Winners Take All: The Elite Charade of Changing the World

by Anand Giridharadas

  When Leibrock asked about Jacobs’s work, she knew to choose her words carefully: “Tell me about your—you’re being paid for something. What’s your job, or jobs?”

  Jacobs said she worked at a corporate massage chain and freelanced for extra money. “So I’m pretty much working every day for the rest of my life,” she said. She explained how she usually got twenty-six to thirty-two hours a week at her job. Besides that, she went to people’s houses for private sessions or went to gyms; they didn’t pay her, but she was allowed to keep the tips.

  Every month she went slightly crazy when money was running out, bills were due, and she hadn’t made enough. She felt like “I’m about to go a little insane and pull out my hair. That’s when I’m like desperate, going everywhere I can, just to find people to rub.” She added, “It’s usually around the twenty-seventh, because that’s when my credit card bill is due. The minimum payment is about $90 at the moment. So that’s when I freak out.”

  Jacobs explained the details of how she got paid. She explained how, like so many American workers, she bore much of what was once properly considered a company’s risk. If the company was able to secure many massages for her, she could make $18 an hour or so, excluding tips. If the company didn’t get a lot of bookings, her pay dropped to minimum wage and her hours might be cut back—the way so many Americans were now employed. In some two-week pay periods, she had made $700; in others, she had made $90.

  It was all adding up lately—the forty-four-mile commute; the old debt she was paying down for her husband, Greg, a part-time delivery driver for a Red’s BBQ who was studying at California State University, Channel Islands; her own bruised credit score, thanks to the $3,700 of massage school tuition that she still owed on her credit card; the dog who needed to be fed. She described this confluence of things as “suffocatingly stressful.” She said, “It’s coming apart a little,” before wandering into her own thoughts.

  “I don’t deal very well with a lot of stress,” she said a moment later, “because I’m anxiety bipolar, so I go immediately to straight full stress, and then I have a panic attack.”

  Jacobs got the attacks when she thought of money—what was due, what was coming in. When an attack came on, she got a jolt to her gut—“like you’re about to get into a car accident.” It felt, she said, like a bear hug from someone you don’t want hugging you. (It happens that one of the founders of Even had been put on the path of starting the company by reading an article in the journal Science, “Poverty Impedes Cognitive Function,” about how the thought of money can be psychologically damaging when you are poor. The study found that going up to poor people in a mall and asking them a hypothetical question about money, such as whether to make an expensive repair to an imaginary car, could drop their IQ on a subsequent test by 13 points relative to people of similar means not reminded of money, a plunge comparable to the effect of being an alcoholic or losing a night’s sleep.)

  Jacobs went on, “So I have to try to get medication, but the medication, it is $60 a month.”

  Leibrock asked how Jacobs imagined a healthier, more satisfying life might be.

  “I would think it’s more inspiring to have a stable income. Just to go outside and go see a movie without having to debate for an hour whether it’s worth it,” she said. “Should we just go get a thing of ice cream and watch something on Netflix instead? Or should we actually have a date night? I mean, we haven’t had a date night in probably a year and a half, to be honest with you. We’re always inside, and we’re never going out with friends, because we can’t afford it.”

  Jacobs and her husband used to shop at Walmart, but in leaner times they had downshifted to the Dollar Store. They were both putting on weight with the new food. The high salt and sugar content in the cheap, processed items they were buying was getting to her. She was convinced that the food was responsible for the ache she now felt in the mornings getting out of bed.

  Jacobs came from that other America whose residents’ lives had grown more and more insecure in the years of Silicon Valley’s ascendancy—117 million people for whom a generation’s worth of dazzling innovation had brought barely any extra income on average. America had been churning out some of the most ambitious and impressive companies in history, connecting a billion people here and a billion people there on their networks, and in the shade of their growth was a country ever more unkind to ordinary people. “Society tells me I have to go to school, get a good job, and then I’ll get a salary, because I’m in America,” Jacobs said on another occasion. “And that’s what I did, and now I’m in debt. And now I’m suffocating.”

