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Real Estate Pros · April 3, 2026 · 16 min listen

Is Puerto Rico the Safest Caribbean Investment?Why Hospitality Demand Keeps Rising

Show summary

In this episode, Marc Weisi of YieldWink shares his journey from Wall Street to real estate investing, with a focus on hospitality in Puerto Rico. He discusses strategies for optimizing investor returns, managing operations, and capitalizing on opportunities in the Caribbean market.

Key takeaways

  • Puerto Rico hospitality has grown every year for the last five years, including through COVID, as more American travelers consider it over the Dominican Republic or Jamaica.
  • Marc's base is San Juan, home to the busiest airport in the Caribbean, which handles about 90% of the island's passenger traffic, driving guest demand for his properties.
  • His hospitality business runs on an average stay of about 2.5 days, with roughly 50% of guests coming from the US and the rest from the island, other Caribbean islands, South America, and Europe.
  • He treats guest feedback (reviews and staff conversations with guests) as his key non-deal metric for business health, more than other quantifiable metrics.
  • He built local partnerships with small and medium-sized businesses (tours, excursions, breweries, an art tour) to refer guests to, creating a win-win that strengthens the local community and guest experience.
  • His background combines financial underwriting on projects with hands-on asset management/operations once construction is complete, which he says hospitality demands more than other real estate types due to high guest turnover.
  • His current growth focus is building systems and delegating, since he tends to stay overly hands-on in day-to-day operations as an entrepreneur.

In this episode

  1. 01:58Welcome: Introducing Marc Weisi of YieldWink
  2. 02:39From Wall Street layoffs to real estate: Marc's journey
  3. 04:04Marc's strengths: financial underwriting and operations
  4. 05:57Where Marc is focused on improving: delegation and systems
  5. 06:38Why hospitality in Puerto Rico is a growing opportunity
  6. 08:02Location: San Juan and the busiest airport in the Caribbean
  7. 08:39Market risks: macro environment and geopolitical tension
  8. 09:53Key non-deal metric: guest feedback and reviews
  9. 11:40Niche: short-term stays, average 2.5 days, 50% US travelers
  10. 13:06Why Puerto Rico is the safest Caribbean destination

About the guest

Marc Weisi runs YieldWink, focused on hospitality investing in Puerto Rico. He started in real estate with small condos in northern New Jersey after a 2011 Wall Street layoff experience, scaled into small and then institutional-size multifamily, and over the last three years transitioned into boutique hotel hospitality in the San Juan metro area of Puerto Rico.

Listen to the audio

“I like to say that it's probably the safest Caribbean destination that they could think of. There's all the same US law enforcement.”

Marc Weisi

“I'm a big believer in business as a tool... one of the biggest benefits of business is making an impact in the local community and helping others grow their business alongside you.”

Marc Weisi

“We're in the business of creating memories. I think if people have great experiences, they tend to reward you for it.”

Marc Weisi
Puerto Rico real estatehospitality investingboutique hotelsCaribbean marketSan Juanshort-term rentalsasset managementunderwriting

Questions answered in this episode

Is Puerto Rico a safe place to invest in real estate compared to other Caribbean islands?

Marc Weisi says Puerto Rico is probably the safest Caribbean destination to invest in because it falls under the same US law enforcement and property rights and laws that investors in the States are already used to. This reduces the legal and security risk compared to investing in a foreign country.

What kind of real estate opportunity is Marc Weisi focused on in Puerto Rico?

He is focused on hospitality, specifically boutique hotels in the San Juan metro area. He says hospitality in Puerto Rico has grown every year for the last five years, including through COVID, as more Americans consider the island a vacation destination instead of places like the Dominican Republic or Jamaica.

What is the average guest stay and traveler mix for Marc's hospitality business?

The average stay is about two and a half days, geared toward short-term guests such as long-weekend travelers. Roughly 50% of traffic comes from the US states, with the rest coming from the island itself, other Caribbean islands, South America, and Europe.

How did Marc Weisi get started in real estate before moving into hospitality?

