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When looking at the brand rivalry of Microsoft vs Apple, I go back in my personal history to the time I first met Bill Gates at a conference in 1978 called Wescon. It was a chance meeting, and I learned about the basic programming language interpreter that he had written for the Altair computer. A brief discussion that opened my mind. I was just a child of 13 at the time and my father had “snuck” me in to the conference. I had just started learning about computers with one of the first TRS-80 computers from Radio Shack, and I was absorbed by the scene. In this discussion, Gates talked about the computer one day becoming something that not only could run a business, but that could be used at home to control lights, thermostats, and even play games. I remember the car ride home- when I was raving about the possibilities, Dad asked if I was too lazy to get up and change the thermostat or turn off the lights my self – why would I need a computer for that? For him, the computer he had bought me was for word processing and probably some simple games – a step up from Pong.

In that moment I learned that Microsoft would one day focus on the ubiquity of computing, controlling things, processes, etc. Apple on the other hand was different. I had the opportunity in the late 70s and early 80s to work with the Apple II computer. The focus was clearly more on visual actions than programming. More games, fewer business utilities. As I entered the business world in the Graphics Communications industry, specifically digital printing, that difference was never more apparent. Up until very recently, if you spoke with a graphics designer, media person or Agency, and you weren’t on a Mac, you would be scoffed at. Meanwhile, when I had to outfit my national team of production printing analysts with laptops, and I insisted on Macs, the company IT infrastructure pushed back hard, always insisting on PCs. I won that battle but it speaks volumes to the paths that these two giants took in their messaging – Corporate vs Artistic, Right Brain vs Left Brain, Numbers vs Number of colors.

In the famous 1984 Olympic Hammer Throwing ad for Apple, we saw this dystopian, artistic yet cold call to action – breaking free of the rigid business thinking into new and great heights of individuality. Microsoft, however, focused on creating the best possible business productivity software which was not unique, but served as an important evolutionary point in the development of corporate communications and governance.

Now in the last 14 years, since the iPhone was released, we began to see convergence in messaging. Suddenly, business apps could be run on your smartphone, and cloud based software could eliminate the need for big corporate PCs at a desk,

So in this battle, who was he Dog, who was the Underdog. I submit each was both, depending on the industry and use case for each. Brand messaging played squarely to their bases, like political candidates. Apple embraced the artsy, graphics, design communities, Microsoft the corporate IT world. Interestingly though, they both attacked the schools. Both had significant brand presence, having both given away hundreds of millions of dollars of equipment and software to early education, in hopes of snaring brand loyalty at the most impressionable age. This battle continues to this day.

For our purposes, I will focus on Apple as the underdog in the corporate IT space.In order to perform better in this space Apple must convince the IT CIO world that Apple MacOS X is a more secure platform than Windows. In fact, most breaches of security happen due to Microsoft failures. This should be an easy case for Apple to prove out, but they will need to think differently. At the core, Mac OS X operating system is built on Unix, considered the most secure computing operating system ever. Developed by Bell Labs, until recently, it drove most industrial equipment because of its bulletproof nature and secure structure. Apple however, was so focused on creating a new experience on top of Unix, that they never took advantage of their natural benefit. So my 3 suggestions for Apple:

  1. A public Hack-a-Thon event where hackers of all types are invited to hack into a secure Mac based datacenter and a Windows based datacenter. Just the mere bravado will get attention
  2. Actively market to CIOs the concept of convergence from Windows to Mac in the datacenter, while allowing Microsoft operating systems to operate on Mac servers. Replacing the hardware without significant change to infrastructure. It’s only natural that the OS comes next
  3. Micro-influencer targeting – find those who are respected in the industry and work with them to change their mind – not by paid interaction but by genuinely responding to their belief in Microsoft superiority, and then documenting their transition to liking Apple products more. Earned Media is key here.

Why do Microsoft users prefer them as a brand? Simple, this goes back to the old IBM axiom that if you buy Big Blue, you’ll never be fired. In other words, andIBM mainframe (and later PC) purchase was always safe since it was a known quantity. Such is the case with the risk averse IT world. However, when flayed open for the world to see, IT professionals should see that my preference, Apple and the Mac hardware/OS platform, provides a historically longer track record of security and stability, while, yes, being the trendier and prettier of the two as well!