  Jacobs’s story exposed multiple malfunctions in the machinery of American progress. It implicated the country’s health care system and the problem of unaffordable drugs; its public transport system; its wage and labor laws; its food system and food deserts; its student debt crisis; its so-called great risk shift, through which corporate America has stabilized its own income statements over a generation by off-loading uncertainty onto workers; and the ways in which shareholders were running companies more and more for themselves, to the detriment of every other stakeholder.

  Vinod Khosla, the billionaire venture capitalist whose firm led an early investment round in Even, had taken to sounding alarms about lives like Jacobs’s being the looming reality for most Americans, unless the government intervened. He saw through the triumphalism of his Valley circle. Sitting in his second-floor conference room one morning, nursing a cold, Khosla said he expected the disruptions that had already wreaked so much havoc in working-class lives to continue and intensify as automation spread through the economy. He expected the world to continue to overflow with innovation but remain short on progress, if progress implies the flourishing of human beings. He believed that seven or eight out of ten people in the not-too-distant future might not have steady work available to them. To him, this coming future was both an entertainment problem (how would we occupy the minds of all those people?) and a political one (how would we keep them from revolting?).

  Khosla, interestingly, did not seem to think that apps like the one he had bet on in Even were the right response to the problem. The thing that could stave off social unrest, he said, is “if—big if—we do enough redistribution, if we handle minimum standards of living for everybody where they work when they want to work, not because they need to work.” He knew that such redistribution could cost people like him dearly, in the form of higher taxes. But it was a good investment, he felt. “To put it crudely, it’s bribing the population to be well enough off,” he said. “Otherwise, they’ll work for changing the system, okay?”

  The rather different approach proposed by Even had winners charging people like Jacobs money to facilitate her insuring of herself, helping her stabilize her life while turning a profit for themselves. It was understandable, and revealing, that a winner who had already made more money than he would ever need felt free to call out the limitations of such an approach—in a way that his young investees, with their fortunes yet to be made, did not. The billionaire investor was describing a massive collective social obligation, which the founders he had invested in were trying to turn into a win-win of a personal-finance app.

  This reframing was a source of worry to Jacob Hacker, a Yale political scientist who coined the “great risk shift” with an eponymous book and whose work helped to inspire Even’s founders. “Even is a personal solution to a public problem,” he told me. Hacker, who was among the first to make rising income volatility a national issue, said he was “fascinated” by Even. He thought the idea “deeply attractive and intriguing,” with “many questions to be worked out, but also much to admire” in the business model. Yet he was concerned. “Does its introduction lessen the pressure for collective action, either private collective action like unions or public collective action like social movements?” he asked. “It would be a sad irony if a great new Band-Aid headed off the maj
or surgery—expanded unemployment insurance, paid family leave, unions and new union alternatives, and so on—that an insecure citizenry so desperately needs.” Hacker was referring back to groups of individually powerless citizens potentially banding together to gain strength in numbers and stand up to powerful interests—the idea, in short, of political action. That idea was now up against a far more seductive approach: the winners of the world deciding what and how much largesse to give, or concentrating on the Venn diagram overlap of solutions to underdogs’ problems that also served them—and doing just enough of these things to keep at bay that very explosive impulse of banding together.

  If you asked the question, “What is the best way to help Heather Jacobs?,” the honest answer probably wouldn’t be to charge her $260 a year to smooth her income. If you were a person of education, privilege, and access to resources, as everyone at Even was, you might conclude that you should do something to repair the systems that are working to keep Jacobs poor. But if those problems were solved, you wouldn’t have much of a win-win business to grow. If it became illegal to employ the Heather Jacobses of the world in the way that she was, or if Khosla’s idea of massive redistribution were to be realized, Even might become unnecessary.

