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Ian Cumming was a Windows guy. After almost 40 years in the IT industry, he knew everything there was to know about Microsoft's operating system. He started out as a computer programmer on IBM mainframes and then graduated to personal computers that ran MS-DOS.

He'd been a Windows user ever since Microsoft had introduced its graphical user interface OS in 1983. As head of sales and marketing for an IT security company, Cumming had experienced all the good things about Windows: the business applications like Microsoft Office and cheaper prices thanks to all the vendors that sell Windows-compatible hardware—to name just two. He'd also experienced all that was bad about it, including unexpected crashes and that notorious susceptibility to viruses—also to name just two. But if you were in business, Windows was what you needed.

At least, that's what Cumming thought, until a friend persuaded him—"with a great deal of resistance"—to buy an Apple PowerBook G4 for home. He'd flirted with Apple back in the 1980s, while working for a design company. "I found Macs to be a bit of a weird world at that point," he says. Back then, the computers weren't compatible with Windows-based machines. But times have changed. When Cumming started playing around with his new Mac, he found the notebook "much more intuitive" to use—and far more stable than Windows. Plus, he had no problems with viruses. He also discovered how easy it was to transfer data from his Mac to his PC and vice versa. "Compatibility is no longer an issue," says Cumming.

When Cumming decided to set up his own company, selling organic fertilizer to commercial farmers, he decided to use Apple—much to the horror of many of his Windows-touting business associates. "I didn't have to think about it for long," he says.

Intelegacy Corp. has a wireless network that can accommodate 30 computers in its headquarters in Pickering, Ontario, and has employees in Denver, Florida and Australia. By the end of 2008, Cumming estimates he'll employ 200 people, including staff at a pair of plants in Prince Edward Island (one to manufacture liquid and granular fertilizer, the other for desalinization). All of Intelegacy's computer users will work on Macs, even though they need to communicate with a myriad of businesses and government agencies, almost all of which run Windows-based computers.

For Cumming, the single biggest breakthrough for Apple was working out those compatibility issues. These days, he and his staff work on Microsoft Office:mac, a Mac version of the popular suite of applications that works seamlessly with the original Windows version. When it comes to data compatibility, "over all, we've done a good job at hitting the big stones," says Willi Powell, Apple Canada's strategic development manager. Although Apple competes with Microsoft at the OS level, the two companies have co-operated on office applications. "There are some files you absolutely need, like word processing, and we've worked closely with Microsoft to make sure Word is as good as it can be," says Powell. "We'd like to hold Microsoft up as a beacon to other software developers for the platform."

Historically, larger institutions have shied away from Apple in favour of a standardized platform. But Apple computers have found acceptance at educational institutions, and they're considered the premier machines for print production, graphic arts and video editing. Still, many applications made for Windows-based PCs still aren't available for the Mac. For instance, Adobe's recently launched Premiere Elements video-editing software runs solely on Windows. Mac users can only watch the finished product if they have one of Apple's new-generation dual-boot Macs, which run on Intel processors. These Macs allow users to run graphic design, photo- and video-editing applications on Mac OS X and run dedicated Windows-based applications on the Windows OS.

A funny thing happened on the way to dual-boot, however: Software developers started making more business applications for the Mac OS X that were compatible with their Windows counterparts. In other words, data saved on applications running on the Mac OS could be opened in the equivalent Windows application, and vice versa. Compatibility between programs made for both operating systems is so complete that Cumming doesn't even operate his Mac in Windows mode. "That was our biggest nut to crack, to get through the Intel transition," says Powell. "None of the predictions of our demise were true, and we grew our businesses in a difficult time for PCs."

The porting of Macs to the Intel microprocessor and the inclusion of dual-boot mode began to pay off late in 2006, says Eddie Chan, a research analyst with IDC Canada. In the third quarter of 2005, Apple had a 5.8-per-cent share of the Canadian commercial desktop computer market; in the third quarter of 2006, it had 6.4 per cent. It's seen similar growth in the U.S. market. "Apple has been significantly outperforming the North American commercial computer market in terms of year-over-year growth," says Chan. In the third quarter of 2006, sales of Apple's commercial desktops were up 16.6 per cent in the U.S. Meanwhile, year-over-year sales in the desktop computer market were down 2.3 per cent over all. Same story in Canada: 17.4 per cent growth for Apple Canada in the third quarter of '06, compared with just 6.7 per cent for the Canadian PC market.

Among consumers, iMacs and MacBooks are also growing in popularity. Put this down to the halo effect of Apple's wildly popular iPod, says Chan. Smitten with the company's mini music marvel, more consumers have started to check out Macs. The move to Intel microprocessors has been instrumental in opening up non-traditional markets for Apple's computers. And though larger companies are also warming up to Macs, they're far more cautious when it comes to adopting new technologies than the average consumer.

And consumers are Apple's primary focus—the company doesn't aggressively market Macs to the enterprise sector. That, combined with the conservative nature of most IT departments, means Apple's share of the commercial computer market isn't nearly as strong as HP's or Dell's, says Michelle Warren, an IT industry analyst with Partner Research Corp. But she says sales of Macs are increasing in the consumer and, surprisingly, the small- and mid-sized business markets: "This year has definite potential for tremendous growth for Apple."

