Southbury’s Quiet Entrepreneur Homer Bennett Celebrates 60 Years

During his post-World War II military service, Homer Bennett sat in the precarious position of tail gunner in a fighter bomber flying from what was at the time the largest ocean-going craft on earth, the USS Franklin D. Roosevelt.

When he returned to his home town of Southbury, a growing suburban community tucked into the southern fringe of the Litchfield hills, he did what a lot of young returning veterans did — bought a car and got himself a job to pay it off.

“I came back from military service and got a job at a carpenter shop in Waterbury,” he told The Newtown Bee. “That lasted 18 months, until I paid off my car.”

From there, Mr Bennett switched to selling farm supplies, becoming so adept that he was eventually tapped to train other new salesmen. He even opened a wholesale supply operation, but abandoned it almost as quickly.

“I didn’t like that very much, so I took a job at Old Hundred Ice Cream and got into garbage hauling a couple of days a week,” he recalled.

Mr Bennett bought one of his first garbage collection routes in Oakdale Manor for $350, but balked at the $1,300 price tag the seller fixed to his garbage truck. Instead, he picked up a Model A Ford dump truck for $85 and began acquiring other trash routes, eventually amassing routes throughout Southbury and parts of Oxford.

“I’d deliver ice cream Friday, Saturday, Monday and Tuesday — and did garbage hauling for a bunch of the lakeside summer cottages and other homes on Wednesday and Thursday. I could do the whole town with one vehicle, but once I picked up routes in Oxford I started hiring other people to help.”

Around that same time, Mr Bennett started expanding his entrepreneurial pursuits by building septic systems in his mother’s barn. He also bought a backhoe and started installing the septic tanks he was fabricating in his spare time. He called his business H.L. Bennett Jr, Inc.

For the next 13 years, he would supervise septic installations and garbage collections by day, heading out on the road doing his ice cream deliveries at night.

“The ice cream job was great because it provided me with medical insurance for my whole family, and a company car they let me use for my other work during the day,” he said. During this time he also bought and paid off a small home on Main Street South, where Mr Bennett still resides for most of the year. (He spends winters in Florida.)

“By the early 1960s, business was going well, so I quit the ice cream route. We were making enough so I could cover our family’s medical insurance along with paying for coverage for my workers,” he said. He also began acquiring property around and behind his home, and began developing commercial buildings.

His first was a garage to house his growing fleet of trucks and heavy construction equipment. But soon after he began building the commercial buildings that would become Bennett’s Square.

Today, old and new clients will encounter his daughter-in-law Alicia handling the front end of his septic business, and his son Jay, who has been working by his father’s side since high school, handling the bulk of the field work on septic installations and repairs.

Mr Bennett’s other son, Kevin, has taken over the role of company owner, but is engaged in his own work as an architect and builder.

Long gone are the days when the Bennett family would manufacture the septic systems they would install.

“It’s much easier and less expensive to buy the equipment from a vendor. Then they just come and drop it in the hole we dig for the system,” he said.

He’s not an engineer by a long shot, but Mr Bennett prides himself on “learning by doing.”

“From day one I kept an eye on developments in the septic industry. I asked a lot of questions and studied engineering at night, pouring over system blueprints to learn what I needed to know,” he said. “The designers may be engineers, but I always knew a lot more about excavating and soil than they did.”

As he watched a burgeoning commercial district grow up around his small tidy home and Bennett Square, Mr Bennett quietly proceeded to serve his growing customer base. With 60 years under his belt, he’s also quietly earned a unique position among the area’s most long-tenured local businesses.

“I guess when you do something for 60 years, if you’re not the best,” Mr Bennett observed, “there’s something wrong with that picture.”

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