I sat down with Akshay Bajaj, a former AI engineer who spent over a decade building systems for self-driving cars and aircraft autopilot before turning that same expertise toward his own short-term rental portfolio. Akshay walks through the exact moment he realized property management had the same core problem as the robotics he’d spent his career solving, and how that insight led him to build an AI system that handles guest messages, vendor coordination, and dynamic pricing while knowing exactly when to hand a decision back to a human. We get into why most property management AI is really just glorified auto-replies, how his platform’s “ask before act” approach protects the guest experience, and where he thinks the short-term rental industry is actually headed over the next few years. If you’ve ever felt like self-managing a rental gave you cash flow but took away your time, this conversation gives you a real framework for getting both back. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

I’m Adrienne Green, and today we’re here with Akshay Bajaj. Akshay is a great example of someone who broke free of the grind, and he’s made a tool to help everybody else do that too. So I’m excited here. Akshay, thank you for joining me.

Thank you for having me, Adrienne.

Before we get into the tech stuff, can you start by giving listeners a quick picture of your real estate background? Because you’re not just a tech founder, you’re an investor yourself.

Yes, that’s how I actually started. I was in tech building AI for more than ten years for robotic systems, not for real estate at all. But while I was doing that, I also started my own Airbnb, because in my own journey I found that freedom is the most important thing to me. And the first way I could actually start comprehending how to get freedom was financial freedom. So I started investing in real estate, living in Las Vegas, the hospitality mecca of the world. Thought it’d be great, and actually it went as planned: 92% occupancy and more. I kept increasing prices, things were going good. And then I scaled up to quite a few listings to actually get my freedom back. That’s how I experienced it, because when you start as a new Airbnb short-term rental owner, it’s deceptively taxing. We don’t realize how many small things go into not just the day to day, but also the setup of the listings and finding the listings. So I found all of that out myself, learned the hard way.

Also, just for background, my dad, although being a doctor, has been in real estate his whole life. He’s a developer, and growing up as a kid I helped him out a lot with his real estate business. So I know how the entire thing is built and all the small things that go into a property. And I’m a big believer that there’s a difference between a house and a home, and making every house a home.

And of course all the other things that go with it.

And I think we’ll get into a lot of it as we go through here. I had the pleasure of actually meeting and speaking with Akshay last week, so I know he’s got a lot that he thinks about, kind of like me. I think you think about every piece of the puzzle and it all fits together nicely. But if we get back to the cool thing you developed here: you were in your W-2 job working for someone else, working on the software for self-driving cars, for aircraft autopilot, and you applied it to vacation rentals. But as a vacation rental or short-term rental owner, what were you seeing on the operation side that made you think this is the same problem I’ve been solving on the tech side, and I could solve it here in the short-term rental side?

Absolutely. I actually gave a talk at UNLV, and the title of the talk was basically the same, which is “Are We Living Inside a Robot?” Fun fact, we still have not come up with a perfect definition of a robot that everyone agrees on. But in a way, the way we describe a robot is that it has actuators, which is like motors, arms, legs, whatever. It has a brain and intelligence, and it also has a way to sense things, which is what we call the sensing unit.

So I realized, okay, for aircraft, for self-driving cars, the things we’re controlling with the intelligence I’m creating are the final position of the wheels of a car, or a steering wheel. In this case, we have the same thing, but what we’re actually trying to manipulate or get control of is the people moving inside. Which is: when does a turnover happen? When does a guest come? What is it that we’re telling the guests that will allow them to have an experience like we want them to have? In our case, the intelligence was missing. There’s no real estate platform which has any kind of built-in intelligence that allows this to happen autonomously. We have workflows, which is what we try in our stack: hey, at this time do this, at this time do this. But whenever you have anything that’s workflow-based, you’ve lost the human touch. It’s not organic anymore. It’s not calibrated to you anymore.

That’s what I found: in a way, it’s the same problem, just the actuators are different. If I build an intelligence layer that has control over the things, it would be great. And the other examples of actuators would be the house temperature, the lock codes, the jacuzzi being on or off, the recommendations we give guests. And that is how, when I thought about the problem like that, all of a sudden a new world opened up.

Which is what now has become Host Easy.

So Host Easy is the name of the SaaS system you built. For people who are familiar with SaaS, but I know you like to call it something else.

Yes, it’s not SaaS, it’s FAS: Freedom as a Service. We are not software as a service.

Because you’re really about what you’re providing people, and that is freedom.

Exactly, because that’s what happened to me. Imagine, at one point I had about twelve listings. Eight to twelve, some were owned, and then I was controlling and managing about thirty-eight. Even at six to eight listings I realized I had no freedom at all. Because I wanted to treat my guests as God, as we say in India. I really wanted to give them a great hospitality experience. I wanted to be available at three a.m. when they wanted to get in the jacuzzi at night.

But also, it was taking away from everything I thought I would want. And that’s when I realized: I do not want to compromise on giving my guests an immaculate experience, but I also don’t want to give up on having my own freedom back. How do I come up with something that allows for both? And that’s why we call ourselves Freedom as a Service.

I love it, and that’s such a common challenge in the short-term rental space. People do short-term rentals because they want increased cash flow, so they’ve got financial freedom. But then they find that if you self-manage to get that cash flow, you don’t necessarily have time freedom, because you now have to provide a lot of service, and that could be twenty-four hours a day. So you came up with Host Easy, Freedom as a Service, to help solve that problem. You can self-manage and keep that financial freedom, but it helps with a lot of the time pieces so you can get the time freedom you’re not often getting with self-managing. Is that a good summary? Am I understanding that right?

Yes, that’s one part of it. We do take over all the operations, end to end. So ninety-one percent of the work is done by AI.

But you don’t just get an AI platform like any other PMS. First of all, it’s a different PMS altogether. AI is literally doing the work for you, not just following orders. But you also get a team of people available twenty-four-seven, not just for the guests but for you as well, within five minutes, taking care of the nuances whenever something goes wrong. So you really can be hands-off if you want to. But the other thing is, because AI is so good at data collection and processing data at a tenacity humans can’t, it also gives you financial freedom in the sense that sometimes listings aren’t going to make as much money. So Alfred also changes your strategy for pricing, for minimum stay, everything, like a revenue manager does. On top of that, it gives you a prediction of what you’re going to make in the future or not. So when you look at it, you really know whether this listing is going to give you financial freedom or not, while it’s managing it. And then it also takes over the operations to give you the time freedom, both in a single package.

Okay, so walk us through what a well-automated short-term rental operation actually looks like day to day. If somebody’s using Host Easy, they’ve got Alfred, who’s not a real human, but they also have VAs who are real humans on the back end. What’s the AI handling, and what’s staying with a human?

Alfred is really good at doing anything monotonous. It never sleeps, never forgets. So you don’t need to create a property guide or SOPs or anything like that. Alfred already knows the best ways to manage things. It learns everything from your listing. It actually analyzes every photo and looks at every amenity you have, and when it doesn’t know something, it asks you questions during onboarding. So now it has a full picture of what’s going on. It also talks to the cleaners, talks to the vendors, as well as handling your pricing. The only thing Alfred does not do is handle something that’s an emergency. It will notify you of the emergency, but rather than just handling it, it will message the guest to de-escalate, but it will let you handle everything else. It will give you a suggestion, because we understand that’s when the human touch is needed more. Any kind of nuance where it feels uncertain about information it doesn’t have, it pings the team or you and says, hey, I’m not sure if we have a baby grip. Before I reply, can you confirm?

And either you can reply yourself and Alfred remembers, or you can tell Alfred, yeah, we do have a baby grip, and it remembers forever. So it’s very accurate about knowing what it can do, but more than that, it really knows what it cannot do. And that’s our goal. Ask before act. That’s what it always does.

That’s a really good point, actually, because I know when I use Hospitable on my properties, I’ve used it for a year or two, and I have all their AI tools turned off. Whenever I try the “answer with AI” function and it drafts something, I usually think that’s wrong, so I don’t use it. I’ll use the “improve with AI” function where I write the facts and it makes it sound nice, but that’s still very labor intensive for me or for my VA.

Because if you think about it, you have to be on call. At two a.m., if you still have to improve the message yourself, you’re not hands-off. That was my main problem with these tools as well.

Right, especially when you have thirty-eight doors you’re managing. You could just guarantee something’s going to go wrong every few days with that many doors.

And that’s why we architecturally built it entirely differently. I’ve been building AI for more than a decade, since before AI was a mainstream thing. I know how to build a cutting-edge AI. It needs three things. For an AI to be like Alfred, it always passes tuning tests. A tuning test means you can’t tell whether it’s AI or human, and it’s not by chance. The way it works is that AI can only be as good as its access to three things. One, how much access to real-time information it has about everything.

That’s why we built a unified platform where Alfred knows about the last cleaning that happened, the last maintenance that happened, access to lock codes, access to the knowledge base, listing info, everything. It knows everything about everything, and that’s in real time. The second thing is how good the training is on that particular thing. That’s why we have human in the loop. It’s trained on industry-specific, hospitality-specific data. And then the third thing: now it has all the intelligence, all the training, and all the access to what’s going on. What it can do with that is integrations, and that’s why Alfred has access to the door lock. When a guest is locked out, it looks at the lock code, and if it’s not working, it unlocks the door, creates a new lock code for them, and sends it. This would be impossible for any other system out there, because they’re not unified like that. It actually contacts the cleaner or a handyman, because it can call them.

And message them and say, hey, can you please help out with that, based on the instructions you’re given. That is how it becomes a very different experience altogether. And that’s why when you look at Hospitable or other hosting companies, I see them as more of a glorified quick reply system. You’ve told it, for this situation do this, do this, do this, and then AI is doing “improve,” sending it based on the last thing. I don’t think that’s scalable.

No, and that’s where listeners who have short-term rentals and maybe got burned by the AI built into these other platforms, because they just do auto replies. You set up: when somebody messages about early check-in, send this message, but then it sends it when it’s not appropriate. Yours is a totally different, much smarter system. Now, Akshay, you said if there’s an emergency, it pings you. You also have an option within your program where somebody can have the AI and a VA on your team. Who’s helping with that person piece? What stays with the person piece?

We have something called supervision mode. If you want, you can turn on supervision for guest messages, vendor messages, or any action you want. You have full control. If supervision is on, AI knows what it’s going to respond, it drafts the message, but then waits for you, or our VA team, to accept or decline. When you accept, the message goes out as you, not as Alfred. If you decline, you or the VA rewrites it and sends it from there. That is the idea behind having a VA in the loop, human in the loop. On top of that, there are also actions. We don’t just do messages, we also handle day-to-day tasks, and that’s also our team of people.

We also handle guest disputes. We manage guest disputes for Airbnb and VRBO, and we’ve done it more than 10,000 times now, so our success rate is very high. You get all of that with one subscription, because to be honest, we don’t have the margins to give twenty to twenty-five percent to a property management company. You get all that work done as a flat fee model, like a SaaS software.

So it sounds like, and correct me if I’m missing pieces, Akshay, with Host Easy, whether you have it fully automated or you’ve chosen the human in the loop supervision mode, you’re handling all the day-to-day management of the property. Coordinating the cleaning, maybe a handyman, messaging guests, dealing with disputes. What are some of the other pieces that I as a property manager would still have on my plate? So my personal property manager VA would still be coordinating my twice-yearly HVAC inspection, correct?

Yes. There are certain actions, and the idea is that one action you set up is, say, twice-yearly HVAC inspection. Alfred will still trigger it, but you can assign that action to your VA. So it automatically comes to your VA’s desktop, your property manager. This action needs to be done. And that is how we go about it.

Awesome. So the nice thing being taken off the plate is the revenue management, optimizing the listing, handling all those guest messages, helping problem solve how to use the Roku TVs. Am I the only one where about once a month a guest doesn’t know how to use the TV because they’re used to cable? Those are the kinds of things host handles.

Yes, we also help with guest disputes, damage claims, coordinating with the vendors. When there’s a crisis, that’s the only time we don’t take decisions on your behalf, meaning how you want to handle the crisis. That’s where either a property manager or you would be there a hundred percent. We would still handle the back-end work, like communicating with guests, coordinating with the Airbnb support team. But you have to be the one actually calling the maintenance person and scheduling them. Once the schedule and payment are set, we continue with the coordination.

And what I love about this, Akshay, is I’m all about leveraging technology and a team. What I love is when technology can help a team do a better job or go further faster. So if somebody wants to work with a company like Workergenix and get a virtual assistant to be their property manager, they can partner that VA with something like Host Easy, and Host Easy can handle a lot of the day-to-day communication. The virtual assistant can handle the bigger things. Right now my VA is handling getting quotes on new HVACs, because HVACs on oceanfront houses in Myrtle Beach die in about six to eight years. Ask me how I know. That’s something my VA, the property manager, can handle better, faster, and easier when the day-to-day guest messaging is off his plate with something like Host Easy.

You’re absolutely correct. The nuances would always be there, to be honest. One more thing we’ve done is try to make the VA’s life easier as well, because I realized there would be days where everything across all the listings goes down at once, and that’s when the overwhelm happens and bad reviews come in. The way we’ve addressed that is we created something called Playground. It’s a tool set. So rather than a VA finding, say, an HVAC person manually, they can ask Alfred on the Playground, hey, can you find me HVAC people, and it gives a list of five to ten people. Now they can call, coordinate, and do the same work faster and more accurately. Same goes for finding other collaborators.

I love that.

And then we made inviting those people faster. You click invite, put the information in, and coordinate fast. That’s how we’re trying to streamline every single thing I personally came across as a property manager myself. The other thing is finding a good VA. That’s a very important problem as well, and that’s why we’re doing this partnership where you’ll soon be able to find a vetted VA literally on Host Easy. They’ll be VAs who are vetted by us, highly certified, incredible at what they do. No need to train them or teach them what needs to be done. They already know everything. You just do a vibe check interview if you like, and there you have a VA.

Yes, because if you talk to a few real estate investors, you’re going to run into a VA fail. For every five investors you talk to, you’ll probably hear at least one VA fail story. So as much as I’m passionate about helping investors lessen that, it’s a learned skill.

And also, you would know already how difficult it is to tell one good VA from another, because it’s the culture they have to understand, very intangible, beyond just the skills themselves.

That’s a very good point. There’s a lot that goes into it. Now, thinking about the automation piece, one of the fears people often have when we talk about automation and AI is the loss of guest experience. You’ve got Hannah the host, who thinks there’s no way Alfred the AI can provide the same experience she can, and she’s afraid she’s going to lose her five-star Airbnb rating if she uses this system. How do you think about protecting the human side of hospitality while the AI is handling the operational load?

To be honest, Hannah could be correct, because the way Hannah curates an experience might be very exclusive to her and her property. That’s why we give full control. If Hannah loves guest communication, she can turn that off for Alfred and let Alfred handle everything else. The good thing is, every time she’s doing guest communication, Alfred in the background is always learning. It’s learning how she talks, her communication style, what she says for different things. So if tomorrow she wants to go on vacation and turns it on, she knows Alfred is as in line with her as any system out there could be. Or she can turn it on with supervision mode, and in supervision she can make herself the supervisor instead of our team. Or if she wants more trust built first, she can make our team the supervisor. If she feels comfortable, she can turn off supervision mode. So you can go through it in baby steps, full control, and full transparency, because everything happens on one system, so she can see what happened. That’s how it becomes valuable for anyone getting into it.

And in that answer, even though we’ve spoken before, I learned something new about how your system works. What resonated with me is, as a former teacher who’s also in the virtual assistant world, half of the job is training the client, the employer, how to work with the VA. One of my main frameworks is I do, we do, you do. And that’s really what you’re allowing to happen with your system. I do is like Hannah turns it off and does it herself, but Alfred is monitoring and learning. Then there’s we do, with supervision mode, where Alfred is doing some things and she’s supervising. And then there’s you do, where she has trained Alfred and he can run on his own. That is a standard teaching model for handing off control, and you’ve built that into your system.

Absolutely. That’s why we say we’re not an automation platform, we’re a symbiotic platform. Humans and AI together doing the work for you, end to end, twenty-four-seven. And Hannah might not like numbers, let’s be honest, so give Alfred the dynamic pricing, give Alfred the revenue management, maybe the turnover.

You can hand that to Alfred. Because at the end of the day, what is hospitality? Hospitality is serving the people who are guests. So I want to serve, and I have my own idea of how I want to serve them. I don’t want to take that away from you. That’s the thesis Host Easy is built on. We truly make hosting vacations easy. Host Easy, that’s the idea.

At what point in a portfolio does it make sense to invest in a platform like Host Easy, Akshay? Is this a tool for someone with two properties, twenty, or two hundred?

We don’t look at it in terms of how many properties, we look at how much freedom you want. We have hosts who just don’t want to do anything. Right now their only option is giving fifteen to twenty percent of revenue to a property manager with no transparency, no visibility, no control, because they do it their way. Instead of that, you can use Host Easy, fully managed, and there you go.

Or we have property managers with thirty, fifty, eighty listings. They really need something like that, because they’re running what we call a Franken Stack. Now you have one tool for finding cleaners and paying them, another for ticketing, a PMS for channel management, another for dynamic pricing, another for guest verification, plus Notion, Google Docs.

Yes.

