Best combination of high quality of life, entrepreneurial freedom and low taxes

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ilpablo

Active Member
Yes, I still think (Best combination of high quality of life, entrepreneurial freedom and low taxes) summarizes the options quite nicely.

Weather is quite important to me, so that excludes Switzerland and Portugal - even though if Switzerland was tropical and had nice beaches it'd definitely be number one.

At the same time the general goal of living in a highly developed, democratic, tropical and English-speaking country is still the same. These requirements rule out most of the world and what's left is basically USA, Australia and possibly Singapore / Malaysia.

I've spent longer periods of time in Australia and really like it. However, it is too far away from friends and family to be able to commit to it for the long-term at the moment.

I plan to visit Singapore / Malaysia (hopefully soon), but I expect it won't be my kind of bread.

That leaves the US, especially Florida. All in all I think it is the best option for me, but it will take a while to get a visa. On top of that Covid cases are currently exploding over there, so I am not that keen to move at the moment anyway.

This means for now I'll stay here in the Caribbean, work on my businesses and see how everything goes.
Nice analysis, i agree with you on most of your points. I don't remember if you have family or are you planning for yourself.

In this case maybe you can consider to live somewhere half of the year (for tax saving purposes) and travel somewhere else when it's cold.

Anyway i thought about moving to Florida or California as well so many times.

The second choice probably fit me better.

But the cost of living, hard time to get visas and high taxes froze me out from making the move.

Have you considered these things?

How much will be your tax rate and cost of living there? And what's your plan to get a visa?
 

marzio

Entrepreneur
for now I'll stay here in the Caribbean
Where are you in the Caribbean? Also i forgot to add Gibraltar to the mix: 10% tax (very shortly will reach 12.5%), mediterranean weather, probably boring but you can go to Puerto Banus whenever you want.
 
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FixieHartmann

Active Member
Nice analysis, i agree with you on most of your points. I don't remember if you have family or are you planning for yourself.

In this case maybe you can consider to live somewhere half of the year (for tax saving purposes) and travel somewhere else when it's cold.

Anyway i thought about moving to Florida or California as well so many times.

The second choice probably fit me better.

But the cost of living, hard time to get visas and high taxes froze me out from making the move.

Have you considered these things?

How much will be your tax rate and cost of living there? And what's your plan to get a visa?
I am planning mostly for myself.

I actually considered doing half / half, preferable with Winter Caribbean, Summer Mediterranean but I've traveled so much in the last years that I am more looking to settle at one location at the moment.

Also, what I don't like about a 50 / 50 or even "Trifecta" setup (https://<<snippet>>.com/2017/10/11/trifecta-travel-less-tax-free-nomad/) is that (depending on the exact setup) you could be forced to travel. E.g., you actually have to move from one location to another because otherwise the tax-free status falls apart.

I don't want a setup like this. I like to travel and want to do it, but on my own terms and not because I have to. Therefore I've decided that an approach where I have a fixed home and tax residency in one place but can travel whenever I feel like suits me a lot better.

And yes, I agree, the US has a lot of downsides. Cost of living can be high, the visa situation is a complete nightmare and the tax system is very draconian and complex.

Actually on top of that there are lots more downsides to consider, e.g.:
- fucked up health insurance system
- imperial metrics
- rampant obesity
- two party political system
- taxation based on citizenship / Green Card
- gun ownership
- homelessness / poverty
.. and much more..

So, there are definitely lots of cons. Nevertheless, I think with the complex requirements that I have it still comes up on top.

Concerning tax rate and COL - I estimate to pay about 20-30% tax. Dividends and capital gains are actually quite okayish at 15-20% (Dividend Tax Rate 2021: Find Out What You'll Owe), self-employment income tax rate is about 25% at $200k. Not great, but far better than Australia and most European countries. Cost of living depends highly on where you want to live. A beachfront condo in Miami Beach will definitely not be very cheap.

Concerning visa - that is of course a tough one, as the US doesn't really have a "Tech Entrepreneur" visa. I've talked to some advisors and the closest to that is probably the O-1, however the criteria that you have to fulfill are quite specific.

Other possible routes are the diversity lottery, H-1B, potentially marriage or maybe a completely new visa that addresses international entrepreneurs that want to relocate their companies to the US.

For me I think I'll work with a company like Legalpad | US Immigration and Work Visa Technology to get as close as possible to the profile that they are looking for for the O-1 and then just give it a shot.
 

FixieHartmann

Active Member
Where are you in the Caribbean? Also i forgot to add Gibraltar to the mix: 10% tax (very shortly will reach 12.5%), mediterranean weather, probably boring but you can go to Puerto Banus whenever you want.
An island in the southern part, but I don't really want to disclose where exactly :)
 

FixieHartmann

Active Member
Where are you in the Caribbean? Also i forgot to add Gibraltar to the mix: 10% tax (very shortly will reach 12.5%), mediterranean weather, probably boring but you can go to Puerto Banus whenever you want.
I mean Gibraltar gets thrown around quite regularly over here, but it is definitely not a great fit for me:
- too cold in Winter
- shitty beaches
- no real city close by
- very boring

I've actually traveled along the entire Spanish south-eastern coastline and was not impressed. Even Marbella seemed to be quite boring if you are under 40. Malaga (besides being Spanish of course) is far too hot in Summer, too cold for me in Winter. The beaches were *very* average. So all in all that is a no for me.
 

