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Meet Our #LandingLife Contest Winners: Madison and Ivan

By Landing | Jan 12, 2022
#LandingLife contest winners Madison and Ivan on the beach.

Back in December, we announced the winners of our #LandingLife contest, offering a once-in-a-life opportunity for winners to live with us for one year, rent-free. Newlywed digital nomads Madison and Ivan delighted the judges with their tales from the road, their desire for a dishwasher and stable Wi-Fi, and their plans to eat everything—literally, everything—throughout their travels. 

We’ll be hearing a lot more from Madison and Ivan on Landing Life throughout the year, but first, we wanted to give these two a chance to introduce themselves and share some of their travel plans. 

Without further ado, meet Madison and Ivan! 

Q: How did you two start your lifestyle as digital nomads?

Ivan: Last year, I was working as an engineer at the NASA Jet Propulsion Lab in Pasadena, California. I had been there since I graduated college and got to work on some fantastic missions, like the Mars Perseverance Rover and the Europa Clipper. I played a small part in helping these cool rovers and satellites with their interstellar travel, and I loved the job. But in the back of our minds, we always had the travel bug, especially once we met each other. 

I always knew I could do my job from anywhere, and COVID really helped prove that. So in March 2021, I started my own business doing consultancy and product development in the same realm as my work at NASA. That’s given me the ability to move around and adopt this more nomadic lifestyle.

Madison: At the time, I was working in reality television. I was traveling a lot for work for the different shows I was working on. I loved being able to travel all over the world with my job, but I was working twelve-and-a-half-hour days and only got one day off per location to explore. Plus, I was alone! I realized that while I loved traveling and working in entertainment, I wanted to do it with Ivan. I started my own YouTube channel to see how I could combine my love of travel and entertainment while working remotely. 

Ivan: We started doing some weeklong trips at first to try the lifestyle out and make sure it was something we wanted to do. Then, in the later half of 2021, we jumped all in! We spent a quarter of the year in Mexico in a couple different destinations. Even just this last week, we moved from Colorado to Texas to Georgia!

Q: What parts of your digital nomad lifestyle do you enjoy?

Madison: Because we’re staying in places for a longer period of time, we like the opportunity to see the tourist attractions there, then dig a lot deeper into local life and all the special things the city has to offer. Whenever we watch travel videos on YouTube, it seems like people go from place to place really quickly. What we want to show in our videos is what it’s really like to be a digital nomad and experience all the little things about a new destination and the differences between that and what you’re used to. For example, in Mexico, you don’t get refrigerated milk—you buy it in a box, and it’s delicious! 

Ivan: For me, one of my favorite parts of being a digital nomad is the food. I love eating food and I love talking about food. Not to get too philosophical, but what we’ve found just naturally is that there are more similarities between people than differences, and through food and experiences, we can bridge a lot of those gaps.

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Q: How did you learn about the #LandingLife contest? 

Madison: Ivan and I were living in Mexico City and trying to figure out where we were going to travel after we went home for the holidays. We liked being in Mexico during COVID because it was close by, so we could always just go home if something happened. Ivan was looking at tourist visas for other countries, but we kept circling back to how many incredible places there are in our own country that we hadn’t yet explored. 

I’m very lucky that my dad signed us up for the family plan on Apple News because I learned about the #LandingLife contest from a notification from Condé Nast saying, “Want to live somewhere for free with Landing? Enter this contest!” Looking at the details, we found out we would get to experience living in four cities in the U.S. for a year! It was bizarre. It was fate! When we applied, I felt like we were dreaming big, but somehow, that dream has come true. When I found out we won, I couldn’t believe it was happening. 

Q: Where is your first Landing going to be?

Madison: We’re heading to Washington, D.C. on Jan. 14. We’ve visited the city three times, but only for short visits. Usually Ivan is there for work, and I just explore by myself. It’s always been a place we wanted to dig deeper into. We’ve done a lot of the touristy things there, but we’re really excited to dive further into what the city has to offer. The food scene there is amazing, and we’re especially excited to eat at all of Chef José Andrés’ restaurants. 

Ivan: We’ve been to a lot of museums and the main sights like the White House and the Washington Monument a number of times, but there are so many smaller things we’re excited to check out that we haven’t had a chance to. It won’t be a crash course of the top 10 list. 

Madison: We’re still going to go to all the Smithsonians, though! Washington, D.C. is awesome because a lot of places are free to visit, which increases our food budget! I’m also excited for the hikes and waterfalls in the area, and I want to visit Shenandoah National Park and the Crystal Grottoes Cavern. 

Q: Where else are you planning on traveling this year?

Ivan: We want to keep things fluid because we know Landing adds new cities all the time, but we definitely want to go to New York City during the holiday season. We want to be there for the Macy’s Thanksgiving Day Parade, the lighting of the Rockefeller Christmas Tree, and watching the ball drop on New Year’s Eve. So we might plan some of our future cities around cool events happening in the area. 

We’re also hoping to move to places we want to get more familiar with to see if we could live there permanently, such as Boston, Seattle, and Nashville. We love visiting Nashville, but would the music scene get old after being there longer than a couple of days? I don’t think it would, but we want to test the waters before finding our forever home.  

Q: What have you done so far to prepare for your stay with Landing? 

Madison: When we started out as digital nomads, we started selling things and minimizing our belongings to make it easier to travel around. However, now I feel like our preparation is kind of the opposite of what Landing members usually do, since we’re going to be in a nicer, more luxurious place. When we were traveling in Mexico, Ivan made his coffee with this tiny coffee maker that takes forever to make one cup, but now that we’re traveling in the U.S. and bringing our car, we’re going to take our big espresso machine along with us. We’re expanding, which is really the opposite of what the other contest winners are probably doing! 

Q: What part of living with Landing makes you the most excited? 

Madison: I’m excited to be able to see the National Mall and the monuments from the rooftop of our new building. And, we’ll have a gym, a dishwasher, and an in-unit washer and dryer. There’s also a bunch of workspace areas in the building where we’ll be able to edit videos and do engineering work. 

Ivan: I’m more of a stationary worker—I set up my battle station, it’s exactly the way I want it, and that’s where I work. Madison’s more of a mobile worker. She likes to mix it up and sit outside, on the couch, at the table, or in her bed. So she’ll have some more options to sprawl at our Landing with the workspaces. 

Madison: When we discovered Landing, it was literally exactly what we’d been looking for. When we applied for the contest, we were staying in places with bad Wi-Fi, no dishwashers, and other little things. It was okay, but it could have been more liveable. 

Ivan: With Landing it seems like you’re picking among a nice baseline of options, all of which are more than good enough for us. You’re nitpicking at that point, but you’re going to end up happy no matter what. Whereas with other places we’ve stayed, you have to study the place, ask questions, message the host, and ask them what their internet speed is. With Landing, it just feels like we’re going to be very comfortable, and everything else is a bonus. 

Stay tuned for more adventures with Madison and Ivan

Madison and Ivan will continue to share their stories on Landing Life over the course of the year, highlighting their favorite spots to visit in their new cities and making recommendations for other people kick-starting their digital nomad life. Check back soon!


Ted may be the world's slowest typist and struggle to hold a pen, but he has mastered how to pursue a more flexible lifestyle throughout his airborne adventures around the U.S. Whether you're looking for more information before migrating to a new city or want to find an easier way to rent a nest—erm, apartment—Ted will always be here to share his best advice for where to live and how to thrive.