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  Terrence had pretty much stopped praying after his mother died years earlier, but one morning, before he left for his volunteer job, he knelt down and asked God for help. What he was doing—working with kids in his hometown of Dumas, Arkansas, at a church free meal program—wasn’t solving the bigger problems he saw in his community. He asked God to help him find a better way.

  Dumas is a town of around 5,000 people in the Arkansas Delta that is surrounded by cotton fields once picked by slaves, then by sharecroppers, and, now, mostly by machines. Its residents on average make $22,000 per year, and almost 40% of the town lives in poverty.

  Growing up, Terrence had never considered his family poor. Between the ages of five and ten, he’d lived with his mother and grandmother in an old sharecropper’s house, which was part of his grandmother’s compensation for working as a maid at the town’s plantation. Later he’d moved into a house with his mother, where he lived on and off until graduating from high school. He had gone to bed every night with a roof over his head and never went hungry.

  Not everyone he knew could say as much. Nobody in Dumas or Pine Bluff, where Terrence’s father had lived, ever talked about their poverty, but Terrence remembered small moments throughout his childhood that gave it away. Like the time one of his friends noticed a slop bucket where Terrence’s family scraped their plates after dinner—food for his uncle’s hogs—and rescued a piece of pizza that was sitting on top of it. Food was food. And “poor” was a relative term.

  Though Terrence didn’t finish the chemical engineering degree he started at the University of Arkansas, he had taught himself how to code and how to design websites. Between the odd website job and his paycheck from selling shoes at a department store in Fayetteville, the city where he was living at the time, he was doing ok when he got the call that brought him back home.

  His younger brother had fired a gun at a woman, who sustained non-fatal injuries. He then had run away, and shortly later, he was discovered dead.

  Terrence found the way the authorities had handled his brother’s death to be suspicious. He had moved back to Dumas to take care of his grandmother, but also to investigate. As he pursued the question of what had happened that night, it opened other questions about what had happened to his community over decades. Why was the poverty rate among African Americans in Dumas more than double the poverty rate among white people in Dumas? In a county with as many African American people as white people, why were seven businesses in the county owned by African Americans, compared to 117 owned by white people?

  Terrence had early on encountered racism. In high school, the white kids and African American kids had parked in separate parking lots. In college, a professor had failed him for turning in a paper that was too good, saying it couldn’t be his work. Later, as a website designer, he’d lost a promising job as soon as he met the client in person. But this new line of questioning made him think about his community in a way that he hadn’t considered before. It was one thing to not have access to opportunities that you were qualified for because of the color of your skin. It was another thing to not be qualified for the opportunities in the first place. Why were the people he’d grown up next to in Dumas so often hopeless, mistrustful, and seemingly unmotivated?

  In order to fix the problems in Dumas, Terrence believed he had to study their origin. In records Terrence found at city hall and through interviews with elderly community members, he started piecing together a history of African Americans being cheated out of their land rights. And he started thinking about how the injustice of slavery, Jim Crow, and lynchings sparked trauma that could fester inside a family for generations. How these inherited wounds could compound to make people “unemployable.”

  Terrence’s first attempt at helping his community was to join the church program that fed kids free meals. When only a few kids showed up, he started to ask kids in his neighborhood, “What did you eat today?” The question was meant to be specific, to address a problem in the way that simply asking “Are you hungry?” couldn’t—because hunger, too, was a relative concept.

  When it became clear that not everyone who needed a meal could get to the church on their own, he started a bus route of sorts, picking up kids in his Chevrolet Malibu to drive them to the meal program. On the ride, he tried to teach the kids how to think differently—to have hope and treat each other with more respect.

  But he soon realized he couldn’t teach kids without their parents’ support, and that support didn’t always come; in fact, some resented his efforts. It made some sense to him that parents took offense, for instance, when he told their children not to retaliate with violence if another child hit them. Their grandparents had been raised by people who remembered slavery, people who had been punished through violence and never had a choice about whether to fight back. So when Terrence said, “Come talk to me instead of returning a punch,” it could seem to these parents like he was teaching their children to be weak.

