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Michael Wekerle’s known as the Oracle of Bay Street – a straight-talking finance whiz who has made a mint in the corporate world (even if he looks more like a rock star).RACHEL IDZERDA/The Globe and Mail

Michael Wekerle's known as the Oracle of Bay Street – a straight-talking finance whiz who has made a mint in the corporate world (even if he looks more like a rock star). On Oct. 15, "Wek" will make his debut on the new season of CBC's Dragons' Den, bestowing his bootstrap-style business sense upon Canada's aspiring entrepreneurs. Here, he shares some of the secrets to his success, including why you don't have to be a wolf to win.

Good karma is good business

You don't have to be too tough or too hard is advice I got from [businessman and philanthropist] Seymour Schulich, and it's something I come back to a lot. There is this idea that the people who are the most successful are also the ones who are totally ruthless, but I don't think that's the case. The best deals are not the one where one party is extremely happy and the other side is devastated. Yes, you want to win, but it's okay to make concessions. Sometimes I pay a little bit more, but that buys me the benefit of getting to deal with the same people in the future. You never know where anyone is going to wind up and most people don't like to deal with a person who screwed them over in the past. I definitely believe in karma. When a guy is down, I see an opportunity to give him a break. It's the kind thing to do, but even aside from that, it can also be good for business. I have backed traders when they were down and out – I remember one guy in particular, he had had a bad year and people walked away. I threw him a bone and that gave him back his dignity. I got the money back, I had a friend for life and I ended up making my firm a lot of money.

Fitting in is overrated

I dress for success, but for me that doesn't mean wearing a suit every day. I love my Tom Ford jacket with jeans, my tails. I've never had that corporate look. When I started working at the foreign exchange, I was 18 and my hair was down to the middle of my back. I remember interviewing with one of my early bosses, Alec Miller. He was such a cool guy and he said to me, "Kid, you're hired. You have half an hour to get a haircut." In that case I followed his instructions, but I've always been a non-conforming guy. To be noticed, you have to be different. Even as a kid, I strived to be a bit different – people have to be aware of you before they can become aware of your capability. It's not just about what I wear. On the whole I have a way of operating that people sometimes think is a bit crazy: I throw things out there, I confuse people a little bit, but there's a method to my madness. I think by throwing people off, you can figure out who they are faster. Are they for real, or all they all hat, no cat?

Success is chess

When I was a kid, I would go down to this parkette near the Elgin Theatre in Toronto to play chess. You'd wait in line to play against these old guys with the clocks. I think we were only playing for 25 cents. I never won, but it was a very valuable experience because it taught me to think about success by thinking several steps ahead. It's never the first move that you make that is going to be the winner, but when you make that first move, you have to be thinking about what's next, and what's next after that. I can't tell you how many times that has come up in my career. I never procrastinate, but at the same time, if you're making a decision so quickly that you're not thinking about the possible outcomes and responses, then you're probably making a mistake.

A different kind of Dragon

I don't really have a filter – I shoot from the hip, so I think that will do me well in the Dragons' Den. These are some incredibly smart and successful people I'm working with, just total masters of their various areas of expertise. I guess one thing I have is that a lot of my experience aligns with these people who are coming onto the show. I'm not a guy who could work at a bank – I don't have the pedigree in terms of education, I don't have the blue-blood background. I was always that grindy kind of guy in the small- and mid-cap companies, which is the essential entrepreneurial spirit. That's what Dragons' Den is all about. I'm kind of a one-trick pony, but it's a good trick in this case.

Be the early bird (and the night owl)

Go five minutes early, stay five minutes late. That's a piece of advice I always give. It's not a once-in-a-while thing – it's every day. It's about being the kind of person who is there and ready to work. We used to have a saying: You never miss the opening bell. I started working in finance when I was 18 and I didn't come late until I owned my own firm in my 30s. I never missed on bell, even if that meant going to the office straight from being out all night. We'd go from the bar to the gym, play squash, have a shower and be in at work before the bell.

Make time to rock out

Even when you're so busy with work, it's important for a person to have a hobby – something that you do for yourself. I love music – it's a way to settle myself down and cut out the world around me. I carry a harmonica everywhere I go, and I'll take it out and play it if I have five minutes. [One-minute guitar and harmonica interlude.] Life is about balance.

This interview has been condensed and edited by Courtney Shea.

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