The Pentagon's top official overseeing military artificial intelligence policy has sold his holdings in AI search company Perplexity for between $5m and $25m, according to federal financial disclosures seen by the Guardian. The sale comes months after Emil Michael reaped up to $24m in profits from his private investment in Elon Musk's xAI, raising fresh questions about the intersection of personal financial interests and public AI policy.
Federal records disclose dollar ranges rather than exact figures. Michael's latest filings show he sold Perplexity shares in June. Perplexity has reportedly been seeking a valuation of $30bn. The records do not reveal whether Michael profited on the sale because of the wide dollar range listed.
A pattern of lucrative private holdings
Earlier this year, the Guardian reported that Michael's January sale of xAI stock produced a gain of between 400% and 4,800%. His 2025 disclosures also show a personal loan from Perplexity of between $250,000 and $500,000 at a 4.57% interest rate, taken out a year earlier. Michael had joined a Perplexity advisory board but said he stepped down upon entering federal service.
Some of his Perplexity stock was vested and some was unvested. In his ethics agreement, Michael pledged not to profit from the unvested stock. The disclosures do not specify which shares he sold.
Michael's trading activity extends beyond AI companies. His latest disclosure shows he realized gains of at least 473% selling holdings in Brex LLC, a financial software company backed by Peter Thiel, in April for at least $5m. Brex was acquired by Capital One that month. Michael had been a consultant at the firm. In March 2025, he reported his Brex holdings were worth a maximum of $750,000. The profit on the sale could have been as little as $4.25m or as large as $24m.
Ethics experts question the optics
"He should have sold all interest in the company before he started working," said Richard Painter, a former White House lawyer under George W. Bush. "That's the way we would have done it back when I was working for president."
Painter said Michael's ownership in an AI company would not violate the law but would raise questions because of appearances. "Most administrations would have said get out of that stock before you start that job," he said. A Pentagon spokesperson said Michael and other defense officials "are in full compliance with ethics laws and regulations. Any claims otherwise are false," adding that the department has "a rigorous, multi-layered ethics framework."
Perplexity announced a contract with the General Services Administration in November of last year. Records do not show specific ties to the Pentagon. Brex does not appear to do any reported work with the US government.
Public role, private interests
Michael has been the public face of the department's position against AI company Anthropic. He is a frequent podcast guest, including on the tech podcast Sourcery. The December episode he appeared on was sponsored by Brex while Michael was still an investor in the company.
Michael served as chief business officer at Uber from 2014 to 2017. In 2014, BuzzFeed News reported that Michael had privately floated digging up dirt on critical journalists. Michael said the comment, made at what he thought was an off-the-record dinner, did not reflect his views.
For professionals working at the intersection of AI for Government and private sector investment, Michael's disclosures highlight the compliance questions that arise when officials retain financial stakes in companies adjacent to their policy portfolios. The situation also underscores why AI for Executives & Strategy training increasingly covers ethics and disclosure frameworks alongside technical topics.
Why this matters for government and strategy professionals
The Michael disclosures show what happens when personal investment portfolios overlap with public policy authority, even when no law is broken. For executives and government leaders, the practical takeaway is straightforward: divest before taking office, or expect scrutiny. Ethics agreements that allow partial divestiture or deferred sales leave room for questions about which shares were sold, when, and at what profit. The dollar ranges in federal disclosures make it impossible for the public to know whether a sale produced a windfall. That opacity, not the trading itself, is what fuels the appearance problem.
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