After committing over $60 billion, some insiders at Softbank Group Corp (SFTBY.US) are growing uneasy about Masayoshi Son's fixation on OpenAI. When the company began investing billions into OpenAI last year, executives reportedly questioned Son about the potential consequences if the ChatGPT developer were to fail, even if the likelihood seemed low. Son, who has expressed strong belief that Sam Altman is leading the century's most significant technological shift, dismissed such concerns abruptly, leading subordinates to avoid raising the topic again.
As OpenAI potentially moves toward a public listing this year, recent breakthroughs by rival Anthropic have sparked market doubts about OpenAI's position. Some SoftBank insiders are anxious about the firm's more than $60 billion investment commitment and wary of their leader's near-idolization of Altman, viewing the relationship between the two founders as one-sided and risky. Interviews with approximately ten sources reveal a key worry: Son is concentrating too much of SoftBank's capital on a single company, particularly one facing commercial, reputational, and legal challenges.
SoftBank has sold assets, including its stake in Nvidia (NVDA.US), and refrained from investing in other AI model firms, deepening its reliance on OpenAI. While such concerns remain a minority view within SoftBank, some executives fear a repeat of the WeWork debacle, where Son's fervent support for a charismatic founder led to over $14 billion in write-downs after ignoring warning signs. This time, the stakes are substantially higher.
SoftBank stated it has "high confidence" in OpenAI and its leadership, citing a "strong strategic partnership" based on shared views on AI's trajectory and global scaling needs. OpenAI separately noted the two companies enjoy an "excellent relationship" and are among each other's closest partners.
On paper, SoftBank is currently benefiting from the investment. Last week, it announced annual profit surged over fourfold to a record 5 trillion yen (approximately $320 billion), largely driven by gains from OpenAI's rising valuation. However, Son's motivation extends beyond short-term financial returns; he aims to position SoftBank at the core of the next major technological leap. From the outset, he has firmly believed in Altman's vision of Artificial General Intelligence (AGI)—advanced AI with human-level capabilities that could accelerate breakthroughs in science and medicine that might otherwise take decades.
SoftBank CFO Yoshimitsu Goto remarked at an earnings briefing, "We are focused on the next 30 years, and the AI revolution is just beginning. We want to be a valuable company at the heart of this revolution." Supporters point out that OpenAI remains a pioneer in AI services, and many tech investors note SoftBank is not alone in making large AI bets.
Ben Narasin, founder and general partner at Tenacity Venture Capital, commented, "Large checks align with their risk-reward logic. You can't win without playing, and once in the game, you must take real risks." If OpenAI achieves a valuation exceeding $1 trillion in an IPO, Son could secure a "second legend" akin to his early bet on Chinese e-commerce giant Alibaba.
Yet, given intensifying competition, such a blockbuster IPO is not guaranteed. Anthropic's Claude is challenging OpenAI's dominance, with its new Mythos model reportedly capable of identifying and exploiting vulnerabilities in key software. Google's (GOOGL.US) Gemini is also catching up rapidly, excelling in scientific reasoning. Late last month, sources indicated Anthropic is fielding investor offers that could more than double its valuation to over $900 billion, potentially surpassing OpenAI as the world's highest-valued AI startup.
As investor concerns grow over OpenAI's ability to maintain its lead, SoftBank's stock has fallen over 20% since hitting a record high last October. In March, S&P Global revised its outlook on SoftBank to negative, citing that its massive bet on OpenAI could drain liquidity and weaken asset credit quality. Earlier this month, sources said SoftBank scaled back a planned $10 billion margin loan scheme collateralized by its OpenAI stake due to lender hesitation.
Habib Imam, managing partner at venture firm Menlo Park Capital and a former SoftBank employee, noted similarities between the WeWork and OpenAI investments, including "key person" leadership and aggressive spending for grand visions. For Son, this latest investment is not just a bet on OpenAI but "a bet on a worldview about AGI," Imam stated, adding, "You can't hedge a worldview."
Some insiders argue this is precisely the problem, noting Son's tendency to develop strong personal admiration for founders and fully embrace their aggressive expansion plans. Despite owning over a 10% stake, SoftBank holds no board seat or observer position at OpenAI—a level of ownership that typically warrants board representation. Due to OpenAI's unique structure stemming from its nonprofit origins, other external investors like Microsoft (MSFT.US) and Amazon (AMZM.US) also lack board seats. It remains unclear whether Son ever sought a seat. Nonetheless, some worry SoftBank has minimal influence over a company it heavily depends on.
