Commercial Real Estate DealPRO Mastermind #23
September 13th, 2025
In this September 13, 2025 DealPRO Mastermind, Cherif guides a new investor in Puerto Rico on where to start, how to leverage local incentives, and creative strategies for developing family-owned land. He also covers how to manage property managers with clear expectations, the smartest ways to boost income and reduce debt, and the financial habits every investor needs today. A high-value session packed with practical, actionable advice.
Good morning or good afternoon, wherever you are. Today is September 13, 2025 and we are on our Commercial Real Estate Deal Pro Mastermind Call and we are all on.
So Ashley, how are you? I’m doing very well, how are you? Great, thank you. Let’s go ahead and get started. Okay, we got a lot of great questions that were sent in.
Today we’re going to start with Pablo. He is a brand new Commercial Deal Pro investor, so we want to welcome him. He sent in a little introduction which I sent over to you and I know you read about who he is and what he wants to do on his short-term and long-term goals and so I’m going to start with his first question.
He said, if you were currently in my position right now in 2025, what would you do step by step and what opportunities would you go for? Out of all the strategies, what would be the best way to start making income on the island of Puerto Rico that you would focus on in my position? I am boots on the ground, I am ready and want to take action as soon as possible. Well, that’s just fantastic. Pablo, you know I am big on Puerto Rico.
I have a huge inventory of commercial mixed-use properties there. I’ve always found it to be a very unique location, Old San Juan in particular. I think Old San Juan, Puerto Rico is isolated from the world and the island of Puerto Rico has had incredible incentives for people to go and invest there and make things happen.
The problem in general, and I’ll tell you the opportunity, but the problem in general in Puerto Rico is since 1815, believe it or not, it has attracted people with tax incentives. So that has worked sometimes and some other times it didn’t. For example, there were pharmaceutical tax incentives that were stopped in 2006.
So we lost a lot of momentum there and what happened is the pharmaceutical companies said, well, we don’t have the same incentives, so we need to move some operations in the US, etc. But then they quickly rolled out new incentives in 2012, which attracted a lot of people and they said, you come in there to the island, you buy a house within the first two years, you get a special application approved by Congress because it’s all part of the US, we are going to help you reduce your taxes down to very low amounts. And what happened is it attracted a lot of crypto people, Bitcoin people that had bought Bitcoin for a dollar or $10 or $100.
And right now, these people came in, they don’t know real estate, they don’t know investing, they don’t know business. Many of them have aspirations to do stuff when Bitcoin goes up. Well, Bitcoin went up all the way to 124,000.
And I thought they’re going to be cashing out and investing on the island and buying hotels and whatever. And yet, that didn’t happen. They actually said, well, we think it’s going to go to 250,000.
So they’re holding on these little activities. Now, on the other hand, there are some other people that came in and saw the opportunities, a lot of people from Florida, a lot of people from New York, and they started big hedge funds and started buying hotels and creating jobs, et cetera. I found Old San Juan to be kind of isolated from all that.
It has its own tax incentives based on the historic district that is Ponce in south of the island, has another port that brings cruise ships that will be up and coming in the next, I think, decade or so. So all this is good to understand the kind of basic economics what’s happening in the island. And if you’re asking me what you should do now, I suggest for you to join investment clubs.
Example, this company called RIA, Real Estate Investment Association in Puerto Rico. You can actually find them by just looking R-E-I-A Rico, R-E-I-A space Rico, and you can join them. I spoke in that for them several times.
They invite me every now and then. They have a group on WhatsApp and I’m looking, they have a website. Yeah, riarico.eventbrite.com. And they hold meetings once a week and they talk about the deals that are happening.
They talk about who’s buying what, who’s going to give you loans, who’s doing this. So that group of people on the island is mixed with locals and people coming from the outside that want to invest. And I spoke there and I found people there to be very interesting, diverse people with private license, like attorneys, architect, engineers, contractors, et cetera.
That will be a boost for you, Pablo. It will be amazing. You’ll meet some people that I set up on the island with real estate funds because nobody was setting up real estate funds there.
For example, Eduardo Joy set up a fund, was very successful, took a small place in Santurce, converted, rehabbed it, got some tax benefits, made it a hotel and actually came back to me and said, Sharif, you impacted me in a great way. And I want to buy one of your buildings. And I ended up giving him one building, 208 Cayes San Sebastian.
And he bought it and he’s now turning it into a 35 unit hotel. I was going to do the project, but timing was not good for me to do any big projects. And he’s doing it, actually he’s going to close next year.
