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Stop Overpaying Taxes: The Real Rules for Location-Independent Solopreneurs · The Life-First Solopreneur

• 0:00
  Carly Ries: Bobby Casey never had a real job. in fact, at 19, he started his first business and he hasn't stopped since. But it took a motorcycle accident, a week long coma, and a solo camping trip on the outer banks to ask the question that changed everything. What do I actually want my life to look like? From that answer, he built a career that travels with him across borders and a tax strategy to match.
• 0:21
  In this episode, Bobby joins Joe and I to cut through the myths around international taxes for location independent solopreneurs, the foreign earned income exclusion, why the hundred and eighty three day rule is mostly fiction, and why staying connected to your home state could cost you more than you think. So if you're thinking about designing a business that serves your life, wherever that life takes you, this episode is a great place to start. You're listening to The Aspiring Solopreneur, the podcast for those in pursuit of a life first business. I'm Carly Ries, and my cohost, Joe Rando, and I spend every episode with Solopreneurs who are proving there's a better way to run a one person business and experts who are helping make it happen. We like to say life first, then business.
• 1:03
  So let's get right to it. Bobby, we've been talking for about five minutes, and I'm like, this is a cool day. I am so excited to hear more of your story and everything that you do for people, especially around the topic of taxes, which I think some people are ugh, and I cannot believe we even have you here on April 13. Like do you need to go sleep or anything?
• 1:28
  But one thing I wanna do before we get started, I never read bios of our guests just because I think we lose people with that. But I just need to say why you're different with everything we're talking about today. And it is from your bio that was so interesting to me. So I'm just gonna say, he started, bought, and sold companies in multiple countries, so his stories are grounded in hands on learning, not just theory. He has also spent time actually living in 10 countries and traveling through more than 80 while building fully remote businesses.
• 2:03
  So he's not just talking about location independence as trendy. He actually lives it. He's all about showing practical steps that help solopreneurs design their business lives around freedom, compliance, and actual profit, not corporate templates. And I was like, oh!! Bobby welcome to the show.
• 2:22
  Joe Rando: Yeah. Sounds like a life first business to me. I'm assuming you like traveling.
• 2:28
  Bobby Casey: I love traveling and life first business is a good good way of putting it. And it wasn't always like this. so I've never actually had a real job. I've had my own business since I was 19. Like, I've never had a professional job.
• 2:46
  I said I've never had a real job. I mean, I've had jobs, like, as a kid. You know? I worked at the grocery store and the go kart track and unloaded trucks for UPS and stuff like that. But I've never had a real professional job.
• 2:58
  So for me, I always hear people say, oh, I had this corporate job making $250,000 a year, and I quit to start my own ice cream shop. And I'm thinking, you guys are nuts. Like, that's crazy. How do you give up, that lifestyle to switch? I just never had that. I don't even know what that would mean to have a corporate job.
• 3:19
  I would be completely an unemployable human at this point, like if everything burned to the ground tomorrow, I mean, I would probably just be homeless. I don't think I could actually have a job. so your point life first, it wasn't always like that because I had a company, in my twenties and early thirties. I mean, we had an office and, all the normal things. But I had a couple of big defining moments that happened around 2006 and 2007.
• 3:53
  And, I won't go into all the detail. One of them was a motorcycle crash where I almost died. I was in a coma for about a week. And, you know, you hear this story all the time, like, oh, you know, I almost died and I rethought my whole life and blah blah blah, this stuff. Well, yes, I did.
• 4:12
  I actually went on a camping trip by myself. well, I call it camping. I took an RV. I took my RV and went to Outer Banks in North Carolina for a week by myself and did a reflection week on, what I wanted or what I didn't want, and I realized a few things. Number one, my old businesses.
• 4:31
  I hated them, hated my customers, hated my employees, didn't want anything to do with it. Just hated everything about it. So I said, I'm gonna sell all these businesses and do what I want. And during that week, I kind of reflected on and journaled about, wrote about, meditated, whatever you wanna call it, on what I want. So, Joe, to your point, how did you put it?
• 4:53
  Life First, And so that was one of those moments where I realized, I looked at it. I really like your term life first. I actually came up with this analogy sitting on the beach in Outer Banks camping. And I came up with the analogy of a dart board.
• 5:13
  So you know a dart board has the bull's eye and then you have the rings around the dart board. Right? So I came up with this analogy that most people, almost everyone, myself included, had spent a long time with my career as the bullseye on that dartboard. And so what that means is the career is the most important thing in the structure of your life, and then everything else becomes like a ring around it. where you live, where you go on vacation, where you eat lunch every day, what your hobbies are, you know, all these things.
