The Roofing Operating System Podcast: America’s Top-Rated Podcast for Roofing Software & Scalable Growth #29 - The $1M Roofing Playbook Every Young Contractor Should Steal
\What if you could copy the exact blueprint one young contractor used to build a $1M roofing company in his 20s? Now you can.
In this episode of The Roofing Operating System Podcast, host Nick Peret (Founder of Better Boss) sits down with Bailey Masters, founder of Top Tier Roofing, who launched his business at just 24 years old—and quickly scaled it to $1M+ in revenue.
Bailey shares his no-fluff journey from sales rep to business owner, including the mindset, marketing, team structure, and tech stack that made it possible. This is a must-watch episode for young, driven contractors who want to grow fast—and do it right.
💡 What You’ll Learn:✅ The core systems Bailey used to hit $1M+ in revenue
✅ How to earn respect (and leads) as a young contractor
✅ Why Google Local Services Ads became his lead engine
✅ How to build a reputation that drives referrals
✅ Why vendor relationships and tech tools matter from day one
✅ The power of focus, family, and discipline in fast growth
00:00 Bailey’s Start in Roofing Sales
00:27 From Rep to CEO: Starting Top Tier Roofing
01:21 Overcoming Age Bias and Building Trust
03:31 Balancing Marriage, Business, and Growth
07:46 Why Conferences & Networking Accelerated His Growth
12:38 Growth Strategy: Roofing + Restoration
15:29 Lead Flow and Opportunity Expansion
18:18 Goal Setting and Team Alignment
20:07 Scaling Without Losing Margins
21:40 Building Vendor Partnerships that Drive Success
27:28 Tech, Tools & Insurance Integration
32:28 Local Marketing, LSA Ads & Brand Strategy
35:50 The Mindset Behind Bailey’s Success
Better Boss — The Operating System for Contractors Who Want to Scale Faster, Sell Smarter, and Build the Business They Always Wanted.
🌐 Learn More About Top Tier Roofing: 📅 Want to Follow a $1M Roofing Blueprint—Step by Step?Book your FREE Roofing Growth Audit and get a $1,500 playbook to systemize your ops, convert more leads, and unlock your next revenue milestone.
👉 https://mybetterboss.ai/free-roofing-growth-audit
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💥 That’s a wrap on another episode of The Roofing Operating System™—America’s top-rated podcast for roofing software and scalable growth.
If today’s insights sparked just one idea to scale smarter or grow faster, imagine what a full strategy could do for your business.
👉 Head to mybetterboss.ai to access free tools, book a discovery call, or explore systems trusted by top roofing companies nationwide.
Don’t forget to follow the show, leave a 5-star review, and share it with another roofer ready to level up.
Until next time—build better, lead stronger, and scale like a boss.