Suzy

Raise your hand if the accommodation part of long term travel has caused you any headaches in the past. If both of your hands are in the air, you’re going to delight in this conversation with Joe O’Connor, a full-time traveling dad and the co-founder of Global Family Home Rentals (GFHR). 

We dive into his family's recent 10-month stay on the magical Greek island of Syros to include a local micro-school and the actual $5,000/month spending snapshot to show you exactly how a family of three (with one on the way!) budgets for rent, education, and incredible food abroad.

If you are a homeowner who wants to travel or if you're looking for trusted, vetted, and affordable spaces for your family to land, Joe’s new platform is a total game-changer. I am so excited for the worldschooling community to discover the opportunities with Global Family Home Rentals!

Don’t miss Joe’s brilliant advice on why "decision fatigue" means you should occasionally stop over-planning and just let a great house choose your next destination for you! 

Welcome to the Wander Worldschool Podcast. I'm Suzy, a travel-loving money nerd, mom of two, and our family lives between Spain, Colorado, and soon, Japan. On this show, we discuss the stories, logistics, and finances of traveling families and the many ways to learn and travel along the way. Today we get to know Joe O'Connor. Welcome to the show. Please tell me more about you and your family.

Joe O'Connor

Hi Suzy, thanks so much for having me. A bit about my family: I'm Joe. It's myself and my partner Lindsay. We have a seven-year-old daughter and also a son on the way due in August, which we're really excited about. We are currently in New York where we're from. We just spent eight months living on the island of Syros in Greece, and we've been traveling full-time now for over four years.

Suzy

Well, I'm really excited to talk more about your family travels and also the company that you co-founded, Global Family Home Rentals, specifically with traveling families in mind. It is a great resource for families looking for affordable accommodation around the world. I always like to go back and understand a little more about you and where your love for travel started.

Joe O'Connor

In 2014, I had the opportunity to travel to Sydney, Australia. It was actually through Lindsay's company that she runs, called Team Gleas, which is an international sports agency. For me, this was actually the first time that I ever traveled abroad or lived internationally, and it was an incredible experience. It completely changed my life and really just opened up my mind, my heart, and my eyes to the world in a whole new way. That's where I definitely got bitten by the travel bug. Lindsay actually lived in the UK in her twenties and traveled a ton. So for us, we always said if and when we had a family, when that time came, we would want to continue that travel lifestyle together.

Suzy

And I want to give a shout-out to the Australian listeners because I went there a long time ago. It's a beautiful country, but I also recognize why when people leave Australia to travel, they travel for an extended period of time—because it's quite remote. If you're going to leave, you're not doing it for a short vacation; you're going to up and go and take a year off. I feel like there are Australians all over the world because they also have a strong love of travel. It's a great place. I'd love to get back and spend more time there with the kids too. But you mentioned you've been full-time traveling for the last couple of years. What does that look like?

Joe O'Connor

We've been traveling full-time for over four years now. To back it up a little bit, this was definitely always our family's travel dream. We wanted to get out there and live this lifestyle. At the beginning, though, we had a lot of question marks on how to actually make that happen. This dream definitely did not come to life overnight. I literally remember being at home watching family travel vlogs on the TV and thinking to myself, "Man, how do we go do this? How can we live this lifestyle? How are they doing it? How can we make it happen?" I was really just yearning to get out there as a family and live in that way. I think a lot of our question marks originally were around school—where are we going to go, when, and how can we get our daughter into something?

In the fall of 2021, that was when we actually learned about Boundless Life for the first time. That changed literally everything for us. We very quickly joined; we were really stoked about it. It was in January of 2022 when we actually took our leap to start traveling full-time. We did the whole move out, sold our cars, and put stuff in storage, which is just one way to go out and do it. That just worked best for us at that time. We've been traveling now for the past four plus years, and it's been just absolutely incredible.

Suzy

And you said you were one of the early families with Boundless. Does that mean you were at Sintra?

Joe O'Connor

We were one of the first families to join. We were in that first cohort, and we actually did the first three cohorts in Sintra at that time.

Suzy

So you had a chance to be part of the process of offering feedback on how to improve. I spoke with Elodie recently, and it sounds like they really do rely on the traveling family community to decide where to go next and how to improve cohorts. So I love that there is that family involvement as well. You mentioned you're in New York now and baby number two is on the way. What does travel look like coming up for you?

