Five Flags Update – March 2020

Here’s where I am currently on my five flags plan to move out of the USA in 2021.  

A while back I had discussions with some of my advisors (coaches, consultants, and attorneys). There was a consensus that I was being way too public regarding my specific plans about where I was seeking residency, where I was seeking passports, where I was planning on moving, and various other aspects of my five flags plan. The concern was if I kept blabbing about my plan, some of this public information could actually hinder my progress. 

So, after much discussion and thought, I very reluctantly agreed that I would stop giving quite as much specific detail involving what I’m doing. It really bothers me that I have to do this. As longtime readers know, I like to be an open book to my audience as much as humanly possible. For the same reasons I explain in detail here, I need to be a little careful about what I tell the entire world concerning my five flags plans for legal and governmental reasons. 

That doesn’t mean I can’t tell you anything. I’m still going to talk about it as much as I can. Some things I can be specific about, other things I can’t talk about at all publicly, and some other things I can tell you but only after I actually do them. Most of the things in that third category will be done by mid-to-late 2021, so it’s not like you’ll have forever to wait. 

So, with that out of the way, here’s what’s going on. 

Based on several discussions with experts in this area, including my friend Andrew Henderson of Nomad Capitalist, I have changed several major aspects of what I was planning last year. To recap, here was my old plan: 

  1. Move out of the USA in 2021. 
  2. Spend around four months a year in the USA, around six months a year in my new Country A, and the remaining months traveling abroad. 
  3. Designate New Zealand as my home base and Country A. 
  4. Seek residency and hopefully citizenship in Panama, Paraguay, and Italy. 
  5. Get a farm in Paraguay. 
  6. Offshore my businesses structures to countries in Eastern Europe and Asia. 

Several of these things have radically changed while some are the same. Here is as much as I can tell you regarding these changes. 

Move out of the USA in 2021 

Status: Unchanged and locked-in.  

This is still the case, and at this point is pretty much locked-in, in that I couldn’t change this if I wanted to (without incurring massive expense and disruption). As of January 1st, 2021, I’m outta here! “Outta here” means I will only spend a few months a year inside the USA, not that I will leave it completely. Pink Firefly and I will be spending winters in Scottsdale, Arizona. Outside of that, I won’t be in the USA at all. This year, 2020, is my last full year in the United States, perhaps forever. (Not that it will be a huge change, since I already spend several months a year traveling abroad. I was in almost 20 different countries in 2019 alone.) 

Spend around four months a year in the USA, around six months a year in my new Country A, and the remaining months traveling abroad. 

Status: More less the same with a few changes 

Instead of spending four months a year in the USA, I will actually be spending less time than that. Specifically, less than 100 days per year, which is around 3.3 months. This is a requirement for tax reasons that I can’t get into. This change was a little jarring since I was planning on “weaning” myself off of the USA, mostly to help Pink Firefly adjust a little easier, but four months was too long. Not a big deal. 

Designate New Zealand as my home base and Country A. 

Status: Completely changed.  

There was nothing inherently wrong with living in New Zealand, but my research found another country that is far better for my needs, far more exciting, much easier to travel to, a far better location for traveling to other countries, and much less risky for possibly incurring tax problems. Unfortunately, I can’t tell you where this country is yet. Once I’m there and settled, it will be pretty obvious, but for the time being I need to keep this to myself. If you want a hint, I’ll be moving to a city that is in my top five favorite cities in the entire world (no, it’s not Hong Kong). I am really, really excited. 

As of January 1st, 2021, I will be living in this country for at least five months out of the year, likely six or seven. I’ll talk more about this when I can. 

Seek residency and passports for Panama, Paraguay, and Italy. 

Status: Somewhat modified. 

Here’s the breakdown. 

Panama: I am still pursuing residency there, which is more or less guaranteed. I am also hopefully getting their passport a few years down the road, of which my odds of success are around 60%. 

