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Hello and welcome. This is Gabriel Custodiet of Watchman Privacy, Privacy practitioner, consultant, author and frontline fighter in the push for privacy. I know why you're here. Like the rest of us here in the resistance, you're trying to escape the technocratic apparatuses that you see enveloping you and crushing your freedoms. That's why I created all of this, all without sponsors. I hope you enjoy this show. But then when you're ready to take the next steps to secure your privacy and your future, Visit my website, escapethetechnocracy.com to start the real journey. Your support alone does not determines the future of the show. See you there. Welcome, everyone. I'm very pleased to be joined today by Kayleigh from Expats Everywhere. This is a YouTube channel where Kayleigh and Josh talk about internationalization. Specific focus on Portugal a lot of times. So that means today we're going to be talking about internationalization, enhancing your freedom by moving abroad, being an expat, Some of the trials and tribulations that come as a result of that. And I know Kaylee and Josh, I've visited them in Portugal recently. I've consulted with them. They're really good authorities on the topic. And it's a pleasure to be able to talk to Kayleigh today. So, Kayleigh, welcome to the show. How are you doing?
B
Thanks for having me. I'm doing really well. How are you?
A
I'm doing great. Let's do the bio question here and maybe at the same time, as you're talking about yourself a little bit, explain why you chose to become an expat.
B
Sure. I'll just make it quick because I get asked this a lot and it could be a long story, but essentially, in 2009, Josh and I decided to move abroad. I had traveled a lot as a kid with my dad's job. He was in baseball, internationally, domestically. My parents love to travel, so we did a lot as a child. So it was no surprise when I graduated college that I was like, I'm going to go experience the world. And then Josh is a small town boy, and it was a surprise that he wanted to get out of the small town because generally everyone stays there. So when he and I met, he was talking about moving abroad. I was in my senior year of college. He had already graduated, and he was talking about moving abroad. And I said, I'll wait for me to graduate and I'll go with you just because I wanted to do it, but I didn't want to do it by myself. So he was like, okay, like, let's just, let's try this out. So we, our first place that we went to was in Spain. And we said, okay, let's give it a couple of years, let's see how it goes. And we enjoyed it so much, being able to travel around Europe, that we thought, let's experience Asia. Let's try something even different, a place we've never been. So then what we did is we created this five Year Plan. And the Five Year Plan was to be two years in Europe, two years in Asia, and then we wanted to finish our fifth year in Brazil and go to the World cup and experience that, and then move back to the US and quote, unquote, get real jobs is what everyone was saying. Get it out of your system while you're young, do this, and then you'll come back, you know, you'll get married, you'll get real jobs, you'll have the white picket fence and so on. But after the first year or so in Spain, we're like, I, this is something that we could do. We found a way to, to do it and to move around and to base ourselves in different parts of the world. So the Five Year Plan got, you know, extended pretty quickly. We knew it was going to be longer than five years. We just had to figure out where do we want to go, what do we want to do, how are we making money to make sure that we can do it and then go from there. So we, we started in Spain and then we went to South Korea, Saudi Arabia, Singapore, and then after 10 years in Asia, we're like, let's get back to the European lifestyle. And now we're in Portugal.
A
Now why is Portugal your landing place then?
B
Well, we lived in Spain. We actually really enjoyed visiting Portugal at that time again, 2009 to 2011, like, a lot of Americans didn't even know where it was. They didn't know it was in Europe. And it was almost at that point. It was definitely like the hidden gem. It was a lot quieter than it is now. I mean, it's on everyone's radar now, but a lot of people didn't know about it, but we would visit because it was. It's different culturally than Spain, but there are still a lot of similarities as far as family and lifestyle and so on. So, so we would visit and we found that it was cheaper than Spain, which was nice. The people were nicer. Overall, we lived in Madrid, and Madrid can be a bit harsh as far as how nice people are. And it's gotten a little better but when we lived there, it was like people didn't speak English. They were quite harsh and capital mentality. And we found that it was a bit of a break coming to Portugal. And specifically we really loved Porto. So we love that Porto was a city. It had the river, it has the ocean, it has. And so when we visited from Spain, we just were like, we're going to end up living here at some point. We just didn't know how that would happen and what visa we would be on and so on. So we just knew that we would end up in Portugal at some point. And then when we were in Singapore, we found the route to make it to Portugal.
A
I was recently in Portugal. I second that. It's a nice place to be for sure. People are speaking English. I think that's a result of smaller country, niche language. You are kind of forced to speak English and they have no problem with it. Also very friendly people. Why do you think though, Kaylee? Why is Portugal generally so popular these days for expats?