• 5:48
  Like if you live in Colorado, snow skiing might be a hobby. If you live in South Carolina, golf might be a hobby. You know what I mean? So geography plays a huge role in the way your life is. And if your business is location based, you're in a geography that determines what your life looks like. And I came up with that dartboard analogy back in I think this was 2006 or '7 or something like that. And I no longer wanted my career to be the bullseye. I wanted the lifestyle that I wanted to live to be the bullseye, and I wanted my business to be a ring. And my business had to fit my lifestyle instead of the other way around, if that makes sense.
• 6:35
  Joe Rando: Makes total sense.
• 6:36
  Bobby Casey: And one of those requirements was I wanted to be able to live and work anywhere in the world because I have been traveling a lot. I've got the travel bug big time. I still do. People ask me all the time, hey. Don't you think you're ever gonna settle down?
• 6:54
  I'm like, what are you talking about? I am settled down. I have three homes. I'm settled down in three places, you know, three different countries. That to me, that's settled.
• 7:03
  That is what settled Bobby looks like, having three home bases and only traveling to, 10 or 12 countries a year because before it used to be much more. So yeah. And I built everything from that point forward. I designed the business to suit my lifestyle that I wanted to live. And then, you know, there are a lot of things that go into that, but we only have forty five minutes to talk about it. But everything, that went into what I wanted my life to look like, you know, you always hear like, what's the perfect day. People talk about the perfect day analogy, and, I said, this is what I want my perfect day to look like. And I'm the kind of person that this is my perfect day to day, but hey, maybe Wednesday, I wanna go to Buenos Aires, and maybe I wanna stay in Buenos Aires for two weeks. Maybe I decided to stay for a month. Maybe in July, I wanna go to Thailand. and that's what I wanted my life to be. I didn't want to add those geographical boundaries or restrictions that said I couldn't do those things, and I knew, my work had to fit that.
• 8:09
  Carly Ries: Yeah. I am entranced by your story right now and just how I was a digital nomad for five years. So anytime somebody is like RV, because that was pivotal for me. I knew at that point, I wanted to be fractional and I wanted to be able to design a lifer. So question for you. you do a lot of international work.
• 8:32
  And it sounds like you figured it all out. But what were some mistakes you made along the way , like, cautionary tales for people that are thinking about doing what you wanna do. Maybe going place to place, one country a month or something. What would you tell them to be mindful of before they make that leap?
• 8:49
  Bobby Casey: So a couple of points. I was a digital nomad before that term existed. Digital nomadism in my opinion, maybe I'm wrong, but I think I'm right. In my opinion, kind of started around the invention of of Skype. So Skype was invented, I think in 2004 or 2005.
• 9:11
  Prior to Skype, it was very difficult to be a digital nomad, especially a solopreneur. and you make decent money, but you're not working for a billion dollar company that can pay your $3,000 a month cell phone bill, right? Like you don't have an expense account to pay your $3,000 a month cell phone bill. And prior to Skype, that was reality. If you traveled a lot, your cell phone bill is like $3 grand a month. I don't know if you guys remember back then, but if you traveled and you used your cell phone, if it even worked, it was like $8 or 9, $10, 15 dollars a minute to use the stupid thing.
• 9:49
  And so Skype came along and just eliminated all that. You can have video calls with your friends, your clients all over the world, and people are like, I'm not restricted anymore. And it opened up that world, and now, we have, all these technologies that allow us to do this. And then you also had the book that came out. You guys have probably read it or at least heard of it, the Tim Ferriss book, the four hour work week
• 10:14
  Which talked a lot about, working remotely and how you build systems for small businesses and stuff. So the digital nomad movement in my opinion started roughly twenty years ago. And I think it's been wonderful. I started about the beginning of that time. Remember, I didn't have Skype at first, and a friend of mine in Russia introduced me to Skype.
• 10:43
  I'm like, oh my god, this is amazing. I started using it pretty early. And to your point, some of the mistakes I made, I mean, I'm an entrepreneur. All our entire life is to go from mistake to mistake. Right?
• 10:57
  I mean, that's all we actually do. Like, that's what it means to own a business. all you do is try to fail forward to the next mistake and hopefully, you progress forward and you fail better each time. Right? In entrepreneurship, That's the whole name of the game,
• 11:17
  but as far as moving, I mean digital nomads too have kind of a range of definition. If you ask the hardcore, you know, 23 year old solopreneur or somebody that has a remote job was a digital nomad, and that would be, a person with no home base, and they live here for three weeks, and they live in this hostel for a month, and then they, go live in this work stay place in Vietnam for a month or something like that.
