If you’re unfamiliar with what five flags is, read this. The nutshell is that it involves living abroad and spreading out your businesses and finances internationally to increase freedom, increase diversification, increase long-term security, and lower your taxes.
Is five flags for everyone? Can any man do it? Should every guy do it?
No. It’s not for everyone. It’s only for certain types of men. Five flags is amazing and I highly recommend it for those types of men who can benefit from it, but at the same time, five flags is complicated, time consuming, and in some cases, expensive.
Who, then, is five flags for?
In my view, five flags is only for the following types of man:
1. Men with no baggage. This would be men with no corporate job, no wife, and no kids (or older kids who are all grown and gone). These men are reasonably mobile-capable even if they’ve never traveled internationally before. They can quickly execute any type of five flags plan they like with far less hassle than normal guys.
2. Men who are already digital nomads or perpetual travelers. Five flags is the easiest for these guys because they’re already living an international lifestyle to begin with. Five flags is just a few tweaks for these guys.
3. Self-employed men with high incomes. This is the category I’m in. Five flags is probably the best legal way to drop your overall tax burdens to near zero. If you’re busting your ass, working seven days a week, making $400,000 a year (or whatever) and you’re paying $180,000 of that to the US government… well, fuck that. That makes no sense at all. Go five flags (which will take a few years, but it’s worth it) and you can drop that $180,000 tax bill to $30,000 or way less, legally. Many of these guys can literally double their take-home incomes by just making a few five flags changes.
How much money should you be making before you consider five flags as an option? I would say once you’re at the $200,000 per year level you should at least start looking at it, and if you’re at $300,000 or more I don’t see any reason not to do it unless you absolutely love living in your home country or you have some kind of family limitation you can’t get around. But that’s just my opinion.
4. Retired men. Retired guys can benefit from the tax savings of five flags and they don’t have the life infrastructure (like jobs and kids) of younger men, making them prime candidates for five flags, particularly if their retirement incomes are a little higher.
If you are not in any of those four categories above, five flags will probably not be worth the time, effort, and money for you, though I’m sure there are perhaps a few more categories of men I’m forgetting.
How Five Flags Differs from Alpha Male 2.0
Five flags is not required for Alpha Male 2.0 status. The Alpha Male 2.0 has location independent income and a decentralized lifestyle. He is protected from most of the other possible problems beta males and Alpha 1.0s need to worry about (such as divorce, recessions, and so on). But he is not required to live abroad, do five flags, or even travel internationally if he doesn’t want to. I talked about that in more detail here.
Rather, five flags is an additional and optional level beyond Alpha 2.0. I’m doing five flags because I want to and I qualify for it, in that the time/money/effort involved is well worth it for me. But that doesn’t mean other Alpha 2.0s need to do this, or even should. Many, perhaps most Alpha 2.0s will want to do this eventually, and I think that’s great. I’m just saying it’s not required. You can build your non-monogamous, multi-business, location-independent lifestyle and then just stay right where you are in your home country for the rest of your life if you wish.
I think every man who is interested should become Alpha Male 2.0 (though only a small percentage will), but five flags is purely optional. Amazing, but optional.
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Investor
Posted at 07:32 am, 20th January 2019I would like to add that almost anyone can do 2-3 flags very easily nowadays and it has many advantages and feels way more secure than the traditional 1 flag model: citizenship country A, live in country B and maybe some investments/banking in C. This 2-3 flag model seems very good idea nowadays due to the (geo)political climate. Its very easy to set up, you just go live and work/do business in another country than your citizenship country and if you have any (to you) significant savings you put some of that in a third jurisdiction and thats it.
Caleb Jones
Posted at 10:28 am, 20th January 2019Good point.
david
Posted at 01:14 pm, 22nd January 2019I’d be interested in a training on how to convert an american business like an LLC or S-corp into a foreign business, hire myself through that business so it qualifies as foreign income, while selling the products to mostly americans.
Caleb Jones
Posted at 03:53 pm, 22nd January 2019Can’t help you with that. At least, not yet.
Alex
Posted at 04:20 am, 30th January 2019How would Five Flags work with MLTR’s?
I could see it working well with sporadic FB’s in each base/flag, and also having a live-in OLTR that travels with you. But I can’t envision it working too well with MLTR’s following the MLTR/FB model, if you’re hopping from one base to another every 182 days (or whatever).
Would you just have to accept shorter relationship lengths than you would like with these women?
Caleb Jones
Posted at 09:20 pm, 30th January 2019Depends on how often you leave your country. You can do five flags and stay in the same country 12 months a year if you like. Then it’s no problem.
But yeah, if you’re going to do what I’m going to do and move around or not, MLTRs under a frequent-travel lifestyle are difficult. No getting around that (other than to cut way back on your travel).
Chili
Posted at 05:21 pm, 3rd February 2019Have you developed some kind of system for dealing with your women area of your lifestyle under a five flags system?
My plan when I go full nomad is cultivate a roster in each country I plan to live in (without residency of course) much like you would if you were staying in one country, but with three times the effort. More work, and it may not be as effective if you are only in one country five months out of the year.
I have an OLTR, but as it is I am dangerously close to de facto monogamy. In my current particular situation I run the risk of that happening as I travel around.
How have you incorporated your current relationship system under a frequent traveler five flags system?
Nick
Posted at 09:05 pm, 5th January 2020S corps cannot have foreign owners. So your american business would need to stay a LLC. Setup a offshore corp Panama, Belize where ever. That owns the LLC. The profits from the LLC would flow through to the Offshore corp. Then you would pay yourself only from the Foreign corp. But this plan on works if you are living outside the USA 330 days a year. That would remove all Federal income tax up to $105,000 & self employment tax 15% . States my vary especially if you are CA they still want taxes on the foreign income.