Forget Satya Nadella's Windows Phone fumble, Bill Gates' "greatest mistake of all time" cost Microsoft $400 billion

Microsoft's co-founder admitted that losing the mobile space to Android was his most costly mistake, with Windows still trailing.

Running a successful company like Microsoft for 50 years is no easy feat. As part of the challenges of operating a multi-trillion-dollar industry, several mistakes are made along the way.

For instance, Microsoft CEO Satya Nadella admitted that pulling the plug on Windows Phone at the height of its glory was a strategic mistake. While in an interview, the executive indicated that there were other plausible alternatives that the company could've embraced rather than culling the mobile division:

"The decision I think a lot of people talk about — and one of the most difficult decisions I made when I became CEO — was our exit of what I'll call the mobile phone as defined then. In retrospect, I think there could have been ways we could have made it work by perhaps reinventing the category of computing between PCs, tablets, and phones."

As Microsoft's 50th anniversary edges closer, I'm looking back at Microsoft co-founder Bill Gates' greatest mistake. In 2019, while speaking at an event with venture capital firm Village Global, the executive admitted that his greatest mistake during his tenure as Microsoft CEO was losing the mobile space to Android.

In every sense, Microsoft is arguably the best software development company, which is evident across its earnings reports. Building on this premise, the philanthropic billionaire claims developing an operating system similar to Android would've been "a natural thing for Microsoft to win."

However, Bill Gates indicated that Microsoft missed its opportunity with Android partly due to his mismanagement, coupled with anti-trust issues that capped the company's progression.

This gave Google the upper hand and competitive advantage over Microsoft, allowing it to acquire Android in 2005 and launch its first device in 2008. As you may know, Android is the most popular overall operating system in the world, predominantly because of its versatility and wide array of customization options.