Son Masayoshi, who went bankrupt after being deceived by good stories, is waiting for his next Alibaba.

Masayoshi Son, Ruined by Good Stories, Now Waits for His Next Alibaba

By Zhangsheng BeatZ

Source:

Reprint: Mars Finance

Masayoshi Son is back.

In the past few years, when people mentioned SoftBank, they no longer talked about him as Jack Ma’s “mentor.” More often, they thought of WeWork’s failure as an investment, the massive losses of the Vision Fund, and that Japanese investor who was repeatedly slapped in the face by the market during the tech bubble.

But today, AI assets are being repriced, and the value of Arm and OpenAI shares in Son’s hands is rising sharply. SoftBank’s stock surged, and Masayoshi Son’s net worth climbed back to a high level—once again making him Asia’s richest person.

Evaporated $70 billion

People fear the unknown. So if someone has never experienced a bubble burst, they may be afraid.

But Son is not like that. At 67, he lived through the internet boom peak 20 years ago—and when the bubble burst, he was also left with mud all over him.

Son’s first stroke of good fortune came in the late 1990s. At the time, the internet felt like a newly discovered kind of magic. Yahoo, portal websites, e-commerce, online transactions—anything that touched the web—made the capital markets believe they could rewrite the world. SoftBank changed too. It was no longer just a Japanese software company; it became a huge basket filled with internet stocks. Son bet on Yahoo, and also on Yahoo Japan. SoftBank’s stock price was pushed higher and higher by the bubble.

In early 2000, Son’s wealth became almost unbelievable. During that period, his fortune could grow by about $10 billion in a single week, even briefly surpassing Bill Gates and becoming the world’s richest person for three days. A Korean-Japanese entrepreneur from Kyushu, driven by extreme confidence in the internet, suddenly stood at the very top of global wealth.

After the internet bubble burst, SoftBank’s stock price kept falling, and Son’s personal fortune—after peaking at about $76 billion—lost roughly $70 billion in value. Yet Son was not written off as a bubble-era loser, because he still held Alibaba. In the fall of 2014, Alibaba listed on the NYSE. Thanks to a major success from an investment, Son’s personal wealth exceeded $58 billion—roughly equivalent to the total returns of Buffett’s 70-year investment career.

That was the most important and successful venture capital investment in China’s internet history. It forged Alibaba—and made Son.

Around 2017, the Vision Fund was established, with a size close to $100 billion. Son became the person global tech startups most wanted to meet, as well as Silicon Valley’s most powerful money bag.

He brought funds from the Middle East, Apple, Qualcomm, and others, and traversed Silicon Valley, China, India, and Southeast Asia—putting money into ride-sharing, food delivery, fintech, autonomous driving, and co-working spaces. Those companies all talked about scale, network effects, winner-takes-all, and changing the world.

Son felt like he was getting old

This time, Son’s fall from his throne began with WeWork.

A normal failed investment might at most hurt profits, but WeWork harmed market trust in Son—and harmed his judgment.

In early 2019, WeWork’s valuation was still as high as $47 billion. Its founder, Adam Neumann, spoke with charisma and had big ambitions. He never portrayed his company as simply an office-rental business. Instead, he described it as a lifestyle, a community, and a future work order.

Son liked this kind of person, because he himself was like that. He spent his whole life searching for founders who could talk about business in a human scale.

But not everyone bought into it.

In August 2019, WeWork filed its IPO prospectus. The details that had been hidden behind grand visions in private funding were now placed under the spotlight, laid out in front of investors.

The company had massive losses, heavy lease burdens, and chaotic governance, with the founder wielding too much power. It claimed to be a technology company, but the more Wall Street looked at it, the more it felt its core business was still leasing office buildings and then splitting and subleasing them. That business model was difficult to justify a $47 billion valuation.

The market began to doubt Son’s own ability, forcing him to reflect on his investment approach: Would it be easier for people who talked big about grand visions to take Son’s money? Had he overvalued a founder’s “charisma,” while underestimating financial discipline? Why was SoftBank willing to give such high valuations? Why would it trust a company that had not yet proven its profitability—believing it could burn cash to build the future? If a founder could just say “change the world,” would that be enough for Son to put aside due diligence, valuation, and business models?

A few months later, WeWork withdrew its IPO. Adam Neumann stepped down as CEO. The valuation fell from $47 billion down to around $8 billion.

But by then, SoftBank and WeWork were already stuck on the same sinking ship and could not get off. SoftBank had no choice but to step in and save it.

Heaven hates excess fullness, while humans hate absolute completeness. The companies that Son had once elevated to the clouds suddenly became the most glaring losses on SoftBank’s reports.

In November 2019, SoftBank posted its first quarterly loss in 14 years. The Vision Fund’s quarterly loss was close to $9 billion. Son admitted he had made the wrong judgment, and he also admitted he had ignored the governance problems at WeWork. He was just too eager to find the next Alibaba, and too eager to replicate that kind of victory from early bets made before everyone else could see clearly.

In 2020, the wounds kept widening. The pandemic hit global markets. Uber failed to live up to its early myth. Oyo fell into layoffs and governance disputes. OneWeb filed for bankruptcy. Wirecard collapsed. Later, Greensill also fell apart.

Most of the money Son threw out became scattered fragments.

