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Grifter Horror and the Problem of Startup Culture

It seems Spring 2022 was the season of grifters on prestige television. Prior to the pandemic, I was quite addicted to podcasts and shows about true crime, but after two years of COVID anxiety, as I mentioned in my last piece for Story Screen, I have been craving gentler fare in my entertainment. That being said, the fascinating thing about the four grifter shows I am about to talk about (Inventing Anna, SuperPumped, The Dropout, and WeCrashed) is how they capture the tension, excitement, and yes, passive voyeurism of the true-crime genre without getting into gristly details about stalking, murder, blood, and dead victims.

Interestingly, the four shows that landed this spring about grifters were all sourced from material originally generated from actual journalistic reportage in print media, publishing, and podcasts - and I had consumed all of the source material before these shows began to air. It's a curious thing to go into a show based on real events knowing exactly how everything ends, but it forced me to think about the art of adaptation, how best to portray in action the written word or disembodied podcast voices, and issues of dramatic license. I also have personal connections in varying degrees about the protagonists of each of the shows I am about to analyze for you - the first one being that each protagonist, save for Anna Delvey, is around my age: the Old Millenial cohort. (What I do have in common with Young Millenial Delvey – and YES, the younger cohort is a bit different from us oldheads – is that I used to work in an office building in Manhattan around the corner from the building she wanted to acquire for her start-up foundation; basically, I know the neighborhood she wanted to be associated with very well, and I very much understand why she wanted to be there.) The second one is, that both The Dropout and SuperPumped are shows about Silicon Valley startups. Elizabeth Holmes dropped out of Stanford to start her company Theranos in Silicon Valley - a mere two hours away from where I grew up in the San Francisco Bay Area. Travis Kalanick chose to set up his headquarters for Uber in San Francisco itself. And finally, we have WeCrashed, the story of Adam Neumann and the downfall of WeWork, and the show where I have the most personal connection of all - because, for a very brief while, I worked at WeWork HQ in Manhattan. I was introduced to Adam Neumann when I was hired. I had a really lengthy conversation with WeWork co-founder Miguel McKelvey during my first week there. It was a jolt to "see" these men again (as portrayed by actors), to see how closely the set looked like my former office, and to be reminded that I was lucky to get out of that company before things really went off the rails.

Enough setup. Let me take you through each show, in chronological order of its first air date:

Inventing Anna (available to stream on Netflix) tells the story of Anna Delvey (nee Sorokin) - a young woman of mysterious origin who arrives in New York, creates a fictional backstory of being the heiress to a wealthy German family, and essentially cons a number of friends and financial business partners in order to start the Anna Delvey Foundation. The Foundation, honestly, is a half-baked idea that seems like a combination spa/lounge/private club/art gallery without a clear focus, and she is obsessed with obtaining business loans to buy 281 Park Avenue South - a gorgeous building in the Flatiron neighborhood of Manhattan. She gets pretty damn far, too, by falsifying financial documents, cashing bad checks, and mooching off of her high society friends. She had no fixed residence, moving from hotel to hotel (being thrown out and blacklisted by each as they discover she has no way to pay her room fees or any services charged to her room). Eventually, after grifting multiple financial institutions, hotels, and friends to the tune of $275,000, she is caught and held in Rikers pending her trial.

Inventing Anna tells this story via journalist Vivan Kent (Anna Chlumsky) from Manhattan Magazine (a thinly veiled version of New York magazine, where journalist Jessica Pressler wrote an article entitled "How Anna Delvey Tricked New York's Party People" which served as most of the source material for this show), interviewing Anna and her friends, former friends, and former associates to presumably write the show’s version of Pressler’s article. Delvey is played by Julia Garner, who nails Delvey's bizarre mishmash Russian-attempting-to-be-German accent and brash, over-confident attitude with great aplomb - she is a far cry from her central Missouri hillbilly character Ruth Langmore in Ozark - and you get the feeling that she really enjoyed herself while doing this role. The miniseries is produced by Shonda Rhimes, and many actors known from the "Shondaverse" can be seen in key roles, like Katie Lowes, Jeff Perry, Kate Burton, and Josh Malina. It also features a great turn by Laverne Cox as Delvey's personal trainer/nurturing friend (who, inevitably, Delvey also screws over).

