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Meet Trip Howland, Answer Me This! Winner

Construction Solutions Trip Howland
February 22, 2021

By Karen L. Edwards, RCS Editor.  

Each week someone wins a prize for answering a question, next week’s winner could be you! 

One of our most popular giveaways is sponsored by Gibraltar Building Accessories as part of their ‘Construction Solutions’ campaign designed to supply feedback from contractors to help them continue to innovate. We think it’s popular because it is so easy to participate. Simply answer one simple question and you’ll be entered into a drawing for a prize. If selected as the winner, you’ll get your choice of a free pizza, an RCS Box of Love or a box of donuts. 

This week’s winner has a long family history in the roofing industry. “My Grandpa started subcontracting for Hamlin Roofing in North Carolina in 1969,” Trip shared. “His three sons worked under him and each of them ended up starting their own roofing businesses. I began working for my Uncle Philip when I was just 14 years old.”  

Trip worked with his uncle throughout high school and college. He realized he had the potential to make more money in roofing, so he started full-time after finishing school. In 1995 his uncle opened JDM Roofing in Fayetteville, North Carolina where Trip was able to gain invaluable experience in commercial roofing.  

“We did a lot of school roof work back then installing TPO, PVC, Hypalon and EPDM. We were Firestone Master Contractors in the late 90s and early 2000s,” said Trip.  

After a vacation to Costa Rica in 2004, Trip worked for two years at Bradco Supply before moving to take a role at Coastal Commercial Roofing. He eventually moved to work for GR Hammond as a project manager and estimator, where he traveled to jobsites in other states. “We had work as far north as Boston, as far south as Miami and as far west as Fort Campbell, Kentucky,” he explained. “We had a lot of military work and did a lot of multifamily housing.”  

In 2019, Trip moved back to Myrtle Beach, South Carolina to help his grandmother care for his paralyzed uncle. “I found a job at Monarch Roofing as a field manager, but then I took over as commercial division manager once they realized my abilities.” 

Trip said that the next generation looking for a solid career should consider roofing. “If you get out there and learn it from the ground up you can get to a place like me, managing a division and making six figures plus incentives,” said Trip. “It’s a great career and it’s always going to be there because people will always be building and roofing.” 

Want to try to be next week’s winner? Submit your answer to the latest question here.  



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