Paraguay: I am still pursuing residency there, which is more or less guaranteed. I will not be getting a passport there due to various laws that have changed there recently. It’s distantly likely that a passport might be an option many, many years down the road but I’m not planning on it. 

Italy: I am pursuing ancestral citizenship there (a passport), but it’s complicated because of the Italians in my family tree. Odds of success are around 30%, but the good news is that if it works, I’ll have a passport in my hands in about 12-18 months, making that the first of my new passports. 

I am also now pursuing two more passports in two additional countries that I can’t disclose at this time. These two countries require me to invest in certain assets in their country, and then I’m almost guaranteed a passport within three years from both of these countries. Moreover, one of these two countries are where I was going to invest anyway, so this works out perfectly. Even if, by some bizarre chance I don’t get these passports, my investments will produce a very nice return, making this a no-lose scenario for me. 

At the moment I’m pursuing four different passports outside of my current American one. Odds of success for each one is 60%, 30%, 95%, and 95% respectively, so I should be able to get at least two out of the four, which is my objective (two passports in addition to my American passport for a total of three). 

Get a farm in Paraguay. 

Status: Completely changed. 

Alas, the capital I was going to use to purchase my Paraguay farm needed to be redirected to the investments in the two countries I described above, which is what I am now doing. I still want a farm in South America which has always been a part of my long-term plan, so I haven’t canceled this; I’ve just deferred it back to its original spot in my plan. Whether or not that farm will be in Paraguay or some other Latin country, I’m not sure. I still really want it to be Paraguay since I have fallen completely in love with Paraguay and now consider that country as one of my core flags. It has officially become my “retreat and relax” country. 

Offshore my businesses structures to countries in Eastern Europe and/or Asia. 

Status: More or less unchanged.

I have now determined exactly where my business entities will be (there will be more than one) and exactly how they will be structured. I can’t tell you what I’m doing here and probably will never be able to discuss this publicly. Join the SMIC Program or the Alpha Male 2.0 Focus Program; I can talk about this stuff with the guys in these programs and I have. I just can’t discuss this with the open public. The bottom line is that once these structures are complete, and they will be by the end of this summer, I will actually save more money in taxes than I was originally planning (FUCK YES!) and they will offer a huge amount of asset protection. Win, win! 

I will continue to update all of you on my progress and reveal as much as I can. I’ve just started my last full year in the Collapsing USA, so I’m finally headed into the home stretch! It’s the culmination of a plan I started working on eight years ago and started thinking about 17 years ago. Needless to say, I’m excited as hell. 

More soon. 

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21 Comments
  • Old Grump
    Posted at 05:32 pm, 12th March 2020

    Hi Caleb    –

    I might just get outta the USA before you!  If all goes to plan, we’ll be in SE Asia no later than January, 2021.

    I do have one question for you.  (Yes, I did post this on an old article on your other blog.  Not trying to be spammy; just curious if there is a solution.)

    One issue with international traveling that I find vexing is dealing with banks here in the USA. I just had one of my checking accounts hacked, (easy to do – all you need is bank routing number and checking account number), and I had to go IN PERSON from several states away to resolve this problem.  How would you handle this if you were on the other side of the globe?

    Thanks!

  • Investor
    Posted at 04:47 am, 13th March 2020

    go IN PERSON from several states away to resolve this problem. How would you handle this if you were on the other side of the globe?

    Find a bank that does not require it? Easy.

    If you want a hint, I’ll be moving to a city that is in my top five favorite cities in the entire world (no, it’s not Hong Kong). I am really, really excited.

    Did you post somewhere your fav cities? I believe a couple of them are in south/central america and you like Singapore but dont like the climate, maybe Australia but that wouldnt be easier to travel to. Must be in east asia /europe or central america to fulfill that requirement. Can you tell why you cant disclose it? Seems weird and like youre just saying it appear more mysterious.

    Offshore my businesses structures to countries in Eastern Europe and/or Asia.
    Status: More or less unchanged.

