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  In July, when he’d first started the remote call center job, this hadn’t seemed like a problem. Because he took calls about broken air conditioners, there was more than enough work to do during the summer heat. When he couldn’t work 30 hours or didn’t want to, he had to let his boss know in advance so that his absence wouldn’t impact his rating as a contractor.

  When summer turned to fall, though, Gary started to realize he was in trouble. Still a couple of months away from broken heater season, he fretted about how many hours he would work the next week as the majority of the country enjoyed a temperate climate.

  Gary and other virtual call center contractors picked their hours on a rolling basis, with the highest rated among them choosing first. Hours were usually released every two weeks, but as time went on, fewer and fewer were available. Gary was lucky to get 15 hours each week. If someone else forfeited their hours in order to attend a doctor appointment or something unexpected, he could sometimes pick up a few more. “You scramble,” he said. “You check the board constantly, like every hour [you’re looking]. For a half hour here, a half hour there, to try to collect extra hours.”

  During the month he spent training without pay, Gary hadn’t been able to pay his bills. Now he didn’t have any savings to fill in the gaps between periods when he could get work with the call center.

  Whatever happened, Gary knew that some had it worse. He’d kept in touch with a few of the other call center workers who had been in his virtual training course. Some told him they were being paid $3 or $4 per hour, which meant their managers—most likely also contractors—were keeping a large percentage of their wages for themselves. It wasn’t as though an employment relationship would necessarily have prevented wage theft. But in the gig economy, paying $3 or $4 per hour to independent contractors was legal (as long as you were truly treating them as independent workers). They were not protected by minimum wage laws, which in 2016 mandated $8.00 per hour in Arkansas. “I don’t care how many hours you’re getting,” Gary said. “$3 per hour does not pay bills.”

  Terrence agreed. Samaschool was teaching people to apply for jobs, but it was difficult to actually get the job without the requisite skills. So Terrence made a suggestion for the next class cohort: Teach students not only how to use Upwork, the gig economy platform, and how to promote themselves, but also some skills that could help land a job. Samasource agreed on the strategy, and Terrence taught classes on virtual assistance, customer service, and social media marketing to the students who signed up for his next ten-week course. Still, only 2 of 21 people who enrolled found virtual work.

  For the next cohort of students, Samaschool decided that Terrence’s class would focus on learning one particularly valuable skill. The organization had done an internal analysis to decide which skill it would be. Social media seemed like a sweet spot: Many small businesses recognized they didn’t know how to use social media and didn’t have a strategy around it. They were looking for part-time workers who spoke English as a first language, the work could be done remotely, and it paid relatively well.

  The problem was that the job required constant creative thinking and meticulous writing skills, and these requirements did not match well with his students’ experiences. “We’ve been doing physical labor,” Terrence said, “where you get a job and obey what your boss tells you.” This experience was, once again, a lot to overcome in a ten-week course. But the factory and retail work that many of his students were more accustomed to, Terrence knew, was in the process of disappearing. Sometimes when he went on his six-mile walks, he thought about this—about what might happen as machines continued to take over those jobs. What the hell was Dumas going to do? He wasn’t ready to give up on the gig economy.

  Samaschool adjusted its curriculum yet again. Rather than having students look for work on Upwork, Samaschool recruited small businesses to hire students as interns at the end of the program.

  The arrangement was more motivating: Students got paid for their work ($300, most of which was paid by Samaschool), and they felt as though they were interviewing for a job. They developed social media strategies that Samaschool hoped the businesses would eventually hire them to execute. But after two rounds of classes and 13 graduates, just one student went on to complete additional work for the business at which she’d interned. Attendance and enrollment started to dwindle.

  When I visited in late 2015, I arrived at one of Terrence’s classes at 6:10 p.m. It was supposed to start at 6:00, but the big, interactive classroom was empty, and I found Terrence leaning on a railing outside.

