I sat down with Stephanie Cabral, a full-time real estate investor who built a 19-unit portfolio while working just a fraction of the hours most landlords put in. Stephanie shares the exact moment she realized she couldn’t keep being the person who answers every maintenance call, and the AI tool she built in response, called Pam, that now runs her maintenance operations while still keeping her in control. If you’ve ever felt trapped by your own portfolio, or wondered how to bring AI into your real estate business without losing oversight, this conversation will change how you think about scaling.
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Hello everyone. I’m Adrienne Green and today we’re here with my friend Stephanie Cabral. Thank you for joining me, Stephanie.
Thanks so much for having me, Adrienne.
Here we focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start. Stephanie is a personal example of that. She’s created the life of her dreams, and she’s created a tool to help others do the same. I’m excited to share her story and this awesome tool she built. So let’s jump in. Stephanie, before we get into the how, give us the what. What does your portfolio look like today?
I’m a full-time investor. I have 19 units, five of them are furnished, actually 19 and a half. One of them is something I control, but it will come into fruition in the future. It’s an equity play, but cash flow negative at the moment, but it will be an amazing tool in the future. So I always say 19 and a half. I was very lucky. I started buying in 2012.
I did the majority of my buying from 2015 to 2019, so I really got the benefit of the upturn in the market. I was able to leverage great financing, refinances, to buy more. So I have a not overly leveraged, low interest rate portfolio. Even with not a huge portfolio, it is an extremely optimized, cash-producing portfolio. I’ve been very, very lucky. The midterm rentals have made a big difference as well. And I self-manage that portfolio, which preserves not only cash flow, which made the difference between me being financially independent and not, but also gave me control and transparency into my portfolio that improved my tenant retention. It just really snowballed into a better portfolio in general.
I am hearing already so many big lessons for our listeners. If you’re in it a few years and stressing out because you’re not getting cash flow, it’s okay, time addresses that. And second, the power of self-managing. So where did you get started? Can you tell us a little bit about how you got into real estate investing in the first place?
Such an interesting story. I am a recovering attorney. I practiced for ten years and I really didn’t like it. I actually knew coming out of law school that I didn’t want to be an attorney. So I took a job at a family-owned practice that gave me extreme flexibility so that I could start to look for what else I was going to do while still having some stable income. The trade-off was it wasn’t very much income. So I was underemployed, underpaid, at the same time high standards for living. Really difficult combination. It took me a little while, but my mom recommended I buy a duplex. That sent me into a rage because I couldn’t even afford rent in an apartment, how could I possibly buy two buildings? I didn’t understand a duplex was one building and two units. Once I calmed down and took the time to understand what she was talking about, I learned that you could also leverage the income from that other unit to help increase your buying power. So I was able to buy a condemned duplex in the best town, in a really great spot, and renovate it.
So my very first deal, I buy this condemned project and do a BRRR deal on it. Buy a distressed property, renovate it to push equity up, rent it out to stabilize it, and then refinance it to recapture the equity. I don’t even know what I’m investing. I just have a great mentor at the time walking me through all of these steps, which was huge, and gave me this feeling of what could possibly go wrong. Honestly, almost nothing went wrong, which is ridiculous. I’ve never had a project go so smoothly as that first one. What was amazing about that, and I always share this, I think it’s really important, that was one of the most shameful times in my life, and it also became one of the most advantageous times for me. It set me on a path to buy real estate, and if I was making the money I wanted to be making and could have bought the house I wanted to buy, I would never have found real estate. So I am so glad to have gone through that.
I want to always share that if you are in that place, this is potentially your competitive advantage, because I found a level of desperation that pushed me into action that none of my friends had. They bought condos or a house they couldn’t afford to furnish. And that duplex is one of my highest performing assets to this day.
Yes, the idea of necessity being the mother of invention. I think it’s because, like you were saying, you felt that shame. It’s really an emotional situation when we’re in that necessity that allows us to get outside of our comfort zone, that allows us to do that big scary thing like buy and renovate a duplex. Love that.
Yeah. And the safety of mentors who have gone before you, holding your hand. I think all of those things, and a good dose of naivete.
Yes, real estate investors do tend to be an optimistic bunch. We tend to see the best in everything, or what’s possible. Now you have this great portfolio, it’s given you this financial freedom. Talk a little bit about what your lifestyle is now based off of the portfolio that you have.