So we gave him easy terms. So it will be a win-win and he’s doing great with it. I mean, it transformed his life and he attended these meetings and he met people and he set up the fund and he was able to raise capital.
So one of the best ways for you to grow is to know where the action is, who’s doing what, network with them, and then see how you maybe eventually can raise capital to do your own because everybody wants to team up with a local person because it makes everybody’s life easier. What’s the follow-up question? All right, his next question. I saw the video that you were explaining how to get lines of credit in the banks in the US.
I was thinking on going over to Florida and to do what you were teaching in the video to access the capital. Can I and should I do that? You could, but the problem is in Florida, the Florida bank wants a local address in Florida. And you know, that training that I did about how to build your own credit is based on a simple idea of you take some money.
Well, first you get some credit cards and 5,000 here, 2,000 there, et cetera. You can actually invoice yourself through PayPal, cash out that money. It’s not how much you have in cash advances, how much they give you in credit.
And then let’s say you get 20,000 out or something, or 10,000 out. You deposit it in one bank and then you open a CD and you borrow against the CD. And then when you borrow, you got the money.
So you go to another bank, deposit it in a new bank account. And then you open a CD and then you borrow against the CD. They usually give you a hundred percent loans on personal loans.
If you put it under an LLC or a C Corp that’s new, they’ll give you 80 to 90% loan on it. The key thing is you do that five, six times, the 20,000 or the 10,000 is now 50 to a hundred thousand borrowed. But at the end, the last bank gave you the money, gave you a cashier check and you just make payments.
The CD is for six months. You keep making payments for six months and then you pay off the first bank. They release your money.
You pay off the second bank, you release the money, et cetera. That is a great way to eventually, after you have all this paid, these banks report under your social security, if you did it personally, that you borrowed and paid on time. And then you can go back to the same banks and ask for a personal credit line.
They’ll give you 5,000 to 20,000. It depends on the banks. Wells Fargo does 10,000 usually.
Chase Bank does 5,000. This is my feedback that I get from the students that have done this. The key thing is you need to get an address in Florida.
If you have a family member in Florida or something, use their address. And they may need even a driver’s license as an ID from Florida. If you tell them you don’t have it, use your passport because U.S. passport, Puerto Rico or U.S., they can tell the difference.
I would do it if it helps you. And that could boost your credit a little bit and make it happen. So, Pablo, do you have any questions about that before we move on to the next? No, no.
I’m good. Okay. All right.
His next question, he said my grandfather owns a seven-acre lot in Ponce and wants to get rid of it. He is asking 4.5 million for it because of a project that he had but could never do it because of the financing. This project has all the permits.
It’s ready to and start the project. I believe it is 172 apartment complex. Is there any other creative ways that I could present to him a deal instead of trying to sell the project to a developer, maybe reaching out to a fast food restaurant or QSR? What are your thoughts? All right.
So, the United States right now, first of all, so you know, is going through a very hard time with land developments and construction. Let me preface this with that understanding. Why? Because we have interest rates are still very high.
And people got spoiled with the 3% interest rate. I started real estate in 1989. My first deal, I got it at 9% or 9.25%. And I remember when I told people they were high-fiving me.
They’re like, you’re incredible. How did you shed that 9.25% interest rate? How did you do it? Because everybody was paying 9.75% and whatever. So, the interest rates are too high.
And the numbers have adjusted to the lower interest rates from before. Still, people want a lot of money. Still, people cannot move because they can’t get rid of the home they have.
Like in New York, people are moving to Florida. But now, they had refinanced their homes at 3%, 3.5%. They can’t go get a home half the price in Florida because now, the insurance also went up. The interest rates are up.
The utilities are up. The construction cost or maintenance on properties is up. So, that is a drop also now in land prices all over.
Every problem, if you focus on the problem only, you’re going to depress yourself. But if you look at the problem and tell yourself, wow, there is a great opportunity here. What can I do with this? Creativity is where money is made.
You become creative. How do you become creative? Developers need land to develop. Now, people are moving to Puerto Rico.
The wealthy are moving. Middle class is moving because a lot of people want some tax incentives. A lot of people like it because the weather, etc.
So, what’s happening is your grandfather, you can propose to him a couple things. Number one, promote the property as a joint venture with a developer. All right? So, it has to be developed not as a sale because you said specifically and I looked at your question, he wants to get rid of.
That’s a very good choice of words. I can feel the frustration. It’s not that he wants to sell it.
He wants to get rid of it. So, that’s good because if he’s willing to sell, there are many ways to sell. But one of the best ways to sell a land is to offer it to developers and say, I’m willing to do a joint venture.
