“I’m gonna change the world!” screams the company founder. She’s streaking through the streets of Palo Alto in her older boyfriend’s luxury car, high off the nine figures of funding she’s just secured for her new Silicon Valley start-up.
“What is the company’s role?” asks another founder’s wife. She’s talking to a crowd of hundreds of employees, gathered for a weekend-long rager on their workplace’s dime. Her answer: “Nothing less than elevating the world’s consciousness. And by doing that, we will make a better world together.”
“I build great companies. Companies that change the world,” says the venture capitalist to—you guessed it—yet another founder. He’s concerned about the direction of the company he’s invested not just his money in, but also his attention and time. “Relying on people’s worst, most base instincts is not a way to change the world.”
These are three different quotes from three different shows based on three different true stories—all set to premiere, starting this Sunday, within three weeks of one another. Their similarities speak to a common theme that emerges when you talk about American capitalism in the 21st century, especially its most influential sector. In terms of industries disrupted, fortunes made, and cachet acquired, technology is the great business story of the past 20 years. But with such a meteoric rise comes the possibility of an equally dramatic fall.
Boom-and-bust cycles are nothing new, of course. Seventeenth-century Holland had tulip mania; 19th-century America had the Gilded Age, now dramatized on HBO; the current craze around non-fungible tokens has spawned a backlash that contends that they, too, are a house of cards. What’s unique about this most recent epoch is the deeply held conviction—by founders, funders, the media, and tech culture writ large—that for-profit companies are a vehicle for positive social change. It’s an era we appear to be leaving, with a trio of glossy new series forming a collective eulogy.
Over the weekend, Showtime will premiere the first episode of Super Pumped: The Battle for Uber, adapted from New York Times reporter Michael Isaac’s book of the same name. Next week, Hulu will debut the first three episodes of The Dropout, based on the ABC News podcast hosted by journalist Rebecca Jarvis. And on March 18, Apple TV+ will enter the race with WeCrashed, also drawn from a narrative podcast. Each centers on the parabolic arc of a notorious start-up chief: Travis Kalanick, the cofounder of Uber ousted from his role as CEO in 2017; Elizabeth Holmes, the Theranos founder recently convicted on four counts of fraud; and Adam Neumann, the Israeli entrepreneur who left WeWork in the aftermath of a disastrous, failed IPO.
There are key distinctions that separate these stories from one another. The blood-testing device that Theranos claimed to manufacture was never truly functional, whereas Uber and WeWork provide a real, if dubiously profitable, service. Holmes is a woman, a simple fact that affected her trajectory in subtle, complex ways; Kalanick is a chauvinist who created a company culture in his image. (WeWork is a fascinating middle ground, a company effectively co-led by a married couple that had its own problems supporting female employees.) And while Holmes and Theranos remained synonymous until their mutual demise, Neumann and Kalanick are the rare founders who were actually deposed from their successful companies—though in a money-saturated system that gives founders enormous power, they’ve gone down as a couple of exceptions that prove the rule.
But there’s also plenty that unites the series, both as true events and fictionalized retellings. All three cast movie stars as the central characters, continuing a recent sea change in TV that neatly reflects the individualistic, founder-centric norms of Big Tech. Joseph Gordon-Levitt, fresh off captaining his own show, plays Kalanick; Oscar nominee Amanda Seyfried plays Holmes, stepping in for Kate McKinnon; Jared Leto plays Neumann, following up House of Gucci with another heavily accented role, with Anne Hathaway as his wife, Rebekah. (Both are Oscar winners.) And all three arrive at a crucial juncture: not just the unofficial start of Emmy season, but the space between an earlier generation of tech tycoons—your Mark Zuckerbergs, your Jack Dorseys—and the next. Before we get the inevitable Bored Ape Yacht Club story, we first have to sort through the wreckage that ensues when you move fast and break things.
“I think we’re at a moment where we are questioning a lot of the stories that these tech companies have been telling us,” says Liz Meriwether, the New Girl creator turned showrunner for The Dropout. “I remember buying into the idea that this was the future, and that the future was going to make everyone’s lives better.”
Meriwether graduated college in the mid-aughts, when Facebook was just taking off, the iPhone first launched, and Elizabeth Holmes dropped out of Stanford to start her company. Now that Theranos has been unmasked and even reputable companies like Facebook are notorious for spreading misinformation, it’s harder to maintain that kind of optimism. “We’ve all gone on a bit of a ride with that idea recently,” Meriwether adds. “Maybe these shows are coming from that place of looking back and asking tougher questions.”
