An Interview with Wayviator’s Founder Curtis Duggan on their New Ebook "How To Be a Digital Nomad"
Interview by Mita Carriman, Founder of Adventurely
The overnight adoption of remote work during the pandemic coupled with digital nomadism skyrocketing from niche to mainstream spiked a demand in the market for better resources on how to be an effective remote worker - especially if you take your work on the road.
Enter Wayviator: the brainchild of Curtis Duggan, a serial Entrepreneur from Canada with a previous exit under his belt, and a passion for exploring the needs and nuances of digital nomadism. Wayviator is a remote work media site which just released its first e-book, “How to Be a Digital Nomad and Work Wherever You Want.”
After getting our hands on a copy, our Founder Mita caught up with Curtis to dive deeper into his personal story, his thoughts around nomadism, the inspiration for Wayviator’s new e-book, and what’s in the pipeline next from the Wayviator team.
Check it out below!
Tell us a bit about your backstory - what originally led you to become a digital nomad?
Curtis: “It happened accidentally and out of necessity. I’ve been an entrepreneur for about ten years now, and during the growth of my last startup (sold in 2020) we ended up needing to be frugal for almost the entire history of the business.
We were always fundraising and looking to get ourselves to the next stage of our growth without spending or wasting too much money.
Although there were a few coworking spaces that our company technically used, a lot of our culture simply became a remote or hybrid culture. We were using Zoom and Slack in 2016 and 2017 before the pandemic made them even more popular.
So out of necessity, I became the CEO of a “hybrid-first” company over several dozen people. We didn’t participate in ‘remote work’ conversations or feel like this was a novel concept. It was just a 2010s startup type of thing.
(At the time) I wouldn’t have considered myself a digital nomad though. I was absolutely not a ‘solopreneur’ or freelancer during those years. I had the very real job of managing a growing international health care company in Canada, the US, and other countries.
After I sold that company, the pandemic years also ‘forced’ me to be a digital nomad. Throughout late 2020 and 2021, Like many people, I perhaps naively thought, continually, that we were always about thirty to sixty days from a return to normalcy. Because of this, I never really committed to an apartment anywhere. The combination of selling my company and the pandemic caused me to eject myself from my Brooklyn apartment in March 2020. I didn’t have an apartment again for two and a half years.
Of course, travel was at a times frowned upon or restricted, but between the waves, during windows of safety, I would go to places I thought that I could work productively. I spent some time at home in Canada with my family. I spent time in Arizona, Montenegro, Croatia, and Mexico.
And in 2020-2021, I really started to understand the power of the remote work movement. During my VC-backed startup days, I didn’t care about “the remote work movement”, I cared about growing my company.”
Of all the places you've visited as a digital nomad, which one was your favorite and least favorite, and why?
Curtis: “I don’t need beach weather all the time, but I tend to enjoy predictable, warm weather that doesn’t force you to adapt your wardrobe too much. I’m from the Pacific Northwest and I don’t like the unpredictability of clouds, sun, or rain showers all year round.
My favorite place so far is not a famous nomad destination -yet. This year I was able to spend time in the Costa Rican beach town of Nosara. It is a surf-and-yoga destination. The beaches are incredible and not overpopulated. The Pura Vida lifestyle of Costa Rica is everywhere. Plentiful work infrastructure and coworking spaces are not quite there yet, but I am sure they will come.”
Nosara Costa Rica | Image credit costarica.org
“I enjoy places that have a village center feeling. This is a very broad definition — it can be anywhere from the Lower East Side of Manhattan to a Montenegro seaside town.
On the extremes of what I don’t like, I tend to dislike isolated rural areas without a slightly populated ‘town center’ within walking distance, and car-and-highway-dominated cities.
I have been in parts of Florida that are probably my least favorite — just endless urban sprawl without a lot of remote working infrastructure. So many buildings and neighborhoods, so few that actually support my needs. I am not talking about Miami, so perhaps that’s different — as I hear that is exploding with startup infrastructure.”
Let's turn to the Wayviator story. In your own words, how would you describe Wayviator and what's your vision with it. What inspired you to create it? I know that's a pretty loaded question, so you can answer it in a way that makes the most sense for you to explain
Curtis: “On Christmas Day in 2021, I was reading some things on my iPad and realized that remote work wasn’t just a short-lived fad of the covid era, but something that would absolutely change society.
During pandemic lockdowns, I had been reading a book series from last century: Will and Ariel Durant’s The Story of Civilization. It is probably 10,000 pages long and spans 11 volumes — starting with Mesopotamian, Egyptian, Indian and Chinese civilizations and tracing history up until The Battle of Waterloo.
Many ‘revolutions’ are covered in this slightly outdated but very well-written series. The invention of agriculture, logic, philosophy, mathematics, monotheistic religions, etc.
I realized that remote work was one of these ‘civilizational shifts’ akin to the major shifts in human history.
Remote work was not just a management fad du jour, but something more like the Industrial Revolution.
As a serial entrepreneur, I decided to start Wayviator.com, because of how much I’ve learned about building a community and audience. Instead of trying to force a product into this space, I decided to play the SEO and growth game and build a brand — rather than a specific product, to learn more about this space.”
I read a copy of Wayviator’s new Ebook, "How to be a Digital Nomad and Work Wherever you Want” and thought you did a great job on it. One of the parts I especially loved reading in it, was your reference to how digital nomadism is mischaracterized in the press. I had a personal chuckle when I read that part, and I'd love to hear you expand on this. You have full license to rant, ha!