    Nomad capitalist and some others heavily recommends Georgia (if you can consider that eastern Europe) and to me Estonia seems like a good option I might look into later. In Asia I am guessing Singapore or HK?

    I am also now pursuing two more passports in two additional countries that I can’t disclose at this time. These two countries require me to invest in certain assets in their country, and then I’m almost guaranteed a passport within three years from both of these countries.

    There are a few such options I know of in the Carribean / latin america. I guess this is close enough for you from Panama so almost same things.

  • Caleb Jones
    Posted at 02:06 pm, 13th March 2020

    One issue with international traveling that I find vexing is dealing with banks here in the USA. I just had one of my checking accounts hacked, (easy to do – all you need is bank routing number and checking account number), and I had to go IN PERSON from several states away to resolve this problem. How would you handle this if you were on the other side of the globe?

    Use multiple banks. If there’s a problem with one of them, you can just shut down or de-fund the account(s) and use other ones with zero disruption. I’ve already done this at least once.

    Did you post somewhere your fav cities?

    I’ve talked about my favorite cities all over the place, but I don’t think I’ve ever ranked them in order.

    Can you tell why you cant disclose it?

    I just did in the above article. My attorneys instructed me that if I made it public before I actually moved there I would run the risk of screwing up my tax plan.

    Seems weird and like youre just saying it appear more mysterious.

    Incorrect. I would get more traffic, clicks, and engagement if I openly revealed the country right now. Again, I want to disclose this stuff. Badly. I just can’t. (Yet.)

  • Pseudonymous User
    Posted at 03:27 pm, 13th March 2020

    I’ve talked about my favorite cities all over the place, but I don’t think I’ve ever ranked them in order.

    I’m having an absolutely fantastic time here, and Dubai now officially ranks as my third-favorite city in the entire world, right under Hong Kong and Shanghai.

    It would be hilarious if the choice were indeed Dubai, especially if JOTB weren’t banned.

  • Caleb Jones
    Posted at 04:01 pm, 13th March 2020

    I’m not saying a word. 🙂

  • Ted
    Posted at 02:47 am, 14th March 2020

    Long time reader and watcher of both you and Nomad Capitalist, but never posted anything. But I am very curious about exactly what its like working with Andrew?

  • Caleb Jones
    Posted at 09:36 am, 14th March 2020

    Long time reader and watcher of both you and Nomad Capitalist, but never posted anything. But I am very curious about exactly what its like working with Andrew?

    So far it’s been great. My plan is to do a collaboration with him on something in the near future.

  • Alex
    Posted at 12:00 pm, 14th March 2020

    I’m not nosy about caleb’s plans but have been thinking about the same topics myself. Australia and NZ are culturally very close to the US so I don’t see the point of moving there. London and Berlin are quite nice to live in although the EU is in trouble. (UK is out but still have the immigration problem.) This leaves SEA in particular Singapore and Hong Kong. Latin America is nice for spending time and even getting residency but I’m not sure they are viable for making money.

  • Caleb Jones
    Posted at 12:47 pm, 14th March 2020

    Australia and NZ are culturally very close to the US so I don’t see the point of moving there.

    Australia and NZ are going to stagnate due to pyscho left-wing economic policies, yes. At the same time they are the only two Western nations not destined for collapse because of their lack of debt and proximity to the Rising East. The only issues moving to these two countries for the Alpha Male 2.0 is that they are high-tax and in many regions are stupidly expensive (coughSydneycough).

    London and Berlin are quite nice to live in although the EU is in trouble.

    No Alpha Male 2.0 should live anywhere in most regions of Europe for the long-term in my opinion and should get the fuck out. Germany is probably the worst.

    This leaves SEA in particular Singapore and Hong Kong.

    Anywhere in Asia is good (with the possible exception of dying, corporatist Japan which is collapsing). The issue there is budget; cheap guys can live in SE Asia, higher-income guys can live in Singapore or HK if they don’t mind the extra cost.

