I’ve been using Microsoft products since I was a kid, something the company is hoping I’ll remember fondly alongside the Pogs, Super Soakers, and Tamagotchi in its recent Internet Explorer ad above.

“You grew up. And so did we,” concludes the narrator. And though nostalgia may seem an odd marketing choice for a software company, it makes sense for Microsoft. The tech giant is betting that people my age – I’ll be 28 soon – can come around to a brand they’ve known forever but never loved. While it likely won’t do much to help the infamous Internet Explorer, such a strategy just might work for the company overall. Like mustaches, neon, and bow ties, sometimes it takes a trip to the depths of uncoolness for something to become cool again.

Internet Explorer: ‘Horrific’ and ‘Outdated’

I polled my colleagues (nearly all of whom are in their 20’s) about their browser usage and asked what word they’d most associate with IE. Not one uses it; unsurprisingly, Chrome took the cake, with Safari getting a couple of mentions. But more than that, IE was described as ‘outdated’, ‘horrific’, and a ‘nuisance’, and I’m leaving out some of the really harsh stuff. There’s no getting around it: people hate Internet Explorer.

While a few 90’s references won’t convert anyone to IE, it occurred to me while watching the ad that for Microsoft in general such a gambit might actually pay off. If my incredibly unscientific polling of coworkers and Twitter followers is to be believed, Microsoft isn’t loved by 20-somethings but it isn’t hated either.

Bill Gates: Rich philanthropist obsessed with saving the world. I think he used to do something with computers?

Microsoft is ‘Old’

Here’s how Microsoft was described by those I heard from: “old”, “old school”, “antiquated”, “outdated”. But it wasn’t all bad. I also heard “reliable”, “solid”, “business”, and “work.” Most of us are used to relying on Microsoft in our jobs; we don’t love it, but it mostly works.

So what the company needs to overcome as a brand is the idea that its history makes it outdated. And that’s exactly what the IE ad tries to do. Nostalgia is a clever way of turning this issue on its head. It reminds us the past was kind of fun, after all, and oh by the way we’re doing new stuff too. The company, which is ten years my senior, may as well be saying, “We’re only old if you are.”

Most telling, though, was what I didn’t hear from anyone about Microsoft or IE.

Ugly Christmas sweaters: so uncool they became cool again. Just sayin’.

Microsoft as Underdog?

I was most curious as to whether any of my peers would describe Microsoft as “big” or some variation thereof. No one used any such term, much less the dreaded “monopoly.” You see, I grew up both using Microsoft and hating it. I was taught that Microsoft was big and evil, and that Bill Gates was a monopolist. But I was six years old when the Department of Justice first started looking into Microsoft on anti-trust grounds, and in high school when the case was settled. Today, I think of Bill Gates first and foremost as a philanthropist.

By and large, people my age don’t associate Microsoft with this kind of negativity; we don’t think the company is particularly cool, but that’s as far as it goes. And that’s an opportunity.

Today, Steve Jobs is dead, the iPhone is being touted as a rich person status symbol (super uncool), and we’re all sick of our Mac friends’ insistence that you can’t be creative without the help of Apple. In mobile, the big war is between Apple and Google and – wait for it – Microsoft is an underdog.

Is it so unfathomable that you’ll one day feel about your Windows phone what Apple fans feel about the iPhone? That you would feel good about choosing Microsoft to stand out from the crowd? It’d take a whole lot of innovation and no small dose of marketing, but it’s not impossible.

Ten years ago, the idea that allegiance to Microsoft could be a way of being different would have been insane. Today, it’s just crazy enough to work. The children of the 90’s might not be firing up IE, but over time a similar campaign might work for the company behind it. After all, we’re only as old as we feel.