It has been quite long since Microsoft was a considered a ‘cool’ company by the world. Some instances in which they helped Apple IIs to run mainstream business apps with SoftCard and they strengthened the PC market by providing GUI with Windows 3.0. With time they lost their mojo and people started perceiving them as an vicious monopolistic company that develops Windows OS and Office suite. Microsoft was the reason behind demise of Netscape and they were also aggressive when it came to buying out competitors. Later on the justice department put a brake on them. Since then world looks at Microsoft with dubious eyes.
But things are taking different turn, after Satya Nadela joined as the new CEO. Under his leadership, Redmond based company seems on the way to become cool again. The angry Windows fanatics became happy after Windows 10 brought back the Start Menu which was removed in Windows 8. Microsoft embarked into the hardware market with much appreciated Surface Pro 3. They also have got a really interesting platform called Microsoft Hololens, which has been generating lot of buzz these days.
As a mobile device maker they are getting better with branding with the soon to be launched Surface Phone by getting rid of the unpopular Lumia phones. In the software business, Microsoft is slowly becoming developer friendly and started contributing to the open-source community (example: Computational Network Toolkit, the artificial intelligence platform). Apart from all this, Microsoft is collaborating with Cyanogen on its Android flavor. They are working in conjunction with iPad Pro to develop a version of Microsoft Office
In the long run every company strives to become cool and with coolness money comes running behind you.