Guest: Raymond Little — Founder, SVG Roofing Coaching | Contra Shoes

Guest Links: Facebook: Raymond Wendell Little | Instagram: https://www.instagram.com/rwl612/

Raymond Little built a roofing company from zero to nearly $100 million, exited to private equity for $40 million, and now runs SVG helping owner-operators between $1M and $10M break through their plateaus. In this episode, Raymond gets raw about what actually works in roofing sales in 2026, starting with storm vs retail in today's market, why wind claims are getting harder everywhere, and why the four-to-eight knocking window beats the nine-to-five mindset most new companies are still stuck in. He breaks down why you should never poach million-dollar producers from other companies but instead build them yourself, why a hefty override or ownership needs to be in the field driving the team daily, and his rule that you can't develop anyone greater than yourself. The conversation digs into Raymond's hiring philosophy built around second-chance people, team players, and good energy over credentials or personality tests, his 90-day ride-along system where new reps work the first 4-5 deals in the truck with him from knock to build, and the sales tactic of using the adjuster and homeowner as "teachers" to elevate new reps while making the process fully transparent. Raymond also shares why personal development around physical health, clean living, and healthy relationships is the foundation his entire company was built on, the real numbers on what 1099 reps should earn per lead, why one roof a week pays the bills and three a week means you stop checking price tags, and his mentor story of following Kurt the Nintendo and hitting half of what that man accomplished as his own definition of success. He also gets into Contra Shoes, the lightweight flexible roofing shoe a quarter the weight of Cougar Paws, designed for reps who knock and climb all day.

Guest: Ryan Fitzgerald — Plumbing Department Leader, Fitzgerald Heating Air and Plumbing (Las Vegas, NV)

Guest Links: Facebook: Ryan Fitzgerald (Las Vegas, Nevada)

This episode covers how to layer a plumbing department onto an existing HVAC company and scale it from almost nothing to over $5 million in a single year. Ryan Fitzgerald joined a company in Las Vegas that was doing $14 million in HVAC but only $400,000 in plumbing, and within his first full year built the plumbing side to $5.4 million with a team of eight technicians and four installers. He breaks down exactly how that happened: a dedicated outbound team hammering phones to fill the board, assigning calls based on each tech's strengths and weaknesses, a four-option sales process where the homeowner feels empowered to choose rather than pressured, and leveraging HVAC cross-selling to get plumbing in the door. The conversation gets into why implementing systems too early can actually hurt you, including a real example of a field manager role they tried at $5 million that created friction between installers and sales techs and had to be pulled back until $7 or $8 million. Ryan also shares how growing too fast led to warranty callbacks when his install crew got overloaded, how he trains techs to turn leak detection and water quality testing into high-ticket opportunities in the Las Vegas market through education rather than pressure selling, and why the culture shift between HVAC and plumbing went from "redheaded stepchild" to healthy competition once the plumbing guys started keeping pace on revenue. He explains his leadership approach of quarterly deep dives with each team member, leading by example by still jumping into the trenches, and why accountability has to go both ways between leaders and the team.

Guest: Brad Strawbridge — Founder, Capital City Roofing & BuilderLync

Guest Links: Website: https://builderlync.com/

This episode covers practical, real-world ways roofing companies are using AI right now to automate non-revenue tasks and free up teams to focus on selling and customer experience. Brad Strawbridge walks through how he uses Claude Co-Work to build reusable workflows that automate everything from proposal creation to dispatching sales reps, how the teach feature lets you record clicks and turn any repetitive CRM process into a saved workflow you can trigger with a forward slash command or put on a schedule. He explains how he built Capital City University, a full training curriculum for roofing using Notebook LM with manufacturer materials and RCA-approved content uploaded as knowledge sources. The conversation also covers BuilderLync, an all-in-one CRM built specifically for roofers that replaces five or six separate tools, handling everything from AI-powered cold outreach and lead nurturing to scheduling, dispatching, supplements, bookkeeping, and payment collection. Brad shares his take on why newer roofing companies have a massive advantage right now by starting AI-first instead of trying to retrofit old processes, why the best way to use AI is to give it a ridiculous amount of context before asking for answers, and his five-year outlook on where roofing is headed with the Roofing Alliance bringing the trade into universities and driving technology adoption across the industry.