Joe O'Connor

Yeah, we just landed in New York. With baby number two on the way in August, we want to be around our families for the birth and for some time after. So we could be here for the next year—it could be a little less, it could be a little more. We're just really stoked about this next chapter, though, because we have been traveling full-time, location-independent, and on the go for over four years now. We're excited for this new season of life together. We are also really looking forward to the time when we can get out as a family of four and continue to travel. I think what'll change is we'll probably slow down even more and live even slower to really experience it more together as a family and be more present. This time we're just going to have bottles, diapers, and all the baby things in tow, which is just really fun to think about right now as we look forward to that.

Suzy

Absolutely. The cool thing about having a location-independent life is that you can decide when the best time is to take the next trip; you have some flexibility there. Also, after you have traveled for some time, it is nice to be grounded for a while. Just because you're in one place for an extended period of time doesn't mean that you can't pick up and go at some point in the future. We also know that travel changes with kids. There's a very different mindset to traveling with a baby than a toddler, or even teens. So it's fun to adapt travel to the ages and stages of our kids and our families. You mentioned that you have done a lot of the Boundless cohorts. I'm curious to hear a little more about what education has looked like for your daughter and what her experiences have been with Boundless or any other opportunities that you've been able to incorporate along your travels.

Joe O'Connor

Sure. When we started traveling, we were doing probably six to nine months abroad with Boundless for at least a couple of years. So the Boundless Education program was our daughter's main setup and educational program during that time, and it was great. We then were living in Greece and we decided to enroll her in a local micro-school. It was actually taught and run by one of our really close friends, and that has been her experience for the past eight months or so.

Suzy

So the most recent Syros component of your journey was actually in the micro-school and not at the cohort there. But I've heard the island is very magical. How cool to have a variety of opportunities for schooling and community on a beautiful Greek island, of course. Like you mentioned, when you were just starting out, you were wondering how families travel and how they financially and logistically make this work. What has that been for you all in terms of work, money, resources, and logistics for your travels so far, and then also moving forward?

Joe O'Connor

Not only was our family one of the first to join Boundless as a customer in the early days, but Lindsay and I were actually both really early employees at the company too. We started as customers and then transitioned into our roles. We were both on the sales team, working on the global team remotely. We had the opportunity to work with close to 500 families to really help them take their leap to go live and learn around the world together, which was a really awesome experience. It was actually from our time in those roles and also our family travels that we then decided to co-found a company called GFHR. It stands for Global Family Home Rentals, and that's what we're currently building now together.

Suzy

Very cool. We'll talk more about Global Family Home Rentals shortly. Let's talk about the one-month spending snapshot. This is for a family sitting at home thinking, "Okay, how much might I need to save, or what type of income do I need to have in order to fund travel?" Of course, we know there are people approaching this from all different price points.

Joe O'Connor

I'll give you a snapshot of a recent month when we were just in Greece. I would say our average monthly living expenses were probably around 5,000 USD. This number includes the home we were living in—so our rent and our utilities—our school tuition for our daughter, food, activities both for our daughter and as a family, and then health insurance. It's important to note that we found our home through a really close friend of ours who lives in Syros full-time. To break down what that 5,000 looks like: our home was about 1,500 USD, which again was our rent and utilities, and it's important to note that it was a 10-month lease.

School tuition for our daughter, just one kiddo, was just over 1,000 USD. Our food could be around 2,000 USD—probably a little bit more, to be honest. We love to eat out, especially in Syros, because the food there is just so incredible. Activities for our daughter and for us were anywhere from 300 to 400 euros. Health insurance was a little bit over 100 USD. And again, that total is about 5,000 USD. Also, within that number, it doesn't include things like shopping, haircuts, and stuff like that. We do have a car here in the States, so there is the payment and insurance on that, among other things. Specifically, though, for a family who is going to take a trip to Syros and live the way that we were, that was about the monthly total average.

Suzy

That's so helpful to hear. What you pointed out is that sometimes where we travel, we meet people, we make connections, and we find people who are renting a place out, so it's going to be basically at cost. Or again, a longer-term lease is typically going to be cheaper over the long term as well. Then you also find really cool opportunities for education or travel through people that you meet along the way. Was there any exposure to Greek at the micro-school? I'm curious because Greek does seem very difficult with a whole different alphabet. How did your daughter take to that?

