Insanely Good: Making Big Business Out of Social Philanthropy

The reckoning for entrepreneurs in the tech industry was not the loudest to arrive this year, but it came colorfully: the struggle to set boundaries against hate speech on Twitter, the congressional hearings for Facebook and its subsequent moves toward content moderation, the weird and weepy interview that Elon Musk gave the Times. Titans who stood tall ten years ago are wobbling in their sneakers, and the forward-looking innovation business seems to be, all at once, on its heels. “If you have anyone who can do a better job, please let me know. They can have the job,” Musk said. At a Senate Intelligence Committee hearing last week, Twitter’s C.E.O., Jack Dorsey, described the company as “unprepared and ill-equipped” to deal with trolls, propaganda, and harassment. Such lamentations may seem to bring crepuscular hues to tech, but it’s more likely that they signal an approaching change. An industry known for outlandishness will be driven toward brass-tacks problems. Random acts of philanthropy will no longer be enough to keep the giants in good grace. The looming question isn’t whether high-profile entrepreneurs will work to win back favor but how. Some might describe it as a juncture primed for innovative thought.

One recent sweltering Monday, I went to visit Ankur Jain, a twenty-eight-year-old entrepreneur who, as much as anyone, reflects tech’s recent drift toward a new form of social self-awareness. Jain’s father, Naveen, started the Web-service company InfoSpace in the nineteen-nineties. He left it amid a flurry of lawsuits, including a settlement over short-swing trading, and later co-founded a company called Moon Express, which is building spacecraft to mine precious metals and nuclear fuel from the moon. When Ankur was a child, his father encouraged him to pitch business plans to family friends. The lessons, and the confidence, took. While Jain was in college, at the Wharton School, the financial press called him “possibly the world’s best-connected 21-year-old.” At twenty-six, he sold a company to Tinder, whose product he went on to lead.

Since then, he has launched a new mission. “Facebook, Google—these companies are impacting the way people live more than government. But, unlike government, there’s not an explicit mandate that they’re responsible to communities and society,” Jain said. Tech is too focussed on extreme-use cases and moon shots, he thinks, and too neglectful of practical problems. “The biggest needs right now in society have to do with key life services that, historically, governments provided,” he told me. “Education, housing, family services, and childcare.”

I met Jain in an open office at Hudson Yards. Although he founded his first startups in San Francisco, he has lately been down on the Bay Area, which he believes has grown polarized and homogenized by tech. His organization, Kairos, runs out of New York, in a workspace that he and eight colleagues share with a larger company. (“Hudson Yards is the coolest,” Jain says.) A robot on a nearby ledge bore a sign that read, “Hi there! My name is Jibo (Jee-Bo),” and invited passersby to inquire about the weather. I asked for the forecast, but Jibo just looked perplexed.

“Technology!” Jain exclaimed behind me, and laughed. He is slim, with a sunny disposition and an affect somewhere between wonderment and incredulity: a way of casting himself as an outsider, though in truth he’s on the inside almost everywhere he goes. With help from William Owens, a friend of his father’s and a former vice-chairman of the Joint Chiefs of Staff, Jain and a college-era Alex Fiance had co-founded Kairos when he was eighteen, as a club for entrepreneurs that could connect titans of industry with one another and with ambitious and savvy young people like them. The idea was that both sides would benefit: the Youngs would get prime connections and funding, while the Olds would get first crack at the era’s bright young minds.

Today, Kairos is part élite membership society—for a while, members would identify one another across conferences with a special lapel pin—and part business shell. It offers fellowships, which center on access to élite leaders, for young entrepreneurs. Its board includes the president of Verizon Wireless, the president of Hearst Magazines, the commissioner of the N.F.L., the C.E.O. of the New York Times, and Bobbi Brown, a titan of cosmetics. A Vanity Fair report on the company’s summit last year described a Gatsbyesque scene of hired helicopters and stretch-limousine vans ferrying rich, powerful, and famous guests—among them Joseph Gordon-Levitt, Dr. Mehmet Oz (another board member), and the then editor-in-chief of the Wall Street Journal, Gerard Baker—to the Rockefeller estate for an opening dinner.