I can pledge my land and then we can work out as the sales occur, you can start paying me, etc. Of course, it’s your grandfather. So, I’d assume he’s in his maybe 70s or something and he wants to cash out.
He wants to enjoy money. Well, maybe he can work with a lender or something like, I’ll give option to buy the land and give me a small payment. So, it would be like a lease with an option to buy with a very small payment, like a land 4.5 million.
Maybe you can get them to pay him 8,500 a month. That’s 100,000 years doing nothing and watching his land being developed and being cut into parcels of lots that could be sold. And as they sell each one, they pay him so much.
If I’m a developer and somebody pledges the land to me for small upfront money and an opportunity to develop it, now I have actually reduced my upfront cost. So, I can do the construction, I can pay the insurance, I can pay the utilities, I can pay all the entitlement and the delays with the cities and the counties and all that to get it done. So, number one, be creative by offering joint ventures to the developers.
How do you find who are the developers on the island or in a specific area in the United States? Look for what’s being promoted. Right now, just the other day, I was opening Facebook and somebody promoted to me brand new developments on the west side of the island. Big developers saying this is a pre-sale for these beautiful condos.
I mean, gorgeous stuff like Miami, Brickell Road. So, look at who are the developers coming because big developers are coming to Puerto Rico. And then you make the calls to these developers and say, we, not my grandpa, we have a land, my family have a land, would like to offer it to you.
We’re very flexible on the terms. We’re talking to different people. Are you interested in looking at it? They’re going to come and look out of curiosity, but you’re going to open your networking.
Next thing you know, these people raise capital. So, what they will do is if more money comes than they need, they’re going to come to you and say, hey, maybe we can make a deal happen. So, open it for joint venture.
That’s going to be very powerful. And the same principles apply anywhere in the world, actually. All right.
The creativity with land is in offering the person who’s going to add value to the land to come in with easy terms. You’re with me so far? Okay. Number two, you could set up a real estate fund.
I don’t know your financial situation now, but I set up the funds for people. I do it less than anybody for 25,000. I do it turnkey.
I’ve done it for people in Puerto Rico. I would suggest for you to set it up in Florida. We can set it up for you in Florida to do the investments in Puerto Rico.
I know exactly how it’s done because you can raise money in the US from Puerto Ricans who are wealthy that moved to Florida and New York, and they would invest because they want to go back and spend Christmas and spend time and love their island. So, you can be the one saying, you can come and invest as little as 25,000. We’re going to develop this land.
And then you can just take the land, get the entitlement. You work on that and just develop it one parcel at a time. And that 4.5 million, by the time you finish, it’s going to be worth 20 million, 25 million in an exit.
And it’s just a bonanza of opportunity. Ponce is going to grow because cruises are growing, and this is a good port, and it’s going to come back to its glory. It’s happening.
It’s happening very slowly, but it’s happening. And there is demand for housing because after the hurricane, we still are still fighting to get money from FEMA, get money from insurance companies. It’s kind of crazy what has happened.
So, hopefully these ideas, to recap, join the investment club to know what’s going on. Number two, be creative with the land that your father have by talking to other developers, by looking at if people would want to invest with you. Try to see what the entitlement process will be because if you just entitle it, if you just finish what’s needed and divide it into parcels, the value goes up 25 to 50%.
And if you’re creative on terms with anybody coming in, you can then sell the lots instead of selling the whole land. And finally, if I can give you personal suggestion for you, the most demand on the island is for people doing construction. The island of Puerto Rico has a lot of potential with construction.
There aren’t enough contractors. So, if you want to become a millionaire in the next three years, get into construction. I kid you not.
I mean, I have my team. I do the rooftop. I do a roof for 10,000.
And my neighbor, I said, how much did you pay for a roof? He said, 26,000. I said, 26,000? Your roof is smaller than mine. He said, how much did you pay? I said, 10,000.
He said, yeah, you have your team. I couldn’t find anybody. Well, the guy came and said 26.
I said, I’ll pay you now. So, that’s how much demand there is. So, get in there.
Make it happen. Put the pieces together. And step by step, every day, a little improvement, you’ll make it happen.
Hopefully, that helps you. I’m so glad. And I hope to meet you in person next time in Puerto Rico.
Very good. And Sheree- He wants to say something. He wants to say something.
Absolutely. I just wanted to say thank you. That’s really good advice.
And hopefully, meet you soon. Thank you. Thank you very much.
Very good. And you kind of just hit on this with kind of leading him into the construction, but he said here on the island, is there any other product or service that you’d recommend getting into just to start generating income now? Well, the most powerful thing is you have to have money to do these projects that are small rehabs, like in Santurce or something, where you can do, if it’s a destination location, Airbnb is good. If it’s not a destination location, you’re going to lose money with Airbnb.
