Steve Jobs on various device screens

Marysia Machulska

Steve Jobs’s Complex Legacy

Note: This is the second installment in a two-part series about the author's binge of streaming shows focusing on Silicon Valley startups and their founders. You can read the first entry here.

On the third day of binge-watching Super Pumped, The Dropout, and WeCrashed, I looked forward to a story that didn’t end, as it did for Elizabeth Holmes and Theranos, in a criminal conviction and a company’s implosion. On the contrary, I was relieved to discover that the final lap of my journey—eight episodes of WeCrashed over 12 more hours—involved two characters who seemed less likely to blast subordinates or bilk investors than to stumble out of the back of the Scooby-Doo van.

These characters—Adam Neumann, a cofounder of the workspace-sharing giant WeWork, and his wife, Rebekah—are first presented in Apple TV’s production as a couple of vicuña-clad hippies. A liveried servant invites Adam to begin his day with a toke from a cobalt-colored bong, while Rebekah confers with an interior decorator about her airplane hangar of a kitchen where, much to her dismay, “the feng shui is off.”

Just as it had for the first two entries in my streaming-series marathon, the ghost of Steve Jobs seems to hover over WeCrashed. As Walter Isaacson recounts in his best-selling biography, Jobs, much like Adam and Rebekah, had a penchant for lifestyle fads and woo-woo mysticism that Hollywood at once likes to parody and embrace. In his teenage years, he grew his hair long, dabbled in Eastern religion, and commenced a lifelong habit of eating only certain foods, typically fruits or vegetables, for unusually long stretches of time. (“I’m a fruitarian,” one friend told Isaacson, poking fun at Jobs’s dietary pronouncements, “and I will only eat leaves picked by virgins in the moonlight.”)

Because of his plant-based diet, the young Jobs assumed that he didn’t need to wear deodorant. (Follow the logic? Neither do I.) And the repeated suggestion that he smelled a little odd did nothing to dent this conviction. Don Valentine, an early investor in Apple who first met Jobs when he was assigned to the night shift at Atari (a consequence of his distinct aroma as well as his tendency to call coworkers “dumb s——ts”), told Isaacson that Jobs’s “wispy beard” and skeletal appearance made him look like Ho Chi Minh. His conclusion: “Steve was trying to be the embodiment of the counterculture.”

The verdict is a reminder that, while we typically think of him as an austere prophet of a technosaturated future, Jobs was a child of the ’60s. Born in 1955, he spent his teens in the Bay Area, and while the politics of the flower power era never seemed to make any abiding impression on him, he embraced many of the cultural proclivities that attended it: a search for elevated consciousness and mystical engagement beyond the familiar portals of the Judeo-Christian tradition, the adoption of exotic medicinal regimens and novel dietary practices in pursuit of that fugitive abstraction “health and wellness,” and a disdain of materialism and moneymaking (explicit in speech, if often ambivalent in practice).

The algorithmic sensibility of Silicon Valley and the metaphysical adventurism of the ’60s counterculture might seem like strange bedfellows—computers run on complex operating systems not crystal power—but Jobs was part of a small band of technophiles who regarded advancements in computing as conducive to the aims of self-actualization. In his 2005 commencement address at Stanford—as much a touchstone for his legacy as Isaacson’s biography—Jobs recalled the Whole Earth Catalog, a magazine published in his youth whose slogan promised “access to tools” that would empower self-sufficiency among its ecologically minded readers. “It was sort of like Google in paperback form,” Jobs told the graduates of what he implausibly called “one of the bibles” of his generation. “It was idealistic and overflowing with neat tools and great notions.”

Practically speaking, Apple shared that aim. By putting a personal computer into the hands of every man, woman, and child, Jobs hoped to provide users a world of ideas as well as the virtual tools to exploit them. “We are inventing the future,” he told Bill Atkinson (according to Isaacson) when Jobs tried to persuade him to leave grad school and join the company. “Come down here and make a dent in the universe.”

The power of personality

As WeCrashed makes clear, the Neumanns share Jobs’s propensity for grandiose pronouncements. “Our mission is to elevate the world’s consciousness,” Adam tells a business journalist in the fourth episode. When the journalist asks how exactly WeWork might accomplish this task, Rebekah interjects, “By living proactively and with purpose. By being a student of life, for life.”

Throughout the series, Rebekah and Adam are a font of New Age inanities, a reflection of the couple’s real-life penchant for celebrating themselves and the seemingly limitless possibilities of a workspace-sharing company. As the Wall Street Journal reported, Adam proposed that WeWork could one day “solve the problem of children without parents” and end world hunger. Then he might pursue other goals he openly contemplated: running for president of the world, living forever, and becoming the first trillionaire.

