Way back in April of 2014, I wrote a short cautionary column about some of the good and bad aspects of the cloud. Specifically, I noted that startups in particular needed to make certain that they didn't end up prematurely spreading their businesses a mile wide and an inch deep. The many charms and exciting enticements of the cloud make this frightfully easy to do. The cloud is cheap, relatively easy to navigate, and everywhere you wanted to be (just like VISA)-; all at once. That, of course, is both a blessing and a potential curse if you aren't careful about how you roll out your offerings. Trying to support and service from "here to eternity" isn't easy for anybody.

At that time, especially for new entrants, the main reason that the cloud was so easy and accessible was because there was really only one reasonable and cost-effective on-ramp. That was Amazon Web Services (AWS), which really created the cloud for us civilians who simply didn't care to learn about, or pay for, any more infrastructure than what was absolutely necessary to get our companies launched. AWS was an inexpensive, ubiquitous and utterly scalable ("buy" the byte--pun intended) solution that seemed to become the industry standard overnight. Google and Microsoft were basically nowhere, and IBM wasn't even in the game. Watson was playing chess while Amazon was cashing checks.

I sat in many tense meetings when the guys from Microsoft tried to give people amazing deals on Azure (which Microsoft eventually offered as a cloud alternative) and it was as if they were offering to give these people a bad case of acne. Microsoft was discovering that it couldn't even give the service away and, for my two cents, I didn't see any realistic prospect that things would get better.  Not because Azure was a bad service, but because the last thing growing startups can afford (regardless of the "learn as you go" myths) is on-the-job training. No one wants to pay for someone they're already paying to learn on their dime.  The brutal reality was that even if you were inclined to try Azure, you couldn't find and hire anyone who knew how to work with it, because everyone else you knew was using AWS. If you can't find the horses to hurdle the next hill, you stick with the herd and go with what's tried and true-- even if it's relatively new. In the mainframe era, guess who got rich from the saying, "Nobody ever got fired for choosing IBM."

So, for several years, I basically believed, once again, that Microsoft had missed the boat. ("Binged" anyone lately?) And frankly, when I continued to see that Microsoft still ranked among the most valuable companies in the world, its stock at all-time highs, I couldn't really understand or explain why. I had met Microsoft ceo Satya Nadella at 1871 and he was a terrific and committed technologist, but he wasn't a magician. There had to be more to the story.

Ultimately, whenever I was asked, I attributed Microsoft's persistent value largely to the inertia that kept Windows and Office entrenched for so many years. No one I know is getting any less lazy and sticking with what has worked for you in the past is too easy, even though it's not gonna get the job done going forward. Habits and installed bases are hard to break.

The better explanation is that I hadn't really focused on a much bigger boat and a far more material movement. I was so entrenched in our startups and small businesses that I missed how quickly the cloud was transforming the enterprise-level solutions.  The biggest global businesses can't get to the cloud fast enough. And frankly, this space is Microsoft's home court and increasingly one where, once again, it's Microsoft's business to win or lose. I like Microsoft's odds these days because I learned long ago that, if you want to beat Babe Ruth, you better be playing something other than baseball.

However, the real psychological driver-- the thing that even Amazon (and certainly GOOGLE as well) will have to eventually overcome-- isn't simply the reliance on the breadth and stability of Microsoft's technology, which by definition is almost never cutting-edge.  Microsoft's critical advantage is that in our new connected world, where we get into strangers' cars,  invite strangers to stay in our homes and buy things from strangers all over the world, nothing matters more than trust. And, lo and behold, the big boys trust Microsoft a lot more with their data and their security than they may ever trust the new tech kids on the block.

The trust issue is likely to make Azure a winner in the long run. If you're looking for someone to hold your hand while you're crossing the chasm, it's more than reassuring to be guided and supported by Microsoft, a company that's already there with its legacy customer base. Just as an example, Microsoft's Active Directory service has more than a 90% market share in the enterprise segment.

As hard as it is to believe, Microsoft--an ogre for decades-- has become the trusted OG and, most likely, the keeper of the cloud for the future.