Passwords, training VAs, all of it. Everything is on one platform, and they love that idea, because once you’re past twenty properties, it just makes sense. Everything is here, Alfred is in the center, and I just tell Alfred and it updates everywhere. It’s a different experience.

It’s funny you use the term Franken Stack, because the very first place I ever heard the term “tech stack” was at a short-term rental conference. This guy got up and said, I’m going to share my whole tech stack, and I thought, what’s a tech stack? Then he started sharing all these tools he uses.

That’s a lot. That’s how a lot of short-term rental operators are in this space, and it really is a Franken Stack. Then the connections between tools break and stop working, because one of them updates and you have to redo the connection. I feel like any short-term rental person listening probably has some experience like that.

And not even just the connection. Forget about having ten logins, we can make do with that somehow. But imagine all of a sudden you want to take the pool off your listing because it’s too much hassle. Now you have to change it in your quick replies, on Airbnb, remove the amenity, then in your property guide, then in Notion because that’s what your VAs use. You have to change it everywhere. And still, you don’t know if something is missed. Your VA might say one thing, and something else might be listed elsewhere. Your vendors might know a different thing altogether. It doesn’t scale like that. Here, because everything is in one spot, in our case, Alfred, we don’t do pool anymore, update everywhere. It updates the listing, updates the knowledge base, tells the guest the same thing, tells the vendor the same thing, and it also updates pricing, because now it knows that’s not one of the amenities you provide anymore. It becomes super simple.

I love it. Now I’m curious, Akshay, because you’ve got your ear on the ground in the short-term rental space. With this asset class, what do you envision for how it’s operated and run now? This space has changed a lot since 2019, 2020. It got pretty hot, we’ve had some markets go up and down, but the key question is, three to five years down the road, what do you think the market and the operations ecosystem will look like?

I believe the ecosystem is finally going to look like the way we always imagined it, which is: the more human experience you can create, what we call high touch in hospitality, the more you’re actually going to get the earnings. So it’s not about automation anymore, it’s about how much human experience, how good of a custom curated experience you can create, how tailored you can be.

That’s what we’re doing with Alfred and Host Easy. Because it has full control over every single part of your house and your listing, we want to allow it to create an experience for your guest that would be almost impossible for us to do at scale otherwise. And that’s what I believe the ecosystem is going to move toward. You’re already seeing that. If you look at short-term rentals, there are properties worth 200,000 to 300,000 dollars that are making returns like 5-million-dollar properties, because it’s an experience. It’s a tent in the middle of nowhere that just looks a certain way, with some kind of guidebook. That’s how I see it becoming. And one thing I think a lot of people aren’t talking about, and everyone with a short-term rental should be careful of, is that Airbnb, the biggest marketplace, now also shows hotels. So you’re not isolated anymore. You’re actually competing with fifty-dollar-a-night prices. What can you provide? It’s a very specific kind of customer you’re looking for, so you have to position your property accordingly.

I think we have to point out that the guy who’s here with his AI-forward solution thinks the future of short-term rentals is high-touch, curated human experience. And that so much resonates with what I see across the board, where in all these different industries we’re seeing people crave human interaction, face to face, as real life as possible, so we know it’s not fake, so we know it’s not AI. My kids are better than I am at spotting AI on Instagram, saying that’s AI, that’s AI. It’s tricky now, but people are craving those real, authentic experiences that aren’t contrived, and what I love is how you’re using technology to facilitate that human connection and great human experience.

Yes, absolutely. I truly don’t think you should use technology unless it’s needed. Although I’m a technologist myself, I believe in experience first. We are the most human AI company. It was actually a big deal as a new startup to take a stand and say, we’re going to provide a human team as well. Because the whole point of SaaS is, why would a company run humans? Because humans reduce your profit margins and your scalability. But we’re like, no, if you want to change the world, start by changing a house. You want to make a world that’s more experience centric. Let’s start from where we’re going. And if you can create a great experience through human connection, it will pay dividends. That’s how I believe.

So Akshay, if people would like to connect with you or learn more about Host Easy, what’s the best place for them to reach out?

You can go to our website, which is hosteasy.ai, and you can sign in and onboard your property yourself. Alfred will help you onboard the property because it learns everything about your listing the moment you add it as a co-host. Or you can set up an onboarding call, and we do all white-glove onboarding end to end at no extra cost. If you want to get in touch with me, I’ll share a LinkedIn link. Happy to connect. Any ideas, let us know. We’re always listening first, trying to know what your pain points are and fixing them for good while maintaining the experience. That’s our goal.

Love it. Well, thank you so much, Akshay, for coming on and sharing your experience as a short-term rental investor and how it prompted you to develop Host Easy and solve all the problems you had. And for our listeners, that is a wrap on today’s episode. If you got value from this conversation and you know somebody who needs Host Easy, do me a favor, do Akshay a favor, and send this episode over to them so they can take a listen or a watch. And join me again next week.

The post How Much Automation Is Too Much in Short-Term Rentals? appeared first on Adrienne Green.

I sat down with Tim Kelly, a commercial real estate investor who scaled from residential deals into multifamily apartment buildings and mobile home communities through partnerships and joint ventures, and this conversation is one I think every stretched-thin real estate entrepreneur needs to hear. Tim shares the exact decision-making framework he uses under pressure, the four things a process needs before it’s actually ready to delegate, and the moment he realized that being good at doing the work was the very thing keeping him stuck. We talk about discipline, identity shifts, and why delegation without clarity is just dumping a task on someone else. If you’ve ever felt like your business can’t grow past a certain point without you personally holding it together, this one will give you a real framework to work from. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Hey everyone, welcome back. I’m Adrienne Green and today we’re here with Tim Kelly. Our listeners know we focus on how real estate entrepreneurs break free of the grind and create the freedom they really wanted at the start. And Tim is a perfect example of this, so I’m excited for you to be here and share your story with us, Tim.

Adrienne, thanks so much for having me. I’ve been looking forward to our conversation, and it’s an honor to be here.

Awesome. Well, to set the stage for our listeners, what does your real estate portfolio look like today?

So, quick version: started like a lot of people, thinking small, in residential, and then I got exposed to bigger rooms, bigger conversations, and bigger possibilities. Today my background is mostly in commercial real estate, so multifamily apartment buildings, mobile home communities through partnerships, joint ventures.

And then I really leaned into helping military families understand how to move from trading their time for money into building assets, because I started my journey when I was active duty. The biggest shift wasn’t the portfolio, from residential to commercial. It was truly first an identity shift, and commercial real estate entered the picture for me.

When I was active duty, around ten years in, I got this bug. I had to free up my time, but I mostly focused on apartment buildings and mobile home communities.

Awesome, that gives us a good picture. And what I love that you’re teasing there with the identity shift is the idea of be, do, have. In order to have, we first have to change who we are, that identity shift, and then that changes our actions, and then that changes our results. So we’ll get into that, but let’s ease our way in.

I would love to go deeper. But yeah, it’s so important, so important.

Let’s start at the beginning. I know with your military background, we can see the sign for those who are watching on YouTube with the video: Discipline equals freedom. You talk a lot about discipline as a tool, and it’s not just a trait, right? It’s something we’re actively using. What does that look like in the day-to-day for you running your real estate business?

There’s a reason why that sign’s up there. Discipline is not just wake up early and grind. There’s a lot of misconceptions around discipline, and that’s how a lot of people, especially high performers, high achievers, burn themselves out. To me, discipline is the ability to keep promises to yourself when the emotion is ramped up.

In business, that looks kind of boring. It looks like making the calls when you don’t feel like it, and reviewing the numbers one level deeper when it could be easier to avoid them and assume the rules of thumb apply. And having the hard conversations before resentment builds. That’s such a big one, especially the personal conversations. So many high performers could have those bold, courageous, difficult conversations. But ultimately, discipline is following the system instead of chasing every shiny object. And I think again, people confuse discipline with intensity. That’s easy for a few days, but it’s consistently over a long time horizon where the results will just show up, when you don’t even really expect them.

A lot of people correlate discipline with a restrictive thing, less freedom. But it’s actually the complete opposite. It says discipline equals freedom. When you have actual discipline, Adrienne, it’s simply the structure and system that you’re able to put in place in your life to give you the life that you want. So if you’re listening and you’re engaged here, I ask you: what are you depending on motivation for when you actually just need a system? That’s where discipline becomes that tool.

I think that’s so helpful. I know for myself, Tim, what really was transformational is when I started doing time blocking on my calendar and committing to that time blocking, like it’s an important meeting with someone important. And it gives you that freedom. I time block my working hours, and then when they’re done, it’s easier to have the freedom to go do other fun things, because I know I got my work done, because I had those time blocks that got done.

Time blocking’s been a game changer for me as well.

And a great example of the discipline. So along those lines of discipline, you do have this military background. I know that’s probably been a really important factor in shaping the way you handle everything. And what I love to talk about, because I know it applies to a lot of investors, is decision making under pressure. How does your military experience inform how you do that?

The military taught me a lot. Directly tied to this, it taught me that pressure doesn’t create your character, it reveals your level of preparation. In the Navy, especially in leadership and operational environments that I held, you learn quickly that waiting for perfect information can cost you. You still need to be able to assess risk. You have to gather data, listen to your team of advisors, but you can’t hide behind analysis forever. Think about how easily that correlates to real estate investing, Adrienne. It translates directly to it. A lot of investors get stuck because they want certainty before action. Analysis paralysis, we’ve all heard of it, but real estate doesn’t give you certainty, business doesn’t give you that certainty, life doesn’t always give you that certainty. What you get is information. You get your experience from taking action, and then you have to learn how to assess the risk, identify the downside, of course, but you make the best decision with the information available, and then you just pivot. Because of the decisions I was faced with, I needed a framework for this, and I created a framework.

This is for you to use when you’re faced with any kind of minor or major decision.

If you’re thinking about submitting the offer, or calling the broker, or calling that high net worth individual who has expressed interest before and has seven figures to invest, or even signing the PSA or signing the loan documents, those are big decisions. Whatever it is, the framework is this, and I want you to use this. Number one, you ask yourself: if I do this thing, what is the worst case scenario? And then you say, well, what is the best case scenario? And then you think, what is the most likely case scenario? That’s going to give you a realistic idea of probably what’s going to happen. And then you just count to three. Three, two, one, and you decide. Sometimes you need a little more depth, but in a quick way, I’ve used this framework so many times, where within less than a minute I can make that decision. What is the worst case scenario, what is the best case scenario, what is the most likely case scenario. That gives me a lot of perspective. Three, two, one, and I decide and I move. But sometimes you need to assess your resources. You have to assess five different things. You have to assess the amount of time, what is your timeline? A lot of times in real estate you’re on a timeline, you’re on a lender’s timeline, you have three days to submit the EMD, you have usually 60 to maybe 45 to 60 days of due diligence. How much time do I have? How much capital do I have? What does your team look like? What is your level of energy? And then how much knowledge do you have in this? If you really want to take it one level deeper, assess those five things, and you have to decide. The audience takeaway, if you’re listening, is this: confidence doesn’t come from knowing everything will work.

Confidence comes from knowing that you can respond well when it doesn’t. I love sharing this, because my mentor told me this one time, and it’s always resonated with me. You won’t ever see the top of the stairs until you start taking the first couple steps. You’ll never see the top of that staircase until you start taking the first couple steps. And the cost of you sitting at the bottom of that staircase is so much more than the cost of you taking the first few steps.

And making some mistakes along the way. Those mistakes are inevitable, simply part of the process.

Embracing imperfect action. That is okay, but we’re going to learn more than not doing it at all. And I love what you started off with there, about what’s the worst case scenario, because I see all the time, with all humanity, I’d say, not just real estate investors, we have this fear of failure because we think that failure, I mean, US American culture, really makes failure seem like you’re the worst person in the world, and they think, my gosh, if I fail at this I’m going to be homeless living under a bridge. And the truth is that often the real worst case scenario is not nearly that severe, if we actually think about it logically instead of just having our emotions take over.

Sure. You’ve likely already put so much into it. You’ve likely already have the right team assembled. You’ve likely got the capital assembled. But look, just like you said, Adrienne, our society programs us to be small, to be conservative. And that’s why it’s so important to be around people who think big, because if you isolate yourself, the part of your brain that wants you to stay small, not take risks, not think big, is going to negotiate with you and win. It’s going to convince you not to take that step, not to take that risk, not to think big, because of how our society is. We’re programmed to work for somebody, give somebody else the risk, do what you’re told, go to school, get a good job. It’s been programmed into us since we were born into this world. So if you isolate yourself, that part of your brain that’s inherent is going to win the negotiation with you.

Well, and that sets us off perfectly, Tim, to revisit that mindset shift that you experienced from when you started real estate investing, and you were thinking small, you were just an operator, maybe wanting a little bit of passive income, and you had that mindset shift you spoke about in the introduction, where you really became a leader, you thought bigger. What did that look like for you? And what wisdom would you give to listeners who are maybe still where you were when you started?

This is an easy trap for ambitious people to get into. The biggest shift for me was realizing that being really good at doing the work becomes the thing that keeps you stuck. As an operator, you get rewarded for solving problems. You jump in, you fix things, you make it happen. That works early on.

But if you keep doing that forever, you become the bottleneck. Leadership requires a different question. Instead of asking, how do I solve this, you have to ask, who should own this, and what system would prevent this from depending on me next time. That was a hard shift, because doing the work feels productive.

Leadership is not about being the hero, Adrienne. It’s about building people, building systems, and offering that clarity so the mission can move without everything running through you, getting your approval.

For the ones listening, I’d say this: if your business needs your constant heroics to function every day, you don’t have a business, you have a demanding job with your name on it. And I always appreciate a good book recommendation, so here’s one for this exact topic. Maybe you’ve read it, Adrienne. It’s Who Not How.

Not how do you make this happen, it’s who can help me make this happen, or who can I get to own this, as long as they have a clear vision. It’s not easy to let go of the vine. Some of us call it that: when you scale, you have to let go of the vine, because you’ve built this, and you have to allow other people to care for, nurture, and scale it. What you’ve put so much into, that’s not easy. But that’s next level leadership. The key with this, though, is to be able to articulate that mission and vision so clearly that you’re going to inspire others to join you. And that’s not leadership, that’s real influence.

I love it. And obviously I’m on board for this. I have a virtual assistant business, and I think so many people need to get out of the doing. And what’s cool is, with virtual executive assistants that we focus on, I’ve seen, Tim, when people do exactly what you’re saying, and when they’re successful, the cool thing is a lot of our virtual EAs haven’t had exposure, they’re not in a world where real estate investing has been presented as an option, a lot like with Americans as well. So it’s cool when you see these virtual executive assistants catch the dream and the entrepreneurialism from their clients. I know, for me, my executive assistant in the Philippines bought a business, a sari-sari shop that sells rice and other basic goods, and then he gave it to his parents to run. So they get income, they’re able to take care of themselves. That’s relatively rare in the Philippines, and it was cool to see that you can cast that vision, tell people, and share this idea of entrepreneurialism, and see it take root.

That’s such a great example. You can’t be the bottleneck, eventually you have to step away, but that’s not easy to do. It’s not easy to think through that type of decision.

So when you started scaling your portfolio, when you started to realize you didn’t want to be the doer for everything, what were some of the first tasks you identified to hand off? And how did you know when it was time to hand those off and level up?

That’s what really attracted me to multifamily, large commercial multifamily. Before I even got involved in real estate investing, I knew I didn’t want to manage properties, manage people, manage tenants.

The first apartment building I partnered on was a forty-two unit apartment building. Before that, it was a fourplex. I had a fourplex, I self-managed just to figure out the systems, and I quickly knew I was hiring a property manager for that fourplex, and I was never managing again. But then I got into the forty-two unit, and I thought, we’re good, we’re going to hire a property manager, everything’s going to be great, it’s going to be real passive income.

What we didn’t realize was that forty-two units wasn’t big enough to pay a full-time property manager, and the numbers didn’t make sense yet. So we were only able to afford a part-time property manager at the time. First, we hired the wrong property manager, a huge mistake, and they convinced us they were the right fit. That was one of the biggest mistakes. Then we realized we needed to find someone who could be paid part-time but serve the community well enough that it could still be profitable. That’s not easy, so we had to get creative with it.

It ended up being a home run, because she was a rock star. The person we hired as a part-time manager made it happen. But the huge lesson learned was that I never again joined a team or bought a deal that was too small, where we weren’t able to afford a full-time property management team. In most markets, 80 to 100 units, you probably have enough revenue to pay a full-time property management team.

And so that was the first thing. Learning from that, the bigger you go, the easier they are to manage, because you can hire a full-time manager, and the easier they are to finance, because you can get non-recourse debt. The bigger you go, the easier they are to manage, the easier to finance, and the less work they are. So I knew I didn’t want to do operations, I knew management was the first piece.

Once we got to that point, it was the bookkeeping. I’m not left-brain analytical, data driven. I’m never the underwriter. I’m more about connecting with the brokers to find the right deals, sharing the deal criteria, and then connecting with investors, getting to know their goals, and helping the team raise capital. So bookkeeping was the first thing I ended up delegating, because I really didn’t want to do that.

Nowadays you can have Claude Cowork bookkeep for you. You don’t even need to hire a bookkeeper anymore. You just talk to your tax advisor, to know exactly how they like to see all their data and financials so they can do your taxes for you, and then you tell Claude Cowork to run it. That’s kind of been my solution. I actually let go of my bookkeeper about a year and a half ago, because now AI can do it.

