The Downfall of Iconic Startups Takes Over Hollywood

Three entertainment’s big names simultaneously premiered drama series on the same theme: the meteoric rise and spectacular fall of three young startup founders who promised to change the world. Three different takes on Icarus’ myth.

With “WeCrashed“, Apple bet on the charismatic Adam Neumann, who promoted a new vision of coworking by founding WeWork in 2010. The Israeli entrepreneur created a multibillion-dollar business but was later fired from his own company due to burning investors’ millions and other irregularities. The series manages to achieve the difficult feat of portraying the founder, brilliantly played by Jared Leto, as someone extremely charming and at the same time a unique trickster. Anne Hathaway, as his partner, pulls no punches either. “WeCrashed” can be streamed globally on AppleTV+ and, like the other two shows, is a limited series, so this will be its only season.

Showtime commissioned the creators of its hit show “Billions” to develop “Super Pumped“, which tells the story of the rise of Uber and Travis Kalanick, the executive responsible for revolutionizing transportation worldwide. It shows how the same competitive drive that led him to conquer the planet ended up burning him (and almost his company). “Super Pumped” also features big names, with Joseph Gordon-Levitt as Kalanick, supporting stars like Uma Thurman and Elizabeth Shue, and Quentin Tarantino as the narrator. It is the only show that has not yet premiered in Latin America. But it will soon: May 12 on Paramount +.

With “The Dropout”, Disney secured the most shocking recent fiasco in recent years— not only in the startup world. The series tells the story of the biotech company Theranos and its founder, Elizabeth Holmes, who could face up to 20 years in prison next September for fraud committed in the context of creating a medical diagnostics company that turned out to be a hoax. Starring Amanda Seyfried, The Dropout premiered on Hulu in the US, while in Latin America it premiered on one of Disney’s platforms for the region, Star+.

All three shows have much in common, and we could even say—Marvel allowing—that they occur in a shared universe. In them, we see these founders dazzling shareholders with their great talent for storytelling. Their delusions of grandeur and how they justify their dark deeds with a supposed pursuit of the greater good for humanity. The hectic life of startups, their waste of resources, millionaire parties, and Don Julio tequila. The toxic internal cultures, even at “hippie” WeWork, and how neglecting those cultures opened the door to scandals. They also show how they underestimated their relationship with the press or delayed giving importance to their communications teams. And also—despite how much these companies are questioned—how great they were.

However, these are not cookie-cutter shows. Beyond their similarities, each one tells its own story and profiles a unique character. For this reason, I’ll tell you what stands out the most about each one. 

Super Pumped: the “asshole” who founded Uber

This is no Mad Men, but it reminds you of Draper and its gang through its hyper-masculine culture, competitive environment, and the characters’ fractures. Although the series’ style is more akin to Adam McKay films (“The Big Short): fast pace, dark humor, fourth-wall-breaking, on-screen animations, and cool narrator—Quentin Tarantino, who took the job because he is a fan of “Billions.”

“Super Pumped” is the most shallow and sensational of these shows, but that probably makes it the most entertaining to watch. It has memorable scenes worthy of “The Hangover,” such as an internal Uber event in Las Vegas with a live Beyonce presentation, endless alcohol supply, and million-dollar damages that Kalanick paid the following day laughing as if it was nothing. This party cost him 25 million dollars, the same amount as Uber’s first major investment round.

The show is also entertaining because of the emergence of the Uber service itself, showing how features we take for granted today came to be, such as dynamic pricing, which Kalanick—humble as he is—calls the greatest value proposition of the modern era. Or how the change of the company’s original name UberCab to Uber was a trick to present itself as a “car-sharing” company instead of a cab service. It’s fascinating to watch how the company, born in San Francisco, gradually conquered other cities and dealt with regulators, or how it reacted to its first direct competitor, Lyft. Bottom line: is fun witnessing the dawn of a mobility system that changed the rules of the game.

Other more intimate aspects of the story make it appealing. “Super Pumped” is probably the series that devotes the most time to board meetings and the crucial role of venture capitalists, to the point that Benchmark’s Bill Gurley is almost a main character. He’s the most involved board member and sort of Kalanick’s personal advisor, despite Uber CEO’s later preference for Arianna Huffington (Uma Thurman), whom he gets her a seat on the board.

“Super Pumped” is also the show that most embraces other key players in the tech industry. Although Kalanick doesn’t get to know his idol, Jeff Bezos, he does connect with Google’s founders and Apple’s top executives, with whom he had an ambivalent relationship, ranging from complete admiration to a childish impulse of challenging them, with salient scenes like a meeting with Larry Page in which he ends up looking pathetic. In other scenes, Uber’s CEO comes across as brilliant, both for his unparalleled drive for competition and his ideas. “We consume what we want, and our brains figure out a way to justify it later”, he says, in the context that the company’s blemishes are of little consequence if the service is excellent.

