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Welcome to the dark side of the roofing business. In this episode, John Wilson sits down (again) with Adam Cherup to unpack what really happens behind the scenes in roofing insurance claims—from the infamous “deny, delay, defend” tactics to the storm-chasing playbook that leaves homeowners holding the bag. If you are looking for roofing lead generation tips or want to know how to start a roofing business, this conversation gets practical on seasonality, cash flow, and the reality of winning insurance work. 👇 In this episode, we cover: The Insurance Game: Uncovering the “Deny, delay, defend” strategy—and why insurance carriers aren’t your friend. Retail vs. Insurance: Why some roofing contractors push retail first and litigate the claim later. Roofing Seasonality: Why Q4 slows down (even in Florida) and when the roofing business ramps back up. Lead Gen & Speed-to-Lead: The biggest constraint in roofing sales and why you can “never get enough” leads. Business Model Breakdown: Typical job sizes, retail vs. insurance, and labor-only opportunities. 🔥 What You’ll Learn: How contractors can guide homeowners through insurance claims without waiting months. The biggest red flags of storm-chasing contractors. Why roofing cash flow is brutal and how claim delays compound it. The difficulty of starting a roofing company in licensed vs. non-licensed states. 💼 Extra Special Thanks to Service Scalers! We’ve been partnering with Service Scalers to maximize our Local Service Ads (LSAs) and optimize our Google My Business profiles, and the results have been incredible. With hundreds of thousands in sales and 900+ calls in a single week, GMBs are now our top-performing organic lead channel. Want to learn how Service Scalers can do the same for you? 🔗Check Them Out Here https://servicescalers.com/free-marke... 💼 Shoutout to Quick Staffers LLC Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts. 🔥 Get $1,000 off your first placement here: [https://www.quickstaffers.com/] 💸Sponsored by CFO Made Easy Built a strong trades business? Let’s take it to $10M and beyond. CFO Made Easy offers part-time CFO services for home and trade service businesses—helping you boost cash flow, maximize profit per tech, and make clear growth decisions. 📈 Free Offer: Book a 45-min Financial Insight Session to uncover growth blockers. [https://cfomadeeasy.com/owned/] 🔗 Connect John Wilson: https://x.com/WilsonCompanies Adam Cherup: / pitcrewroofing ⏱️ Timestamps: 00:00 Intro: The Dark Side of Roofing 00:43 The 'Deny, Delay, Defend' Insurance Strategy 02:32 Retail Roofing vs. Insurance Claims Models 11:52 The Truth About Storm Chasers 15:04 Door Knocking & Lead Gen Tactics 19:53 Commercial vs. Residential Roofing Business 22:11 How to Start a Roofing Business (Florida vs. Unlicensed) #RoofingBusiness #InsuranceClaims #StormChasers #RoofingLeads #OwnedAndOperated