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All in the family

Photo by Doug Little

Jessimans Open Up Investment Office

When the Jessiman family sold Bison Transport to James Richardson & Sons in 2021, they looked around the table and asked one very important question, “now what?”

After owning the Winnipeg-based trucking firm for 51 years, the Jessimans felt they had taken it as far as they could and the company’s impressive growth could only continue if it was in the hands of a larger enterprise.

So, after more than a half-century in private business, they decided to stick with what they knew. They opened Jessiman Family Investments Inc., a family office with a mandate to invest in private companies across North America.

“Individuals or families that had success owning private companies tend to want to keep their focus in the private space,” says Peter Jessiman, CEO of JFI. “We feel we can understand and influence events much more in a private business than in a large public entity.”

Family offices are a relatively new concept in Canada but they’re growing in popularity with the generational wealth transfer that’s occurring as many older entrepreneurs sell their businesses. 

The sale price of Bison wasn’t released but Jessiman says it was a “substantial sum” for JFI to work with.

“It was a billion-dollar business and highly profitable,” he says.

One of the first orders of business was building a team. In addition to his sister, Heather Jessiman, who is JFI’s managing partner, Susan Deleau, formerly of Great-West Lifeco, was brought on as chief financial officer and Brendon Corbett joined as chief investment officer, coming over from People Corp. His daughter Cady also joined the firm as a business development associate. The office headquarters is a 4,500-square-foot space on Lorimer Boulevard in south Winnipeg.

JFI made its first investment in November 2021 with a $45-million infusion into Wellington-Altus Financial, a Winnipeg-based financial services firm. It followed that up with a $10-million investment in a private equity business in Halifax called SeaFort Capital.

“We’re going to invest in incredible management teams with great vision. We’re largely agnostic about industry and even geography, so it’s really about the company’s leadership team and our belief in their ability to execute on a large scale,” he says.

Jessiman says JFI does not have a typical private equity mindset because it’s not there to squeeze out efficiencies from its investments and move on as quickly as possible.

“We owned our business for 51 years. We take a long-term view of things. If we had to generate returns according to a specific timetable, we could be forced to do things that might not be in anybody’s best interest. If you’re going to build something worthwhile, it’s going to take time,” he says.

On the philanthropic side, the Jessiman Foundation has been very busy with numerous six and seven-figure gifts to organizations such as the Alzheimer Society of Manitoba, DASCH and Assiniboine Park Conservancy.

“Philanthropy is what gets all of us the most excited these days,” he says. “It’s not that good a story if you have success and then take all your marbles and go buy expensive toys. It’s a lot better story if you give a lot of the money back to those that really need it.”

Jessiman’s family, including his wife Dana and daughters Cady and Alex, parents Duncan and Judy, sister Heather and her three children, Thomas, Edward and Isla, and JFI’s Deleau, all play a very active role with the foundation’s philanthropic endeavours.

Jessiman says there’s no question that even though JFI has a mandate to invest throughout North America, its braintrust will remain here.

“We love Winnipeg, we always have and we always will,” he says.

Jessiman Family Investments Inc.


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