B
I think that it's because it's a newer option for people. Americans, like I was saying before, didn't even know that it was part of Europe 10 years ago. Now as people are looking for different locations, maybe to move outside of the U.S. whether that's to retire or just they can work remotely and they want to experience something different. They want something different for their kids. The, the focus was for the longest time on Central America and some of those areas now have gotten way more expensive. So the goals are different for people. There's. So they're more expensive, maybe they're not as safe, they're not as exciting because you end up in an expat bubble. So people are looking for other options. And honestly I think that also for the longest time people wanted to move to Europe because there's this romantic idea of how Europe is. But there wasn't a good visa and a good option to do so if you. And then parts of it are expensive and then you think about taxes and so on. So for the longest time Portugal just wasn't on people's radar and then now it is. There's a lot of information out there about it. But we as Americans can get a couple very easy visas. Affordability for a lot of things. I mean right now housing is pretty high, but affordability as far as the day to day lifestyle that you can have here is really nice. You can have beaches if you want, you can have some of the mountains if you want. So for a small country, it does offer A lot as far as landscape. So I just think that people know about it now. And so it's. It's become popular a place to be.
A
Yeah, I was talking to people while I was there. They said it's definitely had a boom in the last 10 years or so. Very desirable for people who are looking to stay there beyond just the temporary amount of time they have by default. Let's say as an American, was it 90 days to be there? But people who are trying to get visas, what is the. Just the overview of some of the popular visa types that people are pursuing when they go to Portugal in a more serious capacity.
B
The top two that I work with that are definitely by far the most popular are called the D7 and the D8. And so both of them are living off of individual revenue. But the D7 is through passive capacity, which would be IRAs, certain types of investments, Social Security, social media, so retirement mostly. But it can also be rental property as well. And then the D8 is more like the remote worker digital nomad visa. So you have to be making money, like whether your company allows you to live outside the US you own your own company and you pay yourself. So it's active income, so it has to be a source that's outside of Portugal. These are definitely the top two ones where you're making your money outside of Portugal in a different way and then you're living here. So it does come with a. The residency path. But then of course, if you look, if you're looking to study, there's a student visa, there's entrepreneurship, there's a golden visa. So there are actually a variety of options, but definitely the D7 and the DA are the most popular.
A
Right. And there is some things potentially changing on the, on the horizon regarding the, the process of becoming a resident of Portugal. But for now, and generally, what is the. Like what, like what are. What are some of the mechanics of acquiring these visas?
B
Yes. If we hone on the D7, the D8, since they are the popular ones, the way that it works is you do have to apply from your home country or where you've been a tax resident. So let's say you're American, but you've been living in Mexico for three years or so, and you've been paying taxes and so on, then you could use their consular services there. But anyone who's just in the US what you do is you have to get all of the requirements that are listed either for the D7 or D8, and they're fairly similar. There's just a few minor details that are different. And you apply through either a third party organization called BFS that helps countries provide process visas. You either apply that way or you're the nearest consulate. It depends on your jurisdiction. So it actually depends on which state you're in, which one you're allowed to do. So you would apply for that and then you would come to Portugal. You'd finalize your residency at an in person appointment with ima, who is the agency that processes the visas, and so on the immigration. And after that then you are a temporary residency. And currently it's good for two years. And this has actually changed about three times since Josh and I have been here. But. But in the past couple of years it's been the same. So currently the temporary residency is good for two years and then you renew and then the next one it's good for three years and then after five years you can choose to renew the temporary residency again, which is fine. Or you could do permanent residency, which is good for five years. So then after you complete the 10 years, and this is the new law that's happened after the 10 years now you can apply for citizenship. It used to be that after five years you could apply for citizenship, but that is just recently changed. So then after 10 years you can apply for citizenship in Portugal, if you've been living here.
A
So basically this is. Even with the changes, would you say that this is the smoothest, the lowest barrier to entry to getting a European residency?
B
There are some other countries that are actually really good as well. You have to factor in your, how you're making your money. That's one of the big things, if it is passive or active. Because, for example, France can be really good for retirees, especially when you're thinking about taxes as well. But then there are other European countries that are good for digital nomads or remote work. So it kind of depends on your one, your lifestyle and what you actually want in a country where you want to live with the climate and everything, but then also how you're making your money and which visa actually applies. But for Europe, it is actually, I mean, it is one of the best, as long as you make sure you get your ducks in a row for the right visa.
