Side Hustle In Paradise – NYC Millennial Balances Full-Time Job With Vacation Rental In The Dominican Republic

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view of a living room and outdoor deck

Disclaimer: The information contained in this post is provided for informational purposes only and is not intended to substitute for obtaining legal, financial or tax advice from a professional.

Recently, I bumped into a colleague at one of my clients and discovered we had more in common than just working at the same place. Like me, she had an international vacation rental business, only this time in the Dominican Republic (DR), and she’s only 27!

Of course, I had to know more about how this New York City millennial balances a full-time job with real estate. Meet Manuela Rodriguez and get inspired to set up your own side hustle in paradise:

head shot of a woman

What’s your background?

I attended Fordham University for my undergrad degree in Sociology and Psychology. I also completed my MBA at Fordham last February. I currently work as the recruiting Manager for the Gabelli School of Business. In my role, I manage recruitment across all industries for MBA/MS business students.

Why did you decide to buy in the DR? Why a vacation rental v. long-term rental?

I was born in Santiago and my whole family is from the DR. My decision was very much influenced by my desire to stay connected to the island. As most of my family members are either in the U.S or Spain, I figured that the only way to truly stay connected was owning a property. It’s a great way to maintain a relationship with a few family members and friends that currently live there. 

A long-term rental would not have made sense in Santiago, an up-and-coming destination with rising property prices. Owning a rental property served the purpose of committing to a long-term investment. It has been a little over a year, and the property value has already increased by 10%.  

view of a dining room and living room

You use Airbnb. Did you use VRBO or other sites? Do you use other marketing strategies?

I did not think to use any other sites besides Airbnb. My current marketing strategy: building a customer base with my past Airbnb guests (most of the guests plan yearly trips to visit their families and I keep in touch). I’ve had a couple of guests come back and others that have blocked dates on the calendar for the future.

How did you find the property you bought – how many trips to the DR, how did you find your rentals, did you use a realtor, how did you find your lawyer?

Whenever I visited Santiago, I would rent an Airbnb for a couple of days. I rarely stayed at my parent’s house because it just required too much planning and arrangement with my parents (maintenance/ cleaning, asking family members to stay with me for safety concerns) etc., My first experience at an Airbnb was amazing and it gave me an idea. I wanted to provide that same experience to other people, including my parents. 

In December of 2018, I stayed in an Airbnb in Santiago and experienced a small hiccup (electricity repair in the block caused a 4-hour disruption). I was in touch with the host the whole time and eventually met her in person. In one of my conversations with her, I expressed my interest to buy an apartment in Santiago. She was so friendly and super helpful and connected me to her girlfriend (who was a broker for a real estate company with multiple residential construction projects). She took me to look at a few places the next day.

By the time I had to fly back home (within a week), I involved my parent’s lawyer, provided a deposit, took out a small loan, and signed a contract. I came back in January for the closing and again in April to furnish the apartment. It took 3 trips, an extremely kind Airbnb host and her friend, my parents’ support (and their networks!! – lawyer and bank), and taking a (very calculated) leap of faith.  

My parents ended up renting out their house and opt to stay at my apartment whenever they visit the Island. 🙂 

How did you purchase the property? How long did it take you to save? Was the financing process hard? Are you happy with your rate of return?

It took me 2 years to save enough to cover half of the apartment cost and the cost to furnish it. I also borrowed a small (interest-free!) loan from my parents. The remaining amount came from a small loan I took in the DR.   

I’m very happy with the rate of return. The first year served as a test drive and It’s been very successful. The calendar has remained full since I started (9 months at the time of this interview). 

What is your long-term real estate plan? More rentals? DR or different geographies?

My long-term real estate plan is to expand the DR rentals in Santiago, other cities on the island and perhaps another country (Why not?!). It makes me excited to think about turning this small dream into something bigger. I am not afraid to explore other destinations (as I enjoy traveling and talking to people)

What do you know now that you wished you knew when you started?

As a homeowner (who went through the process of purchasing property for the first time two years ago), I thought I knew about the home-buying-process more than the average person. I also had set standards and expectations of how I wanted to run this rental property. It doesn’t always happen the way you expect it, especially if you are operating a business in another country with a different set of rules and expectations.

For example, last summer there was a huge issue city-wide with water supply. I was shocked to learn that this could even be an issue, considering that I don’t even pay for water in NYC. 

I had to develop a different set of expectations/standards and become knowledgeable (asked questions to family members, other hosts I still keep in touch) about the challenges they face and how they overcome it.

Stay informed doing your own research or via a lawyer who knows the ins-out of general business practices and property laws.   

For people thinking about buying in the DR, what advice would you give about how to get started?

Visit the island multiple times and stay at different Airbnbs. Make connections with the hosts to stay in touch and to find out about other properties. Don’t be afraid to talk to people (anyone that you come across knows somebody who knows somebody). It’s so easy to make a connection with a person especially when you’re traveling to a new place.

If you have a friend who has been to the island multiple times or who is from the DR, plan a “friendscation” to their hometown and skip the resort area. It’s a safer way to get to know the place and network with people.

What do you love most about the DR and/or owning rentals in the DR? What is the most challenging?

I absolutely love the weather, the food, and the people. I think that it’s very important to be connected to the place where you own property (or decide to own). For me, it was the emotional connection to the city where I was born and where my family is from. For you, it could be a connection to the location’s music, food or culture, and memories from an unforgettable visiting experience you had in the past. It takes passion and patience to make it happen. Besides the motivation to earn money, you need to LOVE the place and have a passion for the industry (real estate, hospitality) etc., 

The most challenging part is the remote/virtual but active role in managing your business. It did not make sense to hire an external property management company (I could not afford it) so I had to do it all on my own. I accepted a remote but “active” role in managing my investment. I have a co-host who handles the on-site logistics and a cleaning person.

I’m managing a full-time job and I’m basically running a small business at the same time. It’s so worth it and doable and it’s a smart move for any person out there who’s interested. I take any little “free” time to check-in (after I get out of work at 6pm, sometimes even later during the busy recruitment season) and during the weekends. I’m a hands-on host and I like to be part of every conversation with my guests 🙂  

view of a bedroom

How can we learn more about you?

Check out my rental on Airbnb!

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When I met Manuela, she was in the middle of her MBA, and I just knew her as one of the many students supporting the career office. Now she’s a manager in that office and is on her way to multiple streams of income with investment real estate! Her story is so accessible:

  1. Start with what you know (she’s from the DR);
  2. Work with who you know (friends, family, even the Airbnb host where she stayed);
  3. Just begin and adjust along the way (she didn’t let an unexpected water crisis discourage her).

I’m sure the current market uncertainty is hitting her bookings hard (like ours) but I checked in with her when the crisis was peaking in New York City, and she remains bullish for the long-term (as do we).

Have you built a business or side hustle around international real estate? We’d love to hear from your story!

Are you thinking about buying abroad? Let us know your questions!

two people sitting at table with dinner foodWe are Scott and Caroline, 50-somethings who spent the first 20+ years of our adult lives in New York City, working traditional careers and raising 2 kids. We left full-time work in our mid-40’s for location-independent, part-time consulting projects and real estate investing, in order to create a more flexible and travel-centric lifestyle. Read more about our journey.

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