Podcast Summary: The Dark Side of Roofing—Insurance Scams, Storm Chasers, and Why Homeowners Get Burned

Podcast: Owned and Operated – A Plumbing, Electrical, and HVAC Business Growth Podcast
Host: John Wilson (B)
Guest: Adam Cherup (A)
Date: January 20, 2026

Overview

This episode dives into the “dark side” of the roofing industry, examining challenges homeowners and legitimate contractors face, especially regarding insurance scams, storm chasers, and the pitfalls that lead to people getting burned. Host John Wilson and guest Adam Cherup discuss these critical issues with a blend of humor, insider knowledge, and practical advice for both contractors and homeowners.

Key Discussion Points & Insights

1. The Insurance Nightmare in Roofing

• Insurance companies’ tactics:
  • Practically a game of “deny, delay, and defend,” leaving homeowners and contractors frustrated.
  • Insurance companies notoriously difficult to deal with, often seeking loopholes to avoid paying out claims.
  • In Florida, this issue is particularly acute; insurance denials and delays are standard practice.
• Advice for contractors & homeowners:
  • Adam recommends pushing clients toward retail transactions (direct payment, possibly with loans or in-house funding), then litigating the insurance claim afterward (01:41).
  • Contractors end up waiting months for insurance payouts and often must negotiate for higher payments, sometimes relying on dedicated staff well-versed in insurance code and forms (08:29).
• Memorable quote:
  • “Deny, delay and defend. Typical insurance. The hardest part is trying to get that customer to understand don't listen to the insurance. They are not your friend.” – Adam (00:06)

2. The “Cash-Only” Comparison to Healthcare

• Interesting parallel:
  • John discusses the shift in healthcare to cash-only/concierge models, highlighting the cost-effectiveness and efficiency compared to insurance-based practices (03:45–04:52).
  • Example: Cancer genetic screening through insurance was $7,000; cash price was $150 (04:22).
• Takeaway:
  • Adam and John agree the insurance model often creates unnecessary complications and costs in both healthcare and home renovation industries.

3. Insurance Fraud and Contractor Struggles

• Manipulation from insurers:
  • Insurance companies’ handbooks train adjusters and engineers to deny or minimize claims, even to the point of fraud—falsifying inspection reports (05:05).
  • Nonprofits like American Policyholders work to expose and fight this (05:05).
• Business implications:
  • For companies doing insurance work, knowing how to “play the game”—through codes, forms, and persistence—can double average tickets but causes significant cashflow challenges and delays (08:20–09:14).

4. Storm Chasers—The Good, The Bad, and The Criminal

• Storm Chaser definition:
  • Companies or individuals who move into regions hit by storms, offering rapid repairs—sometimes reputable, sometimes not (12:02).
• Risks:
  • Many take deposits and vanish, leaving homeowners burned; others disguise as established local businesses, often by buying small companies’ names and numbers (14:07).
  • “The cheapest guy isn't always the best guy.” – Adam (13:21)
• Advice for consumers:
  • Prioritize local, reputable contractors over strangers with 1-800 numbers or questionable histories.
  • Be wary of aggressive door-knocking campaigns after storms (15:16).

5. Seasonality and Cashflow

• Roofing is highly seasonal:
  • Demand plummets during holidays and picks up in spring through hurricane season (17:20–19:20).
  • Lead generation is the biggest challenge—“you just can't get enough” (17:19).
• Notable business stressors:
  • Planning for slow periods, managing cashflow, and quickly fulfilling jobs are crucial to survival.

6. Business Model & Industry Barriers

• Retail vs. Insurance:
  • Adam’s company is ~80% retail, 20% insurance, which allows faster job turnaround and fewer headaches.
• Project size and scale:
  • Residential roofs: $20,000–$30,000 typical. Commercial replacements can reach $1M+ (20:00–21:48).
• Licensure and Entry Difficulty:
  • Licensing laws vary by state; Florida is among the toughest, making legitimate entry more difficult (22:16).
  • “State of Florida, it’s a 9 out of 10 to get started. Non-licensed state? Probably a five.” – Adam (24:41)
• Sales/Marketing-Only Models:
  • Some successful roofing companies are pure sales and marketing shops, subbing out all labor (25:03).
  • For those companies, the barrier to entry (difficulty) is much lower: “If you’re just sales and marketing, like two or three [out of ten].” – John (24:57)

Notable Quotes & Memorable Moments

• “Deny, delay and defend. Typical insurance. The hardest part is trying to get that customer to understand don't listen to the insurance. They are not your friend.” – Adam (00:06)
• “Listen to your contractor. When you go to the doctor, you listen to the doctor. It burns me when... somebody at an insurance company who’s not a doctor says no.” – Adam (11:20)
• “You got guys that come in, take the money and run in the storm chasing world. That’s the dark side of it.” – Adam (00:18)
• “The cheapest guy isn’t always the best guy.” – Adam (13:21)
• "If you're running a sales and marketing roofing business, then I think difficulty is pretty low… if you're actually, if you have to invest into equipment and staffing, I think that is more challenging." – Adam (25:23)

Timestamps for Important Segments

• Insurance headaches & recommendations: 00:06–02:44
• Cash-only healthcare comparison: 03:45–04:52
• Insurance fraud & nonprofit advocacy: 05:05–05:55
• Challenges collecting insurance payments: 07:06–09:16
• Retail vs. Insurance business mix: 09:31–10:38
• Educating the customer: 10:38–11:49
• Storm chasers & scams: 11:49–15:12
• Lead generation & seasonality: 17:02–19:45
• Typical job size, commercial scale: 20:00–21:54
• Barriers to entry, licensing: 22:16–24:41
• Sales/marketing only models: 25:03–25:23

Tone & Style

The conversation is frank, fast-paced, and blends real-world advice with humor and candor. Both John and Adam use analogies and real stories to make their points accessible to pros and homeowners alike.

For contractors, the message is clear: Master insurance processes, focus on retail where possible, and beware of shady actors—in your market and in your own operation.
For homeowners: Don’t trust storm chasers or take insurance companies at face value. Vet your roofer thoroughly, and trust the experts who actually understand your roof.