About a decade or so ago, Wall Street labeled SoftBank’s Masayoshi Son (孫正義) as the new Warren Buffett. Why? Because of SoftBank’s huge bet on Alibaba in 2000 and 2004, investing US$80 million in total. Between 2016 to 2024, SoftBank sold its Alibaba holdings for nearly $80 billion (1,000x gain!), making it the most lucrative venture capital deal in history.

What’s Masayoshi’s biggest regret? SoftBank was once NVIDIA’s biggest shareholder, owning nearly 5% of the company. However, SoftBank liquidated its holdings in early 2019 for about $3.9 billion for a gain of $3.3 billion. Great investment.

Fast forward that to now. Those shares would be worth over $230 billion today! 😅