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Need anything hauled, dumped, loaded, removed, leveled or filled – Roll With It can help

The four-year-old, Freedom-based business is owned and operated by Andy Kluck

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February 21, 2024

FREEDOM — When Roll With It, LLC, a dumpster trailer and landscaping company located in Freedom was a fledgling business, Owner Andy Kluck said he learned an important lesson — the hard way.

“My first year, I had somebody who wanted me to take some gravel away for them, and they told me it was like three yards, which would have been plenty within the weight capacity of my trailer,” Kluck said.

However, Kluck said when he got there to pick it up, he found the container filled to the top.

“It ended up being 35,000 pounds of material, and it was way more than the trailer could handle,” he said.

Roll With It’s 15-yard dumpster trailers can hold up to five tons, or 10,000 pounds, which Kluck said usually is more than enough for the average homeowner’s typical task.

But the gravel overload blew out two tires, which ruined the trailer’s brake wiring and broke the hydraulic lift ram, as well.
Kluck said he learned a lot from that experience, which has helped the four-year-old business grow.

One arm of the business rents out dumpsters on wheels for roofing projects, building renovation, construction, landscaping projects, real estate cleanouts and junk removal.

Kluck — who has been a landscaper for almost three decades — said in addition to dumpster trailer rental, Roll With It offers landscaping services, such as pathways, paver patios, retaining walls, landscape lighting and lawn repair or establishment, as well as landscape design and materials delivery.

The company, he said, can also provide skid steer service, for such tasks as backfilling foundations on new construction.

Down but not out
Though Kluck said the beginning mishap — which cost him a couple of thousand dollars in repairs and weeks of downtime — left him a bit discouraged, he said he learned from it.

“I didn’t have any rules set, and I didn’t know any better at the time,” he said. “I had to deal with it.”

At the time, he only had two trailers — one he rented out and one he primarily used for the landscaping side of the operation.

Starting with just two dumpster trails, Roll With It has more than doubled its fleet in the last four years. Submitted Photo

So, it left him one dumpster trailer to try to juggle between his landscaping needs and requests to rent it out.

Kluck said it was tough having to say “no” to prospective patrons.

“I was trying to build a new business,” he said. “You’re trying to get your name out there, and then I’m turning people away — it wasn’t making sense.”

After juggling the one trailer between both sides of the business, Kluck said he knew he had to buy more trailers.

The additional three trailers, he said, helped to ease the scheduling angst and increased the company’s capacity to take on new business.

Learning from his mistake, Kluck said he implemented guidelines and wrote some fine print.

As time passed and Roll With It expanded its customer base, Kluck said he implemented several parameters — including delineating what can and can’t go in the dumpsters (and how much of it).

Electronics, he said, for example, should be left outside the dumpster or placed last, near the door, so they can be the first items to be unloaded and segregated at the waste transfer station.

Kluck said the waste transfer station at the landfill is where items that are recyclable or salvageable are separated before the load heads toward the landfill.

Certain items like electronics, TVs, computers and tires carry extra fees beyond the weight.

“If they have them (electronics, computers, etc.), it’s fine, but I have to charge extra for them because the landfill charges me on top of the weight,” Kluck said.

However, he said Roll With It can’t haul away everything.

Items not accepted include propane tanks and pressurized containers, items containing asbestos, chemicals, paint, motor oil, pesticides, medical waste, flammable or explosive material and a variety of other items listed on the Roll With It website (

Kluck said because of the danger of overloading, the company also can’t take dirt, sod, concrete, brick and other heavy material.

User friendly
Kluck said he chose dumpster trailers instead of regular flat-bottomed dumpsters for a handful of reasons — the biggest reason being they’re easier to maneuver in and out of a driveway or on and off a site.

“It’s quick in, easy out,” he said.

The dumpster trailers have rubber tires, Kluck said, so they don’t scratch a customer’s driveway or gash up their lawn.

The dumpster trailers, he said, also have easily accessible doors — meaning the user can walk in and set their debris right in the container, rather than trying to hoist heavy items above their head and over the walls of the dumpster.

The dumpster trailers also have ramps, Kluck said, to make maneuvering bulky items into the container easier.

“Some people think they look a lot nicer than if they have a (conventional) dumpster in their yard,” he said.

Origin story
Kluck said he worked for 24 years for a landscaping company, Maple Leaf Landscape & Design, in the Town of Freedom — starting at age 18.

After his former boss, Cal Stapel, retired and closed the business a few years ago, Kluck said he took on landscaping jobs for some of their former clients while he figured out the next chapter of his life.

He said he wasn’t sure whether he wanted to continue with landscaping — already into his 40s and recognizing he couldn’t be trundling rolls of sod around forever.

Kluck said he came up with the idea for a dumpster trailer rental business indirectly, via YouTube, when he saw a video of a guy who made a good living renting out dumpsters.

He said it sounded like it could be a viable future strategy for a 40-something-year-old landscaper or at least a source of revenue during the off-season months.

Kluck said the original plan was to do that full-time.

“But then I knew that was probably going to take a while to take off and be enough income to support my family,” he said. “So, I was going to supplement it with landscaping because that’s what I knew, and that’s what I did.”

Kluck said his parents helped him out with some funding to purchase his first dumpster, as well as got a bank loan to get things rolling, and it went from there.

He launched Roll With It in February 2020 — then the COVID-19 pandemic hit.

His plan to purchase three trailers at the beginning was cut to two, and because of supply chain struggles, Kluck said the prices of dumpster trailers had skyrocketed.

In addition to dumpster trailer rental, Roll With It offers landscaping services, such as pathways, paver patios, retaining walls, landscape lighting and lawn repair or establishment. Submitted Photo

He said his former boss, Cal Stapel, let him rent out his old shop building — an old barn with space to store his landscaping equipment and a parking lot large enough for his dumpster trailers — and gave him a deal on rent.

Kluck said it was a big help in getting him back on his feet with the landscaping service.

“I hired Andy when he was a young little dude,” Stapel said. “He could do anything — he could put in lawns, he could do shrubs, he did brickwork, he built decks for me.”

A father of two boys himself, Stapel said he considers Kluck to be a third.

Last year, Kluck said he was able to buy Stapel’s shop building.

A time and a place
In winter, Kluck said there’s not a whole lot of landscaping going on, but people are still doing other things that call for dumpsters — such as remodeling projects, cleaning out a house, putting on a new roof and decluttering.

He said his wife, Alana, manages the company’s website, blog and social media platforms, which he said is a huge help.

“I would be nowhere without her,” he said. “My exposure would be zero without her talent.”

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