Jain himself rarely talks of “colleagues,” but he often speaks of “friends.” At one point, while we talked, he drew out his iPhone and started scrolling through some recent correspondence with Vicente Fox, the former President of Mexico, who is a Kairos board member. “He’s doing an initiative to try to figure out how new technology can increase corn yields in Mexico to reduce the dependence on U.S.-Mexico over biofuel imports,” Jain explained. “Hopefully, we can be helpful to him. He’s very helpful to us. And we’re friends—that’s the most important thing.”

Ankur Jain.Photograph by Mary Kang for The New Yorker

At the headquarters of Kairos (which is unlisted on the office’s signage), Jain led me up sleek wood stairs cased in glass and to a pair of futuristic high-backed chairs, next to a window overlooking lower Manhattan. “Could we be there?” he asked a man already seated. It was Jain’s place for having conversations. He was wearing a charcoal shirt and gray jeans, and carrying a small bottle of San Pellegrino. The man stood quickly and departed. “There’s this question of what is tech’s responsibility,” Jain said after we’d settled. “What are the opportunities for new innovation to build and create wealth—but also to help people?”

It was, Jain explained, a problem he’d been struggling with. His idea was to use the Kairos network to drive techie minds from novelty apps and cutting-edge appliances and toward more fundamental problems. “No one is fixing housing for the everyday consumer in the middle class,” he said. Recently, he and various “friends” pooled twenty-five million dollars and began to call for ideas. One of the Kairossians, Paraag Sarva, had proposed replacing security deposits with insurance: renters would pay a relatively small sum as a premium, and landlords would get a payout if something went awry. Such a model, Jain told me, would be safe for landlords and good for renters, since, in theory, they could invest money instead of putting it in deposits. (At the moment, there are five hundred and seven million dollars held in security deposits in New York City.) It would also build a new insurance market. Last year, Sarva co-launched a company, Rhino, under the aegis of Kairos. It currently provides landlord insurance to seventy thousand units in New York and had its first political victory in July. A friend, the entertainment C.E.O. turned private-equity giant Edgar Bronfman, Jr., had introduced Jain to the city’s comptroller, Scott Stringer. After some discussion with Jain, Stringer called for alternatives to security deposits and professed support for Rhino-like insurance. “My friends all gave me shit—I missed the World Cup finals because Comptroller Stringer decided to do his announcement at the same time,” Jain said. “But it was worth it.”

Local governmental meetings of this kind have lately turned into a specialty for Jain. Kairos now comprises more than fifteen companies in what he calls “essential services.” Jain said, “It’s a little bit like the Virgin Group, in terms of the way it’s structured.” Each company will benefit from specific political accommodations. Another Kairos spinoff, Homevest, acts as a “silent partner” in real-estate purchases: you contribute, say, forty per cent of a down payment on a house, and Homevest, representing a pool of real-estate investors, buys the rest. (The investors get their return when you later buy out this equity or sell the house.) Yet another, June Living, subdivides homes and individual apartments into single-room rentals. “We have housing now fairly locked down,” Jain told me. Kairos is currently working on childcare, senior care, and debt. “You’re seeing huge barriers to the cost of starting a family.”

Kairos’s recent expansion, Jain said, is informed by an epiphany that he once had. The epiphany was that vanguard tech—Alexa, blockchain, A.I. cars, smart toasters—was an élite sector for élite people, and thus a relatively small market. Everyday services, meanwhile, especially those that helped working Americans make ends meet, formed a business sector that was lucrative and large. “Housing is a trillion-dollar market; education is already 1.5 trillion, in student debt; and childcare is an almost trillion-dollar market,” Jain said. “It’s funny—people bucket these into social, charitable things, but there is more money spent on these services than any other category out there.” He smiled and said, “This isn’t philanthropy.”

