The world's most formidable gambler is not one who never loses, but one who, even after losing hundreds of billions of dollars, still dares to push his chips to the center of the table.
At age 42 in 1999, he decided to invest in Alibaba after just a six-minute meeting with Jack Ma. Starting with an initial $20 million investment, his stake ballooned to over $200 billion at Alibaba's peak valuation in 2020, delivering staggering returns that became the envy of the investment world.
In 2016, at age 59, a 45-minute conversation with Saudi Crown Prince Mohammed bin Salman secured a $45 billion commitment from the Saudi Public Investment Fund for the SoftBank Vision Fund. He later calculated the rate of that deal: "One billion dollars per minute."
He possesses an uncanny foresight. In October 2017, speaking at the Future Investment Initiative in Riyadh, he declared that the primary investment focus of the SoftBank Vision Fund was Artificial Intelligence. At a time when many considered AI a distant fantasy, his prediction proved accurate five years later when the AI wave surged globally.
Now 67 in 2024, an age when many consider retirement, he was seen publicly leaning on Jensen Huang's shoulder, reportedly emotional over a monumental missed opportunity. In 2019, SoftBank Group Corp sold its entire stake in Nvidia, realizing a $3 billion profit. Had he held on, that stake would be worth over $200 billion today.
He has been the world's richest person for three days and alternates with Uniqlo founder Tadashi Yanai as Japan's wealthiest individual. He is Masayoshi Son, founder and CEO of SoftBank Group Corp.
Despite his immense wealth, why has this Korean-Japanese billionaire recently borrowed a massive sum from banks?
**A $40 Billion Unsecured Loan**
In March 2026, SoftBank Group Corp signed a 12-month, $40 billion unsecured bridge loan agreement with a consortium of banks. This marks the largest external debt issuance in SoftBank's 45-year history and is one of the most substantial loans seen in global capital markets in the past decade.
The lenders are no ordinary institutions: JPMorgan Chase, Goldman Sachs, Mizuho, Sumitomo Mitsui, and Mitsubishi UFJ.
What is the purpose of this colossal loan? The answer is to double down on the hottest company in the most explosive sector: OpenAI, the creator of ChatGPT. $30 billion of the $40 billion is earmarked specifically for SoftBank's additional investment in OpenAI. The remaining $10 billion will cover transaction costs and serve as operational and working capital for SoftBank Group.
According to the transaction arrangement, the investment will be channeled through SoftBank Vision Fund 2 in three $10 billion tranches on April 1, July 1, and October 1, 2026. This investment values OpenAI at a pre-money valuation of $730 billion and a post-money valuation of $852 billion, making it the second-largest global unicorn after SpaceX, which is valued at over one trillion dollars.
Prior to this, SoftBank Group had already invested approximately $34.6 billion in OpenAI through Vision Fund 2 and other entities. If these three $10 billion tranches are successfully delivered by October, SoftBank's total investment in OpenAI will rise to $64.6 billion, increasing its ownership stake to approximately 13%.
Considering this $30 billion additional investment as venture capital, it arguably represents the single largest capital injection into a pre-profit startup in history. Once again, Masayoshi Son is placing a massive bet on the table.
A bridge loan implies a very short repayment period and high-interest financial costs. Son must lead SoftBank Group to rearrange its assets or secure refinancing within the next 12 months.
This will inevitably include selling assets, as SoftBank indicated in its announcement: "The borrowings under this bridge financing agreement are planned to be repaid gradually before the final maturity date through the monetization of held assets and the utilization of various financing methods."
**The Ace and Hard Currency: Son's 'ATM'**
The fact that typically shrewd bankers agreed to provide this enormous unsecured loan is based not merely on SoftBank's creditworthiness or trust in Son alone. They are well aware that Son holds the hard currency of the AI era: over 90% of the shares of Arm.
Arm does not manufacture chips itself but provides chip architecture designs and IP core licensing. Essentially, Arm offers universal technical solutions, enabling chip manufacturers to rapidly develop products based on its mature architecture. In the smartphone market, Arm commands over 90% of the mobile chip market share.
With the rise of AI, Arm has once again caught a massive wave of opportunity.
As AI proliferates, computing power is no longer confined to data centers. Terminal computing power in devices like phones, PCs, and various edge devices is gaining importance. Computing power is shifting from the cloud to the endpoint—Arm's long-dominated territory.
However, the story that truly excites capital markets revolves around cloud computing power. A landmark event occurred in October 2025: OpenAI announced its in-house AI chips would adopt the Arm architecture. This signified a crack in Nvidia's dominance over the data center computing market. Following this news, Arm's stock price on Nasdaq surged to $180 per share.
Even though Arm's stock price has retreated from its peak, its total market capitalization remains firmly above $160 billion. This means the shares held by SoftBank Group are still worth a staggering $145 billion on paper. This is Son's ace in the hole; the $40 billion loan is merely a fraction of this asset's value.
