🎙SMB15: From Door-Knocking to $7M in Revenue: Ryan Robinson’s Roofing Journey

This is SMB15, a rapid-fire interview series featuring small business owners, investors and service providers. We dig into different industries, business models, and SMB topics. Hosted by Will Fry, founder of Mainshares.

Listen now on Spotify or YouTube.

Ryan Robinson didn’t grow up dreaming of shingles. But after working in transportation and getting laid off during a downturn, he fell into roofing — and never looked back. Today he’s the co-owner of Upright Roofing and Construction, one of the fastest-growing roofing businesses in the Dallas-Fort Worth area. Along the way, he’s also built a paintless dent repair shop and a Christmas lights business that serves 250+ homes each winter.

In this episode, Ryan shares what it really takes to run a roofing company: how crews are hired, how insurance claims are processed, and why class 4 shingles aren’t always worth the hype. We talk commercial vs. residential work, the legal shift from 1099 to W2 sales teams, and what separates a fly-by-night roofer from a reputable operator.

Some takeaways:

1. Re-roofing beats new construction. Ryan once installed 60 new construction roofs in 60 days, only to net $10,000 total. Since then, Upright has focused on re-roofing, where margins are higher and storm-driven demand is more predictable.

2. Storm chasers vs. storm catchers. Ryan breaks the storm repair market down into folks who are storm chasers or storm catchers. The chasers travel state to state chasing the latest hail storms - and typically get a poor reputation. Storm catchers, however, are locally owned & operated roofing contractors who are embedded in the community and wait for the latest storm to drive referrals and business. For homeowners, storm catchers are far preferable because the roofing contractors are around in the years to come when roofs need repair work under warranty.

3. Field sales can change your trajectory. One of Ryan’s sales reps knocked on a door and met a general contractor. That contractor was working on some large commercial projects in DFW and was in need of a roofer. That single conversation turned into three six-figure commercial jobs, jumpstarting Upright’s expansion into commercial work.

4. Ryan trains his crew to truly understand the science and help fix roofs, not just close a sale. Upright doesn’t hire high school kids looking for a summer job knocking on doors. They invest in training reps who understand the roof overhead and know everything from the pros and cons of various materials to how to deal with insurance claims.

5. Insurance-funded roofs are a double-edged sword. Margins are higher on insurance work because prices are set by carriers. But contractors often fronting tens of thousands in WIP before receiving final checks, making cash management and scope accuracy essential

Where to find Ryan and Upright Roofing + Construction:

• X: @Ry__Rob

• LinkedIn: https://www.linkedin.com/in/ryan-robinson-a86a22b0

• Website: https://uprightroofinggc.com/

• Instagram: @uprightroofingandconstruction

In this interview, we discuss:

• 0:00 Intro to Ryan Robinson

• 1:20 Why You Can’t Install Shingles Below 40°F

• 2:43 Learning Roofing from the Sales Side

• 4:00 New Construction vs. Re-Roofing vs. Repairs

• 5:42 What is TPO Roofing?

• 7:10 Sales Team Training Philosophy

• 8:22 Inside the Storm Chaser World

• 10:41 How to Vet a Roofer as a Homeowner

• 12:34 The Insurance Process Explained

• 15:36 Subcontracting vs. In-House Crews

• 17:49 How They Vet New Crews & Trades

• 19:46 Roofing Materials 101

• 24:02 Starting a Christmas Light Business

• 25:40 From Sales to Business Ownership

• 29:51 Expansion Plans

• 31:05 What Drives Ryan Robinson?