Alarm about the socioeconomic effects of the tech industry’s growth is often framed within a long-term rise in inequality in the United States. People who study such changes sometimes split the trend into an “upper tail” (income inequality between the fiftieth and the ninetieth percentile, or between the middle class and the rich) and a “lower tail” (inequality between the tenth and fiftieth percentile, or between the poor and the middle class)—a division that helps to show not only how much inequality there is but also where it comes from. Through the nineteen-seventies and eighties, lower-tail wage inequality was higher. Since the mid-nineties, upper-tail inequality has been preëminent and rising, while wage inequality between the poor and the middle class has barely increased. Figures like those suggest that recent changes in inequality stem chiefly from the way that already affluent people go about earning more. Jain concurs. “The problem is that there’s so much wealth at the top right now,” he told me, echoing a common refrain.

Seen in one light, upper- and lower-tail differences suggest that America’s inequality problem is really two separate puzzles, calling for distinct solutions. Lower-tail inequality, being a longstanding problem, has given rise to ongoing debates: Who should help the poor, and how? Upper-tail inequality is less thoroughly chewed over in the frame of mainstream policy—oddly, perhaps, given that it is the distinctive inequality of our time. A famous graph by the Economic Policy Institute shows American wages growing with increased productivity until, in the mid-nineteen-seventies, they began diverging. Some observers suggest that a shifting regulatory and financial environment encouraged companies to be accountable to equity holders rather than to employees—essentially, to take money that once went to the middle class and invest it elsewhere to maximize the price of shares.

Such a model is the basis for today’s commercial-tech industry, habitually venture-backed and thus run to produce shareholder value. And it shaped the entrepreneurial landscape into which Jain was born. In 1996, when Jain was six, his father left Microsoft to start InfoSpace, working without venture capital, the better to retain control of the company and its profits. Since Ankur’s mother also worked for the startup, he spent his afternoons after school in its offices, doing homework or playing video games while breathing the fumes of a business launch. When InfoSpace went public, in 1998, his father took him out of school and flew him around to meetings, to show him how an I.P.O. was prepared. Ankur was seven, going on eight.

“I was just thinking, All these guys in suits, and all I want is an orange juice and a chocolate milk,” he said. “During those experiences, my dad would often put me on the spot to give talks”—childlike assessments, usually, about a business idea’s viability. (“Why don’t you come up here and tell everybody what you think?” he recalls his father asking.)

By eleven, he had founded his first company. Texting was starting to emerge as a phenomenon. So was AOL Instant Messenger. Messenger was fast, but, Jain realized, with entrepreneurial zeal, texting was still frustratingly slow—a problem to be solved. “You had to type, like, 2, 2, 2 to write a message. It was very painful,” he recalled. He built a platform to send texts from a computer, Messenger-style. He added games. “We had, at one point, almost two million users. I couldn’t believe it,” Jain said. He was thirteen. The company died a couple of years later, when he forgot to turn on the air-conditioning in his bedroom, which held all the servers: “I came home one day from school and my system had the blue screen of death.”

At Wharton, Jain’s attention migrated away from the screen and toward people. The company he founded in his early twenties, Humin, offered a more organic way of databasing contacts, searchable according to, say, people you met four weeks ago, or people you knew in Austin—a tool for emerging butterflies, such as Jain, who had trouble keeping track of all their friends. The app launched with famous investors, including will.i.am and Richard Branson, as its frontmen. To drive young people toward Humin, he created another app, Knock Knock, which let users open a smartphone contact portal with people within Bluetooth range—for instance, in a dorm or in a lecture hall.

When Humin was acquired by Tinder, in 2016, Jain went with it, to lead Tinder’s product team. He worked on adding a V.I.P. service, for putative celebrities. “Dating is a little bit like night life, and one of the things that we learned was that people want to go to the place where they think all the celebrities go,” he explained. But he found himself much more excited by the normals on the platform, who made it clear how far a useful piece of tech could carry.

