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Situational Awareness explored private asset sales before striking Citadel portfolio deal

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AI-focused hedge fund Situational Awareness explored selling stakes in privately held technology companies before agreeing to transfer most of its public equity portfolio to Citadel, according to a report by Bloomberg.

The firm, founded by former OpenAI researcher Leopold Aschenbrenner, approached venture capital investors including Sequoia Capital and Greenoaks about acquiring some of its private holdings as it sought to raise liquidity amid mounting pressure from margin calls.

Those discussions ultimately did not result in a transaction after the hedge fund reached an agreement with Citadel to dispose of the majority of its listed equity portfolio, providing an alternative source of liquidity.

Anthropic was among the assets reportedly considered during the liquidity discussions, although no sale was completed. Sequoia Capital and Greenoaks, both existing investors in Anthropic, were approached because of their familiarity with the company and broader AI investment landscape.

Earlier this week, Citadel agreed to acquire the bulk of Situational Awareness’ public equity portfolio, including positions financed through leverage provided by prime brokers. The transaction enabled the fund to avoid selling its private investments, allowing it to retain ownership of strategic AI assets while significantly reducing its exposure to listed equities.

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