Roofing

From Prison at 17 to Roofing Empire: The Story of Davey Cox

By Sydney Bertun  •  December 04, 2025  •  3 min

Some contractor success stories are good. Some are inspiring. And then there’s the story of Davey Cox, owner of Cox Roofing & Restoration in St. Louis - a man who went from prison at to running one of the fastest-growing roofing companies in Missouri.

It’s a story of redemption, grit, and second chances. And it’s a reminder that behind many great contractors are human beings fighting to build a better life.

Growing Up Between Two Worlds

Davey spent his childhood split between small-town Missouri and Palma de Mallorca, Spain. The contrast shaped him early — he learned to navigate different cultures and make friends anywhere. But when he came back to the states at 15, things changed.

Friends who once experimented with marijuana were now deep in the local drug scene. Trying to impress older kids in his town, Davey followed them down a dark path — dropping out of school and selling drugs. 

In & Out Of Prison

By 17, Davey was in adult prison. When he got out, he picked up work as a roofing rep. But Davey didn’t leave the drugs behind– at least not yet. His real moment of reckoning came after a federal raid on his house. 

“If they’d prosecuted the whole thing, it would have been a life sentence,” he says. “I’m literally sitting here on a second chance.”

That second chance allowed Davey to imagine a better future, even as he served out an eight-year sentence. 

Gavin - The Reason He Didn’t Give Up

Gavin is Davey’s nephew, but for most of his life, Davey was the only father figure he had. When Davey went to prison, it was Gavin who got him through. 

The two spoke on the phone every day and made plans to open a roofing company together. Gavin stayed committed to their dream all through high school – even when teachers said he should do something else. 

When Davey walked out of prison in 2024, he was full of doubts. But Gavin was right there, expecting Davey to follow through. So he did. 

Paying It Forward  

Davey started Cox Roofing, sleeping in a spare room and paying for materials in cash. Little by little, the business grew. Gavin became his right-hand man, learning how to manage the cash flow at just 19.

Soon, Davey bought a home and turned it into a “storm dorm,” housing any crew who needed a place to stay on couches, air mattresses, and makeshift beds. He was making the most of his second chance and paying it forward.

One of the people who ended up at the storm dorm was Daniel– a 25-year-old who had been living in a tent behind Walgreens. Davey let him take a shower, and planned to help him fly home… but Daniel asked for one day to prove himself.

Three weeks later, with no roofing experience, Daniel had 50 jobs registered and started making $6,000 per week.

The Secret to Surviving Roofing: Cash Flow

Davey shares hard-won advice for anyone starting a roofing company: “You can only build as fast as you can collect.”

Big deposits in your bank don’t mean you can build 10 roofs at once. Materials and labor wipe cash fast. The key is pacing production and protecting your cash flow — especially early on.

His advice for struggling roofers: “Just keep pushing… It’s kind of like door knocking. You can knock 10 doors and that one person's going to open it and say, ‘Yeah.’ So just keep going day by day and things will change for you.”

A Lesson for Homeowners

Stories like Davey’s show how powerful second chances can be — but they also highlight why homeowners need a vetted, verified contractor they can trust with their home.

That’s why Directorii exists.

When you hire through Directorii, you get:

Verified Contractors Only

Every contractor on Directorii goes through background checks, license verification (when required), insurance validation, and financial screening. Search for your next pro here.  

While a contractor’s criminal history is important, it’s only one part of the picture. The reality is that most contractor fraud and deposit thefts are the result of simple bad money management. That’s why we also do a financial screening to look at the health of the buisness, and determine whether they can be trusted long-term. 

$250,000 Protection

Every job automatically comes with $30,000 deposit protection, with full job coverage up to $250,000. If something goes wrong with your project, Directorii will make it right. 

We are proud to stand behind our contractors, but we are equally committed to the homeowner. You can read real stories of claims we’ve paid out here.