Gigged Read online

  At TechCrunch Disrupt, Dan and Oisin clutched bottles of conference-branded water and crossed their legs, each resting a foot on a knee. Rather than answer the question about whether the gig economy was over, Oisin argued over semantics. These new developments shouldn’t be called the gig economy, he said, punctuating every beat with his free hand. What they really do is remove friction from business transactions. He hadn’t exactly suggested a new name for the gig economy, but the moderator joked about the “frictionless economy.”

  “Dan, what do you think of the new name?”

  Dan shrugged with his hands. “Oisin makes a good point,” he said.

  The conversation did not become any more direct from there. Oisin, who in public appearances could sound rehearsed, as if he were reciting a political speech, repeated the “gig economy is flexibility” mantra. Dan, a bit more natural on stage but still sticking to his talking points, recited his Good Jobs Strategy spiel. Oisin attributed the lawsuits Handy has faced to “lawyers who want to make a quick buck.” Dan noted that there’s no reason that flexibility has to mean that workers give up the protections of being an employee—there’s no law stopping companies from letting employees pick their own schedules.

  It was the same conversation they had been having separately for years. But the businesses they’d built around it had completely transformed.

  Managed by Q had raised another $55 million in funding and begun rolling out a new portion of its business that functioned more like the gig economy. Office managers could use the feature “marketplace” to order services like office staffing, catering, maintenance, IT help, and cleaning. Though Managed by Q still had its own office operators in New York, Los Angeles, and Chicago, this new product worked a lot like the first version of Q, with small businesses, rather than Managed by Q employees, handling the work. So far, about 200 businesses had signed up to sell through the platform.

  Q’s marketplace wasn’t quite an Uber-like experience. In some ways, it was more like Yelp: Clients browsed profiles of the small businesses to make decisions about who to hire, and they could hire the same company repeatedly if they liked the service, while workers were typically employees of the small businesses rather than independent contractors. But Managed by Q did take a 10% to 20% cut of the bill when office managers ordered services using the marketplace, similar to the way that Handy and Uber take a cut from their independent contractors. In newly launched cities, Managed by Q had not yet decided whether it would hire its own operators or whether it would merely use its technology platform to connect offices with small businesses.

  Managed by Q had proven that a cleaning and handyman company could be profitable while treating its workers well. What made it attractive as a technology company was that it could expand by routing work to other businesses.

  Handy, meanwhile, had installed a new training process for cleaners that could be completed entirely online and added more automated layers to its customer service lines, both of which had cut down on the cost of acquiring cleaners and customers. It had, according to the Inc. article, stopped speed-scaling and focused instead on building a critical mass in the cities where it already operated.

  Throughout this process, the company’s executives continued to advocate for new laws that addressed its on-demand workforce. Though their efforts toward an on-demand-worker bill in New York State had not resulted in policy changes, its executives remained vocal about what they saw as archaic laws that prevented them from offering workers more support. The problem, Oisin had argued in a Wired op-ed headlined “We Must Protect the Gig Economy to Protect the Future of Work,” was that “the current regulations never contemplated these new ways to work.”7

  Why hadn’t Handy, Jon wanted to know, been more vocal about the dismantling of the Affordable Care Act? After Donald Trump was elected president, congressional Republicans made it clear they planned to repeal the US law, which made it easier for the independent contractors that Handy relied on to buy their own insurance. Oisin didn’t answer the question. “There’s a massive amount of uncertainty,” he said.

  But doesn’t this effect your workforce? Jon asked Oisin about the Affordable Care Act.

  “It’s a very serious issue,” Oisin said, dodging the question for a second time.

  Jon’s next very direct question essentially amounted to: Isn’t the gig economy a way to take money from frontline workers and turn it into profits for tech entrepreneurs?

  “I think we are in danger of that, but we are all actively working to solve that problem,” Oisin said. He seemed to be referencing the drafted New York State bill Handy had circulated a year earlier, which proposed a safe harbor for gig economy companies that contributed to workers’ benefit funds. Months later, Handy would lobby—successfully in some states—for legislation that similarly protected it from misclassification lawsuits, but did not include any requirement to create benefits for workers.

  Handy wasn’t the only gig economy company that talked about efforts to improve the experience of workers on their platforms. Care.com, a website for hiring nannies, babysitters, and other caregivers, with 26.4 million registered users worldwide, had, for instance, experimented with a benefits platform that took a percentage of transactions paid to workers and put it into a fund that workers could use to pay for healthcare, sick days, and other benefits. Uber had also experimented with the idea of a portable benefit. It structured one pilot program somewhat similarly to the Black Car Fund in New York, which provides more than 70,000 livery drivers—typically, like Uber drivers, independent contractors—with workers’ compensation insurance via a 2.5% surcharge on every ride. The customer pays into the fund, rather than the dispatcher. Uber’s version raised rates on some rides by about 5 cents per mile and gave drivers an option to put that additional 5 cents per mile into a benefits fund that in the event of an accident would cover medical expenses, lost income, or survivors’ benefits.

