Academics move at their own pace, often defiantly so. For months I was pestered by friends for a business ethicist’s opinion of the streaming service triumvirate—Super Pumped, The Dropout, and WeCrashed. A smorgasbord of schadenfreude drawn from the pages of the business press, all three shows debuted in spring 2022 and were widely acclaimed for exposing Silicon Valley excess by savaging the founders of Uber, Theranos, and WeWork, respectively.

Bankers might be inclined to ask what took Hollywood so long. For decades, it has found ample excuse to interrogate the culture of high finance—Wall Street (1987), Boiler Room (2000), American Psycho (2000), Margin Call (2011)—and the conclusion has consistently been that enviable success requires participants to sell their souls, or at least a raft of crummy securities.

Comparatively speaking, the tech sector has gotten off easy. Before the recent season of television, the most noteworthy illustration of “bad business” in Silicon Valley was The Social Network (2010), David Fincher’s darkly comical account of the litigious origins of Facebook. It’s a splendid movie, but its strength as an exercise in storytelling comes at the price of its potential for social commentary. The film tells a fairly conventional tale of sophomoric striving and human frailty. An awkward and unlikable young man lies, cheats, and casts aside old friends in pursuit of being cool. But the movie’s portrayal of Mark Zuckerberg is ultimately too idiosyncratic and ad hominem to be a cautionary tale about the tech sector. “Zuck” is simply a weirdo who buries his face in code and backs into a billion-dollar company.

This is not a failure of Fincher nor of the movie’s silver-tongued screenwriter, Aaron Sorkin. In addition to the fact that agitprop rarely makes for enduring art, when The Social Network debuted, the wunderkinds of the tech world represented a welcome alternative to the wolves of Wall Street. This apple-cheeked army of hoodie-wearing overachievers would “bring the world closer together” (in Facebook’s mission statement) by building new networks of relationships, expanding the global reach of e-commerce, and filling our pockets with “apps.” They would prove that the newest, most exciting, and, yes, most lucrative frontiers of capitalism could be fully explored while still keeping faith with Google’s famed credo: “Don’t be evil.”

Oh, what a difference a decade makes.

Today, the tech sector is synonymous with emotionally maladroit leaders who vacillate between sketchy marketing, self-mythologizing humbug, and the tendency to regard as a mark of genius what is in reality nothing more than a mean streak. Such traits serve as themes for Super Pumped, The Dropout, and WeCrashed, something I discovered when I finally set aside time to watch them. I embarked on a 24-hour pilgrimage of programming spread over three consecutive days, a vast plain of “prestige television,” and as I made my way across it, episode by episode, one name, like a natural wonder, slowly rose into view: Steve Jobs.

Moving violation

Steve Jobs died in October 2011, nearly a year after The Social Network arrived in theaters and only a few weeks before the biography he authorized and collaborated on was published. That book, Walter Isaacson’s Steve Jobs, was a worldwide sensation, eventually selling more than 3 million copies in the United States alone. Among its readers appear to have been Elizabeth Holmes, Travis Kalanick, and Adam Neumann—the founders of Theranos, Uber, and WeWork. If their on-screen depictions are at all accurate, each seems to have been inspired by the Apple founder’s spiky personality and shamanistic persona.

I spent the first day of my journey with Kalanick, watching all seven episodes of Super Pumped, the Showtime series based on the eponymous book by New York Times technology reporter Mike Isaac. In the opening scene, the show depicts Kalanick posing a question that establishes the tone of the series as well as the moral conundrum at its heart.

“So you want to work for Uber,” Kalanick says to a potential hire. “I have one question for you. Are you an a——hole?”

Now, if you’re thinking, Oh, thank goodness. This young man wants to make sure that only the best people work at his company!—well, you’re half right. Kalanick does want only the best people working at Uber. Unfortunately, he believes that being an a——hole is a prerequisite for such excellence. “That’s the right answer,” Kalanick says when the job applicant answers in the affirmative, “because if you’re not, you’ll never make it at Uber.”

Chief among the traits Holmes takes on from Jobs is his legendary reality distortion field.

