inside the company nailing remote working

From the Summer issue of City AM The Magazine: inside the remote working company appealing to a new generation of digital nomads

Rows upon rows of cookie-cutter houses fill the boujee neighbourhood of Abbot Kinney in Los Angeles. In front of one, a basketball hoop stands by a double garage. It looks like all the rest, but this particular property is different. It is setting a new standard for digital nomad living.

It functions somewhere between an Airbnb and a posh hostel, with the bulk of the house made up of six private bedrooms built around a central co-working and socialising space. It is one of 50 properties around the world operated by Outsite, a company you’ve almost certainly never heard of that’s celebrating its tenth anniversary this year. This fact alone means it has succeeded where its competitors have not. Once upon a time there was CoBoat, the digital nomad community based from a boat; Remote Year, and Selina co-working hotels. Then there was the downfall of WeWork…

Selling somewhere to sleep and work with random strangers is a formula I hadn’t seen anywhere else. Despite 48 per cent of members earning more than $100,000 a year, Outsite has a vibe that feels almost studenty. House sharing seems to buck the conventional life-goal narrative, which dictates that the more successful you get, the quicker you inhabit your own home.

So I decide to fly to Los Angeles, where there is the highest concentration of digital nomads in the world (London has the highest in Europe), to meet the remote workers using Outsite.

“I haven’t seen this kind of remote working, co-living situation before,” says Hannah, who is in her thirties and from London. She is one of a handful of people I meet within hours of arriving, after being added to a WhatsApp group by Outsite’s property manager. She’s a freelance marketing consultant, currently based out of LA. She’d signed up for the year-long Outsite membership (£110), allowing her to book in at any of the properties around the world (for a fee, of course).

I soon meet up with another Brit, 36-year-old Mark, who has worked for himself for two decades as a business-to-business seller on Amazon. He tells me he has lived full time at Outsite for the past few months. “The other night we were talking about how we all own flats in the UK and here we are, living in this shithole,” he laughs. “It’s funny when you think about it.” To be fair, Outsite is far from a ‘shithole’ (Mark notes that the LA property is worth more than $3m) – the joke is that these are wealthy people choosing to live like students, part of the global rise in people choosing careers that aren’t centered around an office.

Our house includes a fabulous entertaining area and a kitchen island big enough to accommodate the whole cast of The Hills. Everything is intimidatingly white and a piece of aspirational art features the words “no bad days.” Pictures of coloured in animals hang on the wall like children’s artwork on a fridge door, only drawn by adults. Polaroids of guests are pinned to corkboards. “You’re sharing but most people are out all day, so you’ve kinda got the house to yourself,” says Mark. “Obviously if you’ve got a relationship and stuff you want your own space, but if you’re single…”

A room without a bathroom in my Los Angeles pad costs around £2,000 per month. That’s the same as renting a one-bedroom apartment in the same part of town with a kitchen and living space to yourself. My bedroom – ‘Walgrove’, named after a street in the local area – is a decent sized double with plenty of storage, a pleasant view over palm trees, and a bedside table. It’s what you might call minimalist. Next door is a (clean) bathroom with a bath, shower and toilet. I’m a fairly light sleeper so sometimes in the night I’d wake up hearing people opening and closing their bedroom doors. As this is LA, guests use ‘outside voices’ in the morning, clanking plates and cutlery. In California, 7am is practically midday.

But while I’m irked by their pre-dawn energy, in a lonely and isolated world, the new social capital is in bringing people together. “Everyone is open to meeting new people,” Mark says. “If they were a real introvert they’d just stay at an Airbnb.” There are weekly socials and while I’m there our community manager throws a pizza party. One guy shares wine while others bring beers and people jostle to control the music. It feels like pre-gaming before a night out, only with less drinking. I doubt anyone is under thirty.

At the drinks I meet Jessica. Also in her thirties and from Australia, she works for the search engine Duck Duck Go, whose staff are fully remote. She’s keen to tell me one of her favourite stories about Outsite. She had touched down in Nicaragua and was heading to the property there, but before she made it, people in the Outsite group chat “convinced me to go with them to a beach town nearby instead of heading straight to the property.”

Does anyone actually get any work done? Well, during my week-long stay I manage to do a week’s worth of work, but I also hike Runyan Canyan, cruise Mulholland Drive, dine out and go on a naff celebrity home-spotting tour, all with fellow Outsite guests. I find out about cliques, and spot the people who would exhaust me if I were moving in. After drinks we go out on the town and, on the dancefloor, speak about how we are 15 years older than everyone else in the club. At this point, I feel cautiously optimistic that Outsite has given me a community. I can see how this could become a lifestyle.

For the past few months, Mark has been working mornings then spending afternoons with friends he met through Outsite. “When I first came, I found it liberating to see people living differently,” he said. “To see 40-year-old guys going to yoga every day.” Hannah has enjoyed trips to Joshua Tree National Park with Outsite members. “I like the idea that it’s not a twenty-something house share, I can hang out with people who are more established and older,” she says. She doesn’t “feel weird” about house-sharing in her thirties and is tired of the narrative that adults can only cohabit with someone they are sleeping with. “It makes co-living feel very normal.”

The digital nomad stereotype conjures images of someone working their web design job from the beach, beer in one hand, mouse in the other, laptop precariously balanced on a knackered bamboo stool. But what surprises me about Outsite is how members appear to be balancing shades of that life with a far more mundane existence. These digi nomads are grown-up. Rather than living with a bag on their backs, they spend months in one location, and that location is often somewhere functional and ordinary. For people like Hannah, Mark and Jessica, living like an ordinary person in a different city is kind of the point.

Day-to-day life for this type of digital nomad involves going to the gym, eating well and going to bed early. “There’s a rise in people being able to remote work, so there are people who want to do that but in a less knackering and hectic way than being constantly on the move,” says Hannah. “This feels more like I’m actually living here.”

The Outsite experience changes depending on where you go. In Los Angeles, people stay for months, whereas in Europe’s capital of digi nomad working, Lisbon, it’s common for guests to check in for just a few days. Members say flexibility is key. They can book Outsite for exactly the period they want rather than having to commit to a rental in a city they don’t know. But the flip side of that coin is that shorter term guests disturb the feng shui. “It’s a bit exhausting getting to know people when they’re not going to stay,” says Mark. “I’ve been trying to get to know people staying longer term.”

Some members tell me they’d landed at the company because they were fatigued with the obvious alternatives. “Airbnb isn’t a reliable choice these days,” says Hannah. “At Outsite I get a cleaner, my bills paid and a comfy bed. It’s a premium way to travel that isn’t going into a hotel where you don’t talk to anyone.”

On my last night, Hannah, Mark and some others are in the living room in their sweatpants. We talk about relationships, and what it means to be single in our thirties and living on the road. I’ve always romanticised this life, but I realise that, in many ways, it isn’t easy. These people face the same anxieties and loneliness as the rest of us. It’s stressful being this far from home.

But bundled together on the sofa, I feel – for the first time in fifteen years – the sense of community I used to enjoy at university. Just hanging out doing nothing with new people is an experience I’ve craved but have rarely been able to find. Like how the best travel experiences happen when you make the fewest plans, in an age where we’re all seeking community, simply existing together feels incredibly worthwhile.

Go to outsite.co