FixieHartmann

Active Member
1200px-Saona_Island_December_2020.jpg


Unfortunately what makes my entire situation more complicated is that I am quite a beach snob ;) Like, every place that doesn't come close to the image is automatically quite "meh".. And you don't have beaches like that anywhere in Europe.
 

ilpablo

Active Member
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Unfortunately what makes my entire situation more complicated is that I am quite a beach snob ;) Like, every place that doesn't come close to the image is automatically quite "meh".. And you don't have beaches like that anywhere in Europe.
Tbh Portugal doesn't look that bad...
 

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tyrexoid

Active Member
Where are you in the Caribbean? Also i forgot to add Gibraltar to the mix: 10% tax (very shortly will reach 12.5%), mediterranean weather, probably boring but you can go to Puerto Banus whenever you want.
I hear so little about Gibraltar, need to look it up, you got me curious.
Regarding 'boring' aspect of many small islands and countries - for some reason people don't take into consideration that a flight ticket of 50-80 EUR in countries of European continent, gets you anywhere in the region - equivalent of a cost for a local bus ticket in some countries.... I find EU proximity to be a great advantage, for any of the 'boring' little countries in the region :) , I'd even grab my suitcase and go shopping in Germany or Italy for a weekend, when the COVID nonsense will calm down and things will get back to normal. So far that's the plan, despite my friends told me Montenegro is a boring village. It's kinda little and boring/chill indeed. But I like it more every day :))) this is my first summer here, pretty cool place. But really boring and lack of usual infrastructure like large retail stores (compared to US) and parking is a nightmare most of the time. But the location so close to all other European countries and 3 airports an hour drive from each other, is bad-a*s. Like a tiny retreat country, hidden in the mountains. No white sand beach, but perfect clean water all the time.
 

tyrexoid

Active Member
I mean Gibraltar gets thrown around quite regularly over here, but it is definitely not a great fit for me:
- too cold in Winter
- shitty beaches
- no real city close by
- very boring

I've actually traveled along the entire Spanish south-eastern coastline and was not impressed. Even Marbella seemed to be quite boring if you are under 40. Malaga (besides being Spanish of course) is far too hot in Summer, too cold for me in Winter. The beaches were *very* average. So all in all that is a no for me.
In your case I think the best choice is to settle in a place that has a "perfect" spring/summer/autumn conditions for your taste, and travel outside every winter into a more suitable place like Asia/Australia. Since in Australia, for example in Cairns, Brisbane, Perth, it'll be summer and also many attractions to explore. But that's costly, in case of coming from Europe. So possible combo might be Asia/Australia, or Dubai/Caribbean, Dubai/Asia. Something like that... In terms of English speaking country, that's difficult to satisfy, but so many people know average English in many countries, I would not let it restrict the list of options. Usually we socialize with expats anyway so interaction with locals is limited to some basic paperwork/stores/transportation, and it's easy to learn the basics of any language for this purpose.
 

marioIT

Active Member
Unfortunately what makes my entire situation more complicated is that I am quite a beach snob ;) Like, every place that doesn't come close to the image is automatically quite "meh".. And you don't have beaches like that anywhere in Europe.
Beach snob here too. Actual real sandy beaches and clear water snob, not artificial tourist traps with shitty fake sand and dirty water.
Yep there are beaches like that in Europe, actually imho even better. You'll find them only in the Med islands IMHO not mainland: Sardinia, Greece comes to mind as easy wins for sheer beauty.
Many of these place don't allow big/commercial buildings close to the beach, aside from the high tourism spots. They are more into natural rawness. So they may lack services.
I mean just google them, they are actually like that not photoshopped as many other mainland "tourist trap" beaches.
Caribbean and the med are different obviously, but both at the top.
Only issues of the european locations are 1) they're no year round, during winter everything is dead and cold and windy 2) high taxation 3) business aversion 4) water temp not as high as Caribbeans...
best places in europe are tax nightmares.
Mediterranean only for holidays and maybe to retire, not for living/doing business / improving your situation. ;)
 

fortunespeculator

BANNED MEMBER
I am Italian and into tech startups. He said he's into that too, so I'll give him a good advice: FORGET ITALY. Read this as do not ever put your money here.
Anything is behind the curve, from VC/advisor/government/consumers. Forget it.
You name it, justice, laws, taxes, startup costs, everything is fucked beyond repair.
Anything gov touches goes to ****. There's no way to improve.
Extreme left wing country. Constitution was written just after nazi-fascism, by the opposite, the communists... so it's like utopia: everyone should have a job, healthcare should be free, etc, but it doesn't say who's gonna pay for it... all it's made on debt, some one will pay for it.
I tell you who pays: entrepreneurs and small business owners.
But these found it, so many evaded/continue to evade... it's a catch22.
That's why taxes and startup costs are huge.