  “I don’t understand what is happening,” he told me. He had just hung up his cell phone after speaking with one of his students, who had a headache and wouldn’t be coming to class. Another student was watching her son’s football game. “This has never happened before,” he continued, tears of frustration welling up in his eyes.

  Terrence was the kind of teacher who counted the extra work he did in days rather than hours. Of course he had all of his students’ cell phone numbers. And he started to vigorously put those numbers to work, dialing or texting as was age appropriate. He called a community college student first. Did she think that the curriculum was too hard? Were they cramming too much into one day? She thought so. He recorded the call to replay at a meeting with Samasource. A woman who worked at a tobacco superstore finally showed up to class—she was resting when Terrence telephoned and woke her up—and he asked her the same questions. She was a mother of five, she replied. Of course she could handle the curriculum.

  Before I left Dumas, I went to the downtown pharmacy to buy a snack. I sat in a booth with a pickle and some potato chips and watched as white people came and left through the front door while black people used the back door. Every once in a while, someone interrupted the pattern. But though it was no longer mandated, it was still there.

  An older black man wearing a purple plaid shirt shuffled in through the back door and picked up his prescription at the counter. “Is this seat taken?” he asked me. It was not, and he sat down.

  He asked me if I was from “the North,” and I said that I was. I asked him if he lived in Dumas, and he said he used to, until his landlord raised his rent and piled all of his belongings in his front room.

  It is supposed to rain tonight, he said, and I asked him if that were a good thing—if the fields needed it. He responded by summing up the basic problem in the gig economy and the economy in general. “Some people got enough,” he said of the rain. “Some people have too much. Some people don’t have anything. That’s just how it goes.”

  CHAPTER 9

  THE GOOD JOBS STRATEGY

  Having pivoted away from condo maintenance just six weeks earlier, Managed by Q launched its office cleaning and handyman service in April 2014. Shortly later, Saman, Emma, and Dan began doubting whether the model they’d chosen—hiring subcontractors to do the cleaning—would work as well as they’d hoped.

  Hiring independent contractors had proven to be a great strategy when it came to building the software part of Managed by Q. Saman had worked with a team of freelancers who lived in Argentina to create the first Managed by Q iPad app. They were easy to work with, and the app worked well. Ensuring the cleaning part was done well every day, though, had turned out to be more unpredictable.

  Managed by Q had promised its clients detailed, personalized service. One of its “positive touchpoints,” called “knolling,” involved arranging every item on a desk in 90-degree angles, making it look like a well-organized tool bench. Office managers would, according to the pitch, see the same cleaners every day, and they’d be able to customize their service—for example, by indicating the way that their chairs should be arranged—through the iPads Managed by Q installed on their office walls.

  As Managed by Q started cleaning its first offices, it learned that customers indeed wanted their chairs arranged in a particular way. They also wanted their pillows arranged a particular way on their lobby couches, and their coffe
e machine cleaned with a particular soap. Managed by Q communicated this feedback to its cleaning company’s supervisors, but the messages didn’t always translate into meticulous service.

  Managed by Q had partnered with janitorial companies to provide office cleaning staff rather than hire workers directly. And to cleaning industry veterans, some of the requests its clients submitted looked nitpicky: In a 10,000-square-foot office, was Managed by Q really going to worry about the pillows?

  After working all day at the Managed by Q office, Emma spent most of her evenings at clients’ offices, checking to make sure that the cleaners had incorporated all of the feedback that companies submitted through their iPads (which had to be relayed to the cleaning companies’ supervisors in emails). It wasn’t just a matter of checking details that kept her busy. Sometimes cleaners didn’t show up, and she’d have to call reliable cleaners to fill in for them. Sometimes nobody brought a mop, which meant a late-night trip to Home Depot.

