Absurdly Driven looks at the world of business with a skeptical eye and a firmly rooted tongue in cheek. 

We all make mistakes.

Sometimes, they're really big ones. 

Or at least we think they are at the time. 

Perhaps, though, some years later, we realize that the supposed great mistake led us along a different path that held perhaps even greater joys.

Bill Gates, though, clearly hasn't got over his biggest mistake.

It seems to gnaw at him like a prickly seam on the inside of his dad-jeans.

Indeed, at a recent event presented by VC firm Village Global, Gates wanted to admit to his greatest faux-pas.

He was talking about how software -- and especially platforms -- was a winner-take-all business.

He explained how he believed software entrepreneurs need to make big sacrifices at the inception of their companies in order to achieve the big engineering win. (His comments begin around the 11:00 mark of the video.)

Then he made his confession: 

The greatest mistake ever is the... whatever mismanagement I engaged in that caused Microsoft not to be what Android is. That is Android is the standard phone platform -- non-Apple form -- phone platform. That was a natural thing for Microsoft to win.

Oh, he wasn't done with expressing his manifest searing pain.

He added: 

There's room for exactly one non-Apple operating system, and what's that worth? $400 billion that would be transferred from company G to company M.

You see? He couldn't even utter the word Google. That's how much it hurts him

Some might think it fanciful, however, that Microsoft would have been the natural creator of a non-Apple phone platform.

The company was obsessed with forcing its software down the sometimes reluctant throats of businesses.

What it was far less adept at was understanding what real human beings wanted, needed and, most importantly, felt.

It's all too easy looking back and realizing that there should have been a competing operating system.

Microsoft's mistake was that it thought far too much about monetary growth and not enough about human beings.

Steve Jobs was far more intuitive and caring about human existence. 

Yes, he wanted to win. But he wanted to win with style, acute design sense and emotional uplift.

When Google launched Android, it certainly wasn't a company with enormous people-feeling either. 

But it could at least see some of the basic elements that made Apple such a success. 

Google, though, didn't create Android. It bought it in 2005.

At the time, it was an operating system for digital cameras, not cellphones.

Moreover, once the idea to transpose Android to phones was made, the biggest element of its growth was that its basis was Linux.

This being open-source meant that Google could offer it to so many phone manufacturers around the world.

This was a complete contrast to Apple's entirely self-contained, self-controlled world.

Would Microsoft have been so generous of spirit?

I fear not. Microsoft would have tried to create a separate walled garden with a large toll.

Which may not have made it a fine competitor.

Microsoft really didn't grasp phones well at all. 

Who can possibly forget how Microsoft CEO Steve Ballmer reacted when Apple released its first iPhone?

He laughed at it. He considered it a preposterous proposition.

Please take a look.

The iPhone was apparently absurdly expensive and didn't appeal to business customers because it didn't have a keyboard.

Sometimes, a leader can keep looking through the same prism every time and not understand the fundamental, emotional joys of a competitor's world. 

In Microsoft's case, it wasn't emotionally geared either to grasp the true future of phones or the potential benefits of appearing to give something away for free to suit your aims.

Please don't beat yourself up too badly, Bill.

It wasn't mismanagement. It was merely a lack of vision.

You didn't do too badly, mind.

Published on: Jun 23, 2019
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.