Henry Dreist’s week has a shape, and it follows the map. Mondays and Tuesdays he works the beaches. Wednesdays he moves to the north side, then Avondale and the Five Points area. Thursdays he is in Orange Park and St. Augustine. Thursday afternoons, Fridays and sometimes Saturdays, he heads for the west side.
He doesn’t promise customers a time of day. He promises a stretch of days. “I might be a day early or day late, but usually it’s a three-day window,” Dreist says. Only a few of his customers, such as restaurants, get a set hour. Everyone else gets washed when the route reaches them. Florida brings plenty of storms, and he tells customers not to expect him when it’s pouring.
The route is not entirely his own invention. Dreist worked for one of his old bosses for about 14 years. When the man retired, Dreist took over his work and went back to the older man’s original schedule. “I just kind of blended mine into his,” he says.
He learned the trade young. Dreist started in high school, around 1987, working for his uncle. He has been washing windows since he was 16, and he quit school to do it. He was working for another window cleaner when he went out on his own in 2008. His wife wanted a business of their own, he says, so they started one.
The first year was slow. Dreist says he had no idea the country was in a recession; he only knew the days were thin.
The company went through several names, Papa’s Window Cleaning among them, before it became Henry’s Window Cleaning in 2017.
Most of the work is commercial, about 90 percent by his count. According to the company’s website, that means storefronts, offices and other commercial properties. “I think I’m mostly known for doing commercial,” he says. He used to do a lot more residential work and still takes it on, and the website lists screen cleaning as well. One customer quoted on the site says Dreist has cleaned their windows for 15 years.
The website names Clay, Duval and St. Johns counties as the territory, with Middleburg as home base. Dreist says he usually works within a 60-mile radius.
There is no crew. “It’s just me. I’m a solo act right now,” he says. He plans to hire employees as he gets older, though he is frank that the hard part will be teaching them. “I know how to wash windows,” he says, “but I’ve never been really good at training people to do it.” When he shows someone how, he admits, he usually ends up doing the whole window himself.
He has tried bringing in help before, and it never stuck. “Nobody likes window washing as much as I do,” he says.
He does think about who comes next. Dreist has grandchildren now, and one of them might take an interest in the work. “I’m planning to hand it down,” he says. “I just don’t know who yet.”