Masayoshi Son is back.
Over the past few years, when people mentioned SoftBank, they no longer remembered him as Jack Ma's "patron," but rather thought of the failed investment in WeWork, the huge losses of the Vision Fund, and the Japanese investor who was repeatedly embarrassed by the market in the tech bubble.
But today, as AI assets are being revalued, the value of Masayoshi Son's stakes in Arm and OpenAI has surged. SoftBank's stock price has soared, Masayoshi Son's net worth has risen to new heights, and he has once again become the richest man in Asia.
A $70 Billion Evaporation
People fear the unknown, so a person who has not experienced a bubble burst may feel afraid.
But not Masayoshi Son, who at 67 has witnessed the pinnacle of the internet 20 years ago and was dirt-cheap during the burst of the bubble.
Masayoshi Son was first chosen by fate in the late 1990s. At that time, the internet was like a newly discovered magic. Yahoo, web portals, e-commerce, online trading—anything related to the internet, the capital market was willing to believe that they would change the world. SoftBank also changed during that time. It was no longer just a Japanese software company but had become a huge basket filled with internet stocks. Masayoshi Son bet on Yahoo and Yahoo Japan, and SoftBank's stock price was pushed up by the bubble.
At the beginning of 2000, Masayoshi Son's wealth became surreal. During that time, his net worth could increase by about $10 billion in a week, even briefly surpassing Bill Gates, becoming the world's richest man for three days. A Korean-Japanese entrepreneur who emerged from Kyushu, with extreme faith in the internet, suddenly stood at the peak of global wealth.
After the internet bubble burst, SoftBank's stock price plummeted, and Masayoshi Son's personal fortune evaporated by about $700 billion from its peak of around $76 billion. However, Masayoshi Son was not labeled as a failure of the bubble era at that time because he still held Alibaba. In the fall of 2014, when Alibaba debuted on the NYSE, with the huge success of his investment, Masayoshi Son's personal wealth exceeded $58 billion, equivalent to the total gains from Warren Buffett's 70-year investment career.
It was the most important and successful investment in China's internet history. This investment forged Alibaba and also made Masayoshi Son.
Around 2017, the Vision Fund was established with a size close to $100 billion. Masayoshi Son became the most sought-after person by global tech startups and the most powerful purse in Silicon Valley.
He held funds from the Middle East, Apple, Qualcomm, and others, traversed through Silicon Valley, China, India, Southeast Asia, and invested in ride-sharing, food delivery, fintech, autonomous driving, and coworking. Those companies all talked about scale, network effects, winner takes all, and changing the world.
Masayoshi Son Feels Old
This time, Masayoshi Son fell from grace, starting with WeWork.
An ordinary failed investment would at most hurt profits, but WeWork hurt the market's trust in and judgment of Masayoshi Son.
At the beginning of 2019, WeWork was still valued as high as $47 billion. Its founder, Adam Neumann, had a charismatic speaking style and a big ambition, never portraying his company as just an office rental firm, but as a lifestyle, a community, a future work order.
Masayoshi Son liked these kinds of people because he was one of them. Throughout his life, he has been looking for founders who talk about business on a human scale.
But not everyone bought into this.
In August 2019, WeWork filed for an IPO. The details that were overshadowed by a grand vision in the private financing market were now put under the spotlight and presented to investors.
The company faced massive losses, heavy lease obligations, governance chaos, and excessive founder control. While it claimed to be a tech company, Wall Street increasingly felt that its core business was still leasing office space and subletting it. This business model could hardly support a $47 billion valuation.
The market began to doubt Masayoshi Son's own capabilities and forced him to reflect on his investment approach: Was it easier for those who could articulate a grand vision to take Masayoshi Son's money? Did he place too much emphasis on a founder's charisma and too little on financial discipline? Why was SoftBank willing to give such a high valuation? Why did it believe that a company that had not yet proven its profitability could shape the future through burning cash? Could a founder who is good at saying "changing the world" make Masayoshi Son overlook due diligence, valuation, and business models?
Several months later, WeWork withdrew its IPO. Adam Neumann stepped down as CEO. The valuation plummeted from $47 billion to around $8 billion.
However, at that time, SoftBank and WeWork were already in the same boat, and SoftBank had to step in to save it.
Heaven's vengeance is slow but sure, and so is the retribution of man. Once lifted to the sky by Masayoshi Son, the company suddenly became the most glaring loss on SoftBank's balance sheet.
In November 2019, SoftBank saw its first quarterly loss in 14 years. The Vision Fund recorded a nearly $9 billion loss for the quarter. Masayoshi Son admitted he had misjudged, acknowledging turning a blind eye to governance issues at WeWork. He was too eager to find the next Alibaba, too eager to replicate the victory of betting ahead of everyone's clear vision.
In 2020, the wound continued to widen. The pandemic shook the global markets, Uber fell short of its initial myth, Oyo faced layoffs and governance controversies, OneWeb filed for bankruptcy, Wirecard collapsed, and later Greensill also crumbled.
The money Masayoshi Son had scattered had basically turned into pieces on the ground.
Yet, in 2021, fortune briefly smiled upon him. Companies like DoorDash and Coupang went public, SoftBank's stock price soared, and buybacks pushed the stock even higher. That year, Masayoshi Son once again topped Japan's wealth ranking. The outside world once thought that WeWork was just an ugly episode, and the Vision Fund would eventually cover the losses with a few big wins. Masayoshi Son seemed to be proving once again that he wasn't wrong, just once again ahead of the market.
