Microsoft's 50th anniversary is approaching, prompting reflections on its history. CEO Satya Nadella admitted that discontinuing Windows Phone was a strategic misstep. Co-founder Bill Gates revealed in a 1995 retrospective that he did not feel confident in Microsoft's success until around 1998, eleven years after its public debut. Microsoft established itself alongside tech giants like Apple during its early years. By 2025, Microsoft became one of the most successful companies globally, significantly boosted by investments in artificial intelligence and a partnership with OpenAI, achieving a market capitalization of over a trillion dollars. Gates identified his greatest mistake as missing the opportunity to dominate the mobile market, resulting in a potential loss of 400 billion dollars due to mismanagement and antitrust challenges. Gates remains connected to Microsoft, providing insights despite stepping back from daily operations for philanthropy.