Most investors would have heard of Warren Buffet but probably not many would have heard of Masayoshi Son, aka the Japanese Warren Buffet. He is a Japanese entrepreneur and the founder, chairman, and CEO of SoftBank Group, one of the world’s most influential technology investment firms. Few investors embody the extremes of visionary ambition and costly risk-taking quite like Masayoshi Son. He has built a reputation for making audacious bets on the companies of tomorrow, sometimes with astonishing success, and sometimes with equally spectacular failure.
Central to Son’s strategy in recent years is the Vision Fund, a nearly $100 billion war chest launched in 2017 and backed by sovereign wealth funds, tech giants, and banks. Conceived as the world’s largest technology investment fund, it set out to identify and dominate the “AI revolution” and the next generation of category-defining companies. For retail investors, the Vision Fund’s audacious track record offers valuable lessons, not just in spotting transformative trends, but also in understanding the risks of excess capital, concentration, and unbridled optimism.
The best and most famous bet by him is undoubtedly the $20 million investment in Ali Baba in 2000. He began divesting Ali Baba in 2020 and booked a profit of approximately 1.26 trillion yen (about $8.5 billion USD) from divesting its Alibaba stake, which amounted to roughly 425 times its original investment. Although it’s an impressive trade, the key takeaway is how he made the decision to invest. He had frequently described his investment process as an "instinct," an "animal smell," where he senses the "gut instinct of an underdog entrepreneur." This method was also applied to his Alibaba investment. He was a strong believer in his ability to see the future and bet on the most ambitious entrepreneurs and this self-belief, amplified by his past successes made him overconfident and become a core driver of the fund’s strategy. I found it quite incredulous that someone managing billions of dollars could base their investment thesis on gut instinct and his past wins could probably be due to just sheer luck. Everyone looks like a genius when the tides are up, you only see who is swimming naked when the tide comes down.
His subsequent investment picks based on his gut instincts didn't go as planned. But the most infamous case was probably WeWork. It was pretty incredible that he invested $4.4 billion into WeWork after just a 12-minute meeting with CEO Adam Neumann. The investment in WeWork has been nothing short of disastrous with total losses estimated to be around $14.3 billion to $14.4 billion. Key Lesson 1: You need to have a viable investment strategy rather than just relying on “instinct” in order to be a successful investor. Stay humble, don't get overly elated over a sudden investment windfall and keep your ego in check because your “stroke of genius” could be down to just dumb luck.
Masayoshi was also convinced about the potential of AI and its impact on society way before all the AI hype materialized and he even made an investment of around $700 million in Nvidia in 2018. Strangely enough, he had conviction and an investment thesis this time round, but he still divested all his Nvidia holdings in 2019 for about $3.3 billion, locking in a 4.7x return. The main reason for the sale was to show a return as the Vision Fund faced pressure and to secure investment for Vision Fund 2. We all know now this was a disastrous decision as if he held Nvidia till today, his stake would be worth around $150-$160 billion. It was a very painful lesson for him, and he even stated Nvidia was "the fish that got away." Key Lesson 2: The power of compounding is a powerful wealth builder so try your absolute best not to trap yourself in a situation where you would be forced to sell your stocks, especially the ones you have the strongest conviction.
In the end, Masayoshi Son’s story is not just a cautionary tale, it’s a mirror held up to every investor’s ambition. His journey reminds us of that vision without discipline can be a double-edged sword, and that instinct, while occasionally brilliant, is no substitute for rigorous strategy and patience. The line between genius and gambler is often drawn in hindsight, and Son has danced on both sides of it. For retail investors, the lesson is clear: conviction must be earned, not assumed; and the true test of wisdom is not in spotting the next big thing, but in knowing when to hold on, when to let go, and when to simply wait. After all, in investing, as in life, the biggest wins often come to those who resist the urge to chase and instead choose to compound.
