Emil Michael, the top Pentagon official overseeing military artificial intelligence policy, sold his holdings in the AI company Perplexity for between $5 million and $25 million in June, according to federal financial disclosures seen by the Guardian. The sale follows his earlier profit of up to $24 million from selling shares in Elon Musk's xAI in January, raising fresh questions about potential conflicts of interest.
Details of the Stock Sale
The financial disclosures, which list dollar value ranges rather than exact figures, show that Michael sold his shares in Perplexity, an AI-powered search engine, in June. Recent reports have indicated that Perplexity is seeking a financial valuation of $30 billion. The records do not specify whether Michael made a profit on the sale, due to the wide dollar range reported, but The Lever reported in March that Michael held the Perplexity stock.
Michael's 2025 disclosures also reveal that he received a personal loan from Perplexity a year earlier, ranging between $250,000 and $500,000, at an interest rate of 4.57%. He also joined a Perplexity advisory board but stepped down upon entering federal service, according to his disclosures. Some of his Perplexity stock was vested, while some was unvested, and his ethics agreement pledged not to profit from the unvested shares. The disclosures do not clarify which portion was sold.
Ethics Concerns and Compliance
Perplexity announced a contract with the US government's General Services Administration in November last year, though records do not show specific ties to the Pentagon. Ethics expert Richard Painter, a former White House lawyer under George W. Bush, said, "He should have sold all interest in the company before he started working. That's the way we would have done it back when I was working for president."
A Pentagon spokesperson countered, saying Michael and other defense officials "are in full compliance with ethics laws and regulations. Any claims otherwise are false." The spokesperson added that the department has "a rigorous, multi-layered ethics framework." Painter noted that Michael's ownership in an AI company would not violate the law but would raise questions due to appearances, saying, "Most administrations would have said get out of that stock before you start that job."
Other Lucrative Trades
Michael's trading activity while at the Pentagon extends beyond AI firms. His latest disclosure shows he realized gains of at least 473% from selling holdings in Brex LLC in April for at least $5 million. Brex, a financial software company backed by Peter Thiel, was acquired by Capital One that month. Michael had been a consultant at the firm, and his holdings had jumped during his time in government, from a maximum value of $750,000 reported in March 2025 to a possible profit of as much as $24 million or as little as $4.25 million from the sale.
Unlike xAI, Brex does not appear to do reported work with the US government. Michael, who was chief business officer at Uber from 2014 to 2017, has also been the face of the department's stance against AI company Anthropic. He is a frequent podcast guest, including on the tech podcast Sourcery; an episode featuring him in December was sponsored by Brex while he was still an investor. BuzzFeedNews reported in 2014 that Michael had privately floated digging up dirt on critical journalists, though he said the comment, made at what he thought was an off-the-record dinner, did not reflect his views.