And I think that’s part of that delegation and getting out of being that operator, I always view it as the systems, the tech, and then the team. So you mentioned before the systems part of your discipline, the system that you run again and again, the tech, Claude, AI, all of those options, and then you have your team for the things the systems and the tech aren’t solving, like your property manager, your boots on the ground.

Yeah.

Love it. Now what does a well-built system look like to you? And how do you know when a process is ready to delegate to someone else?

For my brain, I have to use a framework, or you could call it my filter. First, mission. Second, money. Third, energy. And fourth, unique ability.

Is this thing that I’m spending time on, or about to spend my time on, connected to the mission? If not, why am I doing it anyway? That’s the first filter. The second thing is, does this directly drive revenue? The money. Does it drive revenue relationships, or does it reduce risk? That’s all tied to the capital. If not, it might not belong on my plate. Third is energy.

Some tasks look small, but they drain the life out of you. For me, running numbers, data analysis, all that stuff, it might not take that much time, but it sucks the life out of me. Other tasks create energy because they align with your strengths, they give you life, joy, fulfillment. You’ve got to focus on those things that actually give you energy. And then fourth is unique ability. Am I doing this because I haven’t slowed down long enough to train someone else, or am I actually really good at this?

A lot of high performers and people who achieve are addicted to being needed, unfortunately. So they keep things on their plate, not because they should, but because it makes them feel important. And that’s dangerous. The goal is not to be needed everywhere, the goal is to be most useful where you’re most gifted. So this is probably the first time you’re hearing this concept, keep it simple.

Right, the ego.

Look at what you’ve done over the last seven to fourteen days, and categorize them into two categories: are these transactional tasks or transformational tasks? Moving forward, over the next week or two, track what you’re doing, make a list, two columns.

Is this a transactional task that I could delegate to somebody because they’re better at it, or I could hire, a VA for ten dollars an hour or less? Or is this a transformational task that really needs me, that needs my critical thought, my relationship building, or my expertise? Keep it simple: is it transactional or transformational? Usually the transactional tasks are the ones you delegate first, especially if they’re sucking the life out of you, if they’re not something you’re good at, if they don’t bring you joy. Those are absolutely the first to delegate. For me, that’s bookkeeping and admin stuff.

I love how you’ve identified your areas of giftedness, your unique ability and interest, and you really lean into that and eliminate as much of the other things off your plate as you can.

Now what I would love, Tim, I know you coach high performers, and I’m curious if you’ve learned something from anybody you’ve coached that you’ve brought into your own business. Has anything from coaching changed the way you lead or do things within your own business and team?

I think it’s just the patterns I’ve picked up on, that I see in so many ambitious people. They know how to win. They know how to execute. They know how to make money, they know how to achieve, and they know how to carry pressure, they know how to be bold and courageous.

But a lot of times, asking just a couple simple but powerful questions helps reveal that on the inside they’re fragmented. Their level of faith, their most important relationships, their health, their emotions, they’re not fully aligned. So they’re successful from the outside, but there’s a gap between who people think they are and who they think they are, because they know they’re not clear, they’re not as energized as they’d like to be, and they’re not aligned as they’d like to be.

Helping people get crystal clear on what they’re putting their energy into, what they bring to the table, and why that’s important to them, cracks open so many different issues. I’m talking about some of the most ambitious people, eight-figure entrepreneurs who are not crystal clear. And what’s dangerous about that is they’ve climbed these mountains, they’re summiting, and they stand on top of this mountain and look around and realize they’re on top of the wrong mountain.

Because they thought they were going up the right mountain. Somebody else convinced them that’s what they needed to do. They never took the time to really think through, am I clear on where I’m headed, and why that’s important to me, not important to society, not important to what other people told me I should do, but important to me. And you could easily do this.

Going seven layers deep. I love doing this with people. It reveals a lot. You pursue something, you have to ask yourself, why am I doing this in the first place? And then you answer, typically, because I want freedom, or I want options. Well, why is that important to you? And then they say, well, because my parents provided it for me, and I didn’t really experience a lot of options or freedom growing up, and that’s why it’s important. Well, why is that important to you? And you go seven layers deep. It becomes very emotional. And if it’s not emotional, if it doesn’t really give you that heaviness, then it’s probably not your real why, you’re probably not at your real mission or purpose, why God put you on this earth. So that level of clarity is always the first thing I talk to people about when they come to me feeling unaligned, knowing they’re capable of more. It always starts with clarity.

And I understand you have this phrase, scaling with intention, which I think is kind of the contrast to what you just told us about, working your booty off and being at the top of the wrong mountain. So what does scaling with intention mean to you? Especially for a listener who is a real estate entrepreneur already busy and stretched thin, how does this not make them put more on their plate?

I love this question.

The first step is always the clarity.

Once you have that level of clarity, that well-built system is going to allow you to maintain that level of clarity without constant explanation.

To me, a process is ready to delegate when four things are clear. You have a desired outcome, you have the clear steps, you have the standard, and then you have the feedback loop. A lot of people will delegate tasks, but tasks can’t be delegated sustainably. Leaders, the right leaders, delegate the outcomes. If I say, go handle this, but I haven’t defined what success looks like, or what decisions they can make, or when to escalate issues, or how we’ll measure progress, I didn’t actually delegate, I kind of just dumped it on that person.

That’s where leaders create confusion, and then they blame that person because they didn’t think they did it right. So a lot of delegation failure is actually leadership failure. The test is, can someone reasonably, and with competence, follow the process and produce the expected result, and know what to do when something falls outside the norm? If yes, then it’s ready. If not, you don’t have a system yet, you just have trivial knowledge. So delegation without clarity is not leadership, it’s just dumping. And scaling with intention, there’s so much to put into that, because a lot of it is mindset and clarity, going in the right direction, and being able to articulate that vision and mission so clearly that others just want to join you and help you in this mission. But then it’s about putting these processes in place and properly delegating, so you can do those transformational tasks and not stay stuck doing the transactional ones, and you can delegate the transactional tasks well.

And it sounds like transformation always is work. If people are doing this differently than how they’ve been doing it, it’s going to be some work. There’s going to be that messy middle as they get these things figured out, and yet it sounds like on the other side of it, they’re able to have a more aligned life.

Trust me, I made a lot of mistakes in this arena.

That’s what I love about podcasting, we can come on and share stories like yours, Tim, and help other people get further faster. Avoid all the mistakes I made and just get to the finish line faster.

Exactly. I’ve never made any mistakes. My god. I would love to share some mistakes. I think the human brain learns more from the really hard mistakes than anything else. And if you’re not willing to learn the hard way and embrace challenge, and know that failure is part of the progress, that failure and lessons are inevitable, it’s how you frame it, it’s how you perceive it. If you make mistakes, or you tried once and failed and think, I guess it’s just not for me, that’s why business isn’t for everybody, and people can’t really continue to endure.

Because those who continue moving forward, and understand that those failures are just part of the process, they’re the ones who will see the fruits of their labor and the freedom.

Awesome. Well, Tim, I think you’ve shared a lot of words of wisdom with us here on today’s episode. If people would like to connect with you or discuss this further, what’s the best way for them to reach out?

Adrienne, thanks. I’m all over social media, I love LinkedIn. The best way, my website is thetimotykelly.com. And that’s also my handle on LinkedIn, Instagram, TikTok, Facebook, at the Timothy Kelly. If this conversation resonated with you, and you know you’re capable of more, and you think there might be a gap in your clarity, your level of energy, or that you might be misaligned, my website has a really fun, free, interactive clarity assessment you can take. It walks you through, asks you some simple but powerful questions to help you figure out where the gaps are in your clarity, your energy, and your level of alignment and purpose.

Then it’ll give you some answers, and I’ll send you a gap guide. It’s a PDF that walks you through what you could actually do about it now. Because information is all out there, you can get a ton of information right now with AI and Google, but without implementation, that information is useless. So you’ve got to do something about it, you have to know what you need to do. You have to learn and assess yourself, increase your level of self-awareness, and then start doing something about it and take action. That clarity assessment will allow you to have that awareness, and then the gap guide will be sent to you via PDF, walking you through the next steps, and then it’ll offer you an opportunity to book a call with me if you want to review your results and I can share and serve you in any way I can.

I love it. Well, thank you so much, Tim Kelly, for joining us. And for our listeners, that is a wrap on today’s episode. If you need help with a virtual executive assistant to scale your team, of course, reach out, I’m happy to help and get you connected with our team over at Workergenix. Or if you want to do that clarity assessment, go check out Tim’s website. I think that sounds really fun and exciting. So thank you, and join me again next week for another episode.

The post The Decision Framework for Fast, Confident Deals appeared first on Adrienne Green.

Most real estate entrepreneurs have no idea their retirement account could be funding their next deal. In this conversation, I sit down with Matt Moore and Courtney Ferrero from CamaPlan to break down exactly how a self-directed IRA or solo 401(k) works, the surprising range of assets you can actually hold in one (real estate, private notes, precious metals, even a dump truck), and the common mistakes new investors make when they get started. We also dig into how capital raisers and syndicators can use this tool to unlock a whole new source of investor capital. If you’ve ever wondered whether your retirement funds could be doing more for you, this episode will change how you think about that account for good.

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Hello everyone. I’m Adrienne Green, and today I have two amazing guests. I have Matt Moore and Courtney Ferrero, who are here with CamaPlan. Here we focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start, and this is a way you can do that with your money rather than your time. So thank you, Matt and Courtney, for being here.

Matt, let’s kick it off with you. For entrepreneurs and investors who are like, “I don’t know what CamaPlan is,” can you give us a 60-second version of what you do and who your company is built for?

Definitely. Really appreciate that generous introduction, and Courtney and I both appreciate this opportunity, so thanks very much for being able to chat with you today. CamaPlan is a self-directed IRA administrator. We opened our doors in 2003. We have thousands of clients across all 50 states, as well as DC and Puerto Rico, and we have over a billion dollars of assets under administration, so I say all that just to provide some track record on the company.

But a lot of people have never even heard of what a self-directed IRA is. So if I say we’re a self-directed IRA administrator, that might as well be Greek to a lot of people. A self-directed IRA is a kind of retirement account that allows you to invest in private or alternative assets that you wouldn’t necessarily be able to invest in through your tax-advantaged retirement account at a provider like Schwab or Fidelity. So CamaPlan, to your question, Adrienne, really caters to folks who want to take more control of their retirement capital and who like hard assets a lot of times and want to have more diversification in their total portfolio.

Thank you, that was great, Matt. And for our listeners, to give a specific use case, I’ll say that like my family, we have self-directed IRAs. When my husband left his engineering W-2 job, he had a retirement plan with that company where people would roll it over. He rolled it over to a self-directed IRA. So we didn’t just roll it over to an IRA and put it in the stock market. We rolled it over to a self-directed IRA where, like Matt says, you can choose and put it in these other assets. For us, that allows us to do a lot of private money lending within our self-directed IRAs, because my husband has one and I have one. We’re lovers of this, so I’m excited to bring it to all the listeners who are less familiar. Now, for people listening, I mentioned that we do private money lending in it. What type of investments can a self-directed account actually fund, and where do most real estate entrepreneurs start when they first make the move into this?

Courtney, you want to take that one?

Sure. So we have all different types of self-directed IRAs that you can invest in. We have different types of IRAs as well: traditional, Roth, SEP, SIMPLE, and different types of investments. The investments all range. We’re heavy real estate here with CamaPlan, meaning physical property. We also do notes, like you do yourself with your husband, private lending, private equity, small businesses. We do precious metals. We have a client who has a dump truck in their IRA, so they rent out the dump truck. There are different types of investments. Our clients bring the asset to us and let us know what they want to invest in. We do have CamaPlan clients invested with you and your platform, Invest Ally. So there’s all sorts of different things we do with CamaPlan.

Right, that’s amazing.

And that’s one of the other things: we have JV investors with our lending, and people can JV invest through their self-directed IRAs. I love that you guys are on here because so many people just don’t know about the opportunities or the options. So what would you say are some of the common misconceptions you hear from people who assume their retirement funds cannot be used for real estate, private lending, and stuff like that?

The biggest misconception is that you can do it in the first place. I go to my parents’ house for Thanksgiving dinner, and there’s a bunch of extended family, and naturally we talk about what’s going on with work and what we do, and my family members don’t believe me. They don’t think it’s something you can really do, just because people aren’t aware that you can invest your retirement capital into alternative assets. When you say, “Yeah, you can be the bank by lending from your IRA,” or “you can hold precious metals as opposed to just being in a precious metals ETF, you can actually hold the asset,” people are really shocked because I think there’s just some sort of programming that’s happened from people signing up for their 401(k) and choosing some mutual funds or working with their advisors. There’s just a lack of knowledge. So really the biggest misconception, and Courtney can attest to this because she’s on client calls all day, is that people are truly not aware that this is something you can do. As they pull back the layers on all the things they can do after they’ve maybe done their first deal, they continue to be surprised about all the opportunities there are. Not only is there a lot of discovery on the kinds of assets you can invest in, but also, to Courtney’s point earlier, the kinds of accounts you can use. The most common accounts we have are traditional IRAs and Roth IRAs, but you can also self-direct from an HSA, you can self-direct from an ESA. So when people say, for example, “Is there another college savings avenue other than a 529?” they’re pretty surprised to learn that, and it adds a whole new strategy to that savings plan. So I think the biggest misconception is that you can do it in the first place.

That makes sense to me. It was something new to me when I first heard about it, and once you figure it out, it’s like, this is amazing. Now, Courtney, when a new client comes to you who’s never worked with a self-directed account before, what does that first conversation usually look like?

It can run anywhere from someone who has absolutely no knowledge of self-directed investing to someone who knows what they’re doing and is bringing the investment to CamaPlan. We can start the process at any stage. If it’s a client who has no idea how self-directed investing works, we run them through how to open an account, how to move your funds, and make sure they understand it’s a non-taxable event. It’s an IRA-to-IRA transfer. They may be doing a rollover, which is non-taxable but reportable with the IRS. Then we explain how they can take the funds. CamaPlan will make sure the asset they’re purchasing is in good standing, that they’re not making a prohibited transaction, and we’ll double-check that the paperwork is done correctly, that their IRA is making the investment, not them personally, and then send the funds out to the investment provider, like yourself.

That really outlines the process so well. And what I appreciate from what you shared, Courtney, is that so often people feel like they need to be an expert on something before they even have that initial conversation. They’re used to working with other kinds of investments, brokerages, or firms where it’s DIY, where they have to know and pick their investment all on their own. It sounds like with CamaPlan, you can just come and ask, “What does this look like? Is this a good fit for me or not?” and you guys help people figure that out and figure out what the best path is.

Right. We work with them, make them feel comfortable, make them feel confident in what they’re investing in. Now, again, we can’t tell them exactly what to invest in, but we’ll guide them along and make sure they understand the process. They’ll be part of the process from the very beginning. We work with a lot of investment providers, and sometimes clients don’t understand the process, so they count on CamaPlan to hold their hand, and that’s exactly where we come in. We make sure everything is moving along smoothly, that the paperwork is done correctly, and that the transfers from other fiduciaries are done in a timely manner. If there are any hiccups along the way, we deal with things like medallion stamps, wet signatures, all sorts of different requirements from different fiduciaries where we’re transferring funds. So we’re there to make sure the process runs very smoothly, that it’s easy for the client and easy for the asset providers.

Right, and I’ll say from the investment provider standpoint, why did I invite CamaPlan to be on? Because it was easy to work with them. And I think it would be great for people to have their self-directed accounts with CamaPlan. So that’s why we’re here. Now, Matt, there are so many different types of accounts, as you’ve mentioned, and somebody might be listening thinking, “Well, I have a 401(k) versus an IRA.” How does a self-directed IRA differ from a self-directed 401(k), and does that distinction typically matter?

Yeah, good question. There’s a pretty extensive list if you want to go into all the nitty-gritty details of the differences between each, but I’d say there are three primary differences that really resonate with people about why they might want to use one versus the other. First would be contribution limits. A vanilla self-directed IRA, or just an IRA in general, is capped at the IRS’s contribution limits at the time, so right now it’s $7,500 for the year. In a solo 401(k), between the employee’s contributions and the contributions made by the business, you can contribute upwards of $70,000 annually. So the contribution opportunity to really grow your retirement account is much greater in the solo 401(k).

The second thing, and I probably should have made this number one, is just the fit: who can have a self-directed IRA versus who can have a solo 401(k). If you have some kind of income, you could potentially have a self-directed IRA, so it’s very broad in terms of who can have one. If you have a solo 401(k), you need to have your own business with no employees, so unless you’re a business owner, a solo 401(k) isn’t going to apply to you.

Well, I was going to say, for our listeners, all of our real estate entrepreneurs who have their own business where they’re their own employee and are trying to save for retirement, think about that: they can have a self-directed 401(k). That’s awesome, very cool.

Absolutely. And I was going to say that especially for entrepreneurs, there’s a natural predisposition to having a solo 401(k) versus the standard IRA, because the solo 401(k) does take more work. There are more documents that need to be managed on the part of the participant, the account owner. But if you’re an entrepreneur and you’re used to doing things yourself, that probably isn’t a new thing to you. So there is more work, but people who are entrepreneurs already kind of have that bone in them to manage things very diligently, so it doesn’t necessarily feel like such a burden to them.

