Startups Bet That Lonely Freelancers Crave Company

(Bloomberg Businessweek) -- A year and a half ago, Alex Schneider was struggling with two gigs. The 30-year-old has a startup that makes $29 cardboard standing desks called Ghostands, and also a remote job as a senior assurance accountant at HoganTaylor LLP. One day he came across a Reddit post that mentioned a productivity site called Focusmate. Intrigued, Schneider logged on and gave it a spin.

His daily routine was transformed, he says: Soon, his work-at-home days began promptly at 8 a.m. by turning on his laptop camera and saying hello to a “buddy” he’d been randomly assigned. The camera keeps rolling for 50-minute shifts while the buddies work. “Initially it sounds weird, but it’s great,” Schneider says. “It keeps me honest, in terms of waking up and being there.” He’s been struck by how friendly and helpful his buddies have been, he says; he’s encountered “no one crazy or outlandish.”

Welcome to the latest evolution in the saga of remote work. First came the rise of freelancers, and the simultaneous overpopulation of coffee shops. Then came the early-Aughts hackerspaces, which transformed into late-Aughts coworking spaces such as London’s Impact Hub GmbH (now with more than 100 locations in 50 countries). Specialized work clubs then emerged, like the women-only networking hub the Wing (now offering an array of professional and social activities in several cities) and HatchLab, a coworking outfit geared toward do-gooders in Portland, Ore. But these organizations don’t have nearly enough seats for the 57 million Americans who are freelancers, according to a 2019 study by Upwork and Freelancers Union.

Now a handful of young online coworking companies are blooming from the ashes of WeWork’s failed initial public offering, aiming to transform remote work into a group activity. The premise is simple: For people working alone, motivation and productivity can come from interacting with others. Focusmate and similar startups offer just that—company. “Coworking always promised that it would be inspiring and make your work better, but it turned out it was just space,” says Jeremy Redleaf, co-founder of Caveday LLC, a company that runs online group work sessions.

The companies lay on the productivity buzzwords thick: flow, accountability, connection, deep work, energy management, monotasking. They claim they don’t directly compete against one another, despite sharing a common goal of facilitating users’ best work in real time. And their approaches differ. At Ultraworking.com, logic-minded users can log four-hour “work cycles” together and fill out complicated spreadsheets marking their progress. Four hours scares off most Focusmate users, who are more comfortable with the 50-minute sessions.

“These companies are very slick,” says procrastination researcher Joseph Ferrari, a professor of psychology at DePaul University. Ferrari says group coworking probably wouldn’t work for the 20% of people who are chronic procrastinators—those who avoid all manner of tasks as a way of life. But for the other 80%, he sees promise.

“The strategy isn’t new,” says Joel Anderson, a psychologist at Utrecht University. In the late 18th century, philosopher Jeremy Bentham imagined the panopticon, a circular prison with a guard tower in the middle, so prisoners would perceive themselves as under constant surveillance and thus behave better. Now home-office jail is a daily reality for most people grinding out hours on their couches.

Anderson rattles off the psychological underpinnings at play in these work groups: mutual task reinforcement; shared focus; incentive not to disrupt; positive peer pressure. “There’s plenty of research about how we are much more likely to regulate our behavior when we are being observed.”

Support Groups

Caveday LLC

A “Bat” guide leads 3½-hour sessions on projects requiring deep focus, with motivational exercises. Offered on-site in Los Angeles and New York City (no phones allowed) and remotely.
 
The Pitch
“Our ethos is improving your relationship to work,” says co-founder Jeremy Redleaf, 35. “Cave life is doing a cave in the morning and having your afternoon to do other things.”
 
Origins
Redleaf took what he calls a “cave day” to work on a writing project in 2016. “It was really depleting to do it alone, so I did it with collaborators and realized that focusing as a group can be energizing,” he says. That led to hosting weekly Sunday caves in 2017. The first one sold out; last year, Caveday offered 370 caves.
 
Target Audience
● Independent knowledge workers
● Creatives
● New moms
 
Price
$35/month, unlimited remote
$50/month, unlimited in Los Angeles
$99/month, unlimited in New York
 
Investment
Funded by 1,200 regular users, plus a space-sharing partnership with Breather workspaces. Currently meeting with investors.
 
Cult Followers
TV actresses. Grace and Frankie’s June Diane Raphael and Saturday Night Live alum Casey Wilson appeared in recent online caves.

Focusmate Inc.

One-on-one 50-minute video sessions with randomly assigned partners, booked on demand. Users state their goals, then report progress at the end. Not just for work: Some users do yoga or clean.

The Pitch
To create “the most supportive community on Earth,” the company says. More than 300,000 work sessions have been held so far. “I just think we’re at a point in evolution where we can afford to evolve what work looks like,” says founder Taylor Jacobson, 34.
 
Origins
Jacobson took a remote gig, and his productivity withered. He and a friend started work buddy appointments on Skype in 2015: “Both of us just found it so helpful and supportive. That was the spark—this notion that you could get more help than maybe you thought you should be able to get.” Focusmate started as a Facebook group and has since attracted investors.
 
Target Audience
● Ph.D. students, freelancers, and remote workers
● The anxiety-prone
 
Price
$4/month unlimited
 
Investment
$1 million from funders including author Nir Eyal and VC funds Amasia and Betaworks.
 
Cult Followers
People with attention deficit hyperactivity disorder. “There’s a concept called the ‘body double,’ where just having another body there helps people with ADHD focus and keep from going off on tangents,” says Kim Kensington, a psychologist in L.A. “For people with ADHD, getting started is painful—it’s like starting a car with a dead battery.”

To contact the editor responsible for this story: Dimitra Kessenides at dkessenides1@bloomberg.net

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