Italy is for the extremely poor (they get literally everything for free), or extremely rich. Anything in between it'll be a PITA.

Go to Miami and don't look back, even if it seems more expensive short-term. You would struggle as a tech entrepreneur in Italy.
VCs and advisors don't know **** nor they have the business experience, they just mock some trendy english words in between and that's enough here... you get funded by political sympathy smi(&%
Everyone I knew left and made it elsewhere. The one who couldn't leave, are struggling and cannot grow.
Are you n investor in Tech startups??
 

tyrexoid

Active Member
I just realized, there's a whole African continent, and especially the Northern part, in the Mediterranean, which we're not even discussing as an option. How is the beautiful shoreline of Africa is not a host to dozen of great locations like Caribbean / Greece / etc' ? that's just sad gru87¤¤
 

Barney2201

New member
Haver you looked at Mauritius. Just spent 3 months there... Beaches are Indian Ocean so excellent. Standard of living is good and with a decent income can be very high. Yes there is an element of 3rd world but seen far worse in the Caribbean. Tax can be managed to around 10% or even less if you have a business. There's one of the easiest digital nomad visas available for a 1 year stay which is renewable. I commuted every other week to UK and flights on a whole were good. Only downside is the import duty on alcohol is very high so if you like wine it's an expensive hobby!

Alternatively, if you like to ski take a look at Andorra, I've just come back from there and was very impressed. It's obviously a very wealthy country, bit like Monaco but with space, reasonable prices and less Russians... Fibre to every property and lots of inward investment. Might be worth a look...
 

FixieHartmann

Active Member
Haver you looked at Mauritius. Just spent 3 months there... Beaches are Indian Ocean so excellent. Standard of living is good and with a decent income can be very high. Yes there is an element of 3rd world but seen far worse in the Caribbean. Tax can be managed to around 10% or even less if you have a business. There's one of the easiest digital nomad visas available for a 1 year stay which is renewable. I commuted every other week to UK and flights on a whole were good. Only downside is the import duty on alcohol is very high so if you like wine it's an expensive hobby!

Alternatively, if you like to ski take a look at Andorra, I've just come back from there and was very impressed. It's obviously a very wealthy country, bit like Monaco but with space, reasonable prices and less Russians... Fibre to every property and lots of inward investment. Might be worth a look...
I just checked, UK <-> Mauritius is 11:30h flight time and you did that every other week? Crazy..

Yes I looked into Mauritius but have the feeling that it would be too small, not enough going on and too 3rd world for me. But I might be wrong.
 

void

Entrepreneur
I just checked, UK <-> Mauritius is 11:30h flight time and you did that every other week? Crazy..

Yes I looked into Mauritius but have the feeling that it would be too small, not enough going on and too 3rd world for me. But I might be wrong.
it's usually much shorter because of EU customer protection and penalties for delayed flights :)
also the vast majority of flights is over night (it's about crossing the equator, not an Atlantic ocean...) so you sleep through most of it and land relatively rested
 

freedomseeker

New member
it's usually much shorter because of EU customer protection and penalties for delayed flights :)
also the vast majority of flights is over night (it's about crossing the equator, not an Atlantic ocean...) so you sleep through most of it and land relatively rested
That is a good point about flying up and down as opposed east west... lest time change jet lag.
 

void

Entrepreneur
That is a good point about flying up and down as opposed east west... lest time change jet lag.
it's a big advantage practically speaking - I rather take 11h overnight flight than 6 hours during the day...
it's sad that there's not much south from Europe - Reunion, Mauritius, ... Madagascar for the fearless...
 

Barney2201

New member
I just checked, UK <-> Mauritius is 11:30h flight time and you did that every other week? Crazy..

Yes I looked into Mauritius but have the feeling that it would be too small, not enough going on and too 3rd world for me. But I might be wrong.
Yes, I did the Mauritius commute nearly every week and it wasn't too bad as long as you can afford the cost of business class. I would regularly spend Sunday on the beach, driver picks you up at 7pm, jump on the 9pm to LGW, couple of drinks and go to sleep, wake up in LGW at 0600 and go to work. Only kicker is BA is running poverty business class (otherwise known as the dormitory) not the new suites. I would then work until Thursday, then bounce into Europe to start my overnight trip back to Mauritius (exiting Europe massively reduced the cost of the trip) landing in the morning in Mauritius. All very doable, only downside was running a UK business day from Mauritius and having a family there. Wake up at 0630 but don't start work until lunchtime and finish around 10pm, this was the hardest bit and ended up being the deal breaker....
 

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