Meet Milwaukee’s Expert of the Month: Joseph O’Brien

Four Leaf Roofing and Windows’ president shares tips on home projects and finding the right contractor.

Joseph O’Brien; Photo by Boutique Photographer Linda Smallpage

JOSEPH O’BRIEN has been working in the home remodeling and construction trade since he was a teenager and has owned Four Leaf for over 25 years. We asked him to share his expertise here.

What advice do you have for someone trying to find the right contractor for their home project?   

Do your research. You want a contractor that has a history of good work. That means checking reviews, searching social media, interviewing them. One question that I don’t think people ask contractors enough is “Who are your suppliers?” It’s important to check with those suppliers and make sure the contractor is in good standing with them. That due diligence helps avoid mistakes. We’ve been around a long time, and we’re proud to have built that positive reputation with our customers and suppliers.  

What factors set a quality contractor apart?  

Whether it’s roofing, shingles, gutters, windows, the materials a contractor uses are crucial. We work with brands that will stand the test of time. You don’t want to go with the cheapest option. That’s like buying the cheapest car on the lot – maybe it sounds like a deal, but how long will it really last? You don’t want to take shortcuts that will come back to hurt you later. We know that a roof or new windows is likely one of the biggest purchases a customer is making for their home, and we respect that. We offer financing options for all our customers – they can enter their address on our website and receive an estimate, and then we’ll follow up with a physical inspection. We want to educate them about their options and help them make the right decision.  

Four Leaf Roofing and Windows

16855 W. Observatory Rd., New Berlin


This story is part of Milwaukee Magazine’s March issue.

Find it on newsstands or buy a copy at

Be the first to get every new issue. Subscribe.