After graduating college in 2011 into a tough job market and working on Wall Street during a period of mass layoffs, Marc decided he needed a financial exit plan outside of a 9-to-5 job. He started in real estate with small condos in northern New Jersey, scaled up to small multifamily and then institutional-size multifamily, before transitioning into Puerto Rico hospitality about three years ago.

What differentiates a boutique hotel from an Airbnb or a big branded hotel chain?

Marc describes a boutique hotel as sitting in the middle: it can offer services and amenities that a typical Airbnb can't, but without the bureaucracy of a large flagged hotel like a Marriott or Hilton. He says the differentiator is the personal touch from staff who genuinely care about helping guests.

What market risks is Marc Weisi watching in his hospitality business?

He points to the macro environment as his biggest concern outside of his control, specifically the war in the Middle East, potential inflation, and a cooling economy. He says he doesn't lose sleep over it but tries to have a plan in place and focuses energy on things within his control.

Resources and links

Full transcript

Marc Weisi (00:00)

Yeah, so I like to say that it’s probably the safest Caribbean destination that they could think of. There’s all the same US law enforcement. ⁓ That’s one thing. I think that’s a big concern for people, especially families. ⁓

I think it has pretty much everything that could rival any other Caribbean destination. has beautiful beaches. It has basically untouched natural forests and different geographies like that.

Scott Bursey (01:58)

Welcome back to the Real Estate Pros Podcast. I’m your host, Scott Bursey. Today, we’re thrilled to welcome a true authority in the real estate investment strategy figure. Marc Weisi of YieldWink. Marc is known for his disciplined approach to optimizing investor returns and uncovering unique opportunities for growth in the current Market. Welcome to the show, Marc.

Marc Weisi (02:22)

I appreciate it Scott, thanks for having me on.

Scott Bursey (02:24)

It is awesome having you here. And before we dive into the Market dynamics, please give our audience the story of your journey. How did you first start your career and where are you at now?

Marc Weisi (02:39)

Absolutely. So my journey starts back post college. ⁓

was coming out of college into a tough job Market, 2011, and I was working in ⁓ Wall Street, and I saw at that time, it was a really tough time to be on Wall Street. were, you know, mass layoffs and a lot of people who had spent their entire careers, you know, getting to these roles and then unfortunately coming in one day and being told, you know, to see the door. And so from that experience, I pretty much, you know, had a trial by fire. I learned very quickly that, you know, no job is secure, no nine to five is,

can be really dependent upon for your financial future. And so I kept working. I definitely, you know, still put my career first and wanted to climb the corporate ladder. But with the back of my head, I always knew that I wanted to have some kind of an exit plan, some kind of an escape hatch should, you know, should I need it. And so I got started in real estate a few years later and started off at the smallest possible increment of real estate that you get to, which was for me condos in northern New

Jersey

and kind of scaled over a number of years up to small multifamily and then eventually ⁓ you know institutional size multifamily and ⁓ from there that’s been the last three-ish years I’ve kind of transitioned into now doing hospitality in Puerto Rico of all places so that’s the me in the nutshell.

Scott Bursey (04:04)

How fascinating, that’s awesome. So what are some of the strengths that you feel that you’re excelling at right now with the YieldWink?

Marc Weisi (04:14)

Yeah, so my background is a lot in.

Well, two things really, financial analysis, which I do a lot of underwriting on any projects I’m involved with, and then also operations. So once we take over the project, once the construction is done, I like to handle a lot of the, ⁓ what would be called asset management. ⁓ In hospitality matters, I would say more so than maybe any other ⁓ flavor of real estate, because like we talking about earlier, there’s just so much volume, so much coming and going inside of a given hotel. And so the operations really has to be

super, super tight and I enjoy that. That for me is challenge.

Scott Bursey (04:52)

Yes, yes. And what are some areas that you’re looking at ⁓ perhaps improving on? know Puerto Rico presents some unique challenges, but what are some areas that you’re looking at improving on, if you could give us the rundown on a couple of those.

