Raymond Little is a former roofing company owner who helped scale Perimeter Roofing into a multi-million-dollar operation before exiting to private equity. He now works as a partner and coach with Storm Ventures Group (SVG).

In this episode of the Roofing Success Podcast, Raymond shares how roofing became his second chance after addiction, what it really takes to scale a roofing company, and the sacrifices required to go from knocking doors to leading elite sales teams. He delivers real talk on leadership, sales discipline, social media, and what no one tells you about life after an acquisition.

If you’re serious about growth, hustle, and building something that lasts, this is an episode you don’t want to miss.

🎧 Listen on Spotify & Apple Podcasts
Spotify: https://roofingpod.com/spotify
Apple Podcasts: https://roofingpod.com/apple-podcasts

🔗 Guest Links
Raymond Little (Facebook): https://www.facebook.com/raymond.little.520
SVG University: https://www.svguniversity.com/2dayswithraymondlittle

🤝 Podcast Sponsors
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AI Roofing Revolution: https://roofingpod.com/airoofingrevolution
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⏱ Episode Chapters

00:00 — How AI Is Changing Insurance Roofing Claims
03:37 — Building a $30M Roofing Company
06:03 — Why Roofing Codes Matter in Insurance Work
11:34 — Are Insurance Claims Getting Harder?
15:41 — Storm vs Retail Roofing Business Models
20:30 — Using AI & Drones for Roofing Leads
25:14 — Onboarding Homeowners the Right Way
31:05 — Documentation Mistakes That Kill Claims
35:10 — Winning Insurance Scope Battles
42:25 — Training & Scaling Roofing Teams
49:45 — Growth Stages: $3M to $25M+
1:01:49 — Future of Roofing & AI

Why Roofing Is the Best Second-Chance Industry in America with Raymond Little