The portfolio’s very stable. It really hums along very well, especially because when I started doing midterm rentals, I recognized that I needed to start doing a lot of automation, otherwise I was just going to drown. So that has become, even though it’s a heavy labor-intensive process, almost the more hands-off part of my business, which is great. Now the portfolio has given me time freedom, to spend my time the way that I want. I mentor others on how to get to this point as well. It’s given me geographic freedom. It’s cleared up my head space. My rentals are running very well, even without me being there. I live in Connecticut, but I’ve been able to spend my winters in the southeast. I go down to Savannah. The first year was three months, the second year was seven months, this year was five months. So we’re kind of back and forth. Before that I was in the Caribbean for a couple weeks.
That really is what I think the most important part of real estate is. You get into real estate for passive income, the ability to do what you want with your money and your time. Then some people give their income to a property manager, so they’re really reducing their income, or they self-manage, but they’re doing every part of it, and it’s not really passive. Your own choices destroy either the passive or the income part. So it’s been very important to me to drill down, and thankfully I’ve had the time freedom to work on the business to make that a priority. Now that’s kind of snowballing more and more, and I’m able to share that with others, which has been such a great joy. Letting people see the aha moments I bring, like this is a great tip to use, or have you considered this strategy. I really love those conversations.
Now I know your life wasn’t always this free. Can you take us back before you got all these things optimized? When you had the doors but you didn’t have all these systems yet? What did your day-to-day actually look like then? And what finally made you say, I cannot keep doing this, I need to get into automation, into AI, build better systems?
There have been a couple turning points that pushed me further along. The one that got me into automation, at the beginning, was when I started buying midterm rentals. You’ve got a lot of turnover, a lot of inquiries coming in, lots of requests, all the things happening in quick order, over and over and over. I have a personality that cannot do repetitive things, that’s actually in my personality reports. Cannot do. I think that’s amazing and totally accurate. I’ve tried to tell my partner that also includes things like dishes. Cannot do repetitive things, but thankfully he understands that. So I really started to look at automation with an eye towards furnished rentals.
Once I put in place the concept of customized automation, you can choose to send out a message to your cleaning crew that they’re needed on this day, but the message itself actually changes because what they need to bring differs from unit to unit. You can do that if you build out automation. That’s the piece I was really missing and needed. Once I was able to make customized automations, my processes got so much better. That was really from the E-Myth, honestly, of how do you make whatever you’re doing the same over and over. But they can’t be the same over and over when things are different. So I went back to the philosophy of how they can be the same over and over, even though they’re different. Customized automation was a big one.
Then when I started to get into AI, in the past year, year and a half, AI has just exploded. There have been a couple ways, but it’s just such an intuitive tool, so thoughtful, honestly. There was a moment where I was boarding a plane, in line, and I got a maintenance call for no heat. I had to step out of line. I had to make a very big decision, can I actually handle this call, find a vendor, or do I just go on vacation and let them figure it out, which I couldn’t do, I’m not going to do that to my tenants. I stepped out of line, I was able to figure it out, but it was super stressful, and it just sent me thinking, and I realized that AI actually does a very good job of understanding maintenance problems. That sent me down a whole new path of conversation with automators and developers on what could be built that uses the intelligence of AI, but doesn’t require me to pick up the phone necessarily. It’s a combination of automation and AI, which is actually what a lot of my processes are.
I think that’s very intriguing. Let’s talk more about this tool that you built. Did you miss your flight then?
No, but I was the last one on the plane. I was very sweaty and grumpy for at least two days. I was worried, hoping the vendor got there, not sure what they were doing. Now I’ve got to make calls to find out the status, and I’m on vacation. It just really cut into my life. And it’s not that I was getting tons of maintenance requests, because at 19 units I don’t have tons of them. They come in waves, when they come, they come all at once. But I don’t have tons of them. I always have exposure to one inconvenient maintenance request. That was the day I decided that I do not want to be the person who gets the call. My other options I didn’t think were very good. You have a staff that handles it, and do you have gaps in coverage? Because it always happens on a Sunday or after hours. I really wanted something that was going to be very consistent, always on best behavior, trained as if it was a maintenance tech for twenty plus years. What’s incredible with AI is it can be a plumber of 20 plus years, or an HVAC tech of 20 plus years, or a handyman of 20 plus years, and you can have all of those people in one tool.
I love that. Now for the investor who’s skeptical, maybe even a little tired of hearing about AI, what is the honest, practical case that you make?
