Amanda Rosenberg talks for the first time about the fallout from her tumultuous relationship with Google billionaire Sergey Brin.
As the decade draws to a close, it would be fair to say so does our love affair with Silicon Valley. But if we are more wary than ever of the utopian promises pouring out of San Francisco, perhaps none are more so than the women who have worked there, leading to a slew of female-authored, insider accounts of the tech capital.
Last year, US journalist Emily Chang published Brotopia, about its notoriously male-dominated culture, and in January former tech worker Anna Wiener will release her memoir, Uncanny Valley, of the four years of casual sexism she experienced there.
This week, Amanda Rosenberg, a Marlborough and Leeds University-educated former Google executive, publishes her own memoir, That's Mental: Painfully Funny Things That Drive Me Crazy About Being Mentally Ill, in which she details the psychological breakdown she suffered while working at the tech giant's Californian HQ.
"It was so bleak," she says of her time there. "Because on the outside I was like, 'Look at me winning, succeeding, and being everything my mother wanted me to be,' and inside just dying and confused and scared and alone."
Rosenberg's experience, was, of course, more extreme than most. For what she doesn't mention in the book – and is reluctant to discuss in person except in the most oblique terms – is that her breakdown was precipitated by what she admits was a "toxic" relationship with multi-billionaire Google president Sergey Brin.
At the time, Brin was 40 years old and married to 23andMe CEO, Anne Wojcicki, with two children under six; Rosenberg was 27, suffering from undiagnosed mental illness and thousands of miles away from her friends and family.
"I was completely alone when I had to work my way back from complete mental rubble," she says of the aftermath of the affair. "And I rebuilt my life and I made it what it is today."
Now 33, Rosenberg is self-effacing and slightly awkward when we meet on a balmy winter morning in Los Angeles, where she is staying on business. She seems to hide behind a pair of huge, owl-like glasses and a curtain of hair, but any shyness is punctuated by copious quips.
"Depressed people don't look different," she says with feeling, her British accent betraying only the slightest trans-Atlantic twang. "I am massively depressed... and look at me, I'm f****** beautiful," she deadpans, gesturing to herself, before bursting into peals of laughter.
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In 2012, Rosenberg was a few years out of university and working in the marketing department of Google's central London office when she was offered the opportunity to transfer to the company's headquarters in California – "a big deal" – and quickly rose through the ranks.
Before long, she was appointed the public face of Google Glass, a computerised pair of "smart" spectacles equipped with internet and a camera that the search engine giant believed would revolutionize the wearable tech market.
The role thrust Rosenberg into the uppermost echelons of the tech titans; within a year, she found herself embroiled with Brin, 13 years her senior. When news leaked he had left Wojcicki, to whom he'd been married for six years, Rosenberg found herself at the centre of a media maelstrom.
The combination of sex and tech proved irresistible and the story quickly ignited on both sides of the Atlantic, stoked by tabloids, broadsheets, blogs and glossy magazines alike.
Rosenberg doesn't mention Brin in the book by name but, in the chapter about her first suicide attempt, she describes being in an "intense and tumultuous relationship" during which her self-esteem "was at an all-time low".
Did the public fall-out contribute to her perilous mental state? "Of course it did," she replies. "It wasn't the main thing but it definitely tipped me over the edge. It would tip anyone over the edge.
"I've never talked about it," she adds, hesitantly, picking over her words. "It was incredibly painful. I was... it was incredibly painful. And it wouldn't happen today," she adds.
She is, ostensibly, referring to the media onslaught and array of sexist headlines accusing her of trying to sleep her way to the top, while married Brin walked away with his reputation intact. "It's always the men who are protected," Rosenberg remarks. "It's never the men who get slut-shamed."
But she could just as well be talking about the relationship itself; a fact underscored by McDonald's announcement, just days after Rosenberg and I meet, that its British-born CEO Steve Easterbrook had been fired for engaging in a consensual relationship with an unnamed female colleague.
