Ask Paul: July 28 (Premium)

Happy Friday from Mexico City! Here’s another lengthy installment of Ask Paul with some great reader questions to help kick off the weekend.
Ray Ozzie
sabertooth920 asks:

Please, speculate on what the modern Microsoft would look like had Ray Ozzie not left (and been given the authority)?  In hindsight, he looks a lot wiser and more prescient than we all gave him credit for, at the time.

Absolutely.

But we are experiencing Ray Ozzie’s Microsoft right now: it was Ozzie who led Microsoft’s push to the cloud---almost 20 years ago, by the way---in his role succeeding Bill Gates as Chief Software Architect. I told this story in the Software + Services chapter for Windows Everywhere.
Ray Ozzie led Microsoft’s push into cloud computing, appropriately enough, with a 5000-word Gatesian memo, “The Internet Services Disruption,” that would forever change the company.

“Computing and communications technologies have dramatically and progressively improved to enable the viability of a services-based model,” Ozzie writes in the memo to Microsoft’s executive staff and their direct reports. “The ubiquity of broadband and wireless networking has changed the nature of how people interact, and they’re increasingly drawn toward the simplicity of services and service-enabled software that ‘just works’. Businesses are increasingly considering what services-based economics of scale might do to help them reduce infrastructure costs or deploy solutions as-needed and on subscription basis.”

“Most challenging and promising to our business, though, is that a new business model has emerged in the form of advertising-supported services and software. This model has the potential to fundamentally impact how we and other developers build, deliver, and monetize innovations. No one yet knows what kind of software and in which markets this model will be embraced, and there is tremendous revenue potential in those where it ultimately is.”

Three years later, Microsoft was ready to show off the work that had happened in the wake of this memo. Key among that work, of course, was Windows Azure, previously codenamed Red Dog, a cloud-scale operating system built by a small team that included NT architect David Cutler.

The PR spin today is that Microsoft’s current success is due solely to the leadership of Satya Nadella. But Nadella simply continued the strategy started by his predecessor, Steve Ballmer, who ordered the company to implement Ozzie’s vision and pivot to cloud computing. This is, I think, one of the more successful business transitions in history, given how Windows-centric the firm was and how hard it is to move away from a successful model that makes money even when that model is starting to wear thin.
Oddly, Ozzie was only at Microsoft for five years: he joined in 2005 when Microsoft acquired his firm Groove Networks for the collaboration technology that still sits at the heart of SharePoint, OneDrive, and...