This show is pretty enjoyable but it goes absolutely bonkers in the last two episodes, when, after Vivian has turned in her article and received much acclaim for her work once the magazine hits the stands, she gets overly invested in Delvey's fate at her trial, despairs when Delvey is convicted, and the two share a tearful goodbye in the Riker's Island visiting room before she is bussed up to Bedford Hills Correctional Facility to serve her sentence. This ending is utterly bizarre, and according to Pressler, bears absolutely no resemblance to what actually happened when Delvey was sentenced or the nature of her relationship with Delvey. I understand the need for dramatic license when telling a story based on real-life events, but I see absolutely no reason why the show had the journalist who set out to uncover Delvey's many deceptions essentially also fall for the same charms and personality quirks and charisma that allowed her to scam so many people. Narratively, it makes no sense whatsoever, and it left me with a bad taste in my mouth. Subsequently, I learned that one of Delvey's real-life friends - a friend who was also a character on the show and seems to be the only friend from Delvey's circle who has stayed loyal to her - served as a consultant to the Shondaland producing team as the show was developed. This also left a bad taste in my mouth, as I don't see how a Delvey loyalist as a consultant could have helped tell this story with any measure of objectivity, and so it's perhaps not surprising that in the end, this show tries to make us feel sympathy for Delvey (all of those TEARS between Chlumsky and Garner in the Riker's set, my god!) even though by all accounts, first and foremost Pressler's New York feature that was the backbone of the show's structure, Delvey was a narcissist and probably a sociopath too. Obviously, narrative television is not documentary, but I'm sorry, I do not feel bad for Anna (Delvey) Sorokin one little bit, and I think it does a disservice to Pressler to have Vivian, the character based on her, display such a weird lack of necessary distance and journalistic ethics to be weeping with real sadness and remorse as the subject of her article is being taken to prison. It's weird. It's really, really weird.

Just so you know, Anna Delvey was sentenced to 2-12 years, was released after 2, and then was detained by ICE for overstaying her visa. This seems like an unfair Catch-22 – she was in prison when her visa ran out – but yeah no, I still have no sympathy for this woman at all. You reap what you sow, girl.

Inventing Anna stats

  • Grifter Scale: 10

  • Bizarre Fake Accent Scale: 10

  • Journalistic Ethics Scale: 3

  • Faithfulness to Source Material: 4

Should You Watch It: Eh, probably not unless you are a Julia Garner fan. This show is weird.

Let's move on to a different kind of weirdness - Elizabeth Holmes, founder of the biotech company Theranos, recently convicted for one count of conspiracy to commit wire fraud against her investors and four counts of actual wire fraud against said investors, and the eponymous dropout of The Dropout, Hulu's recent miniseries based on the ABC News podcast of the same name.

Holmes... is a weird person. Very, very weird. And I find this weirdness - and the story of Theranos that accompanies it - indelibly fascinating. For some backstory: Holmes came up with an idea for a blood-testing device that could test for many, many health conditions using only one drop of blood (instead of the multiple vials that a traditional arm-draw needs), dropped out of Stanford, convinced her parents to invest her college fund into her startup company (soon to be known as Theranos) to develop this device – and then somehow, even though the idea was fundamentally flawed, would have needed nearly a decade to develop properly, and probably would never have worked, she believed so strongly in her vision (or was really, really good at lying - we may never know) that she managed to convince a number of prominent people to invest in her company or serve on her board (or both): Larry Ellison. The Walton family. The DeVos family (yes, that DeVos). Rupert Murdoch. Henry fucking Kissinger. And of course, to his own downfall, the late George Schultz, former Secretary of Treasury and Secretary of Labor to Richard Nixon and former Secretary of State to Ronald Reagan.

She brokered deals with Walgreens and Safeway to put Theranos testing machines in in-store Wellness Centers well before the technology was ready. She and Theranos COO Sunny Balwani (also her boyfriend at the time) lied to everyone, including their own employees, about the efficacy of their technology, all while running diluted one-drop blood tests in Siemans testing machines hidden in an entirely separate lab from where the research was being done. She convinced these investors and partners to come on board through a combination of bald-faced deception (she Photoshopped the Pfizer logo atop reports on Theranos technology's capabilities WRITTEN BY THERANOS and presented them as proof that they had approval from the pharmaceutical industry) and capitalizing on her very bizarre brand of charisma: she was a young, blonde woman, hair in a slightly disheveled bun, red lipstick, dressed in head-to-toe black, compulsively drinking green juice... speaking in a very low, almost baritone voice. Honestly, when she spoke, she sounded like she was trying to impersonate a lumberjack. Sources who knew her when she was still at Stanford and when she was younger say that it is not her natural speaking voice - it seems she thought a lower voice lent her a sense of gravitas that was necessary when talking to all of these old white rich men to get them to give her money. Maybe it did. Or maybe they all just felt great supporting a young cute blonde kicking down barriers in a STEM field. Maybe a little of both. Probably a little of both.

