By Trefis Team
Publication Date: 2026-11-12 09:21:00
Part 3 of our Microsoft and AI series. Start with part 1: How Microsoft Missed $2 Trillion In AI.
Remember the Windows Phone? Or using Bing on purpose? Microsoft spent the 2000s missing the things that changed how we live: search went to Google, the phone in your pocket went to Apple. In 2015 it wrote off $7.5 billion of its Nokia phone business. Bing still has about 4.8% of the world’s searches.
The stock told the story. It peaked in December 1999 and didn’t close above that level again until October 2016, almost 17 years later. From the end of 2002 to early 2014, it returned about 91% with dividends, roughly 6% a year.
And that was buying after the crash: a buyer at the 1999 peak was still down about 17%, with dividends, when Satya Nadella took over as CEO. That is the real risk of paying a peak price for a great company. For families with a few million dollars in a handful of tech leaders, the question isn’t whether those stocks recover, but whether their plan can wait….
