Most people dream of building a successful business.

Raymond Little built one, sold it for $38 million, and completely changed what roofing leadership looks like.

In this episode, Raymond — the former owner of Perimeter Roofing and now a partner at Storm Ventures Group (SVG) — shares his incredible story of redemption, resilience, and business mastery.

From starting over after prison to leading a team that generated over $200 million in sales, Raymond reveals the mindset and systems that allowed him to scale, create loyalty, and eventually exit on his terms.

Here’s what you’ll learn in this episode:

- How to build loyalty and culture in a transient industry where reps often leave to start their own company.

- Why the key to scaling from $1M to $50M+ isn’t marketing — it’s leadership development.

- What private equity really looks for when buying a roofing company — and how to prepare for a profitable exit.

- The psychological side of selling your “baby” and finding purpose after financial freedom.

- Why roofing owners should invest in training and systems, not higher commissions.

- How Raymond used social media storytelling to dominate his market and turn every build into marketing content.

- His take on AI, automation, and private equity’s role in shaping the future of the roofing industry.

- The mission behind his next chapter with SVG — rebuilding the industry through education, training, and technology.

Whether you’re just starting your roofing company or you’re aiming for your first eight-figure exit, this conversation will give you a blueprint for scaling faster, leading better, and thinking bigger.

📝 Episode Notes / Key Takeaways

- Your biggest growth constraint isn’t marketing — it’s leadership bandwidth.

- Train leaders, not followers: duplication is how you scale.

- Building loyalty comes from leading by example — first one up, last one home.

- Culture and boundaries create respect, not rules.

- Private equity rewards structure, reporting, and leadership succession, not hustle.

- Social media is the new neighborhood — every rep should be posting stories from the field.

- AI won’t replace people — it will replace inefficiency.

- Selling your company gives freedom, but not purpose. Find your next mission early.