Look, I am incredibly fascinated by Holmes because she is SO DAMN WEIRD. She's a year older than me and she somehow swayed all of these not-unintelligent investors and business partners (not to mention the numerous Stanford professors and researchers who served on her board and helped with product development) to believe in her completely implausible idea just by speaking confidently in a lumberjack voice and having blonde hair? She wants to be the next Steve Jobs (hence the wardrobe), but with blood testing instead of computers? She loves green juice?! SHE SPEAKS LIKE A GODDAMN LUMBERJACK, AND THE VOICE IS FAKE??!! I listened to both seasons of The Dropout podcast. I listened to Bad Blood: The Final Chapter, a podcast by Wall Street Journal writer John Carreyrou (who eventually wrote the expose that revealed Theranos’ fraud, which ultimately turned into a book, which I have also read). I know a lot about this woman. Maybe too much, because when I enthusiastically cajoled my boyfriend into watching the Hulu miniseries with me, he (not knowing ANYTHING about Holmes - despite her having been convicted in her trial late last year) mistook my fascination with Holmes to be a desire to BE LIKE HOLMES. That’s right: my boyfriend, who has known me for over a decade, thought I wanted to be Elizabeth Holmes.

I was quite mad. He was disabused of this notion very quickly and sharply.

But yeah, I admit, I was very hyped to watch The Dropout. This was a situation where I knew literally every single plot point before it happened, from her decision to leave Stanford to Theranos Lab Director Ian Gibbons committing suicide when he realized that the machines were being used on real patients even though they were nowhere near ready, to George Shultz's grandson Tyler, a Theranos employee, and his colleague Erica Cheung, serving as whistleblowers and sources for the Carreyrou article that began Theranos' downfall (causing George Shultz to essentially disown Tyler out of a bizarre sense of loyalty to Holmes; grandfather and grandson managed to reconcile shortly before the elder Shultz's death last year), to Holmes and Balwani's falling out in the aftermath of the article, to Holmes' eventual fate after being put on trial. And so what I can say is that the TV series is very, very faithful to the podcast that serves as its source material (as well as Carreyrou's), far more so than Inventing Anna was faithful to Pressler's New York article. It is exceptionally cast - Amanda Seyfried's performance as Holmes is absolutely incredible - if she doesn't win an Emmy, I'll drink a glass of green juice. Naveen Andrews is wonderful as the prickly, volatile Balwani. Stephen Fry is heartbreaking as Gibbons, and in a different way, so is Sam Waterston as George Shultz. Dylan Minnette and Camryn Mi-young Kim are great as Tyler and Erica. And also, some great appearances by Bill Irwin, Laurie Metcalf, William H. Macy, Alan Ruck, Josh Pais, Kate Burton, Rich Sommer, Michaela Watkins, LisaGay Hamilton, Ebon Moss-Bachrach, and Elizabeth Marvel - seriously, sometimes while watching this I'd turn to Tim and say "Holy crap, EVERYONE is on this show!" - as other pivotal characters in the Theranos story.

The Dropout is very, very good. It balances the need to adhere to its source material for accuracy's sake without sacrificing some necessary dramatic license to allow for narrative tension and a clear plot arc to structure the story as an effective television show (as opposed to a documentary). It's well written, well-acted, and well-produced. And Seyfried walks a delicate line in portraying the real mystery of Elizabeth Holmes (and perhaps what is truly fascinating to me, fake lumberjack voice aside): was she intentionally a grifter, like Anna Delvey? Or did she believe so strongly in her product that she lost sight of her ethical responsibility to her investors, her board, and her potential customers? Was she trying so hard to be the next Steve Jobs that she inadvertently neglected her duties as the CEO of her company? Or did she cultivate the female-Jobs person in a calculated manner, knowing that it would make her and her company famous? We don't know. We may never know. All we do know is, at the end of the day, she lied, and those lies got her convicted of fraud. She's going to jail. (At some point; she hasn't been sentenced at the time of this article's publication.) Balwani is currently on trial right now for his role in the Theranos mess, and I'm pretty curious to see how that shakes out too. And Theranos no longer exists.

