Emil Michael, the Pentagon’s top official overseeing military artificial intelligence policy, has sold his stake in AI-powered search company Perplexity for between $5m and $25m, according to federal financial disclosure records reviewed by the Guardian.
The latest sale follows an earlier disclosure that Michael made substantial gains from his investment in Elon Musk’s artificial intelligence company, xAI.
The Guardian reported earlier this year that Michael sold his xAI investment in January, making a gain estimated at between 400% and 4,800%, with his profits potentially reaching $24m.
His most recent financial disclosures show that Michael sold his Perplexity shares in June. The AI search company has reportedly been seeking a valuation of around $30bn.
The records do not indicate whether Michael made a profit from the Perplexity sale because federal financial disclosures provide broad ranges rather than exact figures. The Lever had reported in March that Michael held an interest in the company.
Michael’s 2025 financial filings also revealed that he received a personal loan from Perplexity in 2024, valued between $250,000 and $500,000 and carrying an interest rate of 4.57%.
He had previously served on Perplexity’s advisory board but disclosed that he left the position after joining the federal government.
Some of Michael’s Perplexity shares had vested, while others remained unvested. Under an ethics agreement, he pledged not to profit from the unvested shares. However, the disclosures do not make clear which portion of the stock he sold.
Perplexity secured a contract with the US government’s General Services Administration in November last year, although the available records do not indicate any specific connection between the company and the Pentagon.
Richard Painter, an ethics expert who previously served as a White House lawyer under former President George W Bush, said Michael should have disposed of his interest in the company before entering government service.
“He should have sold all interest in the company before he started working,” Painter said. “That’s the way we would have done it back when I was working for president.”
A Pentagon spokesperson defended Michael and other defence officials, saying they “are in full compliance with ethics laws and regulations. Any claims otherwise are false”.
The spokesperson also said the department operates “a rigorous, multi-layered ethics framework”.
Painter said owning shares in an AI company would not automatically constitute a legal violation, but argued that it could raise concerns because of how the arrangement might appear to the public.
“Most administrations would have said get out of that stock before you start that job,” he said.
Michael’s investment gains while serving at the Pentagon are not limited to AI companies. His latest disclosure also shows that he made substantial returns from selling an interest in Brex LLC, a privately held financial software company.
According to the records, Michael sold his Brex holdings in April for at least $5m. The company, which is backed by Peter Thiel, was acquired by Capital One that same month. Michael had previously worked as a consultant for Brex.
Because Brex was privately held, there were no publicly available stock prices. However, Michael’s disclosures show that the reported value of his holdings rose considerably during his time in government.
In March 2025, he reported that his Brex stake was worth a maximum of $750,000.
Based on the disclosed figures, Michael’s profit from the Brex sale could have ranged from $4.25m to as much as $24m.
Unlike Musk’s xAI, Brex does not appear to have any reported business dealings with the US government.
Michael has also emerged as a prominent figure in the Pentagon’s dispute with AI company Anthropic.
