Where should you start/move your tech/crypto startup?

I recently asked myself this question and I still haven't answered it completely, but I will share with you what I have found so far. 

We have incorporated our company in Delaware. I live in California but I am definitely NOT staying here.

Why I am leaving California

Really it's for personal reasons. I never wanted to live in California, granted San Diego has been a nice place to be stuck for the past 18 years as I raised my son but it was never a place that I aspired to live.

I am Canadian and I don't have the same "America is the best" mentality that most Americans have. However, I have definitely been tainted, my Grandchildren will be American.

Now that my son is 19 and a grown human, I can go and retire where I have always wanted, the Caribbean. Not that I am going to retire in the next 15 years, but I am working on my exit plan. So why can't my startup contribute to that exit plan? It most definitely can!

Now that covid has pushed remote work forward dramatically, we can work anywhere.

My co-founder is in Toronto, Canada and will be leading our partner & support teams from there. So I have to choose where I will lead the development team.

California's taxes are out of control and only likely to get worse before they get better. When you have so many other options open to you, it's worth it to have a look elsewhere.

San Francisco and Los Angeles have rampant homelessness with no end in sight. A lot of upwardly mobile individuals realize that they can't change things and are just leaving instead.

What I am moving towards

There are a few requirements that are high on my list when considering moving.


Carribean water
A good startup environment with access to capital
Stable economic and cultural environment
Less taxes than California
Crypto friendly
High Speed Internet
Either a highrise view or a house with a boat dock
Good for my "American" family

Here is my short list of three possibilities

They are conveniently ordered in both distance and tax advantageous.


Is the least dramatic move.


Not entirely Carribean but it's close to the Bahamas


Mayor Francis Suarez is very startup friendly and there is a culture of innovation starting to happen.

Economic & Cultural

Miami being on the mainland of America is very economically stable.

You could argue that Miami is far more culturally diverse than San Diego.


Florida does not have any State taxes but you will still have to pay Federal Tax.

President Biden is trying to raise 700B in revenue so he is stepping up is scrutiny of Americans by doubling the IRS workforce and hiring an additional 87K employees.

Seeking Alpha says that in 2023 crypto transfers of over 10K will have to be reported just like cash. - so why not be in a location that is crypto friendly like Puerto Rico? You will still have to report, but you won't have to pay cap gains.


Mayor Suarez was able to attract the Bitcoin conference to Miami this year. Although he is making great strides, the crypto community does not have as much as a stronghold as Puerto Rico, where they even have a term for people who are into crypto, the "crypto bros".


Miami is full of both high rises and homes on canals.



Miami is easy to get to and it's known to be fun for a vacation.

Puerto Rico

I recently went there in January and fell in love with the Islands and the people. I would have to say it is both the scariest and most exciting option.


Definitely Caribbean. Close to Bahamas, BVI and other Caribbean nations. Ideal for cruising.

Economic & Cultural

Puerto Rico has lower cost but highly skilled workers. You can feel good about hiring people in Puerto Rico because it's almost like off-shoring, but you are still hiring Americans. Which feels good. Additionally you will be helping Puerto Ricans to rebuild their economy. In exchange they are happy to help you lighten your tax burden in return.  They have a saying in Puerto Rico, #workhardplaytropical. They definitely like to play and you will have to get used to "Island Time". 

Although the main language is Spanish, almost every person I spoke with knows English as well. You may have to watch out for "Gringo Pricing".

Old San Juan is full of culture but so is the rest of the Island.

There are some places in Puerto Rico that are decidedly sketchy. However, if you stay out of those areas, you are pretty safe.

For the most part, Puerto Ricans are good people.


There is a healthy tech startup scene in Puerto Rico. One of the biggest accelerators in Puerto Rico is in Santurce, San Juan, P18.

There are several English speaking entrepreneurial meetup groups all over the island.


Act 60 gives both businesses and individuals significant tax breaks, but it's not totally tax free. You could think of it as Tax Haven lite. 

There is a HIGH likelihood of being audited under Act 60 so if you plan on moving to Puerto Rico, make sure you are following ALL of the rules of residency.

Chapter 2 Individuals

As an individual investor, there are no US or Puerto Rican taxes on capital gains.

Chapter 2 requires a one time fee of $ 5000 and a annual fee of 10,000 that must go to approved charities

Individuals must also purchase a property for their residence within 2 years.

No tax on interest and dividends on Puerto Rico sourced income.

Chapter 3 Businesses & Business Owners

Interestingly Puerto Rico is the only place on earth where global taxation is invalid. Instead, you will pay Puerto Rico taxes.

