The last time a short story truly resonated with me, I was 25 but looked and felt older, gray around the temples from endless hours at my latest Flatiron District startup gig gone belly-up for, evidently, not disrupting enough. It was a sleepless night spent trawling Project Management and Client Success postings, roles conceived to oversee timelines and partnerships related to products which may or may not have existed in any tangible form. Propped on a Casper bed (lumpier than it looked online) and squinting through Warby Parker frames (heavier than they looked online) into an on-its-last-legs iPhone 4, I came across Anna Wiener’s “Uncanny Valley,” published in n+1.
Capturing the numbing experience of a client-facing non-engineer riding out Northern California’s latest tech bubble, Wiener’s lightly fictionalized story honed in on the vagaries of volatile investors, slimy salespeople, office tchotchkes, bubbly faux-morale, and IPO pipe dreams that briefly set Silicon Valley ablaze. Presaging by a year the memos which illuminated stunning institutional misogyny at Uber and Google, “Uncanny Valley” found acclaim for its portrayal of startup culture’s questionable hiring practices and casual sexism, earning Wiener both a book and movie deal.
Yet as 2018 finds Silicon Valley’s most ubiquitous companies and public figures embroiled in scandal after scandal, the glacial pace of book publishing — in contrast to tech’s governing philosophy of “move fast and break things” — has stranded the Big Five flatfooted. This spring’s most hotly anticipated San Francisco-based tech titles paint an improbably rosy picture of a city and industry under fire.
Sooner or later, tech literature will need to confront a truth many of us already have — that “disruption” isn’t necessarily synonymous with progress.
Anna Yen’s debut novel Sophia of Silicon Valley, out April 10 from William Morrow, is a roman à clef based on the author’s years working under Steve Jobs at Pixar and Elon Musk at Tesla. Dating back to last fall, it’s appeared on most-anticipated lists from Elite Daily, Cosmopolitan, and Popsugar. Like Doree Shafrir’s Startup from last spring, it follows a driven young woman as she navigates the foibles and follies of boys’ club startups. But where Shafrir’s incisive writing tended toward critical satire, Yen’s makes for hagiographic tech gospel.
After her rash insubordination torpedoes an investment banking job teed up by her well-connected father, Sophia Young — a wealthy Taiwanese-American college grad equal parts Elle Woods of Legally Blonde and Andrea Sachs of The Devil Wears Prada — is gift-wrapped another job at a Bay Area firm specializing in IPOs. There, her pluck proves an asset in the high-octane dot-com atmosphere until she’s lured away by a thinly veiled Steve Jobs (here named Scott Kraft), to head investor relations at Treehouse, the book’s version of Pixar.
Anyone who’s seen either of the Hollywood Steve Jobs biopics — the one where Ashton Kutcher and Josh Gad revolutionize personal computing, or the one where Michael Fassbender and Seth Rogen yap Aaron Sorkin dialogue at each other — will recognize the personal idiosyncrasies of Jobs/Kraft, but the gold-hearted brilliance conveyed by Yen borders on unconflicted hero worship. “That inner god or genius or whatever the hell it is has emerged,” Sophia narrates as her boss preps for a speaking gig. “He will mesmerize you.” Encouraged by the deeply paternal Kraft to avoid career stagnation at all costs, she eventually jumps ship to Ion, whose Palo Alto HQ plans to bring solar-powered cars to market (in case it wasn’t obvious, Yen is now writing about Tesla).
If Yen’s book aims to show how women in tech can’t have it all, then she falls short, instead landing somewhere in the realm of career narrative wish-fulfillment. Armed with the safety net of having millionaire parents, her rapid rise from IPO to IPO is spurred by the unflagging support of the purportedly difficult men to whom she reports. “He seemed too good to be real,” Sophia says of Kraft’s right-hand man Jonathan when he suggests meditation during a stock market drop. “How beautiful and generous a gesture this was,” she gushes when Andre Stark, the Musk character, dedicates a park bench to the victims of the Tesla plane crash. “Qualities of a great leader.” At Yen’s hand Jobs, Musk, and their cohort are uncomplicated Men of Vision, benevolent overlords bent on changing the world and ensuring that Sophia always fly first class and stay in the fanciest hotels.
Given Jobs’ and Musk’s larger-than-life statures and infamous neuroses, one would expect a fictionalized portrayal of them to read fairly tongue-in-cheek — according to Walter Isaacson’s biography, Jobs would soak his feet in toilet bowls to relieve stress; Musk’s determination to prove that he is a normal person who likes normal things has culminated in him trying and failing to buy The Onion, poaching its staffers and starting a company called Thud! (and getting royally owned by The Onion in the process). But in Sophia of Silicon Valley, the consumer tech oligarchs are slightly overcaffeinated Greek deities. The implications of their power and whether anyone ought to wield it is left basically unconsidered. “I’ve been trained since birth to get what I want; now I use this ‘skill’ to get my bosses whatever they want,” Sophia declares as she looks back at her meteoric ascent through Silicon Valley. That getting what she wants might further the nefarious business fantasies of sociopaths remains unexamined.
For Sophia, Silicon Valley is a land of opportunity where, despite institutional obstacles, she’s able to buck societal expectations and is rewarded for aggressive ambition. But Yen’s me-first doctrine masquerading as self-reliance manifesto doesn’t offer sufficient evidence for such a world: Sophia lands jobs through personal connections and the generosity of her superiors, often-ominous technocrats written like Disney characters. When critical, Yen is critical of individuals rather than companies, industries, or capitalism writ large, offering little analysis or condemnation of the racial and gender discrimination she observes. If her Silicon Valley has a fatal flaw, it’s not cutthroat VCs placing profit above compassion or the tech industry’s erosion of labor rights, privacy, of free and civil discourse — it’s that it’s piloted by charmingly maladapted nerds.
