Insurance claims, storm chasers, and broken incentives — welcome to the dark side of roofing.
In this episode, John Wilson sits down (again) with Adam Cherup to unpack what really happens behind the scenes in roofing — from “deny, delay, defend” insurance tactics to the storm-chasing playbook that leaves homeowners stuck holding the warranty bag. They also get practical: seasonality, lead gen, cash flow, and what it actually takes to start a roofing business (especially in Florida).
In this episode, we cover:
- The Insurance Game: “Deny, delay, defend” — and why carriers aren’t your friend.
- Retail vs. Insurance Strategy: Why some roofers push retail first, then litigate the claim after.
- How to Win Insurance Work: Xactimate, codes, the paperwork game, and why payouts can double when done right.
🔥 What You’ll Learn:
- How contractors can guide homeowners through insurance without waiting months for approvals.
- The biggest red flags of storm-chasing contractors (and how people get burned).
- Why roofing cash flow can get brutal — and how seasonality + claim delays compound it.
- What makes roofing “easy” vs. “hard” depending on your model (subbed installs vs. controlled labor).
💼 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
💼 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
💸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.
🔗 Connect
John Wilson
Adam Cherup
Send Us Mail!
More Ways To Connect with O&O
Leave a Review
John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC
📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.
