Puerto Rico’s Rental Goldmine: How Roberto Green Found Massive Success in Short-Term Rentals

Roberto Green (00:00)
a lot of people don’t know about investing in Puerto Rico. They see it as a foreign country. A lot of people ask me, you know, what’s the currency? And the currency is the U.S. dollars. It’s a U.S. territory. So there’s a lot of opportunity, but obviously not a lot of people know how to invest. Plus, there’s maybe a language barrier. Some people think that they need to speak Spanish. Yes, it’s a benefit. And that’s my unfair advantage that I can speak Spanish and English and I can communicate effectively with locals and investors.

Cody Crabb (00:18)
Mmm.

Roberto Green (00:29)
but it’s really knowing your way around. It’s just like any market,

Cody Crabb (02:04)
Welcome back to the Real Estate Pros podcast. I’m Cody Crabb with Investor Fuel. Today we’ve got Roberto Green with us, owner of RGJ Enterprises out in Puerto Rico. He’s been investing ⁓ across flips and wholesale and now really dialing in on scaling short-term rentals in the Puerto Rican market. Roberto, thanks so much for joining us today.

Roberto Green (02:08)
Thank

Thank

Now Cody, thank you for having me. Appreciate it.

Cody Crabb (02:26)
Of course. You know, I don’t know if I’ve ever had a guest that has been involved in the Puerto Rican market. So this will be pretty interesting. ⁓ So ⁓ let’s just kind of start here. Take me back a little bit. know, ⁓ how did you get involved in real estate? ⁓ know, what did the path to real estate look like for you?

Roberto Green (02:47)
man, it’s definitely been long. It’s been over seven years that I’ve been investing in real estate. I really started around COVID when COVID happened. I was in the restaurant industry doing really well, but then COVID happened, the restaurant business took a hit. So I was looking to transition and to find new opportunities. So I ended up learning more about fixing and flipping in Massachusetts where I was born and raised. And Boston is a different market, very expensive.

but I still got into the fix and flip market there. I did really well in the beginning, but then it got tighter and tighter. The deals started getting more difficult to find. So I started transitioning into wholesaling. I started buying and holding Midwest. So at one point I had 12 properties in Ohio doing the Section 8 rental method, but the cashflow really wasn’t there for me personally. And really that’s

what I felt like I wanted to get into real estate for. A lot of people talk about they want financial freedom, financial dependence. But to me, it sounds cool. But what do the actual numbers look like? And what does the cash flow would actually goes into your pocket? It sounds cool to say I own 12 properties. But if those 12 properties aren’t bringing me cash flow, what good does it do to have all these properties? So what’s the point? So

Cody Crabb (04:11)
Yeah, what’s the point?

Roberto Green (04:15)
When I advise people, because I’m also a fix and flip mentor and a short term rental advisor, is really start with the end in mind, right? What do you want to get out of real estate? Tax incentives? Do you want to get cash flow? Are you looking for the long term equity play? Start with that. I really wanted cash flow. And that’s why I started transitioning into Puerto Rico when I started learning more about the short term rental market out here.

Cody Crabb (05:31)
Gotcha. So did

you have a connection to Puerto Rico first or was this just like a, I’m heading over there.

Roberto Green (05:36)
Great question. So I am actually Puerto Rican. My father was born and raised in Puerto Rico and my mother was actually raised here from Guatemala and raised in Puerto Rico. I came to Puerto Rico just to see family. I never looked at it to invest. ⁓ But really I started focusing more from the real estate aspect, different strategies. And I started learning from different masterminds that you can do long-term rentals, you can do midterm rentals, you can do short-term rentals, you can do…

Section 8, there’s so many different ways that you can make money with real estate. But at end of the day, what I cared about was cash flow. So when I started running numbers, I started seeing, OK, if I do short term rentals strategically in Puerto Rico, there is opportunity for me to generate good cash flow, which I’m generating now, which is why I sold all my properties in Ohio, basically started from zero again, and then re-strategized into Puerto Rico.