But there is demand for rentals, and you can rehab them and do rent to own, where people come and give you upfront money and give you positive cash flow until they exercise the option to buy. I sold a property in Mameas in El Yunque. It’s kind of out.
I’m usually only in Old San Juan, but I fell in love with that property. It was a great location. And then I couldn’t sell it.
As soon as I put it easy terms, they paid me the full price I asked. And it was a beautiful deal because the people were coming from California, selling a home in Napa Valley. I said, just give me this upfront money, and I’ll carry the financing.
And they did it. So ideally, when you join that investment club, you’re going to find people that have a little money. And you can put little money with little money and you can do partnerships until you’re ready to set up your own real estate fund, because you will gain knowledge, good connection, and then you can raise money and with confidence do deals.
So hopefully that works for you. Very good. Thank you, Sharif.
All right, we are going to move on to Roger. His questions are coming in from New Mexico. Roger has three questions.
He said, I have a small team who manages my portfolio of single family rentals and duplexes. I have a property manager who’s doing a good job, but every time I sell property or he locks in a lease, I feel he’s looking for a bonus or a raise. I feel he’s saying, hey, I did this for you, now do this for me.
How do you suggest I answer him now? And how should I manage this from happening in the past with him and others? So in my 40 years of leadership and management, when I managed hotels for the billionaire I worked for, and when I worked for Hilton as a VP for the West Coast and took hotels and casinos in Puerto Rico for Hilton, et cetera, I learned one thing. People who embark on a specific task or in a job, first they underestimate themselves, then they overvalue their contribution. And the problem is in the beginning, you need to give them confidence and motivate them so they can do the job, give them direction and support.
Later, they get so full of themselves based on whatever results that you have been nurturing into them that they start asking for more money, more compensation, they want more attention, et cetera. So my suggestion with this person, your property manager, is sit down and explain to him his responsibilities and duties. You are responsible for this and this and this and this.
And your duties are to make sure this is rented, this is done this way, this is done that way, and to comply with any reasonable request. And this list may be modified and adjusted as the job grows or as the market changes. You add these wordings.
Now, have it all spelled out in writing. It’s not just something that you discuss. You have it in writing, you sit down with him and you start with something positive, as in thanking them sincerely for something you like about them.
I like the fact that you grew in the position and you understand this and this and this. Why do you start something with something positive? Because it opens an individual’s mind. You can be discussing something, going back and forth with somebody, maybe even arguing, and then you say, I like something that you said.
Immediately, they will stop. They want to know what you liked about what they said. You see, as soon as you have the positive start, you can then explain to them, here is what I expect from you, here are the responsibilities, here are the duties.
You are doing a great job. This is your job to have the place rented. This is your job to have the lease signed.
This is your job to do the inventory of items inside that unit. He needs to know what his job entails. Then you can offer him something like, if you’d like to, you mentioned this and that about more compensation.
If you’d like to go on pure commissions, like a real estate agent, we can work that out. But I’d like to reiterate the benefits of how our arrangement works. That’s a win-win for you and me.
This is how you present it. We can give you something else, but let me tell you why you have the best part of the deal here for yourself. When people have these expectations of me giving them promotions or extra money, I reiterate the benefit that they have working for me under a specific structure.
I also explain to them what the market is regarding that job. I can say, yeah, I know you’re doing a great job and I want you to be happy, but you have to understand that if I do that opening, I can bring somebody with more experience. I can bring somebody with more connections, but I prefer to continue with you.
Tell me if you’re not happy, what can I do? And you’ll be amazed bringing that reality to an individual, how they will adjust and be grateful for what they have. Every now and then you need to remind them. Now, with all that said, it is always, I hate to be so absolute, it is always good to have some type of bonus because the study of economics is a study of incentives.
You give them incentives, they’re going to do more, but I said they got to do more. It has to exceed certain results. It is your job.
It is what you can do to get this job. It is what you can do to sustain it. Your responsibility is this, duties are that.
So once you reach more than this, if you do more than that, if you get me these reports and you follow up this way, there is that threshold that you’ve done higher in production and results, and I will compensate you this way or that way. A lot of people think they’re just getting paid for time and effort. I don’t give a hoot how much time or effort they spent.
All I care for is what results that I get from the production they give me. So when people say, I was here working so hard. Yeah, but we still did not rent a unit.
You put the advertisement and it got clicked off and you didn’t realize it was clicked off. I’m looking on the weekend, it’s not unposted. So that’s when we have to have the meeting of the minds.