“A single feature we built fundamentally changed how the world dates,” he said. “We would change the way the product was designed, and all of a sudden the way people meet fundamentally changed—the amount of marriages, the amount of kids.” Often, the greatest change was no change at all. “We launched features that made it really, really easy to meet up in real time,” he recalled. “You could press a button and say, ‘Hey, I’m down for drinks—want to meet up?’ Imagine a remote control for your social life!” It didn’t take. “For a lot of people, it was just the fun of swiping and matching and feeling like you’re validated.” This got him thinking less about tech’s special capacities and more about its relationship to the safe and the mundane, the crawl of everyday life challenges. Imagine being able to generate returns for equity holders while also helping the normals with life problems! Jain refers to such a project as “win-win.”

Photograph by Mary Kang for The New Yorker

The wins, of course, are in proportion with the current socioeconomic landscape—which is to say, consistent with upper-tail trends. A Rhino user can hope to knock a few thousand dollars in security off his or her books, while an investor who has put a million dollars into the company can hope for a return generating many millions more. This is by no means a count against the service. (A few thousand dollars is often the difference between solvency and penury, enough leeway to rescue many people in the middle class.) But it raises the question of how deeply such wins, iterated over time—big, risky payout upon big, risky payout for shareholders, and small, stable savings upon small, stable savings for users—might heal the inequality that Jain laments. A pessimistic view would regard this as the equivalent of a fast-growing company charging consumers for a leaky bathtub and then charging for a mop to clean up the mess. Having channelled a goodly bit of wealth away from middle-class workers, investors are now whirling around and running back over the same landscape, seeking a new windfall from the big business of help.

But Jain is not a pessimist—quite the contrary—and he points out that it’s better to have powerful companies, ambitious leaders, and clever people doing something for these problems than to have them doing nothing. Thirty years ago, a working parent trying to survive in the city might have been compelled to take out a predatory loan. Thirty years ago, too, bottom-line-oriented companies could be counted on to sell cheap, unhealthy foods to maximize profits. Now companies like Rhino and Homevest are offering a way to help keep middle-class people afloat, and—well, a Kairos company, Little Spoon, just launched a baby-food line to help “solve” food. The idea was that techie-style, quinoa-age entrepreneurship hasn’t reached the world of puréed carrots (or, in the case of Little Spoon, pea, tahini, green apple, thyme, avocado, ground chia, and pear, which ostensibly build muscles and brains before it’s too late). “Baby food hasn’t changed in a hundred years,” Jain observed.

He was preparing for the Little Spoon event when I met him a few days later. Toting a La Croix, he led me back to his talking chairs, near the window. “The biggest barrier” to building a company, he said, “is that people are inherently resistant to change.”

Getting past resistant people is today a large part of Jain’s job. He had spent the morning in meetings: a breakfast with Alex Fiance, followed by two hours on the phone with Rhino people, mulling a new product. He had met with Tonye Cole, the Nigerian billionaire and Sahara Group co-founder, who is one of his investors (and a friend), and who was in town for the United Nations. (“We sat down to talk about, ‘What are some of the challenges in Africa right now?’ ”) He had met with the C.E.O.s of three of Kairos’s housing companies. The following day, he would leave for San Francisco—not to visit his partners there but to see partners from Abu Dhabi, who happened to be passing through California. Along the way, he hoped to get a chance to see his sister, who lives in New York, and his brother, who is a senior at Stanford. “They’re the stars of the family,” he said.

I asked Jain what he envisaged himself doing at the age of forty. He shrugged and demurred for a moment, and then offered an extremely comprehensive answer. “I’d be able to actually have products and services that are being used by people all over the world as their default for these key parts of their life,” he said. “They live in housing that’s set up by Kairos. They’re using childcare set up by Kairos—or at least we played a hand.” Then it was time for him to leave for another meeting, so he led me to the elevators. He shook my hand warmly, and it was quiet and comfortable on the ride all the way down.

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