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Peter Jessiman: ‘There’s just great idea-share and mindshare' in the family office space

After Peter Jessiman and his sister, Heather, sold Bison Transport—founded by their father, Duncan, in Winnipeg in 1969—they faced a crucial decision: how best to manage their newly monetized equity? 

In the end, they decided to start Jessiman Family Investments Inc., a single-family office. But not before doing extensive research. In the process, they realized how important networking and community can be in the sometimes insular-seeming world of family offices.

That realization is a driving force behind Jessiman's presence at this year’s annual Canadian Venture Capital and Private Equity Association (CVCA) conference to be held in May. Jessiman's firm will be hosting an invitation-only reception (presented in partnership with Canadian Family Offices) exclusively for family office executives and family principals. The goal is to “foster meaningful conversation and community among family offices across Canada.”

Jessiman and his CIO, Brendon Corbett, recently spoke with Canadian Family Offices about the founding of their office, its investment approach and why networking among family offices is so important.

It was our most popular article of the week.   

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Member Content

Highlights from this April’s Canso Market Observer

Does anyone know what the plan is?

Canso's April Market Observer started with an undeniable truth: irrespective of what is or was written about it, whatever happened in the first quarter of 2025 will bear no relevance to what’s happening now. 

Two days into the second quarter, the Trump administration announced “reciprocal tariffs” on April 2, dubbed “Liberation Day,” and unleashed an unprecedented assault on the global trading system. The Canso team writes: “It reminds us of the 3rd quarter of 1987, when the October 19th Black Monday stock market crash of 22.6% happened just over 2 weeks later. It also is reminiscent of the 3rd quarter of 2008 when 3 weeks later in October the credit markets had ceased to function. Portfolio managers still visited their clients but what they were telling them about ‘performance’ bore no relation to what had happened to their portfolios only a few weeks later.”

This story is brought to you by Canso Investment Counsel Ltd.

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