Beyond chip designer Arm (ARM.US), in which it holds about a 90% stake, OpenAI has become a central pillar in SoftBank's current investment portfolio. It constitutes a major portion of Vision Fund 2—now SoftBank's primary fund—and contributed most of the investment gains last fiscal year. Insiders are uneasy about this limited influence, especially given their familiarity with Son's typically hands-on control.
In Japan, Son is widely regarded as one of the most visionary and unconventional entrepreneurs, a status shaped by his Korean heritage and career challenging mainstream institutions and critics. In 2001, SoftBank's low-cost broadband service is credited with boosting internet adoption in Japan. In 2006, he defied skepticism over acquiring Vodafone Japan for $15 billion, later proving his judgment correct by securing exclusive iPhone sales rights, turning the business into a cash flow engine.
Alibaba's 2014 IPO became a hallmark of Son's career. His $20 million investment in 2000 transformed into immense wealth as Alibaba went public valued over $160 billion, with SoftBank holding about one-third of the company. This success cemented Son's reputation as a venture capital legend and aided SoftBank's $32 billion acquisition of Arm in 2016. The following year, he launched the $100 billion Vision Fund, attracting Saudi and UAE sovereign wealth funds and reshaping global finance with unprecedented investments in startups like Uber (UBER.US) and DoorDash (DASH.US).
Reportedly, when Son first met Altman, SoftBank was flush with Vision Fund capital, while OpenAI, then a nonprofit, was not short on funds. Son said he was captivated by Altman's AGI vision. Recalling their 2017 Tokyo meeting, Son stated, "I immediately said, I believe in you, I want to invest. From day one, I was a firm believer. I never doubted."
However, the Vision Fund later faced mounting challenges, and Son became distracted by other issues. In January 2019, the fund sold nearly 5% of its Nvidia stake for $3.3 billion. Son later publicly expressed regret as Nvidia's market value soared. Later that year, WeWork's collapse and losses from Greensill and Katerra forced him to scale back new investments. Son described this as a "dark period," confessing to days of tears and self-doubt.
As Son retrenched, OpenAI sought funding for its next-generation model. In July 2019, Microsoft led with a $1 billion investment. By the time Son was ready to re-enter, OpenAI had become highly sought-after following ChatGPT's 2022 launch, with backers like Peter Thiel and Sequoia Capital already securing stakes. SoftBank's investor relations team frequently fielded shareholder queries about why the firm hadn't invested in OpenAI.
Son later said OpenAI's GPT technology helped him overcome the emptiness from Vision Fund losses, renewing his sense of purpose to support the impending AI revolution. While SoftBank had already invested in Arm, Son wanted a seat at the "main table." Sensing cooling relations between Altman and Microsoft—as Microsoft hesitated to continually fund OpenAI's expanding ambitions—Son seized an opportunity.
In 2024, SoftBank finally secured a $500 million investment in OpenAI. Though a small fraction of OpenAI's post-funding $157 billion valuation, for Son, it was a chance to enter the inner circle. Sources say he brought not just capital but also envisioned Arm helping break Nvidia's monopoly in AI chips, making Altman's AGI vision more feasible.
After securing the allocation, Son soon publicly mocked Microsoft's AI product Copilot, repeatedly emphasizing OpenAI's superiority. "What's a copilot without a pilot?" he reportedly quipped more than once. Ultimately, Son met his match—someone who responded to his ambitions with even grander figures. When Son suggested they might need $3 trillion for AI chip and infrastructure development, Altman reportedly countered with a higher number without flinching.
Their relationship quickly deepened. In January 2025, Son and Altman stood together at the White House as President Trump announced the launch of the Stargate Project—a $500 billion initiative by OpenAI, SoftBank, Oracle (ORCL.US), and Abu Dhabi-backed MGX to build AI data centers across the U.S. Three months later, SoftBank announced an additional $30 billion investment in OpenAI, its largest ever in a private company.
In his annual letter to shareholders in July 2025, Son wrote, "I firmly believe OpenAI is on track to become the world's most valuable company. I am going all in." However, SoftBank executives encountered difficulties finding suitable sites for the Stargate Project meeting power, water, and proximity requirements. Consequently, despite negotiations with lenders and funds like Mizuho, JPMorgan, and Apollo Global Management, securing financing proved challenging.
Sources last year said Son grew anxious over slow progress and pushed for data center-related deals. He even considered acquiring data center operator Switch for $50 billion to provide a "one-stop" solution, though the plan was later abandoned. Despite these hurdles, sources said Altman approached SoftBank early this year to finalize another mega-funding round.