I get it. I’m also an AI hopeful and an AI skeptic at the same time. I love what AI promises, and I’m also very wary of the consequences if it doesn’t do it well. We’ve built a tool, and the tool’s name is Pam, Pam AI, just to put that out there. We like to call her by her name. With Pam, we’ve put in place tools or guardrails for the skeptic. I think it’s important that humans still have some oversight into what the tool does. There are some products out there where once the decision is made, it just runs with it. That terrifies me, honestly, because what if it makes the wrong decision? What can I do? I know my property better than anybody else. What if I just know that’s not the right conclusion, or that’s actually not the vendor I want to send for this one thing? With Pam, we have built-in grace periods where for every ticket you can look at the decisions of who’s been called, or who’s in queue. Do you agree with that? Do you want to change it? And which types of vendors can be chosen too. You can make decisions, you can override all the decisions, and you can set the policies too. Not just within those 15 minutes, but even afterwards, let’s say you missed the grace period, you can change it later. I think it’s helpful that you have a grace period, that nothing happens. If you don’t look at it, it’ll still run. But if you do look at it and decide you want to change something, you can do that. That’s really a big thing, finding tools that don’t assume they’re perfect, that recognize you still want some control over these tools, and that accommodate that.
I feel like when I think of AI, sometimes I go back to my childhood watching the Terminator movie, and based on what you just said with the grace period, I feel like you might have been doing the same thing, let’s make a Terminator-proof AI tool.
Yeah, exactly. There were a couple times where we’d run the ticket, and we’ve done over eight hundred tests at this point. I’d be watching to make sure the decision was right, and just wanting to know that if it wasn’t, I had some say in that. I’ve just seen the other option, like what if it doesn’t, and then are you stuck with it? Where’s the kill switch? So I wanted to make sure you had the option of changing it and putting it on the right path. Once you put it on the right path, it can run again.
Right. I like that, one of the things, using AI like Claude or anything like that, you’re a little off on my brand voice, or a little off on this, so let’s get you on track, and then you can use it a hundred times or more before the world evolves, you evolve, and you want to tweak it a little bit again.
Yeah. I don’t use it, it’s not a tool that I use at all in my runs, but it’s a tool I know that I have. It’s also a way to know, if we see that you’re having to override decisions over and over and over, we know there’s a problem with your settings, that you haven’t set up your vendors in a way that’s getting the results you want. We want to have a conversation about that, rather than you just having to override it every time. Again, we’re not seeing this, but this is a fail-safe we could put into place to make sure customer success is a top priority.
Now I know we’ve talked about the specific aspect. Let’s back up, can you give an overview of Pam AI? What I understand is Pam AI helps with maintenance requests, and it does it automatically, so the owner doesn’t have to be in the loop, but they get a chance. Can you fill in the gaps, for our listeners who aren’t familiar with Pam, tell us what it is as a whole?
It’s an AI-driven maintenance coordinator. It’s handling the front lines for every maintenance call for landlords. That includes emergency calls, routine calls, kitchen door coming loose. All calls can be run through Pam. It handles everything from ticket intake to diagnostic conversations with tenants. It will get to the most likely cause of the problem, attempt remote resolution, because our best case scenario is that we don’t have to send a vendor, that we can actually have the tenant self-help and solve the problem themselves. We’re going to do remote resolution efforts, containment of damage if we can’t solve it. Then Pam is going to use the landlord’s preferred vendors and do a vendor selection process. They’re going to look for existing coverage, warranties, service contracts. If you already have pest control on that property and an ant problem gets called in, we want to call your pest control company that you’ve already got contracted. We don’t want to call the other company that you’re not paying. And as if there’s a superintendent on the property, so your existing coverage is going to go first. If you don’t have any of that, it’s going to go into the general pool, and we look at all the types of vendors that could service the issue in the most economically viable option. If you were to just use a chatbot and say I have a clogged toilet, what should I do, it’s going to say call a plumber. We have had so much training of this tool to say you are not to jump to a plumber, you are going to go to a handyman, and if not a handyman, you’re going to go to a drain tech, and if not a drain tech, then you can go to a plumber. We’re going to do everything we can to send out the most cost effective vendor in your database that can service that property.
In this conversation, it’s apparent that one of your core values is preserving cash flow. That’s what it sounds like.
I have so many things I want to do with that money. I don’t want to be giving it away to bad decisions.
