After Peter Jessiman and his sister, Heather, sold Bison Transport—founded by their father, Duncan, in Winnipeg in 1969, it had grown to become the largest privately owned transportation and logistics business in Canada—they faced a crucial decision: how best to manage their newly monetized equity. In the end, they decided to start Jessiman Family Investments Inc. (JFII), a single-family office based in Winnipeg, but not before doing extensive research. That included consulting with other single-family offices and wealthy families for advice and direction. Their willingness to help surprised him, Mr. Jessiman says, and it impressed upon him how important networking and community can be in the sometimes insular-seeming world of family offices.
That realization is a driving force behind the Jessiman family office’s presence at this year’s annual Canadian Venture Capital and Private Equity Association (CVCA) conference, Invest Canada ’25, in Calgary. On May 27, JFII will be hosting an invitation-only reception (presented in partnership with Canadian Family Offices) exclusively for family office executives and family principals. The goal: to “foster meaningful conversation and community among family offices across Canada.”
Mr. Jessiman, who is CEO of JFII, along with Brendon Corbett, JFII’s chief investment officer, recently spoke with Canadian Family Offices about the founding of their office, its investment approach, today’s turbulent market conditions, and why networking among family offices is so important.
Can you walk us through the founding of JFII?
Peter Jessiman: JFII was born out of the sale of our longtime family business, Bison Transport. We sold at the very end of 2020 to the Richardson family. It was a great transaction all the way around, and the company continues to thrive under their leadership. The Richardsons are wonderful to do business with, and I’ve always held them in the highest esteem. We were very proud that we were able to keep the company headquartered in Winnipeg.
It’s one of the things that owners of businesses often don’t pay enough attention to when they’re thinking about exiting: Who are they going to sell to and will they feel good about it afterwards?
Jessiman: We had been approached many times over the years about a potential sale, merger, or to go public. We were never interested and really believed in our team to continue growing the firm successfully. But then, when we finally came to the conclusion that it might be the right time to consider selling, the Richardsons were right there waiting in the wings. They just love the business and the industry, and it was a perfect fit.
So how did you decide to set up the family office?
Jessiman: The biggest decision a lot of owners or founders would ever have to make is, are you going to go it alone and do a single-family office, or are you going to turn to a multifamily office and partner up with others? We decided we had a substantial enough asset base that it would warrant at least considering a single-family office. We did a bit of work researching that idea and networking, talking to some other families about their decisions, and in in the end we opted to start an SFO.
I had a couple of very key hires to make, namely the CIO and CFO. We spent a lot of time searching, in Winnipeg and right across the country. We got extremely lucky with those two hires, and then we added some great talent to support them in accounting, finance and analysis. I’m really proud to have our daughter Cady working with us in an analyst role.
Were there any particular challenges you faced?
Jessiman: I’d say it went pretty smoothly. We took the same approach we took at Bison: It’s all about people. If you get the right people, you can make great things happen. So, it was really just a matter of whether we could find the right people and convince them to make the move. It’s not an easy thing to do, but we thought we had a good story to tell and a bright future. The rest of the stuff, you know, it just takes time. You have to put proper systems and technology in place. You’ve got to get process and people aligned. But we had done that before, and we’re pretty good at it.
As your family office becomes more established, how important is networking with other families, like you will be doing at your reception at CVCA’s Invest Canada ’25 next month?
Jessiman: I have been really impressed with the fact that a lot of very successful families across Canada and the U.S. are very willing to talk and share ideas and strategies. There’s just great idea-share and mindshare in this space. I would have thought all these families would just keep their secrets to themselves, but it’s been the exact opposite. Brendon is on the phone all day, every day, with different families and offices in Canada and the U.S., and I’ve just been amazed at the great ideas and suggestions we’ve been able to get through those channels.
Brendon Corbett: There’s the adage that if you’ve seen one family office, you’ve seen one family office. No two family offices are the same. But I think having the opportunity to get together with others in this space is important. We’re four years into our journey, and so we’re in our infancy still, compared to other family offices that have been around for decades. To the extent that we can, we spend time with other family offices talking about things like governance, Next Gen education, how they go about investing, and even things like cybersecurity and how they’re managing their footprint online. Everyone is happy to share what they’ve learned, but also what hasn’t worked.
Bringing the family groups together has always been part of how we’ve approached the space. We’ve observed over the past couple of years that a bunch of family offices attend the CVCA event. So, we thought that if we’re all in the same town for the same event, it would make sense to put together a bit of a gathering. We’re excited about it.
What is your investing focus at JFII?
