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Shows like The Dropout, Inventing Anna, and Super Pumped tap into a uniquely 21st century kind of magical thinking.
In a way, it all began with the Fyre Festival. Five years ago this spring, the doomed “luxury music festival” unraveled in spectacular fashion over the course of a long weekend. Attendees arrived in the Bahamas hoping to party, sunbathe, and rub shoulders with influencers, but were instead greeted by FEMA tents, a lack of running water, and a cheese sandwich so bleak it became a meme. The festival’s founder, Billy McFarland, was revealed to be an incompetent grifter who’d built his entrepreneur reputation on empty promises. And he wasn’t alone.
A year later came the 2018 “summer of scam,” which brought us the stories of fake New York heiress Anna “Delvey” Sorokin, and fraudulent biotech maven Elizabeth Holmes. What binds these stories together is a very 21st century kind of magical thinking—the belief that a great idea can become a reality by sheer force of will. A company like Theranos, where the technology to back up the idea simply never existed, was still able to get away with the deception for years. That’s because Silicon Valley has always encouraged entrepreneurs to move fast and break things (to quote Mark Zuckerberg’s now-infamous motto), or at least to move fast and… figure out the details later.
2018 also brought a few high-profile flameouts for legitimate companies. Uber founder Travis Kalanick and WeWork founder Adam Neumann were both forced out of their own startups, in the wake of dramatic financial collapses that revealed how wildly over-valued they were. And this year, now that TV output is back in full swing after the pandemic, miniseries adaptations of these stories are arriving all at once.
For Joseph Gordon-Levitt, who plays Kalanick in the Showtime series Super Pumped, it was easy to understand the decisions his character made. “I think Travis, and all startup entrepreneurs, are in a position where if their company doesn’t grow like crazy, they lose the game,” the actor said during a Television Critics Association panel in February. “If your company achieves profitability and is doing pretty good, you won’t get venture capital investment. The economy doesn’t reward that kind of success. It rewards unicorns.”
That race to be extraordinary is also at the core of The Dropout, which digs into Elizabeth Holmes’s strange ascent to become the world’s youngest self-made female billionaire. Being a female CEO in Silicon Valley gave Holmes an instant unicorn factor that explains, in part, how she was able to convince so many investors, medical professionals, and even a former U.S. Secretary of Defense, to buy the snake oil she was selling. And according to Amanda Seyfried, who gives a fascinating performance as Holmes, it also helped that she truly believed in her company.
“From a psychology point of view, if you want to believe something badly enough, and you work so hard to make it true, physically and emotionally, then at some point you’re just going to have to choose whether or not it’s true,” Seyfried said. “We’re capable of such crazy things. Our brains are miraculous, and we can forget things, we can bury things, and we can create things. [Holmes] was incredible at creating things, including the story of Theranos.”
As the show depicts, numerous skeptics and whistleblowers were silenced, in increasingly brutal fashion, as Holmes and her partner Sunny Balwani doubled down on their snowballing deception. This was possible only because Holmes was operating in an industry that rewards that fake-it-til-you-make-it mentality. And in Netflix’s Inventing Anna, some of New York’s most elite social circles are similarly accommodating to Julia Garner’s Sorokin, who created such a convincing facade that she lived in boutique hotels for months without paying her bill or even putting down a card.
“I think startup culture really confused people about what’s real and what’s not,” Anna Chlumsky, who plays journalist Vivian Ward in Inventing Anna, told Elle. “People use words like ‘We’re pre-revenue right now’, and it’s just like…okay, that means you’re broke!” The Shonda Rhimes-created show is more about the New York culture scene than the tech industry—Sorokin planned to open a Soho House-ish members club for artists—but the story bears many similarities to The Dropout, and is steeped in the same kind of specific contemporary delusion. “I feel like the last twenty years has produced this sense that nothing is real, and we can all get by with our ideas and our dreams,” Chlumsky continued. The show emphasizes that point by depicting Sorokin hanging out with other contemporary con artists, including Fyre Festival co-founder McFarland and disgraced “pharma bro” Martin Shrkeli. (Both men are currently in prison on fraud charges.)
Unlike the stories of Holmes, Sorokin, and McFarland, Super Pumped and WeCrashed aren’t exactly about con artists. “We all walk around with Uber in our pockets, and none of us walk around with Theranos in our pockets,” Super Pumped co-creator Beth Schacter points out. Uber and WeWork are highly successful products by most standards, and yet over-ambitious growth and reckless, amoral leadership almost destroyed both.
Kalanick and Neumann both built their companies on an obfuscation, if not an outright lie. What they had were a transportation company and a real estate company, respectively, but both presented their firms as technology platforms. For Kalanick, calling Uber a tech company rather than a cab company allowed him to skirt numerous regulations in cities across the world. For Neumann, it seems the incentive was simpler. “A friend of mine who works in tech told me that as soon as you label yourself a tech company, you add a zero to your valuation,” WeCrashed co-creator Lee Eisenberg said. “That was something we thought about a lot. When you look at the WeWork story, it does feel like this pivot into tech was very cunning on Adam’s part.” Without that piece of shape-shifting, the company would likely never have gotten the multi-billion dollar cash infusion it did from investors. “The desire of companies to portray themselves as tech, and what that can do for them, is something we explore quite a bit in the show.”
The mythology of the charismatic founder looms large throughout all of these shows— Holmes, famously, modeled herself on Steve Jobs right down to the black turtlenecks and green juices. And the flip side of that charisma, to different degrees in all of these shows, is callousness. In Super Pumped’s pilot, Kalanick screens prospective employees by asking, “Are you an asshole?” The answer he wants to hear is yes; anything else is not useful to him. Both Kalanick and Neumann were accused of fostering a toxic, hard-partying corporate culture rife with misconduct. Holmes’s former employees have described a culture of isolation, retaliation and fear, which allegedly drove at least one core staffer to suicide.
As a viewer, it’s always tempting to play armchair psychologist with stories like these, especially if you’re familiar with the DSM-5 criteria for narcissism (grandiosity, check; preoccupation with power, check; lack of empathy, check.) But it’s probably more valuable to spotlight the corporate culture that rewards these traits again and again. Per Gordon-Levitt, ruthlessness is a feature, not a bug, for many CEOs like Kalanick. “Oftentimes to achieve that kind of unicorn success, you have to be Machiavellian,” he said. “You have to be predatory. And until we can change these incentives, until companies can be successful for doing the right thing—being kind and good to people, thinking about the long-term future—I think we’re going to keep seeing stories like this.”


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