In 1986, after completing high school, Cutting Edge founder, Randy Van de Mosselaer, took a summer job at a lawn care company called Student Lawn Service to help finance his university education in pursuit of a business degree. Following graduation in 1990,  Randy decided to start his own business, The Cutting Edge Lawn Service. Initially, Randy ran the business from his parents' garage with a couple of trucks and some used lawnmowers and trimmers, employing family and friends in the process. The business transitioned from seasonal to year-round services with the addition of winter snow clearing.

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As the company expanded and diversified its services, the need for more space became apparent. Cutting Edge initially operated from Clarence Avenue in Fort Garry and later moved to their current location in the Fort Garry Industrial Park. From just two trucks, their fleet grew to four, then eight, and more.

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In 2004, the business incorporated professional fertilization and weed control into their range of services. Presently, Cutting Edge serves residential and commercial properties across Winnipeg and surrounding areas, including notable clients such as RBC, McDonald's Restaurants, Rivard Group, Bee Clean, Main Street Project, Krevco, as well as various condo developments and strip malls. Cutting Edge boasts top-of-the-line equipment, a dedicated staff with over 15 years of experience, and pride in offering professional services at competitive rates.