The top Pentagon official overseeing military artificial intelligence policy, who reaped profits earlier this year of up to $24m selling his private investment in Elon Musk’s AI company, has now sold his holdings in another AI company for between $5m and $25m, according to records seen by the Guardian. (Federal financial records show ranges of dollar values rather than specific figures.)
Earlier this year, the Guardian disclosed that the official, Emil Michael, had profited handsomely from his investment in Musk’s xAI in January, with a gain of between 400% and 4,800%.
Michael’s latest financial disclosures show that in June, he sold off his shares in Perplexity, an AI-powered search engine. Recent reports have said Perplexity is looking for a financial valuation of $30bn.
The records don’t reveal whether he made a profit on the sale because of the large dollar range listed in his disclosures. The Lever reported in March that Michael had the holdings in Perplexity.
His financial disclosure filings from 2025 also show that he had received a personal loan from Perplexity a year earlier, of between $250,000 and $500,000, at an interest rate of 4.57%. He also joined a Perplexity advisory board, but his disclosures said he stepped down upon entering federal service.
Some of his Perplexity stock was vested and some was unvested, and in his ethics agreement he pledged not to make a profit off the unvested stock. It is not clear from the disclosures what stock he sold.
Perplexity announced a contract with the US government’s General Services Administration in November of last year, though records do not show specific ties to the Pentagon.
“He should have sold all interest in the company before he started working,” said ethics expert Richard Painter, a former lawyer at the White House under George W Bush. “That’s the way we would have done it back when I was working for president.”
A Pentagon spokesperson said Michael and other defense officials “are in full compliance with ethics laws and regulations. Any claims otherwise are false”. The spokesperson said the department has “a rigorous, multi-layered ethics framework”.
Painter said Michael’s ownership in an AI company would not be a violation of law but would have raised questions because of appearances. “Most administrations would have said get out of that stock before you start that job.”
Michael’s lucrative trading while at the Pentagon isn’t limited to AI companies. His latest disclosure also shows he has now realized gains at least 473% selling holdings he owned in a separate non-public company.
According to the records, Michael sold holdings in Brex LLC in April for at least $5m. Brex, a financial software company, is backed by Peter Thiel and was acquired by Capitol One that month. Michael had been a consultant at the firm.
Though the firm was privately held and stock prices were not available, Michael’s holdings jumped during his time in government: he reported in March 2025 that his Brex holdings were worth just a maximum of $750,000.
Michael’s profit in the Brex sale could have been as large as $24m or as little as $4.25m.
Brex, unlike Musk’s xAI, does not appear to do any reported work with the US government.
Michael was the face of the department’s war against AI company Anthropic.
He is a frequent guest on podcasts, including on the tech podcast called Sourcery – and the episode on which he appeared in December, was sponsored by Brex, while Michael was still an investor in the company. It was called “Misunderstood Power: Emil Michael on the Truth about DOW and Defense Tech.”
Emil was chief business officer at Uber from 2014 to 2017. BuzzFeedNews reported in 2014 that Michael had privately floated digging up dirt on critical journalists, though Michael said the comment, at what he thought was an off-the-record dinner, didn’t reflect his views.
