Elizabeth Holmes, Billy Mcfarland, & Anna Delvey: How Scammers Keep Scamming

It’s probably not surprising that — at one point during my conversation with the folks behind HBO’s new documentary about Theranos CEO Elizabeth Holmes — a comparison to Fyre Festival came up.

Our obsession with scammers in culture is a long one, a rich tapestry full of brazen, audacious people who manage to lie, cheat, steal, and delude themselves to the top. But the past few years — gee, wonder if the timing’s coincidental? — folks like Fyre’s Billy McFarland, and Manhattan elite scammer Anna Delvey are front and centre in our minds. Everyone is dying to know how and why they all get away with it.

“You could say that Elizabeth Holmes was caught in the prison of belief,” Alex Gibney, director of The Inventor: Out for Blood in Silicon Valley, tells Refinery29. He also just so happens to have directed another major story he says has a connection the Holmes story: that of David Miscavige and Scientology. “The subtitle of [Going Clear] was: Scientology and The prison of belief. You could say that Elizabeth Holmes was afflicted by the prison.”

Holmes, McFarland, faux-German-Heiress Delvey, and even Miscavige, all succeeded because their ambition took precedence over all else. "[There's a line in the film that goes] 'you wouldn't want a world in which nobody's willing to over-promise otherwise nobody would open a restaurant,'” Gibney explained during the 2019 Television Critics Association Winter Press Tour. And he’s right: while ambition is certainly an admirable, necessary quality, when it exists in a vacuum, things can go very wrong.

Gibney put it thusly: “I'm interested in those people that have that kind of outsized ambition. You want that kind of ambition, right? But also … It's interesting to me when they refuse to reckon with the real world, and that ambition then becomes a very dangerous thing."

It’s like they always say when trying to date, right? Confidence is key. And, truly, confidence is the cornerstone of ambition — it only works if you have belief that you could possibly achieve your goals. Just look how far confidence and ambition took McFarland, as evidenced by both Fyre Festival documentaries. No matter that his prior business, Magnises, was a disaster: investors loved how confidently and (allegedly) charismatically he expressed himself and his goals!

Plus, it helps when you have money or a fancy background to start: something Delvey knew would take her far, hence her assertion that she was a German heiress. Money, credit, and allowances flow much more freely towards those that already have extremely disposable income. An association with wealth, status, and notoriety seems to confirm to a lot of people in positions of power that someone is guaranteed to go far.

This is perhaps nowhere more astutely observed than in Holmes’ own story. Though her family were not extreme one percenters, they weren’t exactly poor. She had incredible connections due to her upbringing, and some of her earliest investors were family members and friends. But even beyond that, Holmes would frequently tout her lineage to potential investors. Holmes’ mother was a congressional staffer and father was a vice president at Enron and held positions at government agencies like the EPA. His grandfather was a Danish physician who established the Cincinnati General Hospital and the University of Cincinnati's medical school after he married the wealthy daughter of the founder of Fleischmann’s Yeast. On her mother’s side existed a renowned entrepreneur. And this origin story took her unconscionably far.

"That was the most unbelievable thing,” Gibney explained quite giddily when I asked him about this. “When you see, what's his name? [prominent Silicon Valley venture capitalist] Don Lucas? Yeah. Okay. So he's going on and on and on about how this is in her blood,” he pauses for a beat, allowing the audacity of the statement to set in. “And... what sense in the world does that make? Her grandfather was part of a hospital and another grandfather was an entrepreneur, so now I'm going to invest a shitload of money? It was the craziest thing in the world.”

For most people it is. But when you’re a charismatic scammer building an origin story for yourself, few things could probably help spin your tale much better than a cutesy little button at the end. Especially if that scammer is a woman selling her tale to a bunch of old, monied men — which is exactly what she was doing, for the most part. “I mean, he literally said it was in her blood. I thought, whoa, because it's a phrase that just passes by, but I found in doing my research that was one of the most jaw-dropping lines I'd heard. So he gets involved because she has a few relatives who've done some shit. How crazy is that?"

It’s crazy because it works, time and time again. And the rest of us, sitting down here without the money and the power, are shocked and amused that the scam seems to just keep on working.