  Additional startups had meanwhile rushed to fill in some of the security that work increasingly lacked. An app called Even helped employees with unpredictable schedules plan for the uneven income. Whenever a worker was paid less than her average, Even deposited extra money in her account, interest-free. When she made more than her average, Even paid itself back. It created the semblance of steady income. Even eventually partnered with Walmart to give employees an option to receive part of their paycheck before their two-week pay period was over, helping them avoid payday loans if they faced an unexpected expense. Another startup called Honest Dollar provided retirement savings accounts for independent workers. It offered a $5 monthly discount to drivers for Lyft, which introduced it in a blog post as “an easy, affordable investing platform built with independent contractors in mind.”8 (Goldman Sachs acquired Honest Dollar four months later.)

  An organization called Peers.org aimed to collect these sorts of services onto a single platform and to entice companies to participate by contributing to benefits like healthcare and retirement savings. “You know when you start a new job, and they hand you a folder filled with all of your benefits, and it’s not scary?” its director at the time, Shelby Clark, asked me. “Like that, but in an app.” Clark later said he hadn’t found many companies willing to divert pay into worker funds. Most startups had been afraid that participating would make them susceptible to misclassification lawsuits. (Peers eventually merged with another organization that advocates for on-demand workers.)

  The problems with many efforts that aimed to close gaps in security for workers were, first, that their results paled in comparison to the security of a traditional full-time job with benefits, and, second, that they involved a choice. Companies that hired independent contractors could choose whether to participate in a benefits fund like the one Peers.org had envisioned. They could choose to ensure contract workers were paid at least $15 per hour, as Facebook does. And they could choose whether to listen to workers’ complaints or to listen to workers at all. All of these were choices that, given customer d
emands for dirt-cheap service no matter what the cost to workers and the threat of misclassification lawsuits, companies weren’t likely to make.

  Contract work, freelancing, and outsourcing can all involve good treatment and compensation. But relying on good actors to make decisions that benefit workers is not a scalable solution. While the Good Jobs Strategy may have been successfully embraced by companies like Managed by Q, one need only take a look at how many employees have access to sick days (65%) and paid family leave (13%)—neither of which is mandated by US law—to see that the strategy doesn’t cover everyone.9 There may be a way to make good jobs a profitable choice, but there will also always be some employers who don’t choose it. In the gig economy, those employers have very few mandated obligations to workers.

  Fixing this problem involves more than cracking down on companies that cheat workers by incorrectly calling them non-employees. The gig economy has, in addition to creating gray areas of control, expanded the ranks of the legitimately independent. Gig work platforms that target a particular industry, like Gigster, where Curtis signed up to work, deliver specific expertise on demand. And those like Mechanical Turk make it possible to chop jobs into individual gigs and disperse them to a crowd. It’s easier than ever to get work done without hiring someone as an employee. But the growing group of non-traditional workers that results has no access to labor protections or safety nets provided by law to employees. And all of the misclassification lawsuits in the world aren’t going to change that.

  At TechCrunch Disrupt, the conversation between Dan and Oisin ultimately turned to this bigger structural problem. As Jon started moving on to the next question, Dan interrupted to give his own answer to the question of whether the gig economy was just shifting profits from frontline workers to employers. Though the (now former) secretary of labor had a year earlier told Managed by Q’s employees that their efforts were building the middle class in America, Dan pointed elsewhere. “I think we have to be eyes wide open to the reality that we live in a world where wealth perpetuates wealth and poverty perpetuates poverty,” he said. “There’s a big conversation to have about how to build the middle class in America, and I don’t think that it’s honestly something that Oisin and I can solve.”

  EPILOGUE

  Wealth perpetuates wealth, but in-demand skills do, too. Curtis Larson, the New York City programmer, didn’t pay much attention to debates over the gig economy, though he shared the independent contractor status of Uber drivers and Handy cleaners. He had no reason to pay attention, because the gig economy worked great for him.

  His success was just as true as the Dumas program’s failure. Curtis had worked hard to set up his small freelancing business on the site Gigster, and it regularly routed programming jobs to him. He was able to maintain his previous wage and live the flexible “vacation on a moment’s notice” lifestyle that had lured him in the first place. And yet, the last time I talked with him, in July of 2016, he was about to sign an employment contract with Silicon Valley’s golden child, SpaceX, a Los Angeles–based startup created by Elon Musk that builds rockets and spacecraft. It was a surprise to both of us.

  “It’s the only company I would want to work for instead of freelancing,” Curtis said. “It’s pretty much a dream company.” On a live video feed in 2013, he’d watched SpaceX test its first reusable rocket, Grasshopper, and he’d kept tabs on its progress ever since. The work SpaceX did seemed more meaningful than most of the startups he’d been exposed to, which worked on new ways to serve online ads or advertised themselves as Uber for delivering pet supplies. “We don’t know very much about anything outside of Earth; space has the biggest mysteries of life,” Curtis said, before admitting a beat later, “and I just think it’s really cool.”