• 11:53
  Joe Rando: we have some of those in our group. I mean, they just don't have a home. They just go from place to place.
• 11:59
  Bobby Casey: Tend to be younger. They tend to be younger. They tend to also not have real businesses. They tend to be more of the solopreneur type, they tend to have like a remote job or something like that.
• 12:16
  Joe Rando: Wait a minute. You say that solopreneur isn't a real business?
• 12:22
  Bobby Casey: No. When I say a real business, I mean, a solopreneur is somebody who works, and I'm not disparaging it. A solopreneur is somebody who works and they are the business. They are the business.
• 12:36
  When I define a real business, I mean, you're building a company with systems in place where you can step away from that business, an employee based business.
• 12:47
  Joe Rando: Yeah. Employee based business. Okay.
• 12:49
  Bobby Casey: I don't really call it employee based, but systems based business where you have systems in place where things happen without you having to do it.
• 12:58
  Joe Rando: To clarify for the listeners, we are encouraging our solopreneurs to build systems just like you're describing in order to have a business that they can maybe not walk away from, but at least not be, engaged in making the thing, turning the crank on it twenty four seven, three sixty five. So we are really encouraging Solopreneurs to think in the context of what you're saying is a real business.
• 13:21
  Bobby Casey: Yeah. And we live in the greatest time ever in humanity to build these systems in place right now. My god. Look at what you can do with AI tools right now. Like, if you just dig in, you can create an army of employees with AI agents and, you can outsource.
• 13:42
  You're not even outsourcing. You're insourcing through AI tools a lot of the things you would normally be hiring for. So we live in the greatest time ever for, automating a lot of these things and putting systems in place. So what I mean by that, you got the younger 23 year old that is doing some kind of consulting thing and without his input, the business doesn't exist.
• 14:11
  That's what I'm talking about when I say they're not real businesses. you're a solopreneur, but you don't have these systems in place. So a lot of the younger people that are doing this three weeks here, a month here, two weeks here, they can do that because their income is really very often what I run into. And I speak at a lot of digital nomad events. Their income, it's like a lifestyle business.
• 14:40
  And there's absolutely nothing wrong with that. They live this lifestyle, and they make enough money to live that lifestyle, but they're not building a bigger company where they have these major systems in place and employees, and they're building a company that can be sold. Which is kind of the goal for a lot of entrepreneurs, eventually get to the point where you can sell your company. I just had a call, a client call before the show with a guy who's exactly that. He does consulting.
• 15:11
  He doesn't have a business he can sell. If he stops consulting, then the business goes away. But he makes a lot of money. he makes good money. He's got some systems in place.
• 15:21
  So that's kind of the digital nomads on that end of the spectrum. and that would be a lot of the purest digital nomads would say that's the only definition. I'm on the other end, you know, where I have home bases and I like to go and be in one place. I like to have a routine for a little while. I like to have my gym routine and the five restaurants I go to on a regular basis and that kind of thing.
• 15:50
  You could call that like digital slow matting is what some people call it. But there's a range of spectrum on what it means to be a digital nomad also. So when it comes to making mistakes, I think the mistakes on one end of the spectrum are very different on mistakes on the other end of the spectrum. on the digital slow mat side, I've seen so many people do this.
• 16:15
  It's so dumb. They're like, you know, I really think I wanna live in Portugal. I'm gonna go there and buy a house or buy an apartment. man, you've never even lived in Portugal. Calm down. you know, spend some time there first. But I see people do it all the time. I have client calls with people on my consulting business and they say, where should I move to? And how can I buy property there? I'm like, bro, you've never even been to this country.
• 16:43
  Like, why are you talking about buying property there? You might hate it. You may hate the food. You can't speak the language. you know, relax.
• 16:52
  So I think people make that mistake very often. But on the nomading side, I don't even look at it as, mistakes. one of my favorite quotes, and honestly, this is my life philosophy, is you only regret the things you don't do, not the things you do. So from that perspective, I've never made a mistake. I've had learning experiences,
• 17:21
  Carly Ries: If my husband's listening, same. I have never made a mistake. I'm always right.
• 17:28
  Bobby Casey: Sure. You have a lot learning experiences.
• 17:34
  Carly Ries: Well, question for you. Because we're talking about home buying and all this stuff. Money side of things is really interesting to me. I know this is like international tax is a big expertise of yours. if people are going overseas or whatnot, and are there a little bit longer than a little stay, like a working staycation for three weeks or so, Is there a structuring?
