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FollowingEmil Michael, Pentagon Deputy Secretary of Research and Engineering and Chief Technology Officer, sold his stake in Perplexity AI in June for a transaction value of between $5 million and $25 million. Michael, who previously served on Perplexity's advisory board, left in early 2025 and later joined the Donald Trump administration in May of the same year.
This is not the first time Michael has withdrawn from investment this year. He also holds shares in Elon Musk's xAI, with a declared value of US$500,000 to US$1 million when he joined the government. According to financial disclosures, he sold the shares on January 9, cashing in between US$5 million and US$25 million, with a maximum gain of 4800%. For a man who has gone from ride-sharing executive to defense official, this is undoubtedly a considerable reward.
The timing of the deal was ironic: the Office of Government Ethics issued him a divestiture certificate for xAI's shareholding on December 18. Four days later, the Pentagon signed a new agreement to deploy a Grok model of xAI on its confidential network. Michael did not actually complete the sale until January 9.
According to Michael's 2025 financial disclosure, before joining the government, he obtained a personal loan of US$250,000 to US$500,000 from Perplexity at an interest rate of 4.57%. In his ethics agreement, he promised not to profit from unvested Perplexity shares-but the disclosure did not say whether the shares sold in June had been vested, or partially vested.
The disclosures come as Michael has been presenting a public image this year as the Pentagon confronts Anthropic. Anthropic is the developer of the Claude model and competes directly with Perplexity and xAI for government contracts. Trump ordered federal agencies to stop using Anthropic's technology on February 27, days later the Pentagon officially classified the company as a "supply chain risk" and banned military contractors from doing business with it.
U.S. District Judge Rita Lin ruled last week that the blacklist illegally retaliated against Anthropic for refusing to allow the model to be used for mass surveillance and autonomous lethal operations. The judge revoked the finding and issued a permanent injunction. At this time, OpenAI had taken over the Pentagon contract that originally belonged to Anthropic, and the Department of Defense had signed confidential network agreements with seven other AI companies, including xAI.
Ethics experts are dissatisfied with this timeline. Former White House ethics lawyer Richard Painter said Michael "should have sold all company interests before starting work." A Pentagon spokesman countered that Michael and other defense officials "fully comply with ethics codes" and noted that the department has a multi-layered ethics review process.
Meanwhile, Perplexity is negotiating a new round of financing with Nvidia that will value the company more than US$30 billion, more than 50% higher than the September 2025 valuation of US$20 billion.
