Remote-work program roundup: a review of Hacker Paradise, WiFi Tribe, and some comments on the future of social travel.

Nicholas Edwards
Sojourn Group
Published in
6 min readJul 13, 2020

Paid travel groups catering to digital nomads and remote workers have been around for a few years now. Many, like the the first program I joined, have fallen by the wayside, but a few have stuck around. I’m currently a member of two:

I took trips with Hacker Paradise in Mexico, Taiwan, Israel, Italy, and Hungary.

I joined WiFi Tribe chapters in Portugal, Spain, and South Africa.

What’s Included?

Generally, the programs put together a predetermined itinerary of month-long trips to global destinations, and recruit a diverse clientele of travelers to attend each one. Typically these groups are more than 10 people, but less than 50.

Housing is sourced ahead of time, and is usually apartment-style living.

Local workspace memberships are secured in each destination by Hacker Paradise, while WiFi Tribe looks to provide solid connectivity and desk space at home.

Pricing and commitment.

Expect monthly costs starting at $2000 USD.
WiFi Tribe makes efforts to scale this up and down depending on how developed the destination is, and also often offers room-sharing options.
Hacker Paradise offers more flexibility around length of stay, and is generally more willing to work with members who only want to join and pay for a couple weeks.

Both programs offer loyalty discounts for members attending multiple trips, and sometimes offer reduced pricing for members who want to find their own housing.

The good.

HP and Tribe both consistently attract smart, social, adventurous global citizens from all around the world. In every group I’ve joined, the running joke is that we’re all paying for friends, but kind of OK with it. There are always interesting characters, and often potential for new best friends. Because most members are professionals, there’s plenty of networking and knowledge sharing.

Both programs do a great job choosing destinations. While there’s no shortage of culture and excitement to find in the world, there are only so many places that are fun, and can handle can the needs of a bunch of expatriates descending for a month. The good news is that options are expanding and developing every year, and HP and Tribe are always updating their itineraries accordingly.

Inconsistencies.

Housing is the number one consideration when traveling. It’s not easy to find nice places while managing other factors like neighborhood quality (grocery, gym, workspace, safety), proximity to others in the group, noise, etc. Flexibility is key, but a certain level of livability is expected by non-budget travelers. Reliable plumbing, electricity, climate control, access to kitchen and laundry amenities, and some private space. I’ve been on one trip each with HP and Tribe where more than a few members of the trip felt our housing had not been properly vetted, and fell short on too many of these expectations.

Internet and connectivity is usually the number two consideration for remote workers. On two occasions, HP has put me in an apartment without a proper WiFi router. I’ve heard of similar issues on Tribe. HP mitigates these issues by relying on workspaces to be the group’s primary place to get online work done. Tribe doesn’t have this redundancy, which can cause extra stress when things go offline.

The social aspect is another top consideration, because it permeates the whole trip. Both HP and Tribe manually interview and approve all members of the group. Wildcard personalities make it in though. While a little drama is usually harmless, both groups sometimes have issues with bigger rifts forming between members. In my experience, this is usually due to a man making women in the group feel uncomfortable or unsafe. Unfortunately, I’ve heard more than one story about this occurring within the Tribe.

Overall.

Travel booking is a tough industry to grow a business in. The profit margins are thin, expectations are high, and every destination has unique challenges. Hacker Paradise and WiFi Tribe have powered through, built awesome lifestyle communities, and handle a lot of logistical hurdles for me when I want to travel somewhere new.

For every type of problem I’ve encountered on a particular trip, I’ve more often had my expectations met or exceeded on others. On both programs, I’ve had trips where everything went great: we lived comfortably, got work done, and had lots of fun experiencing a new place.

When problems do occur, they often stem from avoidable issues: a breakdown of communication, a lack of transparency with clients, missing knowledge transfer between staff, and stagnant standards. I think these are solvable long-term.

When I’m asked about differences between HP and Tribe, I say HP is a little more activity-focused. Potlucks and lunches, skill-sharing presentations, and officially organized activities are more common. These are usually a lot of fun, but can sometimes cause a little interpersonal burnout.
Tribe, appropriately, is more tribal and cooperative. Members generally need to organize their own activities, housing is more centralized and shared, and most trips expect that everyone can attend for a full month or more.
Both HP and Tribe have brought me some unforgettable experiences, and I recommend giving each a look if you’re considering group travel.

The future.

On top of standard growth and improvement goals, travel-focused organizations now have the COVID-19 pandemic posing new challenges, and forcing a total operational rethink. Remote Year (which I have not done), is a prime example, having caught bad press for their handling of travel lockdowns, while also starting up a new co-living venture.

More established players like Airbnb and Couchsurfing are making drastic changes as well.

I locked down for several months at Outsite Brooklyn, which saw no new bookings during that time.

Clients of these companies, particularly from the United States, are much more restricted in the places they can travel.

We’re all adapting. In the face of these changes, I’m personally hoping for increased cooperation and interoperability between the digital nomad, remote-work, and co-living scenes, and with the broader travel industry. Service providers and consumers are both going to need to share ideas and get creative to keep the lifestyle we love moving forward.

My favorite groups and resources.

Thanks for reading! Here are some links to programs I’ve joined, and tools I use.

Hacker Paradise

WiFi Tribe

Outsite Coliving

Coworkations: an aggregator and mapper of upcoming trips and retreats for digital nomads. Created by a member of HP.

Tripvector: an awesome visual travel-planning platform. Great for meticulous organizers, and veteran nomads who want to put together their own trips. Created by a Tribe member.

Sojourn: If you’re looking to engage with other nomads, come check out our Discord server: https://discord.gg/PSUUFtB
We’ve got a growing cross-section of people from programs like HP and Tribe, chatting about where to travel next!

--

--