[Maarten88]

> No mention of smartphones or social media in The Road Ahead

The road ahead is from 1995 and is about the Internet ("Information Superhighway") which Microsoft almost missed, but got right just in time.

The Smartphone he saw coming earlier than almost anyone else, and Microsoft desperately tried to conquer that market. They initially failed because existing mobile phone companies (Nokia, Motorola, Ericsson) feared Microsoft too much and refused to partner. Then Microsoft had to enter the market with third tier player HTC, which had no distribution at all. Then they executed very poorly, trying to miniaturize Windows using a pen interface and killing the much better specialized numerical ui they had. Then they got surprised by the iPhone and touch screens, and took way too long to come up with a good implementation of that, with Windows Phone 7. And then finally with Windows 8, they redid everything again for no good reason, loosing any loyalty from customers they had left.

They missed smartphones, but not because Bill Gates did not foresee them.

[scarface74]

Microsoft was in the smart phone market with Windows Mobile (based on Windows CE) way before the iPhone was a thing and HTC was far from a third tier player. At one point, before the iPhone, HTC was one of the most successful smart phone makers in the world, manufacturing not only its own brand but also third party white label brands and was manufacturing 80% of all Windows Mobile/Pocket PC/Windows CE devices - including those sold and labeled by other vendors.

[slyall]

Which edition of "The Road Ahead" did you mean? From the Wikipedia article:

After the book was written, but before it hit bookstores, Gates recognized that the Internet was gaining critical mass, and on December 7, 1995 — just weeks after the release of the book — he redirected Microsoft to become an Internet-focused company; in retrospect he had "vastly underestimated how important and how quickly the internet would come to prominence".[3] Then he and coauthor Rinearson spent several months revising the book, making it 20,000 words longer and focused on the Internet.[citation needed] The revised edition was published in October 1996 as a trade paperback,[6] with the subtitle "Completely revised and up-to-date.".[3]