Joe O'Connor

For sure. In the micro-school, the main language was English. There was, however, French and Greek as part of the curriculum, so it was really cool to see her be immersed in that. They recently had their final performance and they did songs in all three of those languages and actually more, which was just really cool to see all the kiddos up there.

Suzy

That is so cool. I also was thinking, is Syros an island that is very seasonal? Like, you're going to have really high rental prices over the summer months, but then the rest of the year it's not as touristy. I'm just curious how that works for Syros or Greece in general.

Joe O'Connor

Definitely. Peak season, which we're starting to get closer to in July and August, prices are much, much higher, as they are anywhere in Europe at that time for sure. Because we had a close friend and we had lived there for a while, we found this awesome spot that we were able to lock in at that price for the 10-month lease, which was awesome for our family. We have stayed in apartments long-term there that were much more than that. It was actually just a couple of doors down from where we lived for over a year when we first came to Syros with Boundless. So it was cool to be back in what I'll say is our old neighborhood in a lot of ways.

Suzy

That's so great to be able to come back to some places that we really love as we travel. I'm really curious to hear more about Global Family Home Rentals because housing, like we just talked about, is a big part of travel, right? Where are we going to stay? How are we going to find our accommodations? Tell me a little bit more about Global Family Home Rentals, how it started, and what is part of the program.

Joe O'Connor

You nailed it; home is such a huge part of the experience for families. For GFHR, which stands for Global Family Home Rentals, where the whole concept came from was when Lindsay and I were at Boundless. We had the opportunity, which was so cool, to meet and connect with thousands of families from around the world. A question that we heard all the time was, "We want to travel long-term, we want to live this lifestyle as a family, but what do we do with our home while we're away?" Families who are homeowners didn't want to double-pay the rent or mortgage back home and then for their accommodation wherever they were going to travel. A huge thing, too, was that they didn't want to just rent to any random stranger off of other platforms. One more thing: if a family is slow traveling or traveling long-term, looking at 30 plus days or more, they don't want to be flipping their home all the time and going through the management and the turnover.

On the other side of that, there are also a lot of families who were looking for homes that were trusted, affordable, and family-friendly that they could stay in while they were on the go. While there are tons of home platforms out there where families can go rent a place, we really felt that there wasn't one specifically on the market that tailored to the unique needs of a slow-traveling family. So in 2025, Lindsay and I co-founded GFHR to try and help solve this problem, and we've been building it ever since.

Suzy

And you bring up some amazing points around housing. Yes, I have talked about how to rent your house out when you travel. I also talk about those situations that have not been ideal because I like to keep it real here; there are challenges and hard parts about it. I'm not saying that you're not going to have that if you have a traveling family in there, but like I've experienced with home exchanges, when it is a specific platform and there's some vetting there—you said it's invite-only—you're going to have a very different level of trust between the people staying in your house than you would with just any old rental property system. Tell me a little more about how it works.

Joe O'Connor

Yeah, to first touch on the point you just made, there's a fear for many families. A lot of the homes that they have serve as their primary residence; this is their family home. To turn around and just give the keys to anybody, there is a fear that they're going to trash their homes or something's going to happen and they're not going to let them know. We've recognized and learned about a lot of other fears and problems that families have in this world, which has pushed us even more to want to get GFHR going and to help families in this space.

To share a little bit more about what it is, GFHR is an invite-only home rental collection and community specifically designed for traveling families. Homes on the platform are listed at cost to cover families' expenses, not to make a profit. We have background checks and ID verification built-in. Trust is the highest value that we have. For so many families who joined our waitlist early on and have since joined, trust is the number one reason why they're coming to GFHR and want to be a part of it. We're in the mid-term rental space, so 30 plus days or more. There are no communication restrictions or transaction fees.

Something that we've really put a lot of time and energy into are the home listings on our platform, which are all very intentionally designed with families in mind. A couple of features on it that I think are worth sharing for families listening who have a home or want to stay in trusted homes: on our listings, we have built out areas that really give host families the opportunity to share about their home and showcase the surrounding areas that they live in. We've found in talking to families that they love to be able to do that. A few things that you'll see on our listings are, one, what are the nearby local experiences? Is there a national park around this home? Are there beaches, a children's museum, or community essentials? What is a host family's favorite grocery store that has all the great stuff, or their favorite coffee shops and co-working spaces?

