Brian Williams says ‘yes’ a lot. It’s a powerful word. ‘Yes’ opens doors. It expands what we see and think. It invites people into our lives. So, in many ways, Brian is perfect for the job he does – barbering in Waldoboro. And Dark Harbor Waldoboro is a ‘yes’ kind of place. Yes, you need to make an appointment to get a haircut. But anyone is always welcome to drop in, shoot the breeze and leave. And yes, politics is off bounds, but there's motorcycles, sports, and bourbon to heat up a conversation. Brian also loves what’s happening in Waldoboro these days from the Inn to Medomak River Park to seeing all the visitors coming to The Waldo, even if it means losing his own seat at Narrows Tavern. Saying ‘yes’ makes you generous.
When I was a kid, I had no plans of what I wanted to be. My dad, before he got incarcerated, did carpentry and roofing and all that stuff. And he was a mechanic, so I had my own life skills as a mechanic and carpenter.
So, yeah, grew up right here in Waldoboro, went to Miller School, went to AD Gray. We lived in a trailer up behind Stetson & Pinkham (on Rt. 32, past Wagner Bridge), and Mom was working at Sylvania, I think from 1995 until they closed.
When she committed suicide, that was pretty rough at fourteen. It was one of those things where you mature faster than you want to. But after a while, it became one of those things where, “Life is kinda what it is.”
So, I went to Rockland to live with my grandmother, went to Rockland High. But I was a social butterfly, going to high school to hang out and be with my friends, and not doing my homework to get the grades I should have gotten. But with my grandmother’s help, I graduated like I was supposed to. I graduated on time.
I was one of those kids that had to get out of Maine, though. I followed some buddies and went to Wilmington, NC and got a job selling cars. I did alright and went to San Antonio where I hung out with friends until my money ran out, and then at Home Depot picking up day work. I ended up running a whole roofing crew.
But at some point, I realized, “Maine’s really not all that bad.” So, I came back, met my wife, and bought a house here. I was back in my hometown.
I started at a landscape company in Rockland; stayed for about three or four years. Then one day I got a phone call, and my buddy goes, “Hey, looking for a new job?
I wasn’t, but it was a huge pay increase, so I went. I was at Journey’s End Marina for a year or so, and then I went over to Johanson Boatworks, and that’s where Al Rainey really honed my painting skills. Then I got to the point where I hated being on my knees all the time.
So, I went back to landscaping, but my own business, doing that in the summers, and painting boats on my own, in the winters. And when I got done working on boats at the end of the day, I’d hang out at Dark Harbor for a beer before heading home.
Well, Sam Weldon and DJ Jones asked me if I wanted to join them. They were moving to Main Street in Rockland, and I’d kept saying no because I didn’t know really what I wanted to do. But then, I was supposed to go to dinner that night with the wife, and I didn’t have a nice pair of jeans. Mine always had paint on them or a tear because I worked on boats. And that was kind of my deciding factor: “I’m going to have nice clothes and not have to worry about not having a nice pair of jeans.”
So, I started over in 2022 in Rockland. I did an apprenticeship under Sam, no barber school, and for the first couple of days, I just kinda watched, and Sam’s looking at me, explaining stuff to me, and something clicks and goes, “You’re not really learning much, are ya?”’
“To be honest, Sam, not really.”
So, he says, “Alright. I’m going to put you on the schedule.” And he did, but don’t get me wrong – for the first three or four months, it was a struggle. I made my share of mistakes. And then we fixed them.
It’s kind of funny how Dark Harbor ended up in Waldoboro. We’d been looking to expand, to open a new place. When they found a possible space in Waldoboro, I just shook my head. I didn’t think we could draw enough business there to stay busy.
But when I went to see the space, I realized it was Bob’s old shop, the barber we called Bob the Butcher because you always got the same haircut no matter what you asked for. And I chuckled and thought, “This might work out,” because I remembered that before Bob, there was this guy here called Hotdog Benner. So, I was pretty sure that from the 1950s thorough the mid-90os that this had been a barbershop.
Well, we struggled for the first two months. Thankfully, I have a loving wife that works her butt off, so we survived, but it was hard. I’d gone from 80 to100 people a week to only six people.
Then, they ran an ad in the paper for us, and people started realizing we’re out here. All the guys that would go to Rockland, they found out we were here. So now we’re pulling all the people from Warren, Cushing, Union and the Washington area, and they’re like, “We don’t have to go to Rockland no more, we can just come to Waldoboro.” And after Bruce Soule closed down, we had a big influx from him too.
And they’re the clientele I think I enjoy the most. We’ll be super busy, and they’ll come in wanting to get in line for a haircut, and then leave all pissed because we don’t do walk-ins. One guy, you could see him stalk back to his car and just sit there for like ten minutes. Then he comes back in and says, “I guess I got to make an appointment.” I tell those guys they’re welcome any time to come in, have a beer or soda, and shoot the breeze.
You get a lot of different people here. The hardest is probably the guy that doesn’t talk or explain the haircut. They don’t give you any expression of how they want it, and I’m, “We need a little more back and forth here.” I’ll ask them a hundred questions like, “Do you want shorter or longer?”
They’ll be, “I don’t know.”
And when you get their haircut done, they’ll say, “It’s kind of short.”
And I really worked to give them a happy medium. But I’ll just say, “Next time you’re in my chair, how about we give you a little longer haircut?”
I really wish I would’ve found this ten years ago. It never crossed my mind to be a barber. No one ever expected me to be a barber. I had no intentions ever in my life. I did it because Sam and DJ gave me the chance, and I wanted to try it out.
And now I have someone new in my chair every half hour.
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