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The Oracle of Bay Street: finance bad boy Michael Wekerle is back, and his new firm is already the talk of Toronto

Michael Wekerle’s wild lifestyle got him kicked out of the firm he helped build. Now he’s back and running a merchant bank that promises to make a lot of people very rich

The Oracle of Bay Street: Michael Wekerle is back on Bay Street to make a lot of people very rich

Wekerle bought his 80-hectare Caledon compound from the retired senator Trevor Eyton

When a video game player loads NBA 2K13, say, or Madden NFL on his Xbox, he’s invited to join a social media platform where he can play online against other gamers for money and prizes. The platform, which was developed by the Toronto company Virgin Gaming, is poised to become the Facebook of the gaming world. But, until recently, chances were good that Virgin would go the way of many promising Canadian tech companies and get scooped up by foreign multinationals, decamp for the U.S. or simply die due to a lack of financing.

Luckily, Rob Segal, Virgin Gaming’s chairman and CEO, met Michael Wekerle, the wildly successful Bay Street trader turned merchant banker who is quickly becoming known as the man who could save the Canadian tech and media sectors. Segal first encountered Wekerle in 2009, when he was attempting to license the Virgin name from Richard Branson’s massive media and travel conglomerate. He needed to raise $7.5 million to do the deal, and a friend suggested he talk to Wekerle. Segal says Wekerle was the most unusual trader he’d ever met. “He’s like Mick Jagger meets Warren Buffett,” he says. “He heard the concept, understood it immediately and said, ‘I can do this, no problem.’”

Last year, Wekerle’s new firm, Difference Capital, invested another $20 million in Virgin Gaming—money that allowed the company to rebuild its technology and prepare for its next stage of growth. “It was a big bet,” Segal says. “We were trying to do something no one had really done before, and Difference had the stomach for it.”

Wekerle is known on Bay Street as a risk-taker—and not just when it comes to playing the markets. He’s one of a handful of business personalities who transcend the gleaming towers and become known for their extraordinary market sense, their ability to make themselves and others extremely rich, and their high-flying lifestyles. Wekerle, however, is in a class by himself—an eccentric outsider with raffish hair, at least a dozen tattoos (a Stones tongue and a peace sign among them) and a preternatural talent for making money.

Difference Capital has only been around for a year, but it’s already the talk of Bay Street. Wekerle has raised funds from such big-name backers as Ned Goodman, the veteran investment banker behind the billion-dollar Dundee Corporation; Frank Giustra, the legendary Vancouver mining magnate and founder of Lionsgate Entertainment; and Seymour Schulich, another billionaire veteran of the mining industry, famous for co-founding Franco-Nevada. Wekerle found other investors by canvassing his diverse network of friends and colleagues: Bill Holland, the chair of CI Financial; John Crow, the former Bank of Canada governor; and Mats Sundin, to name just a few.

Difference has already invested in 20 or so private and public tech and media companies, all of which Wekerle believes have valuable intellectual property, a proven revenue stream and serious growth potential. Bay Street has ignored the technology industry for so long that a niche investor like Difference is sure to be a flame for many moths, all seeking capital to expand their operations. Wekerle intends to build Difference into the biggest tech banker in the country.