Painting in Middlesex County Massacusetts circa 1997
Back in 1997, painting houses in Massachusetts was a different kind of hustle. There weren’t apps, no online booking forms, and definitely no sponsored Instagram posts. If you wanted work, you had to go find it — and that’s exactly what we did.
The Original Simple Painting Grind
The company was called Simple Painting back then. No fancy branding. No big crews. Just a couple of guys, a car full of drop cloths and ladders, and enough determination to fill a five-gallon bucket of primer.
We didn’t have leads. We had flyers.
Real, paper flyers. We’d design them ourselves — black and white, bold headline, bullet points, and a tear-off phone number at the bottom. Then we’d drive town to town, street to street, stuffing those flyers into mailboxes, screen doors, fence gates — wherever they’d stay dry and visible.
No Job Too Small
We’d spend hours out there in the car, mapping out neighborhoods, looking for homes that needed a touch-up, a full repaint, or just some honest help. No job was too small. If someone needed their porch railings scraped and painted — we were there. If a landlord needed a turnover done over the weekend — we figured it out.
And you know what? It worked.
People started calling. At first it was just one or two a week. Then five. Then ten. Before long, Simple Painting had a full calendar and no room left in the day for flyer drops. Word-of-mouth kicked in, and neighbors started talking. “You know those guys who left the flyer in the mailbox? They did my back deck — came out great.” That kind of momentum doesn’t come from an ad budget. It comes from showing up, doing the work, and being damn good at it.
From Rust Buckets to Reputation
1997 was gritty. It was real. We worked out of a rusty van with a busted ladder rack and just enough tools to get through the job. We’d wrap up late, run to the hardware store before it closed, then crash for the night with paint still on our hands.
But we were building something.
Simple Painting wasn’t just a name — it was the philosophy. Keep it honest. Keep it affordable. Do it right the first time. And treat every house like it was your own mother’s.
Looking back now, that first summer of driving house to house with a box of flyers might’ve been the best thing that ever happened to us. It grounded everything. It showed us what it meant to earn a client’s trust, not just their check.
Today the name has evolved, and the business has grown — but that 1997 foundation still runs through everything we do.
Because good paint fades eventually — but reputation doesn’t.