But in 2021, fortune briefly looked back at him. Companies like DoorDash and Coupang went public, SoftBank’s stock surged, and buybacks pushed the share price even higher. That year, Son returned to the top of Japan’s wealth ranking. For a time, outsiders thought WeWork was just an ugly detour, and that the Vision Fund could still cover losses with a few big wins. It seemed Son was going to prove he wasn’t wrong—he was just arriving earlier than the market again.

But that was only a brief rebound. Starting in the second half of 2021, the winds changed. Chinese internet regulation tightened, U.S. inflation warmed up, interest rates rose, and global tech stocks retreated. The market no longer wanted to pay endless money for stories about “a big future.” Those companies that had relied on financing, scale, and imagination to support their valuations suddenly had to answer the same old question: When exactly will you make money?

There is a cycle to heaven and earth, and life has ups and downs. Following the law of heaven in observing the heavens, acting according to the course of heaven—there’s nothing more to do.

In 2022, Son truly fell into the biggest low point of his life.

In SoftBank’s Vision Fund, the fiscal year 2021 loss was about $27.5 billion. In August 2022, SoftBank again announced a quarterly net loss of about $23.4 billion.

He said he cried for a full two weeks. “During those two weeks, I cried every day. I didn’t do anything. I was anxious—I didn’t know what to do.”

Later, when recalling that time, Son left behind a sincere monologue: “I thought about how I’m already old, and my remaining life is limited, but I haven’t accomplished anything. I cried terribly hard. I asked myself: am I really going to grow old like this, and then die? People call me a successful businessman? An entrepreneur? A master of commerce? But I really feel heartbroken for myself.”

SoftBank also began to shrink. New investments slowed dramatically. The Vision Fund team faced layoffs, and assets were continuously monetized. Alibaba—the biggest contributor that once helped Son turn things around—was gradually reduced by SoftBank as it improved its financial structure. Son’s business empire was besieged on all sides, and his father also lost his life to cancer.

The companies that had thrilled Son in the past few years turned into a string of impairments and losses. He said, “I would rather accept my foolishness and ignorance, accept the wrong decisions I made—so that I can learn from them.” He admitted that when he saw huge profits in the past, he was too happy; now he feels ashamed. He also said that if he had been more selective and invested better at that time, the damage wouldn’t have been so great.

Many said that Son in those years no longer looked much like the Son people were familiar with. Son became quieter. He rarely reappeared in the public eye.

He said SoftBank would enter a “defensive mode.” He also said that in the coming years, it would put its energy into Arm.

Today, it looks like another great investment by Son.

AI Has Granted Masayoshi Son a New Lease on Life

But at the beginning, Arm did not look like a deal destined for success. This transaction subjected Son to intense pressure.

In the summer of 2016, SoftBank spent as much as $32 billion in cash to acquire 90% of Arm, offering a 40% premium.

At that time, Arm was indeed a good company. But most of the acquisition funds came from bank loans. SoftBank, which was already carrying debt, raised the money with 1.5x leverage. Many investors questioned whether Arm was truly worth it. Even after Arm was taken private by SoftBank, investment increased and profit margins declined. Performance deteriorated significantly at one point. SoftBank even nearly sold Arm to Nvidia.

It wasn’t until after ChatGPT that the market re-understood computing power. The massive river of AI unleashed Arm’s brilliance. In September 2023, Arm listed on Nasdaq, with an IPO valuation of about $54.5 billion. From roughly ¥14 trillion at the end of March 2023, SoftBank’s NAV rose to about ¥34 trillion by June 2024. Arm already makes up the largest portion of the value of SoftBank’s holdings. In its annual report, SoftBank stated that the return Arm brought to the group’s shareholders reached ¥24.6 trillion—about a 10x return.

If Arm pulled Son out of the mud, then OpenAI might be his comeback battle.

In January 2025, OpenAI, SoftBank, Oracle, and MGX announced the Stargate project, planning to build large-scale AI infrastructure in the United States, with planned investment of up to $5000 billion over the next four years.

Next, SoftBank’s investment in OpenAI began to accelerate sharply.

In 2025, SoftBank completed an investment in OpenAI of about $30 billion. By February 2026, SoftBank had also signed an additional investment agreement with OpenAI for $30 billion. According to SoftBank’s announcement, after the additional investment is completed, SoftBank’s cumulative investment in OpenAI is expected to reach $64.6 billion, with an equity stake of about 13%. In April 2026, SoftBank executed the first tranche of this additional investment, amounting to $10 billion.

In March 2026, SoftBank signed a $40 billion bridge loan, mainly to support future OpenAI investments. It also sold or monetized other assets, using Arm shares, SoftBank’s telecom assets, and others as financing support.

This was very much Son’s style. Once again, he took SoftBank’s most valuable assets and exchanged them for the next round of future entry tickets.

In the internet era, he bet on Yahoo and Alibaba. In the mobile internet era, he heavily positioned into telecom, Sprint, and Arm. In the Vision Fund era, he scattered money into startups that told huge stories. And in the AI era, he pushed SoftBank toward OpenAI and AI infrastructure.

At the end of this March, SoftBank disclosed that its OpenAI investment cost was about $34.6 billion, with a fair value of about $79.6 billion, and cumulative investment returns of about $45 billion.

Recently, SoftBank’s stock surged. Its market value at one point exceeded Toyota, making it one of Japan’s most pursued companies by the market. Masayoshi Son has also once again become Asia’s richest person.

Once again, fortune has stood on Masayoshi Son’s side.