A
And what would you say is the most difficult part of the process of getting this temporary residency which you just discussed? Because everything you described makes sense. But for example, the VFS appointment you talked about, there's a huge backlog people, it's difficult for them to get appointments. What are some of the on the ground practical hurdles of this process right
B
now, that one is actually the biggest hurdle because they're in such high demand that they only unlock a certain amount in the different either VFS offices or consulates. And so they're only unlocking so many. Especially in the US it is a little different if you're in a different country because they unlock a lot more. So for example, I have a client who, she's American, that she had been working in Japan for a couple of years. And so because she had been in Japan, she could use her consular services there. And when I worked with her on getting that appointment, we pulled up the calendar. Literally, she could have gotten an appointment for this visa the next day. That is impossible to do in the US because of such high demand. So right now I would say the biggest hurdle is getting that appointment. And now once you have that appointment, you obviously need to make sure that you have all the requirements. Another big one that I think is a pain point for a lot of people is for the D7, D8. Currently you have to have an accommodation lease. So you have to have proof of where you're going to land when you get here, which I kind of understand why they did that. I think partially they did it because they want to make sure you had a place to be once you got here. But the problem is some people don't know exactly where they want to be or they want to feel like they're not locked into a place and they want to explore a country before they actually go somewhere. But that is a little harder. I mean, there are some workarounds, but it's a little harder. But the problem is, is they're looking for a one year lease. Now let's say you're going to rent a place, they're looking for a one year lease, but it's taking them like two to three months to process the visas. So you go to this VFS appointment, you have to have the lease there. It doesn't necessarily have to be active on that day, but it's really hard to negotiate with the landlord that is going to be active like three months later. And some of this as well is because there's a been a bit of a long term housing crisis in Portugal. So there's just not enough available. And so the landlords don't have to negotiate this. They, they're, they're holding on the keys really because people are lined up trying to get into these apartments. So it'd be really hard to negotiate like, hey, I need this Lease, but I don't need to start for three months, you know, so that you're not burning those months. So it's, you know, that's a little unlikely at this point. It's getting a little better, which is good as we're seeing that the more real estate is coming on the market for the long term housing. But that's a pain point as well for people because not only do you have to have this lease, but are you able to come over here on a scouting trip and look at the place yourself or are you going to have to do this site unseen and just hope that. I don't know if you have a realtor, do you have a company like that are going in and they're actually seeing, you know, if this place is legit and if there's making sure there's no mold on the walls or there's not a dog barking next door or whatever. So I think that the housing component scared a lot of people too. And that's, that's a tough one.
A
Definitely recommend people who are trying to diversify their jurisdiction, move abroad, whatever the case may be. You do want to consider having a second residency, maybe even eventually a second citizenship. Portugal's is a pretty good option. There's obviously some things to work out, which is why I would recommend the people listening go check out expats everywhere, the YouTube channel, and then consider just cutting to the chase and consulting with, with Kayleigh or Josh. Definitely recommend that. Now, Kayleigh, what is the latest on. It used to be that after five years, as you were saying, you could apply to be, to get the passport for Portugal. What is the latest update on that?
B
Yes, so that has recently changed. It's been talked about for about a year. So last year, around June, this conversation came up and everyone thought it was going to happen right away. And in true Portuguese fashion, it did not. It took a long time for it actually to be processed because it was passed through Parliament and then the president sent it to the Constitutional Court who said some of these things in this document are unconstitutional. So then they kick it back to parliament and so they had to go through a lot of like legal back and forth. But finally around May, the beginning of May of this year, it was passed through Parliament and signed off by the President. And actually since then there's a new president as well. So what has happened is, is they've just made it harder. There's a lot of things that they've made a little harder as far as immigration goes. But one of big things that has surprised a lot of people is that it used to be that after five years here, then you could apply for citizenship. And now they changed it to either seven if you're from an EU country or from a country that was colonized by Portugal. So we're talking about like Cape Verd, Angola, Brazil and so on. So those have to wait for seven years and then they can apply for citizenship. But for the rest of us, so for Americans, you have to wait for 10 years to be able to get your citizenship through naturalization.
A
One reason why people might want to switch jurisdictions or be more of the perpetual traveler type situation is to change their tax situation. Now we don't want to get into the weeds of this. Obviously not tax advice, but what is the big picture understanding of maybe the benefits of being in Portugal for taxation reasons or maybe some of the downsides? Could you just give a high level overview of that?
B
Yeah, sure. So this is why a lot of people went the golden visa route, because with the D7, the D8, they are residency visas. So there is a stay requirement. And essentially the same requirement for those two is you can't be outside of Portugal longer than six months consecutively or eight months total within your visa period. And that's the two years renew and then three years. So within those two sections. So but you are living here and then you do have to file taxes. You have to have proof that you're doing that. So always you should take a look and make sure that you're, that it's going to be tax beneficial for you if you're going to move here. But a lot of people, that's why they did the golden visa, because there's a far less stay requirement. It's mainly seven days in a year that you'd have to be here. So you don't have to be a tax resident, you don't have to file here. So for those who are high income earners, it made a lot of sense because they, they used to have something called nhr, which is a ta. It was a tax regime that was really favorable and it, it locked in a set rate for certain taxes. And actually NHR was not just something that was for foreigners, it was for Portuguese as well, like port. If you lived outside of Portugal as a Portuguese person for longer than five years and then you came back and you had never done nhr, then you could implement this. And it's, it's locked in for 10 years. So you're locked into just a set percentage for 10 years and it can't go any higher than that. Now they did aware that it was to bring people back in because a lot of the young people were leaving. So it was to bring people back in and it ended up working. And so they did away with that. And they do have an NHR 2.0, but it's mainly for highly skilled. It's a lot more specific and so it's a lot harder to get in into that. So I think that as far as taxes go, the thing is, is in like a lot of European countries, taxes can be really high. And so sometimes you see that Portugal is 48% and it's possible to get to 48%, but it is on a progressive scale. So it's not just like you see 48%. You think my whole income is going to be taxed at 48%. It's not necessarily that. Um, so it is the progressive scale and it depends on which category you land in and what that looks like. And then also the US and, and Portugal have a double taxation treaty. So there's certain things that you shouldn't be paying double tax on. But if you, let's say your percentage is 20% in the US and you land into the 30 percentile over here, then you're probably going to end up paying the rest of that, that 10% over in Portugal. So it's really important that you structure the right way before you move and before you come a re become a resident here. That's really, really important. So speaking with a tax professional about your situation is important.