  Lectures delivered during a 15-minute drive weren’t enough to undo a deeply entrenched culture. Terrence decided he needed to find a way to reach parents. But how? What Terrence considered to be God’s answer to this question arrived in a message from Dumas’s superintendent of schools, who had once sat in on one of Terrence’s Sunday school classes.

  Terrence is a good teacher. He can tell the most heartbreaking story you’ve ever heard while still finding a moment to punctuate it with a blinding smile and a shot of optimism, and he has a way of breaking things into metaphors that makes them dramatic and understandable. Hearts are like fertile ground, he told me, while explaining why it was hard for the residents of Dumas to trust outside organizations. Experiences are like seeds.

  The superintendent had been impressed when he’d dropped in on Terrence’s class. Now he was trying to reach Terrence to tell him that a woman was in town to hire a teacher, and he wasn’t going to let her leave until Terrence came for an interview. The message finally reached Terrence when the superintendent’s niece found him at the food program.

  Terrence didn’t have enough time to study what the job entailed. He ran home, changed his shirt, and arrived in a sprint at the community technology center on Dumas’s main street. The woman who met him there worked for a non-profit called Samasource that had, until recently, operated mostly in East Africa and India. Founded by a Silicon Valley social entrepreneur named Leila Janah, its mission was to “give work” to people living in extreme poverty. The idea was that giving a thing like food only temporarily met physical needs, but with work came dignity and a path out of poverty.

  Since 2008, before Uber for everything, the non-profit had been making work contracts with tech companies like Getty Images, Google, and eBay. Those clients would have probably outsourced tasks such as tagging images or categorizing data in any case, but Samasource made sure they outsourced it to people living in extreme poverty. Now Leila Janah wanted to try a similar concept in the United States. Her organization had launched pilot programs in several California locations and now sought to expand eastward, to Dumas, Arkansas. The project was called “Samaschool.”

  At the interview, the woman told Terrence about how the gig economy might help end poverty in towns like Dumas, where great opportunities no longer existed and were unlikely to reappear. Workforce development typically involved attracting more businesses, or encouraging people to start new ones. Samaschool hoped the internet could help Dumas leapfrog this long, slow process. It would teach the town’s residents how to access opportunity created elsewhere.

  The Dumas program would work differently than the program that Samasource ran in other countries, where it hired workers to complete projects for US companies. Dumas workers would instead find their own opportunities through the gig economy.

  Just a few hours after Terrence had prayed for a way to help his community, he felt as though he’d found it. “If I give you this dollar,” he told me, “and then I put you on a deserted island, it’s worthless.” Work wasn’t like that. L
ike land, it had inherent value. Terrence wanted the people in Dumas to unlock that value. He was definitely interested in the job.

  The woman who interviewed Terrence told me she decided within moments of meeting him that he was the right fit for the project. He had charisma and energy, he had grown up in the area, and he was totally devoted to the cause of helping his community. Terrence came back to the tech center for another interview with Samaschool, and then another, the last one with its founder. He felt a connection with Leila, because they had the same passion. If he’d had the same network as Leila, the same access to resources, he imagined that he and Leila would have had a lot in common.

  Why Dumas? he asked her.

  Leila had run into the head of the Arkansas state economic development agency after speaking at the Clinton Global Initiative. He had opened the door for a pilot program in Dumas, which was funded by the Winthrop Rockefeller Foundation, a nonprofit focused on improving life in Arkansas. As Terrence remembers it, Leila talked mostly about the potential she saw in Arkansas.

  To Terrence, it didn’t really matter why Samaschool had come to Dumas. He was just glad that it was happening. And a couple of weeks later, when he got an email that let him know he’d been hired as a teacher, he was ecstatic to be a part of it. He hoped that the gig economy—specifically Leila’s vision for it—would play out in Dumas as it had been conceived in Silicon Valley, that it would serve as a conduit for opportunities that had otherwise left his small town, and others like it, behind.

