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“Head of the Pack” - Advantage Magazine Interview with Hillsdale’s CEO, Chris Guthrie

head of pack photo 

Head of the Pack 
Interview by Rachael Hudak 

By defining expectations and managing risk, Hillsdale Investment Management CEO, Chris Guthrie, is guiding his firm upward and onward. 

Chris Guthrie is not a man of small leaps. The ambitious entrepreneur went from washing dishes to serving as founding CEO of his own company, Hillsdale Investment Management Inc., and by providing a wide array of sophisticated investment strategies, he has taken the independent Canadian firm from the management of $1 million in assets to the management of $1 billion. Advantage recently spoke with Guthrie about his entrepreneurial philosophy and got the details on how he has grown his firm.

Advantage: When did you first become interested in management? 
Chris Guthrie: At 14 years old, I was running two paper routes and quickly learned how to delegate—in this case to my mom. She quit. My next job—at 17, as a dishwasher—taught me a lot about personal responsibility and the role of management to create the appropriate conditions for success.

How did that lead to founding your own company? 
After 10 years working as a consultant for top money managers across Canada, I had some experience and the naïve confidence that I could do better on my own. I didn’t have any money or assets or clients, but I had a dream and tremendous support from my wife. With help from family, friends, and an angel investor, I started Hillsdale Investment Management in 1996. Shortly after, I hired one partner and three hard-working staff and moved our operations downtown. Today, we have a staff of 30 and manage assets totalling $1 billion.

How is Hillsdale different from the investment companies it competes against? 
Our investment approach tends to be more cautious and calculated than most, emphasizing continuous testing and proof of concept before investing. We successfully manage both personal and institutional portfolios using a combination of proprietary quantitative investment tools and traditional fundamental company analysis. We also spend a great deal of time measuring the effect of luck on our portfolios, and I believe this gives us a better ability to clearly define expectations for clients and to meet or exceed them with greater frequency.

And what is your role in the company today? 
As an entrepreneur, I try to surround myself with good and intelligent people, which our clients appreciate. Internally, I help give meaning to my staff, define expectations, and encourage intelligent risks. I also spend a lot of time with our talented service team, helping them translate information from our research and portfolio management into meaningful information for our clients. Because every part of our team works together to support relationships, many of our clients have been with us since we started. I believe in the saying “If you want to go fast, go alone; if you want to go far, go with many.” At Hillsdale, we want to go far. We don’t need to go fast.

You may not be in a rush, but you’re definitely growing. 
I feel very lucky to be working with such a talented team. Our people, whether they have a background in investment management, mathematics, computer engineering, or marketing, are striving to be at the top of their profession. We all hold the same values of integrity, dedication, loyalty, and teamwork. We now have 200 clients, 10 products, and cover 25,000 global companies. And we’re constantly looking for ways to improve our people and our processes and focus on training and research.

What do you find to be the most challenging aspect of managing operations at Hillsdale? 
Investment management is all about dealing with uncertainty, insuring against unrecoverable losses, and managing risk. At Hillsdale, we think a lot about what we don’t know and how to best support our clients. To minimize the effects of uncertainty on the management of the firm is a constant challenge. If we do this well, I know we will stay ahead of the lion—and hopefully at the head of the pack.

How does your team maintain success? 
Education, experience, and the pursuit of excellence help us maintain credibility and reliability. As markets evolve, investment managers need to be adaptive and innovative, and Hillsdale is a learning organization. We focus on idea generation and are constantly adapting to changing markets. Moving forward, I want to encourage continued efficiency in our processes and growth for our employees.

We’ll continue to be active in improving the industry while keeping our company in top shape. Hillsdale’s success will be ultimately defined by our clients and the value we create. 


Chris Guthrie’s Career Milestones 
1980 – Works the night shift as a dishwasher
1984 – Receives a BA in political science from the University of Western Ontario
1993 – Receives his CFA Charter
1996 – Plans, finances, and incorporates Hillsdale Investment Management, with assets under management (AUM) totalling $1 million
2002 – AUM at Hillsdale totals $100 million
2012 – AUM at Hillsdale totals $1 billion