Cody Crabb (06:33)
Wow, okay, so tell us a little bit about the market in Puerto Rico. How is it different than, what challenges do you see and what benefits are there? Because like I said, I don’t know if I’ve ever heard from anyone on this podcast that’s been in that market, so I’m kind of curious, especially as someone that’s kind of been in both sides of it. I’d love to know what differences have you seen?

Roberto Green (06:56)
Yeah, so I mean, when it comes to the numbers, ⁓ you can definitely find more affordable properties here in certain areas in Puerto Rico. The thing that a lot of people don’t realize is that if you’re a U.S. citizen, you can actually apply for bank loans on the island. If you decide to move to Puerto Rico, you can get an FHA. If you want to get a vacation home, you can get a second home loan, which would be 5 % percent down.

And if you want to buy an investment home, an investment opportunity, you can buy conventional at about 20 % down payment. So because it’s a US territory, it does qualify for bank loans if you’re a US citizen, not just for the Puerto Ricans, but obviously for the United States, individuals in the United States on the mainland. So that’s pretty, pretty awesome fact. You don’t need a passport to come here. You can have, you can come with just a license.

As far as price points, you can find properties from a hundred grand to a million dollars plus. So there’s different markets in different areas. What I love here and what I’m focusing on are properties within the $350,000 to $500,000 range because these properties, I find that you can actually do short-term rentals. And the way I do them is I look for properties that have at least four to five bedrooms so that I can fit eight to 10 guests.

I like to be within like a 30 minute driving distance from the airport. So it’s not in an oversaturated market. Like most people invest into certain metro areas. I like to invest a little bit more in the rural areas, which have their pros and cons, which we can talk about. But with that strategy, I’m generating anywhere between 10 to $15,000 a month in gross revenues. And because I’m self-managing, I’m seeing about 50 to 60 % cash on,

cash returns as far as cash flow goes. So it’s a really lucrative ⁓ investment for me. And it’s been helping me transition and get into more properties and I’m really just scaling, working with other investors that want to either partner up or hire me for the consulting services and I can help them recreate what I’m doing. So I’ve been able to scale what I’m doing now on the island.

Cody Crabb (08:50)
Hmm.

Yeah, so ⁓ just to kind of get a snapshot of the kind of deals that you look for, what’s something that you look for in the properties that you ⁓ want to acquire and then what is maybe something that you’re like huge red flag and not doing that that sounds kind of like a normal thing to.

Roberto Green (09:33)
Yeah,

great question. So the first question is what I look for. So when you’re investing in a short term rent, so I’m not just looking for any regular property, right? I’m looking for a property that has or can offer an experience.

What I mean by experience is that it at least has a pool. And in Puerto Rico, there’s the geography of Puerto Rico, there’s a lot of mountainous areas. So I look for properties that have a view.

right, because it’s an experience for somebody coming from, let’s say, New York, Florida, California, to come see all the mountains, the rainforest, and they’re actually inside of it, right? So it’s a huge experience. I look for properties that have at least four to five bedrooms so that they can comfortably fit at least eight to 10 guests or more. I look for properties that are within a 30-minute driving distance from the airport so they’re not too far away from the metro areas.

And ideally, I look for properties that are under $500,000. Because then I know that I can charge at least anywhere between $350,000 to $500,000 plus per night. With that formula, that’s where I’m able to generate $10,000 plus a month. Because Puerto Rico, the benefit of it is that it’s the seasonality of it. It’s basically summer year round. So from January to December, it’s warm weather.

Cody Crabb (11:29)
Mmm.

Roberto Green (11:32)
with the exception of September, October, November, which you can have hurricane or rainy season. But even still, I’m generating six to $7,000 in those months. So to answer the next question, which was really the challenges or what I stay away from as red flags, is unlike the United States, we look for cement built properties, not wooden properties. The reason being is because the wooden properties on the island are not bankable.

Cody Crabb (11:56)
Hmm.