  CHAPTER 4

  UBER FOR X

  Travis Kalanick joined his first startup more than ten years before co-founding Uber, dropping out of the University of California, Los Angeles, to work on a peer-to-peer music- and video-sharing startup. Airbnb’s first founders met at the Rhode Island School of Design. Two of Upwork’s cofounders created the freelancing site after working together, but from separate countries, on a previous startup.1 Like most of the people who founded gig economy companies, these founders were experts in creating technology products, not in mobilizing and managing large service workforces. Most had little or no experience in the industries that they now set out to disrupt.

  Among the horde of tech entrepreneurs who launched service-sector startups in the wake of Uber’s funding announcement, Dan Teran and Saman Rahmanian made an unlikely pair.

  Not only did they both depart sharply from the Mark Zuckerberg brand of young, nerdy founder, but they did so in nearly opposite directions.

  Dan, with floppy blond hair, blue eyes, and the tall athletic build of a former college rugby player, could have looked like a preppy frat boy if he’d wanted. Instead, he went too long without a haircut, smoked openly, and developed a dry, sometimes biting, sense of humor. At 24, he could reasonably be described as cool.

  Saman was in his early thirties, married, and a father of two—nearly a senior citizen by Silicon Valley standards. He didn’t smoke, drink, or swear.

  The two entrepreneurs met in 2013 at Prehype, a startup accelerator that partners with big brands to launch entrepreneurial ventures. Saman was a partner there and, along with the firm’s other partners, interviewed Dan for a job.

  Dan at that point didn’t exactly have a stellar resume for an “entrepreneur in residence.” For most of his life, he had wanted to be a politician: He’d organized a state Senate campaign for a former firefighter, received a college degree in a major he’d invented called “Urban Public Policy,” and taken his first job out of college as a paralegal. His only experience with startups was his current job, as the first employee of a startup called Artsicle that sold art online.

  But Dan had always been good at talking himself into things. His family joked that he’d talked his way into Johns Hopkins University (and in fact, his admission had involved tracking down everyone he could find who worked in the admissions department, many follow-up emails, and a promise—which he’d made good on—to be an extremely, extremely engaged student). When Dan had first decided that he wanted to work in tech, he started reading TechCrunch every day to absorb the culture and lingo—not an easy feat in the age of the buzzphrase “So Lo Mo” (in case you were not in the know circa 2011, this was short for “social, local, mobile” at a time when entrepreneurs were even less self-aware).

  He’d landed the job at the “Netflix for art” startup partly because he knew a lot of artists. Or, at least, his roommate at the time was a photographer for the New York Times, and when he got invited to an interesting event, he brought Dan along to hold his flash. Dan had held a flash at an Alexander Wang fashion week party; at the Westway, a former strip club near New York’s West Side Highway, as the fashion designer Valentino sang a karaoke version of “My Way”; and at the eightieth birthday party for Massimo Vignelli, a graphic designer known for creating the 1972 New York City subway map and other iconic designs. A few nights a week, he tagged along with his roommate to gallery openings. It was a reliable way to eat and drink for free.

  As Artsicle’s first employee, an experience Dan recounted in his Prehype interview, Dan had taught himself how to design a website, made art deliveries, and worked “like a dog.” It was the best feeling in the world, knowing that a startup would succeed or fail based on your own efforts.

  Saman liked Dan’s hustle and “creative sensibility.” He recommended him for the job. The project Prehype had thought Dan might work on fell through shortly later, but even though he wouldn’t be paid until being assigned to another one (the Prehype partners worked on contract), Dan started showing up.

  It was not exactly glamorous work. Prehype’s office was situated above a dumpling shop in New York City’s Chinatown. Other tenants in the building included a garment factory and, according to the labels on boxes that regularly appeared in the freight elevator, a large importer of “fish balls.” Underneath a sign in the lobby that said “NO SMOKING, NO SPITTING, NO LOITERING,” men often gathered to do all three.