Right, that’s a really good point. I know for us, we’re used to renewing the LLC every year and doing all these other paperwork things. We use Monday.com as a project management system. Whenever we have to do something quarterly, monthly, annually, whatever it is, that’s a task in there with an SOP, and honestly nine times out of ten our VA is the one doing it. So not a huge deal to add something else to that list.

Now, my next question is: we have an investor who’s evaluating whether to deploy retirement capital into a specific deal or lending opportunity. What should they be asking before they commit? What’s important for somebody to know when they’re evaluating a deal to use in their self-directed account?

Good question. Something that’s attractive about a self-directed IRA is the liquidity needs of the investor versus the timing of the investment. We work with a lot of real estate investment sponsors, and if you think about a run-of-the-mill real estate equity deal, it might have a five to seven year hold on it, and maybe the investment minimum is fifty to a hundred thousand dollars. If you’re the investor and let’s say you’re fifty years old, you have college to pay for, a wedding coming up, something like that, being out that money might feel a little daunting. But if you have that money in your IRA or an old 401(k) and you can’t touch it anyway without penalty, then investing from that source doesn’t affect your walking-around money, so to speak. It’s a nice way to participate in the deal without feeling the pressure of a liquidity crunch.

Now, the flip side of that, going back to the timing idea, has to do with required minimum distributions. RMDs are what you have to take when you’re about 73. The IRS forces you to take a distribution out of your retirement accounts. They look at all the balances you have and have you take those distributions. A lot of times, investments made through a self-directed IRA are into illiquid deals or hard assets, so you want to make sure as the investor that you’re not going to be overly saturated into a bunch of real estate or something like that, where you suddenly have to liquidate prematurely because you need to satisfy an RMD requirement. So I think those would be the considerations I’d make. Anything to add, Courtney?

I was just going to say, if you’re looking at doing a note or something along those lines, you can ask questions like: is it a secured note or an unsecured note? Like Matt said, how long are the terms? Am I getting interest returns on a monthly basis, a quarterly basis? Those are some of the questions to ask when you’re getting into a contract with someone.

Awesome. And I know you mentioned prohibited investments earlier, Courtney. Are there certain things people cannot invest in with their self-directed accounts?

Yes. So if you wanted to purchase a home, say your child is in college and you want to purchase a rental property for them to live in while they’re in school at Penn State for four years, they cannot live there, but their friends could. That’s one example of a prohibited transaction. Lending to yourself, if you have your own company and wanted to fund it with your 401(k), that’s a prohibited transaction. Anything that’s not at arm’s length, anything where you’re a decision maker, there are restrictions with that. Some transactions could be under 50% decision maker. We do look at the investment docs to make sure you’re not getting yourself into hot water with the IRS. There’s what we call direct lineage: parents, grandparents, children are all considered prohibited. So you can’t lend to your child’s business that they’re starting, but you could lend to a cousin. There are different types of people involved that you can lend to, but direct lineage is considered prohibited.

That makes it very clear, thank you. Now, Courtney, what is a common operational mistake you see from clients who are new to these self-directed accounts, and how does your team help them course correct?

We’ll see people trying to use non-qualified funds. They have investment brokerage accounts and think they can bring those over to CamaPlan and use those to self-direct invest. So we require additional information from clients when they set up their account, or ahead of time. We’ll ask them what type of funds they’re bringing, where their funds are, and they’ll send us a statement, but there’s no wording on there indicating if it’s an IRA or a 401(k). So we check, and we catch that. We don’t want anyone making a mistake with non-qualified funds. Sometimes when we’ve sent paperwork over to other fiduciaries, they may not pick up on those types of mistakes, so we’re extremely careful.

Awesome, and it’s just nice to know, because if somebody is new to this, they could inadvertently make a mistake, and you don’t want to do that with all of these tax-law-related issues. It’s nice to have somebody who’s an expert on it having your back.

Yeah, can I speak to that point? I think part of the reason people are apprehensive about doing a self-directed IRA is because of what you just said. It can seem overwhelming or intimidating because you don’t want to do anything to mess up your IRA. The nice thing about CamaPlan is that although we have the track record, we’re only a company of about twenty-nine people. So when a client calls and talks to Courtney and they’re just getting things started, and a week later they have another question and call back, they’re usually going to get Courtney again, or Courtney will be available. So it’s not like they have to restart the story. Courtney remembers them and remembers what they’re doing. That familiarity with the situation, and the natural checks and balances that come into play from a compliance standpoint, from an IRA compliance perspective, is very crucial in making people comfortable with this new kind of investing they’re doing with their retirement capital.

Yes, that speaks to me and I’m sure it speaks to our listeners, because you think of big banks or other financial institutions, you call and get a call center, some random person who doesn’t know your history, and it’s really frustrating. It’s not a good experience. But it could be like, “Hey Courtney, I talked to you last week, you know what’s going on, and this is the new question I have as I’m trying to figure this out.” It’s a very different experience.

It’s like one of my favorite things: I speak to a lot of investment sponsors, and naturally they ask, “Well, what makes you great?” I love flexing Courtney, dropping her name, and that familiarity, because Courtney is going to be the person they talk to, and when they’re ready to make the investment and go talk to our operations team, they’ll talk to Sarah from our operations team, and Sarah sits five feet away from Courtney. So it’s all very nice and cohesive. That really affects the client, the investor, quite a bit, because they know they’re not just a number. They know that Courtney and Sarah, or whoever they’re working with, really know who they are, know what they’re trying to do, and are looking out to make sure the whole transaction goes smoothly.

Love it. Now, Matt, as we’ve talked about a little bit, private lending is one of my favorites, and I know it’s a big use case for self-directed accounts. How would you recommend somebody think about structuring notes or private lending within their self-directed retirement account? What’s important for them to understand going in?

Yeah, a little bit about me: I used to work on the capital-raising side prior to CamaPlan, and I worked for a real estate debt fund. We also sold fractional participations in notes, so I’m kind of partial to notes too. In terms of how someone should think about doing private lending inside of their IRA: number one, when an investment is made from the IRA, whether it’s a note or anything else, that investment is going to be titled to their IRA. Your IRA is its own entity. Whether it’s your IRA at Schwab or your IRA at CamaPlan, they’re all their own entities, not you personally. So the titling of that investment is going to be to your CamaPlan account, for example, “CamaPlan FBO, for the benefit of Matt Moore IRA.” Having that knowledge, both mechanically, that you have the titling correct, but also understanding that relationship, is very important, understanding that your IRA is going to be the one that holds this loan. CamaPlan will administer that account for you, so you’re not going to be involved in the management of that investment; it’s going to be your IRA.

As it relates to how you structure the note, CamaPlan can’t give you any advice on how you should do things, because we’re not allowed to give investment advice. But what seems to be the best practice for a lot of investors doing this is either working with a real estate attorney or someone like that to help them, or a lender to help them originate and structure the note and make sure all the pieces are in place that they need for a real estate note, assuming it’s secured. That’s definitely number one. And then, or they’re buying notes that have already been originated, so they’re taking themselves out of the structuring part. They know what their buy box, their credit box, looks like, and they’re going and buying existing notes to make it a little easier to participate that way.

That makes a lot of sense, and I’ll say, we’ve been doing private lending for over four years now, and we see so many people who get into it without using a real estate attorney to structure that original note or think through all the little nuances that go into it. Like, what if the borrower needs to extend at the end of the original term? Does your original note include what that extension is going to look like, so you don’t have to revisit it? Things like that. There are a lot of people who get into it who haven’t thought of all those what-ifs yet, and it’s better to think of them up front.

Yeah, absolutely. ChatGPT is great for a lot of things, but go with the professionals who can help you with this, learn from them, and be able to do it yourself one day, sure. But work with companies who are selling notes and providing notes so you can learn from them, or there are schools that teach it, or work with a lender or someone who will walk you through exactly how things need to be structured so you’re not getting caught in a situation you didn’t intend to be in, because now the borrower is expecting a 12-month extension on a 12-month note.

Right, that makes sense. So Courtney, let’s say we’ve got a listener here who’s like, “Sign me up, I’m ready to go.” How long does the onboarding process usually take, and what can investors do to make sure it moves forward without delays? Because every real estate investor I know, once they decide to do something, they want it done yesterday. So how long will they need to get this set up, Courtney?

That’s always the question. I ask them, “Are you going to miss the deal? How much of a rush is this?” Most of the time they’re just starting out. CamaPlan can get the account open relatively quickly, within the day. It takes about 15 minutes online with your driver’s license. Like I was saying earlier, when you do the funding, we have a section in the application where you fill in where the funds are coming from, so we know exactly where you’re moving your funds from. You’ll upload a statement. It all depends on where they’re moving the funds from. If it requires a medallion stamp, there are some things that would slow it down. However, we really try to do our due diligence on the different types of Vanguard, Schwab, Fidelity fiduciaries that are holding the other funds and what their requirements are. We’ll actually get on the phone with the client and, say, Fidelity, and ask their requirements so we can get this expedited as quickly as possible. So to answer your question, all things moving relatively smoothly, within three weeks the account is open, the funds are brought over, the investment paperwork is sent to CamaPlan, we review everything, we make sure it’s titled correctly, and then we get the funds out the door to the investment within 48 hours.

Amazing, that is nice. The word that comes to mind, Courtney, as you describe that, is that you work like an advocate for your clients to help make this all happen.

Absolutely. We like it to run simple for them as well as for ourselves. The fewer hiccups we have on our end, the easier it is for everyone involved. Some clients need a little more hand-holding and instructions, some clients know exactly what they’re doing and listen to the instructions. A lot of times we can’t call a Vanguard or a Fidelity ourselves without the client on the line, so we do need them to take some ownership to some degree, but we’re also there to help them along the way as much as possible.

Love that. Now, Matt, I also want to address, we’ve talked a lot from the investor standpoint, but this podcast is for all real estate entrepreneurs, including people who are running syndications and doing capital raising. Can we talk about what that self-directed account conversation can look like for them and their investors?

For sure. As I mentioned, this is the sandbox I play in primarily, and from that previous job I mentioned earlier, I was working with investors, a lot of whom were investing from their self-directed IRAs. That’s really how I got my introduction to self-directed IRAs in the first place. So if you’re an investment sponsor, if you’re raising money, self-directed IRAs are a great tool for you, because they help your investors find a new source of capital to put into your deals. And as I’ve said before, and I’ll continue to shout it from the rooftops, people are not aware of this option. So the way capital raisers can really benefit themselves is just by talking about it with their investors. You don’t have to be an expert. It’s not a financial advice conversation, it’s just planting the seed: “Have you heard of this? Did you know you can do this? Do you have an old 401(k)? Do you have an IRA? Because if you do, you can use it in this deal.” Is it going to be a fit for everyone? No, of course not. But a lot of the time, from my own experience and the experience of working with investment sponsors having these conversations, most investors don’t know they can do it and are interested to learn more. From there, that’s where you can leverage a custodial partnership like CamaPlan to come in and do the heavy lifting part of the conversation, to figure out whether they truly have these qualified monies the way they think they do and whether they can access them. These conversations can be a little tedious, and real estate entrepreneurs have plenty of things to do already, so we’ll do that part. We’ll figure out what’s actually available. Then, if we figure out that this person really does have that money available to put into the deal and they understand how it works and they like this, we do that stewardship piece, that advocacy piece you described. We’ll get them through the finish line to get their account set up and ultimately deployed into the deal. So it’s not about throwing a name over to CamaPlan and just crossing your fingers and hoping for the best; it’s about having a value-add conversation with your investor, and if it makes sense, bringing CamaPlan into the conversation and us working together to complete that strategy for the investor into your deal.

That was a great overview of what it can look like and how it could help them. Thank you so much, Matt. Now, as we wrap up, is there anything else, a thing that most real estate entrepreneurs do not know about self-directed accounts that we haven’t hit on yet, that you wish every person in the audience understood before they did their next deal?

I think probably the best information to give them is that they don’t have to buy a piece of physical real estate. They can go in the direction of notes. As long as, if they’re just starting out and they don’t have a lot of qualified funds to get started with, there are some other investments they could do. We don’t tell them what to do, but maybe a tax lien or something. They’re in that real estate space, right? A lot of them, when we go to different local meetup groups, network very well, so they could find somebody in their network who’s interested in investing with them or borrowing money from them. So there are all sorts of different ways you can really get started.

Love that, very good. Matt, did you have anything you wanted to add?

Maybe just to add on to that: the thing real estate entrepreneurs should know is that there’s way more you can do inside of a self-directed IRA than you can’t do. So if there’s some sort of nuanced or complex real estate transaction, or just a different kind of real estate transaction you want to participate in, but you don’t have the capital available right now, or you want to find other ways to do it, a self-directed IRA could help you execute that transaction, or at least support you in executing that transaction, either from the one you hold yourself or from your network’s IRA capital that could help with your deal. So talk to us, let’s have a conversation about what you’re trying to do, and we can brainstorm ways it might work for you, and we’ll start from there.

Perfect, well said. And if somebody’s interested in connecting with you guys or learning more about CamaPlan, what’s the best place for them to reach out?

Go ahead, Courtney.

I’d say probably our main number, 215-283-2868, extension 3. You’ll get me directly. Or our website, camaplan.com. You can click on our website and schedule an appointment at any time.

Perfect, thank you guys. Thank you again, Matt and Courtney, for coming and sharing all about self-directed accounts, so we can get more people in the know and leveraging those funds. And for our listeners, if you got value from this conversation, maybe shoot it over to a friend of yours who needs to listen as well.

The post What Most Investors Get Wrong About Self-Directed Notes appeared first on Adrienne Green.

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.

The post Self-Managing 19 Units Without Being On Call 24/7 appeared first on Adrienne Green.

I’m Adrienne Green, and in this episode I sat down with Ana Garcia, a real estate investor and CPA who works exclusively with clients in the real estate space. Ana’s journey started in an unlikely place: a senior auditor handed her a copy of Rich Dad Poor Dad during her very first job out of college, and she’s been building wealth through real estate ever since. Today she and her husband hold fifteen doors across Miami and Broward County, spanning short-term, long-term, and midterm rentals. In this conversation, Anna pulls back the curtain on the accounting side of real estate investing that so many landlords ignore until tax season blindsides them. We talk about why cash flow, not appreciation, should drive every buying decision, the exact financial habits she recommends tracking every month, how to know when it’s time to hire help with your books, and why “more doors” doesn’t automatically mean more wealth. If you’ve ever felt overwhelmed by your bookkeeping or surprised by your tax bill, this episode is packed with practical, proactive strategies you can start using today. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

I’m Adrienne Green and today we’re with Ana Garcia. Here we focus on how real estate entrepreneurs break free of the grind and get the freedom they wanted at the start. Ana’s awesome because she is an investor herself and a CPA who works with those in the real estate space. So Anna, thank you so much for joining us today.

Adrienne, so glad to be here with you.

Now for people who don’t know you, can you give us an idea what your real estate portfolio looks like today?

Right now we have fifteen doors. I say we because I own one apartment with my sister, and the rest of the fourteen doors is with my husband. So total of fifteen.

Awesome. And I’d love to hear your story of how you went from CPA to investor.

So I had just graduated college and was starting to work at one of the big accounting firms. It was my first job out of college and I was auditing, and my senior, the way these firms assign the jobs is you go to the clients and it’s the staff, usually one or two, and then you have a senior, a manager, and the partner. So we had the senior on site, it was me and him, and one day he starts telling me about Rich Dad Poor Dad. Have you read it? And I said, what is that? I have no clue. I was going to be a CPA my whole life, I was just starting my career, and he said you have to go read it. So that’s how I got so lucky. I feel very blessed because I was able to start my real estate journey very early on.

I love that, and it’s so funny because, like we were saying before we started recording, I’m in Lima, Peru right now, and we visit bookstores a lot because my kids love to look at bookstores. Here we saw Rich Dad Poor Dad. It’s one of the books that when we go into bookstores around the world, we see it pretty often. It’s pretty distinctive and you can identify the name in any language. It’s crazy that you got introduced to it at your W-2 job, and that became the start of your real estate investing journey.

Yeah. Rich Dad Poor Dad is the one book that most investors say got them started into real estate.

Yes, it’s been pivotal for sure. Now you got started after reading Rich Dad Poor Dad, and you have a property with your sister. Was that your first one?

It was. It was actually when I first read the book, this was 2007 or 2008, just when the economy was going down. So it was a perfect time for us to start. I wish I would have bought more. I wish she and I would have gotten more investment properties, but we just got that one apartment. We got it for, I mean, it’s Miami, we got it for almost free, I would say. We paid $49,000 for this two bedroom, one bath. We did have to make a few repairs here and there, but it was awesome. I think it’s valued now probably at $300,000, if not $280,000.

That’s awesome. And then you continued doing the investing with your husband over the years.

Right. So we first acquired a studio, then we went for a fourplex, and then finally got an eightplex. So we’re looking for our next investment now, actually.

And you focus in the Miami area with long-term rentals, or tell me a little bit about your niche.

We’ve done it all, I would say. We’ve done short-term rental, that was how we would begin the investments, and then we would convert it into long-term. So we’ve done short-term, long-term, and the studio we have is actually midterm, three months at a time.

