Uncanny Valley – Anna Wiener

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.

Rating: 3.5 out of 5.

First off, I just have to say how much I LOVE the cover! It’s eye-catching and fits the subject perfectly…although to clarify just in case, know that this book is not about robots and AI (not directly, anyway), but about Silicon Valley during the growth years.

This was one of my most anticipated reads of early 2020 (can’t believe I posted that in January, seems like a lifetime ago). How’d it stack up? I was maybe a little disappointed by it overall, but it was still an entertaining and informative read.

So, I actually had the chance to go hear Wiener speak about Uncanny Valley before I’d even read it. In person, she’s reserved and definitely an introvert, but surprisingly funny – she has a dry, straight-faced humor that’s so unexpected from someone as mild as her, and it made it even more excited to read the book. The first half of it is pretty amazing. There are so many scenes where you think, “No way that really happened, and in an office setting too”, but yup, those things really happened and now she’s regaling us with all the stories. A lot of the people really live up to the Silicon Valley stereotype too, and they’re all either 1) arrogant as hell off their own recent success, 2) delusional as hell that they’re going to be the next unicorn startup, or 3) awkward as hell because all the geek stereotypes. It’s brash, it’s gossipy in a restrained way, and it’s fun even though you get the sense Wiener wasn’t really treated as part of the “in-crowd” because she was in customer service, not engineering.

In the second half, I think the book tends to fall off and repeat a lot of the material from the first half. It’s notable that Wiener’s training is in journalism and longform writing, which is relevant because that’s exactly how the book reads – like a collection of well-written, elucidating articles instead of a coherent book with an overarching narrative. Some of chapters start to blend together and the stories all sound the same…at some point I remember losing track of the characters and companies (it’s a stylistic choice of hers to omit all names and describe them instead, so for example Allbirds is “the company behind the excessively comfortable woolen shoe beloved by Bay Area venture capitalists”, and you can see how things start to get confusing), then losing track of where she was in her personal development altogether. By the ending, I was admittedly pretty bored.

If I could redo my reading experience, I’d read just that first half and DNF the rest. I still like her writing a lot – her personality and humor come out through it – and want to read whatever she publishes next!

One thought on “Uncanny Valley – Anna Wiener

  1. This is such an elucidating review! I wasn’t sure what to expect in terms of writing style from this book, so thanks for helping me set my expectations. It sounds upsetting that the second half is so unnecessary to the story… ugh. But I’m still very intrigued!!


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