But that was just a brief revival. In the second half of 2021, the winds changed. Chinese internet regulations tightened, U.S. inflation heated up, interest rates rose, and global tech stocks faded. The market was no longer willing to pay unlimited money for the promise of a "great future." Companies whose valuations were supported by financing, scale, and imagination suddenly had to answer the same old question: When will you actually make money?
As the heavens revolve and life has its ups and downs, observing the Tao of heaven and following its course, one does well.
In 2022, Masayoshi Son truly plummeted into the deepest valley of his life.
The SoftBank Vision Fund lost about $27.5 billion in the 2021 fiscal year. In August 2022, SoftBank announced a net loss of approximately $23.4 billion for the quarter.
He said he cried for a full two weeks, "I cried every day for two weeks, I did nothing, I was very anxious, I didn't know what to do."
Reflecting on that time later, Masayoshi Son left a sincere monologue: "I realized that I was already old, my remaining life is limited, but I haven't achieved anything yet, and I cried a lot. I asked myself, do I really have to grow old like this and then die? Everyone calls me a successful businessman? An entrepreneur? A business master? But I really feel very sad for myself."
SoftBank has also started to contract, with new investments slowing significantly, the Vision Fund team facing layoffs, and assets being continuously monetized. Alibaba, the once biggest contributor who helped Masayoshi Son turn the tide, has also been gradually reducing its holdings by SoftBank to improve its financial structure. Masayoshi Son's business empire is now besieged from all sides, and his father has also had his life taken by cancer.
In the past few years, those companies that excited Masayoshi Son have turned into a series of write-downs and losses. He said, "I would rather accept my own stupidiy and ignorance, accept the wrong decisions I made, so that I can learn from them." He admitted that he was too happy in the past to see huge profits and now feels ashamed. He also said that if he had been more selective and made better investments at the time, the damage would not have been so great.
Many people say that the Masayoshi Son of those years was very different from the familiar Masayoshi Son. Masayoshi Son has become quieter, and he rarely reappears in the public eye.
He said SoftBank is entering "defense mode," and he also said he will focus on Arm in the coming years.
Looking back now, this is another great investment by Masayoshi Son.
AI Pardoned Masayoshi Son
But initially, Arm didn't seem like a destined successful deal, and this deal put Masayoshi Son under pressure.
In the summer of 2016, SoftBank spent up to $32 billion in cash to acquire 90% of Arm's shares, offering a 40% premium.
At that time, Arm was certainly a good company. But most of the funds used for the acquisition came from bank loans, from SoftBank, which was already burdened with debt, raised with 1.5 times leverage. Many investors doubted whether Arm was really worth it. Even after Arm was taken private by SoftBank, investment increased, profit margins declined, and performance deteriorated significantly, with SoftBank almost selling Arm to NVIDIA.
It wasn't until ChatGPT that the market re-understood computing power, and the AI trend allowed Arm to shine. In September 2023, Arm went public on the Nasdaq with an IPO valuation of around $54.5 billion. From around 14 trillion yen at the end of March 2023, SoftBank's NAV rose to around 34 trillion yen by June 2024. Arm now accounts for the bulk of SoftBank's stock value. SoftBank said in its annual report that Arm's returns to the group's shareholders reached 24.6 trillion yen, about a 10x return.
If Arm was the lifeline that pulled Masayoshi Son out of the mud, then OpenAI might be his redemption.
In January 2025, OpenAI, SoftBank, Oracle, and MGX announced the Stargate project, planning to build a large-scale AI infrastructure in the United States, with a potential investment of up to $500 billion over the next four years.
Subsequently, SoftBank's investment in OpenAI started to escalate significantly.
In 2025, SoftBank completed an investment of approximately $30 billion in OpenAI. By February 2026, SoftBank signed an additional $30 billion investment agreement with OpenAI. According to SoftBank's announcement, after the additional investment is completed, SoftBank's total investment in OpenAI is expected to reach $64.6 billion, with a stake of approximately 13%. In April 2026, SoftBank first executed the initial phase of this additional investment, amounting to $10 billion.
In March 2026, SoftBank secured a $40 billion bridge loan, mainly for future OpenAI investments. It also divested or monetized other assets, using Arm shares, SoftBank's telecom assets, and other holdings as financing leverage.
This investment is very "Masayoshi Son," once again pledging SoftBank's most valuable assets to secure a ticket to the next round of the future.
In the Internet era, he bet on Yahoo and Alibaba; in the mobile Internet era, he heavily invested in telecom, Sprint, and Arm; during the Vision Fund era, he scattered money among startups telling grand stories. As the AI era unfolds, he is propelling SoftBank towards OpenAI and AI infrastructure.
By the end of March this year, SoftBank disclosed that its cost of investment in OpenAI was approximately $34.6 billion, with a fair value of around $79.6 billion, and accumulated investment returns of about $45 billion.
Most recently, SoftBank's stock price has soared, surpassing Toyota in market capitalization, making it one of the most sought-after companies in Japan. Masayoshi Son has once again become the richest man in Asia.
Fortune is once again on Masayoshi Son's side.
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