A
Portugal has had a reputation as being crypto friendly. What exactly does that mean?
B
I think it's because they don't have many, if like maybe very few tax laws on cryptocurrency. So for the longest time it was zero, it wasn't being taxed. And obviously there's stipulations on how long you have to hold it and so on. But I think it's been deemed tax friendly because of the, I don't want to say lack of regulation, but they haven't implemented too many laws to where it's over tax and it's over regulated. So there's a lot of freedom there now. It was, I think a little better a couple years ago when it seemed like there was not much at all. And I think that now they're, they're doing a few more things. But I still think it's tax or it's not tax friendly. Excuse me, it's crypto friendly because of that.
A
Right. Of course, I have in the back of My mind listeners to my show will know that one of the co founders of Samurai Wallet, the two gentlemen who were arrested quite unjustly and are in prison now for running a bitcoin wallet, one of them was living in Lisbon and basically when the US government told the federal government in Portugal to arrest him, they did so with no hesitation and they put him into a medieval prison. So I always have that in the back of my mind in terms of crypto friendly, but I think considering the US's reach, a lot of countries would have done something similar. What do you find, Kaylee? Are some of the common characteristics of successful expats? Getting a little bit into the kind of the psychology of leaving your country.
B
I think that you need to be open to the change. You can't expect, whatever your lifestyle was, wherever you were living, to just pick it up and move and you're going to be happy and it's going to be exactly the same. That's super unrealistic. It's not going to happen and you're going to then be unhappy. So going with the flow of things, understanding that you've moved to a different country and it's going to be different. Looking at things in an optimistic outlook is really important as well. Not harping on the little things that bug you. I mean, of course, you know, every once in a while you can have the rant, it could bug you, but you can't let it fester and continue to grow or else you're going to become very discontent with the place that you're in. So to successfully move, I think that you just have to be excited for the adventure and be like, I'm going to take it as it comes. And then Also there's this YouTube channel. I haven't watched it in a while, but I used to watch it and it was like, I think it's called yes theory where it's like you just say yes. So like this guy goes around and says, hey, like if you say yes, like go pack your bags and we're on a plan and I'll, you know, like we'll take you to wherever, but you don't know where it is. And so I mean, obviously that's a little scary. And people are like, no, I have work or I've got to go to this or whatever. And there's always an excuse to be like, no, I can't or I don't want to or you know, you feel like you're not mentally prepared to do something like that. And I'm not saying it has to be like super extreme in that sense. But when you get to a new place, maybe you didn't go out often or you wouldn't try something like X, Y, Z. But saying yes and opening up to that and the new culture that you're in is just going to give you new experiences and then I think make the whole lifestyle that you're trying to create just a little more open and interesting and maybe you'll find your comfort level a little faster.
A
Yes, I would add that one of my recommendations is to make friends with locals as soon as you can and integrate them into your life because they will be a good translation between you and the local area and they'll certainly open new horizons to you that just being in your home expat bubble or the general expat bubble will not allow you to have.
B
Yeah, definitely. I was just going to add to that. I think the best locals to find are the ones who've been expats themselves because they understand what it's like to be an expat. So maybe they, they were living in a different country for a little bit and they're back in their home country. But because they experience that, they, they can connect with you in a way that, you know you've done the same thing before, so they understand what you're going through. Yet they're still local because they're from that country. So they can also help with the connections of like, the language and the culture and so on that are really beneficial. So I. Those for us have been some of our best Portuguese friends are the ones who were expats themselves because they understand what it's like.
A
Right? And sometimes if you don't have a big network, you'll have to go out of your way to find such people. Meetup.com, just kind of saying yes to a lot of things and, and finding your way from there. Now, Kaylee, you've traveled all around Portugal. Obviously, when a lot of people come to Portugal, they'll end up in Lisbon, which is the main city, big chunk of the population. What are some alternatives to Lisbon that people should also consider?