  Dan would sit in the small room that Prehype’s six members shared and make calls for a project that Prehype was trying to land. He was essentially a volunteer.

  Saman respected him for it. Showing up, whether or not there was work to do, had been a virtue drilled into him by his father, who had once worked as a government official in Iran and, for most of his childhood, had run a Persian rug business in Austria. Every day, at his father’s insistence, the rug shop had opened exactly at 9 a.m. and closed exactly at 6 p.m. No matter what, it never opened a minute late, and it never closed a minute early—even if a customer hadn’t been sighted all week. “Work is worship,” Saman’s parents used to tell him, in Farsi, referring to the Bahá’í belief that work should not be merely a means of earning money, but also an expression of service to humanity. It was because of this religion that the family had been forced to flee Iran, and Saman didn’t take it for granted.

  Eventually, Dan became a regular contractor on Prehype projects. When he and Saman worked together, they found they made a good team, bringing a complementary set of skills to assignments that involved building new products or launching new services within large corporations. Saman was good with ideas. He enjoyed controlling every pixel in a product’s design, creating a brand, and telling a story. Dan, meanwhile, was all about getting things done, even if it required 16-hour days and less-than-graceful maneuvering. And when it came to confronting a problem, he was nothing if not direct. When one of his neighbors, for instance, started throwing cigarette butts, used condoms, and other incriminating garbage onto Dan’s porch, Dan collected a representative sample in a clear plastic bag and taped it to the neighbor’s door. Efficient, effective, but perhaps not the most delicate personal branding effort.

  More than one of Dan’s friends described him to me as “salt of the earth.” People he didn’t like, who he generally did not pretend to like, had more colorful ways of describing his straight-talking manner. In either light, Dan was undeniably effective, and he soon developed a reputation for hard work and efficiency. By the time Saman had
a startup idea that would change both his and Dan’s lives, less than a year later, Dan had gone from an unpaid volunteer to partner.

  Saman’s idea for a startup was to offer a solution to the often shoddy practice of building maintenance, a problem to which Dan could relate, as his apartment had many issues beyond a teenager using his porch as a garbage can. He lived in the kind of Brooklyn apartment in which brown liquid could drip from the ceiling without causing much alarm (to the building’s management, at least). The buzzer never worked, burnt-out hallway light bulbs remained in their sockets for months, and the front door was invariably broken. Sometimes the hot water tap ran cold. Other times, the shower temperature ran so hot it scalded his skin. He’d finally convinced building management to repair the dripping hole created by an upstairs neighbor’s overflowing plumbing, but he had to spackle the drywall himself.

  This housing situation was another aspect in which Dan differed from Saman, who lived in the kind of Brooklyn apartment building that included the name of its bathroom designer on the real estate listing. But even in a high-end apartment with floor-to-ceiling windows, bright white marble countertops, and multi-zone temperature control, Saman found managing his building’s maintenance to be frustrating.

  As Dan contemplated replacing hallway light bulbs himself, Saman—in an effort to make friends with the neighbors—had agreed to coordinate building maintenance for his condo board. He quickly regretted it. Keeping tabs on who had been in the building and what work they had done felt impossible. Why did it take a maintenance company six weeks to fix a broken lock? The superintendent was contractually obligated to sweep each week, but who could tell whether or not he had done so?

  If Dan and Saman both had this problem, it was a vast one, which was one reason Saman wanted to solve it.

  What he had in mind was a digital dashboard that could be posted in a building’s lobby. Through it, building managers would be able to communicate with cleaning, maintenance, and other service companies and to track the work they’d done. Saman called it Managed by Q, after the character in James Bond movies who supplies all of the cool gadgets. He pitched the idea to Prehype’s partners, and since he and Dan sat across from each other in a pod of desks, they ended up talking about it frequently. Dan started working on the project, too. Eventually, they decided that Dan should be a cofounder.