In her mid-twenties, at the height of tech industry idealism, Anna Wiener -- stuck, broke, and looking for meaning in her work, like any good millennial -- left a job in book publishing for the promise of the new digital economy. She moved from New York to San Francisco, where she landed at a big-data startup in the heart of the Silicon Valley bubble: a world of surreal extravagance, dubious success, and fresh-faced entrepreneurs hell-bent on domination, glory, and, of course, progress. Anna arrived amidst a massive cultural shift, as the tech industry rapidly transformed into a locus of wealth and power rivaling Wall Street. But amid the company ski vacations and in-office speakeasies, boyish camaraderie and ride-or-die corporate fealty, a new Silicon Valley began to emerge: one in far over its head, one that enriched itself at the expense of the idyllic future it claimed to be building. Part coming-age-story, part portrait of an already-bygone era, Anna Wiener's memoir is a rare first-person glimpse into high-flying, reckless startup culture at a time of unchecked ambition, unregulated surveillance, wild fortune, and accelerating political power. With wit, candor, and heart, Anna deftly charts the tech industry's shift from self-appointed world savior to democracy-endangering liability, alongside a personal narrative of aspiration, ambivalence, and disillusionment. Unsparing and incisive, Uncanny Valley is a cautionary tale, and a revelatory interrogation of a world reckoning with consequences its unwitting designers are only beginning to understand.