Core Viewpoint - The article discusses the investment journey of Masayoshi Son, highlighting his significant financial losses and gains, and his unique approach to investment that combines risk-taking with a keen eye for opportunity in technology and innovation [3][4][45]. Group 1: Investment Philosophy - Son's investment strategy is characterized by a willingness to take substantial risks, often leading to significant losses, but also to remarkable gains when successful [4][30]. - The article contrasts Son's approach with that of Warren Buffett, emphasizing that Son is not afraid to invest in innovative technologies, while Buffett prefers more traditional investments [43][45]. Group 2: Key Milestones in Son's Career - Son's career is marked by several pivotal moments, including his early investments in Yahoo and Alibaba, which yielded substantial returns, and his later struggles with WeWork and other ventures [9][23][25]. - The article notes that Son's ability to capitalize on emerging trends, such as the rise of the internet and artificial intelligence, has been a defining feature of his investment success [9][33]. Group 3: Current Challenges and Future Outlook - Despite past successes, Son faces challenges in the current investment landscape, particularly in the AI sector, where he has been criticized for not securing significant stakes in leading companies [34][41]. - The article suggests that Son's future in investment may hinge on his ability to navigate the evolving technology landscape and leverage his past experiences to identify new opportunities [39][46].