The Dropout stats

  • Grifter Scale: 9. She may not have wanted to believe she was a grifter, but photoshopping Pfizer logos on reports written by the Theranos team and using Siemens machines to run blood tests while pretending to be using Theranos machines is not a good look.


  • Faithfulness to Source Material: 9. Some of the timelines do get compressed, but it doesn't fundamentally change the story.

Should You Watch It: Yes. It is very well done.

Moving on to SuperPumped - Showtime's take on the story of the founder of Uber, Travis Kalanick, and how Uber came to disrupt the taxi industry. To be perfectly honest, Kalanick (played here in glorious vileness by Joseph Gordon-Levitt) isn't really a grifter. He doesn't fool anyone into anything unless you count fooling his drivers into believing they could make a living wage by being drivers. Kalanick's downfall was how deeply he bought into the most toxic elements of Silicon Valley startup culture. SuperPumped is essentially The Wolf of Wall Street but with ridesharing instead of stocks. We see company parties turn into ragers that destroy hotel rooms, we see female employees being subjected to blatant sexual harassment with no recourse, we see Uber using some dubiously legal technology to skirt issues with taxicab unions, and we see Kyle Chandler (Coach Taylor!) as Bill Gurley, a famous venture capitalist who invests in Uber and becomes increasingly disheartened by Kalanick's behavior and business decisions, we see Kalanick dump his supportive and sensible girlfriend in favor of a younger woman, and we see that younger woman become disgusted with Kalanick's behavior and leave him. Not very grift-y, unless you see Kalanick's attempts to dodge Gurley's tough questions as a kind of grift. Honestly, Kalanick is the only protagonist in the four shows I'm writing about here who seems to be somewhat self-aware when called out on his bad behavior; when video footage is leaked from an Uber driver's dashcam of Kalanick being verbally abusive to said driver, Kalanick immediately knows how much trouble he's in and literally lies down on the floor of an Uber HQ conference room in the fetal position begging to talk to his mother. (Yes, this melodramatic sequence actually did happen in real life.) When he is eventually ousted as the CEO of Uber, he seems to know it is coming and accepts his fate. Kalanick is kinda gross, but he's not delusional the way Anna Delvey or Elizabeth Holmes seems to be.

I'll be honest, I don't have as much to say about SuperPumped as I do about these other shows. I've read the book it's based on and it's pretty faithful to the source material. That being said, there are some very showy stylistic choices that the producer's made that feel very self-conscious and honestly make the show kind of difficult to follow. Characters break the fourth wall randomly. Kalanick envisions a fake PowerPoint presentation behind him as he tries to explain to the Apple Store execs why he flouted their policies to keep the app in their store. And the whole story is narrated intermittently by a faceless Quentin Tarantino. Why? It's not necessary. We're already seeing the world through Kalanick's eyes. Forcing Tarantino's very distinctive voice on top of the very heightened world that comprises Uber HQ and takes away from JGL's very strong performance. I really don't get it.

Uber obviously still exists. I suggest you use Lyft instead. Or if you’re in Manhattan, just take a damn yellow cab. They’re good, they do their job well, they’re cheaper. What, you’re too good for a cab? Grow up.

SuperPumped stats

  • Grifter Scale: 2.

  • Toxic Masculinity Scale: 10+++

  • Faithfulness to Source Material: 8, but it's hard to tell with the weird stylistic production choices

Should You Watch It: Maybe. (I mean, who doesn't love JGL and Coach Taylor?)

And now we come to WeCrashed, Apple TV+'s epic tale of the fall of WeWork founder Adam Neumann and the notoriously scuttled WeWork IPO, and a not-particularly welcome trip down memory lane for me, a former WeWork employee who ran for the hills in 2015. To start with: Jared Leto's performance as Neumann gave me chills. I looked at him and I was like, I fucking KNOW that guy. Kyle Marvin, the actor playing WeWork co-founder Miguel McKelvey, also gave me chills. I remember the conversation I had with him when I started working at WeWork, how kind and genuine McKelvey was. He was a really sweet guy. I was able to pinpoint exactly in the narrative when I started working there and when I jumped ship. It didn't take long for me - by which I mean, it took less than three months, and I'm sorry to say (or #sorrynotsorry) that I basically fled the place after being literally locked in the building during a mandatory office Xmas party. They had security standing by the elevators barring people from leaving. I wish I was kidding, I really do. I escaped through the fire exit and set off the alarms as I ran down four flights of stairs and barrelled out onto 18th street towards the 7th Avenue 1 train. I never returned.

