I've always held the belief that even though Gates may have been an effective manager, he was a terrible person. IMHO, his repeated anti-competitive, deceptive, and often illegal behavior was the main reason for Microsoft's success.

He may have enabled scalability by being more hands off, but I'm still kind of surprised it took him that long to learn that software quality had fallen off that far. And I'm not even getting into the monopoly aspect of it. Maybe that was the business model all along, you can save costs by not adhering to quality standards as long as you land the right exclusivity deals with OEMs. Microsoft gonna Microsoft.

It was 2003, and Microsoft's next version of Windows, codenamed Longhorn, was not doing well. On top of that, Google and the rest of the internet natives were eating Microsoft's lunch, and many analysts expected the company to fade away, as IBM had done before.

Bill Gates, obviously, didn't want that to happen, and true to his nature, was looking for a technological solution. In many ways, Longhorn was fighting the last war: it invented a new graphical subsystem and a new storage system, at a time when modern apps were happily using HTML and SQL. Groove Networks had developed a peer-to-peer synchronization technology that blended online and offline so an app could have the best of both worlds. It was a true local-first architecture that was also internet native.

Gates arrived early in the morning with one or two assistants. In 2003 he was still the wealthiest person on the planet, but he carried himself like any normal engineer. One of my colleagues, who hadn't been told he was coming, only learned about it because they rode with him in the elevator. He introduced himself and made small talk. You can imagine their shock.

At the meeting, we presented our technology and our ideas for how we could fit into Microsoft's plans. Later I learned that this was a mini-product review, like Sinofsky talks about in the OP. I pitched him (somewhat half-baked) ideas about how Windows files folders could become collaborative, shared folders. He was very engaged, but thankfully polite--he didn't tell me it was "the stupidest thing he had ever heard." I suspect he was on his best behavior because he had already made up his mind to buy the company.

The highlight of the meeting, for me, was watching him and Ray (whom he'd known for a while) riff on everything around Windows, the internet, and technology in general. It was like improv, where every idea someone came up with was followed up with, "Yes, and then you can also...". You could tell Gates was engaged because he kept rocking in his chair, a classic tell we later learned.

Microsoft did ultimately buy Groove Networks, but not for the technology. I realized much later that Gates had bought Groove mostly to hire Ray. In 2006, Gates announced that he was retiring and appointing Ray Ozzie as Chief Software Architect.

At Microsoft, Ray spearheaded a project codenamed Red Dog, which the marketing folks later called "Azure". I'm convinced that Ray doesn't get enough credit for his contributions to turning Microsoft around.

Had Bill already planned all this when he visited us in 2003? Probably not, but seeing his mind work, it wouldn't surprise me if he had a little bit of an inkling. You never know.

https://www.nytimes.com/1990/03/20/business/business-people-...

But less than two years later

https://www.nytimes.com/1992/02/04/business/microsoft-presid...