So you focus locally, Miami-specific, for your niche?

Yes. We started in Miami, but Miami has gotten very expensive. Even these days that we see some more inventory out there, Miami has kept a lot of its value. It’s decreased a little bit, but it’s an area that’s very pricey. So we have also moved to Broward, which is the next county.

Yeah, I will say Miami, when I read the national real estate news, Miami’s up there. It’s hot right now. Everybody’s talking about it. So I’m glad you’ve got some nearby areas that continue to work for you in terms of investment.

Alright, so you’ve invested for a long time. A lot of real estate investors have not been investing since 2007, 2008. I imagine you have some lessons learned for our listeners from that experience. What are a couple things that you would say you wish you knew when you first got started?

I remember reading that when you start investing, you don’t go for appreciation, you go for cash flow. Your investment has to give you cash flow, not necessarily be in an area where it’s going to grow. We were lucky to invest when times were still picking up, but still not at the level they’re at these days. I would say, with the fourplex that we bought, the units are huge, they’re big, and we thought, my husband also works in construction, so he has that background, he said we can even convert this from a fourplex to an eightplex. But then looking back we realized it only has one bathroom. So to convert it, we’re going to have to add another bathroom. So we learned that lesson: if it’s something we want to convert, let’s make sure it already has what it needs to be able to grow into a bigger building. That’s one thing. And then cash flowing is very important, just to buy. We bought that fourplex in a very good area, but it hasn’t cash flowed since we bought it. At the end of the day we haven’t lost money, but I think going forward we want to make sure it actually gives us a return, the actual cash flow.

Right, and that’s a really good point to make. So many investors get into it and they don’t get the cash flow they were expecting. It’s fine if you’re okay with buying something purely for the appreciation, the challenge is a lot of people think they’re going to get cash flow and then are surprised when they don’t. So good to point out that that’s something to really measure.

Now since we’re talking about the numbers, let’s talk about taxes, because that’s your jam.

The fun stuff.

You know what, the funny thing is taxes are boring to 99% of the population, but you get in a group of real estate investors and we’re so excited to talk to a CPA or talk about taxes. It’s kind of funny. Now, most investors think about taxes once a year in a panic, they’re behind, their books are not up to date, they’re always extending because they don’t even have their numbers done at year end. What if we instead treated tax strategy as an ongoing part of running the business instead of just a season, what would that look like for investors?

That would change their lives, their investment journey, their wealth, everything going forward. What happens is taxpayers are used to fighting their taxes at the end of the year, but the end of the year is actually March or April, the year that you’re fighting for has already ended. A lot of the strategies, and remember, real estate investors love to talk about taxes because the IRS has all these opportunities tax-wise that we can take advantage of, so if you as a real estate investor are not looking proactively at your accounting, proactively at your tax situation, how are you even going to mitigate and really use all those strategies that are out there to lower your taxes? So with our clients, we work proactively, we meet with our clients throughout the year, we go through their financials, we tell them how much taxes they’re going to pay in the year and how we’re going to mitigate that together. It’s about knowing their books, knowing their cash flow, knowing what expenses are really affecting their bottom line, and what strategies we can implement to make sure that’s actually mitigated. And another thing, as real estate investors, we’re always buying, selling, these are big decisions, and taxes are going to get impacted. When you know what options you have out there to pay zero taxes, some of our clients pay zero taxes, that’s really important. That’s why it’s important to be proactive.

This resonates so much, because as an investor and a business owner, it was so transformational when I brought on one of my VAs to start doing the bookkeeping and accounting. Every Friday, all of our transactions had been categorized in QuickBooks, and I had an exact tally of where we stood every Friday, what the net income was, what money I was expecting to have come in, what outflow I had with credit cards and everything. Being able to really know where we stood financially every Friday was huge. It was amazing.

So that’s really where it needs to start, right? For you to have these productive meetings with clients, they have to have up-to-date books to start off with. So what do you recommend for investors who feel overwhelmed with their bookkeeping and accounting and are like, “I don’t even know where to start, I hate doing it, I time block time to do it every week but then I never do it because emergencies and fires pop up”? What are your tips for clients in that situation?

A few things. The first tip I would give is, anything relating to expenses, any statements, create a folder, and it could be something physical, and also on your computer, depending on what kind of documentation you have, and just put everything in there. That’s tip number one: keep everything in one place, organized. The second thing is, we’re investors, we love real estate, but we may not necessarily like and love the accounting. Accounting is very technical too. It may be easy for you to classify something like eating out, you know that’s meals, but what about the balance sheet accounts you don’t know, like equity? All these things are like French to us. So at that point you need to hire help, it could be a VA. There are a lot of virtual assistants out there that do an amazing job with the books. So subcontract that work. If you don’t feel comfortable, because I know it’s your financial situation, maybe you don’t know if the person’s good, at the beginning you have to kind of be on top of it, but once they get the hang of it, once you trust that person, it changes your world. Looking at your financial information on a monthly basis changes your world and your peace of mind.

Fabulous. So let’s say somebody gets the help that they need because they’re not doing it well themselves. What do they need to track now? What financial habits do you recommend people have, or what numbers should an investor be tracking and viewing monthly if they really want to get a handle on their real estate business’s finances?

Number one, cash flow. Again, we invest to have more money, more wealth, so cash flow. Make sure you’re tracking what your expenses are, what your biggest expenses are, and can you even lower those? Insurance is one big one that increased over the past few years, and now it seems to be getting a little adjusted, maybe we can get those lowered. So make sure you’re tracking your cash flow, not just how much rent you’re getting. That’s number one. You should always have some reserves, things can happen. For capital expenditures sometimes, even though we have insurance, we do need to have a reserve on the side for any expense you weren’t counting on. So those are the two things. If the properties are cash flowing, you’re in a healthy position.

Okay, so if I was an investor listening and accounting is a foreign language to me, I could make an appointment with myself, or my VA, or my bookkeeper, whoever I’m using, go in every month into QuickBooks or whatever software I’m using, look at the statement of cash flows, make sure it’s positive at the end, and look at those expenses at the bottom and ask, is this what I was expecting, or are any of these a surprise because they’re larger? Is that accurate?

Correct. Yes.

And then I want to look at my balance sheet and make sure I’ve got some reserves, some assets in that balance sheet that I could use if an emergency popped up.

Exactly, exactly. When you’re looking, also not just the cash flow statement, you can also look at your income statement. And if you use QuickBooks, you can choose if you want to see it on a cash basis, so it’s everything that came in, everything that went out. That’s an easy review. You can also compare this year to last year and see what changed, what improved, what expenses are getting higher. So yes, definitely that’s the way to review it.

And I love that aspect in QuickBooks, how easy it is, you just click a button to compare it to last year. That’s actually in the SOP for my executive assistant, every month they do that for all my investment properties, and if it’s over a certain margin, they flag it for my attention. That way I’m not doing the routine check, but if something’s atypical, they bring it to my attention. Love that, it’s been really helpful.

That’s awesome. Yeah.

Okay, now let’s talk about your own CPA firm, because that is a business as well. You’ve had to build it up as an entrepreneur in the same way that real estate investors are doing with their real estate business. How have you grown and systemized your own firm so that you have the time to do your investing and your business and life? Because that’s always a challenge for people in the real estate space.

I’ll tell you, I have three kids, and that’s like another full-time job, another business on its own. I think you have three kids too, right?

Yes, yes.

So it is difficult when you’re juggling so many things. As a woman, I think we carry a lot on our shoulders, so we have to make sure that we’re efficient, and this is when help comes in. For my CPA business, just like for my real estate business, I have help, we cannot do it on our own. My husband works too, so we have to make sure we’re systematizing things. The way I’ve done it in my CPA firm is: first, I’ve hired a team of experts that get the work done, and I just keep the relationship with the clients and keep the tax strategy at the higher level. Everything else has to be done by the team to make sure things are running smoothly, that no client is left behind. We’ve also worked with QuickBooks for a long time, we’ve just kept it that way. Any clients that come in usually already have QuickBooks, or we integrate them into QuickBooks. And the people we work with, the sponsors who help our clients do the different strategies, like 1031 exchanges or cost segregation, are also vetted already. So we know that whenever we send a client to these sponsors, these vendors, they’re in good hands. That’s the way we’ve gotten to feel relieved, and the fact that we’ve specialized in real estate also makes it a lot easier, we work with real estate investors or anybody wanting to invest in real estate, starting their real estate journey, and that makes it easier too. It’s a system, we already know what we’re dealing with. Accounting and taxes are not easy. Depending on the industry you’re working with, there are different strategies, different rules. So by focusing on real estate, everything flows in an easier way.

Awesome. There are two gems there that I really want to dig into further. The first is how you’ve leveraged a team. That resonates with me, if you think of the cash flow quadrant from Rich Dad Poor Dad, we often start as an employee, we move to self-employed, but the way to get from self-employed to business owner is to have people working for you. That’s a really tough jump for a lot of real estate investors. It’s a tough jump mentally, it’s all a mental game of trusting other people to do the work. What worked for you? What did you have to tell yourself to make that jump?

At the beginning, I did not want to let go. I was refusing to hire anybody, I would do everything myself. I said I’ll just have a few clients and I’ll do everything myself, I don’t want to have employees. This was at the firm, actually, because in the real estate side we always had a manager. But it was really difficult to let go until I kept going to trainings and they kept saying you need an assistant, you need some help. So I hired my assistant, that was my first help, and then I saw the difference. I saw that when I wasn’t at my desk, things were working. My clients were being served. I was not stressing out about something that was pending. So then I hired my second person, I actually promoted my assistant and hired a new assistant. And that’s how it becomes almost like, you really need it. I think you always have to think about what is that 20% that only you can do, and then subcontract the other 80%. Make sure that data entry, we have experts, and you have to know what kind of role, what kind of person, what kind of experience you need for the different roles. For example, in the firm we have our CPA who helps with strategies and reviews the tax returns, she has that accounting expertise. And then we have our bookkeeping team, there are experts in bookkeeping. We have our tax team, experts in taxes. And then we have the admin people keeping the clients connected with everyone and the work flowing. So you need to know when to hire a professional, and that’s how we’ve done it. But it’s worked out so greatly. I highly recommend it. Start with a VA, if you don’t have anyone, start with a VA, definitely.

Love that, and I appreciate that you shared how it was tough at first, but you had to just do it anyway, and then you saw the benefits. I think that’s often how it goes. Now the second thing you hit on for your CPA firm that I’ve seen myself is your niching down. That’s the challenge, as a CPA you think, I can help anybody who does taxes, every American is filing taxes. And in the real estate space too, it can feel like everything is real estate, there are five million ways to invest in real estate. So talk to us more about this niching down you did as a CPA and how that could inspire real estate investors to niche with their investing.

I think this comes from the book The Pumpkin Plan too, fantastic book, I recommend it. There’s a saying that when you’re chasing two rabbits, you’ll catch none. You have to stay focused on one thing. If you’re investing in real estate and you want to do short-term rental, but then you want to do long-term rental, but then you’re buying multifamily, when you niche and you know, okay, I’m going to stick with single family homes, you see people being successful in so many different asset types. It’s so important, it makes things easier, you understand how things work, you can create more economies of scale, when you know the problems that exist in that particular niche. It’s a lot easier to handle and it’s more efficient at the end of the day.

Yeah, and I think that’s exactly right. You can be more efficient and really focus. You said that so well.

Now you sit across from a lot of investors at moments when real money is on the line. You see the ones who can make clear decisions, who can move forward, and the ones who freeze or react emotionally and don’t make progress. What separates those two people?

The people who make the clear decisions are the people who know their numbers. There’s no doubt about it. And with that comes moving faster in the deals. When you’re going to sell a property, you’re going to pay capital gains tax, there are different options. When you have a team of experts behind you, and you already know the consequences of each possible outcome, you can make a better decision. You’re clearer on what the next step is. That’s what’s different between someone who’s prepared and someone who’s not. The one who’s not prepared doesn’t have books on time, doesn’t have their financials ready, many times doesn’t have their taxes ready. So how are you going to proceed with something if you don’t even know if you’re going to be able to work with a lender? You can make better decisions when you’re prepared, especially when you know your numbers.

That’s so true, so true. I love that. And it’s not just, part of it is that lenders want to see that latest tax return. And even before that, you don’t even know if you should be buying that property, if that’s a smart financial decision, if you don’t have your numbers done. I love it.

Alright, now Anna, there’s this belief in the real estate investing space that the more doors you have, the more volume, then that’s more wealth and more prestige. Tell me the truth on that, does more doors automatically mean you’re better or wealthier?

Not at all. We’ve seen clients who continue to buy and continue to buy, but at the end of the day they’re having to get a second job because they need to pay for a lot of expenses. A lot of these properties, if they’re old, if they have a lot of problems and you didn’t consider that and take it into account when you were making your offer, then you’re getting into a problem, and instead of giving you money back and cash flowing and adding value to your life, it’s really draining you financially and emotionally. So having more doors doesn’t mean more wealth. We have to be savvy investors when we’re buying real estate, we have to make sure we’re looking at every aspect of the deal. And another thing too, we see clients just going to buy real estate for tax purposes. That shouldn’t be your number one reason. The tax benefit is the icing on top, but at the end of the day you want to make sure you’re buying a good deal that’s going to work for you.

Very good, I love that. Well, Anna, if somebody would like to connect further and learn about your CPA services or follow up with a specific question, what’s the best way for them to connect?

They could visit our website: annagarciacpa.com.

Perfect, and we’ll have that in the show notes for you to grab. Thank you so much, Anna, for sharing all of this as an investor yourself, and as a CPA who works with investors. Very, very helpful for people to think big picture and to motivate them to get their books in order if they’re not already.

If you got value from this conversation, listeners, do me a favor and subscribe wherever you are listening, and leave us a little review, it really does help. See you next time!

The post The Real Cost of Doing Your Own Bookkeeping appeared first on Adrienne Green.

In this conversation, I sit down with Mike Deaton, known in the real estate world as the land guy, who spent ten years building a vacant land flipping business that now funds his entire portfolio and supports a life of full location freedom. Mike and his wife Lydia left corporate careers in 2016 after simultaneous layoffs, with no real estate income, no side hustle, and no backup plan. What they chose to do instead is what makes this conversation worth your time. We cover how they structured their business to run without them in the weeds, the eliminate-automate-delegate framework Mike carried over from 25 years in corporate operations, how they think about deploying capital across land, multifamily, and other asset classes, and why the vision behind the business matters more than the strategy. If you are a real estate investor who is still doing most of the work yourself, this conversation will give you a clearer picture of what it actually looks like to build a business that supports your life. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Hello everyone, welcome back. I’m Adrienne Green, and today we’re here with Mike Deaton. We always focus on how real estate entrepreneurs break free of the grind and create the freedom that they wanted at the start, and Mike is a perfect example. So let’s jump in here. Mike, for listeners who are just meeting you, can you give us the 60-second version of what your real estate portfolio looks like today?

Yeah, happy to. Thanks for having me on the show. So most people know me as the land guy. I’ve been for 10 years building a vacant land flipping business. And that is, I would say, 90% of what my wife and I do in terms of an income level. And that’s what we started with. But over the years, we have diversified into other asset classes, largely multifamily syndications, where we have been both passive investors and we’ve been active deal participants. We’ve partnered in over a thousand doors, around twelve hundred doors. Several of those deals have gone full cycle. So for people not familiar with syndications, a lot of time there’s a fixed value add window where you force appreciation and then there’s an exit. And so we’ve done some full cycle deals.

We have less intensely gotten into single families as well, but land for us is so stress free and the returns are just better than any of the other forms of real estate that we stay primarily in our land lane. Where we like to diversify is to get tax benefits out of depreciable assets. And so we do a little bit of both still in that way. But that’s kind of what the portfolio looks like today.

I love that. I love your summary of it because it and that’s why I feel like when somebody thinking of the life cycle of a real estate investor, right? Versus when somebody starts and as they mature there, you start with one thing, you get shiny object syndrome and try a lot of different things, and then you realize kind of typically you’re two or maybe three things, right? Because you’re going to optimize for either net worth or cash flow or tax benefits and you might have some different strategies for those different pieces. And that sounds like what you’ve really done.

It is, yeah. Yeah. It’s been really good to us.

Now I understand that you guys left corporate careers in 2016 and went full time into real estate together. Now there’s a lot I want to talk about there. The first is let’s talk about leaving corporate and what that was like for you.

Yeah, my identity, if you will, was really being a corporate warrior. Out of college I joined the workforce. I was with big tech companies, three big tech companies over a 25 year span. And I focused primarily in operations and running supply chains for Microsoft and Nokia mobile phones when Nokia was one of the biggest phone makers. And that was really what I saw my professional career was and was going to be. And so it was all about climbing the ladder, getting promotions, all the stuff, the political infighting, different things that go along with running a career out of big corporations. And in 2016, I was let go. I mean, I had been on the giving side of the table of many, many layoffs across my career.

And it finally kind of caught up with me for various reasons. Microsoft was consolidating operations. I was living in Dallas Fort Worth. It was kind of a small satellite office for them. And I was really disenchanted in that moment as well. I was traveling 50% of the month. I had an international team, and so I was gone from home. My wife and I met each other in the workplace.