Was it unprofessional for me to do that? Yes, but that was WeWork in a nutshell. Mandatory "Thank God It's Monday" parties that lasted well into the evening, with IPA flowing freely on tap. Kombucha, baristas, fruit-infused water, and tons of snacks are available during the day. I witnessed the beginning of WeLive, WeWork's doomed attempt at communal living (let's put even less space between our personal and professional lives, woo!) but I left early enough that I didn't get to experience all of the other wackadoo stuff (the "Summer Camp" employee retreats that were a combination of SuperPumped ragers and mandatory cult worship of Neumann as he delivered speeches about how WeWork was going to "change the world's consciousness", the bizarre investments in peripheral companies that had nothing to do with WeWork - such as a startup that creates artificial waves for avid surfers? - and Rebekah Paltrow Neumann's (Adam's wife, and yes, cousin to THAT Paltrow) half-baked school WeGrow, where small children were taken to the Neumann's farm in upstate New York to grow produce and then try to sell it to WeWork employees (to teach entrepreneurship), daily yoga, guest lectures from WeWork employees about business, podcasting, and startups, and motivational speeches from Adam about - what else? - "changing the world's consciousness". Not a whole lot of "reading, writing, or 'rithmatic," and all to the tune of $22-44K a year. Did I mention that Rebekah Neumann has no background in education? I never met her during my brief tenure at WeWork - if I have my timeline right, that was when she was still a yoga instructor and aspiring actor.

This might be a good time to remind you that WeWork provides co-working space to freelancers. It's a COMMERCIAL REAL ESTATE COMPANY. Someone, please explain to me what the fuck renting desks has to do with changing the world's consciousness?

Adam Neumann's fundamental weakness is that he believes so strongly in his own hype, and he is so very charismatic, that he is able to convert his employers into believing in his kind of unclear vision of world domination almost as if he is a cult leader. I remember the culture at HQ. Everyone drank that Kool-Aid. By the gallon. I found it terrifying.

We were all also underpaid, while WeWork expanded with locations all over Manhattan, then all over the country, then internationally, and the Neumanns just got richer and richer (I believe in the end they owned five homes) with each new investor and venture capitalist Neumann was able to bring on board. Rebekah began to get more and more involved with the company, to the point of sidelining poor well-intentioned McKelvey, who was in over his head. Again, just like with Elizabeth Holmes (and Anna Delvey), we see how easily rich investors are swayed by entrepreneurs with unsettling charisma even when they are peddling absolute bullshit.

WeWork's eventual downfall was the aforementioned scuttled IPO in 2019. According to the show, Adam was initially reluctant to pursue an IPO because he knew it would require full financial disclosure and he knew that the company's debt was growing and its valuation was all smoke and mirrors. (For the record, and contrary to what WeCrashed portrays, I know that WeWork was chasing after the potential of an IPO in 2015 - it may be that Adam was resistant, but when I was interviewing there the hiring manager and recruiters were aware that I had worked at Shake Shack when it went public, and I strongly suspect in retrospect that this was the only reason why I was hired even though I did not play a role in the preparation for Shake Shack to go public.) WeWork publicly filed the IPO paperwork in August 2019. As predicted, they faced much scrutiny of their finances and leadership. Softbank, WeWork's biggest investor, ended up investing far less money than Adam had been led to believe, which led to concerns about profitability. Adam's bizarre antics (including but not limited to smoking weed on a private jet - essentially hotboxing it - serving employees tequila shots after discussing layoffs, the aforementioned artificial wave company investment, trademarking the term "We" and forcing WeWork to buy it back from him) did not help. Neither did the comically absurd prospectus that Adam and Rebekah presented to underwriters (the writing of which was portrayed in hilariously nonsensical glory towards the end of the miniseries, and was just weird enough that I 100% believe it is exactly what went down as the Neumann's were crafting it) - a prospectus that, instead of following the traditional format of financial disclosure, instead amounted to a colorful brochure about an umbrella filing with three arms - WeWork, WeLive, and WeGrow - complete with photos and a LOT of information about Adam Neumann's biography, mission statement, values, dreams, goals... let's just say this document was absolutely ridiculed by financial experts and was likely the nail in the coffin for Neumann as CEO. He was asked to step down by the board at the end of September 2019. Softbank took control of the company in October and gave Adam $1.7 billion to step down as chairman of the board. (That's a golden parachute if I ever saw one.) The IPO was then postponed indefinitely. The company, pre-filing, had been valued at $47 billion. After this IPO debacle, the valuation dropped to $10 billion. In November 2019, WeWork laid off 2400 employees.

