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Digital Nomad 2020 Online Conference – An Interview with Matt Dykstra

kokou adzo



Matthew Dykstra Digital Nomad 2020

In this COVID-19 world, it has become increasingly important to find alternate sources of income. Digital Nomad 2020 is a conference series dedicated to helping its members build a solid financial future with a location independent lifestyle.

Recently I sat down with Matthew Dykstra, the founder of Digital Nomad 2020, and ask a few questions about the conference, COVID, and more…

What is Digital Nomad 2020?

Matt Dykstra: At its core, Digital Nomad 2020 is a series of conferences designed to help anyone who is (or wants to be) a Remote Worker, Digital Nomad, or Freelancer build a better life for themselves.  

We have some of the world’s best speakers – experts in building online businesses, location independent businesses, taxes, travel, legal issues, and more!  

All dedicated to helping our members build an income that does not depend on living in any one particular place. 

Who is the conference series for?

Matt Dykstra: The title of the conference series is Digital Nomad 2020, but really it is for anyone living anywhere with an internet connection. You do not have to be a Digital Nomad living on some distant exotic island – You can attend the conference in your yoga pants, eating potato chips on your living room couch… We won’t tell.

What is important is the desire to be in control of your own life. 

What is a Digital Nomad? 

Matt Dykstra: If you ask 100 Digital Nomads to define the term, you will probably get 101 definitions. But for me, I can sum it up with a brief story… 

In the early 2000’s I was on an airplane sitting next to my wife. While working on my laptop, a thought struck me… I turned to my wife & told her that one day I wanted to quick my job at Microsoft & start a business.  

A company where we could travel to & work from anywhere we wanted – a tropical beach, the Swiss Alps, a South American city… anywhere in the world – the only requirement being an internet connection.

At the time, I had never heard the term Digital Nomad, nor did my wife take me that seriously. But to me, that kind of location independence is at the heart of being a Digital Nomad.  

You don’t have to travel all the time. But for a true Digital Nomad, work will never be the reason you don’t. 

How did you become a Digital Nomad? 

Matt Dykstra: Remember the conversation I mentioned on the plane? 

Now fast forward almost two decades…  

I did leave Microsoft, and now I am the founder & CEO of my own award-winning Digital Marketing Agency (TreDigital).

I never forgot my idea, but I also didn’t move forward with it. 

When TreDigital was launched, it was based in Bellevue, Washington (just outside Seattle).  

My wife & I did travel but not as Nomads.  

Over the summers, especially, we would take our kids abroad so they could see the world. But at the end of the summer, it was always right back to Bellevue.

Then a few years ago, that suddenly changed. Late one August, I asked the question, “Why do we have to go back now?”

The truth was, the business was running just fine with us working remotely. The children were adapting to new cultures & having life-changing experiences. You simply cannot reproduce living in one city.

So we made where we were our home base & officially became Digital Nomads.

Why did you create Digital Nomad 2020? 

Matt Dykstra: Like many Digital Nomads & Remote Workers, the decision to take this journey was made on the fly. None of the basics (renting our home, banking, taxes, or even setting up education for our kids) was considered before we left the U.S., and now it all had to be figured out from abroad. 

So I researched the web, talked to consultants & attended conferences – trying to get everything set up properly. However, no matter who I spoke to, where I looked, I always found myself needing to ask more questions. And every time I attended a conference, I either immediately forgot what I learned or found myself waiting a year to learn the next steps. It was a very frustrating & expensive experience.

Digital Nomad 2020 was conceived because of that frustration. 

I wanted to create a conference for anyone who wanted to live a location independent life. But unlike most conferences, I wanted one that provides information in a structure that allows you to implement what you learn before coming back for more. One that encourages members to ask questions, anytime – not just during the conference.  

A conference focused on helping its members build their success.

What is one way that Digital Nomad 2020 is unique?

Matt Dykstra: Digital Nomad 2020 holds three (or more) separate weekend conferences a year. Each conference created so that it can stand on its own (in case this is your first time in attendance) but also builds on the knowledge given previously. So you have that opportunity to implement what you learn & then return in a couple of months to learn the next steps.

All of our speakers have committed to this structure & the goal of Digital Nomad 2020 – to help our audience succeed. Thus a majority of our speakers return for multiple conferences throughout the year & many have committed for multiple years! 

Was Digital Nomad 2020 moved to the web because of COVID-19?  

Matt Dykstra: The Coronavirus Pandemic has forced many conferences online, but Digital Nomad 2020 is not one of them. It was initially conceived as an online conference for a reason.

Our goal is to help our members succeed. Asking members to pay for a trip to someplace they weren’t already planning to go seems not only unnecessary but in fact, financially irresponsible. And therefore not in the interest of our members.

Does that mean Digital Nomad 2020 will never hold a traditional conference? 

Matt Dykstra: Never say Never… But not for now.  

If enough of our members requested it, I would consider it. But for now, we’ll just keep finding ways to improve our current model.

How has the pandemic affected the conference?

Matt Dykstra: Perhaps the largest impact to the conference has been the number of Remote Workers (who work from home) attending the conference.  

Many of them have told us how they were traditional 9 to 5 workers that due to COVID19 were suddenly forced to work remotely. Working where they never thought they would like to, only to find the freedom being location independent has allowed them to spend more time with family, explore their area & consider what working remotely permanently would be like. 

Why did you choose to stay abroad during the first wave of COVID-19?

Matt Dykstra: The Seattle area has been my home for longer than anywhere else I can remember. Most of my family and friends live there, and eventually, I will return there as well.  

However, only half a year ago, Seattle was America’s first epicenter for the pandemic. And that made returning to the United States a risky option. 

I would have had to take my family to a European epicenter. Fly them to one of two other European epicenters (Frankfurt or London) and then through New York or Washington D.C. (also risky) before finally arriving in Seattle. Every step would mean putting my children at greater risk.

So while the safety of my children made a choice to stay in Eastern Europe was not easy, I believe it was the right one.  

What’s it like planning a conference this large? 

Matt Dykstra: Planning a conference, virtual or otherwise, is a full-time job. 

The sheer number of individual parts is amazing. And there is always something that needs to be managed almost 24/7. 

Even then, there will always be problems that you need to adapt to instantly so you can find solutions.

That said, it’s not all hard work & no fun. I have talked with so many amazing people who, at one point or another, have decided to go against conventional wisdom and strike out on their own. People investing in themselves and changing their lives as well as those who built a future of their own making. They amaze and inspire me.  

When is the next conference in the series? Is it too late to join? 

Matt Dykstra: This December 5th & 6th will mark Digital Nomad 2020’s December conference. Tickets are selling fast, but many are still available.  

If you have not attended a previous conference, I recommend checking the conference out at

Part of the beauty of the conference is that you truly can join at any stage. Each conference, we not only add new speakers but also bring back previous speakers to build on their previous presentations. So there is knowledge to be gained from new members and existing.

We have noted that the goal of the conference is to help its members succeed. Does this mean there is a path you want your audience to follow?

Matt Dykstra: For Digital Nomad 2020, success means 

  • Showing our members how to sort any loose ends in the States (Taxes, Renting, etc.);
  • Assisting those who are new to Remote Work or being a Digital Nomad find the niche that is right for them.
  • Helping members make that transition from a successful one-person operation to location in depended business with at least one digital assistant.

Will there be a Digital Nomad 2021?

Matt Dykstra: Yes. This is an on-going conference series designed to continue to run for many more years to come.

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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