We even have a section for learning and childcare. When a family is choosing to come to this area and potentially live in this home, what are the day camps? What are a family's favorite babysitters, homeschool groups, or international schools? Obviously, health, medical, and safety are really important too when you're choosing a place to travel. So on there, you're going to have the name of the local hospital, pediatrician, and pharmacy. Again, this is all set up from the host side. What we've heard from guest families is that they absolutely love that because it takes so much of the guesswork out of having to plan travel in that way.

What's great about it is that before they even think about connecting with this family or requesting to book—you also can't instant-book on our platform; we really want families to build relationships, get to know each other, and then decide if it's a great fit—they have all that information right at their fingertips. They can actually make the most informed decision for their family and what's going to be best for them as they're planning their travel and setting things up.

Suzy

I've been looking at longer-term stays in Japan and I'm like, "Sell me not just on your home, but sell me on the location. What can I do? What is within walking distance?" There's not as much information out there as I would like. Also, maybe you're familiar with Furnished Finder, and that's where we list sometimes in the US, but it's designed for healthcare workers. It tells you where the closest hospitals are, but that's not necessarily everything a traveling family wants to know. When you're staying somewhere long-term, you're not just spending two nights in the city where you'll figure out what to do when you get there. You want to know what there is to do within this location because you're committing to a month or more. It's not just the home; it's the location and what's around it. You mentioned that families who are homeowners can participate. Fill me in on what other individuals could be potential participants?

Joe O'Connor

How the process works is that families are either invited by a current member or they apply for an invitation through our website, meet with Lindsay, and then they need to pass the background check and ID verification to then be able to pay their annual membership and join. We have no restrictions on needing to own a home or list on the platform. Families can actually choose to join as a host, a guest, or both—whatever works best for them. The reason we do that is because once you pay your membership, you get access to everything. That's going to give you access to the home collection, the trusted community of families, and all of our partnerships and resources that we've set up. Some of them are going to include landlord insurance, guest protection, and lease templates. Regardless of whether you are a host, a guest, or both, you get access to all of that.

Why we ask that upfront is because we want the data in-house to know why families are joining and what their intention is. We actually learned really early on that close to 80% of families, probably more, are choosing to join as both a host and a guest. They're bringing that supply and demand for us in what is a two-sided marketplace. They have the intention and the desire to want to use it to rent out their home and also go stay in awesome, family-friendly homes around the world as well.

Something that we've learned too, which we just think is really cool in these early days, is that if you look at a lot of the platforms that are on the market right now, a lot of times people say, "I know in my mind that in June I'm going to Ireland and I need to go find a place to stay," which is what brings them to that platform. For GFHR, what we're learning from families is that they're looking at it actually in the opposite way, especially in the long-term or slow-traveling family space. They're saying, "You know what, we have the ability to travel in June and we have flexibility through August as well. Let's go check out GFHR, see what homes are in the collection and available at that time, and then choose based on the house and the destination we're going to go to." It's been cool to just have those conversations early on and see that.

As we get close to launching this month, we're really, really excited to see how that unfolds. We just had a booking recently where our friends who are from the States, living in Greece, are a GFHR member and their home is on the platform. They just booked a Finnish family's home in Spain. How cool to see all of that coming together—four different countries, two global families. It was really awesome to see.

Suzy

Once you're a member, like you said, you're there, right? Sometimes your housing situation changes. Maybe this is a primary home, but you sell it because you want to travel full-time for a while. Or you have a rental somewhere, like we have a long-term rental in Spain. I'm also thinking that sometimes if you're traveling and you're in an RV, you might not necessarily at that point of your travels need or want to stay somewhere else, but your home is available. I love that you've created this opportunity for people to be a part of it in whatever way they're able to, while still keeping this community. So many families are flexible; they just want to go have a really cool cultural experience in a new place. Sometimes it really is the right house that makes it a really cool experience, or the right location near really cool things that you didn't even realize you would have found unless you had this cool house opportunity. I love keeping an open mind to serendipity when you travel, especially long-term. Sometimes that decision fatigue comes into play and you're like, "I don't know, this house is available, let's go."