I am so glad I left WeWork in 2015. Did I mention that already? Yeah.

At any rate, WeCrashed is a great attempt at telling the story of WeWork's downfall as non-judgementally as possible, which I think is admirable given the absolutely wild story it is telling. The series is based on Wondery's podcast of the same name and they are pretty faithful to the source material. The Neumanns are clearly insane, but Jared Leto and Anne Hathaway (as Rebekah) do an admirable job of trying to portray them earnestly, as real people who really genuinely believe in what they are peddling. WeCrashed does attempt to use the character of Rebekah as perhaps a candidate for a redemption story - we see how Adam's workaholic tendencies cause their marriage to suffer and her own personal aspirations get squashed - but then she demands her own office, starts instructing HR to fire people for "bad energy", and comes up with the unbelievably horrendous idea that is WeGrow, so... any sympathy I may have found for her went out the window fairly quickly. Yes, they are grifters. Yes, Adam lies constantly about WeWork's profitability and valuation. But no, I genuinely do not think that Adam, Rebekah, or Miguel (before he was sidelined) were consciously trying to swindle anyone. They were drinking their own damn Kool-Aid too. If anything, they are just revealed as terrible businesspeople who knew how to talk a good game, but unlike Holmes, there was no intentional malice at play. Just... cluelessness, and a lot of New Agey language.

WeWork still exists now, and it finally went public last year. I think the new leaders are fully aware that it is actually just a commercial real estate company, and that's just fine. It's one of the biggest in the world, after all.

WeLive and WeGrow, thankfully, are long gone.

WeCrashed stats

  • Grifter Scale: 10 (but an oblivious 10)

  • Bizarre Accent Scale: 1 (Adam Neumann grew up in Israel, his accent is authentically Israeli and Jared Leto does it well, so let's not call it bizarre, that's not nice)

  • Bizarre Voice Scale: 2 (Rebekah Neumann's voice is lower in timbre than Hathaway's, but Hathaway does a decent job with it, and also that is actually what Rebekah Newman sounds like in real life, there are no fake lumberjacky shenanigans here, so let's not call it bizarre, that's not nice either)

  • Is This Company Actually A Cult Scale: 10 (at least until 2019!)

  • Faithfulness to Source Material: 7. There are some fictional characters invented to convey some of the real-life machinations of the company, and some timeline scrambling, but nothing that fundamentally changes the reality of WeWork in the Neumann Era

Should You Watch It: Yes, unless you used to work at WeWork, in which case please, take it from me - don't. These memories are not fun ones.

So let me leave you with this - why, all of a sudden, in the spring of 2022, did these shows about professional grifters, shady entrepreneurs, and toxic people come at us back to back to back to back? Why were three of them about startups? Why were all four of them roughly taking place during the same timeframe - in all honesty, these four shows exist in the same temporal universe, despite being on four different streaming networks. Why, now, is "Grifter Horror" in the zeitgeist?

We love to gawk when the powerful fail - the rich and powerful - and I think that's why suddenly a rash of shows about real people who tried to shortcut making themselves rich suddenly cropped up this year. If I want to go down a pop psychology rabbit hole, maybe it's because many of us ended up suffering financially due to the first year of the pandemic. Maybe it's because the pandemic rendered many of us a feeling of powerlessness. So there is some satisfaction watching Delvey, Holmes, Kalanick, and the Neumanns try to grift - whether intentionally or due to earnest delusions of their own grandeur - and have their lives blow up. None of them win. All of them look foolish, corrupt, or maybe just plain stupid.

