Insurance, eh? With Jeff Roy, Episode #87

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.