The Waymaker with Stuart Leo, Episode #181

The commercial insurance world isn’t for the faint of heart. It’s unpredictable, chaotic, and constantly demanding producers to manage competing pressures—client needs, renewal deadlines, life events, prospecting goals, and agency responsibilities. And if you’re a middle-market producer, multiply that by ten.

In the middle market commercial insurance space, the role of the producer has never been more critical—or more misunderstood. Too many producers still view their job as selling policies instead of what it truly is: protecting the assets and livelihoods of the businesses they serve.

The middle market rewards depth, not breadth. Yet many producers still approach it like a volume game, quoting everything that moves, chasing price, and hoping activity turns into production. From the outside, it looks like hustle. From the inside of the underwriting and wholesale world, it looks like noise.

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.