Here we have Part 5 of 5 in our Canadian Dragons series. It has been quite a journey through the lives of these amazing entrepreneurs. We hope you enjoyed it!

Wilson has had his share of mistakes on his way to becoming a successful investment banker for the energy industry. But he never repeated the same one twice. Probably one of his biggest mistakes was betting on a senior management position as an engineer for Alberta Oil.

“I ended up working for a big oil company, and my dream was to be in upper management in this big oil company. That dream got shattered one day when I took their management aptitude test. They came back and said, ‘You will be a good technical specialist, you will not be a good manager.’ And maybe they were right. But what took me a few years to learn, was that I would not be a good manager in a large, bureaucratic organization, whereas in a small, nimble, fleet-of-foot, relatively entrepreneurial organization, I just might flourish. My short attention span, and a willingness to work on 20 things at once, probably is a big part of the success of my various entrepreneurial adventures.”

True to Wilson’s nature, he took a disappointing situation and turned it into a positive. That aptitude test also showed that his personality was more suited for business rather than engineering. Undeterred, he returned to college and earned his MBA with a discipline in entrepreneurship. Shortly thereafter, he put to use his energy investment background and founded Wilson Machie and Co. Later, he and a group of investment bankers established FirstEnergy Capital Corp.

While he amassed his wealth by being in the right place at the right time during the Alberta oil boom, Wilson has stayed true to his roots and is always at the ready to help his hometown of Saskatoon, Canada. He remains a down-home kind of guy, someone who will gladly have a beer with you and just talk about what’s on your mind. He believes in investing in people and surrounding himself with experts to run the parts of the business they know best. “Maybe it’s because I come from the oil and gas industry where you need to drill 10 wells to get three great wells, two marginal wells and four or five dry holes. So if I invest in 10 businesses, I know right now that one or two of them are probably not going to make it. But I’m not smart enough to pick which one or two.”

Wilson, one of the venture capitalists for aspiring entrepreneurs who make the grade on Canada’s hit show Dragon’s Den, is not afraid to take risks. Nor does he hesitate to go out on a limb when a situation calls for it. “I am highly focused on the entrepreneur and what they know about their business. Honesty and integrity are a must. Passion is a given; they have to be passionate about the business they’re in. They also have to know what they know, but they also have to know what they don’t know. I love the answer ‘I don’t know but I’ll find out.’ That’s a good answer.”

His diagnosis of advanced stage prostate cancer in his 40s has certainly grounded him and given him a strong appreciation for life. Although Wilson retired in 2007 from FirstEnergy, the self-professed workaholic lives life to its fullest and is at the ready to help any aspiring entrepreneur or philanthropic cause. “The ratio of winners to losers has gone up over time. It’s gone up because I’ve gotten better at evaluating people – not smarter at evaluating businesses, but better at evaluating people. Most of the mistakes I’ve made have been in trusting people. Because every business is going to have speed bumps. It’s how you manage those speed bumps and turn the ship around that makes the difference. Absolutely there have been some mistakes, and some great people and some great businesses that haven’t worked out. That’s just the nature of business. But I’m not afraid.”

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Adam Toren