As Microsoft’s 50th anniversary approaches, a wave of nostalgia sweeps through the tech landscape, inviting reflections on the company’s storied past. For those who have closely followed Microsoft over the years, the journey has been marked by both triumphs and trials. A notable admission from CEO Satya Nadella highlights one of the more contentious moments: the decision to discontinue Windows Phone, which he now regards as a strategic misstep.
Reflections from the Founding Days
In a revealing retrospective published by The New York Times in 1995, co-founder Bill Gates shared insights into the early days of Microsoft. His candidness about his own insecurities is striking; he confessed that he did not feel truly confident in the company’s success until around 1998. This was a full eleven years after Microsoft had made its public debut, raising over million in a single day—a remarkable feat at the time.
During those formative years, Microsoft was already establishing itself alongside tech titans like Apple. Gates, despite his burgeoning billionaire status, felt an immense pressure to drive the company forward. He reflected, “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.”
A New Era of Success
Fast-forward to 2025, and Microsoft stands as one of the most successful companies globally. The previous year marked a significant turning point, as the company’s substantial investment in artificial intelligence and its multi-billion partnership with OpenAI catapulted it to the forefront of the tech industry. At one point, Microsoft surpassed both Apple and NVIDIA, achieving a staggering market capitalization of over trillion.
Gates’ relentless dedication to work has undeniably shaped Microsoft’s trajectory. However, he is not without his regrets. In a candid moment, he identified his greatest blunder: missing the opportunity to dominate the mobile market, which ultimately translated into a staggering 0 billion lost potential. This miscalculation stemmed from a combination of mismanagement and antitrust challenges. Interestingly, Android co-founder Rich Miner suggests that Gates may bear more responsibility for this oversight than he acknowledges.
Related: Gates has expressed a willingness to start Microsoft anew, this time with a focus on artificial intelligence. Despite having stepped back from day-to-day operations to devote time to philanthropy, reports indicate that he remains closely connected to the company, offering insights that are still regarded as ‘gospel’ within Microsoft’s corridors.
