In this episode of the Power Producers Podcast, host David Carothers, co-host Kyle Houck, and returning guest Kevin Ring of the Institute of Work Comp Professionals come together for a special tribute to the legacy of an industry pioneer, Preston Diamond. The conversation is sparked by the release of “The Diamond Playbook,” a new book compiling decades of Preston Diamond’s influential weekly sales letters. Kevin shares the story behind the book’s creation and offers a deep dive into Preston’s timeless sales philosophy: being client-centric, using stories to build trust, and moving beyond a product-pushing mentality. They also discuss how Preston’s critiques of agency websites from the 1990s are still shockingly relevant today.
Honoring a Legacy: The Diamond Playbook
Kevin Ring details how the Institute of Work Comp Professionals discovered a massive archive of Preston Diamond’s weekly sales letters, which began as a fax broadcast, and compiled them into a book. The project was a surprise tribute to honor Preston’s immense and ongoing contribution to the insurance industry and the thousands of agents he has mentored.
The conversation centers on the core of Preston’s teachings: never be product-centric. Instead, agents must first focus on understanding a client’s needs, wants, and fears. By building a relationship of trust and using powerful stories to explain complex concepts, the insurance sale becomes a natural and easy conclusion to a value-driven conversation.
A fascinating takeaway is an essay Preston Diamond wrote in the 1990s critiquing agency websites. Kevin and David discuss how his gripes—that most sites are just static “electronic business cards” instead of powerful tools for establishing expertise and credibility—are just as true today, highlighting a persistent missed opportunity for many agencies.
The episode revisits another of Preston’s core tenets: focus on deepening relationships with existing clients. They discuss the immense, low-hanging fruit available by rounding out accounts (“client share”) and networking clients with each other. This creates powerful exit barriers and demonstrates a level of value that goes far beyond just placing a policy.
The insurance industry is at a pivotal moment. As artificial intelligence (AI), robotic process automation (RPA), and API-driven tools continue to accelerate, the conversation has shifted from “should we adopt tech?” to “how can we implement the right tech without breaking our operations?”
Let’s set the record straight: most commercial insurance producers don’t fail because they can’t sell. They fail because they don’t plan. They lack process. They don’t follow up consistently—or when they do, it’s weak and generic.
In today’s competitive environment, trust is not built through hard closes. It’s built through consistency. Being present when the incumbent fails. Being available when the buyer is finally ready. Being prepared with insight when everyone else is just pushing a quote.
Email marketing is often treated as an afterthought in the insurance industry. Producers focus on cold calling, referrals, and in-person meetings—but overlook one of the most powerful tools already sitting in their hands: their email list.
If you’re an insurance producer or agency principal and you’re not actively leveraging email marketing to drive revenue, retain clients, and expand your footprint, you’re missing a golden opportunity. When executed properly, email marketing delivers unmatched ROI, enables targeted cross-selling, builds credibility, and enhances retention—all at a fraction of the cost of other lead-generation tactics.
The insurance industry is evolving at a rapid pace, and the lines between technology, relationships, and service delivery are blurring more every day. As InsurTech continues to capture the attention of carriers, agents, MGAs, and startups alike, the challenge has shifted from finding new tools to figuring out which ones are actually worth using. Too often, insurance professionals are overwhelmed by noise—buzzwords like “AI-driven,” “revolutionary,” or “disruptive” are plastered across every product demo and sales pitch. But for forward-thinking insurance professionals, the real focus isn’t just on adopting the newest thing—it’s on building ecosystems where people and technology thrive together.
The insurance industry is undergoing a quiet transformation. While headlines often focus on the flashy front-end tools and direct-to-consumer disruption, the real revolution is happening behind the scenes — in the back office. From agency onboarding delays to outdated compliance workflows and manual licensing tasks, these friction points cost MGAs, carriers, and agencies valuable time, revenue, and relationships.
In an increasingly competitive commercial insurance landscape, agency owners are struggling to find long-term solutions for succession planning, talent retention, and business perpetuation. Many have considered private equity sales, others offer limited equity to top producers—but a growing number are discovering a more powerful alternative: the Employee Stock Ownership Plan (ESOP).
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