B
Well, obviously Porto, we would say we, we like Porto better than Lisbon. So I'm going to say that. But it is the second largest city. So if you're looking for something a little smaller, it kind of depends on lifestyle, of course, but a lot of people tend to go to Braga as well. Braga is smaller, you know, smaller than Porto. It's not small, but smaller than Porto. But it's Also flat and very walkable. So those who are older tend to like Braga a little more. Then you have Coimbra. If you're really into history, that's where the big university is. It's got a little river that runs through there. Through there, it's a. It is hillier, but it's very beautiful in their old town. So Coimbra, because you're not going too small just yet. So those are up kind of in the north and the center. If you're looking for the coast, you can find some small places along the Silver coast, which is between Lisbon and Porto. Now, some of those areas are a little seasonal, so they get pretty sleepy and quiet in the winter and then boom, a bit in the summer because it's by the ocean. And then weather wise, those will be a little cooler than, let's say, Algarve, which is the southern part. Now, Algarve, I feel like, is sometimes it feels like you're not in Portugal, and it depends on where you are. But there's a lot more golf courses, there's a lot more resorts there. For the longest time, the British have been retiring there. So almost, I guess you could think of it as like the Florida of. Of Portugal, even though it's a, you know, it's a different, you know, country of people that are moving there. You know, the Brits to the south. But it's almost like, yeah, the New Yorkers to. To Florida, but, you know, so some places don't feel super Portuguese there. Like, you might walk in. Like, for example, like one time we were in and we. And we went to a pub and Josh started speaking Portuguese to the guy to order, and the guy was like, english, mate, I don't speak Portuguese. Like, okay, so sometimes, you know, you get that. But there are other places that still feel a lot more Portuguese. It's just kind of a weird mix in Algarve. But some people find it a little more comforting because it feels a little more familiar. Especially if you're like, super concerned about the language. Then English is widely spoken there, even though English is spoken in a lot of the bigger areas, because the Portuguese have a very high English language proficiency. But that's where you would go for, like, the warmest weather and the most English. Now, I would say, say you don't want to go. You know, there are smaller places that are nice, but if you've never been an expat before, then I wouldn't start in one of these places because sometimes it can feel a little isolating and lonely. If there's not many expats there, if you don't really know how the country works. And so it can be very stressful. So sometimes an easier entryway is one of the bigger cities, just to get comfortable and then figure out what you're going to do. You just don't want to be too isolated. And I've seen people be like, I'm going to move there. I don't want to be like, I'm in the US I don't want to be in an expat bubble. I'm going to move there. I'm going to buy a house in the country. I'm going to be with the locals and so on. And nine out of ten times those people end up selling that house and moving into a bigger town or city because it's just really hard.
A
Yeah. Now, you talk to a lot of expats coming to Portugal. What are some of the. The biggest common hurdles you hear from them consistently about adapting to Portugal?
B
Oh, probably the bureaucracy. I mean, people think, oh, I've been to the dmv. I know what it's like. And it's on a whole other level here. Sometimes you just wonder, how inefficient can something be? So that is really hard, especially if you get caught in it. Some people aren't even caught in it, and they're like, oh, this was smooth for me. But sometimes when you get caught in it, it's like this closed loop. It's like, okay, for example, you need this number to get into this platform, but the only way to get that number is to do it on the platform. They won't help you in person. You have to go on the platform. And it's like, this is a closed loop, and it can be maddening. It can drive you crazy. So that is on a whole different level. Now, on the bright side of that, hiring someone to help is more affordable. So, like, for example, if you're, if you need a lawyer to help you with this, it's way more affordable than something like in the States it would be. So you, you know, you have some outs there, but I think the bureaucracy is on a whole different level. Sometimes you think, like, people don't, like, the Portuguese don't think outside the box when it comes to certain things. And then they say, oh, that's just how it is. That's just how it's always been, and there's no drive for a change or to make it better. And actually, I've gotten in a conversation with several of our younger Portuguese Friends who have also been expats, and they've seen how it's functioned, like, outside, and they're like, we have to stop making this like an excuse. Stop saying, well, this is how. It's. How it is, how it's always been. Like, we need to make a change. But there's still, you know, Portugal's still behind a little bit compared to other parts of Europe in this sense. So I think the bureaucracy thing is really, really hard for a lot of people. Another funny one that I think is hard is driving here. The drivers are pretty crazy, so, you know, drive at your own risk. But I feel like every time I speak with a friend who does have a car, like some sort of crazy driving conversation or, you know, something that happened to them comes up. So driving can be pretty crazy. Now, the good thing is, if you're in Lisbon, Porto, even some of the other bigger places, you don't necessarily need a car unless you want one. You can use public transportation or Uber and Bolt is affordable, but a lot of people want cars, so, you know, drive at your own risk. That's another one that I think is kind of funny. But, yeah, I think the bureaucracy is just one of the biggest hurdles that people have when they get over here.