• 17:57
  I keep going back to the word mistake, but is there a way that they need to be structuring their business so it doesn't cost them? I mean, what are your thoughts there?
• 18:07
  Bobby Casey: Yeah. So definitely, like you said, to your point, if I'm gonna go dip my toe in the water and I'm gonna go, spend a month in Spain to see if I like it, no. Don't do anything different. You're on vacation. You're on a long vacation,
• 18:23
  But if you're beyond the point of dipping your toe in the water and you're like, I'm gonna sell the house and the cars and just sell everything and throw it all in my suitcase and begin this nomadic journey, then yes, you definitely need to think about the way your business is structured. Because from this perspective, now we can talk about mistakes. So one of the biggest mistakes people make when they begin this nomadic journey, full time, again, not dipping the toe in the water, but, diving into the life to live the nomadic digital nomad life. One of the biggest mistakes people make is not getting proper advice on how to do that from the business and financial side. Because what normally happens is, let's say you're an American and you wanna move abroad.
• 19:18
  You wanna be this digital nomad. You wanna go live, you know, Southeast Asia part of the year, Mexico, Colombia, whatever, some of the hot spots. And you say, well, I'm American. I'm just gonna keep myself based in The US. I'm from Chicago.
• 19:32
  I'll just keep my Chicago address and my Chicago driver's license and my Illinois LLC and so on and so forth. And you just keep that connection back to your home base, you call it. Well, it's not even a home base anymore because you've left. But a lot of times people emotionally feel like it's still their home base because that's where they're from. And they just move and are like, I'll just keep running my business through that Illinois LLC and I'll keep paying taxes in The US and all that stuff. I mean, you can do that. Don't get me wrong. Like, that's something that is available, every country. Like, you could be German and do the exact same thing.
• 20:11
  I had tons of Germans who have left Germany, but because they didn't know what to do, they just kept their business registered in Germany and kept themselves registered as a tax resident in Germany even though it wasn't necessary. But they did it because they didn't know any better, and they didn't go get proper advice to do this. I've recently had a client from Canada who did this. She makes a lot of money. She makes over $1,000,000 a year US.
• 20:37
  And she'd been out of Canada for almost ten years. And Canada's tax rate's very high. It's like almost 50%. And so she was paying close to half $1,000,000 a year in tax for the past ten years, and she could have been paying zero. Goose egg, zeros, for ten years.
• 21:01
  Half $1,000,000 a year. For ten years, she paid $5,000,000 in tax that was completely unnecessary.
• 21:08
  Carly Ries: So what did she do instead? Like, when she moved over, what are the other options?
• 21:12
  Bobby Casey: Well, we restructured everything for her. But the point was the mistake she made was not getting the advice early on to get it properly structured. I even told her, when we got on the call, or we did a series of calls, not one. It takes more than one hour to fix all this stuff. But over a series of calls, I remember telling her one time, listen, I've got really good news for you and I got some really bad news for you.
• 21:40
  The good news is we can fix everything and you can pay zero tax. You go, oh my god, that's amazing. I said the bad news is you paid about $5,000,000 in tax that was completely unnecessary. And that's like, nauseating to think, you just paid $5,000,000 in tax. You didn't have to pay. Like, think about that. oh god. I feel sick to my stomach.
• 22:05
  Carly Ries: Yeah.
• 22:06
  Bobby Casey: That's a huge chunk of money. So in her example, she's Canadian, and as a Canadian, you can exit the Canadian tax system. If you leave Canada, you can exit it. Unlike Americans, Americans cannot exit The US tax system.
• 22:24
  The US is what we call a citizenship based worldwide tax system. So you pay tax on worldwide income no matter where you live in the world. Americans have other opportunities. There are different loopholes you can take advantage of. There are things like the foreign earned income exclusion, foreign tax credit, and a few other things.
• 22:41
  But you're still a tax resident. Whereas Canadians, there's a list of things you gotta do. But if you check all the boxes, you can actually exit the Canadian tax system and have no more connection. You'd no longer file, you no longer pay, nothing.
• 23:00
  Once you exit, the important thing is, do you become a tax resident somewhere else? You don't necessarily have to be a tax resident somewhere. now that depends on nationality and there's a timing issue of that, like Canadians can easily exit without being a tax resident. If you're Finnish, there's a four year tax rule that if you exit the Finnish tax system and you do not become a verified tax resident in another country, you remain a tax resident of Finland for four years. But there are loopholes to get out of that too. It's just a different set of strategies you gotta use if you're Finnish. Same with Australians. They got a more complicated system to exit.