Price-sensitive SMBs have been more open to exploring Apple computers—even though they sell at a premium—because there's a trade-off that comes with Macs, says Warren: The total cost of ownership and security concerns diminish. Both Mac OS X and Windows XP have security and stability vulnerabilities, but Mac OS X is considered a far more secure and stable system. For many SMBs, owning a Windows-based PC costs twice as much as owning the relatively new Macs that run on the Intel processor, says Winn Schwartau, president of Interpac, a security awareness company based in Seminole, Fla. "The burdened cost of ownership per PC, just for support, ranged from $1,300 to $4,000 per year," he wrote in February, 2006, in his "On Security" column in Network World. Macs, on the other hand, "are close to immune to the endless train wrecks caused by viruses and worms."

By moving to Apple, Cumming felt he was getting a more stable platform that was less susceptible to virus attacks, which meant less downtime and fewer IT staff required to support the platform. Cumming claims his made-in-Canada organic fertilizer will eliminate the farmer's dependency on chemicals and lower the cost of fertilizer by 70 per cent, and he believes his Macs will eliminate his dependency on Windows and dramatically lower his company's total cost of computer ownership.

Microsoft is clearly spooked by the Cummings of the world. In January, it launched Vista, a spruced-up operating system that has been widely described as a Mac OS rip-off in terms of look and feel. What Microsoft is really pushing is Vista's improved security, though it's too soon to tell how well these new measures will protect users. For Cumming's part, he isn't "the least bit curious" about Vista now that he's switched to Macs. Yes, Microsoft has probably produced a more secure, more stable operating system, but he says it will still be more susceptible to virus attacks and is a more complex operating system—and therefore less stable—because it had to be backward-compatible with so many aspects of earlier Microsoft operating systems.

So will Vista help hold back the Apple juggernaut? Actually, Warren says, "it might ironically give people pause to think Apple," as Windows becomes more Mac-like in look and feel, and the two increasingly compatible operating systems make it easier for people to share programs. (Apple doesn't plan to rest on its OS laurels—it will introduce its latest operating upgrade, OS X Leopard, some time this spring.)

Computer reseller Derek Keoughan, president of Finnegan Software Inc., based in Brampton, Ontario, takes Warren's comments one step further: "These days, a Mac is an end-point—as is a PC—on a computer network. The computer is irrelevant, since most of the data files run equally well on both platforms, and even on a third platform such as Linux." Although Keoughan sells Windows-based PCs, the majority of his support calls aren't from people with PC problems; they're from people looking to troubleshoot network servers, cabling, routers, switches, firewalls and other network issues outside the realm of the workstation, be it PC or Mac. "It's not so much about the desktop any more as it is about the network," says Keoughan. "Ever try to get a lot done on a day when your Internet connection or network is down? The endpoints themselves are increasingly useless, regardless of how fancy, fast or configurable they are, if they're unable to communicate with each other."

Cumming agrees. When customers, vendors or suppliers come to his office with Windows-based notebooks, they can connect to his wireless network and share data files with his Macs. And when his database is up and running on an Apple server, he'll be able to share information with both Mac and Windows users via the Web.

There's another, more basic, issue at work here: Debates over price, compatibility and operating systems aside, no one can deny the iMac is the sexiest looking personal computer on the market, and that in itself has captured the attention of a younger audience, says Warren. And those young consumers will grow up to become the next generation of business owners and executives—a sure sign that Apple computers will be much more widely accepted in the business market a few years down the road.

Of course, as Cumming's conversion from Windows to Mac proves, you don't have to be a next-generation business owner to become an evangelist for Mac.

Vista on your Mac? Not so fast
Now that Apple computers use Intel processors—a change the company made last year—Mac owners can run Windows and Apple's Mac OS X side by side. That's thanks to a technology called "virtualization," which allows users to switch from one operating system to the other without having to reboot their computer.

So does that means Mac users will be able to run Microsoft Vista and have two state-of-the-art operating systems on one machine? Not so fast.

Using virtualization software such as Parallels or VMWare, Mac users can theoretically have Vista and OS X running side by side. But they can't use the cheaper version of Vista designed for home users — at least, not if they want to abide by the terms of the End User Licence Agreement, which software owners effectively agree to when they install a product.

That's because the Microsoft agreement states that anyone running Parallels can't use the $199 basic or the $239 premium edition of Vista. Instead, they have to buy the $299 business version or the $399 ultimate version of the long-anticipated OS. MIcrosoft says the move was necessary because of security issues with virtualization technology. A security analyst showed last year that, in theory, the kind of virtualization that Intel and AMD processors allow could be used to run malicious software programs alongside another operating system, creating the potential for damage.

AMD and Intel have both questioned whether the research is valid, however, and said there are no inherent security issues with virtualization. But Microsoft maintains that there's a chance such a problem could occur, and has therefore restricted the use of Vista to versions that it assumes are likely to be run either by corporations or by sophisticated users.

Unfortunately for anyone who plans to use their copy of Vista to play music or watch videos while running a virtual PC on their Mac, the Vista end user agreement also prohibits virtualization programs from playing any content that's encrypted with Microsoft's digital-rights management software—another security risk, according to Microsoft.

If you're a Mac user, you can get around these restrictions by using Apple's Boot Camp software, which also allows you to run Windows Vista and OS X on the same machine. But it's not virtualization software—which means that you'll have to reboot your computer in order to switch from one OS to another. —Mathew Ingram