At the time Rosenberg worked there, Google was infamously hands-off about inter-company relationships, with one unnamed former employee claiming the company was "intentionally agnostic about dating". Over the years, a number of notable workplace romances started in Google's c-suite, including one between Brin's co-founder, Larry Page, and Marissa Mayer, the company's first female engineer and subsequent CEO of Yahoo.
Since the advent of the #MeToo movement, however, the search engine giant has reportedly begun to clamp down on office affairs, particularly between employees in a reporting chain.
Rosenberg left Google not long after the relationship became public ("I wasn't young or stupid, but I was – I was vulnerable"), moving through a few start-ups before leaving tech entirely to focus on writing. Brin, meanwhile, continues to oversee Google and recently welcomed a child with his second wife, Nicole Shanahan, a legal tech entrepreneur, also over a decade younger than him.
Given the way in which our attitude to workplace romances between powerful men and their subordinated has shifted so fundamentally over the last few years, does Rosenberg see the relationship with Brin now through a different lens? She stutters for a few seconds. "I think it wasn't right for many reasons," she concludes. "I never want to talk about it ever again, to be honest, because I've got my own life."
Unusually, Rosenberg maintains she didn't experience any sex discrimination during her time in tech, although she admits: "It is male dominated, I felt, from my experience, specifically within start-ups, the lack of empathy from management, not treating people like human beings." Working through the night, for example, was treated as a badge of honour.
#ThatsMental "is a darkly funny, highly intimate book that feels at home alongside titles like Jenny Lawson’s Furiously Happy or Carrie Fisher’s Wishful Drinking. Which is to say, it’s extremely essential reading."🙏@sarahstiefv @PureWow @AmandaRosenberg https://t.co/kY8dl1VDfW— Keely Platte (@andanotherround) November 18, 2019
She still lives in San Fransisco with her husband, Pavel Vodenski, himself a software engineer who also works at Google (evidence, if needed, of just how incestuous Silicon Valley can be) and their 13-month-old daughter, and is working on screenplays and local fringe comedy shows, as well as a follow-up book on maternal mental health.
Rosenberg had always harboured dreams of being a writer but it seemed "laughable, almost insulting", she says, particularly under the tutelage of a career-driven Chinese mother who worked in banking and a British father with a background in advertising. Part of the reason she wound up in San Francisco was in a misguided attempt to impress her parents, with whom she continues to have a strained relationship.
"A running theme of my life is like, 'Well, my mum will be proud of me if I have a lot of money.' If we all go out to dinner and I pick up the bill – which in Chinese culture is just a huge mess because everyone wants to fight to pay the bill but they don't really want to pay the bill – it feels good to pay for that."
Originally from Hong Kong (her parents wed during their lunch break before going straight back to work), the family soon moved to London, whereupon an eight-year-old Rosenberg was swiftly dispatched to Cottesmore School in West Sussex. It was there, during one of their fortnightly weekend visits, that her parents announced they were separating.
At £38,955-a-year ($78,300) Marlborough College she was in the year above James Middleton. Given his own recent admission to The Telegraph that he has also endured suicidal thoughts, I venture whether living apart from one's parents at such a young age might have something to do with patchy mental health.
"No, I don't think it's something about being at a boarding school," she says, pointing out that all teens, regardless of what school they're at, "want to hide [their] feelings in order to seem popular or at least have friends."
In That's Mental Rosenberg does the complete opposite, sharing intimate details of everything from her first anxiety attack (which took place at Marlborough), to her current list of medication for bipolar II.
The book is by turns heart-breaking (I wept over a passage in which Rosenberg recounts her younger brother's funeral) and hilarious, liberally peppered with pop culture references, sex jokes and swear words, despite its sombre subject matter.
"I never set out for it to be a funny book," Rosenberg says. "I wanted to write a book for the Amanda who needed it back then. At those dark moments [when] you feel like you have no choice and you feel so hopeless. And sadly, that's something I think is actually quite universal."