Yes, and that’s a good way to put it. I love that. Now thinking through this, what does the follow through look like? Because one of the challenges I know I face sometimes with properties is a lot of these vendors don’t answer the phone, don’t get back, don’t get out there for a while. They’re really hard to deal with, like a plumber in this example, or the handyman or something. Unless you’ve got your go-to that you have an established relationship with, it can be tough. So how does Pam handle dealing with the fact that these people, these service providers, are typically overwhelmed, understaffed, and more expert in their trade than in being a business person?
The first thing that we do is Pam sends a message introducing herself before a ticket’s been created. She sends a message saying, I’m Pam, I’m the maintenance coordinator for Stephanie Cabral, Sunrise Real Estate. Please save my number, you’ll be hearing from me. The tickets are time sensitive, if we don’t hear back from you, we will give the ticket to another vendor. My vendors save that number, so right then and there they know who that person is sending them the message. In the policy settings, the landlords can choose, based on three different urgency levels, how long of a window they want Pam to wait before hearing back and moving to the next vendor. Also what’s the earliest contact time Pam can contact a vendor, what’s the latest contact time. For emergencies, the default setting is 24/7. You might have business hours only for the medium level and low level. From there, if the vendor doesn’t respond, it’s going to send out a message to the next vendor in queue. It’s going to leave the ticket open for the first vendor to respond because they’re your preference, so you want them to still get back. But now it’s kind of an open ticket, and first accept is the one who gets assigned the ticket. We don’t pass along the contact information until the ticket’s been accepted and secured, so there’s no confusion about both accepting and both calling the tenant. We really keep that close to the chest. We’ll share the address so they know where it is, if it’s something they can service quickly. We also share the expectations. Those policy settings suggest how quickly you’re supposed to contact the tenant, how quickly you’re supposed to service the tenant, and those are passed along to say these are what’s expected if you take the ticket. If they take the ticket, those are communicated to the tenant, and the tenant will also get notification of who’s coming, who’s going to contact them. The vendor contacts the tenant directly, so you’re kind of out of the process, but you’re seeing the status, and you’re able to see that it’s been closed out. You can guarantee that if the vendor did not communicate with the tenant, you will know about it.
Because the tenant will let you know.
The tenant will let you know. We encourage that gently, like we’re alliances here. If you don’t hear from them, let us know. It’s not tattling, we’re on the same page, this is what’s expected, if you don’t hear from them for whatever reason, let us know. So there’s built-in checks and balances there.
I love it. When you build a system like this that’s going to run, you have to think about that flow, and part of creating that system is making it optimal, which you don’t do in the moment. When you were having to step out of line, from boarding a plane, you weren’t setting expectations and working through your ideal list of vendors. It wasn’t optimized or ideal, it was reactionary. But now Pam can be optimized and ideal, it sounds like.
Yeah, absolutely. I was literally just taking whoever would go, because I needed to get back on the plane. The first person who could confirm for me verbally, I was going to accept, versus knowing there was going to be a process that would run, and I would be notified if nobody responded. If you’ve got a good Rolodex of vendors, you’re going to get a response. What I’ve actually found, this is interesting, is that now because my vendors, I’ve seen this with my electricians a lot, I’ve got a bunch of them that I use, one go-to but a couple in the mix, and they have missed their window, and now they will text me and say, darn, I missed the window, I won’t do that again. I have been surprised at the psychology behind the lost opportunity. I do think that over time you’ll start to filter out and want to change and play with your vendors, but I will say my handyperson, that ticket goes out and is accepted within 10 minutes every single time.
I think that’s a really good point. Some of these things speak to the psychology of it too. So often as investors, we can feel a little bit at the mercy of these contractors or service providers we’re using, and you’ve really taken the tool, taken back that agency, taken back that control, because you’ve got a system, you’ve got a list of people, you’re no longer at the mercy of that vendor. It’s pretty cool.
Exactly. If not them, it’ll be somebody else, and there’s a list of them. I’m okay with all of them.
I love it. Now, Stephanie, if people want to connect with you or learn more about Pam, what’s the best place for them to reach out?
Go to the website, choose pam.ai, and you can also follow me on all the socials, Facebook, Instagram, the ending is Stephanie Cabral, and then my personal page would be thestephaniecabral.com.
Awesome, fabulous, thank you so much. And for our listeners, that is a wrap on today’s episode. If you got value from this conversation, please do me a favor and subscribe wherever you’re listening, it really helps us out. Join me again next week for another episode. I’ll see you then.