Up on the Rooftop: Jauregui brothers built reputation job by job

The first roofing job Chewy Jauregui ever took almost made him walk away from the profession. 

Someone Jauregui knew did roofing part time and hired him for one job. But after a week of working on a problematic steep incline that was hard to walk on, let alone roof, it wasn’t an experience he wanted to repeat.

“He asked me to stay. On the inside, I wanted to say no,” Jauregui said with a laugh. “But I said yes and took a risk.”

That risk led to the formation of Chewy and Teo Roofing two years later – a company that Jauregui runs with his brothers, Teo and Santiago. It started as a weekend side job, Chewy said, but it became a full-time business in 2003.

“Little by little,” he said, “we were learning.”

The business expanded beyond the brothers but still consists of about nine family members.

Teo, Santiago and Chewy Jauregui. Photo by Rachel Lukas.

“A few nephews here, cousins there,” Jauregui said.

The company’s services have also expanded – into asphalt, other kinds of roofing, siding and gutters. Every few years, roofs have changed and trended in different directions, pushing the brothers to do the same.

“A new style, a new material,” Jauregui said. 

In the last six years, he said, many people have turned to metal roofs. During the same time span, they’ve seen a trend toward a particular building type: pole barns.

Last year, the company took on a barn owned by the Parr family, which was a mix of the two recent trends: a pole barn with a metal roof. 

Metal of the kind found on the Parrs’ barn can cause problems because the roof is made of multiple metal panels that are tightly secured together. Add to that an uneven rooftop that had to be fixed before they could start the roofing work, and it became one of the most difficult roofs they’ve worked on.

The metal panels have to be adapted to each individual project. With a machine they purchased a couple of years ago, they cut the metal themselves. 

The machine feeds coils of metal out of a trailer onto a thin conveyor belt that holds the metal up until it reaches a small mechanism set to the length where the metal needs to stop. Chewy said they’ve done spans from two feet to 65.

On the Parrs’ barn, there are two rows of metal panels at the two conjoining slopes on the barn, but with dormer windows built into the sides, they had to contend with three different lengths and keep them very straight in order to use the metal. 

The metal roofs of Keith Parr’s house and barn in the Town of Gibraltar required extensive customization. Photo by Brett Kosmider.

Keith Parr, who owns the barn, said he had to get it redone after its asphalt shingles started ripping off during every storm. He and his wife, Lissa, are trying to repurpose the building as a cattle barn.

Parr found Chewy, Teo and Santiago through Great Northern Construction, which built the Parrs’ house and was fixing some of the construction problems with the barn. 

“They’re fantastic people,” he said of the brothers. “I was a little scared at times watching them because we finished it in December when the snow was flying. I was happy when they were done. For them.”

The metal panels are the same ones the Parrs have on the roof of their house, Parr said, and he doesn’t doubt the roof will be around for a long time.

“It’s perfect,” he said.

When someone is looking for a roof – whether it’s a new build or an old one – Chewy said it’s the roofers’ job to know exactly what they’re doing.

“Some people … they don’t realize that they have a lot of responsibility because if something goes wrong, you won’t have a ceiling,” he said. “The trust is needed.”

For that reason, trust was the hardest part about starting the business, Jauregui said. Just as roofers must know what they’re doing, customers must believe their roofers know what they’re doing.


“We speak a second language, you know,” he said. “English is a second language, and years ago, that was tough to get people’s trust because you need to know what you’re doing.”

Roofing can be one of the fields in which it takes a body of work to build dependability, but new roofers need dependability to get that work. To succeed, the Jauregui brothers worked and learned and now offer eight kinds of roofing.

Hard-earned trust has brought them to this point, and they do not take it lightly. Over and over, they expressed how thankful they are for their customers’ trust in their company and belief in them.

“All the companies that hire us,” Teo added, “that believe in us, that trust in us. We are so happy to serve in this community.”

It’s a matter of trust given, received and appreciated to create an environment in which both builders and customers genuinely care about the outcome of the roof. 

“Door County has been good to us,” Chewy said, “so we want to return that.”

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