Hustler Words – Emil Michael, now a prominent technology official within the Department of Defense, has resurfaced in the public eye, not only to articulate the Pentagon’s contentious stance against AI powerhouse Anthropic but also to air long-held grievances regarding his tumultuous departure from Uber. In a recent podcast interview, Michael offered an unvarnished look into his strategic thinking on national security tech and, perhaps more strikingly, a raw recounting of the events that led to his and Travis Kalanick’s ouster from the ride-sharing giant, declaring he would "never forget, nor forgive" the investors responsible.
The revealing conversation, conducted by Joubin Mirzadegan of Kleiner Perkins, took place last month, predating the full public escalation of the DoD’s dispute with Anthropic. However, it was Michael’s candid reflections on his 2017 exit from Uber that immediately captured attention. When directly questioned about whether he was effectively forced out alongside Kalanick, Michael’s concise reply was "Effectively." His resignation preceded Kalanick’s by eight days, a consequence of a sweeping workplace investigation into allegations of sexual harassment and gender discrimination. While Michael was not personally implicated in the allegations, the inquiry, led by former U.S. Attorney General Eric Holder, recommended his removal. Kalanick’s subsequent departure was widely characterized as a shareholder revolt, spearheaded by influential investors like Benchmark.
Michael’s enduring resentment stems from a profound conviction shared with Kalanick: that autonomous driving was the pivotal future of Uber, a vision they believe was prematurely curtailed by investors prioritizing immediate financial returns over long-term, transformative growth. "They wanted to preserve their embedded gains, rather than try to make this a trillion-dollar company," Michael asserted during the interview. Kalanick has echoed this sentiment, lamenting at last year’s Abundance Summit that Uber’s self-driving program was second only to Waymo at the time of its cancellation, rapidly closing the gap.
Indeed, Uber’s self-driving unit was offloaded to Aurora in a transaction widely perceived as a fire sale in 2020, three years after Michael and Kalanick’s exits. While the decision might have seemed pragmatic then, given the heavy cash burn and the nascent state of autonomous tech, Waymo’s current expansion of robotaxi services across ten U.S. cities casts a long shadow, raising questions about what Uber might have achieved had it maintained its ambitious course.
Meanwhile, Kalanick has continued his entrepreneurial journey, recently unveiling Atoms, a robotics company developed in stealth since his Uber departure. He also disclosed his significant investment in Pronto, an autonomous vehicle startup focused on industrial applications, founded by former Uber colleague Anthony Levandowski, with Kalanick reportedly on the cusp of acquiring it outright.
For Michael, the focus has shifted to a new, high-stakes arena: the Department of Defense’s engagement with cutting-edge AI. As a senior technology official, he finds himself embroiled in a critical standoff with Anthropic, one of the few large language model vendors approved for the department, partly through its collaborations with Palantir. Michael highlighted the labyrinthine regulatory landscape governing the DoD, stating, "we almost choke on them." His core contention with Anthropic is the company’s perceived attempt to layer its own policy preferences atop this existing framework. He drew an analogy: "If you buy the Microsoft Office Suite, they don’t tell you what you could write in a Word document, or what email you can send."
Michael further amplified his concerns by referencing Anthropic’s own published findings on "distillation," a technique where Chinese technology companies could effectively reverse-engineer and replicate the model’s capabilities. He argued that under China’s civil-military fusion laws, this could grant the People’s Liberation Army access to a fully capable Anthropic-equivalent model, while the DoD would be restricted by Anthropic’s self-imposed guidelines. "I’d be one-armed, tied behind my back against an Anthropic model that’s fully capable – by an adversary," Michael declared, labeling the scenario "totally Orwellian." He concluded this point with a poignant question: "If you’re an American champion – and I believe they are, they’re one of the most important companies in the country – don’t you want to help your Department of War succeed with the best tools available?"
The dispute has since moved from the negotiating table to the courtroom. Defense Secretary Pete Hegseth officially designated Anthropic a "supply-chain risk" in late February. The government subsequently escalated the conflict last week, filing a 40-page brief in the U.S. District Court for the Northern District of California. The brief contends that integrating Anthropic’s technology into the DoD’s war-fighting infrastructure poses "unacceptable risk," citing the theoretical possibility of the company disabling or altering its technology to serve its own interests rather than national security during wartime.
Anthropic swiftly countered on Friday, submitting sworn declarations and a brief asserting that the government’s case is built on technical misunderstandings and claims never raised during months of prior negotiations. Thiyagu Ramasamy, Anthropic’s head of public sector, specifically challenged the government’s assertion that the company could interfere with military operations by altering its technology’s behavior, stating such an action is not technically feasible. A pivotal hearing in this high-stakes legal battle is scheduled for Tuesday in San Francisco, promising further insights into the complex intersection of national security, cutting-edge AI, and corporate autonomy.
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