• 23:47
  But most of the most of the world, most nationalities can easily exit their home tax system without being a tax resident somewhere else. The tricky thing is is how do you avoid being a tax resident somewhere else? Every country has a different set of rules on what it means to be a tax resident in that country, and a lot of it has to do with your what they call your center of vital interest. Like, where do you kind of have your home base?
• 24:21
  So if you're like in this digital nomad lifestyle, it's easy. It's super easy to not have tax residency anywhere. Like, it's ridiculously easy to not have tax residency.
• 24:32
  Carly Ries: how so? do you just have to only stay a certain amount in each place?
• 24:37
  Bobby Casey: Yeah. You just move around. You just move around. Like, every country has their own set of rules on what it means to be a tax resident in that country. So it takes some strategic planning, and you have to think about, like, okay.
• 24:49
  I wanna spend time in, let's say, Thailand for a few months, and then I wanna go to Vietnam for a few months, and then I wanna be in Mexico for a few months, and, you know, using the Canadian as an example. And I wanna spend, summertime in Canada. Can I do that? Yes. You can be a zero tax resident in that scenario. But you gotta look at where you're spending time to make sure you don't do things that trigger tax residency in each one of those places. And it's complicated because every country has a different set of rules on what it means to be a tax resident. So, there's always the you know, there was I'm convinced there was a blog post written, fifteen years ago about this, and everyone uses it as a factual reference point. But everyone talks about if you're in a country more than a hundred and eighty three days, you're a tax resident.
• 25:39
  If you're not, you're good. That's not true. That's not true. Like, the 183 tax residency rule is a bullshit myth. It doesn't exist.
• 25:51
  I have read the tax residency requirements in probably a 140 or a 150 countries. I can tell you so not all 200, but let's say three fourths of the countries on the planet, I've read the rules on what it means to be a tax resident there. Of the ones I've read, I've only found one country that has a clear hundred and eighty three day rule for tax residency, and that's Ukraine. That's the only one. Like, Spain is an example. they have a hundred and eighty three day tax residency rule as one of their, dozen different criteria it takes to meet tax residency. For example, in Spain, if you own a home in Spain that's your primary residence, and even if you only spend a month a year in Spain, you're still considered a tax resident. Okay? Doesn't matter how many days you're in the country. However, if you're a tax resident, speaking of Spain now, if you're a tax resident of another country that has a tax treaty with Spain, you can live in Spain all year and not be a tax resident.
• 27:05
  So the point is, using that Canadian example, if she's gonna go just for, hypothetical examples, spend the summer for three months in Canada, three months in Thailand, three months in Vietnam, and three months in, oh, I don't know, Portugal, for example. So that's twelve months. Right? Yeah.
• 27:27
  I think I got all twelve. So in that example, she can easily not be a tax resident, but then you gotta look at, first of all, Canada, how do you make sure you exit correctly your your home tax system, and how do you make sure you don't by default become a tax resident again in Canada. Okay? And then you have to look at what are the rules for becoming a tax resident in Portugal and in Thailand and in Vietnam? Did I use Vietnam?
• 27:56
  Whatever example I used, Vietnam. So you have to look at each one. you can't just, I mean, you can. People do it all the time, and they live under the radar, and they do it illegally all the time. Like, it happens all the time.
• 28:09
  But if you wanna follow the rules and make sure you don't, put yourself in any situation, you need to actually have a proper plan in place to be like, okay, let's make sure I don't become a tax resident in Vietnam. Okay. What are the requirements? Okay. Don't do that, you know. What does it mean to be a tax resident in Thailand? Okay. I don't wanna do that. You know what I mean?
• 28:31
  Carly Ries: The the majority of our audience is US based. For that audience, if somebody's like, oh, man, this guy knows his stuff. I wanna do this. What would be two recommendations you have for US based audience to save on taxes if they wanted to be Become a nomad?
• 28:49
  Bobby Casey: Okay. So as a US person, your main loophole that you have to save on tax money is the foreign earned income exclusion. You can look up IRS form twenty five fifty five. If you look up two five five five with an I at the end, that's the instruction sheet so you can read all about it on the instruction page or you can just look at the form 2,555.
• 29:15
  That is the form you file with your tax return if you have foreign income and you can exclude it from your taxable base. So if you qualify for the foreign earned income exclusion or FEIE. So if you qualify for FEIE for last year, 2025, your first 130,000 is tax free of earned income. Earned income, specifically earned income. So job or your operating business or something like that.