  CHAPTER 3

  REBEL-KINGS IN WORRISOME BERETS

  One recent November, Stacey Asher and Greg Ferenstein and a few thousand other citizens of MarketWorld found themselves aboard a 145,655-register-ton Norwegian cruise ship bound for the Bahamas. The idea of doing well for yourself by doing good for others is a gospel, one that is celebrated and reevangelized at an unending chain of tent revivals around the world. The citizens of MarketWorld can reinforce the mission at conference after conference: Davos, TED, Sun Valley, Aspen, Bilderberg, Dialog, South by Southwest, Burning Man, TechCrunch Disrupt, the Consumer Electronics Show, and now, at Summit at Sea, on a cruise ship full of entrepreneurs wishing to change the world.

  Summit at Sea was a four-day-long maritime bacchanal honoring the credo of using business to change the world—and perhaps of using “changing the world” to prosper in business. It brought together a great many entrepreneurs and financiers who invest in entrepreneurs, some artists and yoga teachers to keep things interesting and healthy, and various others who tend to run in those circles and whose bios refer to them using terms like “influencer,” “thought leader,” “curator,” “convener,” “connector,” and “community manager.” Summit, being one of the hotter MarketWorld tickets, had drawn to this cruise ship the founders or representatives of such venerable institutions as AOL, Apple, the Bitcoin Foundation, Change.org, Dropbox, Google, Modernist Cuisine, MTV, Paypal, SoulCycle, Toms Shoes, Uber, Vine, Virgin Galactic, Warby Parker, and Zappos. There were some billionaires and many millionaires on board, and lots of others who had paid a typical American’s monthly salary to attend.

  Selena Soo, a New York publicist who was on board and represented many of these entrepreneur types, perfectly captured the prevailing view. “I work with clients whose personal mission is to improve the lives of others,” she writes on her website. “When their business grows, the world becomes a better place.” Blair Miller, who was also on the ship and has long worked at what she sees as the nexus of business and social good, once put it this way in an interview published by a clothing boutique:

  The question for me was never if I should devote my career to social impact, it was always HOW can I make the most impact? Business is a dominant force in the world today and I believe that if I can influence how business is done, I can change the lives of millions around the world.

  Once you believe that business is how you change things these days, a conference of entrepreneurs offers unlimited possibilities. Indeed, many boarding the ship had recently received an inspirational message from one of the conference’s organizers that framed Summit’s mission in world-historical terms:

  The winds are picking up in the east and in six short days something transformational is going to be born from the sky and the moon and it might just change history. We may not see the full effect now…but that’s the case with any great shift in culture. Any great seismic shift amongst the plates of planet earth.

  A motivational speaker and thought leader named Sean Stephenson would offer a slightly more candid, if no less ambitious account of Summit’s purpose in a welcome speech to the attendees. It came in the form of three pointers for making the most of this chance. First: “In this room you can make contacts that will help you have cascading effects on humanity.” Second: “You’re going to make friends who are going to impact your pocketbook.” Third: “The Boat’s not about getting drunk and getting naked. Well, it’s sort of about that. But it’s also about social justice.”

  And yet the stubborn facts of an age of stark inequality clouded this vision of the pocketbook-impacting approach to social justice and the use of business to unlock potential and birth transformational things. The more these entrepreneurs waxed about changing the world, the more those facts got in their way, mocking their grandiose and self-serving claims. And this was most acutely true for a subtribe of the attendees of Summit at Sea: those hailing from Silicon Valley and the world of technology, with its audacious claims, even by MarketWorld standards, that what was good for business was great for mankind.

  The new barons of technology were the Rockefellers and Carnegies of our time, amassing giant fortunes, building the infrastructure of a new age, and often claiming to operate in the service of civilization itself. “What’s amazing about tech,” Justin Rosenstein had said in light of his experiences at Google, Facebook, and his own start-up to change the world, “is that there are so many opportunities to have your cake and eat it too, right?” Yet there was no denying that as they chewed away, these technologists were also partly responsible for prying inequality as unsustainably wide as it had gotten. (It was no accident that the city they had adopted, San Francisco, had become perhaps the most cruelly unequal of American cities, with less and less space and chance for ordinary people to make a life.) Many of them had clamored for the dismantling of systems designed, among other things, to protect equality, such as labor unions, zoning regulations, or the laws that assured job security and benefits for workers.

