Next Gen entrepreneur thrives on Shelter Island
While there’s a common refrain these days about the next generation moving off the Island because of the lack of affordable housing or work opportunities, Chandler Olinkiewicz is counting himself lucky to be one of the exceptions.
He’s coming up on four years since he began his own business, aptly named NextGen Construction, and he says, “Being my own boss gives me more options in life than I ever thought I would have.”
Mr. Olinkiewicz grew up on Shelter Island, then went to Alfred University and spent some time in New York City and New Orleans before returning to the Island. He spent time working in his father, James’ construction business and learning the trade.
While he majored in communications in college, it seemed the apple hadn’t fallen too far from the tree, for while there he busied himself building a three-level playhouse space for the freshmen and sophomores to use.
“I took 130 rolls of duct tape to construct a net between the structures for students to lie on,” he said, providing a venue for college students to enjoy one of their most popular pastimes.
He was back on the Island when the COVID pandemic struck, and a number of people seeking safe space moved here full time, enlarging their summer homes or building new ones. “Most other contractors were being inundated with large builds,” Mr. Olinkiewicz recalled. “I saw a window of opportunity to take on work doing some smaller scale projects and repairs.”
Getting his foot in the door that way has paid off, since he now benefits from word-of-mouth recommendations from satisfied clients. “I do everything from repairs to full renovations.”
A recent recommendation brought him to the Parsonage of the Unitarian Church in Southold, working on rebuilding it to become a community retreat center.
Not long ago, Mr. Olinkiewicz worked on an interesting project for the Custer Observatory in Southold, where visitors can use telescopes to view the sky. He constructed roof doors with a track and pulley system to open and close for access to the telescopes.
Here on the Island, he’s got the connections he made growing up and going to school here, as well as those his family built through their own businesses. His grandfather, Paul, ran Books and Video in the Heights, and his father, James, has had a construction company for years.
While word-of-mouth and being part of a small community has served him in growing his business, it’s also been reassuring to his clients to know that he will be available on the Island after a job is completed, and come to help out when problems arise even in the middle of the night. Long after other contractors have taken the ferry off the Island at the end of the day, he’s here 24/7 to respond.
“I’ve even shoveled snow,” Mr. Olinkiewicz said with a smile.
The 31-year-old entrepreneur has one full time employee besides himself, sub-contracting out aspects of a job like electrical work. For bookkeeping and administrative work, he’s turned to a friend, Olivia Garrison, whom he knew from high school, and who helped him by editing his papers while he was in college. Now they go through the paperwork at a weekly meeting. They formerly dated, and are now friends, living on a small island where it’s important to keep and nurture relationships. The two own three dogs together, Cavalier King Charles Spaniels named Pork, Mistress Perona, and Kumacy.
Having his own business has paid off in many ways, but he’s honest about the toll it can take in terms of stress when the responsibility is all on your shoulders. He knows there are some other young entrepreneurs on the Island who face the same pressure, and suggests they could benefit from getting a group together from time to time to compare notes, provide mutual support and learn from each other’s experiences.
About a year ago, Mr. Olinkiewicz was able to buy his own house on the Island, where he raises turkeys, ducks and 100 chickens — “providing enough meat for me and my dad” — and so many eggs he’s able to share them with friends and clients. He’s planted 26 fruit trees to yield apples, peaches, cherries and elderberries.
He takes pride in the self-sufficiency he’s developed, “transforming a pocket of the Island” into his own place.
“I never look back,” he said. “I just keep going. Once I took the leap from working for others to working for myself, I got the opportunity to build my future my way.”