Businesses that move their operations to Puerto Rico can reduce their corporate taxes to 4%

They are also exempt from property taxes, municipal taxes, and taxes on dividend distributions for income generated and property used in exempt operations.

The real draw for business owners is that, distributions from earnings and profits is not subject to Puerto Rican income tax. However, they do have to pay themselves a "reasonable" income. 


There is a very well established crypto community. In Santurce in San Juan, there are "Crypto Mondays" where all of the people in crypto gather.


Of the 3 options, Puerto Rico's power grid is the most unstable, which does affect the internet. Most people have both broadband and a cellular backup.

Starlink is said to be available soon so that may mitigate that issue. 


There are 4 areas that sovereign individuals congregate in. Palmas Del Mar is a gated community on the eastern side of the island. It reminds me a lot of Del Mar, in San Diego. Very idyllic. Perfect for young families and retirees.

Dorado, seems to be where most of the tech progressives are. It is very convenient to San Juan, only about 20-30 minutes away.

Rincon is like old california and where most of the surfers hang out on the western side of the island.

Bahia Beach would be similar to the Cayman Islands, VERY high end and secluded.


Everyone I have spoken with wants to come to Puerto Rico for a holiday. Even my co-founder looks forward to business meetings there. It's a quick 2 hour flight to Miami. 

From a health care perspective it is pretty good too. Triple S is BlueCross Blue Shield and it is decently priced compared to the mainland. Watch this video https://youtu.be/bW6UWyuDAYk

Additionally there are two new hospitals being built right outside the most popular areas for ACT 60 people. Dorado and Palmas Del Mar.

Cayman Islands

I was in the Cayman Islands with my son the year after my Mother died. For the first time in a very long time, I felt safe and at home.

You will have to jump through a lot more hoops to move the Cayman Islands. You will need health certificates and background checks. Interestingly it is a path to UK citizenship if you want it and can prove that you are a decent human being. 


The water is definitely Carribean blue, although not as well suited to cruising as Puerto Rico. There are a lot of evening and weekend cruises. 

Economic & Cultural

Grand Cayman is very business friendly with friendly people. It is a VERY safe country to be in, there are no guns and very little violence. People work hard and they play or work out after work. I would say the work life balance is the best there.

If you want the best that money can buy, you can find it here. You will do well to conduct yourself with respect and dignity in the Cayman Islands. 


One thing to note is that part of the culture is to not talk about how much money people have or how they got it or what they do with it.


Grand Cayman is recruiting heavily through their Tech City Program, however, the investment community has not yet developed. If you are not a bootstrapped or crypto funded company, it may be difficult.


If you are not American, the Cayman Islands can be really attractive due to the fact that they are a tax free nation. However, if you are American, it comes with a fair amount of "bad energy" from them as Americans don't like competition. America have used the media to really hammer the Cayman Islands and a good percentage of Americans believe all people who live there are "hiding money". There are a lot of non-Americans who are not hiding money because there is no need to hide it.  What most American's fail to understand is that only America and Eritrea in Africa tax their citizen's and their companies globally. I find this odd because America was founded because they wanted to get away from the British tax system

It's hard to believe but the UK has a better global tax system.

For instance, if Richard Branson wants to live in the British Virgin Islands, he doesn't have to pay personal income taxes. The same goes for Raoul Pal who lives in the Cayman Islands. If they were American they would have to pay taxes.

So if you are American, and you live in the Cayman Islands, you will have to pay taxes on anything over about 100K unless you are willing to give up your American Citizenship. 

Expatriating will also trigger the biggest taxable event, the exit tax.

Americans are going so far as to encourage other countries to do global taxation so they can justify their own aggressive taxes.


There is a growing group of crypto people in the Cayman Islands. 


There is a lot to be said about the infrastructure in the Cayman Islands. It is the most stable of all of the Caribbean islands and they even have co-located key banking data over on Little Cayman. It may not be the fastest but it is VERY reliable.


There are lots of highrises on 7 mile beach and plenty of homes on canals.


This one is a tricky one, it's very small. People will come for vacation but won't want to stay longer. If you have no family and no dogs this will be an easier option.

Dogs must be rabies vaccinated with health certificates. It's harder to come and go with them.

From a health care perspective they have Health City which is purportedly attracting US health tourists. Watch this video https://youtu.be/BjQCCgyhmU8

In closing

I still haven't figured out which of the three is ideal for me and my family. I have yet to visit Miami so I guess that is next on my agenda.