SoftBank borrows another $10 billion, and the payment to OpenAI must be made on October 1. OpenAI has accumulated a negative free cash flow of $278 billion over five years. Arm stock has propped up a safety cushion for SoftBank, but the interest bill jumped by 147.3 billion yen in a single quarter. Wall Street is essentially using junk-bond interest rates to price this waiting game for the quoted price. (Backgrounder: OpenAI expects revenue to grow by 10x over the next five years—but compute spending will be even higher.) (Additional background: a white-hat hacker gained access to OpenAI’s internal code repository via Claude; the bounty was only $6,500.) The WeChat public account’s in-depth longform post reveals that in order to raise the $10 billion that must be paid to OpenAI on October 1, Son Masayoshi is urgently issuing high-risk bonds in the public market. And this is only the tip of the iceberg of his $100 billion-plus bet—OpenAI’s cumulative negative cash flow over the next five years totals $278 billion. This investment has turned into a deadly race against the maturity date, and the only “cashable” card SoftBank has is Arm. Son Masayoshi has gone back to borrow. This time it’s $10 billion plus €1 billion—put entirely into OpenAI. On September 21, Reuters uncovered SoftBank’s latest bond issuance documents. Citi and JPMorgan sat side by side in the underwriters’ column, preparing to pitch these high-risk notes to the public market. SoftBank’s issuer credit rating is still at BB+. In more polished terms, that is “high-yield debt,” but really, it’s junk bonds. The issuance timetable is extremely tight: on September 24 they lock in the interest rate, on the 29th the funds are credited, and then on October 1—down to the penny—this money must be transferred into OpenAI’s account. This is the third scheduled installment of investments that both sides agreed on. Hundreds of millions of dollars flow through and leave immediately; on SoftBank’s books, the cash can only stay for two days. A tech fanatic who claims he can see the next thirty years is counting his cash flow day by day. He never used to rush like this when making big bets. In 1999 he met Jack Ma and invested $20 million. At the time, everyone thought he was crazy—but he was using his own idle money. Wins and losses were his to bear, and he could wait for a full fifteen years. Back then, time was his ally. Now everything has flipped. The grand narrative about changing the world is still on the surface. Under the hood, he is racing the calendar before each debt repayment deadline. On February 27, SoftBank and OpenAI signed the final agreement. The total $30 billion in additional investment was split into three tranches—$10 billion each—delivered on April 1, July 1, and October 1, respectively. After the last payment is settled, SoftBank’s total outlay in hard cash into this company will reach $64.6 billion, equivalent to about 13% equity. $64.6 billion is twice what SoftBank spent in 2016 to acquire Arm. In this round, OpenAI’s pre-money valuation surged to $730 billion, far surpassing SoftBank Group’s own market value. Staged payments are the compromise: OpenAI locks in future funding for roughly the next half year, while SoftBank squeezes out breathing room for itself. But the price is that every three months, SoftBank has to scramble to raise another $10 billion among financial institutions. The schedule is tight to the day: the $10 billion on October 1 must arrive. What pushed Son Masayoshi to make up his mind is a roadshow deck sent to top investors. The file shows that OpenAI expects revenue of $36 billion in 2026, expanding to $350 billion by 2030, with $840 billion in cumulative gains over five years. A massive $122 billion funding round finalized in March pushed its valuation to $852 billion. Meanwhile, Son’s rival, Anthropic, is planning to list. Son is closely watching the rapidly inflating valuation, convinced he has secured the most crucial seat in the coming era of superintelligence. But behind this deck are bottomless holes. In the same forecast, over the five years from 2026 to 2030, OpenAI’s accumulated negative free cash flow will total $278 billion. Compute power and data center infrastructure alone will consume $856 billion—one line item exceeds the total of all estimated revenue over the five-year period. Every step of technological iteration is bleeding money by the billions. That is why it needs Son Masayoshi. A company with enormous ambition but persistent cash burn urgently needs a buyer willing to front it with the credit of an entire financial empire. Yet the assets SoftBank gets in return are, for now, a pool of dead water. The agreement is clear: all subscribed shares are preferred stock, which cannot be converted into freely tradable shares until after the company rings the bell for a public listing. Off-exchange, almost no institutional investors have an appetite for taking on a plate worth hundreds of billions. Converted to a $64.6 billion position certificate, it is only a stack of paper locked inside a safe before the real listing and the bell. Son Masayoshi is no stranger to waiting. In 1995 he bet on Yahoo; at one point the paper gain exceeded three hundredfold, briefly putting him on the seat of the world’s richest person. The $20 million he put into Alibaba lay underwater for more than a decade before he finally waited for the unforgettable bell at the New York Stock Exchange. These two headline battles shaped his faith in big trends—but also made him overlook a premise: back then, whether it was Yahoo or Alibaba, the money propping things up was his own. His own idle money could be spent; the worst-case outcome was simply taking an accounting loss and exiting the table. As long as he didn’t leave the table, there was always a chance to outlast until miracles happened. In the official announcement on February 27, he said with zero hesitation: “AI is changing the world at an unprecedented speed. OpenAI is a clear leader, with world-class technology and an unparalleled global user base. We are confident in its continued growth.” He explained why he was bullish—but said nothing about where the funding would come from. OpenAI burns through $278 billion over five years—why is SoftBank adding more? The grand vision belongs to the era. The cost of realizing it is written into another contract full of borrowing terms. On March 27, SoftBank signed an unsecured bridge loan totaling $40 billion. The lead arrangers are JPMorgan, Goldman Sachs, Mizuho, Sumitomo Mitsui, and Mitsubishi UFJ. Behind them is a syndicate of more than twenty international banks. The entire borrowing has no pledge of any tangible assets; the term is only one year, with the maturity date set for March 25, 2027. Wall Street is willing to allow such a huge exposure mainly based on SoftBank’s corporate credit—and on Arm sitting at the bottom layer of the balance sheet. In credit markets, a bridge loan is precisely a tool used for temporary transition. Its purpose is to fill the gap until long-term capital is in place. But SoftBank draws down extremely fast. It takes $10 billion on April 1 to deliver the first tranche, and then draws another $10 billion on July 1 for the second tranche. In April, SoftBank also additionally withdrew $10 billion as a liquidity reserve. Of the $40 billion credit line, it quickly drew $30 billion. More subtly, it’s September. On September 9, SoftBank announced it would prepay the outstanding balance of $25.9 billion on September 15. This loan was not fully settled; about $4.1 billion remained on the books as a tail. As for the source of the funds to fill more than $20 billion of that gap, the official announcement said nothing. This is not a move born of panic. As early as the initial investment announcement on February 27, SoftBank had already written that the payments would be funded first by the bridge loan, and then replaced using existing assets and long-term financing. At the end of August, the market heard that Mizuho Bank is taking the lead on a…