When Dave Eggers penned his 2013 novel The Circle, he claimed to have done minimal research in formulating his cynical tech industry forecasts — but even so, that didn’t stop him from being at least a little on the money when depicting a dystopia in which we broadcast our every action online. His latest, The Monk of Mokha, is a reported non-fiction book which, perplexingly, arrives at a far more optimistic diagnosis. The Man of Vision is Mokhtar Alkhanshali, a Yemeni-American entrepreneur who chases his dream of a coffee importing empire through the Arab Spring. That Mokhtar has little knowledge of the industry or passion for coffee itself is ultimately inconsequential; Eggers presents his dogged motivation as a result of divine inspiration. “Mokhtar referred to it as a mission in those early days, and he was careful not to say that he was being guided by God,” he writes. “But he believed this.”
Mokhtar pays established Bay Area coffee moguls at Blue Bottle and Boot Coffee for apprenticeships and access. Over numerous trips to Yemen he’s introduced to farmers and importers, identifying ways to streamline production and mark up prices overseas. But it isn’t until he presents his messy proposal to a mentor, a San Francisco neighbor who struck gold with an e-commerce startup, that doors begin to open. Tellingly, Mokhtar’s company has a name and logo long before a product or business plan.
After he’s secured initial funding from friends in the tech world — men made rich by Intuit and NetSuite, drawn by Mokhtar’s scatterbrained moxie — he returns to Yemen to secure his first batch just as the country is falling into civil war. Abandoned by the U.S. State Department after he avoids their warnings to evacuate, Mokhtar is forced to flee Saudi bombers in Sana’a, dodging local militias, Houthi insurgents, and corrupt police before finally escaping to Djibouti in a pontoon boat.
Returning to the States with his improbable escape narrative, Mokhtar receives a celebrity’s welcome and the investors, of course, line up. Founders Fund, Peter Thiel’s firm which backed Facebook, Airbnb, and Lyft, makes a godfather offer. After briefly hesitating over Thiel’s hyper-conservative advocacy (“Then again, Thiel was gay, too. It was all very confusing,” is all Eggers has to say about Thiel’s legendarily questionable politics), Mokhtar accepts Founders’ lead investment.
Eggers paints Mokhtar’s tale as a parable of self-improvement, proof how Silicon Valley exceptionalism inspires global good. “It’s chiefly about the American Dream, which is very much alive and very much under threat,” he writes in the prologue. But to make a Horatio Alger hero of Mokhtar for pursuing his dream through life-threatening circumstances is a bit of a stretch; at one point Mokhtar’s work with Yemeni farmers is likened to Cesar Chavez and Dolores Huerta’s labor agitation..
The Monk of Mokha preaches a distinctly Silicon Valley dogma of personal wealth, one which seems a short stone’s throw from the pro-business, small government precepts advanced by Eggers’s older brother William. “It was difficult sometimes to see all this as essential,” Dave acknowledges in The Monk of Mokha. “People were dying in Yemen. The country was collapsing, and in his San Francisco high-rise, Mokhtar was waking up every morning at 4:00 a.m. to call Sana’a about coffee.” And like Yen’s Sophia, Mokhtar achieves this American Dream by knowing the right people, marketing himself, and maintaining the good graces of investors. That Mokhtar heedlessly puts himself in the path of a bloody Middle Eastern war is, in Eggers’s estimation, the best imaginable P.R. for his fledgling startup.
If Yen and Eggers’s books are the literary equivalent of senseless Oleg Vishnepolsky LinkedIn posts and vapid Gary Vaynerchuk motivational videos, it reasonably begs the question: Why are the major publishing houses producing Elon Musk fanfic and Dave Eggars reportage celebrating light war profiteering? The canonical Wall Street lit of the ‘80s and ‘90s — non-fiction books like Liar’s Poker, Den of Thieves, and The Predator’s Ball; novels like JR and American Psycho — detailed the lurid excess of American finance, how an industry cratered the economy and propagated a culture of craven dishonesty. With platforms selling our personal information and burning through funding secured in poor faith, where is tech’s Bonfire of the Vanities?
With luck, Wiener’s forthcoming projects will employ Wolfe’s winning strategies: leverage of embeds and a deeply-sourced whisper network, both of which have propelled HBO’s Silicon Valley to uproarious heights. Ryan Holiday’s Conspiracy, published in February, took an insider’s track to report on Thiel and Nick Denton’s intersection of ego, tech, and New York City publishing, hanging Thiel by his own words despite his and the author’s mutual enemy in Gawker Media. (Note to all anti-Fourth Estate, Gamergate-bandwagoning libertarian VCs out there: if a famously manipulative writer is flattering you, it’s probably a red flag.)
But for now, books such as The Circle and Franklin Foer’s World Without Mind must critique Silicon Valley from the outside, while only the chosen few who’ve survived and thrived within Big Tech become the authors and subjects of books that, inevitably, build upon their industry’s self-suckitude. The experiences of uniquely successful startup mavens and ideators are uncritically presented as representative, ignoring the legions of underemployed programmers, overvalued unicorn flameouts, and laid-off, mistreated workers silenced by N.D.A.’s scattered across Sand Hill Road. These books make for free market folk tales, blind to the greater implications of unregulated tech dollars.
These are the myths Silicon Valley tells about itself: that riches and fulfillment await anyone bold enough to pursue them; that passion outweighs ideas and innovation; that Clif bars, Nerf guns, and vague promises of equity are legitimate stand-ins for benefits and job security; that systemic racism and sexism are small prices to pay for corporate freedom. Sooner or later, tech literature will need to confront a truth many of us already have — that “disruption” isn’t necessarily synonymous with progress.