  All of this was a problem, because to make its business work, Managed by Q’s service truly needed to be perfect. Saman, Dan, and Emma knew that most cleaning businesses had a lot of what the business world calls “churn.” Customers quit frequently, and companies spent too much money trying to recruit new ones. This included gig economy cleaning businesses. Homejoy, for instance, reportedly spent a fortune on customer acquisition and struggled with customer retention. To attract customers, it advertised deals that sold its services at an extremely reduced rate, in some cases offering first-time home cleanings for the dirt-cheap rate of $19.99. That expensive investment in new customers didn’t pay off. Journalist Christina Farr, at the time reporting for the website Backchannel, reviewed a third-party analysis of the company’s financials that showed only about a quarter of Homejoy’s customers continued to use the service after the first month, and fewer than 10% had stuck around for six months after they’d signed up.1

  Part of the pitch Managed by Q had made to investors was that Managed by Q would do better. “No churn! No way!” became an unofficial company slogan. But the only way to combat churn was to keep customers happy. That proved more difficult than the entrepreneurs had anticipated: Managed by Q lost its biggest client after about a month. Around the same time, Emma and Managed by Q cut ties, and Dan took over cleaning operations.

  Motivating “operators,” what Managed by Q called its frontline workers, to do a better job became a priority. The first step was getting to know them. On a Saturday, the entrepreneurs invited everyone to the office for pizza. Saman and Dan gave updates on new iPad features (like one that provided photos of exactly how the pillows on the couch were to be arranged) and recognized operators who had performed well. By the second or third “assembly,” instead of 10 to 20 cleaners, there were 60 to 70 of them. Dan and Saman raffled off prizes, including an iPad.

  Getting to know the cleaners felt right to the founders, but it didn’t automatically solve their problems. For one thing, the closer Managed by Q got with its cleaners, the more awkward it became with the cleaning companies, which felt the startup was overstepping its bounds. The operators weren’t Managed by Q’s employees, after all. And the assemblies weren’t exactly making the service suddenly easy to run. Potential disasters still emerged with exhausting regularity.

  In Emma’s absence, Dan found himself spending a lot of time putting out fires. When a client suspected that a Managed by Q operator had drunk the company’s liquor, he jumped on a motorcycle with a bottle of whisky. When another startup complained about how Managed by Q stored cleaning supplies at its office, Dan showed up on a weekend and built storage shelves. When cleaners didn’t show up for work, he and Managed by Q’s other first employees finished the day working at their own office and then went to clean for their clients at night.

  Elsewhere, Uber-like companies were having similar trouble delivering a perfect experience. By the end of 2016, the Better Business Bureau in New York had received more than 350 complaints about Handy, a gig economy cleaning company, and 186 of them were related to problems with service. It wasn’t that all of Handy’s cleaners did a terrible job, but rather that customers didn’t know what to expect. The startup’s Yelp reviews swung back and forth from one extreme to the other. It had more than 2,000 five-out-of-five-star reviews and almost 1,000 one-star reviews, with some Yelpers raving about “Tito C.” or “Ranu T.” and others telling horror stories about theft, sporadic quality, and annoyance at different cleaners showing up every time.

  Many “Uber for X” companies had, like Handy and Managed by Q, taken on services that were more complex than Uber’s job of getting customers from point A to point B. Their workers stepped into people’s homes to clean, picked up deliveries from restaurants that may or may not have been running on time, and completed a myriad of errands. It was more difficult for them to provide perfect service.

  Assemblies had helped give Managed by Q a better idea of the challenges its operators faced and a way to provide some coaching, but they didn’t meaningfully change their operators’ jobs, which Managed by Q’s founders were starting to suspect weren’t great. Managed by Q finally asked the subcontractors what they paid their cleaners, and it turned out in some cases to be barely minimum wage. This was consistent with what Emma had learned when she’d cold-called dozens of subcontractors to recruit them as partners. Most were cagey about how much they paid their cleaners. They’d stumble over the amount, refuse to provide it, or say something like “Well, on the books or off the books?” It was clear that office cleaning work in New York, outside of the unionized jobs in skyscrapers, was not a great gig.