Roberto Green (12:00)
You cannot get a bank loan on any wooden structure. has to be concrete cement. And I make sure that they abide by the inspections that the banks require so that we can actually get a loan on these types of properties. There’s a walkthrough checklist that I typically offer my students. So obviously, what to look out for. What are the high-cost ticket items to be aware of?

so that they can make an educated decision and they’re not spending too much on the repairs and rehab of the property.

Cody Crabb (12:32)
Yeah, wow, those are some great tips and I never would have, I did not know that about the concrete housing, that’s interesting. I know that a lot in Mexico and South America they use a lot of the concrete houses and so I wonder how that works down there, I don’t know. We’re not gonna get into that. But basically, I think it’s important to know, that’s a wildly specific thing that does not happen outside of Puerto Rico. So perfect example of know your market, because if you don’t, like,

How is that gonna work? very great information there. ⁓ So as far as ⁓ your ⁓ short-term rentals, I want just to talk about short-term rentals for a minute. ⁓ A lot of people see the higher amounts they can charge per night. They see that they can, you know, they don’t have long-term tenants and they kind of are like, it’s a dream, it’s a perfect situation. ⁓ What would you tell those people because…

Roberto Green (13:21)
Thank you.

Cody Crabb (13:29)
I think a lot of people that have long-term rentals see the higher amounts and people that stay for less time and they’re a little bit like, what’s the downside? Like, why am I not doing that? So what would you say to the people that kind of are like, it’s the dream, right?

Roberto Green (13:44)
as far as the dream being.

Cody Crabb (13:48)
Like why doesn’t everybody do this? Like what challenges are there even? Because it sounds like a perfect situation.

Roberto Green (13:53)
Yeah, no, mean,

a lot of people don’t know about investing in Puerto Rico. They see it as a foreign country. A lot of people ask me, you know, what’s the currency? And the currency is the U.S. dollars. It’s a U.S. territory. So there’s a lot of opportunity, but obviously not a lot of people know how to invest. Plus, there’s maybe a language barrier. Some people think that they need to speak Spanish. Yes, it’s a benefit. And that’s my unfair advantage that I can speak Spanish and English and I can communicate effectively with locals and investors.

Cody Crabb (14:12)
Mmm.

Roberto Green (14:23)
but it’s really knowing your way around. It’s just like any market,

but it’s more of a bureaucracy where you have to know the right people, have the right connections in order for you to not struggle as much. And that’s really where I come in as an advocate or as a liaison and as an advisor, a trusted advisor at that, right? Because I’ve gone through the trials and tribulations.

I’ve done this by myself, which is why I documented my journey.

because I saw how struggles some it can be if you don’t know what you’re doing. And that’s really why I created my course and my program to educate people on how to properly invest into Puerto Rico, especially Puerto Ricans that had to leave the island years ago that are looking to come back, but they’re having bad experiences or don’t understand how to invest back into the islands. And really my job is to educate, obviously everybody, but especially the Puerto Ricans that want to come back.

but don’t know how because there’s a lot of great opportunities here. And who doesn’t want to live on a beautiful island with beautiful views, you know? It’s amazing. And it’s, I think there’s a better work-life balance. I really love the culture overall. People are very friendly, despite what the news may showcase, but people are very friendly, very polite, educated. The culture here makes you feel welcomed and at home. And there’s a lot of people either moving back

Cody Crabb (16:02)
Yeah.

Yeah, it’s gorgeous.

Roberto Green (16:29)
home to the island or a lot of people from the mainland just exploring new opportunities because as you guys see in the United States, it’s been very difficult to get cash flow and to even invest and everything’s been inflated. ⁓ Prices have increased dramatically. And in my opinion, it’s getting harder and harder to invest in real estate in the mainland where the numbers really don’t add up.

Cody Crabb (16:41)
Yeah.

Yeah. So, okay, so

I’d love to ask that same question about like the, you know, what are the challenges about short-term rentals specifically? I think, I think same thing, same kind of thing. A lot of people see, you know, long-term versus short-term and they see, they see a lot of that and they see so many benefits of short-term. Like what would you say to those people that think short-term is the solution? Just let’s just all do short-term.