  Working at SpaceX had been Curtis’s dream: something he thought about in an abstract way but never imagined would be a realistic option. Then, one day in May, he had finished his freelancing work at the coffee shop and realized something had changed. He’d spent the last year teaching himself, through freelance work, how to tackle a broader range of projects. And suddenly he felt qualified. He filled out the online application.

  He was shocked when SpaceX called him back. Three technical phone interviews later, he was flying to Los Angeles to meet the team in person. The software engineers worked on the same campus as the engineers who were building the rockets, and on the factory tour he saw the shop space where they built rocket bodies and the clean rooms where they worked on electronics and space suits.

  Curtis wouldn’t earn as much money at SpaceX as he had as a freelancer, and he’d been warned that SpaceX employees worked a hard schedule—about 11 hours per day, at a minimum. The snacks didn’t even stack up to those at his last full-time job. But he’d be working on space travel.

  The time Curtis spent freelancing had provided him with not only the new skills he needed to land his dream job, but a new sense of security. “If I really don’t like working for them,” he figured, “it will be really easy to quit and go back to freelancing.” He might even pick up an occasional project on the weekend, if he got bored or just needed some beer money.

  This is why then–Uber CEO Travis Kalanick had called the gig economy a “safety net.” For Curtis, it really was.

  * * *

  Forming a cooperative version of Mechanical Turk started to look less feasible for Kristy as she continued her education. She didn’t love academia, and she no longer wanted to get a Ph.D., which had been the context in which she had planned to build the platform. At a conference, she’d run into the founder of a digital cooperative called Fairmondo, and he’d told her that he thought he’d be running it forever.

  That made her pause. Kristy didn’t want to run a platform forever. She also didn’t want to be poor forever. Her husband wouldn’t be able to work into old age doing physical labor, and she had much less time to make money before retirement than her 20-something classmates.

  After finishing her master’s degree in labor studies, she decided to become a lawyer. I visited her in Toronto the week after she took the LSAT. We sat in her apartment living room, under a huge poster of Paris, while her dogs yapped in the other room. “Stop!” she’d shout at them every once in a while, which seemed to calm them down, as though they had only been inquiring whether she was still there.

  Just before the LSAT, her arm injuries started acting up again. She worried about holding a pencil for the test. Her husband had in the meantime named her elbow brace a “Mechanical Turk badge of honor.” She’d avoided painkillers out of fear they would impact her ability to study effectively.

  Though she was still nervous about how she’d done on the test when I visited, she ended up scoring well enough on the exam to earn admittance to two Toronto law schools. As a lawyer, she was hoping she’d be able to advocate for workers and make money at the same time—that she wouldn’t have to give up what, perhaps, was one of her greatest talents: “I say things that people don’t want to hear,” she explained. “I say them loudly. And I say it to their face so they don’t miss it.”

  * * *

  By the summer of 2017, Abe had put all things Uber aside. After the strikes and his last-ditch attempt to sell his silence to Uber had failed, he decided to start his own ride-hailing app called A-Ryde. He spent money promoting the idea at a conference and filming a commercial (“Woaaahh, let’s not ruin this night with surge pricing,” a hip young man tells a friend who presumably is about to use a different ride-hailing app). When Abe couldn’t raise enough funding to launch the app, he tried to sell his house to finance it (given that a lien had been placed on it, that didn’t work).

  Since then, he’d realized that the thought of competing with Uber, a startup with billions of dollars in funding, had always been a fantasy. Abe told me he’d grown a lot as a person since the days of Uber Freedom. He’d stopped falling for get-rich-quick schemes and started saving as much money as he could to buy more real estate. It would be real estate that would eventual
ly make him a millionaire, he believed now. And yes, he’d found real estate gurus online, but none of them had asked him for money the way that Kevin Trudeau had or requested a percentage of each of his transactions, the way Uber had.

  A $25,000 lawsuit settlement payment from a former employer allowed him to buy his second house and start collecting rent. His plan was to buy one house a year, until he could become “financially free.” In case that didn’t work, he’d started investing in Bitcoin.

  Donald Trump’s election, Abe believed, boded well for him. Abe had heard that the new president would pass laws beneficial to real estate tycoons. And he liked Trump’s intentions to cut taxes on corporations. The way he saw it, both of these things would benefit him and his mission to become a millionaire.

  Considering Abe’s attitude toward credit card bills, which he told me he never paid, it seemed likely that his credit was completely shot. No bank would ever give him a loan. No credit card company would ever extend him a line of credit. He was probably being hounded by debt collectors, he said, but he’d installed a call-blocking app on his phone, so he wouldn’t know.

  Abe tried to work every day so he could save the cash to buy houses. All in all, he couldn’t say he regretted believing that GIN would make him a millionaire or believing that Uber would make him a business owner. It had taught him that the only path to financial freedom would be hard and slow, and that he shouldn’t believe people when they told him otherwise. The idea that he would always need to work crappy service jobs in order to make a living, that he would never become a millionaire, still wasn’t one that he was even willing to entertain. “I know that for sure, without a doubt, before I turn 40 I will do it,” he said.

  In the meantime, he planned to keep saving. He’d try not to spend any money. Every small purchase he made was another hour he would need to spend at work before becoming financially free.