Ep.128 - In this episode of Endless Customers, Alex Winter sits down with flood insurance educator and entrepreneur Chris Greene, president of The Flood Insurance Guru. They unpack what it takes to earn trust in a complex industry by making clarity a service and by answering the questions buyers are already asking in plain language.

Chris shares how a personal experience, nearly losing his home, pushed him to rethink how flood risk and insurance should be explained. That mindset led to a content engine built on real stories, real data, and relentless consistency. He breaks down how self-assessment tools can generate qualified leads at scale, why localized answers build trust faster, and how he is using AI to clone his expertise so his team and customers can get help without bottlenecks.

Highlights include:

• How a flood risk tool generates about 200 leads a month


• The 1,500 videos in 1,500 days approach to building trust


• How localized data and street-level specificity builds credibility


• Why self-assessment tools reduce friction and speed up decisions


• How Chris built an AI clone to scale knowledge and support his team


• The framework he uses to guide every technical decision

If you sell something complex and your buyers feel overwhelmed, this episode will show you how to simplify without dumbing it down. Trust compounds when your content actually helps people make confident decisions.

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Chris Greene