THIS PROFILE IS BROUGHT TO YOU BY
OKUN SERVICES: WINDOW AND GUTTER CLEANING,
SERVING SOUTH BERKSHIRE COUNTY AND BEYOND.
NOW BOOKING FOR OCTOBER.
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Ted Okun and his partner Michelle Kaplan, of MishMash productions, both grew up in Canton, Massachusetts, and although their brothers were best friends, they didn’t meet until their early 20s. Since then these kindred spirits have been going where the wind has taken them, out west, back east, and finally here in South Berkshire County.
Okun went to work directly out of high school in a union carpentry-shop job before joining AmeriCorps’ NCCC (National Civilian Community Corps), for which he was based out of Denver and did ten months of trail work, built with Habitat for Humanity and did FEMA outreach for Arkansas and Texas.
After AmeriCorps, he and Michelle worked on organic farms through the WWOOF (Willing Workers on Organic Farms) program, hitchhiking up the West Coast starting in San Francisco and farm-hopping for months. A homesteading stint brought them to Pennsylvania, which is where Ted got seriously into bread baking, partly inspired by his baker great-grandmother and also by Tartine author Chad Robertson, who got his start with Richard Bourdon, our resident baking celebrity and owner of Berkshire Mountain Bakery.
That connection is what drew the couple, in 2012, to Great Barrington.
Okun and Kaplan house-sat and camped for a while in a friend’s backyard before settling into an apartment, and while he, in keeping with his WOOFing roots, moved here without a confirmed job, he ended up at the bakery, where he stayed to make bread for three years, while also working for fermented food company Hosta Hill, which has since shut down. Then, seeking to change things up, he transitioned into house painting. He found more lucrative but also much more physically grueling.
So Ted Okun eventually shifted toward first gutter cleaning and then to the addition of window cleaning. He started Okun Services business in 2018 with just himself, and has grown out over time to employ three additional full-time employees. The work is seasonal, with intermittent busy seasons and light seasons. After the burst of December work he takes the winter off so he and Michelle can head to Florida to stay with friends and family and escape the cold.
The business stays mostly close to home, covering Great Barrington and Sheffield, but ranges as far as Canaan, Connecticut and Pittsfield.
A big part of the appeal of gutter and window work, Okun says, is getting to see Southern Berkshires up close. He gets to drive down out-of-the-way driveways he’d never otherwise notice and see the quirky details that distinguish homes and and the unexpected commonalities that united them. He’s started a photographic collection of the turtle statues he’s found at more than half a dozen front doors.
“I wondered does that mean something or is it just a coincidence?” Okun mused that the turtle might even be a fitting mascot for his business, given how it’s grown: “slow, steady, gradual.”
Business growth has come mostly through word of mouth, the local community Facebook/board, and organic Google search rankings rather than paid advertising. It helps, too, that Okun makes a side gig of doing informal community favors like helping folks shovel their walkways and remove window AC units.
Outside of business Okun has been active in the Great Barrington Rotary since Covid, and now serves on the speaker committee. (He’s pleased to have introduced the club to the Berkshires’ own turtle rehabilitation specialist, who brought in some patients for show and tell.)
What animates Ted Okun most isn't the liveable schedule or his company’s growing success, but the responsibility he feels for the three men who depend on him for income, one of whom has a three-year-old child he has never met. Paying his employees well is one of the pleasures of the work. “It’s another part of the business I love,” he said. “It’s huge.”
Reflecting on his own family's history — his grandfather worked three jobs so Ted's mother could get an education — Ted draws a line to today’s crew: "I kind of feel like where my grandfather was, building a life for his kids."





Thanks for the wonderful write up on my business! Folks can contact me at 413-854-4949 or visit my website: OkunServices.com