Book Review: Uncanny Valley by Anna Wiener

At some point while reading Uncanny Valley, Anna Wiener’s memoir of the early-2010s San Francisco tech scene, I hit a passage where she treats truly autonomous vehicles as a far-off improbability. I looked up from the page just as a Waymo (empty driver’s seat, serene as a monk) rolled past my window. San Francisco has comedic timing.

The book: Wiener leaves the New York publishing world in her mid-twenties for San Francisco startups, and documents the money, the men, the optimism, and the low-grade surrealism of that era from the inside. It came out in 2020. I read it in 2025, as an SF resident, which turned out to be its own experiment.

What I Loved About Uncanny Valley by Anna Wiener

The observational writing is the draw. Wiener has a great eye for a very specific subsection of humanity — the ambient ambition, the Patagonia vests, the all-hands optimism — and the sentences are frequently excellent. As a portrait of a particular San Francisco moment, the first half is sharp enough to leave marks. Living here now, I kept recognizing the bones of the city underneath her version of it.

What I Didn’t Love About Uncanny Valley

Two things. First, it loses steam: the second half sputters where the first half crackles, and the book ends more than it lands. Second, the shelf-life problem, which is bigger than this one book. Tech memoirs age in dog years, and this one wasn’t set far enough in the past to read as history — its wrong guesses (see: the Waymo moment) feel less like period charm and more like a newspaper left out in the rain. Set it thirty years back and the datedness becomes texture. At ten, it’s just… dated.

Final Thoughts on Uncanny Valley

Worth reading for the observations and the sentences, especially if you have any relationship with San Francisco. Just know the energy dips after the midpoint. For the darker end of tech nonfiction, Bad Blood is still the one I’d hand you first, and my Scammer review covers a memoir with the exact opposite problem set.

My final score: 3 out of 5 stars ⭐️⭐️⭐️

Do I recommend this book? 👍 Yes — as a time capsule of a very specific San Francisco, best enjoyed within walking distance of it.

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