Rebekah’s musings were somewhat more restrained. She proffered pseudoscientific dietary tips, such as the notion that the energy of sad animals will make you sad when you consume them. She claimed on WeWork’s corporate website that she had studied under “His Holiness the Dalai Lama and Mother Nature herself.” And she seconded her husband’s unusually expansive vision of WeWork’s mission. Her most notable addition to the company’s portfolio, WeGrow, was a venture that aimed to educate young children in subjects typically omitted from a grammar-school curriculum, such as meditation, farming, and entrepreneurship. (“In my book, there’s no reason why children in elementary schools can’t be launching their own businesses,” she told Bloomberg.)

The story of American capitalism over the past decade has been a celebration of excessively grandiose ambitions.

In the corporate world, such preposterous behavior is often tolerated by those who know better but have every incentive to keep their mouths shut. This was certainly the case for the early investors and employees at WeWork when the company was growing by leaps and bounds. But even beyond giving everyone involved good reason for embarrassment, such conduct is problematic in that it both mirrors and emboldens a self-conception that confuses superior skills and some measure of success with uncanny abilities and providential appointment. Adam Neumann shared Steve Jobs’s habit of parading around the office barefoot as if he were indeed the Dalai Lama, but he also adopted the unnerving custom of staring at people intently in the middle of conversation. “He laser-beamed in on you and didn’t blink,” former Apple CFO Debi Coleman said of Jobs. The upshot of that tendency? “It didn’t matter if he was serving purple Kool-Aid. You drank it.”

Colleagues made similar observations about Neumann. “When you’re in a room with Adam, he can almost convince you of anything,” a WeWork employee told Vanity Fair’s Gabriel Sherman in 2019. WeCrashed showcases Neumann’s Svengali-like powers of salesmanship, which famously included convincing SoftBank’s technology-focused Vision Fund to eventually invest more than $17 billion in WeWork, even though the company was hardly a conventional tech play. “I call it ‘space as a service,’” he tells Masayoshi Son, the billionaire founder of SoftBank, in an effort to frame WeWork as a SaaS venture. “We’re building data systems to connect communities around the world.”

When it comes to such immense powers of personality, whether they are a blessing or a curse depends very much on what’s in the Kool-Aid. In Jobs’s case, his charismatic persuasiveness drove people around him to create products—the Macintosh, the iPhone, the iPad—whose elegant minimalism and user-friendly interfaces made true believers of a legion of consumers who hardly fancied themselves tech nerds. And yet, the approach he took to developing these goods, combining implacable standards of taste and personal performance with an otherworldly sense of what was possible, led many around him to see a kind of dark energy at work in his willfulness. (Coleman, for instance, compared him to Rasputin.)

Tragically for Jobs, his own sense of how the world was supposed to be—as well as, perhaps, his own indispensable place within it—were so adamant that they proved his undoing. When he was first diagnosed with a treatable form of pancreatic cancer in 2003, to the horror of intimates, Jobs delayed getting surgery, hoping to alleviate his condition with a series of remedies that might charitably be called “alternative medicine”—herbal therapy, acupuncture, a vegan diet that emphasized carrot and fruit juices, and even the consultation of a psychic. His friends implored him to have the tumor removed, but for nine months, Jobs was unbending. “I think Steve has such a strong desire for the world to be a certain way that he wills it to be that way,” one friend told Isaacson. “Sometimes it doesn’t work. Reality is unforgiving.”

It certainly is. Jobs died of cancer in 2011 at the age of 56.

The price Adam Neumann paid for his own preternatural sense of certainty was hardly so high. Like Jobs, he could bare his fangs when his will was being thwarted. (In the fifth episode of the series, he tells a competitor who refuses to sell out to him: “I’m going to crush you. I’m going to destroy your business and your soul.”) But for the most part, the pleasure of WeCrashed is watching two people get high on their own supply and vigorously pursue their downfall.

The pageantry of absurd self-importance reaches its zenith in the penultimate episode, when Adam accepts Rebekah’s offer to rewrite the S-1, the filing any company must make with the Securities and Exchange Commission when it intends to go public. Her infamous additions to the document, which began with the unusual declaration, “We dedicate this to the energy of we—greater than any one of us but inside each of us,” led New York University’s Scott Galloway to liken the filing in a Hulu documentary about WeWork to “a novel written by someone who was shrooming.”

