The top Pentagon official overseeing military artificial intelligence policy, Emil Michael, has sold his shares in Perplexity, an AI-powered search engine, for an amount between $5 million and $25 million, according to recent federal financial records. Earlier this year, Michael made a profit of up to $24 million from selling his private investment in Elon Musk’s AI company, xAI, with gains ranging between 400% and 4,800%. These transactions have raised questions about potential conflicts of interest, especially as Michael plays a key role in shaping U.S. military AI policy. According to 2025 financial disclosures, Michael had taken out a personal loan of between $250,000 and $500,000 from Perplexity at an interest rate of 4.57% a year earlier. He also served on Perplexity’s advisory board but resigned when he joined the federal government. Some of his shares in Perplexity were vested (meaning he owned them outright), while others were unvested (subject to certain conditions before ownership was fully realized). In his ethics agreement, Michael pledged not to profit from the unvested stock. However, it remains unclear exactly which shares he sold. Perplexity signed a contract with the U.S. government’s General Services Administration in November of last year, though there is no clear connection between the company and the Pentagon in official records. Ethics expert Richard Painter, a former White House lawyer, has stated that Michael should have sold all his interests in Perplexity before beginning his federal role. A Pentagon spokesperson defended Michael, stating that he and other defense officials are fully compliant with ethics laws and that claims of violations are false. The spokesperson emphasized that the department has a “rigorous, multi-layered ethics framework.” Michael’s financial dealings while in the Pentagon are not limited to AI-related companies. His latest disclosures show he made gains of at least 473% from selling shares in Brex LLC in April, earning at least $5 million. Brex, a financial software company backed by billionaire Peter Thiel, was acquired by Capitol One that month. Michael had previously worked as a consultant for the firm. While his Brex holdings were worth up to $750,000 in March 2025, the profit from the sale could have been as high as $24 million or as low as $4.25 million. Unlike xAI, Brex does not appear to have any reported government contracts or ties to defense work. Michael has been a prominent figure in the Pentagon’s efforts against AI company Anthropic, often speaking publicly about the risks of unregulated AI development. He has also appeared on various tech podcasts, including one sponsored by Brex while he was still an investor in the company. Michael previously served as Uber’s chief business officer from 2014 to 2017. In 2014, BuzzFeedNews reported that Michael had suggested privately digging up dirt on critical journalists, though he later claimed the remark was made in a private, off-the-record conversation and did not reflect his views.