Joe O'Connor

Yeah. We really want to make family travel more accessible, more affordable, and more community-driven—that is our mission and our intention with GFHR. Family travel over the past four years has completely changed our lives. It was once just a dream at one point, and to now live it, I get goosebumps when I say it and think about it still, even though we've been doing it for so long now. It changed everything for us in so many different ways, from the places we've lived, the lifelong friends we've met, and the incredible memories we've made.

With GFHR, we want to be able to provide those same opportunities for other families as well. We really see GFHR as a resource. On the homeowner side, it's a way to cover those expenses while you're away, and in some cases, help fund travel. On the other side, while families are on the go, they get access to our collection of trusted, affordable, family-friendly homes. We really feel like this can help more families travel with more peace of mind. It already can be hectic; there's lots going on and so many different variables that you need to decide on. Where are you going to live? What are you doing for schooling? We have to book this flight; we have to be here at a certain time. If through GFHR we can bring more accessibility and peace of mind to the family travel space, we feel good about that and we're really stoked about it too.

Suzy

And I'm sure my kids are not alone that when they go to a new house that has toys, even if they're similar to the toys that we have at our house, it's like Christmas.

Joe O'Connor

All of that information—kids' toys, books, puzzles, car seats—if a host family is setting up their listing and they have those different things accessible, they have the ability to check it and it'll show up on the listing as well. Again, for a family to be informed and have all the info they need to make a really awesome decision, those types of details are included on GFHR because we're so family-focused on the company as a whole, but definitely with our listings.

Suzy

You mentioned that you have many founding families already and you have homes all over the world in different countries. Share with me a little more about where those homes are located, just so if a family is thinking about joining, they get some insights on what is possible for them.

Joe O'Connor

For sure. We currently have 50 founding families who've joined pre-launch, and we have close to 40 homes across nine countries. We're super stoked to actually be launching, which is so exciting having been building it now for probably 15 or so months. With the countries that we currently have, we are in Canada, across the US, Italy, Greece, Portugal, Finland, Spain, and Thailand. It's been really cool to see it go global so quickly early on, especially pre-launch.

You mentioned Furnished Finder earlier. I would say if you look at the home rental companies out there on a spectrum, on one side you could have an Airbnb or a VRBO, and on the other side, you could have HomeExchange, for example, or people like us. Some of the big differences between those are that on the Airbnb and VRBO side, there's a financial exchange between host and guest, whereas on the other side, it's more of a home swap or home exchange setup. For GFHR, I would say that we're in the middle of that spectrum, similar to where a Furnished Finder would sit, especially because we're both in the mid-term rental space of 30 plus days.

For GFHR, we don't handle any of the payment processing on our platform. That's because we don't have any transaction fees and it's an annual membership. What that opens up for families is the flexibility to pay and receive money in a way that works best for them, and that's included right on the listings too. I think it's important to share all that because there are so many options out there where we fall on that spectrum. Also, because we don't handle the money, there's the opportunity for a home swap—reciprocal or non-reciprocal—on the platform too, because what we're really providing is the connection of families and the environment that they're connecting in, with the resources that back it up.

Once they connect, you can stay on our platform and continue to build a relationship and message, or you can go to WhatsApp, FaceTime, or do a video tour. Again, trust is just so important to us. We want families connecting as soon as possible, building that relationship, and then together finalizing all the details of the stay so it works best for both parties.

Suzy

And then it gives them the chance to say, "This is my home, this is how I want it to work." As long as they're clear in their listing with what that is, then other people can make informed choices if that works for them or not. It's a way to give homeowners or traveling families more of the authority with where they go with this. Anytime you're on Furnished Finder and you have someone reach out, you're going to be running a background check, professional and personal references, and so on. This is a little different in that you're already part of a community, so you've already moved past some of those first steps. Yeah, this is really fascinating to see how you've basically found the gaps and then found something that works for families. I like that.

Joe O'Connor

Yeah, it fit us, and it fit a demographic of who we are and how we've lived. Even more importantly, we've connected with so many families around the world, both professionally and personally, where we saw gaps, like you said, or problems on the table that we decided to take the leap and try to solve. For us, it's a very focused and niche market that we're looking to serve, and it's one that we know really well because we've been living it too as a family.