Curtis: “Certain grifters, some influencers, and the superficial view of some media in covering the digital nomad movement have created a false impression of remote workers and digital nomads as TikTokers and YouTubers just traveling around and doing photography, selfies and bikini shots in exotic locations.
There was definitely a wave of digital nomads who didn’t have sources of income except convincing other people to become ‘digital nomads’ in a Ponzi-like fashion.
This is not what most people are doing.”
I also really loved the breakdown in the Ebook about how digital nomads should have a long-term strategy. What's been your personal long-term strategy as a digital nomad?
Curtis: “It’s actually hard to say. I don’t think I’ve implemented one yet. I still think about 90-120 days into the future.
If you held me to it though, I think the future looks like long multi-month stays in specific locations, with shorter trips to explore,
Long-term, I’d like to look into real estate in places that I am interested in, although I am pretty comfortable renting long-term too.”
What are you hoping to be the biggest takeaway for readers from Wayviator’s Ebook?
Curtis: “For knowledge workers, there is a new normal in how you can work. The combination of cultural, technological, and regulatory changes make taking a workation easier and more accessible than in 2019 and earlier.
Culturally, companies accept remote work and provide corporate mobility policies more and more. It’s ‘acceptable’ to work remotely more. Technologically, there is more software that is getting better at helping people collaborate remotely. On the regulatory side, countries are giving people more of a legal pathway to stay longer-term in a country.
Though what might not be clear is that in 2019 and earlier, most digital nomads were simply doing what they were doing in a grey area of legality. They were entering on tourist visas and working anyway. The vast majority of people who could work remotely do not want to live their life with a flippant attitude to immigration and tax law. They want to know that what they are doing is legal.
I hope the biggest takeaway readers get is: wow — there is so much more that is possible now, in terms of where I can work remotely.”
Lets talk about digital nomad visas- they can at times be a controversial topic from some thought leaders in the nomad space. I personally never understood why it triggers some folks, but I have to remember I'm not everyone, and folks have different thoughts around this. What's your general feeling about digital nomad visas and their utility, no judgement here!
Curtis: “Here’s my inflammatory take: there is a generation of digital nomads and digital nomad thought leaders who kind of think the world revolves around them and their needs. It doesn’t.
The main complaint seems to be that the current spate of nomad visas is more geared towards longer-term stays and doesn’t cater to people who want to dip in for a short time.
There is possibly even a sense of gatekeeping around who is a ‘true digital nomad’ (zero fixed base, always moving) vs. merely a ‘remote worker’ (someone who relocates and works somewhere else).
I don’t even like this distinction even as I am making it for illustrative purposes.
It reminds me of conversations from twenty years ago — when I was a teenager — I remember the 2000s backpacking movement included a snobbiness around ‘travelers’ vs. ‘tourists’. People who stayed in hostels, lived more cheaply, and went to more ‘off-the-beaten-path’ locations were somehow superior to ‘tourists’ who stayed in hotels and went to tourist spots.
Nations are going to walk before they run. They are going to produce one- and two-year remote worker visas that are straightforward.
Of course nations want to attract stable, medium- to long-term high-income workers and not people coming into a country for 7 days here and there.
Eventually, I am very excited that we will get to some kind of utopian ideal of full global mobility.
But as my time selling into the health care industry taught me, you have to respect and work with the existing system when it comes to nations, governments and things like immigration.”
Where do you think is the most interesting destination for digital nomadism right now, and why?
Split Croatia
Curtis: “I think time-zone adjacent countries that can support traditional industry are very interesting.I think Costa Rica, Tanzania and Croatia are all very attractive.”
What do you think are some new or developing issues for nomadism that you think we'll be hearing more about over the next few years
Curtis: “I think there will be a counter-punch or Counter-Reformation before this nomad rocket is out of orbit and sailing into space. What I mean is — we will start to hit a trough of disillusionment and issues.
Some major companies will simply lose themselves with their workforce around the world. Some CEOs will say ‘enough’ and enact 100% office-only policies. Some companies could go bankrupt just mismanaging a distributed workforce. The news will not portray this societal change as an unexamined great thing.
Remote work leaders are zealots for a new religion. Religions don’t neatly replace the existing society they are disrupting.
So I see a wave of pushback in 2023 as a major issue.
Many remote workers are libertarians aiming to find ways to get to 0% tax rates, legally or otherwise. I see global leaders looking at the rapid erosion of tax bases also pushing back on the idea that people can just fill out a form, move somewhere, and not pay tax anywhere.
But these headwinds are small compared to the blowing tailwinds. I think half a billion people will untether themselves from an office-centric lifestyle by 2030.”
Last but not least, where’s the one place you haven't nomaded yet, that is top on your list to visit next, and why.
Sintra Portugal
Curtis: “I haven’t been to Madeira, Lisbon, and Sintra. They are literally top of the list, in the sense that I am booked to go to Portugal this fall!”
Get the Wayviator Ebook “How to be a Digital Nomad and Work Wherever You want at digitalnomadguide.co
Follow Curtis + Wayviator on socials:
Twitter: @CurtisDuggan
Twitter: @WeAreWayviator
Instagram: @wayviator
About us: Adventurely is where remote work meets adventure! Join one of our month long “Welcome meetups” for digital nomads & remote workers happening in Oaxaca, Mexico City or Playa Del Carmen Mexico 🇲🇽 ✈️💻