A week before Wekfest, we meet at his office in Toronto. Wekerle is impeccably dressed in a pinstriped suit and dapper tie, his aviator sunglasses still in hand. His sandy hair is slicked back, but unfurls into a wavy mane over the course of the day. This is actually our second meeting. At the first, an irrepressible Wekerle held forth on a mixture of management strategy (“Empowerment and accountability go hand in hand, but if you don’t lead by example, you can’t win”) and general life philosophy (“Empathy is the best word in life”), until a friend called and Wekerle put him on speakerphone. Somehow that conversation led to a debate over whether Wekerle was once kicked off the stage at a private rock concert for trying to make out with the drummer. “I did not make out with the drummer!” Wekerle shouted. “I might have given him a kiss, but it was friendly, man.” This is what it’s like to sit across from Wekerle: He talks faster than you can listen, careens into random topics, cracks jokes and imparts wisdom, all in a single breath. It can be a challenge to keep up.

Today, though, he seems more subdued. He had been out the night before with staff drinking “shitty, sweet beer” at an Irish pub. When an assistant comes into the room, he orders us two large iced lattes and sips liberally from his when it arrives. We don’t get to talk for long before he’s interrupted to sign a cheque related to his Florida real estate venture (he’s got that on the go, too, partnering with Bill Holland from CI Financial to invest around $60 million), and then he has to take a phone call in another room. Shortly afterward, a friend arrives to give him a gift—a bottle of Dom Pérignon—and a freshly laundered shirt. The friend ended up wearing a wine stain one night, and Wekerle literally gave him the shirt off his back. When a co-worker named Mark Arbour needs him in a meeting, I ask to tag along.

Arbour is actually the director of operations at the Waterloo Innovation Network (WIN), yet another Wekerle venture. Earlier this year, Wek personally bought an office building in Waterloo that once belonged to BlackBerry, with a plan to build a centre of excellence for tech companies, a place to house startups and form partnerships with corporations around the world. In July, Difference put $2 million in a fund associated with WIN that will invest in local tech companies. In the meeting room, Arbour is already sitting with a banker who’s there to discuss financing for the building’s renovations and expansion. Wekerle darts off again, leaving Arbour and the banker to gape in confusion. “Does Mike want you in on this meeting?” Arbour asks slowly.

Podcast: How One Company Won Over the Dragons

Wekerle returns with our iced lattes and starts walking the banker through the plans for Waterloo. He lays out the terms of the financing he’d like, reeling off numbers, percentages and expected returns with his eyes closed, one knee bouncing up and down. The banker opens his mouth to interject when Wekerle’s BlackBerry rings. He picks up. From the sounds of it, the caller is pitching him on an investment opportunity. As the call drags on—Wekerle even spells out “difference” in his e-mail address—Arbour turns to the banker to break the silence. “You know, Wek took RIM public,” he says.

“I know,” the banker replies.

Finally, Wekerle hangs up. “Some of these prospects, man, I don’t know,” he says. “But I don’t want to be an asshole, so I was quite nice.” And then he’s dictating numbers again.

One of the many impressive things about Wekerle (or maybe one of his most frustrating traits) is his ability to do three or four things at the same time. He thrives on constant stimulation. In fact, he seems to function best that way. People who work with him have come to expect that his time and attention is limited. In a way, it’s the ideal personality for a trader.

Loading comments, please wait.