What if You Could Outsource Your To-Do List?

“In mid-April, we had to let forty per cent of our company go,” the director of revenue operations at one mobile-commerce startup told me. “Before, we probably had ten people doing the work—but the reality is that Invisible is doing such a good job, and we’re seeing such cost efficiencies, that post-coronavirus we’re maybe not considering employing for these tasks again.”

In a spirit of adventure, I signed up with Invisible myself. Over e-mail, I was introduced to my new assistant, William Blake. (Not my favorite poet, but whatever.) I had planned to ask for his help transcribing an interview, but I faltered at the crucial question. How to address him? “William” felt ludicrous. “Blake”? Unfair to art. I settled on “Mr. Blake”—appreciative and respectful, like Mr. Darcy, Mr. Robot, Mr. Shawn—and wrote him a long, solicitous set of instructions. An eighty-five-hundred-word transcript came back the next day.

Invisible’s executive-support clients are required to spend at least two thousand dollars on services per month. This is not cheap, though it’s worth noting that a full-time-ish assistant somewhere like New York costs much more. Hayley Darden, the company’s marketing director, advised me to regard Mr. Blake less as a personal assistant than as a process assistant: not good for random errands—such as haggling with Verizon customer service—but excellent with repetitive, mind-numbing chores. “Whatever you most hate doing in your life is perfect,” she told me.

I decided to assign Mr. Blake one of my saddest tasks, filing expenses. At The New Yorker, this is done via a cryptic online platform. I walked through the rigmarole with Sam Mata, one of Invisible’s “delivery managers.” He works from his home in the Dominican Republic, meeting with new clients to gauge their needs—a conversation that Invisible calls “discovery,” and that often has a therapeutic mood. (In workflows as in life, people rarely see the heart of their problems clearly.) Did I want receipts filed separately, or in bundles? Mata asked. And how often should Mr. Blake check for new ones? Darden had explained that a first-rate assistance operation would intercept the work before it even reached my radar screen. Ideally, Mr. Blake would log in to my e-mail account, look for receipts, and file them on his own.

Log in to my e-mail? I had visions of my not-favorite poet pawing over inchoate notes I’d sent myself, weird forwards from Mom, love letters I’d received in the Obama years. I could hear him snickering over embarrassing purchases, such as—just to give an extremely hypothetical example—a twenty-five-minute sleep meditation narrated by Diddy. Not to fear. The agents would use a secure-key client and never see my passwords. And, I was assured, their bosses would be watching for any funny business.

The next morning, I sat down at my desk to find ten e-mails from the dreaded New Yorker expenses portal: my submissions had been approved. My personal dashboard on the Invisible site revealed a breakdown of the job by unit cost (rounded to $1.83 per expense) and total ($27.50). I felt as if someone had broken into my home and scrubbed my bathroom while I slept. For all the quantitative specificity, though, I couldn’t see the names of the agents who had worked on the job behind Mr. Blake’s façade.

Next, I arranged for Mr. Blake to book my meetings. Mata sent me templates for Mr. Blake’s e-mails, which turned out to be a dangerous overture; my writer’s compulsions kicked in as soon as I opened them. Mr. Blake made first contact by writing:

Hello [Name],

Happy to help you and Nathan connect. Below are suggested . . .

But did “Happy to help you and Nathan connect” maybe sound slightly grudging? With that phrasing, it was easy to envision Mr. Blake as a twenty-four-year-old Bard graduate, cooler and smarter than me, returning to his three roommates each night with stories of his effete boss, Nathan, who was incapable of scheduling his own meetings and who needed to have everything printed out. I changed it to:

Delighted to help you and Nathan connect.

This had the ring of job contentment. I spent fifteen more minutes turning the sentences around before going back to my work. Ah, efficiency.

A few days later, I Zoomed with Prabhat Hira, an agent who had worked on my expense filing. He was based in New Delhi, and appeared in a collared jersey for the Gryffindor quidditch team. “The delegations I worked on for you were kind of exciting!” he said—the most enthusiasm for expense filing that I had ever heard. Hira had started working as a freelancer online in order to spend more time at home with his young family. He spoke fondly of his “journey through Invisible” and, like all the workers whom I met, described the company’s collegiality. “It feels really good to talk to people from different countries, from different cultures,” he said. Still, most of the people he was talking to were other agents. During the nearly three years he had worked at Invisible, Hira told me, I was the first client he’d ever met.

For a long time, the de-facto genre of assistantship stories was comedy, because societal roles were thought to be fixed, and straining against the order of things had funny outcomes. Malvolio, the imperious steward in “Twelfth Night,” chafes against the limits of his station and gets punished with ugly socks. P. G. Wodehouse drew on a long tradition of stories about clever servants acting beyond their master’s ken: Jeeves and Bertie Wooster are crossed by the order of things, the boss set to task and taste by his assistant, and the injustice is comic because both of them are powerless to correct this misarrangement.

