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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
17 episodes