And there was a period of about three years where we commuted to work together, we had lunch together, we spent time pretty much in an open office environment together. And then that passed, and we both kind of found ourselves in different companies. And when the layoff came, Lydia, my wife, also got laid off within days from her healthcare company. And so…

My goodness.

That was all the income we had. We didn’t have real estate at that time and we didn’t have a side hustle. And so our income stopped. Our savings account started going in reverse because we were dipping into savings. And fortunately we had a safety net underneath us. And my knee-jerk reaction really was to get back into the workforce. And so I started interviewing with Amazon and Tesla and Apple and other big tech companies. But they’re all West Coast based. They all have their own company culture. And so all of those thoughts just started really nagging and my anxiety was building about what was that going to be like starting over essentially at a new company. And we both took the time to consciously pause and think about was there an alternative path for us?

And in that process, we dug into our core values. What did we want out of our future? We did some exercises like what is our future life? What was our perfect day? Those kind of things. And none of it was corporate America tied or W-2 salary tied. And so that set us on a journey of looking at what type of business could we start or how could we generate income outside of a salary? And that led us into land and these other forms of real estate and we can get into that. But that was really the off-ramp for us to get into an entrepreneurial business. And we wanted to do it together. That was very much a part of what we wanted our journey to be, spending time together, traveling, working, having shared goals and those kinds of things. And so that was our pivotal moment and we fought the urge to just get back on the hamster wheel and chart a different path.

That’s really impressive. Now, because it’s what I hear most of the time, I thought you guys had probably already been in real estate investing and then you had enough alternative income built up that you could leave the W-2s, because that’s what I hear ninety-nine times out of a hundred. But no, you guys, it’s crazy both getting laid off within a week of each other and then not just running back to find another W-2. That is a bold move, I am impressed.

Like kudos to both of you.

Okay. I don’t advise people to do it that way. When people talk to me, I don’t recommend what we did. A lot of things lined up for us. Like I said, we had a safety net, we had our financial house in order, if you will. And so it afforded us that opportunity. But at the same time, we engineered it. We had a home in Dallas that we sold and we took the equity out of it. We rented for three years while we built our business and we downsized. We moved to Colorado, so our cost of living went up a little bit, but we rented a townhome. Two adult daughters were off into college or just about to go. And so that was all taken care of. And so there were a lot of things that made it more approachable for me personally. The risk that I felt came along with starting something new, there was a lot less.

Lydia and I were in it together. And so there were a lot of factors that kind of opened the door for us, but we stepped into it. And so that was, but yeah, it’s not, I mean, I definitely advise people to leverage your W-2, leverage your nine to five to work your five to nine, as they say, kind of a situation.

I know everybody who’s had a layoff I think is really on fire for those people who are still in the W-2 to be like, use it, leverage it and build that side business while you’ve got it, right? Because you never know what’s going to happen. So

Totally.

Now, I would love to hear as you guys got started, what was it like for the two of you working together? Because there are a lot of husband, wife, spouse duos in the real estate entrepreneur space, right? As investors, as agents, etc. Some do it really intentionally, some fall into it and just kind of go along. It is how it is. You guys seem like you were intentional in how you set things up. Just guessing.

Yeah, we were very intentional. We had experienced working together before. Fortunately, we love each other and we like each other. And so spending a lot of time together was something that we intentionally wanted to do. We also, I would say, have a natural, I worked in senior executive positions. And so used to delegating, seeing big pictures, forming strategies, but also being down in the details and setting up processes and systems and automation. Lydia’s proclivities are more task-oriented, getting things done, really digging into actions. And so we found a very natural way of working that kind of set us up for some harmonious success, if you will. We talk to a lot of people who can’t believe they could never work with their husband or wife, those kind of things. But for us, it came very naturally. I think a big part of it also is just having this shared vision and goal. And when you have a big why or an overarching purpose, it’s a lot easier to work through disagreements or to be aligned in certain paths. When we started our land business, we also naturally segmented the business a little bit. Land is largely about acquisitions and sales, as you know, a lot of real estate is. And so we kind of found our own lanes to give us some individual focus, but then also be able to come together and work together to make the whole business work. And so there were some things that we intentionally designed and orchestrated, but it was an intentional pursuit, but we had very natural domains that we kind of found ourselves in and still do today.

Mm-hmm.

Yeah, I think one of the prevailing wisdoms from couples who are working together well in the real estate space is that the division there, right? That each partner has their areas that they are the leader on, and the other person doesn’t step on those toes. But what I’d love to hear from you is about your vision setting process. You’ve mentioned that a couple times, you know, when you guys first decided to go into this real estate space after the layoffs, and then you also mentioned it here with working together. I find real estate investors again and again when I’m speaking to newbies or people getting started, it’s not the strategy, it’s why are you in real estate in the first place? What is your vision? What are those values as well? And so what did that process of figuring out the vision values look like for you guys? And what did you decide was most important?

It’s a great question and it is fundamental, I would say. So many of us in our society here in the US anyway, right? We go to school and the agenda is set. There’s a curriculum, you follow it, you get into the workforce, you work for someone, and while you may have a little bit of agency within your discipline, the goals and the mission are largely set and you need to conform and drive that mission forward.

That was one of the biggest challenges for us when we shifted out of the workforce into entrepreneurship. You’re setting the tone, right? It’s your goals, it’s your discipline, your ethic. And Lydia and I both really like personal development and are deep into that. And so we already had the foundations of the importance of a why and a mission and a purpose and those kind of things. And I also come from operations where we went through regular strategy cycles and setting of goals. And so running the business came fairly naturally from that standpoint. But we work with a lot of clients today to help them start up their land businesses. And it’s the very first thing we do with people. It’s sit down, that’s our intake with new clients, to understand what is your why? What is your overarching purpose? It was essential for us in that first six months of starting our business, and still is today, but really in that period because you face hardships and obstacles and doubts. And if you don’t have the big why and purpose in front of you, it’s easy to stop and just say, well, I’ll just go back and get a job, this isn’t working, or those kind of things. But

We had that vision of wanting a life of freedom. Lydia’s from Europe. Her family all still lives in Europe. We like to go once a month where we can spend four to six weeks on a long visit where she can catch up and see people and make the long trip worth it. And so all of those things are difficult to do when you’re working for an employer.

Those kind of things really drove us in those early days. And they still do today. I mean, over here on the wall, we have a poster board with our whys on it. And it’s about family and experiences and being able to give back and do things. And ten years into our journey as entrepreneurs, it would be really, really hard, I never say never, but it would be really hard to go back and work for someone else and drive their agenda and just kind of have that sense of freedom constrained. But it is, I would say, probably the most important thing you can do as a business owner or an entrepreneur, or even just a person and a couple in life. I think it’s essential to a harmonious, healthy marital relationship to be able to have these shared goals and visions.

Right, it really is. And everybody has their own specifics, right? And yet I would say the themes I see a lot are the time freedom and location freedom, right? Like you guys wanting to go back to Europe to see Lydia’s family. I travel internationally full time with my family and it’s really cool to be able to say my kids have been to six continents and I don’t know how many countries and things like that. Everybody has their own thing and yet I feel like time and location freedom are what I see a lot. I’m kind of curious though, when you sit down and do these exercises with people who are coming to work with you on this land investing and you’re going to help them, what do you see or what do you often have to counsel or advise them on?

Well, everybody’s as unique as you mentioned. There are themes, but their flavor is a bit different. The common themes that I see are really about perspective. Just having a vision is one thing. The time and the runway to get there is another. And so that’s where we bring in some experience as it pertains to land, more on timing. I’m also not a believer that, I mean, we’ve had clients who come in and go faster and further than we have just because of their nature. And then the flip side of that is there are others. Spousal or partner relationships is another because a lot of times one person has a vision or dream and it’s good to have your partner at least aligned on where you want to go. And so there’s some checking there in terms of is everybody on board? Because that can cause some disharmony on the opposite side of things. Those are probably a couple of the most common checkpoints that we have when people come in. But I would also add maybe an element of richness. I mean, it’s really good to build out your dreams in vivid detail, the textures and all the different things because it’s the emotion that is really going to pull people through and drive them. So those are probably a few key factors that we key in on.

And I love that last point. It’s so funny. As somebody who’s been an investor for a long time and worked with a lot of investors in various capacities, it’s funny because investors always act or think that they are super logical, right? That it’s all about the numbers or it’s all quantitative. And yet when you see an investor taking action, right, or if you can be self aware enough to see it in yourself, there’s so much emotion that comes into play, right? And the emotion is really what drives us to do the hard things. So I love how you hit on that with the vision.

Thanks. Yeah, it’s very true. It’s a little less so in land, but in the other commercial real estate ventures that we’ve been in, and even land, there can be these desires just to get the deal, to make it a good deal, but there’s also the doubts that come along with it. Is it going to be a good deal? What’s going to happen? And those kind of things. And that’s where I think if you have a more powerful lever to push through those obstacles, it really helps drive things forward rather than getting paralyzed by some of the negative aspects of the emotions that can arise.

I love that.

Now I’d like to pivot a little bit, Mike, to something we touched on at the beginning, and that’s your investing strategies and the strategy behind choosing these strategies, right? Like we kind of talked about the multifamilies for the tax benefits and everything. So I realize you’re focused on some land investing with multifamily for its own benefits. Can we talk about the role each one plays in your overall portfolio and how you decide where to deploy cash? Capital.

Yeah, it’s great. So when we started our journey, it was land and obviously you don’t want to diffuse yourself too much over one pursuit. And so across the different journeys that we’ve had in real estate, we follow a similar approach. Like we invest in coaching or mentorship groups.

And so when we started our land journey, we invested in a coach, we joined a community so that we would go faster, make fewer mistakes. But very quickly, within, I think by our third tax year, which was our second year in business, we started making a lot of money. And that first tax bill that came was shocking. Our first year was a growth year. We were investing into the business, took a natural business loss because the revenue wasn’t caught up. But then once that tax bill came, it was shocking and it was something that I did not want to do again. And so we started looking at how can we mitigate this? And we went on another journey. And that led us into multifamily. There are obviously many different ways to enjoy tax benefits. There’s energy sector, different commercial assets, even storage and different things like that. But we took multifamily just because it’s an essential need in our society, right? Housing. And we did the same thing. We joined a community and found a coach and ramped up in multifamily. Today I would say we have kind of started thinking more future forward. And so land is still our core. It’s a huge cash cow, we’re able to deploy capital and get large returns. It funds our, we have our own self-directed IRA, which we use to invest in other forms passively. But in terms of now we start to look forward, land our land business is a flipping business. And so we are constantly looking at and doing deals. A big portion of our sales strategy is we do owner financing. And so we have like five or six years with clients and we’ve built up a passive income book, if you will, but it’s a monthly recurring revenue that comes in, but it’s also finite. They’re going to pay off their loan and we’ll transfer the title. And so we’ve started looking at longer term assets that we fully control. I didn’t like the syndication experience from the aspect of so many partners involved in a deal. And so we are looking at things that we either fully control or maybe have a small joint venture that we’re working with so that we have a lot more decision-making ability if we want to hold something forever or if we want to exit, we can do those things. And that’s smaller multifamily units. I like the light industrial and business spaces in real estate as well, but it’s very cyclical and market-to-market dependent. So it’s a little trickier in that way. But today we’re probably 90% of our capital gets deployed back into land. And we start looking at another 10 to 20 to do one or two deals a year, really with this intention of building a longer-term base that when we want to stop, if we want to stop, we have the passive income that’s coming in that supports, you know, most of your viewers might know, but once you get a certain level of income coming in that covers your essential needs, it really opens up the possibilities to be able to explore other asset classes or personal pursuits or things like that. And so that’s what we’re looking to have secure for the long term.

But that’s kind of the way the portfolio mix, at least today, is that we go about thinking about it.

I resonate and it makes sense to me. So I hope that helps our viewers as well. And then one of the last things I want to touch on as we near the end here is the operations. You and your wife, you guys are obviously very capable and organized people. I can see all of that. And yet you’re doing your land flipping. Flipping is intense. You guys are helping other people. So you’ve got your coaching program and then you also are looking at this other leg of more long term investments and vetting that, managing it, all of those things. What does that operations look like on the back end? What pro tips or wisdom would you give to viewers who often real estate investors struggle with how to organize all that?

It is systemic in real estate. I talk with a lot of people that are already in real estate in some fashion or another and they add land to their discipline or their asset class. But I don’t know, 80% of people that I talk to have created a job, right? They’re the hustler. They’re the one out there doing the things. Having an operations background really has helped me in this sense in that the top line is certainly a focus, the revenue that’s coming in, but there’s really a sharp focus, and there always has been for us, on the bottom line, the expenses, putting in systems. And one of the things that we’ve done since we started our business is we continue to update essentially a process flow chart of the activities that are happening.

And if people are familiar with the swim lane concept where you have these are things that I do, these are things that can be automated, these are things that are delegated to a human, now we have AI, it’s a great way for me to visualize the processes and where the opportunities are to move things out of my lane. And so it’s something that has helped us in the short term, but then also down the road, you can say, okay, my next piece that I want to work on moving would be this.

Mm-hmm.

In the land business, it’s really pretty simple in terms of the end-to-end process flow. There are also, as with most real estate asset classes, a lot of land specific systems. And so we do a lot of direct mailing outreach. Well, there are systems where you can do that kind of one time, set it and forget it, and let it meter out over months or weeks or however you want to do it. And so we leverage a lot of systems like that. We also leverage humans. Easy things are realtors. They’re commission-based. We can use that without any upfront out-of-pocket expense. Title companies, very similar, right? They do a lot of the heavy lifting in terms of due diligence, title insurance, escrow type services. It’s well worth paying them to take a big chunk of the process out. There are land-specific virtual assistant groups or businesses that know the land business and will take pieces or all of it. It kind of depends on your budget. We’ve leveraged virtual assistants now and again to do certain things. I come from one that has a mantra of eliminate, automate, and delegate and in that order, right? So first you look to can I eliminate certain processes? Is it essential? Beyond that, can I automate it with a system somehow that’s more cost effective? And then as a third category, it’s more delegation. Do I need to find a team member or pay a contractor or something in that nature?

Right.

On the multifamily side of things, it’s a little more self-contained. There’s not a whole lot of activities. If we do a lot of marketing, we might leverage graphic designers or people to be hands-on in our social accounts or things like that that are more tedious or repetitive type tasks. Those are easy targets. A lot of people are probably familiar with Dan Martell and the buy back your time concept. There’s variations of all of that, but it’s essentially where is my time best suited? What are my high value add activities? Is it sales? Is it some type of strategic analysis or things like that? And then other things find an outlet for something or someone that’s got more passion even about a certain task. And that’s been our philosophy. It’s still, if I’m honest, it’s something that I struggle a lot with. I like to have my hands on a lot of things, even if I know I’m not the best person to do it. It’s just something that I have, you know, we’ve hired a contractor, a few people, and you don’t have a good experience. And so it is a hard hurdle for a lot of us to get over. And it’s something that I have to intentionally work on. But I like to do things with my time. We live in the mountains here in Colorado. I like to go for hikes or trail runs. We travel. And so in order to do that, you have to let go and allow other people to pick up tasks. It’s also, if you’re going to grow, you’re going to hit a plateau if you’re doing everything in your business yourself.

In that same way, financial leverage is another aspect of things, right? I mean, you can only grow so far with your own capital. And so that’s one of the beautiful things about real estate, you can leverage private money, institutional capital. There’s so many different ways to apply leverage in the business in a healthy way. And so that’s just another great reason that I love and stay in real estate. There’s kind of in both those domains.

Right.

Yeah, that reminds me, one of the things we have, we travel and it’s always like, would we want a place here? And yet in a lot of other countries they don’t have mortgages or you can’t get them easily as a foreigner or things like this. And when I look at the mortgage options or the lending options we have in the US, I’m like, it’s just hard to even imagine putting all cash down on one of these places elsewhere. I’m just like then my appreciation is only one X. I don’t get that multiple of the fact that I’m leveraged along, so that’s where we are. But last question I’d like for you, Mike, before we wrap up, kind of along those same lines of your operations, you seem like the type, you mentioned AI. I love to hear where are you loving to leverage AI in your investing right now.

Gosh. Well, like most people, the start of the journey is in task. A lot of us leverage AI to help us do things, right? So we’re creating content or even graphics these days. There’s this collaborative type level. And that was our starting point, was doing a lot of that. Now lately though, I’m getting more comfortable with leveraging AI to do some analysis on the comparative analysis and look at things. It is so powerful statistically. In fact, I just published in our coaching group, we have a course AI for land flippers, where I’m building out kind of this end-to-end suite of tools where AI can help with market research, comp analysis, as well as some of the other marketing and sales type activities, sales coaching, to give you feedback on whether it’s a DM conversation or a transcript from a sales call. There’s so many different ways, but lately I’ve been leaning into the power of statistical analysis, but it’s one of those where you don’t want to outsource your thinking to AI just yet. I don’t have the confidence in its reasoning and its logic. And so there’s a fundamental knowledge that I try to teach our clients to have before they leverage so that they can double check and check things out. But yeah, AI is definitely a powerful thing, and it’s here to stay.

