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Owned and Operated Growth

The Dark Side of Roofing: Storm Chasers & Broken Incentives

πŸ“… January 20, 2026 ⏱️ 26:00 🎀 John Wilson, Adam Cherup

Chapters

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  • 1:04
    The Insurance Battle
    Adam and John discuss the frustrations of dealing with insurance companies, highlighting their 'deny, delay, and defend' tactics and the advantages of prioritizing retail clients.
  • 4:17
    Insurance Game vs. Cash Pay
    The hosts draw parallels between the insurance industry in home services and healthcare, noting the growing trend of cash-only services being cheaper and more efficient due to avoiding insurance complexities.
  • 7:52
    Insurance Company Tactics
    Adam reveals that insurance companies often train their adjusters to deny claims and litigate, even falsifying reports, making it crucial for contractors to educate customers about their rights.
  • 19:44
    Storm Chasers: Good and Bad
    Adam distinguishes between reputable storm chasers and fraudulent ones who take money and run, emphasizing the importance of hiring local, reputable contractors.
  • 28:18
    Lead Generation & Seasonality
    Adam identifies lead generation as the hardest part of running a roofing business, compounded by the industry's seasonality, especially around holidays and tax season.
  • 32:43
    Roofing Business Model
    Adam details the average sale price for retail and commercial roofing projects, explaining the high cost of doing business in Florida due to insurance and licensing requirements.
  • 36:40
    Difficulty of Starting a Roofing Business
    The discussion covers the varying difficulty of entering the roofing industry, dependent on state licensing requirements and the level of capital investment, ranging from easy for sales-only to challenging for full-service operations.

Speakers

J
John Wilson
Host β€” Owner of a plumbing, HVAC, and electric company
A
Adam Cherup

Key Takeaways

✦

Prioritize retail clients over insurance claims when possible to ensure faster project completion and better cash flow, using insurance litigation as a back-end strategy.

✦

Educate clients thoroughly about insurance company tactics; emphasize that insurance adjusters and engineers often work against the homeowner's best interest, and contractors are their advocate.

✦

Be wary of 'storm chasers'; always verify a contractor's reputation, local presence, and legitimate operating history to avoid scams and unfulfilled warranties.

✦

Develop a robust lead generation strategy, as it's the most critical component for consistent business, especially given the seasonal nature of roofing.

✦

Understand and plan for the seasonality of the roofing business, particularly around holidays and tax season, to manage cash flow and operational stress effectively.

✦

For home improvement contractors, explore direct-to-consumer, cash-pay models to bypass the complexities and delays often associated with insurance companies, similar to trends in healthcare.

✦

If operating in a sales-and-marketing-only model, leverage the lower barrier to entry but be prepared to manage relationships with subcontractors and ensure quality control.

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