Vinod Khosla says Khosla Ventures deliberately declined to invest in Anthropic to preserve the information and strategic advantage provided by its close relationship with OpenAI. In his view, in such a fast-moving sector, understanding the technology’s direction is worth more than diversifying the portfolio. His firm invested $50 million in OpenAI’s first venture funding round in late 2018 or early 2019, at a $1 billion valuation, securing roughly a 5% stake. Khosla describes that investment, his largest first cheque, as twice the size of any initial investment he had made before. His decision comes ahead of Anthropic’s upcoming IPO, even though about 40% of OpenAI’s backers also hold stakes in Anthropic.
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