But really across the board, there’s very little that it’s unable to do. It’s just, I can remember twenty-five years ago when I started my corporate career, there were certain concepts. Things were starting to be outsourced, other people were allowed to do things, but there are some strategically competitive advantages that each company has, and it’s a little bit different for each, but it largely is around the thinking and the strategy that you set for your company. And so those are things that I try to hold on to. But we leverage AI daily, end to end. In land specifically, not so much. We do a little bit of market research. It’s nice to strategize with it as a partner in terms of what asset classes might be better suited, given the different variables that we want to put in. It’ll help point in a certain direction. But for now it’s kind of at that level, not really full advisory, but just some starting out guidance.

Right, that makes sense. Thank you for sharing that. And now Mike, if people would like to connect with you further or learn about working with you, what’s the best way for them to reach out?

Yeah, if anybody wants to hear more about land or just reach out personally, I would say LinkedIn is where I’m most active. It’s Michael B. Deaton on LinkedIn. But Instagram is also a great one because you can have good DM conversations and I’m happy to share some free resources on land. Those are probably the two best sites for people to come and connect with me.

Perfect. And guys, we of course have those links in the show notes below. So thank you so much, Mike, for joining us. That’s a wrap on today’s episode. And if you got value from this conversation, it would really help us for you to leave a review wherever you may be listening. And then join me again next week for another episode. See you then.

The post Eliminate. Automate. Delegate. The Order Matters. appeared first on Adrienne Green.

What happens when the system running your short-term rentals works perfectly, but only because you are the one holding it together? In this conversation, I sit down with Beth Turner, founder of SimpliHost, to unpack the exact moment a host realizes their setup cannot be handed to anyone else. We talk about her accidental start in real estate, the seven duct-taped tools she used to run her properties, the handoff test that exposes where your business is really just living in your head, and why the two tasks hosts cling to longest are the ones they should let go of first. If you have ever felt like your rentals are managing you instead of the other way around, this one is worth your time. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Here is the summary paragraph followed by the cleaned transcript.

What happens when the system running your short-term rentals works perfectly, but only because you are the one holding it together? In this conversation, I sit down with Beth Turner, founder of SimpliHost, to unpack the exact moment a host realizes their setup cannot be handed to anyone else. We talk about her accidental start in real estate, the seven duct-taped tools she used to run her properties, the handoff test that exposes where your business is really just living in your head, and why the two tasks hosts cling to longest are the ones they should let go of first. If you have ever felt like your rentals are managing you instead of the other way around, this one is worth your time.

Hello everybody, welcome back. I’m Adrienne Green and today we’re with Beth Turner. Here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start, and Beth is a perfect example of how to do that. So thank you for joining me, Beth. Welcome.

Thank you so much for having me.

Beth, for those who don’t know you yet, can you give us a quick picture of your short-term rental portfolio? How many properties, what markets, and how did you get started in it?

Well, I have an interesting start, but currently I have just one remaining in Wisconsin. Otherwise, I’ve had up to four of them. They’ve been in Minnesota, Wisconsin, and then I did a journey of some flipping, flipping fixes. I’ve done the journeys of also still own some long-term rentals. But how I got started in real estate was a complete accident. I am a huge Milwaukee Brewers fan, and my mother and I would go down to Arizona every year for spring training, and we’re probably like, or three years in a row we had host cancel on us last minute. This was before Airbnb, it was still HomeAway, it wasn’t even VRBO yet, and my brilliant mind was like, fine, I’ll buy my own condo down here. I flew down there just thinking I’m just going to look at it. I messaged a realtor online, never met them in person, we went to the very first house and he was like, somebody canceled their building contract, and he’s like, if you don’t buy this, I will. I was like, I didn’t even bring my checkbook, this is the days of the checkbooks, and he’s like, don’t worry, I’ll go get you the deposit. He took me to his bank, gave me a thousand dollar cashier’s check. I was like, do you need my ID? Anything as collateral? He’s like, no, you look like good people. And so I bought a condo. Called my mom and I was like, I bought a condo. She’s like, I didn’t think you took a checkbook. I said, I did it. And then realized, oh, I don’t live here in Arizona. So what am I going to do the rest of the time?

Wow.

And so that’s how I became an accidental STR host. I was like, well, I guess the best way to do this is to rent it out. And so I did that process and learned hosting in the roughest, roughest way of total trial by error. And I did it all remotely. I lived in Wisconsin and Phoenix, Arizona is where my condo was.

I love that. I just love this whole story. I’m a baseball fan. Baseball analogies are my go-to all the time. We’ll probably have some in here. And I love how you solved the problem. You solved the problem of, I want a place to stay. That’s amazing. And I assume now, with everything you do that we’ll get into, you’re really helping other people so they don’t have to learn through trial and error.

Yes. That is realistically pretty much where I’m at in my journey. I’ve gone through, I think the one thing that people can really realize is that help is totally fine. You do not need to do this on your own. There’s a lot of information out there as well. So you can get lost in self-helping too. So it’s okay to raise your hand and say, hey, I need a coach. I need a mastermind. I just need a group of people I can bounce ideas off of, whatever that might be. But there’s a lot of help out there, and how can we help streamline that help is really where I came into, and kind of where the journey I’m at now.

I love that. Now let’s continue through your journey. My understanding is you had a system that worked, but it was like seven different tools held together with duct tape, which we’ve been there. At what point, kind of like with getting the condo in Arizona, did you realize that this STR system issue was a problem worth solving?

So I had a bunch of other hosts that I was friends with and they would ask me, hey, can you set up my system to be like yours? And I was like, guys, bubble gum and duct tape over here. I’m techie enough where I had seven different systems. I was using Zapier to connect all these systems. I was using a texting system, a PMS, a cleaning system, a CRM, all of these things. But it worked great for me because it all worked and I understood all the little back ends. So if one would fail, I could go figure out where it was.

And so it worked great for me, but then I realized it wasn’t scalable for anybody else. There’s part of being on top of the mountain, like woohoo, I have some really great automation. But being on that mountain by yourself and seeing your friends struggle is not a fun spot to be in. And so finally, one of them, their first or fourth time, was like, why don’t you just build it the way that you built yours? And I was like, build it? I don’t know anything about software development. I’m techie enough to cobble these things together, but I can’t code. I don’t know what I’m doing. And this really started two years ago. So this was way before the AI world took over. So you really needed to code and needed to be a developer. And so I said, all right, we’ll figure it out. And we started figuring it out. And that’s where it came to the journey of, how do I help other hosts get back the time that I got, without super complex systems, without bouncing between seven different ones, and really duct taping everything together.

I love that, and I get what you’re saying. I’m curious, as you worked to build this new system, what are the key differences that you identified between a system that works and a system that actually scales?

So a system that works is something that can get you through to two to three properties. You’re still, a guest will text you on this system. They’ll say, hey, can I check in early? And you’re like, oh, hold on, I’ve got to look over the other system to see if they can or can’t check in early. Is the house really ready? So once you start getting to that point of, well, now I’m still the glue that’s holding this together, even though we’ve got duct tape and bubble gum in the back end, I’m still the glue that’s making that operation continue.

So once we start hitting that scalable point, I had another host ask me to co-host for them. And I was like, oh, I’ve got to have this be more systemized. I’ve got to be able to not just say, for example, they wanted to say, oh, can I come in and make a couple of changes? And I’d have to give you seven logins. There’s no way. I would love to have you in here, I’m not trying to be hidden, I want to be transparent, but girl, you’re going to have some fun in this system with me. So when I hit the point of I couldn’t help others, I also couldn’t scale past two or three of them because it was still me keeping the ball moving and me making those decisions. And then talking to these other hosts, I was like, this is definitely the point where we’ve got to get some policies in place and then procedures. And when I say that, people usually get scared. They’re like, I’ve got to create this manual that’s step by step by step. And it’s just as simple as, for example, we had some hot tubs at our properties, and if a hot tub had an issue, the first time it happened I was like, what do I do? Do I give a guest a refund? How much? We just put a policy in place that anytime a guest has an issue, it’s $50 a night for a refund if they have things. So it takes the pressure off of, what is my next step? And then it starts building that system that’s scalable. So when we hand those over to our VAs or to a property manager, they have that information so they’re not guessing either.

This is really resonating with me. I always view things as, I don’t want to solve the same problem twice. It’s okay to have problems. It’s okay to have issues. And yet when they happen, how can we improve our system so that next time it happens, it’s not a problem? We just automatically know what to do. And so it sounds like you are doing exactly that.

100%. For example, one of the things we built was an FAQ in our system. So like, do you supply firewood? Or is the grill gas or charcoal? Do we need to bring things, those types of pieces? Some of that stuff is already captured in the OTA. So your Airbnbs, your VRBOs, oh, they have a grill, but are they supplying propane? It’s a gas grill, but do we supply propane? So all those different types of things, to your point, we just need to keep iterating because there are so many things that one little guest will ask. But then now we don’t have to worry about answering and tracking down that answer for the next guest.

Yes, and for any short-term rental owner, they can totally resonate with that. I get asked all the time, even though it’s in our listing descriptions, what kind of grill it is. Now, you have something called the handoff test, right? If you had to give your entire operation to someone else tomorrow, what would break first? Can you talk us through that?

I think the handoff test, the biggest thing is how much knowledge is in your head. That is the easiest thing that it’s testing. How many things have you not documented yet or not put a policy in place?

So the things that are going to break are like not having a video walkthrough of your house, or not having a floor plan. So when somebody calls and says, where is this? It’s in that person’s head who’s the only one that’s walked that property. You can put together, it’s a gas grill and you bring propane. But when they say, hey, I can’t find where the electrical panel is because we just had a power surge, you’ve got to be able to give them that information. And so those are usually the spots of the handoff test. It instantly tells you where your system is not a system. It’s really just in your head.

And I would say the one thing for me that was the best handoff test is doing it remotely. I wasn’t there. I wasn’t the person that knew where everything was. So I had to go and build those systems. And remote usually scares the crap out of people. And I don’t disagree. If you don’t have the right kind of, not necessarily processes, but the right team and the right system in place, it can be very scary. It can be very stressful. But if you have the right team and you’ve got the right systems in place, it is a lot less stressful, because it forces you to put those systems in. So you’re not the cog in the wheel causing the bottleneck.

Beth, I totally agree. When we got our first long-term investment property, there were a lot of growing pains, because we couldn’t just run over and handle things ourselves. And yet that’s what really prompted me to start running my business more efficiently. So now I can run all my properties while I travel the world with my family. We are speaking the same language here. So let’s talk more about the tech piece. And yet, even with the tech piece, you do need a team as well. We need someone to run the tech, right? So at what point in a host’s growth does bringing in support, like a VA, a co-host, a property manager, someone beyond the cleaner and the handyman, someone who’s helping with operations, when does that become less optional and more necessary?

It’s when you want to change your lifestyle and when you’re changing your mindset. It’s also when you’re scaling. Those are the two pieces. So you might have somebody that got into this as just a side hustle and they really enjoyed it. And now they’re like, hey, I just want it to truly be a side hustle. I don’t want to grow it. I just want to step all the way out. That’s when you’re going to start looking at, do you want to have somebody co-host it? Do you want to just have a VA? Because when you’re also looking at the time, effort, and the cost of those things too, it comes down to, do I want to get a property manager or a co-host? Or can I just hire a VA to handle these onesie-twosies because I’ve built a really great system in place and I just don’t want to have any of those items?

For example, it might even be, I don’t want to be the one dropping off the Amazon packages or going to Costco. I just need somebody to go restock. That is not a full-time person sometimes. So depending on where you are in your lifestyle, to your point, if you want to travel all the time, you might just need a local college kid, a stay-at-home mom that wants a couple of hours to just be able to go and run and do those types of things that a property manager could do too, if you hired them, or you want to keep it all in house. So it becomes less optional when you make a lifestyle change or you scale. Once you start hitting that three to four mark from an STR standpoint specifically, that’s when you’re going to say, all right, do I want to be the one managing these? Do I want to be the one getting the guest message and responding to it? We also have great AI tools coming out in lots of different spaces. At the same time, they’re all still tools. So how do you want to leverage them? Do you want to not leverage them? And how good are they in all those different spaces? And again, AI is just as good as how much information you give it. So when we talk about building those systems out, if you don’t have it documented where your lockbox is, and a guest sends you a message at midnight that they can’t get in, AI can’t tell you where that lockbox is either.

Yes, I agree completely. Now, as somebody starts to grow with a team, they start to get someone else in there to do some of this work, what tasks or responsibilities are you seeing a host hold onto the longest? And what do you think is behind that reluctance to let go?

I would say there’s probably two, depending on where they are in their journey. One of the things as hosts that we don’t realize is we’re running a business. Because it always feels like a side hustle, no matter how big or small we are, until we fully quit our jobs. It’s not really a business, but it really is. And I think that’s a mindset shift that really has to happen. But for example, guest messaging and bookkeeping are always the two that I see hosts hold onto. Guest messaging is purely for the fear of, I’m going to send the wrong message. So for example, we had a guest that was coming in for a funeral, and I had anxiety of, I hope my happy automated messages don’t go out, like welcome, hope you have a great time. Until you have really good systems in place for that, because your normal guest automations will just send out a, we look forward to having you. Or you have to dial down your happiness in some of your pieces so it can be more broad. So when you’re building those automated messages, thinking of people that come for a birthday and a funeral, can you get that message across both ways? Sometimes not at all.

So it’s handing off those types of guest messaging. That I think is one of the biggest holdups, that they feel they’re going to miss something. I’m going to send something that’s not personalized, or it’s going to come across as, I kicked out an automated message and I don’t care. So I think a lot of the guest messaging, and then also making sure things don’t get missed. For example, the guest that sends a message at 11 o’clock, midnight. I better be up all night to make sure they’re getting checked in. I’ll check the cameras to see if they’re here yet.

So those types of things, guest messaging, and then bookkeeping, because everybody wants to hold onto their finances, but nobody really wants to do them either. I’ll have my weekly bookkeeping meeting with myself, and then it’s like, I can do so many other things. But at the same time, I don’t want to hand that off because somebody else will be in my finances. It’s one of those double-edged swords. So it depends on how comfortable you are with your finances. Anytime you outsource, it forces you to have a system and clean up your ways.

Right.

Because if I’m using my personal credit card for everything, including personal and business, that is harder to hand off to an accountant or a bookkeeper. And so it again resets and makes you think about your processes and what you’re doing and how you’re doing it.

Those are so true, both of those. The guest messaging, I know when I get a new VA, I’m always like, you draft the messages and I check them before you send them, until we know that everything is good, because you can’t undo them. That’s my concern there. And I have seen, yes.

Correct. It’s not like your iPhone where you can undo that message.

Yes. And I’ve seen behind the scenes with so many entrepreneurs, it’s so funny, because unless somebody has someone else doing their bookkeeping, they’re not up to date. And yet entrepreneurs hold onto it. Just like you said, I’m like, dude, just give it to someone else. Just make a system where you take a photo of the receipt and you email it to them, or you put it in a Google Drive, and they handle 98 percent of it with no extra input by you. And you’re going to be able to get an updated profit and loss and balance sheet and everything once you do that. And it’s so powerful when you have that.

And one thing you mentioned too is the VAs. So we also leverage them. There’s always conversations of offshore, bringing people in, I only want to hire local. And realistically, the one thing you have to think about is everybody is a person and you are helping them in any way that you’re doing that. So when we lift up others, we help them lift up all the people around them too. We have some people offshore, so we’ve got some in Bulgaria, Zimbabwe, we have some VAs in the Philippines, we have our key VAs all over the place.

It’s not necessarily, oh, I’m just trying to save costs, or I don’t want made in the USA. None of those things is always the driver in those cases. It’s also, how do I get this done efficiently and effectively? And then how do I also still help the people around me, even those people who are not physically around me? So when you talk about the VAs, you set up your people, you set up your systems, and then you trust but verify. And that’s that next step. Everybody thinks, we all think that we’re the best at everything we do. For the bookkeeping, I’m like, well, I’m the only one who can do it, but then I don’t do it. So we all overinflate our capabilities. And we also underinflate our time and how much we really have to knock out some of these things. So same thing when we onboard anybody. It’s just like anything, you give the training wheels. Think of when you change jobs. If I change to something as basic as I’m going to go be a bartender, they don’t just let you sign up and say, hey, go throw yourself in the weeds the first day. They still have you shadow, they have you train, they have these pieces in place to make not only the guest at the restaurant happy, or the guest at the STR, it’s to also set their people up for success. So there’s a kill two birds with one stone. You’re not only making the guest and the client experience better, but you’re also making the person and the employee experience better as well.

I love that, because yes, I think especially people who get into entrepreneurship, they get into real estate investing and they don’t have any business training. They don’t think about onboarding. They’re just like, yeah, they’re going to come and know what to do. And they don’t. It doesn’t magically go in their brain.

Yeah, like Mary Poppins is going to show up with all the answers.

Yes, exactly. All right, so we’ve talked about the people piece. Now let’s talk about the tech piece, because I would like to hear more about SimpliHost, this platform that you built to help solve the seven different tools with duct tape and bubble gum issue.

So again, we kind of started it because we really wanted to help. It just comes down to that. Like I said, the system that I had worked for me completely, but I couldn’t help other people get that time back. And one thing we realized is that yes, everybody has, we hear the term tech stack sometimes in the tech world, here’s my tech stack or here’s my system stack. Even though those things work in the regard of, my PMS will send my reservations to my cleaning system, my cleaning system will see that, and then create the cleaning task, there’s still time lost bouncing between those systems.