How close is “Super Pumped” to reality? From Mike Isaac, a journalist who covered Uber for years at The New York Times and the author of the book on which the production is based, we know that much of what is told here happened just as portrayed. Like Greyball, the software Kalanick created to send phantom Ubers to city inspectors. Other elements of the show veer more into creative licenses’ territory, such as when Kalanick asks job applicants “Are you an asshole?”—expecting an affirmative answer.

For an in-depth comparison of fact and fiction, see this article in Time.

WeCrashed: Jared Leto and the millennials

“WeCrashed” is the series with the highest artistry of this wave. It is the most cinematic, the one that best approaches its main characters’ mystique, and the one that strikes the deepest emotional chord. The latter, in part, thanks to the peculiar romance between WeWork’s founder and Rebekah Neumann, a yoga instructor and unsuccessful actress from New York played by Anne Hathaway.

The series shows that Adam Neumann wouldn’t have been able to build his coworking empire without her. But then, once the company got off the ground, she became a liability. Someone who gives an unnecessary New Age character to the company (for instance, getting the CEO to repeat that WeWork’s mission is “to elevate the world’s consciousness”), causes HR crises through unfortunate statements, or fires employees tyrannically simply because of their “bad energy.”

As a character, Adam Neumann is curious in his own right, and Jared Leto conveys that quality wonderfully. In “WeCrashed”, we see him go from being an entrepreneurial loser who creates laughable companies, such as a foldable heels company for women, to founding the most hyped startup on the planet and reaching a $47 billion dollars valuation. The series shows him making his breakthrough thanks to his great charisma and storytelling ability. Cheerful and optimistic, he was able to enthuse and convince anyone, and he crafted a compelling story about himself: the boy who was happy living on a kibbutz and then came to individualistic New York, coming up with the idea of shared spaces with a sense of community where you can “do what you love.” However, he also comes off as someone who lied his way through success, was thoroughly irresponsible, and eventually took the “fake it till you make it” mantra just too far.

The series covers the entrepreneurship culture at the highest level. It is certainly interesting to see how Neumann went from drinking beer with his employees to flying a private jet to supervise and rush the expansion of WeWork in China, Norway, Peru, and other corners of the world, fueled by the funding of over 4 billion dollars from the SoftBank’s legendary investor Masayoshi Son, whom Neumann managed to persuade with charisma, storytelling, and a dash of madness.  

So, how close is WeCrashed to the facts? It appears to be the most ill-intentioned of the three series and the one that fictionalized the facts the most. From an interview with Adam Neumann a few months ago, we learned that he finds it unfair to have a series made using his full name without even considering his version of the story. He has a point.

WeCrashed is based on a podcast of the same name, which would not exist without the book “The Cult of We”, by Eliot Brown and Maureen Farrell, the journalists from The Wall Street Journal who exposed the company’s financial disaster. Before the premiere of “WeCrashed,” both Hulu and HBO had chronicled Neumann’s downfall in documentary format.

The Dropout: Theranos’ incredible fiasco

Despite Theranos being the most incredible and dirty case, “The Dropout” as a show is conventional and somewhat flat. It is better at the beginning, when it features a character study of Elizabeth Holmes, going through her childhood, her family life, her adolescence, and the years she spent in college studying chemical engineering. We see her obsession with becoming a billionaire changing the world, à la Steve Jobs, her ultimate hero. An obsession that, as we know now, ultimately led her not only to lower her voice, dress always the same clothes and other eccentricities but also to commit the most spectacular fraud of recent years.

After this initial part, “The Dropout” veers into more predictable territory, especially if you are already aware of the Theranos case, which is the one with the most media coverage. In all these boom-and-bust stories, we know what will happen beforehand but we watch them anyway because the journey is enjoyable. However, and despite how powerful and unusual the real-life events were, The Dropout’s journey is the least exciting. Furthermore, Holmes’ relationship with Sunny Belwani, a businessman she placed in a high position at Theranos while hiding he was her longtime love partner, doesn’t come off as very convincing.  

Weak as this may sound, “The Dropout” does have its moments. The series takes off when The Wall Street Journal reporter John Carreyrou enters the scene. Alerted by sources that pointed out that Theranos and its promise to diagnose diseases with a drop of blood was a lie, he decided to investigate. This is a high-tension episode, at the level of great investigative journalism films, and one that vindicates the role of the media, which had swallowed Holmes’ story for years—hook, line, and sinker—featuring her on magazine covers and presenting her as a symbol of female empowerment.

Interestingly, Rupert Murdoch, the newspaper’s owner, is also vindicated for letting the story run despite having recently invested $125 million in the company (real-life spoiler: he lost almost all of it). John Carreyrou’s article ultimately ended up sinking Theranos. He then turned it into a book, “Bad Blood“. Without it, there would be neither the documentaries about Holmes (one on HBO) nor the podcast on which the series is based, also entitled The Dropout.