Imagine a week in which you could work effectively for hours at a time, then simply pop out of your office and go for a hike, surf, ski or snowboard, acting as if you're on vacation...on a Tuesday.

That's the world envisioned by recently launched company Outsite, with the name a portmanteau of the words outdoor and offsite. Their emphasis is on developing the "location independent lifestyle," and helping people achieve more work/life balance.

Founder Manu Guisset decided to build the company after being on a surfing vacation and experiencing dissatisfaction with his wifi connection at inexpensive, but beach adjacent motels.

First, he beta tested demand for the concept by posting on craigslist and searching on Airbnb. Deciding that it was worth a try, he set out to find a property with the criteria:

1. Less than 5 minutes to a decent surf spot
2. An upscale villa and large comfortable rooms
3. Ability to convert a section of the property into a big work space

He found it in Santa Cruz, California, less than an hour from Silicon Valley, and an hour and a half from San Francisco. It was an obvious choice for the first Outsite property, with a potential oversupply of startup employees with flexible schedules, who might relish the idea of an escape for a day, a weekend, a week, or even a month.

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The next property Outsite launched was also an obvious choice--Lake Tahoe, taking advantage of the winter sports, when visitors are less keen to jump in the freezing Santa Cruz Winter waters.


Outsite is currently raising a seed round, aiming is to launch ten properties in the next 18 months while running events to promote awareness, such as the digital nomad meetup and pitch on the beach. But there's more to why their business might be a big success.

An unexpected and delightful aspect

What is surprising about the business (which could essentially just feel like a set of large Airbnb properties, with a targeted user base) is their approach to community. I spent a weekend at the Santa Cruz house last autumn, and was blown away by how amicable the other housemates were. Not only were we working side by side in the office part of the house (and seemingly getting our work done), but also we were sharing meals, going out, and surfing together.


Only in a house that's intentionally filled with people with complimentary personality types would that be possible. It reminded me a bit of the 2002 film L'auberge Espagnole, and made me nostalgic for my sorority house at university. There was a community manager at the Outsite house who facilitated intros, contextualized what people did, and organized gatherings and outings so that we would get to know each other. It was like having a Residential Adviser at a dorm. And it's not so dissimilar from community managers at co-working spaces (where some excel more than others admittedly, often determined by whether the space has a theme or not for their workers and members).

Outsite's approach is not a new idea. Other companies and "projects" like Work for Anywhere (which emerged from The Thousand Network*, previously known as Sandbox, who are a community of 1,000 like-minded individuals around the world) are setting up structured work away programs and locations, places where entrepreneurs and folks in the "1099 economy" who have flexible schedules can escape and relax, but not opt out. These aren't people making small salaries either; they're folks who are often making six figures, giving them an increased amount of flexibility. As compared to Work From Anywhere or We Roam, a year long work away program, Outsite's play, is more heavily grounded both in real estate AND in community development.

Recently, Outsite launched an application-based membership program, novel to the work away model. It's probably derived from other membership organizations like Soho House, which aren't explicitly offices or modern country clubs, but a blend. Founder Guisset says, "Outsite has naturally cultivated a dynamic sense of belonging, but this is our way of proactively fostering an active community of like-minded professionals and giving them the resources to live a more balanced life."

Why is this happening now?

There appears to be a new craving for a different approach to work/live and even "vacation." New co-living communities like Common Living and Roam also have membership models, but are grounded more in full-time versus temporary lodging. With mottos like "flexible, community driven housing on a month to month basis," and "live in interesting places with interesting people, for a week or for a lifetime," they're touching on this growing trend in non-static lifestyle approaches. And WeWork, the co-working company valued at $16 billion, just launched WeLive, with their first property in NYC.


Airbnb just last week launched a new application, focused on highlighting hosts' favorite places in their cities, helping their users travel like locals, with the motto "Don't Just Go There, Live There." The new global lifestyle, whether working, co-living, or traveling, is about authenticity, and finding the right types of people, places, and experiences, not just the top or best according to the masses.

Three major systemic factors have led to these types of business emerging: a growth in flexible work, coupled with the increasing cost of living in cities, and a new found comfort in sharing living spaces with strangers thanks to the likes of Airbnb. Forrester recently projected that telecommuting would rise to a whopping 43% of the workforce in the U.S. in 2016, and this is with only a 56% broadband penetration. Furthermore, the internet has flattened not just the world of communications, but the world of relationships, allowing people to stay in touch though they may live across a country or the world from each other. Friendships aside, relative strangers can now better see their common connections, whether people or interests. Though, it's interesting to note, community managers and people and products whose role are meant to physically connect appropriate people, businesses, and ultimately facilitate experiences, are still paramount.

