There’s been a whole lot written about why Verizon bought Yahoo this week, with most observers netting out that Verizon is trying to be a successful number three to Facebook and Google.But one thing we haven’t seen discussed much is the elephant in the room: Yahoo may have a lot of ad tech and email users and popular destination portals, but it’s an unhip, aging business that’s been steadily hemorrhaging users and unless Verizon figures out a way to fix that, it’s never going to be of much use to them. They’re facing the same problem with AOL, which, while it’s brought much ad tech to the  party, hasn’t contributed much in terms of hipness or audience. That’s all especially relevant these days too, as Go90, Verizon’s answer to YouTube and Sling, has pretty much been a bust, despite Verizon’s heroic efforts to make it happen.Go90 suffers from several problems. The biggest one is that it’s all short form content of the sort that can mostly be found on YouTube. And while Verizon has partnered with Awesomeness and other providers, the audience has yet to follow. That’s likely due to problem number two: because Go90 is a Verizon product, it’s main appeal is to Verizon customers who can watch without eating into their data plans. It’s also up against the legacy of years worth of prior telco content efforts, almost all of which, to put it bluntly, sucked, and it’s hard to get users to give them a second look.It’s unfortunate, because Go90 seemed like such a good idea when it was introduced: a mobile-first product that would combine a mix of long-, mid-, and short-from content from the networks and YouTube’s top creators. Only something got lost along the way and now it feels more like YouTube Lite without a real reason for being, and if you’re a 13 year-old YouTube fanatic, an app so tragically uncool is about the last place you're going to look for something to watch.Cool is a thing. Maybe it shouldn’t be, maybe we should be past it, but we’re not. We live in The Age of Cool. The absence of it dogs everyone from Hillary Clinton to the CW and it’s a huge problem for Verizon now that they’ve picked up Yahoo and AOL. Cool is not in Verizon’s DNA. They’re a great company with generally stellar service—they are one of the few MVPDs consumers don’t generally find to be evil—but they are just not cool. That means they don’t know how to make other companies cool. Which is going to be a real problem for them.Having all that ad tech is great and AOL is making some wise investments in programmatic television, but all those billions (around nine of them) that Verizon spent on Yahoo and AOL will be for nought if they can’t staunch the bleeding away of users and eyeballs.It’s not an impossible task. New branding for the conjoined company. An investment in the sort of big name talent and content that will bring people to the site. (Yahoo tried with Katie Couric, but the 50 year-olds who like Couric are not early adopters.) They have it somewhat easy in that they don’t need to convince users to switch away from YouTube; rather, they just need them to add AOLHOO to their mix. It is by no means an easy task—making a brand relevant again, even a rebranded brand, is one of the hardest things to pull off—but unless they do something major, their shiny new investments are going to slowly deflate like a balloon at a three year old’s birthday party.And as we all know, in both cases, that just leads to tears.