Roberto Green (17:19)
Well, short term, don’t think is the solution. think short term is more of a strategy, right? It’s not a lot of people know what they’re doing when it comes to real estate, right? They see something on Instagram, they hear about short term rentals. I’ve heard both where short term rentals is dead and nobody wants to invest because it’s oversaturated. Then you have long term rental, section eight, midterm, ⁓ co-living. There’s so many different things that, you know,

different strategies to invest. What people need to understand is one, you need to get educated on the actual strategy that you want. And I typically start with the end goal in mind. What do you want to invest in real estate for? If it’s for cash flow, then I personally feel like for cash flow, you’re looking at co-living, while you’re looking at strategic short-term rental investing. Because you can get the most out of a single property, you’re maximizing the revenue.

higher risk, higher reward, where people fail is that they forget that short-term rental isn’t just buying a regular home and then listing it as a short-term rental. That’s what’s been happening these past couple years. And that’s where the over-saturation has happened, where just basic mom and pop, regular, anybody that wants to buy a property and has capital buys it, does a little decoration and puts it on the short, put it.

puts it on Airbnb and they call it a short-term rental. It’s not the business. That’s why they’re failing. And that’s why they’re leaving. So when I listen to people who give advice, I listen to what they do wrong. And a lot of people, what they do wrong is they don’t come in with a strategy. They want to invest in Puerto Rico, cool. Well, what’s your strategy? Or they’re like, just send me a deal. What does a deal look like for you? They can’t even answer that question. So to me, they shouldn’t even be investing in real estate.

they need to focus on the education because there’s this whole facade and this whole image in social media that, you know, real estate is this amazing financial freedom tool that you can get into. And then they want to sell you a course and that’s really where they make their money. Now, I do the same, don’t get me wrong, I obviously have a course, but I’m actually telling you like, hey, this is what you can potentially earn here. These are the numbers, this is what I’ve proven. If it works for you, then obviously let’s move forward together. But I’m not here

Cody Crabb (19:28)
Yeah.

Yeah, as

I always say, you’re at least doing it. I’m always like, why are these people that are making a course, why aren’t you doing the thing that you say will make you rich only? Why aren’t you just doing that? But in your case, it seems like you’re kind of spreading the word a little bit about this kind of neat opportunity that you’ve found.

Roberto Green (19:56)
Yeah, yeah.

Yeah, I was really hesitant on talking or creating a course, but it’s needed, right? And I do it because I’m confident in my product. It works. I’ve done it. I’ve replicated with partners and have people flying from the States meeting me in person to actually physically come here see which I don’t mind doing because I’m very transparent. But you have to do it the right way, right? And the right way is you’re not buying a home. You’re buying a business.

And if you don’t treat it as a business, you’re not going to succeed. You need to have systems, need to have processes, you need to have procedures in place. You need to understand the market. You need to understand the numbers. You need to understand the risk involved because obviously there’s no full 100 % risk free investment. ⁓ But that’s where the risk reward ratio comes in. My job is to mitigate the risk as much as possible because I come from a financial background working for Stakesview Bank and JP Morgan.

I have an understanding of risk management. to me, it’s really just being strategic, being conservative with the numbers and negotiating prices at all times and not overpaying. Because any deal, whether you’re fixing and flipping, doing long term, short term rental, mid term rental, the deal is always going to be in the purchase price. You can do any strategy, but if you bought it at a too high price point, it doesn’t matter what strategy you’re going to implement.

you overpaid for the property. So the mortgage or the debt service that you’re to have to pay is going to outweigh the potential cash flow or the earnings that you’re going to bring in. And that’s why I feel like now the way things are in the States, everything’s overinflated, overpriced. And I don’t think things are worth what they say they are, especially with the Zillow estimates, because I’m a wholesaler as well. People are going based off

Cody Crabb (21:35)
Yeah.