A
Another hurdle for people who are deciding whether they want to leave their home country is children. What would you say to those who will say, oh, we're. We're about to have a child, or we already have children, and so that's it. We're. We're rooted in place. We. It's not feasible to go out there and change jurisdictions, travel around, move somewhere else. What would you say to those people?
B
I think that's a lie that we've been told for so long. Like I was saying before in our story, people told us all the time, go do this. Get it out of your system. We even had people say, because once you have kids, you can't do it. And we were like. We were working at an international school in Singapore, and we saw families do this all the time. Not with one kid, with two kids, some with four or five kids. And they were doing this. They were living a great life abroad. They were traveling a lot. They'd go back to the States to visit family and friends when they wanted. And so it's this lie that you can't do it, that you're rooted. You know, obviously, you have to do what's best for you. And if you're not comfortable doing it or you do find it too hard, you don't want to feel like someone's flipping, forcing you to do it. And it's really important that you're on the same page as your partner or spouse, because we've also seen that where one wants to move abroad and the other doesn't, and in most instances you end up going back to your home country. So that is really tricky. So you do want to be on the same page there. But it's absolutely doable to do this with kids. We have, we left the US with a nine month old, so. And we have friends. I have a story. They've got four kids now when they moved, two kids under the age of four. They were four and two. And she was pregnant and she was about six months pregnant when they moved and they moved here. And she actually ended up going into labor early. And they hadn't met enough friends to be able to have someone to stay with the kids in the middle of the night. So she went to the hospital on her own, had the baby while the dad stayed with the two kids. I mean, so you have stories and they're fine. And they've since already had another here in Portugal. So they've had two kids in Portugal. That's the other thing as well. Like, obviously people are having kids here, so hospitals are fine. You can have kids here. The good thing too is a lot of the doctors and nurses speak English, so you can make sure that you're comfortable and understanding what's going on. But if you feel like, you know, if someone tells you you can't do it because you have kids, I just think that's a lie. You just have to figure out if you want to do it. And if you want to do it, you can make it happen.
A
I think that's very well said. And you also talk a lot about the practicalities, you know, lugging children around in not just Portugal, but many countries around the world on your YouTube channel. There's lots of practical advice, which is why I recommend people definitely check that out. Give it a follow. And maybe on that topic, Kaylee, when you're in a new place, traveling around, what are, what are some things you've learned being such an avid traveler, of how you get up to speed upon arrival in a new place, in terms of getting comfortable with it, where you find, finding places to go, vetting it, maybe skipping past some of the, the TripAdvisor stuff. What are a few tips that you've learned over the years?
B
Yeah, I actually hate TripAdvisor when it comes to, like, things to do in a place. I I never look at the stuff there. So that would be one tip. When research, what I like to do is go to the people who are doing it themselves and, like, have blogs, because sometimes they'll have, like, paid things on there, like, you know, and. But then they'll put, you know, like, I get a commission if you click on this. But a lot I feel like is more authentic and structured compared to TripAdvisor that's all over the place. Or there's like, Viator or whatever that's just trying to sell you on these, like, tours and stuff. So the research you can do before is like, finding someone who's done it themselves and have blogs or, or vlogs, like videos and so on, making notes on that and what you want to do and seeing what, you know, cross references on, like, several different pages is like, okay, this must be something to do because three people have. Have talked about it before. But then also finding more of, like, the local restaurants and hidden gems. I think it's a little easier on there. The, you know, TripAdvisors sifting through. It's just kind of a pain. But really, I think the. The thing that makes your life the easiest by far is making sure as soon as wills touch down, you're connected on your phone. Like, when we first moved abroad, smartphones didn't exist. So literally, I printed out maps and we'd walk around with these maps on paper. And then Josh got one of those Garmin gps, which is. They were terrible. It had, like, driving and walking, and it was always wrong. It never knew where we were. So a huge, like, source of stress was we landed in a place and we have to find, like, our hotel or where we're going, and we just. There was no connection, like the way a smartphone is nowadays. And so it was always really stressful and awful when we did that. But now, because of technology, a good, good thing is, is you can actually stay connected. And there are E sims that you can set up before you go. I mean, some people buy like a sim once you get to the airport. That was like the Next wave thing to do once smartphones came out. Honestly, now I just think it's better to set it up before you go. So what you do is you just, obviously you get an esim. We use Airalo all the time. So. And that's what we'll do. Like, for example, we're going back to the US to visit. We'll just use Air low because our connection's only for Europe, not for the US and it's more cost effective than going through our European carrier. So even if you're coming on on vacation and you have a carrier that says, oh yeah, you can use it over in Europe, it's normally really expensive. So if you do an ESIM and you set it up beforehand, then literally as soon as you land, you can switch it over and you can get connected so you can have an idea of what the weather is like outside. You can use your map to figure out where you're going. You've already got Uber bolt set up so that you can just get a car rather than feeling like you might get ripped off in a taxi. So I think one of the best things you could do is have that set up, have that comfort. But then, you know, like a little research obviously beforehand. And then the other thing, it kind of depends on how you want to do things. Some people feel much better having a place booked before. Others like to just kind of go with the flow. So that's totally cool too. You just need to figure out, are you the type of person who's like, no, I want to make sure I've got two weeks in this hotel in the same city and then I'll go from there. Or are you like, you know what, I'm going to land, I'm going to have my first night at a hotel and then I kind of want to be fluid and figure out which city I'm going to go to from there and just kind of go with it. So just kind of make figuring out which person you are and what's going to work best so that you have a really good time.