Jessiman: We’re in a combination of public equities, private equity and real estate. We kept all our real estate after the sale, and so we’re sitting on a large national portfolio of industrial real estate, including almost 700 acres at CentrePort here in Winnipeg. Part of our focus is public equities, which we manage externally through a select group of advisors. We didn’t want to bring in a whole new team of equity and fixed income analysts. Our internal focus is really on the private equity piece.
Corbett: On the alternatives side, we invest in private credit and private equity funds as an LP. We’ll also co-invest in deals alongside our private equity fund partners, and then we also do direct investments. For us, when it comes to private equity funds, we’re looking for managers with a demonstrated track record of strong performance. That usually puts us in the universe where the managers are raising their third or fourth funds as opposed to first- or second-time funds. We haven’t been active in the venture or early-stage growth space to date.
You also invest directly in businesses?
Jessiman: We have, yes. Our first direct investment was in wealth manager Wellington-Altus, and that could not be going any better. Our most recent deal was a co-investment with SeaFort Capital, which is the McCain and Sobey families from Eastern Canada, in customs broker GHY International. So, we’re doing direct investments either by ourselves or through co-invests.
That side of it should come as no surprise to anybody. We came out of the private company universe where we owned 100 per cent of our business. The only thing different now is that we’re a minority shareholder in a number of different businesses, so we’re adequately diversified.
When you’re looking at investment opportunities, what is your focus?
Jessiman: We spent a lot of time establishing our investment policy statement, and the biggest part of it, in my mind, is not what are you going to do, but what are you not going to do. Brendon mentioned that we don’t do early-stage or angel, and that’s not because we don’t like it. There are firms really set up to do that, who have a whole ecosystem and really understand the risk model. We just don’t have that, so we stay in our own lane and stay focused.
That might sound almost paranoid, but it’s a matter of figuring out what you’re best at. So, we’re not directly investing in AI, big data, machine learning or leading-edge medical technology. We get exposure in those areas through LP positions in funds, whose managers Brendon and his team spend a lot of time finding and vetting.
With our direct investments, we’re looking to diversify in the coming years. We like logistics and distribution. We come from a hard-asset-based private company, so we’re used to kicking tires. We’re used to owning real estate. Those are all spaces we’re very comfortable with and feel that we have good analytical capabilities. We also love technology-driven business services with strong recurring revenue models. Our investment in a financial services firm was a bit of a different thing for us, but Wellington-Altus just has unbelievable momentum. It has proven to be a phenomenal investment, and we’re proud of the work the team is doing there.
How has private equity been affected by the market turmoil going on right now?
Jessiman: Whether it’s public or private equity, markets are sideways at best. It’s the uncertainty that’s impacting everybody. The thing that businesses hate more than anything is uncertainty. Everyone is just tired of the ever-changing, manic nature of what’s happening in the markets right now, and you can extrapolate that to include all these tariffs and the whole relationship between Canada and the U.S. and the ‘51st state’ nonsense.
Truth is, we can work with any policy. We may not like it, but we can plan around it if we know what it is. We can put a strategy in place and say, ‘OK, this isn’t necessarily how we would like it or how we would design it, but it is what it is. The policy’s in place. Now let’s go figure out how to work with that.’
The problem is when the policy changes every day, that’s when you get whiplash. That uncertainty is really causing chaos in both public and private markets. Transaction volumes are way down. When you get this kind of uncertainty, the first thing people do is grab their chequebook and sit on it. We look at this the same way anybody managing their personal finances at home would; they’re cutting spending. They’re just saying, ‘I’m going to wait until I figure out what the hell is going on here.’
And nobody knows. I’m convinced that not only does nobody in the investment industry know—I don’t think anybody in the U.S. government knows. I don’t even think Trump’s cabinet knows. It’s such a bizarre and unprecedented time. You just have to learn to work in the chaos for the time being.
Corbett: In an environment like this, it becomes challenging to invest in people or in capital expenditure projects, or if you’re a private equity fund, it becomes hard to invest in businesses. This is where patience and discipline are extremely important. In times of uncertainty and heightened volatility, you have to feel confident in the managers you’ve entrusted capital to, knowing that they’re going to act as responsible stewards. All the work that we do in due diligence ends up being incredibly important.
Jessiman: You have to remember your mandate and your strategy. The overwhelming majority of family offices make investments for the very long term. What happens in our public equity portfolio in the next six weeks or six months makes absolutely no difference to us whatsoever. Obviously, if we could choose, we’d prefer markets to go up, but they don’t always go up. So, stay focused on the long term and be very selective.
To learn more about the JFII family office event at the Invest Canada ’25 conference, please contact shetherington@cvca.ca.
Responses have been edited for clarity and length.
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