By all accounts, Steve Jobs was a legendary a——hole. “He was an enlightened being who was cruel,” Chrisann Brennan, the mother of his first child, told Isaacson. “I think the issue is empathy,” said another former girlfriend, Tina Redse. “The capacity for empathy is lacking.” Isaacson, who spent hundreds of hours with Jobs in the final years of Jobs’s life, saw things differently. “When he hurt people, it was not because he was lacking in emotional awareness,” he wrote. “Quite the contrary: He could size people up, understand their inner thoughts, and know how to relate to them, cajole them, or hurt them at will.”

Hurt them at will. Coming from a fairly sympathetic biographer, that’s quite the statement.

Jobs did not deny his sadistic bent—“This is who I am,” he replied, when Isaacson confronted him—but as the biography makes clear, Jobs regarded cruelty as a whip he could snap to drive out the insufficiently talented from among Apple’s ranks and brutally inspire the rest. (Jobs had something of a Manichaean view of management, Isaacson believed. He regarded the work of people around him as “either ‘the best’ or ‘totally shi——y.’”)

The willingness to upset people and established practices is captured in one of Jobs’s most famous maxims, “It’s better to be a pirate than to join the Navy.” As early Apple engineer Andy Hertzfeld explained it, “Being a pirate meant moving fast, unencumbered by bureaucracy and politics.” He continued, “It meant being audacious and courageous, willing to take considerable risks for greater rewards.” It also meant slitting a throat or two when needed and engaging in a little plunder. (Steve “never minded occasionally stealing good ideas from others.”)

Rules don’t apply to pirates, or at least they don’t recognize them. Uber’s Kalanick didn’t. Much of Super Pumped involves him scheming to sidestep rules of some sort or other—moral, legal, or merely contractual. Whether it is in his directing Uber’s engineers to find ways to block officials attempting to enforce laws designed to keep the company’s drivers off the streets, or brazenly violating the terms of Apple’s App Store to identify individual iPhone users, or simply idealizing outrageous behavior (“It’s not really illegal if the laws are bulls——t in the first place.”), Kalanick embodies the description of Jobs provided to Isaacson by Apple’s longtime chief design officer, Jony Ive: “The normal rules of social engagement, he feels, don’t apply to him.”

In the sixth episode of Super Pumped, Anthony Levandowski, the former head of Google’s self-driving car project whose company Uber purchased, puts the matter more crudely. “These f——king people, holding me and Travis to this standard like we’re average, like those standards apply,” he says. “People like me and TK, we have the ability to make the world better, and applying conventional morality to the world’s most brilliant minds is insanity.”

Insanity, indeed.

In real life, Levandowski ultimately pleaded guilty to stealing secrets from Google and was sentenced to 18 months in prison, while Kalanick, much like Jobs before him, was pushed out of the company he founded when his board of directors got tired of cleaning up after their Übermensch.

A bloody mess

I finished the final episode of Super Pumped at 2:28 in the morning. Just over 10 hours later, I started The Dropout. Based on Bad Blood (2018), the best-selling book by former Wall Street Journal investigative reporter John Carreyrou, the Hulu series revolves around Elizabeth Holmes, the Stanford dropout and tech sector CEO who most overtly endeavored to channel Steve Jobs.

Jobs was a hero to Holmes. She kept a photo of him in her office, referred to her faulty blood-testing device as “the iPod of healthcare,” and even adopted the uniform of a jet-black turtleneck as an homage to the mock turtleneck Jobs commissioned from the Japanese designer Issey Miyake. (Holmes wore it for cover stories in Forbes, Fortune, and Inc., the last of which was titled, “The Next Steve Jobs.”)

Jobs was famously attuned to the impression made by his products as well as his person. It was a tendency that, to some, was an unwitting reflection of the fact that, for a man who was synonymous with Silicon Valley, he seemed to have little interest in benchwork. “Steve didn’t ever code,” Apple cofounder Steve Wozniak said of his colleague and frenemy. “He wasn’t an engineer and he didn’t do any original design, but he was technical enough to alter and change and add to other designs,” Business Insider reported.

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If “Woz” was being uncharitable—Jobs briefly worked as a technician at Atari after dropping out of college—it is true that Jobs’s genius lay not in building new technology from the ground up but in ensuring that user-friendly design elements and sleek packaging were hallmarks of the final products.