    Latin America is nice for spending time and even getting residency but I’m not sure they are viable for making money.

    The Alpha Male 2.0 has location independent income so the business/economic conditions of where he lives (outside of tax concerns) are mostly irrelevant. South America is fantastic. Just sell to Westerners or Asians while living there.

  • Pseudonymous User
    Posted at 04:14 pm, 14th March 2020

    Could you please explain these seemingly contradictory statements?

    No Alpha Male 2.0 should live anywhere in most regions of Europe for the long-term in my opinion and should get the fuck out. Germany is probably the worst.

    but

    The Alpha Male 2.0 has location independent income so the business/economic conditions of where he lives (outside of tax concerns) are mostly irrelevant.

    Why is it inadvisable to live in places such as Germany when not only its possible economic decline won’t have an effect on the location independent revenue stream, but it will also enhance the purchasing power of said stream?

  • Caleb Jones
    Posted at 04:37 pm, 14th March 2020

    Why is it inadvisable to live in places such as Germany when not only its possible economic decline won’t have an effect on the location independent revenue stream, but it will also enhance the purchasing power of said stream?

    For reasons outside of income from customers, including…

    1. I said “outside of tax concerns.” Most collapsing Western governments will attempt to increase taxes to bail them out, and I include Germany and most of Europe in that category (as well as the USA post-Trump).

    2. Europe and Germany in particular is facing systemic collapse of their banking system. This would indeed be a problem for an Alpha Male 2.0 living in Europe (unless he had a heavy five flags system already in place and did 100% of his banking outside of Europe; then I guess he’d be okay but that would be an exception to the rule even for Alpha 2.0s).

    3. Civil unrest is also possible in many parts of Europe over the next several years as its collapse continues.

  • Investor
    Posted at 05:14 am, 15th March 2020

    It would be hilarious if the choice were indeed Dubai, especially if JOTB weren’t banned.

    That has crossed my mind too but I wouldn’t think Caleb would like the climate. I recall he hated that about Singapore also?

     

     

  • Alex
    Posted at 12:14 pm, 15th March 2020

    Yeah civil unrest in Europe is a big concern. Can happen here too.

    I forgot to mention Canada…and so Paraguay doesn’t easily give citizenship anymore?

  • Alex
    Posted at 03:04 pm, 15th March 2020

    One more thing: Have you written on how to go about setting up such a business? (I’ve read Unchained Man.) Living in LATAM or SEA and selling to Westerners seems complicated in terms of both law and operation.

  • Caleb Jones
    Posted at 03:04 pm, 15th March 2020

    Paraguay doesn’t easily give citizenship anymore?

    It’s still easy compared to most other nations but it’s not nearly as easy as it once was. Now you have to spend at least 9 months a year there for 3-4 years before they’ll give you citizenship. I can’t spend nine months a year in Paraguay so that won’t work for me. I’m still going to get residency there though; that should be done by the summer.

  • Redbaron
    Posted at 10:42 am, 17th March 2020

    2. Europe and Germany in particular is facing systemic collapse of their banking system. This would indeed be a problem for an Alpha Male 2.0 living in Europe (unless he had a heavy five flags system already in place and did 100% of his banking outside of Europe; then I guess he’d be okay but that would be an exception to the rule even for Alpha 2.0s).

    3. Civil unrest is also possible in many parts of Europe over the next several years as its collapse continues.

    I expect Deutsche Bank to go under in the COVID-19 inspired recession that is current descending upon the Western World given their horrid financials and the fact that they keep hemorrhaging thousands of jobs on a regular basis.

    As for the civil unrest, its already begun in France with the Yellow Vests movement, and the bans on gatherings imposed by French government has done nothing to slow it down. It is guaranteed at this point that what’s going on in France will spread to the rest of the EU countries over the next decade.

