Gambling big with OpenAI, Masayoshi Son has turned the tables again.

OpenAI has been reported to be negotiating a new round of financing with an astonishing valuation of $500 billion, directly driving SoftBank's stock price to a historic high, up about 75% this year. This article originates from a piece written by Wall Street Journal, organized, translated, and authored by Foresight News. (Background: A comprehensive summary of OpenAI's strongest GPT-5 release: free access, highlights, gpt-5, gpt-5-mini, and gpt-5-nano API pricing) (Background supplement: OpenAI's open-source weight model GPT-OSS: How does Apache 2.0 crown developers? The CoT thinking chain unlocks security sovereignty) The Vision Fund 2 has suffered a massive loss of $22 billion, but the soaring valuation of OpenAI has allowed SoftBank's stock price to reach new highs, with Masayoshi Son once again pulling off a dramatic turnaround from the brink of crisis. On Tuesday, SoftBank Group's stock price hit a historic high of 14,825 yen, with a market capitalization reaching $146 billion, and its stock price has increased by about 75% this year. All of this is attributed to Masayoshi Son's big bet on OpenAI. On August 12, according to The Information, OpenAI is negotiating with investors, including Thrive Capital, regarding the sale of employee stock options, with the company's valuation reaching $500 billion—double that of the recent round of funding. This valuation leap has nearly doubled SoftBank's previous investment value of $9.7 billion in OpenAI, which is crucial for offsetting the Vision Fund 2's cumulative investment losses of up to $22 billion. A high-leverage gamble SoftBank's Vision Fund 2 has performed incredibly poorly. Since its launch in 2019, the fund has incurred a total loss of $22 billion across investments in 280 different companies, accounting for nearly one-third of its invested capital. However, the investment in OpenAI is expected to change this situation. SoftBank's investment in OpenAI has employed its typical "Masayoshi Son-style" high-leverage approach. Reports indicate that SoftBank obtained shares of OpenAI through complex financial maneuvers—the Vision Fund 2 borrowed billions from SoftBank itself, which in turn borrowed from Japanese banks. Simultaneously, the fund also secured billions in loans from private lending institution Apollo, which will receive priority repayment. A bigger bet is still to come. SoftBank is expected to invest an additional $22.5 billion in OpenAI by the end of this year, with this transaction locked in when OpenAI was valued at $260 billion. If the deal goes through, SoftBank could hold up to 12% of OpenAI's shares. This also means that SoftBank might already be in profit before investing this amount, but this requires OpenAI to complete its transition to a profit-making structure. It is still unclear whether this $22.5 billion in future equity will be placed on the Vision Fund 2 or on SoftBank Group's balance sheet. SoftBank executives have stated that no decision has been made yet, but this choice will directly impact the returns for SoftBank shareholders and Masayoshi Son personally. Masayoshi Son's "personal gamble" Unlike the first Vision Fund, there are no external investors involved in Vision Fund 2. After the fund failed to raise external capital, Masayoshi Son secured a 17.25% share for himself. This arrangement deeply ties his personal wealth to the fund's performance. Public records in Japan show that Masayoshi Son has also pledged about 9 million shares of SoftBank stock he personally holds as collateral for loans. However, according to the fund's terms, he cannot receive any distributions until the fund's realized and unrealized value exceeds the investment cost by 30%, and considering the fund is currently in severe losses, this remains a distant goal. Masayoshi Son's personal stock arrangement has raised concerns about corporate governance. David Gibson, a stock analyst at MSFT Financial, told the media that this arrangement reduces the potential returns shareholders might gain from the OpenAI investment, stating, "From a corporate governance perspective, this is a disaster." The high concentration risk under the shadow of WeWork This massive investment has also put SoftBank at risk of high concentration again. If the additional investment is completed, a single asset from OpenAI could account for 34% of the total scale of Vision Fund 2. This inevitably recalls SoftBank's disastrous investment in WeWork a few years ago. After that, the fund's financial officer had promised to ensure that the fund would not be "overly concentrated." Now, SoftBank seems to be placing a large bet on a single star project once again. As it stands, this investment is on the path to a huge victory. But as reports point out, it could also end in a similar tragedy. Related reports: OpenAI collaborates with Oracle to build a 4.5 GW data center, Stargate AI's total computing power breaks 5 GW. OpenAI launches "ChatGPT Agent"! Integrating Operator and Deep Research: competently handling ticketing, food delivery, and writing briefs. OpenAI reportedly plans to launch an AI version of Office software, going head-to-head with Microsoft and Google. "Gambling on OpenAI, Masayoshi Son has turned the tables again"—this article was first published in BlockTempo, the most influential blockchain news media.