But I think there's something larger at play here. The reason why all of these would-be grifters survived for so long is because financial institutions, venture capitalists, and investors are desperate to find “unicorns”. In finance, a "unicorn" is a privately held startup company with a current valuation of $1 billion or more. Theranos, Uber, and WeWork were considered "unicorns" in their respective heydays. Delvey, in her own way, was a "unicorn" on a slightly lower scale – she fooled a lot of people into thinking her financial worth was a lot more than it actually was.

Unicorn hunting, to me, feels like a fool’s errand. If we look at these four miniseries, we can see that most perceived unicorns actually are not unicorns at all. Unicorns are fucking rare. That's why we call them unicorns. There is only one Apple. There is only one Google. There is only one Facebook. The technology they created is hard to duplicate and even harder to dominate at the level and scale that those companies have. And at the heart of it, the only real attractive thing about a Wall Street unicorn is the potential of a massive payout for all who get in on the ground floor. That’s why Anna Delvey was able to fool so many people into thinking she was an heiress. That’s why Elizabeth Holmes had Rupert Murdoch, Henry Kissinger, and George Shultz eating out of her hands. That’s why Bill Gurley believed in Travis Kalanick and invested in Uber. That’s why Adam Neumann’s woo-woo rhetoric about changing the world somehow through renting desks to freelancers appealed to a huge investor like Softbank.

It’s really quite simple: at the end of the day, the reason why all of these grifters got as far as they did before meeting their downfall is because of capitalism. Money (or the perception of money) is so important that every potential investor or business partner or board member lost their damn minds and failed to complete proper due diligence – not just into the financials, but into the technology being created (Theranos) or the concept being sold (Anna Delvey Foundation, WeWork) or what exactly is to be gained, besides money, by “disruption”, (Uber) which is what caused these back-to-back unicorn collapses. And honestly, I think it stands to reason that it wouldn’t hurt to do some due diligence into the character of the entrepreneur asking for money before handing it over fist by fist, no matter how charismatic you find them.

Sociopaths are known to be quite charismatic, after all.

This lack of due diligence is a huge problem. Theranos could have hurt actual patients if it hadn't been stopped. WeWork actually did harm their employees with their toxic cult-like culture, even before the mass layoffs and the scuttled IPO damaged them financially. Anna Delvey not only defrauded her friends, but she also defrauded financial institutions – seemingly all just by speaking in a foreign accent, claiming extreme family wealth, and general shamelessness, which is mind-boggling. Uber, while not explicitly grifty in the way Delvey, Theranos, and WeWork were, was gaining a lot of notoriety for being a "disruptor" - another buzzy Wall Street word like “unicorn” that ultimately means YAY WE CAN MAKE SHITLOADS OF MONEY OFF OF THIS LET’S DO ITTTT. (Again, what is the goal of “disruption”? Did Uber really make the world a better place, at the end of the day?)

Unicorn hunting is a problem, and it feels like a uniquely American one. I worry that it won't stop. I think people might be careful not to be duped by another Anna Delvey because her grift was so wild and so blatant. And maybe the biotech industry has learned a lesson from Theranos. Or maybe not: a chyron at the end of The Dropout notes that a female entrepreneur was advised by a potential investor to dye her blonde hair a different color so as not to resemble Holmes. (It seems the lesson they learned is “Don’t trust blonde women with ideas?” How depressing.) I honestly hope everyone on Wall Street has learned some sort of lesson from the WeWork disaster.

But I'm not so sure. Everyone wants to find the next Steve Jobs. Everyone wants to say they believed in two crazy kids working out of a humble garage like Larry Page and Sergey Brin. Everyone wants to claim responsibility for discovering a Mark Zuckerberg-like wunderkind. Does the grift stop here, now that we’ve seen how the mighty have fallen? Delvey and Holmes in jail (or about to be), Kalanick and Neumann exiled from the companies they’ve founded? I hope so, but I’m not holding my breath.


Reeya Banerjee

Reeya is a musician and writer based in NY's Capital District. Her debut album The Way Up was released on January 27, 2022. She can frequently be seen in her car on the NYS Thruway cursing traffic on her way to the Hudson Valley for band rehearsals or to Brooklyn for recording sessions. In her other life, she works as a staff accountant for a management company that oversees veterinary practices nationwide, enjoys watching Law & Order SVU returns while eating gummy bears, and has a film degree from Vassar College that she does not use.




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