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Inside the rise of the woman grifter

Figures like Elizabeth Holmes and "fake heiress" Anna Delvey do more than offer a good scam story—they open up a whole new way of thinking about young women's relationship to capital

By Rebecca Liu  

Women like Elizabeth Holmes and Anna Delvey don't just appeal to our sense of schadenfreude—they challenge a world that tells us we must work constantly to achieve greatness. Photo: Prospect composite

In the alleged end-times of liberal market democracy, it is fitting that we are seeing more stories around high-profile financial grifters.

HBO’s recent documentary The Inventor: Out for Blood in Silicon Valley, renewed public interest in Elizabeth Holmes, the disgraced founder of healthcare start-up Theranos, who was discovered to have built her $9 billion dollar needle-free blood testing company on technology that did not quite work.

Last week Manhatten “socialite scammer” Anna Delvey, who hobnobbed with A-list celebrities, stayed in five-star hotels and almost set up her own charitable foundation before landing in Rikers Island jail, stood before court facing grand larceny charges. Her story went viral on social media before being snapped up by Netflix showrunner Shonda Rhimes and HBO writer Lena Dunham. Both media companies are now developing television series inspired by the fake heiress’s story.

The trend continues in cinema. Hollywood recently announced the development of Hustlers, starring heavy hitters such as Jennifer Lopez and rapper Cardi B, which tells the story of a group of former strip club employees who band together to scam their Wall Street clientele. Hustlers follows other Hollywood blockbusters with women scammers such as 2018’s Ocean’s 8 and upcoming con-women buddy film The Hustle. Grifting has long been seen as a thing done by men, to other men. The time of the woman grifter has come.

It would be beside the point to ask the question often posed whenever news about women doing something that is not “traditionally” feminine comes up: “is this emancipatory—perhaps even feminist?” Of course, money helps people enjoy a greater degree of freedom, but an individual woman successfully enriching herself is hardly a collective political triumph.

And yet the ways in which women like Holmes and Delvey have been dissected in the public eye can teach us valuable lessons about our attitudes towards young womanhood and capital. Their images have been discussed with wild fervour, giving these women an almost mythic status. Elizabeth Holmes, we are told, has an unnervingly low voice; she does not appear to blink, brush her hair, or own another jumper besides that one black turtleneck. Anna Delvey’s secret weapon to her grifting, it is claimed, was her nondescript appearance (it has also been argued that you could have ascertained she was not particularly wealthy due to the state of her hair). She is currently garnering widespread admiration for wearing a black choker necklace in court.

Compare this to the muted reception to Billy McFarland, the man behind Fyre Festival, the infamous luxury music retreat gone wrong. While much was made of the festival itself—the viral images of the lonely portable toilets, unappetising cheeseburgers, and disaster relief tents—McFarland’s public image has not seen the same scrutiny (and near-deification).

An image from Delvey’s Instagram, tagged to The Standard hotel in New York.

It would be easy to charge sexism here, and others have. But there is something else going on, summed up by a pithy phrase Delvey’s attorney Todd Spodek uttered in her defence: “Anna had to fake it until she could make it.”

To be a young woman today is to be steeped in the language of artifice. Our public institutions have been hollowed out and “meritocracy” is increasingly seen as a myth—yet we are still instilled with messages about the importance of empowering ourselves, striving for self-made success, while remaining sufficiently non-threateningly and compassionately feminine.

In this confusing landscape, our fascination with grifters is a symptom of a generation’s widespread disillusionment with the myths of self-sufficiency, as well as the suggestion—occasionally offered up by some well-meaning feminists—that a uniquely nurturing and caring womanhood can be sent in to save this crumbling order.

In an era dominated by Silicon Valley tycoons with loose and questionable attitudes towards gender equality, who confused the task of getting people to online with meaningful philanthropy, Holmes appeared like the perfect foil. Her product—a needle-free way to do blood testing—actually seemed to have some relevance to real life. She was a genius at a time when geniuses seemed rare. As newspapers heralded her as the first self-made female billionaire, we were reminded that young women could be successful business leaders: that Silicon Valley sexism could be overcome, and that you too, young lady, could be this, if only you tried a bit harder.

Delvey, meanwhile, effortlessly conned the same people that young women are encouraged to revere: A-list celebrities, fashion’s inner circle, the door staff of exclusive five-star hotels. Delvey’s story offered her young female fans two sets of guilty releases: first, they could revel in their schadenfreude against the people, places, and images that had made them all insecure. Then, they were able to vicariously luxuriate in the idea of accumulating vast, delectably unearned hordes of riches, a fantasy in direct contradiction to their downwardly-mobile economic realities.

That Delvey eschewed any appearance of humble contrition and showed up polished and cool in court, dressed in black flats—she reportedly wanted to wear stilettos, but was denied permission by the court—made the case again for her status as a generational icon. Gone were any aspirations to “climb” any meaningful career or personal ladder. In a broken system, her sleek dress seemed to say, cash in on what you can.

Perhaps what is most compelling about these women is how they seemed in on the joke the whole time. Holmes’s trademark baritone, black turtleneck, and the unnerving wide-eyed stare—now fodder for our glee after her fall—were also integral to her becoming an iconic entrepreneur. Delvey hired a celebrity stylist for her court appearance. Spodek has confirmed as much: “Anna’s style was a driving force in her business, and life, and it is a part of who she is.” When you enter a space where you are considered an exception, you become less of an individual person, more a symbol to be endlessly plumbed.

In spite of the triumphalist, breathless manner in which their stories are discussed, neither of these women has “won” in any meaningful way. Holmes and Delvey are likely to face extensive legal repercussions, if not jail time. US Immigration and Customs Enforcement (ICE) officials have confirmed they intend to deport Delvey to Germany if possible.

Yet for those watching at home—particularly for young women who have had their own appetites and ambitious monitored since birth—these two women remain Icarus-figures who wanted too much and almost got it. The stories of Elizabeth Holmes and Anna Delvey are not so much about their lives, but rather the collective disillusionment of a world that tantalises wild self-made riches while providing so few lawful avenues with which to get there. We occasionally get the criminals we deserve.

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