To understand Kalanick, Holmes, or Neumann, it’s helpful to understand the system that enabled them. After all, contrary to the myth these shows’ subjects internalized, Silicon Valley is a collaborative environment — one where success depends on much more than a singular genius toiling away in a garage.
“Essentially, it used to be really hard to raise money, and then it got really easy,” says Casey Newton, a journalist who covers technology via the Substack newsletter Platformer. It’s a straightforward way to sum up a set of overlapping trends, but it succinctly describes the power dynamic that allowed Kalanick to persist through multiple major scandals, or Holmes to brush off scrutiny toward the basic functionality of her core product. When companies stop competing for funding and funds start competing to finance them, it’s easy for things to get out of hand. “You had this situation where there was too much money chasing too few good ideas, but the people who won wound up becoming kings of industry,” Newton adds. Backers were often investing in founders as much as, if not more than, their businesses, creating a disincentive to impose any checks on their power.
In 2010, the same year Kalanick became CEO of Uber and Neumann cofounded WeWork with Miguel McKelvey, venture capitalist Ben Horowitz published a blog post titled “Why We Prefer Founding CEOs.” The essay laid out the philosophy espoused not just by the author’s own firm, Andreessen Horowitz, but also Benchmark, an early investor in both WeWork and Uber: placing trust in founders, as opposed to professional managers, to lead their companies for the long term. (As Benchmark partner Bill Gurley, an ex-athlete from Texas not too far removed from his most famous role, Kyle Chandler is effectively the co-lead of Super Pumped.) Horowitz cites examples from Marc Benioff to Jeff Bezos, but his argument hinges on the de facto deity of modern-day founder worship: Steve Jobs, who exemplified what Horowitz called “the founder’s courage to innovate despite the doubters.”
This ethos didn’t exist in a vacuum. When the dot-com bubble burst in the early aughts, the ensuing chaos led to the ouster of CEOs such as Yahoo’s Tim Koogle, a form of executive upheaval that voices like Horowitz were in part reacting against by announcing their intention to back founders for the long haul. Rising income inequality pooled resources at the upper tiers of the economy, creating an enormous stockpile of money looking for someplace to go. And the rise of Amazon Web Services, paired with the launch of the iPhone in 2007, made tech start-ups relatively cheap and easy to, well, start up—at a time when the mobile phone revolution created a massive demand for new software.
Still, these material factors only amplified an existing mythology, a shared legend whose heroes are now household names: Bill Gates, Larry Page, Sergey Brin, above all, Jobs, who remains the gold standard of a transformational visionary who changed the world by building a trillion-dollar enterprise. “You want to not only start a company, which is one of the best things that a good capitalist can do in the Valley,” says Isaac, the author of Super Pumped. (He also consulted on the show and even makes a cameo as himself.) “You want to use capitalism and company-building to change the world, to make a dent in the universe, to bring consumerism to some sort of higher purpose.” In the minds of many movers and shakers around the San Francisco Bay, Jobs didn’t just do all that; by returning to Apple after a decade away and leading it to world domination, he’s also the ultimate proof that the founder knows best.
Both in real life and in scripted retellings, even infamous founders are acutely aware they’re following in others’ footsteps. Holmes blatantly modeled her wardrobe after Jobs’s; in The Dropout, her teenage bedroom in suburban Houston is decorated with a massive poster of the corporate guru, the way other teens would pin up a spread of their favorite movie star. The Super Pumped version of Kalanick demands a meeting with Page, who’s unimpressed by his lack of coding skills, and refers to Spotify’s leader as “Ek”—last name only, like he’s a fraternity brother. (Disclosure: Spotify owns The Ringer.) When confronted about his rampant spending, Leto’s Neumann is indignant: “You know who else has lost money? Amazon. Uber. Twitter. Spotify. Snapchat.” They’re not aware of it in the moment, but each is on the way to becoming the worst-case scenario to their idols’ best.
Once venture capital enters the picture, what starts as personal ambition turns into a professional asset. “VC is a business where you have to swing really big,” Isaac explains. “You will lose 99 times out of a hundred. And then that 100th one will make up for all your losses and then some.” In other words, venture capital incentivizes exponential growth and the sharp-elbowed players who promise to deliver it. For better or for worse, extreme personalities produce extreme results. Holmes may have been given to quoting Yoda, but a more applicable reference would be Game of Thrones: ambition and greatness are often two sides of the same coin.
“I used to think they were all Jesus Christ,” says Chandler’s Gurley of the founders he backs. “Then I began to see that half of them were, indeed, on the side of the angels, and half of them were some version of David Koresh.” Now, though? “They’re all Koresh. The trick is to flee the cult and get out of the compound the second before they burn it to the ground.”