In the middle of the twentieth century, the old nonsense about class and station started to fall away in the West. With the turn toward supposed meritocracy, a different literature of assistance emerged. Recent stories look more like bildungsromans; the transgression of roles is where the drama, not the comedy, comes through. “The Devil Wears Prada” and “Clouds of Sils Maria” are narratives about assistants becoming or choosing not to become, and about bosses who watch their pasts replay from the far side of life choices that they can’t reverse. Assistance may be where people start out, but it is no longer necessarily where they end up, and that knowledge makes for friction in the daily grind. The curse of opportunity is the mandate to be always striving.

And so, just as many assistants have been slightly terrified of their powerful bosses, a number of powerful bosses now appear to be slightly terrified of their assistants. Business kingpins fret over being sold out. Luxury-industry leaders worry about assistants absconding with goods or money. A surprising number of Hollywood types seem to share a fear that their assistants will experience a Norma Desmond moment and attack them with a weapon. In theory, Invisible’s assistance presents no such human perils. Pedraza can be sure that John Keats isn’t trying to take his job, embezzle, or have sex with strangers in his favorite chair, because John Keats is just a big tin man of fragmentary shared processes and incoherent passions.

In practice, though, the mandate to strive is spread across the globe. Even before COVID-19, Invisible had no office, and not long ago I went to visit Pedraza at his apartment and operations center in Brooklyn, a shimmering, Jenga-like glass tower on the East River. In deference to the pandemic, I had proposed a virtual meeting. But Pedraza, who described himself as being “risk-friendly,” preferred something more personal. In the lobby, one doorman guided me to another doorman, who guided me to a large elevator bank, and I went up.

The apartment where Pedraza leads a growing empire of work was not much larger than a college dorm room. The kitchen spanned a counter near the door. The rest of the space was dominated by a platform bed with an uncovered duvet.

“Sometimes I have guests here. I’ll cook a meal,” Pedraza told me. It was nice to imagine. He sat down by a desk. He was wearing a black shirt, white shorts, and white canvas shoes. I sat on a small gray couch. There was one window—the death-prevention kind that opens only a few inches.

Pedraza grew up in San Diego, with parents who come from immigrant families. (His mother, a former entrepreneur, is Persian; his father, an architect by training, was brought up largely in Venezuela and Japan.) When he was in elementary school, he was bullied. “I was ready to be friends with everybody,” he told me, “but I wasn’t willing to go through the hazing rituals of ascending the hierarchy.” At twelve, he enrolled in a five-year Skype course on “the great books of Western civilization” and his world changed. He learned to inhabit a private order drawn from books and personal dreams. On his darker days, he identified with Don Quixote. On brighter days, too. “The most wonderful and exciting future is one in which as many individuals as possible are expressing as much of their potential as possible, and everyone has their own ideas about what the future is going to look like,” he said.

Pedraza went to Cornell with high hopes, but the giant lectures vexed him. He spent a year abroad, at Oxford, and liked its one-on-one research tutorials. Back in Ithaca, he started a line of Livestrong-like bracelets that he called DoBands. Wearers would commit to doing something, such as running a marathon, and, when the task was completed, log their achievement in an online database and pass the bracelet on to someone else. When Pedraza graduated, he moved to Palo Alto and tried to launch a social iPhone app to help people achieve personal goals. He found no investors until he lucked into an introduction to the venture capitalist Peter Thiel, who invested fifty thousand dollars; $2.5 million in additional funding followed. The app was called Everest, and it had around half a million downloads, but the company failed after three years. “The fatal flaw,” Pedraza told me, “was that people would quit working on their goals.”

“Thanks to the effects of time dilation, only three days will have passed for us, but when we return to Earth the Trump Presidency will have just ended.”
Cartoon by Darrin Bell

Invisible is plainly oriented toward its clients’ achievement, but Pedraza believes that it helps its workers along, too. He’s an advocate of employee-owned business; fifty per cent of Invisible is currently in the hands of its staff. If agents in distant countries show outstanding initiative, he says, they can take equity, too. So far, only two out of two hundred and seventy-nine have reached his standard, but he holds out hope for the rest. He told me, “Invisible in its very, very long-term strategy is sort of a back door into an education company.” He means that it can serve as a kind of school: Invisible offers skills that, in theory, can be transferred to other desirable jobs. Nadine Jost, an agent in Pretoria, told me, “You have a test every week, and, if you test low, they will tell you that you need to be retrained.”

Although virtual characters like John Keats or William Blake make the interface accessible to individuals, the heart of Invisible’s business is churning through labor-intensive processes for small or medium-sized companies. “This is a juicy, juicy market,” Scott Downes, Invisible’s forty-nine-year-old chief technology officer, told me. Roland Ligtenberg, a co-founder of Housecall Pro, a business platform catering to home-service companies—plumbers, carpet cleaners, and so forth—uses Invisible to help coördinate the sorts of growth efforts that a young startup needs. “Being able to have an extra set of hands you can spin up at any moment is a huge competitive advantage—the reason being that you’re trying a lot of little things, and, once you see one working, you want not to just double down but to double down on the double-down,” Ligtenberg said. Without outsourcing, he’d have to undertake a round of hiring every time he wanted to start a new initiative—and a round of firing if it didn’t work out.

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