“I’m so relieved that I found a local, reliable, experienced, and affordable service to clean the clogged and leaky gutters on my old house. Many thanks to Okun for a job well done – let it rain!”
— Jennifer T.
Ted Okun, owner of Okun Services, promises his customers that “all of the debris within the gutters will be removed, and the downspouts will be cleared and ready for rain.” The process is pretty straightforward—either removing the leaves and other gunk by hand or using a blower. Window cleaning can involve the traditional squeegee and soap solution or a newer technology, the water-fed pole, involving a three-stage filtration system. After removing all the minerals from the tap water, the water runs through a tube up the telescoping pole to the soft-bristled brush at the end, which gently scrubs the glass. And, since there are no minerals in the filtered water, the windows dry completely spotless.

A diverse background—including sourdough breadmaking and house painting
Okun, who grew up in Canton, Mass. (south of Boston), recalls walking home from the bus when he was in middle school and being asked by an elderly neighborhood man, “When are you gonna mow my lawn?” He had never mowed the man’s lawn before, but started doing it soon after. That gradually led to more jobs. “When I was 14, my dad took me to get my worker’s permit. My mom was a nursing home administrator, so I started working for $7 an hour after school, on weekends, and in the summers with the maintenance department there,” he adds.
In 2012, Okun moved to the Berkshires with his girlfriend, Michelle Kaplan, a radio host and DJ (@mishmashwbcr). “We had been traveling around with WWOOF [a global organization dedicated to supporting sustainable organic farming] for a while and were ready to settle down. My brother had graduated from Bard College at Simon’s Rock in 2006, so I was familiar with the area,” he says.
Okun happened to also be a sourdough breadmaking enthusiast at the time, having spent much of his childhood baking with his grandmother. And as a follower of Tartine Bakery in San Francisco, he was eager to work with renowned sourdough expert Richard Bourdon, who had famously taught Chad Robertson, the owner of Tartine, the craft. When an opportunity arose to work at Berkshire Mountain Bakery, Okun jumped and remained there for four years.
However, making ends meet on a baker’s wages wasn’t easy, despite also working part-time for Hosta Hill and joining the ranks of those who do the “Berkshire shuffle” by taking on multiple odd jobs, including a six-month house-sitting gig. That kept them going for a while, but eventually, working in the food industry proved unsustainable, and they both sought out different jobs to afford their own apartment.
“I was racking my brain, trying to think of something I could do when Jill Fleming of BerkCirque asked me if I wanted to paint her apartment. My friend Eric Reinhardt, who was a painter [and is a well-known musician], showed me the ropes,” Okun shares. With his painting skills honed, he applied for a business certificate at the town hall, then visited Wheeler & Taylor to obtain liability insurance, and subsequently launched his own painting business. After three years, he decided to shift the operation to gutter cleaning.

“Painting a house by yourself is daunting,” he admits. “It’s lonely—I’d never have made it without ear buds.” It also often involved being around toxic chemicals all day. “Once I cleaned my first gutter, I thought ‘This is fun, satisfying work!’ I added window cleaning two years ago, because it was something that paired well with gutter cleaning and involved similar equipment, so it was a logical way to get more work.” He eventually had the means to hire helpers.
Gritty work, with a good crew
Asked to pinpoint the key to his business success, Okun answers, “The big thing for us is that the crew is personable. Often, when they leave a site, I get a happy message from the client asking, ‘Where did you find these guys?’” His crew includes Sean McTeigue and Ethan Glenn, who work three days a week, and Katarina Samora (a previous customer), who now works as a part-time executive administrative assistant. “It’s nice to be able to delegate certain tasks and not have to do them at the end of each day,” Okun admits, adding that Samora’s husband is currently helping him design the new website.
Okun describes gutter and window cleaning as “very gritty work” but notes that he likes going up ladders and getting dirty. “I’m very safety oriented. You get comfortable with it,” he assures. He also enjoys driving down remote back roads and working on beautiful homes.

Overcoming challenges and growing organically
His toughest lesson? “If I could have looked forward a few years ago and figured out how to organize my customers, respond in a timely way, schedule jobs, and do invoicing, that would have made things easier,” he acknowledges. Although it can be difficult to manage all those tasks simultaneously, he now utilizes the Jobber app—a field service management tool designed to help service businesses manage their day-to-day operations from anywhere—in addition to having a bookkeeper, Susan Ingersoll, and Samora helping with administrative duties.
Okun also points to the Massachusetts Small Business Development Center in Pittsfield, which is funded by UMASS Amherst, as providing tremendous support. “They were incredibly helpful, mentoring me through comfortable and uncomfortable things and meeting with me as often as I needed,” he says, adding, ”and I still meet with them.”

In addition to staking lawn signs and placing ads in the Southern Berkshire Shoppers Guide, Okun’s business comes through word of mouth and Google searches. He also posts on town community boards and the Next Door app. More recently, he has begun sponsoring local community organizations, including Berkshire Pulse, Blue Rider Stables, the Great Barrington Farmers’ Market, and the Railroad Street Youth Project, where he also serves as a mentor. “I like putting the money into organizations, instead of into ads,” he says, noting proudly that he now sponsors a local team through Great Barrington Little League.
Is the work sustainable? Although there is no shortage of homes needing gutter and window cleaning, the work is seasonal, so Okun is trying to figure out how to maintain a consistent workflow for supporting his crew year-round. And while the usual hours are 8 a.m. to 4 p.m., the team typically works from dawn to dusk in the fall as people are making the final push to clean up before winter. However, he knows a nice break is waiting for him. “Michelle and I usually go to Florida for February and March,” he says. “I am very grateful to have a successful business and a simple lifestyle where we can afford to do that.”

Giving back, in the spirit of community service
A few years ago, Okun conceived the idea of offering free air conditioner installation and removal to seniors and those in need. “It usually means stopping by for 10 minutes or so,” he says. He is also involved in several community-serving organizations, such as the Rotary Club and Literacy Network, and was recently approached to join the South Berkshire Committee at Berkshire Taconic Community Foundation. “You can do good work on your own, but when you have a club or organization behind you, the good gets amplified,” he emphasizes.
Okun credits his late father, who was always willing to help others, with instilling in him an impulse to serve. “He was a Rotarian,” he says. “I keep a coin in my pocket at all times that reminds me of the Rotary test [created by Rotarian Herbert J. Taylor in 1932 to guide ethical conduct in business and personal life]. It consists of four questions: Is it the truth? Is it fair to all concerned? Will it build goodwill and better friendships? Will it be beneficial to all concerned?”

“I like to joke that I don’t need a lot of stuff for this work. I could post a picture of a ladder, a hose, and a bucket and rags with the caption ‘Business for sale.’” But not everyone could build a business with as sturdy a foundation.
“Life is for service,” Okun states, adding a quote from motivational speaker and bestselling author Zig Ziglar: “To get what you want, you just need to help enough other people get what they want.”