All three of these founder shows are firmly rooted in a real-life phenomenon. Still, a wealth of inspiration can be a double-edged sword. Hollywood productions, especially ones made during a pandemic, take a long time to come together. With stories as high-profile as the collapse of a multibillion-dollar company, that means breaking into a crowded field—and arguing your project has something to add to the deafening noise.
Holmes’s saga may be the most overexposed relative to her real-world impact. (There were plans to put Theranos machines in drugstores across the country, but the company thankfully folded before it became widely accessible.) On top of Bad Blood, John Carreyrou’s definitive behind-the-scenes book, there’s also an HBO documentary, the Dropout podcast, and an upcoming Adam McKay movie starring Jennifer Lawrence. WeWork has its own feature-length doc, plus a book by reporter Reeves Wiedeman and longform obituaries in magazines like The New Yorker. Uber and Kalanick may be the least publicized, but there’s still Isaac’s book and—naturally—a podcast to contend with.
“I had the same question,” Meriwether says when asked how the Hulu version of The Dropout would make its mark. Her answer came from what she saw as a gap in the podcast, through no fault of its own. “Because it’s made by journalists, it can’t tell the story from her point of view,” she explains. “Obviously, I can’t be inside of her mind, but I felt like that aspect of the story hadn’t been told yet.”
Holmes is a bizarre, almost inhuman figure of her own invention. The voice! The green juice! The dancing! In their reporting, both Jarvis and Carreyrou largely stick to the facts, letting extraordinary events speak for themselves and shying away from unknowable truths like what Holmes was thinking. But as Inventing Anna learned the hard way, a TV show doesn’t have that option, or else it’s simply a more expensive retread of what’s already been done. The Dropout is certainly of a piece with Super Pumped and WeCrashed, yet it also works as a companion—and corrective—to another story about a sensational scammer. Inventing Anna never presents a cohesive theory of con woman Anna Delvey. The Dropout, and Seyfried’s performance, portray Holmes as brilliant but impatient, and under enormous, self-imposed pressure to succeed. Given some bad advice and worse role models, both personified by COO Sunny Balwani (Naveen Andrews), she ends up charging down the wrong path.
For WeCrashed, adaptation was less about invention than emphasis. A flamboyant huckster who once sold baby clothes with kneepads, Adam Neumann is widely considered the emperor of WeWork who had no clothes. (Almost literally: Neumann infamously never wore shoes.) Less lampooned, and before that celebrated, is Rebekah Neumann, née Paltrow—as in Gwyneth, her cousin. A former yoga instructor and aspiring actress, Rebekah helped Adam transform into a leader, while he helped her realize a yoga empire wasn’t in the cards.
Nothing already published about WeWork “dug into what we saw as the heart of the story,” says Drew Crevello, who cocreated WeCrashed with The Office executive producer Lee Eisenberg. “There is no WeWork without Rebekah Neumann, and there is no WeWork without the very specific alchemy of these two personalities coming together.” Both Adam and Rebekah are presented as comedic characters, but it’s Rebekah who carries the emotional weight. Some pleas for our sympathy are more effective than others. In an uncanny parallel with Holmes, whose father worked at Enron when the company imploded, Rebekah’s dad was also involved with some shady business practices; along with an older brother’s death from cancer, it’s a family history that explains her actions without excusing them. On the other hand, Rebekah starts feeling taken for granted and overlooked as a co-equal partner in a … borderline Ponzi scheme? Like WeWork’s incoherent S-1 filing, which lists Rebekah as Adam’s “strategic thought partner,” it’s a stretch.
For creators Brian Koppelman, David Levien, and Beth Schacter, Super Pumped was well in their wheelhouse. Koppelman and Levien are longtime writing partners and the cocreators of Billions, where Schacter works as an executive producer. Longtime fans of the Showtime drama will find themselves on comfortable terrain with Super Pumped, a fast-talking, testosterone-fueled battle of the wills between two frenemies in a cash-flooded workspace. Super Pumped trades finance for tech and fiction for (augmented) truth, but once Chandler starts waxing poetic about Joakim Noah’s jump shot in an unrelated conversation, the Billions hive will feel right at home. There’s even another Mark Cuban cameo.
“Obviously, there’s some primal question that we keep coming back to [with] these relationships between people where somebody thinks they’re smarter than other people,” Koppelman says. For Super Pumped, he, Levien, and Schacter wanted to enhance a familiar structure with a wider stylistic range. Billions (and Rounders, and Ocean’s Thirteen) is hardly minimalist, but Super Pumped unleashes a full arsenal of fresh devices: Adam McKay–style infographics, animated asides that imitate a video game, and a voice-over by Quentin Tarantino.
