In the fourth and final episode of The Captive Conversation on Power Producers Shoptalk, host David Carothers and Warren Cleveland of Captive Coalition unpack the conversation framework that allows agents to stay in control of their most valuable client relationships. They reframe the captive solution as the ultimate business continuity plan for an agent’s book, ensuring long-term retention. The conversation provides tactical advice, including a powerful “pattern interrupt” to start the discussion, and stresses the importance of shifting from a salesperson to a true strategic advisor. They also cover the right and wrong times to introduce the captive concept and why agents must act as the “quarterback” to guide their clients.
David reframes the captive conversation away from being just another market. Instead, he positions it as the ultimate “continuity plan” and “finish line” for an agent’s best clients. Getting an account into a captive creates powerful financial and strategic ties that make them a client for life, effectively protecting them from competitors.1
This episode drills down on the critical mindset shift required to succeed. A captive is a long-term business strategy, not a quick premium-saving quote.2 The conversation contrasts the transactional salesperson who asks for loss runs with the strategic advisor who discusses growth, profitability, and preserving the bottom line—a conversation that wins 100% of the time.
Warren provides a tactical opener to spark curiosity and bypass typical sales resistance. He shares his five-second “pattern interrupt”—”I show business owners how to own their own insurance company”—and explains how this simple phrase immediately elevates the conversation from a commodity sale to a high-level strategic discussion.
The episode provides crucial advice on when to introduce the captive concept. They warn agents not to present it at renewal alongside traditional quotes, as that is a losing strategy. The right approach is proactive and educational, starting the conversation well in advance, such as 90 days after the previous renewal, to properly frame it as a long-term play.
Personal lines has quietly become one of the most competitive segments in the insurance industry. Agencies that once dominated their local markets are now fighting to differentiate themselves against direct writers, digital-first carriers, and large brokers with massive content machines.
The cyber insurance market has always been unpredictable. Over the past decade, we’ve seen it move from an emerging line of coverage to one of the most volatile, swinging rapidly between soft and hard market cycles. But today, cyber has entered one of the softest markets in recent memory—and that presents a rare opportunity for both agents and clients.
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.
Breaking into the commercial insurance industry is never easy—especially when you’re young, new, and entering a hard market where expectations are high and patience is low. But every once in a while, a story comes along that perfectly illustrates what it really takes to survive and succeed as a new producer.
Most commercial insurance producers believe their edge comes from relationships, market access, or quoting speed. Those things matter. But at the middle market level, they are no longer enough.
The producers who consistently win larger accounts, earn underwriter trust, and build long term career leverage all share one trait that rarely gets talked about openly.
We can talk all day about marketing funnels, quoting platforms, and prospecting strategies—but if you don’t have people who can sell, none of it matters. Every agency owner I talk to says the same thing: “We just can’t find producers who can sell.”
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