Marc Weisi (05:57)

Yeah, I think my biggest area of improvement is kind of similar to what a lot of entrepreneurs experience is I am…

super involved with my day-to-day business and I love building and I love the act of bringing something to life but I have a hard time sometimes handing off the reins and delegating and kind of know handing off things to other people employees or otherwise and so I think that’s something that I’m really focused on this year is creating systems so that you know other people can succeed and I can you know stop wearing so many hats and kind of focus on my lane.

Scott Bursey (06:30)

Absolutely.

Tell us about some of the opportunities in Puerto Rico, if you would.

Marc Weisi (06:38)

sure so hospitality is really my favorite opportunity going on right now.

Puerto Rico. Puerto Rico is a beautiful island, really paradise, wonderful people here, just an awesome culture and history and it is part of the US. you know a lot of the same property rights and laws and things like that still exist here as investors would be used to in the States. So that’s one thing that gives me a little bit of security versus maybe investing abroad. But at the same time it’s a very different environment and so for me one of the first things I tried to do when coming here was just talking to other

people that do it. So trying to get in the right real estate circles, joining the local RIA, talking to different people, know, different eventual team members potentially. So lawyers, accountants, other investors, and trying to get a lay of the land. And so today I believe more so than even when I first started that hospitality is a real opportunity in Puerto Rico because it’s grown ⁓ really for the last five years every year. The hospitality here has grown through COVID and I think it’s starting to

enter a lot more of ⁓ Americans’ minds as far as being a ⁓ vacation destination versus maybe in years past where it was Dominican Republic or it was Jamaica or one of these ⁓ Caribbean islands that neighbors Puerto Rico.

Scott Bursey (07:57)

Absolutely.

What portion of Puerto Rico are you in?

Marc Weisi (08:02)

I’m in Sen Wan, I’m in the Sen Wan Capital Metro area.

Scott Bursey (08:06)

Right by the major airport then.

Marc Weisi (08:10)

Exactly, yeah. That’s actually the busiest airport in the Caribbean. So ⁓ something like 90 % of the passenger traffic for the island comes through that airport and we love that because that means that a lot of people are here ⁓ and so you know our goal is to compete for those people’s lodging. ⁓

Scott Bursey (08:28)

Sure.

absolutely.

What major Market risk or threat are you watching closely right now, Marc?

Marc Weisi (08:39)

Right now, my biggest concern is really something that’s outside of our control as investors, the macro environment. So with the war in the Middle East and the tensions going on there and potentially some inflation going on and a cooling economy, all those things are something that I pay attention to. Not necessarily something that keeps me up at night, but definitely something that I try to have a plan in place for. You can’t control, you shouldn’t worry about things you can’t control. So I try to focus on things in my business.

⁓ that we can create plans for and around.

Scott Bursey (09:13)

Absolutely.

And hey, that’s the wise approach in my book. Marc, something that’s been on my mind here. If you could walk us through what is your most valuable non-deal related, let’s say metric, determining the health of your enterprise as it stands today.

Marc Weisi (09:35)

Most what metric, sorry?

Scott Bursey (09:38)

A deal related metric as far as putting together deals within your network of people. If you could give us a little insight on that if you would.

Marc Weisi (09:53)

So like a non, you said something specific there, like a non-quantifiable metric you said? Or I’m sorry, I missed the beginning.

Scott Bursey (09:58)

That would be yes

that would be fine anything like that really what do you feel is going to enable your organization to grow I guess is a better way of saying that.

Marc Weisi (10:48)

Yeah, no, that makes a lot of sense.

So I think the biggest metric for us is our customer feedback. In our case, it’s our guests that stay with us. If they’re having a good stay and that shows up in the reviews, it shows up in our staff’s conversations with guests, then we’re doing something right. And I think there are a ton of other metrics that you can use to assess a hospitality business. But for me, we’re in the business of creating memories. I think if people have great experiences, they tend to reward you for it.

Scott Bursey (11:20)

absolutely. Now are you concentrating on more of the long-term stay? Let’s say a business person wants to come in for two or three weeks or are you concentrating more on the short-term? If you could elaborate just a little bit on your main focus, your niche if you would.