Even beyond the psychedelic prose, however, the most remarkable innovation in WeWork’s S-1 was the stipulation that, in the advent of Adam’s demise, Rebekah would have the right to choose his successor, a prerogative that was greeted exactly as one might expect by WeWork’s board members.

“This is about to be a public company, not a monarchy,” one patiently tries to explain to Adam in the final episode of the series.

“Ahhhh, but it is like a monarchy,” Neumann says. “My family is the moral compass of this company.”

The board member persists. “See, you have to stop saying things like that.”

Adam Neumann didn’t, neither in the series nor in real life, not until an initial public offering whose potential value had been estimated as high as $96 billion crumbled under the weight of his antics. Shortly thereafter, Adam was forced out of the company he founded, wearing a golden parachute worth more than $1 billion, and when WeWork finally went public in 2021 via a special purpose acquisition company, or SPAC, it was valued at just $8 billion.

Today, the company flirts with bankruptcy.

Mother Teresa meets King Midas

Near the end of the final episode of WeCrashed—which I finished shortly before midnight, two-and-a-half days after my television odyssey began—Cameron Lautner, a fictional character who has been brought in to take over WeWork after Adam Neumann’s ouster (in reality, two men assumed that role) delivers a speech that is by turns a cold shower and a cri de coeur for the shell-shocked staff at headquarters. “Like a magician,” he says, referring to his predecessor, “he’s tried to perform a sleight of hand over the entire financial world, crafted an illusion that you all were part of something bigger. What were you gonna do, raise the world’s consciousness, solve world hunger, care for all the world’s orphans? Excuse me, how the f——k is a shared-workspace company supposed to do any of that?”

He continues: “So I think it’s about time we got really honest about what we actually do here. We’re not here to raise the world’s consciousness. That’s not how capitalism works. We’re here to earn value for our investors, and we’re going to do that by providing high-quality shared workspaces at a competitive price. And what are you going to get in return? A fair wage and real profit sharing.”

The address is met with modest applause, a marked departure from the all-hands orations routinely delivered by Neumann. As a cinematic choice by the creators of WeCrashed, the lukewarm reception isn’t surprising. The story of American capitalism over the past decade has been a celebration of excessively grandiose ambitions, a spirit of “the sky’s the limit,” not “steady as she goes.” This is especially true of Silicon Valley, where it is not enough to get filthy rich; you must change the world while you’re at it.

Such world historical ambitions, a kind of “Mother Teresa meets King Midas” complex, helps to distinguish the Adam Neumanns of the world (and the Travis Kalanicks and Elizabeth Holmeses) from the aspiring alpha dogs of high finance. For whatever criticisms one might have of that second lot, a knack for self-deception isn’t among them. Investment bankers and hedge fund managers tend to be crystal clear about the measure and mission of their profession—to make as much money as possible. And though they may occasionally make a nod to “social purpose,” for the most part these gestures are not so much an afterthought as a fig leaf and a feint.

“It’s all about bucks, kid,” Gordon Gekko tells his protege in Wall Street. “The rest is conversation.”

By contrast, the conceit of the “make a dent in the universe” mantra is that the ambitions of an entrepreneur don’t end in a payout or even some great product. They are sociopolitical, teleological, or existential in nature. Less practical endeavors than the labors of enlightenment, such ventures are the stuff of consciousness-raising meets creative destruction, undertakings bold enough to scorn the trifling constraints of case law and cosseted inclinations of middle-class morality. Forget filthy lucre—the stakes are so much bigger!

That such pretensions are often met with an eye roll and a chuckle is one reason all three shows are so thoroughly entertaining, though they also recall the French philosopher Henri Bergson’s gem, “In laughter we always find an unavowed intention to humiliate, and consequently to correct our neighbor.” If we find ourselves laughing at the characters in Super Pumped, The Drop Out, or WeCrashed, the correction intended is not to the belief that a ride-sharing service or a blood-testing device or a workspace-sharing company will change the world—they will not, not in any deep and abiding way, no more than an iPod—but to the license so often assumed by the adherents. For if one does indeed aim at nothing less than revolutionizing the world around us, what’s wrong with a little cruelty, a few lies, and a dash of self-aggrandizing kookiness?

The complex legacy of Steve Jobs, which includes some truly extraordinary accomplishments, raises such a question—just as those who show their immense admiration for him by drawing on the worst elements of his character plainly answer it.

John Paul Rollert is adjunct associate professor of behavioral science at Chicago Booth.

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