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

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.

Was Microsoft's Android fumble Bill Gates' fault?

More recently, Bill Gates was placed under fire by Android co-founder Rich Miner for whining about Microsoft losing mobile to Android. Miner indicated that he helped develop Android to prevent Microsoft from "stifling innovation" by controlling the phone like they did with PC.

For context, Miner was among the development crew that helped Orange launch the first Windows Mobile phone in 2002. According to Miner:

"So, sorry, Bill, you're more responsible for losing the $400B than you realize."

Bill Gates admits that were it not for his mismanagement, Microsoft would've seized the opportunity with Android and become the company.

According to the Microsoft co-founder:

"You know, in the software world, in particular for platforms, these are winner-take-all markets. So, you know, the greatest mistake ever is the whatever mismanagement I engaged in that caused Microsoft not to be what Android is, [meaning] Android is the standard non-Apple phone form platform. It really is a winner-take-all. If you’re there with half as many apps or 90% as many apps, you’re on your way to complete doom. There’s room for exactly one non-Apple operating system, and what’s that worth? $400 billion that would be transferred from company G [Google] to company M [Microsoft]."

To that end, Android stacks miles ahead of Windows with 45.53% of the market share compared to the latter's mere 25.36% (via StatCounter). It'll be interesting to see if Microsoft is able to catch up with Android, especially as Windows 10's end-of-support edges closer and a wave of backlash against Windows 11 grows stronger.