation.

Third, do they invest in their people and their risk. The right captive member isn't just lucky with claims. They work at it. Safety programs. Training. Proactive risk management. If the only reason their losses are clean is good fortune, that's a different conversation than if they've built a culture around it.

That's it. Three things. You can surface all three of them in the first five minutes without asking for a single document.

Now here's what I'd add. Even if someone doesn't check all three boxes today, that doesn't mean the conversation is over. It means you know where you stand. You come to us early, tell us what you have, and we'll tell you if it's worth pursuing now or worth keeping warm for later. We're always building toward the right next group of members. An account that isn't a fit today could be exactly what we're looking for in six months.

The agents who win at captives aren't the ones who chase every account. They're the ones who qualify fast, know what they have, and never waste time on something that was never going to work.

We'll help you get 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