A
That's really great advice. One of my tips is to try to have a contact wherever I'm going so that maybe they can pick me up, maybe they can show me around, certainly make it easier to transition into that, that city. Also for my audience, they're familiar with SilentLink, which is an ESIM service, crypto only, but it works anywhere in the world. As soon as you land, basically, you're just using that country's cell towers. You top it up. Not been to any country where it doesn't work. Apparently it also works in China, so SilentLink is definitely an option for the audience since this is a privacy focused channel. Kayleigh, I wanted to get your thoughts on this and if you don't have too many, that's fine. But I get a lot of questions recently about the EU Entry exit system, the ees where you're expected now to give your biometrics basically to enter the country. Do you have any thoughts on that? Maybe you could explain that to, to whatever extent you're familiar with it. And you know, is, is there, is there an opt out method or is this just the reality of, of traveling to Europe now?
B
Yeah, that's a good question. So it's mainly to track you. And I do not think there's an opt out, I just think they won't let you into the country. So essentially what's happened is since the EU is connected in certain ways, they were having issues with someone entering one country and then being able to seamlessly cross a border into another country, and then you're not able to track them for immigration, visa crime, whatever it might be. So that's why the EU decided to have this system where when you enter into one EU country, then you have to put your documentation and everyone in the EU now can access that. So if you come into Portugal from the us, let's say then you go through these automatic gates or this system, like they're still getting it up and running. So sometimes they'll automatic, you know, where you have to look at the screen and stuff. A lot of times it doesn't work, but so that it just spits out a paper that says, go see, go see an actual person. But either way, what they're doing, the actual person now is instead of it just being logged into their system for Portugal, it's going into this like massive log that is now, you know, Spain, France, Germany, all of them can access it. So from a privacy standpoint, if that makes you uncomfortable, then I think coming to Europe is going to be tricky because now all of the countries will be able to track, you know, it's your passport and you're like, depending on how many times you've done it, and if they ask for it, you might have to do your biometrics, so you might have to do your fingerprints and they take a picture of you. So just be aware of that, depending on how comfortable you are with privacy. But I, to my knowledge, there is no way that you can opt out of it.
A
Yeah, that's my understanding. And one of the good things about getting into Europe is once you get in, you can travel between all the countries and there's very little tracking that occurs once you're there. So you can travel around to all these different countries. You just have to get in the first time. So that's also something to consider. And also with the residency, if you, if you do get your temporary residency or your permanent residency, that's up, you know, that is Basically helps you to go around the EU as well. So you're kind of an EU citizen or not a citizen, but you're, you're, you're allowed to. And welcome to travel around to all these different countries, what, 26 countries or what have you. So it does open up a lot of freedom. But yeah, you're going to have to give up your biometrics to enter the country and that's just the direction that things are moving in. I wanted to ask you maybe, maybe a final question here. Maybe we'll have one more. Are there, we talked a lot about Portugal. Are there countries maybe complementary to Portugal along similar lines that you have your eyes on? Maybe probably in Europe, but maybe elsewhere. What are some other of your top countries that you think people should be considering?
B
Generally, when someone's looking at Portugal, they're also looking at Spain. There's so many similarities with the Iberian Peninsula, even when it comes down to visas and taxes and then lifestyle and weather. So Spain is a good one. Again, I think I mentioned it before earlier when we're talking about taxes. Depending on your tax situation, retirees can find favorable, favorable taxes in France. That's another one to look at. You do have Italy. Another good one for taxes is Bulgaria as well. So that's the other thing is Bulgaria and Romania have more recently, they've joined the EU a while ago, but it's always in stages. And so Bulgaria just recently adopted the euro. So that's nice. But overall cost of living, especially for like those who are digital nomads looking for a nice place now to be in Europe, part of the eu, but have a lower cost of living and they're okay with some of that cooler weather. Bulgaria is really nice. And then Romania is in the process, they still have their own currency that they haven't switched to the euro yet, but when that one comes in, that'll be a little easier too. But those are some that people are going that are a little more cost effective. And like I said, Bulgaria is really good for taxes, but a lot depends on, I guess. Obviously lifestyle is a huge thing. Like you want to look at these things like taxes and cost of living, of course. But then do you want to be living in a freezing cold place because the taxes are good and you're just miserable because you prefer warm weather. So you kind of have to, you can't just take it one piece. You have to put the whole piece together to see like all the pieces together, see what works best for you. So I think that that's really important that people need to consider. But overall I think that every, everyone can find something they really enjoy in a country. They just have to figure out what works best for them. And again, all those pieces that go together to make sure that it's what they thought it would be.
