One Year In

We’ve been living in Puerto Rico for a bit over a year now. Why did we do it and how is it working out?

Initally we were interested because of the potential tax savings. If you live off of investments, then you can avoid paying capital gains tax on your investments if you live in Puerto Rico. Tech entrepreneurs make their money by creating companies and selling the stock in those companies. If you have a big win, then you also have a big tax bill. It’s attractive to think about having another big exit and not having to pay taxes on it.

That being said, we started exploring the idea of moving to Puerto Rico and we found that we love the island and the people here. We came for the tax breaks and we stayed for the people.

We’ve made a ton of new friends

Puerto Rico is a friendly place. Part of it is the culture and part of it is a result of meeting like minded people. Yes, compared to The States Puerto Rico has a lot of issues. There’s the government debt. There are infrastructure issues. Crime and beggars can be an issue. More on that later, but let’s talk about the people first.

Loving the locals

We’ve made a bunch of local friends. We’ve found that Puerto Ricans are super friendly. When you first arrive you mainly deal with service industry people like taxi drivers, hotel clerks, and waiters and waitresses. The taxis aren’t so great, but the rest of the folks seemed very open to giving us advice and answering our questions. What worked for us was to get involved in things we already liked to do, and we met folks through those activities.


There is a huge tennis center at Palmas Del Mar about 45 minutes from San Juan.
We started there and met some of our first and best friends in Puerto Rico. Palmas is a great place to live if you want to keep a boat nearby or even in back of your house. The Palmas Athletic Club includes the tennis center, which is largest in the Caribbean.

In San Juan there are lots of great places to play tennis too. Here are a few other favorites. The Isla Verde Tennis club is just a few miles from the airport. Ocean Park has great courts right next to the beach. There is also San Francisco Tennis Club and Baldrich Tennis Club in Hato Rey.

Tech Startups

I’m a tech entrepreneur so went in search of co-working spaces and found Piloto 151 in Old San Juan. It’s a great place to hangout and they have regular activities for learning and networking. They were running a Founder’s Institute program when I arrived and I ended up getting involved in that as a mentor.

I was very lucky that Parallel 18 was just starting when I moved here. This is an accellerator program that is nurturing a tech startup ecosystem here in Puerto Rico. They help startups from Puerto Rico and all over the world take the next step in building their busineses. I’ve been a mentor for the first two cohorts and found it a to be a very exciting program and a great place to meet like minded people.


We also found had a lot of activities where we could meet new people. For Puerto Rico tech folks, the San Juan Tech Meetup is a great one to attend.

The Nuvo Ricans

In order to help stimulate the economy, Puerto Rico passed some interesting tax laws to incentivize

Addressing the negatives

Sure, Puerto Rico has it’s issues, but in our experience they haven’t been showstoppers and they add to some of the flavor of the island.

Isn’t the island bankrupt?

There is a financial crisis for sure. But frankly I don’t see the issues day to day. They still repair the streets. (Yes, there are still a lot of huge potholes. But drive around South of Market in San Francisco and it’s worse I think.) I’m often amazed to see street cleaners walking around sweeping and cleaning up the town. This seems to be going on even on holidays and weekends.

Construction seems to be going on. Restaurants are constantly opening. Buildings are being built. Plaza Las Americas, the largest mall in the carribbean, is constantly busy and finding a parking space is often a challenge. The government may be out of cash, but the economy is still vibrant.

Yes, there is some strife over PROMESA. Congress has stepped in to restructure the debt and put in an oversight board. They did the same to New York City in the 1970s and Washington DC in the 1990s.

Anyway, the government needs to figure out how to get things back on track. But it doesn’t effect daily life except for the occasional protest.

Doesn’t the electricty and water go out all the time?

We’ve seen it go out a few times. Most buildings have generators. The super modern buildings can run for days without power. The older bulidings have a generator that runs the elevator and maybe one outlet per apartment for the fridge. We don’t have snow days but there have been days when school was cancelled because of power issues. The good news is if the power is out, you can go sit on the beach under a palm tree. You can drive to the other side of the island and stay in a hotel. It’s not more of an issue than earthquakes or epic storms that you see in other places.

Do you feel safe?

There are parts of San Francisco California where I don’t feel safe. There are parts of San Juan Puerto Rico that I don’t feel safe. But generally the places where you would want to live are safe. Puerto Rico’s economy is tourism based and they do spend funds on policing and keeping things safe. It is strange that because it’s a small island, you do have very fancy places near government housing. Some people opt to live in gated communities and that’s an option. We have lots of friends that don’t live in gated communities.

There are beggars on the streets in certain places. It’s nothing compared to San Francisco though. I do choose certain routes when driving to minimize the intersections with beggars.