“Because it was about disruption, it gave us this freedom to make a show that had a very disruptive feel,” Koppelman explains. “We could use every filmmaking technique that we wanted to.” But of course, one man’s disruption is another’s unrepentant disregard for privacy standards or labor laws. Of the three founders profiled by these new shows, Kalanick is the most objectively successful; he hasn’t been convicted of a crime, nor is his former company underwater. But even Super Pumped is decidedly ambivalent about whether that success is a good thing. If Uber really did change the world, it may not have been for the better.
Ironically, the legend of the tech founder is so outsized that it’s outgrown tech itself. Theranos was never a traditional technology firm; as its downfall would eventually demonstrate, there are reasons why the market doesn’t typically subject biomedical technology to the same growth-over-everything pressures as other kinds of start-up. At its core, WeWork was always in the unglamorous business of subleasing commercial real estate, give or take some West Elm furniture. Even Uber began as a transportation business called UberCab. The concept of a “ride-hailing platform” took root only as a way to get around taxi regulations.
At a certain point in the last decade’s technology boom, the cart began to lead the horse. The archetype of a path-breaking iconoclast shaking up a staid business world came first, with the actual ideas arriving later—or, in some cases, not at all. For storytellers, that gap between expectations and reality leaves ample room to explore. “What I thought was really fascinating about the story of Theranos is that she was taking this relatively new culture of tech companies and she was applying it to the hard sciences,” Meriwether says. “And ultimately, at the end of the day, the human body is not a machine.” The Dropout shows the process of trying to fit a round peg into a square hole, condensing the slow, halting pace of scientific progress to meet the demands of a hype-driven landscape.
Founders like Holmes and Neumann pursued the tech-adjacent model in part because it’s worked before—something Hollywood, itself an industry in the throes of disruption, knows all too well. Netflix has long billed itself as a tech company that just happens to produce, market, and distribute entertainment, a strategy that worked well for its share price before some recent pitfalls. Then there are the actual tech companies expanding into entertainment, among them Amazon and Apple. That’s one of the more amusing aspects of watching WeCrashed: All three shows make at least some reference to Steve Jobs, but only it occupies a small room in the very house he built.
“That’s one of the things we have fun with in the show: this reframing of the company as a tech company that is not really a tech company,” Crevello says. “They rented office space; they rented desks,” Eisenberg adds, laughing. “At the end of the day, it was just a nice, comfortable place to work.” Given that Hollywood itself is in the illusion business, it may be uniquely qualified to deconstruct the illusions of others. In a memorable scene from WeCrashed, Neumann latches onto the common term software as a service and gives it his own spin: space as a service. It’s a meaningless phrase with the sound and feel of something more substantive, just like WeWork.
Shows like Super Pumped, The Dropout, and WeCrashed suggest we’re well into the backlash against hubristic founders and the naive assumptions that helped empower them. The Social Network may have skewered Mark Zuckerberg more than 10 years ago, but the film was more an indictment of one unscrupulous actor than the product he unleashed, or the structure that keeps him in firm control of Meta via Class B voting shares. This latest wave is more sweeping, and it isn’t over: HBO is currently developing a limited series starring Claire Foy as Sheryl Sandberg.
But even as disillusionment with one era of unsustainable growth gets a slew of prestigious, star-backed illustrations, another may just be getting started. What apps and mobile computing were to one wave of next big things, the metaverse and cryptocurrency are to our current one. One could speculate that the crypto boom will spawn its own surge of satires, but that’s no longer a hypothetical: A young couple who prosecutors say laundered billions of dollars in stolen crypto recently spawned three potential projects in less than a week.
“It’s fucking insane how much money is going into crypto,” Isaac observes. “And crypto is either a transformative, next-generation version of what the internet’s going to look like, or a giant scam and a bunch of people are going to get fleeced.” There are also plenty of options between those binary outcomes. The same micro-generation that yielded still-thriving disruptors like Airbnb also gave us empty charades like Theranos, or even embattled but still-standing players like Uber; there’s no reason their successors won’t pan out along the same lines. “I still have Uber on my phone,” Schacter points out.
The very existence of shows like Super Pumped is itself a sign that we’re at a point of transition. “The metaverse, crypto, and Web3 is where all the useful energy is right now,” Newton says. “It feels like the end of a chapter. And I think that, combined with the fact that everyone loves a good rise-and-fall story, is why you’re seeing some of these filmmakers come in and be reflective about that time.” In an industry that prides itself on innovation, it’s often hard to predict what’s around the corner. All we can do in the meantime is sort through the recent past, one spectacular meltdown at a time.