• 29:49
  Dividends, capital gains, rental income, royalties, interest expense, stuff like that. Those do not qualify for FEIE, only earned income. So if you're an American and you live abroad, and all of your income is from dividends, you don't qualify. You still have to pay tax on dividends in The US.
• 30:08
  Doesn't matter where you are. You might end up having a situation. If you go move to another country in that scenario, you move to another country and become a tax resident there, you might be paying tax there and then you can take advantage of what's called the foreign tax credit. So you pay let's say you move to France and you pay tax there, and then you take that as a credit against what you otherwise would have owed in The US. But you still have to file in both places if you're a tax resident in France.
• 30:36
  But if you're gonna be a digital nomad and you have a solopreneur business, earned income presumably, you're gonna wanna take advantage of a foreign earned income exclusion. So that's 130,000 you can earn tax free. And I wanna clarify the point is, it is you that qualify, not your business. So if your business is an LLC in The US with a 100% US clients earning in US dollars, getting paid through Stripe or PayPal in The US. You still qualify for foreign earned income exclusion because you, as the human, qualify for that exclusion.
• 31:14
  Okay? So that's a big question I get, people think, oh, well, all my clients are still in The US. I don't qualify for FEIE. Yes, you do, because you as a person qualified. The other thing is there's a housing allowance that you get, which averages roughly $40.50 grand a year.
• 31:33
  And the good thing, if you have a spouse, let's say, you know, I'm a guy. So let's say I'm a guy and my spouse, let's say she's not working. She stays at home, but I make $300,000 a year. Well, I can pay her a 130,000 also because she also gets the 130. So now we went from $1.30 to $2.60 tax free.
• 31:56
  But the housing allowance is per household. so if we're obviously living together, then, we would only get that $40 total per household. So you get about 300 k ish tax free if you were if you were married. Or that you ought to be married, but if you were in a domestic partnership or whatever in your household, you can pay that person also. And also pay your kids, by the way.
• 32:24
  So you can up that a bit. Although the IRS might look at it a little weird if you got a seven year old you're paying a $130,000 to
• 32:33
  Carly Ries: They're so valuable.
• 32:33
  Joe Rando: Don't do it, Carly.
• 32:34
  Bobby Casey: Don't do it.
• 32:35
  Carly Ries: I know. Yeah.
• 32:37
  Bobby Casey: It'd be a little weird if you paid your kid a $130 a year to like empty out your trash cans and mop the floor, you know.
• 32:44
  Joe Rando: Might be what it took.
• 32:47
  Bobby Casey: It definitely costs that. That's true.
• 32:50
  Carly Ries: Well, Bobby, even within The US alone, aren't there also ways like, if you're a digital nomad from an RV standpoint in The US, can't you become a South Dakota resident or something and not have to pay income tax and like, what are some of the loopholes there within the country?
• 33:07
  Bobby Casey: South Dakota's an interesting point. So, yes. I mean, you can basically move your tax residency to a zero tax state. South Dakota is one option. South Dakota is a common option because South Dakota is the only state where you can get a driver's license with one day stay in the state.
• 33:30
  So South Dakota, like, let's say you're from California, you can move to South Dakota and move your driver's license to South Dakota, and the only proof you need is that you stayed one night in South Dakota, and that you have a mailing address in South Dakota. So actually in one of my companies, Business Anywhere, one of our products is a virtual mailbox offering and that's the only reason we have a location in South Dakota is for our clients that do that. That's literally the only reason we have a location in South Dakota. for the clients that move their driver's license to South Dakota because we can provide the mailing address for them to move their driver's license. I have countless clients that have done that in South Dakota. So the benefit there is South Dakota
• 34:16
  Let's say you're from a high tax state you know, and you're doing the RV thing, and you're from a high tax state like California. Well, the California tax system. California's incredibly aggressive. And by the way, if you are just gonna exit and do the RV thing in The US and you're from California or you're gonna leave The US to be a global nomad and you're gonna leave from California, you better do this. You need to exit California no matter what because I mentioned before the foreign earned income exclusion.
• 34:49
  We'll come back to that in just a minute. But the foreign earned income exclusion is only at the federal level. California, if you did that, you left California and went to Mexico half the year and Argentina half the year, the FEIE is only at the federal level. California, if you still had your driver's license there and an address there, you still have to pay California state tax. They don't care if you actually live there.
