Con artist entertainment is certainly having a moment.

Between Netflix and Hulu’s dueling documentaries on entrepreneur Billy McFarland’s fraudulent Fyre Festival and television shows like Dirty John, it’s clear that we can’t get enough of grifter stories.

The latest story? The podcast The Dropout, which follows the rise and fall of the brilliant, potentially sociopathic, Silicon Valley startup mogul Elizabeth Holmes and her now-defunct company, Theranos.

Elizabeth was poised to be a rising star in Silicon Valley. At one point, she was the world’s youngest female self-made billionaire. Now, she is under criminal indictment and faces up to 20 years in prison. The Dropout unpacks the story of Elizabeth’s unfathomable deception and tries to pinpoint exactly where things went wrong.

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Photo: Elizabeth Holmes / Source: Twitter

The podcast thoroughly examines how Holmes dreamed of becoming the Steve Jobs of medicine, down to the black turtlenecks, and refused to accept her own failures when she couldn’t materialize her product.

Elizabeth had claimed that her company, Theranos, had developed a needle-free blood testing technology that could provide a wealth of medical information with just a single finger-prick and drop of blood. When investors wanted to try the technology for themselves, she would administer their blood tests using Theranos technology. She would then take the investors out to lunch while her lab technicians used rival companies’ machines to get the actual results.

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The podcast is thorough and compelling. However, in many cases, it seems to give Elizabeth the benefit of the doubt, alluding that her troubles were a result of the “fake it ‘til you make it” mentality gone too far.

But Elizabeth Holmes is just another example of white privilege gone unchecked. Holmes was raised in an upper middle class family; her dad was a vice president at Enron and her mother worked as a Congressional aide. As a child, when people asked what she wanted to be when she grew up she would tell them, “A billionaire.”

the dropout elizabeth holmes
Photo: The Dropout Podcast / Source: Instagram

She attended prestigious university Stanford before dropping out at age 19 to fulfill her entrepreneurial dreams. Her earliest investments were in part provided by the powerful connections her parents had. Elizabeth was set up for success and she manipulated that expectation to her benefit. She strong-armed her way to the top and threatened anyone who compromised her with litigation.

Despite being a college dropout, her claims to have invented a state-of-the-art blood testing machine were taken at face value, and she very quickly netted millions of dollars from investors. She was splashed across magazine covers and television shows, a thin, white, classically beautiful face of her company.

She manipulated her incomplete education to appeal to Silicon Valley’s admiration of the college dropout; she was immediately touted as a brilliant ingénue a la Mark Zuckerberg, rather than as an undereducated and unqualified teenager. No one outside of Theranos ever questioned Elizabeth’s credibility or her competence. But would a person of color have been awarded the same kind of credence? Probably not.

It’s impossible to listen to Holmes’ story without drawing comparisons to fellow millennial fraudster Billy McFarland. Like Elizabeth’s startup, Billy’s now-infamous Fyre Festival existed entirely on his ability to charm investors out of millions. Where Elizabeth was selling technology that didn’t yet exist, McFarland was promising an exclusive getaway and luxury villas that never materialized.

Both Elizabeth and Billy were born into upper middle-class white privilege that simultaneously set them up for and demanded success. Such enormous expectations placed them in a pressure cooker, and cutting corners by manipulating the very foundation that placed those expectations was the only way they could measure up. In Elizabeth’s case, she still hasn’t expressed remorse for her actions or refunded investors any of the money they put into her company.

Our fascination with scammer stories seems to be far from satiated. In addition to The Dropout podcast, the Theranos scandal is also set to be the subject of an upcoming HBO documentary and a feature film. But what is it about the con artist entertainment craze that draws us in and keeps us hooked?

Perhaps in part because our own president is such a notorious grifter. Donald Trump manages to hold the most powerful position in our country despite having a laundry list of dubious business practices and broken promises. Yet, he still manages to avoid consequences, even though there’s nothing but hot air behind his controversial statements and his “successful businesses.”

Additionally, our social media obsession, specifically Instagram, fuels the fire of con artist culture. Instagram is essentially ad content on an individual level; so many people are selling something, whether it’s an image or a tangible item, and trying to get ahead by marketing themselves in a certain way. Everyone is trying to cultivate their best selves, and if you need to photoshop a waistline or throw on a filter to execute that, who cares? The illusion of success is important for so many Instagram influencers and perhaps more important is that the success looks like it was attained effortlessly; the truth falls by the wayside when you’re tallying up your follower count.

This latest batch of con artists is doing essentially the same thing, just on a higher level. Billy McFarland launched Fyre Festival with a massive promotional video of Instagram models swimming with pigs on a Bahamian island. Elizabeth Holmes would frequently appear on talk shows and in magazines endorsing her product, and much was made of the photo shoot she did touting the faulty Theranos vials.

People are fascinated by these grifters cutting corners and getting so close to success, but they’re also delighted to watch them fail. There’s something satisfying about watching rich, entitled millennials fall from the pedestals upon which their parents placed them. Considering that our president has yet to face any real consequences for his schemes, seeing other scammers get the penalties they deserve is an added bonus of the docu-escapism.

But it’s important to remember that, while it might be fun to watch a rich kid build a fake business on pure bluster and then be shocked when the façade crumbles, so many people are hurt in the process. While Elizabeth might be the one confronting legal consequences, she will almost certainly bounce back. Conversely, many of those who were simply caught in her path of destruction likely won’t be awarded the same privilege.

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