The market perceives that in this historic computing power race, the entity capable of challenging industry leader Nvidia head-on is Arm, backed by SoftBank Group and its perennial gambler, Masayoshi Son.
The most paradoxical and intriguing part of this capital play is that SoftBank's massive stake in Arm was itself a huge gamble won by Son.
**Losses Are Inevitable: Missteps Are Part of the Game**
When SoftBank Group acquired Arm for $32 billion in an all-cash deal in 2016, Son's primary target was not AI, but the Internet of Things. His logic was that if everything became connected, Arm, which dominated the mobile chip architecture market, would naturally extend its advantage to all networked devices.
However, this record-breaking investment initially seemed like a misstep. The IoT revolution did not experience the anticipated "big bang," and with Arm generating only a few hundred million dollars in annual profit at the time, the $32 billion valuation appeared expensive.
The tide turned in the spring of 2023 with the AI explosion. In September of that year, Arm went public on Nasdaq at $51 per share. For this IPO, SoftBank Group sold only about 10% of its shares to the public, retaining approximately 90%.
But staying at the table means facing losses, and Son is no exception.
At the peak of the dot-com bubble in 2000, the 42-year-old Son briefly surpassed Bill Gates to become the world's richest person for three days—just 19 years after founding SoftBank at age 24. The subsequent market crash caused SoftBank's market value to plummet by 97% in a very short time, wiping out Son's fortune.
While his investment in Alibaba is legendary, Son has certainly had his misjudgments.
In late 2016, Son met with then-President-elect Donald Trump at Trump Tower in New York, announcing a planned $50 billion investment in the United States.
This meeting, which began a friendship lasting over a decade, ran overtime, delaying Son's meeting with WeWork founder Adam Neumann by nearly two hours. Their discussion was moved to a car.
Son reportedly said, "I only have 12 minutes. Let's begin!" Right there in the car, they outlined the investment framework on an iPad. By the time Son stepped out, he had committed $4 billion to WeWork—double the time of his meeting with Ma, but 200 times the investment amount.
Neumann did not become another Ma. In November 2023, the company, often criticized as a glorified sublessor, filed for bankruptcy. SoftBank's total investment of approximately $18.5 billion was almost entirely lost.
In 2019, SoftBank Group invested $1.455 billion in UK supply chain finance firm Greensill, becoming its largest shareholder. Beyond seeking returns, Son hoped Greensill could provide financing to other SoftBank portfolio companies that were still burning cash—helping them convert accounts receivable into cash flow to fund expansion and boost valuations.
The plan sounded good, but reality was harsh. Following Greensill's collapse, the investment was nearly wiped out. Furthermore, in June 2025, UBS sued SoftBank over loans associated with Greensill, creating an awkward situation for the typically reserved Japanese financier against the 160-year-old European bank known as a "wealthy safe."
**The Gambler's DNA: Pachinko, Porsche, and Chips**
Then there is the missed opportunity that led to Son's emotional moment with Huang.
In 2017, SoftBank Group invested just $4 billion to acquire nearly a 5% stake in Nvidia, becoming its fourth-largest shareholder. At the time, Nvidia was primarily known among gamers as a graphics card maker. Even Huang himself may not have fully anticipated the coming AI era—Nvidia was then betting on VR, which indeed required massive graphical processing power.
By 2019, a cryptocurrency mining crash, high graphics card inventory, and "underwhelming" VR market development caused Nvidia's stock to plunge. Son chose to exit completely, selling the entire stake for $7 billion, netting a $3 billion profit.
Unexpectedly, Nvidia's stock price soared thereafter. Even ignoring its historical peak and calculating based on its current $4.27 trillion market capitalization, a 5% stake would be worth $213.5 billion—more than five times the amount of his recent $40 billion loan.
Reflecting on selling Nvidia too early, Son later said, "I am ashamed. I was very, very firm at the time."
This was not the first time Son missed out on hundred-billion-dollar paper gains.
In the late 1990s, SoftBank was close to a deal with Jeff Bezos to acquire 30% of Amazon for $100 million, but it fell through due to a 16% valuation gap. Had that deal gone through and Son held the shares until now, that stake would be worth $678 billion.
It is worth noting that while SoftBank's $30 billion investment in OpenAI is substantial, it plays a secondary role in this funding round. The total financing for OpenAI reached $122 billion. Among the numerous investors, the largest backer was Amazon, investing $50 billion, while old acquaintance Nvidia invested the same amount as SoftBank: $30 billion.
Son's investment style may be partly influenced by his background. As a third-generation Korean-Japanese, his family faced certain exclusion and discrimination in Japan. Yet, some members of his community, operating in a legal gray area due to societal "neglect," engaged in high-risk, high-reward businesses like illegal alcohol and loan sharking.
By the time Son was in his twenties studying at UC Berkeley, his family's Pachinko parlor business was prosperous enough for him to drive a Porsche around campus.
Ultimately, the world of investment is inherently a gamble balancing risk and reward. Those who dare to place heavier bets are the ones who may eventually stand atop the highest peaks.
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