In February, SoftBank announced a further $30 billion investment in OpenAI, executed in three tranches, bringing its total commitment to over $60 billion and pushing OpenAI's valuation to $730 billion—more than four times its value at the time of the initial 2024 investment. Less than a week after SoftBank's increased commitment, S&P downgraded its outlook on SoftBank from stable to negative. The news triggered a spike in its credit default swaps (CDS), potentially raising borrowing costs, just as SoftBank had signed a record $40 billion loan to support AI investments.
To fund this investment, SoftBank accelerated sales of core assets like Nvidia and T-Mobile USA (TMUS.US) shares. It also had to forgo other potential investments and acquisitions. Sources indicated that due to a lack of new deals, Vision Fund began cutting about 20% of its staff starting last September. These sacrifices have heightened concerns that SoftBank's future is increasingly tied to Altman.
Altman has a history of fractured business partnerships. In 2023, he was briefly ousted from OpenAI's board over concerns about transparency, though he was swiftly reinstated with Microsoft's support. OpenAI co-founder Elon Musk sued Altman, alleging he deviated from their shared altruistic mission by turning the company for-profit. A jury dismissed Musk's claims on Monday, though the billionaire has stated he will appeal without providing details.
OpenAI has also clashed with Microsoft over partnership terms, with the two increasingly competing directly in various areas. Sources last week said its partnership with Apple (AAPL.US) has grown tense as well. Several SoftBank insiders expressed concern that Son is being sidelined and not receiving the strategic partner-level respect he expected, not just due to the lack of a board seat shared with other major investors.
Meanwhile, Altman has expanded the Stargate Project to countries like the UAE and South Korea without SoftBank's involvement. Son was notably absent from recent updates on the high-profile AI device project io, which originally stemmed from discussions between Son, Altman, and former Apple design chief Jony Ive. OpenAI acquired io last year, and its website features only a photo of Altman and Ive in the U.S., with Ive's arm around Altman's shoulder. The two also jointly presented the project through an unusual promotional video.
SoftBank is advancing its own initiatives, including a $5.4 billion acquisition of ABB Ltd.'s industrial robotics business. In March, it announced plans to launch a large data center project in Ohio. Earlier this month, sources said Son discussed a multi-billion-dollar AI data center investment plan in France with President Emmanuel Macron.
Some investors believe SoftBank should hedge its AI risk by investing in OpenAI competitors like Anthropic. However, CFO Goto stated last week the company currently has no such plans, noting, "While we do not rule out any possibilities, in generative AI, we believe we should advance through an extremely solid partnership with OpenAI." He added that companies like Amazon and Nvidia also made substantial investments in the latest funding round.
Sources indicate that over the past decade, the departure of several senior SoftBank figures, including outspoken external directors like Fast Retailing founder Tadashi Yanai and Nidec founder Shigenobu Nagamori, means there has been little internal resistance to escalating commitments to OpenAI. Corporate governance expert and external director Yuko Kawamoto resigned in 2021, calling in her departure memo for more "dissenting voices" within the company. In her resignation letter published on SoftBank's website, she wrote, "It would be better if the obligation to raise objections or opposition when necessary were more common within SoftBank Group."
Those close to Son say his dedication to Altman stems from a desire to cement his historical legacy and compensate for missing the first wave of the AI gold rush. Son often describes his life and career as a series of battles against the odds. In his youth, he was diagnosed with chronic hepatitis B when effective treatments were scarce. In business, he has demonstrated resilience, surviving the 2000 dot-com crash and high-profile Vision Fund setbacks, each time returning with larger bets.
Outside Japan, Son's investment record is sometimes viewed as "mixed," with his legendary Alibaba bet seen as a one-off. Menlo Park Capital's Imam noted, "Alibaba was a career-defining success," adding that AI investments are different, as "no single AI investment can provide the portfolio-wide safety net that Alibaba did over the past 20 years."
Even in Japan, some critics view Son as an unreliable backer who inflates valuations with grand promises. Son himself often embraces such skepticism, describing his career as a series of "impossible dreams" realized precisely because he ignored naysayers. Richard Kaye, an investment manager at Comgest Asset Management Japan and a long-term SoftBank investor, believes that being "misunderstood" is a key driver for Son. Kaye observed, "Does Son still feel misunderstood, perhaps by Western markets, or even the Japanese market? I would say, yes."
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