Over a decade ago, I had the chance to interact with at a startup with a Microsoft senior person who joined the firm as CTO. One piece of advice he gave stuck out:
"Heroism doesn't scale"
This wisdom of it was instructive (and you can see it in Estridge's early struggles with success), but so too was the sense that perhaps this "wisdom" was part of what underlay Microsoft's malaise of the late 2000s against Apple and Google (and IBM's in this story and your final comment.)
Microsoft has plenty of similar stories, perhaps most famously the story of how Xbox was developed.
I was lucky to be at MSFT during what might have been the last gasps of when a single person could have a huge impact, and it was something I saw from time to time, but it by the 00s and surely the 2010s, it was in huge decline vs the stories that were told about the 1990s.
Edit: Someone posted below about how Windows 3.0 was also a misfit project.
There is also F#, which has had a huge impact on C#.
The entire async framework in .NET was originally developed by a small team headed up by one brilliant engineer.
Silverlight started as a project by a small team in Microsoft Research to see if they could shrink .NET's runtime down to be small enough to complete with Flash.
"Heroism doesn't scale"
This wisdom of it was instructive (and you can see it in Estridge's early struggles with success), but so too was the sense that perhaps this "wisdom" was part of what underlay Microsoft's malaise of the late 2000s against Apple and Google (and IBM's in this story and your final comment.)