The extraordinary success of such efforts at Apple led Jobs’s friend, Oracle founder Larry Ellison, to remark to Isaacson that Jobs “created the only lifestyle brand in the tech industry.” And when it came to brand management, Jobs was as particular about how he came across to the general public as he was about the launch of the latest iPhone. “He seemed more a showman than a businessman,” former Apple CEO John Sculley told Isaacson. Jobs lured Sculley away from PepsiCo in 1983, only to be famously forced out of the company he founded by Sculley, who felt of Jobs that “every move seemed calculated, as if it were rehearsed, to create an occasion of the moment.”

The instincts for careful brand management and constant calculation are central to the Elizabeth Holmes we meet in The Dropout. The series portrays her as being in a protracted audition to be the next Steve Jobs. Isaacson’s biography served as both a sacred text and a how-to manual for Holmes. According to Carreyrou, employees at Theranos “could pinpoint which chapter she was on based on which period of Jobs’s career she was impersonating.”

Chief among the traits Holmes takes on from Jobs is his legendary reality distortion field. As Hertzfeld described it to Isaacson, “The reality distortion field was a confounding mélange of a charismatic rhetorical style, indomitable will, and eagerness to bend any fact to fit the purpose at hand.” Jobs applied this sense of uncanny conviction to due dates and design details as well as to all sorts of things he decided were not merely possible but certain. “There can be something he knows absolutely nothing about,” Ive recalled, “and because of his crazy style and utter conviction, he can convince people that he knows what he’s talking about.”

In The Dropout, Holmes possesses the same reality-bending resolve, though she’s more ham-fisted in her willfulness. (The show includes a paperweight with the inscription “What would you attempt to do if you knew you could not fail?” Holmes famously placed it, facing her, on her desk.)

Unfortunately, when the promise of her groundbreaking blood-testing technology so consistently comes up short—like Jobs before her, Holmes is hardly an engineer—what she attempts to do is supplement the will to believe with sleight of hand. In the second episode of the series, an early prototype refuses to process results. Rather than call off an imminent presentation to a potential blue-chip client, however, Holmes pushes ahead. The machine is quickly reprogrammed to give the impression of an instant diagnosis of a drop of blood, but the demonstration is entirely, 100 percent fake.

“It’s going to work,” she later assures herself. “It just didn’t—that day.”

In a reminder that the most significant corporate misdeeds are matters of collaboration and a promiscuous spirit of permissiveness, one of her engineers defends Holmes’s deception to a skeptical colleague. “When we get the box to work, we’re not even going to remember this,” he says. “We’ll be geniuses, and you’ll be able to tell this story at a conference wearing flip-flops.”

He concludes: “This is how it works.”

“It,” of course, is the ethic of “Fake it till you make it” that is the stereotypical story arc of Silicon Valley success and the engine of entrepreneurship more generally. There is the spark of it in Jobs’s reality distortion field, though its strength was so considerable precisely because, like the greatest showman-cum-salesman, Jobs didn’t know he was faking it. (“He can deceive himself,” Bill Atkinson, an early engineer at Apple, told Isaacson. “It allowed him to con people into believing his vision, because he has personally embraced and internalized it.”)

Holmes’s deception included fake machines, fake numbers, and, most alarmingly, fake test results. As The Dropout makes plain, the upshot of such chicanery is that Holmes was less Jobs’s protégé than his doppelgänger, a cautionary tale for the corporate world about what happens when style overwhelms substance, sleight of hand becomes simple fraud, and reality proves a brick wall.

“Do you have any idea of what you did?” the general counsel for Theranos incredulously asks Holmes near the end of the final episode when it appears she has no sense of the harm she’s done.

“I was trying to help people,” Holmes explains. “Ultimately, the healthcare industry just was not ready for real innovation.”

The lawyer corrects her.

“You hurt people,” she says, repeating the verdict over and over again, trying to pierce Holmes’s reality distortion field. It proved impenetrable, much like it did for the man Holmes so desperately hoped to emulate.

John Paul Rollert is adjunct associate professor of behavioral science at Chicago Booth. He is recounting his three-day streaming binge over two issues, so look for the conclusion in our Winter 2023/24 issue.

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