• 35:15
  You just have some paper connection to California and they will chase you. 100%. I've had clients that got chased in California and owed a ton of taxes, and they hadn't lived in California for years. But because they didn't move their driver's license out and their addresses out, California is like, no. No.
• 35:35
  You still have a driver's license and address here. We still think you wanna come back. That's kinda their mindset. Actually, their mindset is we just want your tax money, but you know, that's their excuse for the mindset. So if you're gonna do the RV thing around the country or leave The US either way and you're from California, the initial step is the same thing.
• 35:57
  Move your driver's license, move your address, change everything in public record to a non California connection, and exit that state. And South Dakota is a good option for that because you can move your driver's license with a one day stay. Now what makes South Dakota a little bit tricky is , they crack down on South Dakota, by the way. So this is where it makes it a little bit tricky. But South Dakota is completely fine if you have your own business, you're a freelancer, you're a solopreneur, you run a company, whatever.
• 36:32
  It's completely fine. But if you have a remote job, South Dakota does not really work because if you move your residency there for the purpose of getting a driver's license, but you don't actually have that physical connection there, you cannot use South Dakota as your state of residence for employment. They will reject it. that's only happened in the past couple years. They will not allow that and your home state will look at that and see, oh, well, you don't actually live in South Dakota.
• 37:10
  So, we're pulling you back into our state from a payroll tax perspective. So if you have a remote job, you're a w two person, South Dakota doesn't work.
• 37:22
  Carly Ries: Which I don't think anybody in this show is.
• 37:25
  Bobby Casey: I'm just making a point for anybody listening just in case, but if you're a solopreneur, South Dakota's great. Because it's your business. You don't have to have like an LLC in South Dakota. You can have a Florida, or a Wyoming, or Nevada LLC, it doesn't matter. But you need that driver's license and that address in South Dakota to have that connection.
• 37:48
  I wanna jump back to FEIE real quick because to qualify for FEIE, there are two ways to qualify. The first one is you have to physically be outside of The US three hundred and thirty days in a twelve month period. Physically out of the country, and that includes transit days. and they're pretty strict on this. So you have to be a maximum of 35 in The US, including transit days.
• 38:17
  So that's a little restrictive for a lot of people. They're like, yeah, but what if grandma gets sick and I need to come take care of grandma for a couple of months or something? So that's the one way to qualify, that's called the physical presence test. The other way to qualify, which I believe is a much better option, but it involves jumping through more hoops, is called the bonafide residency test. And that means actually legally immigrating to another country and getting a residence permit or a residence visa or something in the other country.
• 38:49
  If you do that, if you go qualify for bona fide residency in this other country, now you don't have that thirty five day limitation in The US. Actually, it's way more subjective. I could even show you the IRS page on that, and the words are your connection to that other country is based on your intention about your length and nature of stay in that other country. It's all subjective words. There's no hard determination on how many days you need to be there or here or whatever.
• 39:22
  It's just about what they call your center of vital interest or your connection to that place and your center of vital interest and connection to The US. So I think going and getting residency in another country is a much better option because it gives you a lot more flexibility and it's easier, but choose wisely. Like, don't choose Denmark, one of the highest taxed countries on earth. don't do that. you wanna choose a country that either is what we call a residency based territorial tax system, meaning you only pay tax in that country if you earn income within that territory. Costa Rica is an example of that. They're a residency based territorial tax system. Or you can choose like, this is more expensive, so more for higher net worth people that you could go get residency in a place like Cayman Islands, which has zero tax. But it's a lot more expensive to get residency in those places like Cayman and BBI. And the other option is you get residency in a country where it's difficult to actually fulfill the requirements to become a tax resident of that country.
• 40:39
  So, Mexico is a good example of that because Mexico has a lot of loopholes protecting, especially like Canadians and American snowbirds who come down to Mexico, and they don't wanna, force them into a tax trap in Mexico because then it might disincentivize them to come down to Mexico and buy vacation properties and stuff. So Mexico has a lot of loopholes. You can be a resident without actually having a tax obligation because it's difficult to become a tax resident there yet. There's a list of things you have to do to become a tax resident. So you gotta be careful if you're gonna go the bona fide residency route, which country you choose to get residency in because you don't wanna trade high tax for higher tax.
• 41:27
  You know what I mean?
• 41:28
  Carly Ries: Bobby, I feel like we need a part two because I can talk to you about this stuff forever and it's so helpful. But I wanna be a researcher of your time. I feel like this is a good place to start wrapping things up. But this has been so helpful. We always end the show with our guests giving their favorite quote about success.
• 41:46
  You already said yours. Can you repeat it from earlier unless you wanna say a different one?
