Interview with Matthew Laskowski and Kim Shepperd about Their Remote Travel Program!

remote travel program

Modern Nomad: A Remote Travel Program in the US

Kim and Matthew found a new life when they started working from home. However, after the first months of excitement, they realized that working from anywhere isn’t always as fun as it looks like. Moving to a new place without knowing anyone can be challenging, and the risk of isolation is hunting all of us after the pandemic. 

Looking for solutions to connect with like-minded people, they couldn’t find good alternatives for people working remotely like them – seeking a different type of flexibility than freelancers or entrepreneurs. Here´s when Modern Nomad came to life. They launched and provide rotational housing for remote workers, offering a concrete solution for those willing to change their routine and try new adventures while growing professionally. 

The pilot program of Modern Nomad will start very soon. Meantime, here is an interview with Mathew and Kim to learn more about their experience as remote workers and their new remote work travel program! 

In Conversation with Matthew and Kim:

1. To start, could you introduce yourself and how you got passionate about the nomad lifestyle?

Raised in Hong Kong for most of his life, Matthew has always loved travel. So much that it took him to attend university in the US. After his time in the states, he eventually landed in the UK. He still loves to traverse the globe with friends and family. 

Currently, he calls London home although he has spent the majority of the last few years living a rather nomadic lifestyle working and living from a boat in the Mediterranean to the fjords of Norway. 

On the other hand, Kim was born in the Philippines and raised in Texas, Kim’s thirst for travel started early from the beaches of Boracay all the way to the Gulf Coast. She’s traveled throughout Central Europe, the Caribbean, and all across the US. 

She currently calls the mountains of Colorado home and you can find her gallivanting around with her camera in tow. 

2. Let’s talk about The Modern Nomad. How does that story begin?

Our story begins with a long exhaustive search… that ended up at a dead end.

Matthew was working remotely, due to Covid, in amazing locations – poolside at a villa in the South of France, in the countryside near the South West Coast of England, in Barcelona, Madrid, Croatia, Slovenia, New York, Chicago, LA, Hawaii, and more!

On the other hand, Kim had been working remotely from home, which she had been doing for over a decade. 

They were independently searching the market for travel-work options and found that they were all catered towards freelancers and entrepreneurs, but not more standard full-time employees like ourselves. That’s when we conducted an exhaustive search and found that there was nothing in the market that suited our preferences. After serendipitously meeting each other, we decided that we had no choice but to start a business that provides housing for standard 9-5 remote workers in the US. 

3. What is rotational co-living, and why do you think it’s a better solution for remote workers, compared to other travel programs for entrepreneurs or freelancers?

The term may perfectly encapsulate the act yet, but we think it gets the message across. 

When I say ‘Digital Nomad’, you likely think of an individual who has no fixed location, moves frequently, and works from a laptop. True nomads, on the other hand, are groups of individuals that move from the same location and to the same location. These are quite different arrangements and we wanted Digital Nomads to act like how Nomads actually work… Large groups of digital nomads travel from the same location and to the same location.

That’s why current digital nomad options are catered towards entrepreneurs or freelancers – The minority of people who are most adventurous and willing to live in Thailand with potentially spotty Wifi. Our target market is the majority of individuals working remotely, but from home, who would be willing to be a Nomad of sorts. And our target market is the remote worker in the US remote worker, who is likely just working from home. 

For example, a curated cohort (ex. 20 people) of young Full-Time professionals from many different companies (ex. Google) from different cities (ex. LA, Chicago, NYC) do a rotational (ex. 4 rotations of 3-months) co-living program (ex. 12-months total) in different locations (ex. Austin, Nashville, Denver, New Orleans). 

There are a few main problems with how Digital Nomads currently do things:
  • Working Poor Time Zones: Most Nomad programs are in Europe or Asia and for the American worker, it’s not ideal to start your day at 2am
  • Constant Moving Stress: A lot of ‘nomad’ housing programs are monthly and moving at that frequency is stressful and exhausting
  • Weak Social Bonds: Current options on the market offer unlimited flexibility, but this comes with a cost. As soon as you make friends, they end up moving somewhere else after a few weeks and you have to make new friends again

That’s why when we started, we had a few criteria:

  • Acceptable USA Timezones: We restricted our search to the Americas, as Americans don’t want to work European or Asian hours
  • Stress Free Moving: We wanted to move at a leisurely and comfortable pace and not at an overwhelming pace
  • Strong Social Bonds: We were looking to develop and create lasting friendships over a number of months and not something more aking to ‘speed-dating’… Creating a bunch of superficial friendships

4. Which type of programs and activities do you offer, and for how long do you usually travel?

Our Programs are the same as a standard lease, 12 months. We like to think of ourselves as ‘The Most Exciting Lease You’ll Ever Sign’ rather than a ‘1 month getaway’.

