Masayoshi Son's Latest Bet on OpenAI Raises Concerns of Overvaluation and Concentration Risk

SoftBank's chairman, Masayoshi Son, is heavily investing in OpenAI, valuing it at $300bn and committing up to $30bn by year-end. This mirrors the WeWork investment pattern, where Son invested late, paid high valuations, and faced a flawed business model. Son's investment in OpenAI raises concerns about concentration risk and potential overpayment. Son's past successes and failures highlight the importance of caution when investing in unicorns with high valuations and uncertain business models.

SoftBank Group Corp.'s chairman, Masayoshi Son, has made a significant investment in OpenAI, valuing the AI company at $300 billion and committing up to $30 billion by the end of the year. This investment mirrors SoftBank's past investment strategy, which saw the company invest heavily in WeWork, a company that faced a flawed business model and high valuations Microsoft, OpenAI Sign Non-Binding Deal To Reshape Partnership As ChatGPT Maker Pushes $500 Billion Valuation^[1].

Under the new terms of the Microsoft-OpenAI partnership, OpenAI is expected to adopt a more conventional corporate structure while ensuring Microsoft retains access to its advanced models. This move could pave the way for OpenAI to restructure as a for-profit entity, aiming for a $500 billion valuation Microsoft, OpenAI Sign Non-Binding Deal To Reshape Partnership As ChatGPT Maker Pushes $500 Billion Valuation^[1].

Son's investment in OpenAI raises concerns about concentration risk and potential overpayment. His past successes and failures, such as the WeWork investment, highlight the importance of caution when investing in unicorns with high valuations and uncertain business models. SoftBank's investment in OpenAI mirrors Son's strategy of investing late in high-growth companies, often at high valuations.

The investment in OpenAI comes amidst a broader trend of increasing investment in AI and FinTech companies in India. In 2025, India added 11 new unicorns, including Ai.tech, valued at $1.5 billion, and major additions in the FinTech sector such as Navi Technologies ($1.7 Bn) and Moneyview ($1.2 Bn) From AI to FinTech: India's Unicorn boom gets 11 new billion-dollar players^[2].

While Son's investment strategy has been successful in the past, the high valuation and uncertain business model of OpenAI present potential risks. Investors must carefully consider these factors when evaluating the potential returns and risks associated with investing in OpenAI and other high-valuation unicorns.