Portraits of empty ambition built on fraud and privilege

  • The two series feature real-life protagonists who proved the superficiality of the girlboss tag by turning it on its head. Anna Delvey and Elizabeth Holmes desired the success that came with the term, without the hustle associated with it.


    Many commentators have sounded the death knell of the phenomenon known as the girlboss — once considered an embodiment of the future of equality in corporate workspaces and capitalist contexts, now recognised for its limitations.


    This came from the widespread acknowledgment that the mere presence of a female leader does not translate to empowerment, and that consumerism and financial success should not be framed as indicators of goodness. Not everyone had the same 24 hours, and hard work alone was not a determinant of success in the face of systemic inequality.


    Girlbosses could not change the world as we knew it, and they certainly could not prevent gatekeeping and gaslighting from occurring. In their pursuit for power and money, they did not necessarily lift up those around them.


    Aside from cultural commentators, there were two other people who had proved the superficiality of the girlboss by turning it on its head — Anna Delvey and Elizabeth Holmes, who desired the success that came with the term, without the hustle associated with it.


    For a couple of years, Anna Delvey had New York elites fooled into thinking she was a German heiress, until a viral article revealed that she was in fact an ordinary Russian immigrant with no trust fund. Inventing Anna, a Netflix series which is centered on Delvey’s downfall and court case, details how she went about her many crimes: stealing a private jet, making fraudulent loan applications for amounts ranging up to $22 million, never paying for extensive hotel stays, making extravagant purchases on others’ credit cards without their consent. Much of these crimes were committed in an attempt to build the Anna Delvey Foundation — a proposed exclusive club for members and an arts foundation.


    Before it documents Delvey’s unraveling, Inventing Anna paints a picture of how and why she managed to convince high society about her trust fund and status as an heiress. She has a refined taste in art, a sophisticated and intuitive sense about luxury, and demands VIP treatment everywhere. She tips in $100 bills, and seems unfazed in the company of millionaires. She knows the right people in the right places, and in the odd case that she does not, she makes sure someone will introduce her to them. Delvey had all the trappings of a social media influencer but moved with a manufactured sense of je ne sais quois, which prompted one of the characters in the series to exclaim, "She’s almost royalty."


    Delvey could only convince entrepreneurs, philanthropists, investors, and Wall Street giants to believe in her and her brand because of the mythology she created of herself. To them, she was a trust fund-strapped German expat with ideas that could multiply their own wealth.


    A self-assigned mythology is also crucial to Elizabeth Holmes’ ascent from Stanford dropout to the 'second Steve Jobs.' Holmes earned celebrity status in Silicon Valley as the founder of Theranos, a company that promised to revolutionise health by optimising blood testing, such that patients could test themselves at home using just one drop of blood. The Dropout on Disney+ Hotstar traces how influential men in science, politics, the startup economy, and tech hailed Holmes for her innovation and invested in her — only to realise that each of her lofty promises were hollow from the start. The technology simply did not exist, and would not for many years because of the lack of science to back it. But this did not matter in the face of Holmes’ confidence.


    Crucial to Holmes’ legacy was her image as a ‘prodigy’ with ideas that others apparently did not conjure up or were afraid to attempt — noble ideas with the potential to change the world. As the trust in her increased manifold, few bothered to look into the technology that she boasted about or the funds she raised for it.


    If Delvey was able to enter rooms because of the wealth and family connections she lied about, Holmes “broke the glass ceiling” because of the perception that she was self-made. She even styled herself in the manner of Steve Jobs by wearing a black turtleneck. If Delvey created an impression with couture, Holmes crafted a deep voice, quite unlike her feminine one at a higher pitch. In The Dropout, we see her change her voice almost overnight, in an attempt to be taken more seriously in a male-dominated industry.


    Both Holmes and Delvey peddled ideas of greatness while being driven solely by self-interest. This belief in oneself, even in impossible circumstances, comes from the sheer will to succeed, as well as a pedestalisation of the self. These are stories of people who yearned to be seen as extraordinary. Looking down upon others is a natural byproduct of such a way of thinking.


    Inventing Anna’s Delvey goes around accusing her detractors of being “basic”; in The Dropout, Holmes dismisses her detractors as being jealous or lacking her vision. At several moments, these women bemoan the fact that not enough people believe in them — seeing this as being a tragedy, while struggling to keep their flailing businesses intact.


    This unwavering belief in oneself, devoid of any self-doubt or healthy skepticism, could also stem from not having anything else to put faith into — neither a person nor an endeavour. Holmes and Delvey both come across as largely friendless. After soft-coercing multiple acquaintances and former friends into paying for expensive lunches, flight tickets, and hotels (citing credit card issues or delayed money transfers from her father), Delvey is left with all but one friend who is so committed to her that she began an Instagram account to document the outfits Delvey wore to court. Holmes’ only support system is her business partner and live-in boyfriend, with whom she shares a complicated relationship.


    Self-serving ambition cannot persist without the destruction of others — with no remorse. Inventing Anna sees Delvey putting her friends, who live pay cheque to pay cheque, into serious financial trouble by making them fund her lifestyle. In Holmes’ case, the damage is more far-reaching, whether it is patients who received faulty test results for AIDS and miscarriages, or the devoted employees she pushed out of the company, or worse, sued them, spied on them, and made them work in an environment of fear.


    Oftentimes, this destruction occurs because of Holmes and Delvey’s stubbornness, which is misjudged as being zeal and determination, and their impatience. Because they are always on the verge of being caught, immediacy and speed is crucial to their survival. Loans are expected to materialise in mere days, and data is tortured until it behaves the way they want it to.


    The con in both stories was relatively simple: evading any serious audit or examination by winning investors’ and associates’ trust through charisma, confidence, and promises. In The Dropout, Holmes builds a shield around herself by forcing employees to sign NDAs, and preventing them from fraternising at the workplace. Anyone who does not toe the company line — that is, anyone who is not up for covering up Theranos’ tracks and compulsively lying — is fired on the spot. In Inventing Anna, Delvey creates a fake email ID, writes up fake bank statements, and pretends to be a German business manager when a bank begins looking into her trust fund.


    Holmes, as a ‘self-made’ woman with purportedly good intentions, and Delvey with her fake old money background, were the sort of candidates that influential people want to take a bet on. They fit into the world they tried to conquer, which allayed any doubts about them being imposters. Their privilege, whether racial, class-related or social, protected them from scrutiny. Any person who believed in them or invested in them — especially those who trusted them blindly or did not exercise due diligence — would have felt too embarrassed to come out with the truth when the mask came off. Those looking to be associated with Delvey and Holmes were far from innocent, looking for their own share of capital and social capital.


    Another factor that ties together Delvey and Holmes is the way in which they weaponised their womanhood. When City National told Delvey that they could not offer her a loan, she stormed into their offices and asked if they would treat a man at Wall Street the same way. She was not wrong; while she served a prison sentence, the banker at City National, who tried to facilitate her loan, suffered nearly no long-term consequences. In The Dropout, when Holmes is asked if she ever experienced Imposter Syndrome as a woman, she agrees without so much as a hint of hesitation. Her response to a reporter’s investigative piece on malpractices at Theranos is to call it sexist.


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