Suzy

That means you've really identified some of the problems, and you have a group of people that you can network with to help figure out these solutions and what people need and want. Part of keeping it real, though, is understanding that there are challenges—either the challenges of the business side of things, or even the challenges that might come with long-term travel. I also always like to talk about the wins, whether that's the family travel wins or the business wins.

Joe O'Connor

I can totally speak to both. Starting with the family side, I think one of the biggest challenges is that we've been doing at least six to nine months abroad for the past four years at this point, so just missing our people back home—friends and family—and being able to spend that time together. I'm grateful for technology in that way because we can hop on a FaceTime or WhatsApp and connect. Personally, I've also found that I've struggled with the transient nature of the lifestyle, especially when building relationships with people who are amazing, whom I love, where we're aligning on values and having so much fun together. At the same time as that process is unfolding, I know that eventually we're going to have to say bye, or see you later, see you soon. I definitely have struggled with that over time.

I'd say on the business side, less related to travel and more just about building an early-stage startup, there are certainly the ups and downs that come with it. I think the process of navigating that is learning how to ride that wave and not get too attached to what stage we're at—whether we are in a peak or in a valley—and just continuing to be really intentional each day and take a step forward. Ultimately, though, it's been awesome building GFHR together. Lindsay and I have absolutely loved it.

On the win side, celebrating just the fact that we have been traveling for four years, and that was what our dream was. To actually take the leap and go live it, and now experience it in all the ways that we have, has just been so amazing. Ultimately, when I look back to four, five, or six years ago, we decided not to settle and to go for the lifestyle that we wanted to live, one that felt authentic to us and aligned with our values. When I think back to that time and to where we are right now, back then I could have never even imagined how it could unfold in this way and what it could look like.

I say that really just to encourage any families listening who haven't taken that leap yet, but have been dreaming about it—whether it's travel or not—to go for the things that you truly want in life, give them everything you have, enjoy it, and know that the only way to know how it's going to unfold is by taking that initial leap, which is the hardest step in anything. But by doing so, it really opens up the opportunity to just be absolutely blown away, which I think is really, really cool.

Suzy

That's really well said. I'm going to link everything in the show notes. But let's wrap up with the lightning round to get to know you a little bit better. You can only ever visit or live in three countries. What are they?

Joe O'Connor

I'm going to go with Syros, Greece, because we absolutely love it; it's an incredible place. Number two for me is going to be Australia because I have that connection there. We haven't been back as a family altogether, so I'm really excited about that when the time comes to go. And I'm going to say the US, just being in upstate or Western New York around our family and friends.

Suzy

What is one item that you cannot travel without?

Joe O'Connor

I bought a backpack a couple of years ago in Italy that literally is an extension of my body. I use it for everything: a suitcase, a work bag, and a beach bag when we go together as a family with friends. I even will put a bunch of weight in it and go outside for a long hike or a ruck. It has so many different uses, and I just absolutely love it. I can't imagine not having that bag or one like it.

Suzy

That's a traveler's dream, to have the perfect backpack. I have like three, but they are not perfect all in one, and I'm like, "I just need one that would do it all." What is the first thing you do when you arrive somewhere new?

Joe O'Connor

For me, I love to get outside. If there is grass around, I love to get my feet in it. Then I just take a few minutes to unpack. I'm a pretty simple guy, so again, a lot of my stuff that I'm bringing just fits in my backpack. I like to get it out to be able to then use the backpack for other things. Those are the things that I'll do right when we get somewhere new.

Suzy

And if people want to learn more about you and about the website, where can they get ahold of you?

Joe O'Connor

Yeah, definitely. For families who want to learn more about GFHR, you can head right to our website, which is GFHR.co. If while you're there, you feel like you're interested in joining, you want to learn more, and you think it could be a great fit and add value to your family, just submit the application on the site. Then Lindsay and I are going to reach out to set up a call to connect with your family and get to know you more. If anybody wants to get in touch with me personally, you can find me on LinkedIn. Just search my name, Joe O'Connor, and we can connect there.

Suzy

Thank you so much for sharing more about your travels as a family. Best of luck in your new adventure coming up soon with baby number two—that's going to be super exciting. I'll make sure to link all this in the show notes so people can check it out. Thank you so much.

Joe O'Connor

Thanks so much for having me, Suzy. This was awesome.