• 41:50
  Bobby Casey: Well, that's not exactly my quote about success. That's My life philosophy. Yeah. That's my life philosophy. You never regret the things you do, you only regret the things you don't do. That's a life philosophy. That could be about business, that could be, hey, I regret not starting that company. I regret not making that investment. It could also be, I regret not kissing that girl. Right? it can be a whole range of things. so my life philosophy is I don't do that. Like, if there's something I wanna do, I do it because I don't wanna have regret about it later, so I just do it. and that's kind of the live in the moment, kind of philosophy a little bit. I'm not Buddhist, but this kind of Buddhist philosophy that, we live in the moment and today is what we have.
• 42:49
  So that's more of a life philosophy. My probably favorite success quote is you only fail when you quit. Like that's because as entrepreneurs literally we fail all the time. But if we launch a business and it fails and we quit, yeah, we're done.
• 43:11
  That's it. If we launch a business and nobody likes the product and we tweak it, and we tweak it again and we tweak it again and now people wanna buy it, well, we didn't quit. We kept going and eventually we got there. I mean, that has to be obviously with some limits. If your business ideas to start a business making horse carriages, it's probably not a great business model to get into these days.
• 43:33
  Joe Rando: I'm not Sure. Like, my millennial kids are into vinyl records , Cassette tapes.
• 43:40
  Bobby Casey: Retro stuff is coming back. Yeah. That's for sure.
• 43:43
  Joe Rando: Film cameras. So maybe buggies is actually a good business.
• 43:47
  Bobby Casey: Yeah. Maybe we could get back. That's what we need, Joe. We could get back into the horse and buggy business.
• 43:55
  Carly Ries: Bobby, this has been, like I said, so so fascinating. Where can people learn more about you, your businesses, everything?
• 44:03
  Bobby Casey: So our consulting business, so from the consulting side, we work predominantly with location independent entrepreneurs who either live outside of their home country or have business outside of their home country or investments or something like that. And then we do strategic planning and consulting on company structure, tax planning, asset protection, residency planning, stuff like that. So that business is globalwealthprotection.com. And then my other business, which is kind of my main focus, so lobal Wealth Protection, we do still take clients, but we don't promote it. We don't market it.
• 44:45
  We run zero ads. We do zero promotion of that business. that only comes either through referrals or maybe I mentioned it on a podcast like this. The business we actually focus on is businessanywhere.io. And we are a registered agent in The US.
• 45:06
  We cover all 50 states plus the territories. We do company formation. We have virtual mailbox service. We facilitate a lot of other things within our platform. We're basically a software business, like a SaaS business.
• 45:21
  So you can open bank accounts in our platform. You can set up your bookkeeping, tax filings, virtual phone numbers, register trademarks, all the company compliance. I'm very adamant about entrepreneurship. I live, breathe, eat. Everything for me is entrepreneurship.
• 45:47
  I've never had a job. I don't even have friends that had jobs. Like, literally, I don't know anybody that has a job. And all my clients are entrepreneurs, so I'm very passionate about entrepreneurship. And Business Anywhere is a platform to make the tedious things in your business easy and automated. we automate all your compliance, for example. And what does every entrepreneur hate? Paperwork, compliance, legal issues. We all hate that stuff. Right?
• 46:16
  Entrepreneurs, all we ever want to do is the next sale, the next hire, the next deal, the next trade show, the next product launch, and somebody says, you need to clean up your bookkeeping. You're like, gross.
• 46:31
  Joe Rando: Yes, Sure
• 46:33
  Bobby Casey: Yeah. Sure. You're right. probably tomorrow, next week. So our platform is built around making those tedious tasks for entrepreneurs easy, simplified, and much of it automated. So like, if you're a plumber from New Jersey, you can certainly register an LLC with us, but our message is more towards, location independent entrepreneurs.
• 46:57
  Carly Ries: Sure. Oh, Bobby, so so cool. Thank you so much for coming on the show today. I think this information is just so invaluable, and so few people know how to do all of it correctly. So thank you so much for being here.
• 47:11
  Bobby Casey: Thanks for having me, Carly. Thanks, Joe.
• 47:13
  Carly Ries: And listeners, thank you so much for tuning in. As always, leave that five star review. Help spread the word to other people that wanna be digital nomads in whatever way that is for them, because they'll need this information. Subscribe to the show on your favorite podcast platform, including YouTube. And again, share this episode with a friend, and we'll see you next week on The Aspiring Solopreneur.
• 47:35
  You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.