Kamsack entrepreneur reflects on town’s evolution

He’s helmed a number of local business ventures in Kamsack over nearly 50 years, but whether he’s talking about playing for the 53rd Field Regiment Military Band or playing with a dance band at the Stoney Creek Hall for a local dance, Chester Olson’s face lights up when he talks about music.

“I can play the clarinet, accordion, saxophone, and the drums,” offered Olson. “In fact, when I was 13 years old, I made eight dollars playing for a dance band. It was so much fun and I could hardly believe I was getting paid for it too.”

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If dance band musician was considered Olson’s first casual gig, then his first official job would be recognized with the Saskatchewan Liquor Board in 1968. Olson was just 18 years old when he was hired by Vladimir (Laudie) Gregorash. During the five years Olson worked as a senior clerk, he married his sweetheart, Gladys, and together they had their first child, Shannon, in 1972.

The newlyweds wasted little time before buying their first business, the Texaco Highway Store, located at Highway No. 8 and Rhein Grid Road. At the time, the store was of service to 305 farm accounts. When he looks back at the way Gladys juggled the duties of mother, wife, and business woman alongside her partner and husband, Olson described his wife as “the hardest working woman I have ever known – and that’s true to this day.”

“The Texaco store was a precursor to a 7-11 store,” explained Olson. “We sold everything from staples to sausage, gasoline to barbed wire.”

Olson recalled the days of gas prices at 47 cents a gallon and cigarettes at 50 cents a pack, and said that their infant son practically grew up in the store. The young couple would run the successful store up until the day they sold it to Gary and Margaret Matechuk in 1976.

At this time in their lives, it may have been difficult to predict the many business ventures the couple would launch in the following decades. However, the town of Kamsack would come to know Olson and his family very well through the consistent services they provided to residents over the years.

In addition to running the Texaco gas station at Madge Lake, Olson would eventually open a bowling alley, a hamburger franchise, a confectionary, a laundromat, a video store, a bingo hall, an antique store, and a liquor store – all in Kamsack. One of the longest running business, Chester’s Restaurant, on Kamsack’s Main Street, cooked up burgers, pizza, chicken and ribs to local residents for 44 years and continues feeding locals to this day under new ownership.

Welcoming daughters Corrine in 1977 and Chelsey in 1986, the family was complete with three children. Today, youngest daughter, Chelsey, is managing five employees at the latest family partnership – the Kamsack Liquor Store.

In the 1980s, Olson was granted power of attorney for a Kamsack doctor with ailing health. Although somewhat outside his wheelhouse, Olson said during his time managing the medical office, his eyes were opened quickly to the precarious state of the provincial medical system. Olson took part in the hiring of locum doctors from South Africa and England who have since moved on to other communities.

Over the years, Olson has co-chaired the Main Street revitalization project, worked with the Kamsack Town Council, sat on numerous boards, served as president of the Kamsack and District Chamber of Commerce, was the major shareholder for the 1985/86 season for the SJHL Yorkton Terriers hockey team, and served as president of the Kamsack Economic Development Committee. He takes pride in his contribution to seeing Kamsack was granted one of the first SARCAN recycling depots in the province.

In the early 1990s, Olson participated in ushering in Kamsack’s first Co-operative Loans Association. The enterprise would serve as a local finance lender of low-risk loans between $5,000 and $25,000. The program ran successfully for many years until doors closed in 2017.

While juggling his own businesses and family, Olson continued to dream of ambitious initiatives that would bring jobs and economic prosperity to the broader region. He sat on the steering committee of an alfalfa pelleting plant west of Norquay, as well as the steering committee of a flax processing plant, which functioned as a thriving business located between Mikado and Canora, before it was destroyed by fire.

Olson has also explored visions of bringing cutting-edge industry to the area, including the development of an ethanol and feedlot complex, as well as a strawboard plant. Strawboard is essentially made from wheat straw and a form of polymer under a heat and press process to make a high quality furniture type board. When compared with commonly used MDF board, Olson describes it as superior in standing up to water exposure and screw nails.
“People are still asking me about the strawboard plant,” offered Olson. “We had excellent support of farmers from Pelly, Veregin, Togo and Kamsack. Oswald Henry of KPMG (a professional services network) raised money locally for a feasibility study, we had a legal team in place, and a manager on board. Unfortunately, at that level, politics can get in the way of progress. I still believe strawboard is an outstanding, durable product.”

During the Harper and Trudeau government days, with the support of letters from the town of Kamsack, and the R.M. of Cote, Olson pursued the building of a 500-unit federal prison in the Kamsack area. With the help of his local members of parliament, Olson sent letters to the ministers in charge of Correctional Services of Canada.

“Conservative representative, Steven Blaney, and Liberal representative, Ralph Gooddale, were both receptive of the development,” said Olson. “They replied by saying that the government was not looking at building a prison at the time. However, they said they would place Kamsack at the top of the list.”

Currently living with Gladys at their home in Madge Lake, Olson is happily “semi-retired” as he puts it. He helps his daughters at the liquor store when he is needed and enjoys seeing old customers and friends who pop in.


Olson whittles down his secret to success as his ability to take calculated risk.

“It always takes risk to start a business,” explained Olson. “Over the years, people have said things like, ‘He won’t last six months.’ I don’t listen to them. I do my own thing and I don’t worry about the competition. If you spend your time worrying, you won’t get anywhere.”

When asked if he had any regrets looking back on his rich and varied career, Olson replied with a frown, “I wish I could have been a music teacher.”