  This was troubling to Dan and Saman for business reasons—without controlling compensation, there were few good ways to motivate and train workers—but also for personal reasons. Neither Saman nor Dan was interested in starting a company that offered crappy, low-paying jobs.

  Starting a tech company is very likely to involve stress, insane hours, and shattered dreams, and not very likely to succeed. A sense of bigger purpose is one of the more logical reasons for launching a startup, and it had been a factor for both Saman and Dan.

  The advertising campaigns Saman had worked on before becoming an entrepreneur sometimes attracted attention. His most famous was the “Whopper Sacrifice,” a Facebook app that rewarded people with a free Burger King sandwich if they “de-friended” ten people. But in 2009, as the United States slipped into a recession, Saman didn’t feel he was doing anything meaningful by trying to get people to buy cars and hamburgers, and nothing drove this home like trying to describe these efforts to his grandmother. In order to translate a description of his projects into Farsi, he had to simplify them to their most basic components and language. Hearing them that way made them sound stupid.

  It wasn’t all altruistic, this desire to make an impact. It was more of a desire to make something permanent, as opposed to the ethereal ads he had been working on. It was at least partly driven by ego.

  When Saman’s wife got a work assignment in Japan, he had quit his advertising job and gone with her, and from their apartment in Tokyo, he had started a labor marketplace that launched in 2010. It was designed to “rid the world of unemployment” by connecting “Lawyers, Painters, Babysitters, Bakers, Photographers, Tutors, Typists, Copywriters, Plumbers, Party Planners, Programmers, Artists and Actors” with people who wanted to hire them. “While it’s true that employment opportunities in the traditional sense are not what they used to be—and may never be again—there is still plenty of opportunity for motivated individuals with exceptional skills to build a sustainable and thriving freelance career,” Saman told a tech blog.2 It was the gig economy before anyone called it the gig economy. And like many pieces of the gig economy, it grew out of good intentions, and perhaps some naiveté. He named it Tischen, a take on a German word for “table” (and a name, he realized in retrospect, most of his target customers couldn’t pronounce). Although Tischen never took off, the project had brought him into the world of entreprene
urship, where he’d felt at home ever since.

  Dan, Saman’s cofounder, had similarly been driven to startups by a mix of ego and a desire for meaningful impact.

  This had started as a kid, when he told people that he wanted to be president. It had continued through high school, as he largely ignored his schoolwork and directed attention instead toward pursuits like protesting the class trip to Disney World (he’d read that Disney used sweatshop labor, so he planned a Habitat for Humanity trip instead).

  The summer before he left for college in 2007, Dan drove with his girlfriend (a senior at Princeton) and his brother to hear then-senator Barack Obama speak at a concert venue in Philadelphia. As Obama led the crowd in a chorus of “Happy Birthday” for the local celebrity who sang the national anthem, Dan was struck by the sense he was seeing a different kind of politician. Obama described a US population with families that “can’t figure out if they should fill up the gas tank, or whether they can save for their retirement or for sending their children to college” and where 45 million people went without health insurance. He spoke of “a very simple idea that we all have simple obligations to each other.” Dan found himself nodding along. “Instead of people taking responsibility,” Obama said, “what we end up with is folks trying to blame somebody. Blaming the other party. Blaming immigrants. Blaming gay people. Always finding a reason for why we can’t do something. And that is why I think so many people are turning out all across the country.”3

  Dan felt inspired. He wasn’t the type to preach hope and change, but he wanted to make a difference, if for no other reason than he didn’t really believe anyone else could do a better job. Hope and change were in the air. You could feel it. You could touch it. It confirmed his desire to become a politician who worked on social issues.

  His first plan for after college was to join the military—become a naval officer before running for public office. He already had a start date for basic training when he fell for an opponent’s fake during a rugby game, tore his ACL, MCL, and meniscus in a single fall, and ended up a paralegal in New York City instead. He didn’t like working in law—making an impact was too slow of a process that involved much too much paperwork—and, by extension, he’d put his goal of entering politics on the sideline. But he still was interested in social issues.