Roberto Green (21:52)
Zillow estimates and they’re probably one of the worst estimates that I’ve ever seen and I’m going to call them out because I think they’re also ruining the market and people need to wake up, sellers need to realize that they’re not sitting on gold and people are not willing to pay $700,000, $800,000 for a home that needs $100,000 in repair and zero equity. That’s not real estate investing. That’s setting yourself up for failure.

Cody Crabb (22:15)
Yeah, yeah, that is very true. I’ve heard definitely a little bit of venom against Zillow on this podcast for various reasons. ⁓ So if someone wants to work with you, ⁓ who should they be, what should their goals be, and how can they get in touch with you?

Roberto Green (22:33)
So the ideal person that I work with with my model is individuals that are bankable, meaning they have good credit, good credit being over $650. They have W-2 or tax returns for the past two years so that they are bankable. They can get a second home loan or they can get a conventional loan with a bank here that I will connect them with personally to get a pre-approval. And that they need to at least have $100,000 in liquidity.

I want to be realistic. I’m not here to tell you that you can, you know, get this, do this and with zero money, zero experience, like, no, you got to have some capital. I’m willing to work with you, but that’s the minimum requirement for me to work with me with my strategy. If you’re looking to make at least eight to 10 grand plus a month with the strategy that I’m doing, because you do need some capital for the down payment, my services, as well as

the furnishing and design, because a lot of people forget that you’re not just putting furniture in the home. There’s also like landscaping, you need to have a pool, needs to be a beautiful property that looks like a mini resort per se, that people want to leave their home in Boston, New York, Connecticut, Florida, and come out to Puerto Rico and be like, my God, there’s a volleyball court, there’s a basketball court, there’s a pool.

Cody Crabb (23:55)
You

make a really good point that I hadn’t even thought of, is if you’re not gonna stay at a resort or a hotel, you’re gonna go stay at just some house, you do kind of expect it to be a vacation place. So you’re right, I think that’s something important to think of as well. And that’s exactly the kind of thing where having somebody who knows the market really well and can kind of guide you is just gonna make all the difference there. ⁓ So thank you so much for that. If people wanna connect with you online,

⁓ How can they do that? How should they reach out to you?

Roberto Green (24:28)
Yeah, of course. So my Instagram is really where I connect with most people. They’ll, if they follow me @RobertoGreenJr. R-O-B-E-R-T-O-G-R-E-E-N-J-R. They’ll be able to follow me on Instagram and automatically they’re going to receive an email with a request to have a conversation with me. I love to have strategy calls with people. So we set up a free one-on-one 30 minute call.

And we talk about their goals, we talk about their finances and see if we’re going to be a good fit to work with one another if we are. And I typically move forward with them right away. But at the very least, I provide them free access to my school classroom, which I can give them access to because they’re part of your listening crew. And I’m more than happy to give them the free access to the course that I have.

so that they can at least start learning about Puerto Rico, feel more comfortable and reach out to me if they have any questions or concerns.

Cody Crabb (25:26)
Absolutely, yeah, if you could go ahead and shoot us a link to that we’ll put a link in the comments or not in the

comments But in the or do you have a code or something? How would you like us to do that?

Roberto Green (25:35)
Yeah, so I’ll send you the link. It’s really skool.com/PuertoRicoShortTermRentals9194 (www.skool.com/puerto-rico-short-term-rentals-9194), but it’s a little long, we’ll put that in the comments. But Roberto Green Jr. is really my Instagram. They’ll get all the DMs so they can connect with me and they can book a strategy call with me. So I’m more than happy to connect and serve.

Cody Crabb (25:42)
Awesome.

Yeah, we’ll put that in the comments there. We’ll totally do that.

Awesome, awesome. Thank you so much. I really appreciate all this. It’s been really interesting to learn about Puerto Rico. I did not know that there was so much opportunity there. ⁓ So I’ll definitely be looking into that.

Thank you so much for talking to us today, Roberto, and thank you for all you listeners out there that joined us today. If you like what you heard, go ahead and give us a like, a subscribe, all the things, and make sure to follow us so that you don’t miss more awesome conversations with people like Roberto. Thank you so much one more time for joining us, and we’ll catch you next time.