A
Excellent. So Kayleigh, thank you so much. The channel is expats everywhere. We'll have all the links and anybody who's listening and is motivated to take action definitely follow this channel. And I would also just consider going straight to a consulting session with Kayleigh to be maximally useful of your time and yeah. Any final thoughts, Kaylee, or anything we missed or motivational message? Your final thoughts?
B
No, no, I think this is great. Thanks for having me. And obviously for me, like, I'm not in like the privacy and crypto space, but I have heard, you know, Portugal, like you had mentioned, has got some stuff in the news, some good, obviously some bad with what you said. So I'm honored to be asked to be on here. And yeah, if anyone needs help moving, then I'm definitely available. And also too like whether it's kids or whether you feel like you're too old, like if it's something you want to do, everything is possible.
A
Hey, thanks for listening. I could really use your help. Real quick, if you could share this episode with someone, engage with me, leave a review anywhere. This helps me to break the technocratic shadow banning that is happening with my brand. And of course, if you really want to escape the technocracy, go to escapethetechnocracy.com privacy, tutorial, series, books, newsletters, consulting and of course you can leave a donation. Thank you very much.
B
Sam.
Watchman Privacy - Episode 225
Title: Expats Everywhere: All Who Wander
Host: Gabriel Custodiet
Guest: Kayleigh of Expats Everywhere
Date: June 29, 2026
This episode of Watchman Privacy centers on internationalization and enhancing personal freedom by moving abroad. Gabriel Custodiet interviews Kayleigh from Expats Everywhere—a YouTube channel dedicated to expat life, particularly focused on Portugal. They delve into the mechanics of becoming an expat in Portugal, the pros and cons, common hurdles, lifestyle tips, and broader considerations for those contemplating a geographic and jurisdictional reset for freedom, privacy, or adventure.
“After the first year or so in Spain, we're like, this is something that we could do. We found a way to... base ourselves in different parts of the world.” (02:58, Kayleigh)
Most Common Visas:
Path to Residency & Citizenship:
“It used to be that after five years here, then you could apply for citizenship. And now... for Americans, you have to wait for 10 years...” (14:54, Kayleigh)
Challenges:
“You have to have an accommodation lease... The problem is some people don't know exactly where they want to be or they want to explore... but they want a one-year lease." (11:44, Kayleigh)
Residency Visas:
Crypto Friendliness:
Mindset:
“You can't expect... to just pick it up and move and you're going to be happy and it's going to be exactly the same.” (19:39, Kayleigh)
Social Integration Advice:
Bureaucracy:
“Sometimes you just wonder, how inefficient can something be?... it’s like this closed loop...” (25:52, Kayleigh)
Driving:
Myth-busting:
“I think that's a lie that we've been told for so long... It's absolutely doable to do this with kids.” (28:22, Kayleigh)
Key Takeaways:
Travel Research & Connectivity:
“As soon as wheels touch down, you're connected on your phone... One of the best things you could do is have that set up, have that comfort.” (32:01, Kayleigh)
Finding Your Comfort Zone:
"If that makes you uncomfortable, then I think coming to Europe is going to be tricky..." (35:41, Kayleigh)
On Commitment to Internationalization:
“After the first year or so in Spain, we're like, this is something that we could do. We found a way to, to do it and to move around and to base ourselves in different parts of the world.”
— Kayleigh, 02:58
On Portugal’s Transformation:
“It was definitely like the hidden gem. It was a lot quieter than it is now... It's become popular a place to be.”
— Kayleigh, 04:00
On the Expat Mindset:
“Going with the flow of things, understanding that you've moved to a different country and it's going to be different. Looking at things in an optimistic outlook is really important...”
— Kayleigh, 19:46
On Adapting as an Expat Family:
“It's absolutely doable to do this with kids... If you want to do it, you can make it happen.”
— Kayleigh, 28:28
Advice for Settling In:
“Never look at TripAdvisor for things to do... Making sure as soon as wheels touch down, you're connected on your phone... One of the best things you could do is have that set up, have that comfort.”
— Kayleigh, 31:09 & 32:01
On EU’s Biometric Entry:
“If that makes you uncomfortable, then I think coming to Europe is going to be tricky because now all of the countries will be able to track... and to my knowledge, there is no way that you can opt out of it.”
— Kayleigh, 35:41
“Whether it's kids or whether you feel like you're too old, like if it's something you want to do, everything is possible.”
— Kayleigh, 40:42
For those considering expatriation, especially to Portugal, there’s never been more information or more demand—but also more bureaucracy. Preparation, realistic expectations, and community integration are key, and resources like Expats Everywhere can provide firsthand, practical assistance.