Unthinkable Tragedy

Welcome to the debut episode of RiskReady Roundup, the podcast that goes beyond the headlines and into the trenches of disaster recovery, insurance battles, and homeowner resilience. Hosted by Jason Doyle, this first episode sets the tone for the entire series: raw conversations, practical strategies, and lessons you can use to protect your home, your family, and everything you’ve worked hard for.

Our guest is James Wesby—cofounder of RiskReady Ventures and someone who knows firsthand what it’s like to lose everything in an instant. One quiet night in New Orleans, James was jolted awake by a lightning strike. Within hours, he and his wife Carol were standing barefoot on the sidewalk, watching their entire home burn to the ground. The loss wasn’t just a house—it was memories, keepsakes, and a sense of normalcy erased in a single night.

In this episode, James takes us back to that moment. He shares the shock of realizing that in less than three hours, life as he knew it was gone. He talks candidly about the helplessness of standing by as flames consumed everything, and the surreal reality of starting over with nothing but the clothes on his back. But as devastating as that night was, what came next proved to be an even greater challenge: navigating the insurance system.

James opens up about the maze of paperwork, deadlines, and delays that made recovery feel impossible. Instead of being rescued by his insurance company, he found himself overwhelmed by silence, forms, and confusion. The emotional toll of grief compounded by bureaucracy revealed a harsh truth most homeowners never realize until it’s too late—there’s no roadmap for what happens after disaster strikes.

Out of this painful journey came the spark that would ignite RiskReady. As James explains, the turning point was the realization that preparation could have changed everything. If he had the right tools to organize documents, track claims, and stay on top of deadlines, the fire would still have been tragic—but not nearly as devastating. That’s when conversations with Jason Doyle led to the birth of RiskReady: a platform built to help families avoid the chaos, confusion, and unnecessary setbacks James faced.

This episode is more than a story—it’s a blueprint for every homeowner. James shares what he wishes he had known before that night: the importance of documenting everything (photos, receipts, records), understanding your insurance policy inside and out, and preparing for the reality that claims aren’t smooth, no matter what the commercials say. He also underscores the power of emotional resilience, reminding listeners that recovery isn’t just about paperwork—it’s about finding strength in the face of loss.

By the end of the conversation, you’ll understand exactly why RiskReady exists and why now is the time to take action. Whether you’re a first-time homeowner, a landlord with multiple properties, or simply someone who never wants to be caught unprepared, this episode will leave you thinking differently about what it means to truly be “risk ready.”

If James’s story resonates with you, don’t wait for disaster to force your hand. Download the RiskReady mobile app today on the App Store or Google Play and take the first step toward protecting yourself, your family, and your future.

RiskReady Roundup isn’t here for fluff or shortcuts. We’re here for real stories, hard-earned lessons, and the practical knowledge you need when life throws the unthinkable your way.

Listen now to Episode 1, and get ready to Get Ready, Be Ready, and Stay Ready.