  • Chili
    Posted at 06:59 pm, 23rd March 2020

    I’m right behind you, if not ahead. I want to leave the country this year, but we’ll see how it works out. I am also going immediately to the less than 330 days in the country route. New Zealand is still nice, although they have closed borders to non-residents and non-citizens thanks to the virus panic, so that will have to wait, and I do have a few other countries in mind as New Zealand is one of those sanctuary countries that everyone will try to flock to if shit hits the fan. Always have a backup plan.

    I’m glad to see a lot of Caleb’s advice getting real-world application right in front of me. It really bridges the mental gap between the abstraction of lessons across the internet and the reality of what’s happening.

  • zech
    Posted at 04:47 am, 26th March 2020

    Based on the selection of the countries, you don’t put too much emphasizes to the healthcare especially in case of semi-emergency where you can’t or are unable to go to a private clinic.

  • Mark C Brooks
    Posted at 05:20 am, 4th April 2020

    Those are some ambitious plans. I hope that everything works out for you. Personally, I lived in Asia for 15 years: five years in Tokyo, five in Hong Kong and, after I retired, I split my time between NYC and Manila. My rent in Tokyo was $7500 a month. (Paid for by my employer.) I had a beautiful duplex apartment with two terraces in the high end area of Omotesando. Tokyo was a real eye opener for me. I had never slept with so many seriously pretty women – Japanese and foreigners. It was all so easy. In Hong Kong my rent was also $7500 a month. Again, paid for by my employer. It was a pleasant, fully renovated apt in a prime location in the Midlevels but was really not all that special. Really nice apartments in Hong Kong run about $10 – 12k a month. (Just like in NYC where no one wants to live in Brooklyn, in HK no one but the Chinese and TEFL teachers live in Kowloon.) Again, a real eye opener. My introduction to Thai, Viet and Filipina women. All I can say is Ohh la la.

    Personally, I don’t like Singapore. Mostly dull, flat and boring. The local women are not all that attractive. And, as already pointed out, the weather in Singapore is hot, humid and dreadful. (Although I did have a lot of fun in the bars in Orchard Tower.) I liked Shanghai. Many long weekends staying at the great Park Hyatt in Jinmao and partying on the Bund. I couldn’t see living there though. Too many Chinese and again, the local women are mostly not so great looking. (And not that good in bed.)

    For anyone looking for an alternative within a reasonable budget I would recommend checking out Manila. The city has a bad reputation for being third world, traffic from hell and urban blight but I think that you might be pleasantly surprised if you get the lay of the land right. During the time that I lived in Manila I rented a duplex penthouse apartment in Makati with just astounding views. The rent, with utilities, came to about $2,000 a month. A comparable apartment in Hong Kong would be at least 12k a month.

    Plus, I really dig the Filipina chicks. More curvy than their Thai and Viet counterparts and much better in bed. Plus, they speak fluent English – not that baby gibberish most of the Thai chicks speak. I mostly date 7.5 – 8.5 girls in the Philippines. There are some real stunners here (true 9s), but they’re well out of my league.

    About 18 months ago I sold my penthouse apt on Central Park South and moved to South Beach, Miami. (Now that city has some beautiful women – but a bit too much silicone enhancement for my taste.)

    Its too bad that you can’t attach pictures on this site. I’d like to show you just how nice Manila can be. Anyway, all the best …

  • ELT
    Posted at 09:37 pm, 16th April 2020

    Its too bad that you can’t attach pictures on this site. I’d like to show you just how nice Manila can be

    Hey, Mark, any chance you could share those pictures from Manila elsewhere? I’m very interested.

  • TK
    Posted at 05:14 pm, 13th June 2020

    Caleb,

    Your five flags topics are ones I enjoy most, thanks for the great writing.

    I’m curious- what are your thoughts on Iceland as a viable 5 flags country? I wonder because it seems remote like Australia and NZ. Or is it too close to the Western collapse?

     

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