It is what you do. It is what others could do in your position. Here’s your other choice with that position.
If we agree on your job duties and responsibilities, then let me tell you how you would be compensated more if you do more. And if not, then let’s just part amicably, but I’d love for you to be with me and to stay happy, et cetera. Then let them simmer on it and then do a follow-up within a few days.
Hopefully that helps you, Roger, because I know it’s tough as the market gets tougher and people can’t afford just normal living wages anymore. Thank you very much, Sharif. Let’s move on to Roger’s second question.
He said, in a previous call in 2023, I heard you talking about how every employee, investor, professional wants out. I’m assuming you are talking about retirement or cashing out. What advice further down do you have for investors today? How to correctly analyze life, meaning retirement, holding a house, a business? Okay.
So let’s, first of all, start about how do you actually… What’s my advice regarding investors today? Number one thing you got to do in the world of finance. What’s the difference between finance and accounting? Accounting is knowing where the money does this and that. Finance is knowing what to do with the money and how the money is actually functioning.
So number one most important thing is this, know your expenses and where you’re spending the money. The money is going up. Some people pay credit cards, just click, click, I’m paying the credit card.
What is that item? What is that item? What did I spend here? How come I made this and this is actually what I spent here and here and here? Know where every penny is going. The task may take you a couple months to figure out every penny. Put it in an Excel sheet.
Oh, you don’t know how to use Excel? Write it handwritten. It’s fine. Know your expenses and immediately thereafter know where you can cut.
Where can I cut? This is useless. I don’t need the storage room. I don’t need the extra expense for this person to do this.
I don’t need the outside extra office that receives the mail, that receives this. I can have it here. Even if you cut pennies, once you start cutting, you’re going to start what else is superfluous that you don’t need.
Know your expenses, know where to cut. Number two, know where your income is coming from and how it can be increased. Know where your income is coming from.
When I do this, I get that. When this other person working for me does this. Know your expenses first and know your income and how you can increase it.
What do I mean? What promotion and what effort produces the biggest results? 20% of our efforts produce 80% of the results. What are these 20% and how can I do more of them? Immediately thereafter, you need to look at your debt and liabilities and exposure. And that’s what you need to reduce.
What can I do to reduce my debt? For example, I’m walking the talk. As a matter of fact, just a few months ago, I decided, okay, these properties have reached that potential. They’re already producing the maximum income.
There’s nothing more I can do here. And these properties are doing better and they’re going to do more. I decided to sell these properties because there will be an easy sale because they’re producing income and everybody wants income and reduce my debt.
So reduce your debt, which reduces your liabilities and your exposure. And remember, you don’t want to be like, oh, I have expenses. I have this.
I got to appease that. I got to maintain to this. Because you can be reasonable all the way to bankruptcy.
You can be reasonable all the way to bankruptcy. Don’t be so reasonable to a point where you screw yourself. Not in the financial world, very hard to recover because nobody will stand with you when you’re down.
When you’re down, you’re going to feel alone. You’re going to feel the world is against you. You’re going to give in on yourself and you have to learn how to remotivate yourself and focus your mind on how to recreate wealth, how to get the momentum and how to make the most of what you have.
So cut your debt, reduce it. And then once you reduce your debt, get credit lines. So I sell a building, I pay off the other and I get a credit line.
Why? Because now the credit line, I can pull it anytime I need if there are good deals. And good deals are based on cash flow or cash out. I’m going to buy it because it’s going to produce more cash flow than my payments and my expenses.
Or I’m going to buy it because I know the market is worth more so I can flip it. And then all I have to worry about is how to reduce expenses, how to maybe cut the financing so I can have cash flow but I can defer my taxes, etc. So reduce debt on properties, get credit lines on whatever is available for you so you can pounce on good deals or you can actually buy properties.
If you bought a property for cash flow, then immediately you want to refinance it to get that long-term loan and get your money back out to do another deal, pay down the credit line. If you’re buying it to sell it, then now you have more money to work with. Eventually you have reserves and you have credit lines.
The end goal is to be solvent. Solvent meaning more money coming in than money going out. The second end goal after being solvent, that means having more cash flow than expenses, is to have the least amount of daily obligations.
Now I have achieved that because I had in my mind that my goal was to work on a lifestyle whereby my physical existence is not necessary. So I could be in Puerto Rico if needed or I could be in California if I need to or I could be in Europe if I want to. My physical existence is not necessary.
I could do this call if I’m sitting on a cruise or if I’m sitting in a home in France. Okay, so physical existence, that’s the second aspect. As soon as you’re solvent,