Bill Gates says, "I thought I was one mistake away from death." — Microsoft's success and his billionaire status didn't really arrive until the late '90s

Shockingly, Bill Gates said he didn't view Microsoft as a success until the late 90s.

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.