  How was the faith in the win-win maintained in the face of widespread evidence that one was in fact contributing to inequality? How did these new barons relieve the cognitive dissonance they might have felt from claiming to improve others’ lives while noticing that their own were perhaps the only ones getting better? One day at Summit at Sea, in the well of the Bliss Ultra Lounge, on the seventh floor of the ship, a high priest of this technology world, a venture capitalist named Shervin Pishevar, was demonstrating one form of relief.

  Pishevar was among the leading venture capitalists in the Valley, a status he had cemented by placing early bets on Airbnb and Uber. Those investments earned the kind of returns that could allow one’s grandchildren to be full-time philanthropists. Pishevar was an Iranian-born immigrant whose adopted country, through its Department of Homeland Security, had named him an Outstanding American by Choice. He was a kingmaker in the Valley, whom the founder of Uber, Travis Kalanick, had reportedly leaned on as a tutor in the art of going clubbing in Los Angeles, with Pishevar providing “club clothes,” according to the New York Times. And the entrepreneurs at Summit at Sea knew that a VC like Pishevar, whose firm was called Sherpa Ventures, was in a position, should he so choose, to guide any of them to the mountaintop.

  This knowledge helped explain the crush of bodies that had come to see Pishevar’s talk, titled “All Aboard the Hyperloop: Supersonic Storytelling with VC Shervin Pishevar.” People were curled up on armchairs and sofas; some sat and others lay down on the ground; still others hovered above, ringed a few deep around a balcony on the eighth floor, peering down. The crowd was listening in rapt, reverent silence.

  What they heard was a powerful man who seemed at pains to explain his
power away and to cast himself as a man in pursuit of things nobler than money. “Sharing is caring,” Pishevar said at one point. He admitted it was corny, but he said he truly believed it. “At the end of the day, it’s not about the money,” he continued. “It’s about the love and those moments of character.” The Summit people clapped hard and whooped in recognition. They believed it wasn’t about the money for them either, one would guess.

  Pishevar turned to the topic of life-extending technology, which was a major focus of his work now. He was hardly the only Valley man pursuing the elongation of the lives of people who presumably could pay. “The next twenty, thirty years, my best piece of advice is stay alive,” Pishevar said. “Don’t take really stupid risks”—this clashed with his business mantra of taking as many risks as possible—“physically, I’m saying. And get ready, because the things that are coming down the pipe in terms of genetic research, our life spans and the health of our lives are going to be longer, and it’s going to challenge the very basis of our current civilization: The way things are structured today are not going to be relevant to what the reality is going to be of people who are going to have so much knowledge and living so long and healthier lives. The idea of retiring at seventy is gonna seem like people telling you at thirty to retire.”

  Here Pishevar was engaging in advocacy that disguised itself as prophecy, which was common among technology barons and one of the ways in which they masked the fact of their power in an age rattled by the growing anxieties of the powerless. VCs and entrepreneurs are considered by many to be thinkers these days, their commercial utterances treated like ideas, and these ideas are often in the future tense: claims about the next world, forged by adding up the theses of their portfolio companies or extrapolating from their own start-up’s mission statement. That people listened to their ideas gave them a chance to launder their self-interested hopes into more selfless-sounding predictions about the world. For example, a baron wishing to withhold benefits from workers might reframe that desire as a prediction about a future in which every human being is a solo entrepreneur. A social media billionaire keen to profit from the higher advertising revenue that video posts draw, compared to text ones, might recast that interest—and his rewriting of the powerful algorithms he owns to get what he wants—as a prediction that “I just think that we’re going to be in a world a few years from now where the vast majority of the content that people consume online will be video.” (New York magazine had skewered Mark Zuckerberg after he issued that prediction at the Mobile World Congress in Barcelona: “The Vast Majority of Web Content Will Be Video, Says Man Who Can Unilaterally Make Such a Decision.”)