A nothing-to-lose attitude gave Sheep Dog the opportunity to play with one of the biggest names in the business world

Shawn Wilkie had to fly through the clouds before he could sell them. The 28-year-old scuba enthusiast and skydiver who, at last count, has visited 45 countries—many of them while staying with strangers he met on Couchsurfing.org—enjoys taking risks. One of his biggest happened about a year ago when the Antigonish, N.S.-based entrepreneur bought a plane ticket to San Francisco, hoping to convince Google to let him sell its new Enterprise Applications package for business.

“I felt like I was gambling,” says Wilkie. “I felt like I was going to the casino. There was nothing for sure, besides getting to actually meet some Google people.”

Based on a cloud-computing model, the Enterprise Applications allows companies to shift emphasis from static stand-alone applications to shared environments accessed via the Internet anytime, anywhere. “Since I’ve been using PCs, this is literally the biggest thing I’ve ever seen,” says Wilkie. “People talk about the old dumb terminals—the green screens. They were nothing more than a monitor and a keyboard. And that’s what’s happening with cloud computing, but on a much more secure and intense level.

“All of your information—your photos, email, music, videos, and applications—is being taken off your computer and put up on the Internet, managed by data-security experts. They have 17 copies of your data in multiple places around the world. So unless a nuclear bomb goes off and destroys the entire world, your data is safe and can be accessed at any time.”

Seven years ago Wilkie was a recent St. Francis Xavier University business grad working in the IT industry in Fort McMurray, Alta. (he calls it “Fort McMoney”), when he moved back to Antigonish to start his own company, Studentcomputers.ca. Now boasting nine full-time employees, the company sells Macs and other computer products at a student discount. It also provides technology solutions for small and medium-size organizations.

Lately Wilkie has been spending more and more time in Halifax, where his new company, Sheep Dog Inc.—as in “information’s best friend”—is located. “I kind of miss Antigonish,” he says. “I’m part of the community down there; I’m a volunteer firefighter. I think the saddest thing in this new venture is that I’m not going to get to fight fires any more. I like the adrenaline rush. And there’s a comparison to business there as well—the highs and the lows. I love it.”

In a sense, Sheep Dog was born out of Wilkie’s work in Antigonish, where he was dealing with customers having problems with email spam and viruses. The best solution he could find was Google’s free Gmail service. Then he started hearing about the company’s apps for small business. “It was a new product segment that didn’t exist before,” says Wilkie. “I started trying to get hold of Google but it was impossible.”

Eventually he signed up and paid for the product, then called the support number with this message: “I know that this is the wrong number. I know this is not the typical request. But I want to partner with you guys. I’ve been using Gmail since it came out. I’ve been deploying it for my customers. I’m very excited about the product.”

That could have been the end of it but Wilkie kept hounding Google. “I had the phone number now and kept calling back and calling back,” he says. “Finally someone called me back from their enterprise division and said, ‘We know that you’ve been aggressive with calling. We’re interested in chatting with you. Can we set up an appointment?’ ”

Wilkie has been back to San Francisco several times since that first trip a year ago, and Sheep Dog is now the only authorized Google apps reseller in Canada, and one of about only 30 worldwide. The company, which has a dozen people working in a tight noisy space in Halifax’s Bayers Lake Industrial Park, has closely aligned itself with Google. “We’re an extension of their reach, so we work with them very collaboratively,” says Wilkie. “It’s a really interesting situation. They’ve been absolutely phenomenal to work with.”

Wilkie says that on a single day recently Sheep Dog did $25,000 in sales; he hopes to be doing $500,000 a quarter by the end of the year. The company, which has clients in the Northwest Territories, California, Chicago, and China, recently signed a deal with a university in London, England. Wilkie can control clients’ computers remotely from pretty much anywhere in the world. “I just spent a month in Honduras on the beach with my computer, working,” he says. “I have voice and video chat. I can be in my office even if I’m not in the office. I have a 1-800 VOIP phone number that rings on my computer. Nobody knows where I am half the time.”

In an industry that is evolving as quickly as new ideas are hatched, is Wilkie worried someone else will come up with a better product? “Not at all; it’s Google,” he says. “It’s efficient, it’s quick, it always works, it’s never broken. For instance, there are 45 million Gmail users right now, and if anyone gets a spam message, they click on Report Spam. That message goes back through Google’s computer network and blocks that same spam message for every other Gmail user and Google apps user worldwide. You’ve got 45 million humans fighting spam on a second-by-second basis. Nobody else can compete with that.”

The aggressive gamble Wilkie made a year ago appears to be paying off big time. “Yeah,” he says. “When I doubled down, I did all right.”