Liquidating Nvidia shakes the market—this is the second time Masayoshi Son has done this.

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Tuesday’s earnings report shows that SoftBank founder Masayoshi Son has once again made a headline-grabbing all-in gamble. The billionaire, famous for his extreme investment style, has completely sold off SoftBank’s $5.8 billion stake in Nvidia, redirecting funds toward the AI sector—including plans to invest $30 billion in OpenAI and taking part in a $1 trillion AI manufacturing center project in Arizona.

SoftBank sold all 32.1 million shares of Nvidia at an exit price of about $181.58 per share, only 14% lower than Nvidia’s all-time high of $212.19. Although analysts emphasized that this move should not be seen as a negative stance on Nvidia, but rather as reflecting SoftBank’s need to raise funds for its AI strategy, Nvidia’s stock still fell nearly 3% after the news broke.

Notably, this is SoftBank’s second complete exit from Nvidia, with the previous one being extremely costly. In 2019, SoftBank sold $4 billion worth of Nvidia shares for $3.6 billion, shares that are now worth over $150 billion. Although this time the timing is better, the decision to fully liquidate still raises market questions: Did Masayoshi Son spot risks that others missed?

The 68-year-old Masayoshi Son’s career is full of extreme bets. From losing $70 billion of personal wealth during the dot-com bubble, to the legendary success of investing in Alibaba, and to the painful failure of WeWork, his investment approach has always been all or nothing. Now, the market can only look for clues from his track record, and this uncertainty is all investors have to go on.

A Continuation of Extreme Investment Style

For Masayoshi Son, compromise is never an option. During the late 1990s Internet bubble, Son’s net worth reached about $78 billion in February 2000, briefly making him the richest person in the world. But the subsequent bubble burst caused him to lose $70 billion—which was the largest personal financial loss in history at the time—and SoftBank’s market value plummeted 98% from $180 billion to just $2.5 billion.

In that disaster, Son made his most legendary bet: a $20 million investment in Alibaba in 2000, reportedly after only a six-minute meeting with Jack Ma. By 2020, this investment had grown to $150 billion, making Son one of the most respected figures in venture capital and giving him funds to stage a comeback.

Alibaba’s success often overshadows Son’s tendency to stay at the gaming table too long. In 2017, when Son needed capital to launch the first Vision Fund, he didn’t hesitate to seek $45 billion from Saudi Arabia’s Public Investment Fund—long before it became mainstream for Silicon Valley to accept Saudi money.

After journalist Jamal Khashoggi’s murder in October 2018, Son condemned the killing as “shocking and deeply regrettable” but insisted SoftBank could not “turn its back on the Saudi people,” maintaining his commitment to managing Saudi capital. In fact, the Vision Fund actually sped up deal-making soon after.

The Painful Lesson of WeWork

That round of betting did not turn out well. The large investment in Uber generated years of book losses, and then came WeWork.

Ignoring opposition from subordinates, Son gave the shared workspace company a staggering valuation of $47 billion in early 2019 after multiple rounds of investment. But WeWork’s IPO plan collapsed after the release of its infamously problematic S-1 filing.

Even after ousting Neumann and implementing a series of cost-cutting measures, the company never truly recovered—ultimately resulting in SoftBank losing $11.5 billion on its equity stake and another $2.2 billion in debt. Son reportedly later called it “the stain of my life.”

Market Lessons from a Second Sell-Off

Tuesday will certainly become a major turning point in Son’s comeback story. SoftBank disclosed it had sold all its Nvidia shares—not to diversify, but to double down elsewhere. Although the exit price was near the peak, it marks the second time SoftBank has completely exited from Nvidia, and the first time came at a terrible cost.

This move also shook the market. Although analysts stressed that the sale shouldn’t be seen as cautious or negative towards Nvidia, Wall Street can’t help but wonder: Has Son spotted something others haven’t? Based on his investment track record, maybe he has—and this ambiguity is all investors have to go on right now.

Masayoshi Son has long sought another comeback. His career proves that when the 68-year-old investor doesn’t push his chips to the center of the table, it’s even more surprising.

Risk Warning and DisclaimerThe market carries risks, and investments require caution. This article does not constitute personal investment advice and does not take into account the particular investment goals, financial situation, or needs of individual users. Users should consider whether any opinions, views, or conclusions in this article fit their specific circumstances. Investing based on this article is at your own risk. ```