As Microsoft's 50th anniversary edges closer, there's a lot of nostalgia in the air. Depending on how you look at a half-filled glass, there are plenty of amazing moments we've reveled in as longtime Microsoft watchers. There have been bitter moments, too. For instance, Microsoft CEO Satya Nadella admitted that killing Windows Phone was a strategic mistake.
Bill Gates, Microsoft co-founder, recounted the early days of founding and running the day-to-day company operations in a detailed, dated article by The New York Times from 1995 (via Fortune). Shockingly, the Microsoft co-founder revealed that he hadn't always been confident about his abilities.
In a separate report, Bill Gates admitted to CNBC that "I wouldn’t say that I felt comfortable that we were successful until about 1998 or so." For context, this was 11 years after Microsoft had gone public, raising over $61 million in a single day.
At the time, the software giant had enjoyed considerable success, brushing shoulders with major tech players like Apple. It's worth noting that Gates had already attained billionaire status despite his woes to propel Microsoft to a new realm of success.
According to Bill Gates:
“Not until the late-90s did I feel like, ‘Wow, we can even make a few mistakes and still be okay. I thought I was one mistake away from death until then. That was just my mentality.”
Fast-forward to 2025, Microsoft is arguably one of the most successful companies in the world. In 2024, Microsoft's big bet on AI and multi-billion partnership with OpenAI briefly propelled the software giant to the top spot, ahead of Apple and NVIDIA as the world's most valuable company with over $3 trillion in market capitalization.
Bill Gates' ruthless focus on work has contributed to Microsoft's current success. However, the co-founder's track record isn't blemish-free. The co-founder admits that the greatest mistake during his tenure fumbled Microsoft's opportunity "to be what Android is," translating to a $400 billion missed opportunity.
Bill Gates revealed his greatest mistake of all time made Microsoft miss its opportunity with Android, partly due to mismanagement and antitrust-related issues. However, Android co-founder Rich Miner says Bill Gates is more responsible than he's letting on.
Related: Bill Gates says he'd start Microsoft again as an AI-centric firm
It's been years since Bill Gates left Microsoft to focus on philanthropy. However, reports indicate that the co-founder is still intimately involved in company affairs and treats his advice as 'gospel.'
