Starting a Roofing Company: What Year-One Roofers Are Learning the Hard Way

Owl Roofing is a young company. We’re building it in public, mistakes and all. So I asked my Facebook feed: Who’s a year one roofing company this year? I’d love to connect with more folks at a similar point in the journey.

The thread blew up. Dozens of new owners raised their hands: six months in, eleven months in, rebooting after shutting down, moving from commercial into residential. Veterans jumped in too, with the kind of advice you only get after a few bad years.

Here’s what year one actually looks like for roofers right now.

Why year one is the hardest year

In year one you’re the salesperson, the estimator, the production manager, the marketer and the bookkeeper. You don’t have reviews yet, you don’t have referrals yet and every dollar of marketing feels like a bet. Most of the owners in this thread are figuring out the same handful of decisions.

Decision 1: Retail or insurance?

A clear pattern showed up. A lot of new companies are starting retail-only.

I’m 11 months in. Residential retail. No insurance.

Grayson Carey

2.5 months for me. Only retail, no insurance.

Eli Sanchez

6 months in with Copper Crown Roofing LLC. All retail only, and we just recently started touching insurance again. Like, this week.

Courtney Fry

It makes sense. Retail is simpler to learn, cash comes faster and you’re not waiting on adjusters. Insurance work can come later, once your process and paperwork are tight.

Decision 2: Build systems from day one

We have a lot of roofers in our mastermind group who are in their first couple years of business. We specialize in helping young and new contractors systemize their business from the beginning. I’m in my 20th year now and have a passion for helping good people succeed in this business.

Randy Brothers, Founder, The Roofing Academy

We’ve been building ARS Building Services for a few years now and have definitely gone through the cycle of beefing things up, trimming the fat and figuring it out as we go.

Sean McDonald

That cycle is normal. Add people, add cost, cut what isn’t working, repeat. The companies that survive do it on purpose, with numbers, instead of in a panic.

Not every year one starts from zero

First year in Nashville as a residential roofer. Our company has been around for 5 years, but mainly in B2B services. 2026 is our first year of intentional growth.

Simon Lawrence

1 year in, all commercial. Fargo, ND. We have a pretty good thing going.

Joe Malloy

I’m on month 3 after rebooting. Shut it down in 2024.

Matt Brasic

Respect to Matt. Shutting down and starting again takes more guts than starting the first time.

I got registered as a contractor in February but have been too busy doing roofing call center builds to sell any roofs. Added over half a million in revenue for my clients last month across 3 roofing companies, and I’m really wondering why I’m not producing that revenue for myself.

Sierra Campbell

The cobbler’s kids have no shoes. Every marketer and consultant who’s started their own contractor business knows this one.

Find your people

The best idea in the thread came from Taylor Ammons, and it got the most reactions by far.

It would be really awesome to follow around ten different year one roofing companies, documenting their journeys and what separates the ones that really take off from the ones that stay stagnant.

Taylor Ammons

Just finished year one in central Texas. It would be awesome to collab with you and others about what’s working and what’s not.

Mario Fender

Year one is lonely. A small group of owners at the same stage, comparing real numbers every month, beats any course. If you’re in year one, find four or five others and start one.

Advice from the veterans

It feels like yesterday but it’s been some years. Man, you are in for some life! Keep your integrity, your quality of life, and treat people well. Keep your head up!

Peter Reed Jago

We’re year 5 and it still feels like year one most of the time.

Taylor Gammill

I’m on year 7 but feel like year 1! I’d still be willing to talk with any owner to discuss business.

Josh Bruce

Bro, I know you’re year 1, but I’d guess you’re ahead of most year ones out there. You should be connecting with those in their 5th year.

Mark Cantrell

Fair point, Mark. Learn from the year-fives. Build community with the year-ones.

The funny answers

I’m at year 37.

David Yoder

There’s at least 1,000 of y’all in DFW.

Dennis Roy Kirkpatrick Jr

What I’d tell a year one roofing company about marketing

From the Hook Agency side, here’s where I’d put limited dollars in year one:

1. Google Business Profile first. It’s free, and it’s where a huge share of local roofing calls start. Real photos, every service listed, every review answered.
2. Reviews on every job. Ask at the end of every install. Reviews are your credibility when you don’t have a track record yet.
3. A simple, fast website you own. Service pages, city pages, real project photos and a phone number at the top.
4. One paid channel, tracked by name. LSA or Google Ads. Track every lead to a signed job or a no.
5. Your network. Friends, family, past employers, insurance agents, realtors. Tell everyone what you do.
6. Don’t buy everything at once. Add channels as your close rate and cash flow prove they work.

Takeaways for new roofing company owners

• Retail-first is a common, sensible start. Add insurance when your process is ready.
• Build systems early, even simple ones.
• Expect cycles of growing and trimming. Run them by the numbers.
• Find a peer group at your stage and a mentor a few years ahead.
• Protect your integrity and your quality of life. You’ll need both in year five.

In year one too? Drop me a note. I’d love to connect.