Editor’s Note: This Edge Staff piece has been submitted by Berkshire Hills Regional School District Communications Coordinator Sheela Clary.
Great Barrington — Attention South County homeowners: If you are still in need of a landscaper/lawn mower for this summer season, there is a local high school senior who still has a few openings. Ian Drucker, Monument Mountain class of 2025, is currently managing 115 snowplowing jobs and about 60 lawn-mowing gigs, with room to grow.
He started out slow, as a first grader on a four-wheeler plowing neighbors’ driveways on Kalliste Hill in Great Barrington, but things accelerated more recently. “My business, my real business,” he explains, “started up in the last two years.” Ian is so busy he no longer has time to help dad in the family business, Barrington Outfitters, downtown Great Barrington’s place to go for good shoes, clothing, and outdoor furniture, among other things.
Along the way he also went to work during the summer for Kevin Pieropan of Pieropan Property Management, and then interned with that company two days a week up until this past November. He credits that experience with teaching him a lot of what he knows. By now, though, he says, “I have too much work myself, so I can’t work for him.”
Ian’s mom Hilary Drucker, his central business partner, recalls Ian’s beginnings and how he doubled his driveway workload, and expanded his geographical reach, once he received his learner’s permit. At that stage, he started using a truck he had bought himself, but which mom and or dad would have to drive with him. Things really took off junior year, with the achievement of his driver’s license. Then, she adds, “He ended up with about 50 to 60 driveways.”
Ian is quick to thank his school’s internship program, and the help of his guidance counselor, Michael Powell, especially, for honoring his work-related goals. “With people who don’t enjoy being in school all day, they’re pretty good about that.”
Powell, for his part, says that Ian did not go about his choices recklessly. “He was not whimsically making decisions,” Powell says. “He consistently communicated his goals starting when he was a freshman and was determined to meet them. But what I admire most in Ian was that he never closed the door on other ideas. He was open-minded about options and gradually became more certain of his path as he went through high school.”
Along that path, Ian has learned skills that will serve him well regardless of which directions he might choose to take in the future: He is comfortable negotiating professionally with clients; he knows how to price a job using on-the-ground factors; he sees the high value people place on reliability; and he knows that word of mouth is far and away the most effective form of marketing.
“I put out like one post on Facebook I think, but,” he says, “that doesn’t work.”
He has also learned valuable lessons about supply and demand, lessons that most teens won’t be exposed to until Econ 101, and then only in textbooks. Ian saw firsthand: “There’s a lot more people that mow around here than plow,” so he jumped in to fill the void. His plowing clients include 20 commercial parking lots, the best kind, he says, since they require the most consistent maintenance. He and his crew plow such familiar spots as Four Brothers Pizza, Najis, behind the Barrington House, and the Marketplace locations in both Sheffield and Great Barrington.
How much has he earned? Enough to get himself a 2025 GMC pickup as a work vehicle. He has established saving goals but also recognizes the need to reinvest profits back into the business, saying, “I have to have good equipment.”
After high school, Ian intends to stick close to home and see where his business can go. Right now, he is juggling classes in the early morning and eight work hours—or until the sun goes down—on top of that. After graduation? The sky is the limit.
