According to Outlaw Consulting’s brand report, some brands, like Converse’s Chuck Taylor shoes, are cool because they’re grounded in the past. Others, like Apple and Nike are cool for the opposite reason: they embody change and constantly reach towards the future. But there is a third category of cool brands, those that appeal to Millennials’ inner nerd. Pop culture has celebrated the nerd/geek culture for many years (Napoleon Dynamite, Jimmy Neutron, Sand Lot). Millennials are not afraid to admit to a dorky side and they admire brands that can do the same. According to Outlaw, Trader Joe’s, Jet Blue and In N Out Burger have won the love of Millennial trendsetters simply by being their quirky selves, doing things they own way and never apologizing: “(Trader Joe’s employees) wear these tacky Hawaiian shirts and publish that ridiculous newsletter. But it’s their own style. And it’s so much more inviting than the normal rigid grocery store.”

Given Millennials’ soft spot for the nerdy, it shouldn’t be a surprise that Microsoft is enlisting the ultimate nerd’s nerd, Bill Gates, to turn around its battered image. Bill Gates appealing? Well, for starters check out the adorable video, “Bill’s Last Day“, from January’s CES. Self-deprecating sense of humor was clearly on display (along with some pretty cool cameos by Millennial darlings Al Gore, Barack Obama, Jon Stewart, George Clooney, and more).

According to today’s Wall Street Journal, Microsoft is now launching a new $300 million campaign (that’s big) that will feature Gates and Jerry Seinfeld. The campaign theme is said to be “Windows, not Walls”, stressing the need to break down the barrier that prevent people and ideas from connecting. Now there’s an idea designed to win Millennials’ hearts! The campaign is said to break Sept 4. We’ll be watching to see if Mic Guy can compete with the charms of Mac Guy among Gen-Y.