Michael Youngblood , co-founder of Be Unsettled, a new company in beta incubating at TED's NYC residency, elaborates on why the time to build a company in co-living is now:

"It's only been about 60 or so years the corporation has become principal organizer for how people work in our society. While I think many elements of the corporate structure will remain in place for decades to come, technology has enabled some segments of the working population to work from anywhere, yet other institutions such as housing, leasing & contracting, and medium-term living have not changed as quickly as the workplace. Furthermore, 20 and 30-year olds entered the workforce during once in-a-lifetime recession that has impacted how we live, how much we are willing to invest in assets, and what we value. Our generation is renting more and at a higher cost than ever before, but the cornerstone of renting--a short-term contact that provides flexibility over buying--is a broken remnant of the 20th century economy that was designed to encourage homeownership. The cost of renting is hitting a pain point in many places across the world, and many people are beginning to look for other options."

Finally, it would be a mistake to forget the trend in getting rid of our stuff and in cutting down our space. There's a reason a Japanese author, Marie Kondo, has become a household name. Her book, The Life-Changing Magic of Tidying Up, has sold millions upon millions of copies. The Atlantic recently penned a piece on obsessive compulsive de-cluttering. And minimalistic living via the tiny house movement, with popular blogs like Tiny House Swoon, is permeating culture. Living in shared or compact spaces around the globe not only allows us to de-clutter and travel, but arguably also clears space for living a more purpose-driven, aligned life.


A better inside outside balance

Speaking of alignment, as we now know (scientifically and not just intuitively), "Being in nature, or even viewing scenes of nature, reduces anger, fear, and stress and increases pleasant feelings. It also increases our ability to pay attention." And maybe most importantly, it increases our sense of community and connection.

Conferences like Summit Series**, that bring high-achieving individuals (artists, entrepreneurs, nonprofit leaders, and more) together in places like the Caribbean, a mountain they bought in Utah, Tulum, and more, discovered the connection between being outdoors and fostering community years ago. This author wrote a piece for The Economist back in 2011 on how conferences could learn a lesson from how Summit focused on allowing attendees to meet each other and build relationships, rather than just focusing on programmed content. They aligned their attendees while also programming thoughtful content in interesting places, and have built a business and community off the back of that model.

Now, other new organizations have emerged to tap into the idea that being outside (without moving there full-time), and having less access to your technology, could further personal and professional growth and your sense of community. In Camp Grounded and Camp Reset, your technology is literally stripped from you in order to facilitate a digital detox. Passage is a 21-day application based program in Costa Rica where attendees worked earlier this year on shifting technology habits and behavior, with their next event lasting for 10 days in Guatemala this July.

Existing retreats and transformative conferences like Renaissance Weekend have always been held in vacation spots like Napa, Santa Monica, and upstate New York. But rather than following the traditional session model, new companies with events and community as their core are focused more on unconferences, replacing structure with teaching each other skills, often oriented around spirituality, health and wellness, and improving upon daily habits i.e. life hacking. Outsite is also hosting company retreats, and has hosted for the likes of LinkedIn, Waze, and KIND already. It's a revitalizing approach to gathering, and also timely, as people are more overwhelmed by their technology than quite possibly ever before. It's partially why Burning Man has swelled from a few hundred people in 1986 to selling out to over 70,000 in 2016.

All of these companies, products, conferences, experiences, and communities fit the mold of blending people + outdoors experiences with limited technology in order to deepen relationships, foster collaboration, and with what I would argue has innovation as the ultimate goal. It's not just how "millennials get away together" but more likely the "next generation of networking," where play is just as important as the takeaways.

What's next?

In a world where our technology doesn't seem to be abating (VR, AR, Bots...), I believe we'll continue to see a rise in businesses and experiences blending the outdoors and "getting away" with also still getting work done. We'll continue to see the housing market disrupted, as people connect over shared values and a general dismay with decades old regulation. As Professor, author, and previous Secretary of Labor Robert B. Reich notes, "tribalism is on the rise again."


The most successful businesses will also be grounded in community and relationship development. In the same way that we've seen a rise in longform content and storytelling, we're craving deeper relationships, in a society where it feels like we have more breadth than ever before. The winners will blend both innovative spaces and places with powerful communities. We'll see businesses emerge from people meeting at these spaces and events, subsequently collaborating and innovating.

And though I don't think we'll see everyone going to surf and ski while working away, and I don't think that Tim Ferris' 4 hour work week become the norm, I do think that the global nomad community will start to more deeply shape policy and culture in the next decade and for generations to come.

*disclaimer: this author is an active member of The Thousand Network.

**disclaimer: this author attends Summit Series events and gatherings