Steve Ballmer was an underrated CEO

The specific technologies that were successful is irrelevant. Microsoft has and continues to invest in nearly every computer related technology that may come around the corner or they got late on.

The problem with Microsoft was everything went through Windows. The entire company was designed to promote Windows.

This was the fundamental flaw with Microsoft that Nadella changed. He quickly not just made Windows just another part of Microsoft’s business, to a great extent he actively devalued it.

The fact that Ballmer invested in Azure, etc before Nadella would all be irrelevant because under Ballmer Azure would have remained a red headed step child to Windows, so it’s unlikely to have seen much success under him anyways. Same goes for pretty much everything else Microsoft is doing right now.

I was at Microsoft for the last couple years of Ballmer and the first few years of Nadella. He definitely did change the company and I remember at the time feeling that he handled the change really well, but from where I sat he spent the first part of his tenure evolving Ballmer's final push to move focus from Windows to developers. Everything Microsoft did prior to LLMs was to bring developers over, from VS Code to GitHub to WSL.

Now the company seems fully baked I to LLMs with everything they do chasing that. It would even make sense if the developer push was driven in part by the need to build up training sets for the eventual LLM work, though I really have a hard time believing that Microsoft was so well ahead of the game that they started grooming developers to provide data more than a decade ago.

Them along absolutely everyone else. ChatGPT was an iPhone moment.