Marc Weisi (11:40)

Yeah, so our niche is short-term stays, our average stays around two and a half days.

somebody who comes here about 50 % of our traffic comes from the states and the rest is from a variety of on the island itself and other Caribbean islands as well as South America and Europe so we’re heavily tilted towards US travelers and so you know our focus is on those people that are coming in maybe for a long weekend and giving them as much as they can do and as many experiences that they can you know take on in that weekend.

Scott Bursey (12:11)

Absolutely. What sort of amenities are you offering?

Marc Weisi (12:17)

So we have a ton of, I’m a big believer in business as a tool. Obviously, you have to make money in business or else it’s not sustainable. But for me, one of the biggest benefits of business is making an impact in the local community and helping others grow their business alongside you. And so one of the things that we did early on was form partnerships with other small and medium sized business owners here. So things like tours and excursions throughout the island. ⁓ We have now partnerships with local breweries, ⁓

We have a number of different experiences. There’s an art tour that we’ve operated that we’ve recently built a relationship with. So referring our guests to those things because it’s kind of a win-win. We’re helping them grow their business. We’re helping our guests have a really great time. And that all results in us doing well in long term.

Scott Bursey (13:06)

Okay, let’s say that you’re speaking to somebody here on US soil. It’s never been to Puerto Rico, although Puerto Rico is part of the United States, but what would you like them to know about the island?

Marc Weisi (13:19)

Yeah, so I like to say that it’s probably the safest Caribbean destination that they could think of. There’s all the same US law enforcement. ⁓ That’s one thing. I think that’s a big concern for people, especially families. ⁓

I think it has pretty much everything that could rival any other Caribbean destination. has beautiful beaches. It has basically untouched natural forests and different geographies like that.

It has the only ⁓ rainforest actually in the U.S. ⁓ So that’s a beautiful thing. And it has a ton of history. The island of Puerto Rico dates back at least ⁓ on a colonial standpoint dates back to the 15th century. So even pre-dates the U.S. So there’s a ton

see and learn and you know experience here.

Scott Bursey (14:06)

Absolutely

what’s one big takeaway or something you’d like to highlight about what you offer people at your facility.

Marc Weisi (14:18)

Yeah, so…

I think one thing that is kind of unique about a Boudique Hotel versus maybe a big flagged hotel or even on a smaller term, you know, an Airbnb is that we’re somewhere in the middle of the two. We can offer certain things that maybe the guys on the lower end and Airbnbs can’t offer, but we don’t have the bureaucracy. We can be more nimble, more adaptable than somebody at the, you know, higher end, say a Marriott or Hilton. ⁓ So I would say it’s our personal touch. I think that’s what kind of sets us apart is we really care.

staff that come to work every day and are super excited about ⁓ helping guests find whatever they’re looking for. ⁓ And that includes everybody from the cleaners to me and my partners, showing up super inspired. And that’s what it’s all about, I think, is why we do it, is to see smiles on the faces of people that stay with us.

Scott Bursey (15:52)

Isn’t

that the truth though? The personal touch when it comes to hospitality. Couldn’t agree more and love your stance. Before we let you go, Marc, for our listeners who, you know, want to follow your journey or ⁓ want to know more about your culture, what you offer there on the island, how can they contact you?

Marc Weisi (16:15)

Yeah, absolutely. So they can get in touch with me. ⁓ M-W-E-I-S-I at YieldWink.com.

They can also, I’ll give out my personal cell phone if they want to reach out. very open to have discussions with other people who are going along the same journey. I like to say that I’ve gotten here by standing on the shoulders of giants, the old saying. I’ve definitely gotten a lot of help along the way, so if I can pay that forward in any way, I’m definitely open to it. My phone number is 908-319-4351 and feel free to text me or call me there.

Scott Bursey (16:50)

For anybody that wants to check out the island, there you go. Marc, thank you for being on the show. This has been awesome.

Marc Weisi (16:55)

You

Thanks, Scott. Really pleasure.

Scott Bursey (17:02)

And thank you to all of our listeners for tuning in. If you found value in today’s episode, please make sure you’re subscribed. Until next time, keep your standards high and your vision clear. We’ll see you in the next episode, everyone.

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