Why start a new island business?

Chebeague has always taken care of itself. When the mainland threatened to close our school, we became our own town. We are a people who look after one another.

But that’s gotten harder.

We are simultaneously the newest town in the state of Maine, and — with a median age of 60.4 years — amongst the oldest. Fewer families can afford to stay year-round. 60% of homes go dark every October, and every morning the ferry brings dozens of workers over from the mainland to do jobs that used to belong to people who lived here.

Over the years, some of my closest friends have bought seasonal homes here, to interweave their stories with ours. They love this place. They ask me how to go about finding contractors and plow guys and plumbers and auto mechanics and whether I think their roof will hold another winter. And seems — from where I’m sitting — more and more people are falling in love with this little slice of Casco Bay. 

I sit on both sides of this tension — 9 generations of honest, earnest island stewardship through my Hamilton bloodline, and more and more folks “from away” wanting to bring some of Chebeague’s magic into their family’s stories. 

But the real enemy isn’t any particular people group — it’s atrophy. Houses rotting in the dead of winter. Trades scattering to the mainland because the work here is too inconvenient and disorganized to make a decent living at. We’re at risk of properties being gobbled up by investors halfway across the world who couldn’t care less about honoring our island’s culture. Big money arriving on the island on a Monday morning, and leaving on the Friday ferry. Atrophy of our homes, atrophy of our trades, and atrophy of our year-round community’s viability. 

So I’m doing what little I can do to help, and starting an island business: Hamilton Management. We’ll help manage year-round homes and seasonal cottages, rentals for tradespeople and summer vacationers, project managing home improvement projects, large and small, and de-stressing the mayhem of shipping and storing building materials. And to do it all with the ease-of-use and peace-of-mind of a technology platform that benefits homeowners and contractors equally. 

To keep Chebeague’s properties as healthy as humanly possible, and keep the people who care for them living and working here.

First order of business is partnering with long-time island contractors to do this right from the get-go. This is the beginning of my transition back home. It's me putting my roots back down where they belong, once and for all. I intend to die on this island, the way eight generations of Hamiltons before me did. 

Well… seven, so far. (Sorry, mom.)

I'm not here to change Chebeague. I'm here to help take care of it.

Chebeague deserves to be cared for by its own.