We are starting with a standard 12-month option, across 4 locations, 3 months each, in the US. To start, we have many locations across the US. Imagine: Summer in Denver, Colorado, Fall in Nashville, Tennessee, Winter in Sedona, Arizona, and Spring in Miami, Florida 

In the future, we will have options for an expedited, 6 location, 2 months each option, and an ‘international’ option, which will move to locations across both North and South America. Additionally, we will have a ‘Mystery Program’, where you will not know the exact locations and cities!

5. And what about your locations?

Additional locations include – Denver (Colorado), Naples (Florida), Burlington (Vermont), Nashville (Tennessee), Fayetteville (Arkansas), New Orleans (Louisiana), Charleston (South Carolina), Bozeman (Montana) Boise (Idaho), Madison (Wisconsin), and so on

International locations will include – Buenos Aires (Argentina), Rio de Janeiro (Brazil), Mexico City (Mexico), Montreal (Canada)

6. Could you describe what’s unique about your co-living to create a vibrant and dynamic community for remote workers?

The fact that you’re with your Program group/cohort for one whole year (12 months). A lot of digital nomad and co-living situations offer great flexibility, which is a double-edged sword. Often, you’ll make friends and before you know it, you’ve gone your separate ways.. The reality is that after only 1-month, friendships are a bit surface level and superficial. A year with someone allows you to build a strong social bond.

7. Why do you think it’s important to offer opportunities to travel and network?

When someone is a remote worker, they will realistically stay where they are currently living. And although they may say that they can travel and work from anywhere, they will usually not move to a ‘random’ city where they do not know anyone and will only go where family or close friends are… Someone working remotely in New York is not going to move to Austin for 2 months to explore, where they have no friends. Traveling with a group means you can bring that network of people with you. 

8. What challenges did you face as remote workers traveling the world, and what would you recommend to someone starting this new lifestyle?

In my mind, there are 2 types of remote workers – Work from home or digital nomads.

The digital nomad lifestyle is very fun at times, but it’s also volatile and can be quite lonely due to the transient nature of it. On the other hand, working from home can be boring and lonely, especially if you don’t have enough social interactions. The human mammal is probably the most social creature in earth’s history. Both our co founders faced this challenge and we’d recommend ensuring that you have strong social bonds and not many that are deep… (and it so happens that this is what our company solves for).

9. How do you think travel programs like yours can help people achieve a better work-life balance while growing professionally?

We like a line in a poem by William Cowper – “Variety is the very spice of life, That gives it all its flavor.” A program like ours gives someone 4 entirely new locations, cities, cultures, and people to explore over 12-months, all the while with a large group of +20 friends with them. This is a lot of extra ‘life’ to balance against ‘work’. 

Additionally, a program like this allows one to network and grow professionally. In the office, organic interactions happened, but when people started working from home remotely, that stopped. We’re giving individuals the chance at +20 like-minded individuals to network with and grow professionally together, as you travel across the US. 

10. When will your travel program officially start? And what are the most exciting activities you have planned?

We’re starting with a pilot of 20 intrepid explorers to see how this thing works! Right now about 8 of those spots are filled and are looking to launch our pilot as soon as we fill the remaining spots! After that, we have ~30 Programs ready to launch, with properties lined up.

Planned activities drive the price up for a lot of the other digital nomad options on the market and is what makes them so expensive. In order to keep our costs lower than our competition, we’ve elected not to be anyone’s ‘parents’ and plan activities for them. In the first weeks, we will have meet-and-greets, bar nights, and evening activities. But after that, we expect the group to know each other and from there, we’ll let things organically evolve.

11. If you could broadcast one message to all digital nomads, what would that message be? (Twitter-length).

Find your Tribe and gear up for the adventure of your life! @ 

12. Who inspires you? Can you recommend a book or podcast for those thinking about changing their lifestyle?

Matthew – Norman Borlaug, the man who saved a billion lives / (book) The Beginning of Infinity, “All fiction that does not violate the laws of physics is fact.” – David Deutsch, which means that so long as something does not violate the laws of physics, the only thing precluding something becoming real is the effort we are willing to put into it, or human knowledge, which he also argues is unbounded

Kim – My Aunt is my primary inspiration when it comes to living the life that one wants. She traveled across the globe as a lone female in the late 60’s, early 70’s and eventually established roots on the Gulf Coast where lived and passed on at the age of 84. I was taught by her to go after what you want, work hard and plan accordingly. I also would recommend absorbing the works of photographer/explorer Jimmy Chin. 

13. Any future project lineup after summer?

We have quite a few assortments of programs to launch and a bunch of properties across the USA lined up! We’re just excited to launch and move forward with our Pilot Program! 

13. Anything else you’d like to share?

Please apply to our pilot program!


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