We hear, back in the day, remember when you put it on your resume, I’m a multitasker, and that was seen as a great thing? There’s so much research now that multitasking is really not a great thing. When you can focus and just stick to one thing, especially in the digital world that we’re in. I might get a text message from my guest in my one system. They’re asking me to check in early while I’m about to slide over to my PMS to see if the house is ready or do we have a back-to-back? I get an Instagram notification, or something else. Now I get distracted for that second. And especially I have ADHD, so that is very distracting to me. But we also lose our efficiency. We just lose some of our time bouncing between those.

So for example, right now, if I wanted to see in my previous seven-application system, a guest would send a text message, can we check in early? I would get that text message. Keeping in mind we’re always on our phones, so I’m traveling while I’m on this. I see this app, okay, hold on, I’m going to swipe that closed, I’m going to go find my PMS, I’m going to find the calendar, I’ve got to find the person that just sent me the message because the PMS doesn’t know who just sent me the message. And I say, great, yes, we can check in early. Okay. So then I’ve got to go back to the text system, send the message, and then now if I have a VA that is managing my PMS, they don’t know that I sent a text message over the text message system because they don’t talk to each other, only high-level talking. And so you start introducing all of these layers of inefficiency, as well as the siloed pockets of information.

So for example, the funeral example I had, I was like, I swear my guest told me they were coming for a funeral. I couldn’t find it in my PMS. And I was like, oh, I need to make sure that the wording has changed. I couldn’t find it in my PMS because they had texted me on my texting system. So now, if our EA wanted to, I said, hey, go through and just make sure everybody’s good from a funeral standpoint, or we have holidays coming up, let’s go and update some of those messages, they still don’t get the full picture. So we lose out on, yes, we have the systems that get us there, and we’re happy to the point of everything is automated, this tech stack really gets us there, but we still lose a lot in balancing between those different systems.

And you didn’t even mention that if you’re going to give that person early check-in, now you have to go to your digital lock, if you have one of those, and change when their code starts working on top of it too.

100%. Exactly. I go and send them a message, you’re good to check in, and they say, well, at what time? And I say, does noon work for you? And they say, actually, can we do 11? I have now bounced back and forth four to five times, and then to your point, they finally say 11, then I go to my locks and update it, or I go to my PMS that will update it, but I’m still in multiple systems.

Right. So what does SimpliHost do differently?

So it combines that whole scenario into one system, as well as a couple of other areas. So if a guest says, hey, can I check in early? There are a couple of data points that I need. I need to know, is there a back-to-back? Is the house ready? And are there any other pieces I need to know about this? Do we have a maintenance command coming during this time? Is anything happening right before that? So now when I get that message, number one, the text message comes into the same thread that they’re coming in from Airbnb, so I can see the whole conversation in one spot. If I say yes, I can see now in the top right-hand corner of my side it says the house is vacant clean, we are good to go, because it says that the cleaner finished their checkout task and their checkout cleaning, and it updated the status of the house automatically. And so then the last thing I can do is say, instead of a 3 p.m. check-in, it’s going to be noon, I update the time, and it automatically sends out the lock notifications to update that to noon as well. And then I can go, still all within the same screen, send the message to the guest, say yeah, we’re good for noon.

Awesome. That is a lot easier.

And that’s all without leaving one screen, which to me is even just the better part. I’m not even bouncing between multiple screens in the system. I’m in one screen that whole time, because we try to present that information all in one area for those types of scenarios.

So I can already see some differences with what you’ve built versus like Hospitable, which I use right now as a PMS, which does a lot, but it doesn’t include text or anything like that. And the other one I know a lot of people use is OwnerRez. So could you do a comparison, Hospitable slash OwnerRez versus what you’ve built with SimpliHost?

Yeah, absolutely. So for example, I also was on Hospitable. That was my PMS, because it comes with a lot of those pieces that I needed. Another area that I really struggled with is that we hand-write the welcome notes to all of our guests. And there was no spot for me to put that in Hospitable, or I had to create a separate task, and it was still all manual in doing those pieces. So when I’m looking at the system, we have special instructions, welcome message, and internal notes. So that is presented to a cleaner as well. When they go to their cleaning task, they can see, when is the next upcoming guest? Are there any special notes? What’s the welcome basket message? Those types of things. And so right now you have to utilize both Hospitable and something internal for their cleaning checklists, as well as create a task or do something manual to send a welcome message.

So the combination of those types of things is where we built in the same functionality, such as requiring photos, a full checklist, reference photos. So if I need to say, hey, this is what the kitchen should look like after you’re done, you can do all those pieces. So we really combine true built-in cleaning, inspections, maintenance, checklists, and that task functionality into one system. As well as the ability, one thing that we also hear people struggling with a little bit is that there’s not enough device connectivity in some of these PMSs. And so we partnered with another company called Seam, and they connect to over, I think, like 150 locks and a lot of different thermostats, even the noise monitors like Minut and NoiseAware, so you can check the battery statuses and set thresholds for all of your different noise monitoring. So again, all of that being in one system.

Yeah, because I will say right now, if there is an issue or I’m checking something, I’m going between Hospitable, Schlage, and whatever our system is for our cameras.

Yeah. That’s one thing that’s also coming down the pipeline, Ring cameras are coming in through this company Seam too. So we can then check, see how your battery is doing. Right now I still manage that in a separate system. I’ll get a message from Ring saying 716 front door battery low, and then I have to remind someone, send the cleaner a message to do that. We’re hoping to automate all that as well in the future. So even garage door openers are included in some of these devices too. So if a guest calls you and says, hey, I’m having a problem with the garage code, I can’t get in. If you have some of those smart devices, I think it’s Genie and I can’t think of the other one, but they have the ability to open up garage doors. Again, from that side panel, the button, unlock, open up the garage door. Even from the standpoint of a guest with a lock, sometimes guests will try the same code and they don’t hit the one button that says enter, or the check mark button, and sometimes the keypad freezes out on them and they’ll be like, you’ve tried too many times, just a beep at them. Same thing, when we’re in our inbox and a guest calls, I can push an unlock button and it just automatically unlocks the door for them, lets them in.

That is nice. I love this. Now, how long has this product been out? How long ago did you launch?

It is new. I think we launched, oh gosh, I should know this off the top of my head. We only launched like a month and a half ago. So we are new to this space. But at the same time, it’s been a two-year journey of love to get us here. So it’s not necessarily something that just came up. I always love the overnight successes, it’s like 16 years of overnight success.

So it is fairly new. We have our founding members active right now. So we are fully available to anybody who wants to sign up and come and join. Right now, everybody’s being onboarded by me as well, because I want to get as much feedback as we can into the system. We are updating all of our co-hosting tools as well. So for those that co-host and want owner portals, owner statements, we will have those up in the next couple of weeks as well, to redo what we currently have from the feedback we’ve already gotten.

And I think you also mentioned OwnerRez. I was just talking to a co-host yesterday, and she helps new hosts determine, do they need a property manager, or can they still just self-manage? And she was saying it depends on if they’re just going to do it themselves. There are systems that have a very high learning curve, and OwnerRez is one of those, it’s a high learning curve. And so if you’re just going to be doing one and you’re just doing it for tax purposes, or you just kind of want to enjoy it, building out a really robust system is a little too much. And then same thing with Hospitable, there might be some pieces that they would really like, like not having to go to Schlage, not having to also go do this. And so we’re bridging the gap between those two, of not having as steep of a learning curve, and then also still having a robust system that does not require that steep learning curve.

The not having a steep learning curve speaks to my core. I was actually just looking for one of our other businesses at accounting options, and one I was like, this is interesting, and then all the reviews were like, steep learning curve, you need to probably pay someone to build it out for you. And I was like, eliminated, eliminated, no way. So yeah, you’re hitting all the right spots there. So if somebody is interested in learning more about SimpliHost, or they’re interested in connecting with you, what’s the best way for them to reach out?

So we have the typical Facebook, Instagram. So we’re at SimpliHost Inc, and it’s SimpliHost with an I, we’re still, nobody owns the Y, but we’re trying to get that website so we can at least direct people there. So we’re SimpliHost with an I. And then you can also get a hold of me personally at Beth Turner on Instagram as well as Facebook. So I’m always happy to help get the feedback.

And if we ever see spots, I think the next space that we might move into is a little bit of the MTR space, because I’ve also done MTR and there is not really a system that juggles both STR and MTR well. And so we’re always looking to say, hey, where’s everybody going? What’s everybody’s next steps? We have the base, feature for feature, we can go toe to toe with Hospitable, OwnerRez, Guesty, all of this, every day and all day. From a separation of what is different from us versus this group or that group, it’s usually going to be, how do we treat our customers? How do we want to keep evolving and growing? And then how do we actually get there? Is it, hey, thank you so much for giving your feedback, throw it in the back bin? Or how do we get that actual, hey, we hear you, we’re hosts ourselves, and we have this really deep connection to the host community, and how can we keep that moving? And that’s, I think, the thing that’s going to separate us from some of the other PMSs as well. But also just seeing this from a true holistic, I don’t want to be in seven systems anymore, guys.

Right. Yes. Somebody who’s actually done it themselves, and not like so many things in our world now are owned by private equity. Maybe they were started by someone who cared, but now they’re owned by private equity and it’s all about cutting costs, making them better to sell, IPO, something like that. That’s something I see in a lot of the businesses I deal with. And so I love this, being able to work with somebody who’s in it themselves.

Exactly. We call it in the SaaS world, software as a service, bootstrapping. This is where it’s just us. There’s no big investor that came in and gave us, we didn’t do rounds of funding or anything like that. It is just me and our funds doing this, and also just a passion to want to be able to help, and a passion to continue to create better systems to get people to buy back their time. We want to be able to help rental owners manage their properties without their properties managing them.

Right, totally, and that’s what we’re here for, because so many people get into real estate for freedom, and then they don’t get it. They get another job. More things to tie them down, less vacation time. So I love that you’re helping counter that. That’s what we’re all about.

Yes. I would say the only thing that I would part with, when people say, one of the biggest misnomers I think out there right now, is that STR is passive income. I don’t know who started that trend. It is not passive income. It can be, don’t get me wrong, it absolutely can be. But coming into this brand new, it is not passive income. There’s a lot of information out there. You have to set up these systems. Once you get these systems, it can be very passive, but it’s not day one out of the box, day 30 out of the box, that you’re just passive, getting the mailbox money that we hear about in long-term rentals. It is not passive income, but there are plenty of ways for us to help get that to passive income.

I love that. That is definitely resonating. Well, thank you so much, Beth, and thank you to our listeners. That is a wrap on today’s episode. Please join me again next week for another amazing episode with another awesome guest.

Thank you so much for having me, I appreciate it.

The post The Handoff Test Every Short-Term Rental Host Needs to Take appeared first on Adrienne Green.

In this conversation, I sit down with Debbi DiMaggio, a real estate professional with more than 35 years of experience, to explore the strategies, relationships, and mindset shifts that have helped her build a thriving referral-based business. We discuss everything from trust, networking, and client experience to delegation, virtual assistants, and the lessons she has learned over decades in the industry. Debbi also shares insights from her Mindset in Motion framework, stories from her career, and practical advice for real estate entrepreneurs who want to build a sustainable business rooted in relationships, integrity, and long-term growth.

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

In this conversation, I sit down with Debbie DiMaggio to talk about what it really takes to build a long-standing, referral-driven real estate business. Debbie shares how she has grown through 35 years in the industry, why integrity and communication matter more than almost anything else, how professional networking has shaped her referral engine, and what she has learned about support, mindset, and persistence along the way. If you are a real estate entrepreneur who wants to build a business rooted in relationships, reputation, and long-term leverage, this conversation is full of grounded, practical wisdom.

Hello everyone, I’m Adrienne Green, and today we’re here with Debbie DiMaggio. Debbie, thank you so much for being here with me today.

Thank you so much for having me. Excited to be here.

Debbie, can you give us a quick snapshot of your real estate business today? Who you serve, what markets you focus on, and how your business is structured?

Sure. I have been practicing real estate, this dates me, for 35 years. I started in my late 20s working in rentals in San Francisco before I launched into sales in the East Bay. When I say the East Bay, we are 20 minutes from San Francisco. A lot of people move to San Francisco, and then when they start to have families and decide they want a less urban life, they move over to the East Bay. There are a few different places. I look at San Francisco Bay Bridge right now, and it’s still city-ish, but people move here for the community and the schools. The whole East Bay is where I practice.

I also practice in the West Hollywood, Beverly Hills area. After my kids grew up and I became an empty nester, I do not golf. I do not have hobbies like that. I don’t play bridge. I decided, I think I’ll expand to LA because I love LA and I love real estate. I have freedom in that way. My son, who works with us, is in LA right now working one of our deals down there. Real estate is wonderful, and technology has helped us tremendously to be able to have the freedom that you speak about.

Our structure is my husband and I started working together in real estate before we were even married. We worked in rentals in San Francisco, started a leasing department there, and that gave us flexibility to raise our daughter and later our son. We were able to time-share the job. He would go, then I would go, and we bounced around. We were lucky to have my parents for support.

When we moved over and started to raise the family, we moved over to Piedmont and got involved over here in sales. We’ve always worked together. Then our son started working with us during COVID. It was kind of a COVID fallout. He was going to go back to Colorado where he went to school, then he got his license and decided to work with us in real estate. That’s been wonderful.

We actually launched a company in 2009 during the recession. Someone said to us, “It’s a recession,” and we were like, “Yeah.” But this had already happened. We were already in motion to launch this company, and so we did it. Speaking with my book, Mindset in Motion, we didn’t really think about it being a recession. We just had a plan, and we were going to execute. It wasn’t top of mind. It was, “This is what we’re going to do, and we’re going to do it.”

We had Highland Partners from 2009 to 2020. Then we merged with Orchard to be part of a bigger company. Now that we’re part of that, we’re partners in the company. However, my husband, my son, and I are DiMaggio Betta Group, and that’s how we work.

Fabulous. With this 35-year career, I understand that trust and long-term relationships are one of your core values. What does that look like operationally, and how do you protect that reputation as you grow?

Markets are different. People are different in different markets. But one of the things that holds true in real estate for Realtors is that the only thing we have is our integrity. Fair and honest dealings, always being above board. Our community in real estate is super small. You get to know people, not only now with all the conferences we go to and Zoom and the internet and all the networking groups that I’m part of. It’s a really small network. When you’re at the higher end, it gets really small.

You’re known. There are some big people out there who are known for not being good people. It surprises me day in and day out how they’re still getting publicity. You can watch and hear their story and what they’ve done, and they’re being sued, but they’re still out there. Integrity is what we have. That’s what keeps us in the long game.

People know that they will get an honest answer. They might not like the answer if they want to sell their house and we give them the price, but the market speaks. What makes it easier for us as agents is that when the market speaks, it speaks to the buyer, the seller, the agents. It’s out there. It’s public record. I can’t change the data. I can share it with you, and I can peddle it softly to you, but the data is there.

The best thing we have, the only thing we have, is our integrity. That’s what allows people to trust and come to us time and again.

Right. That leads into my next question. Lead generation, sales, marketing, and how we are going to get new clients is such a top question for real estate entrepreneurs, whether they’re agents or investors. It’s, “How are we going to get the leads that we need to have the business that we want?” There’s always somebody out there saying, “This is the way. This is the way.” You’ve built this referral-driven business. What systems keep that referral engine running without you having to chase it?

I’ve been in the business for 35 years, and things evolved in how I worked. When I was younger and raising a family, I was very involved in kid activities. I was surrounding myself with the kids and activities and being in the community.

I also talk about pivoting and adjusting and having to move through your next chapter. When my kids left to go to college and they grew up, my community shifted as well. You have to work wherever you are in your life. You have to reestablish your community and join new communities. You might outgrow one, and then something else becomes more interesting.

Building clientele is in community. We serve people that we know, like, and trust. Where do I start? I’ve been through so many chapters.

I started writing books after my kids went to college. I kind of fell into writing books. My first book, Contained Beauty, was photographs, reflections, and swimming pools. It put me into motion to stop being sad and to do something constructive so I wasn’t so sad that my kids were leaving me. I started meeting people in that environment.

Let’s fast forward to what I’m doing now because I think it’s so relevant, and not everyone is going to write a book and get involved in that.

In the last two years, I joined a BNI group, a business networking group. Had I known when I was 25 and started out in real estate that there were these formal business networking events, not just a cocktail party, not just a happy hour, not just an opening of an event or a chamber meeting, but completely organized business networking events where you are there purposely to refer one another, I would have done it earlier.

BNI is Business Networking International. It’s all about givers gain. I have always been that person. I’ve always referred naturally. People would say, “Why are you doing that? Why do you put so much energy into that if you don’t get anything back?” I said, “It’s just the way I am.” I couldn’t explain it. It’s just how I’ve always been.

I’ve always had that BNI mentality that givers gain. You give and you receive, not knowing that it was a real concept. It was just my nature. When I joined BNI two and a half years ago, I thought, “I’ve met my people. All these people do exactly what I do.” Of course, I’m always number one every month because I do what is asked of us to refer one another and do educational learning.

From my BNI local chapter, you can also connect with people around the globe. Then you can start to refer, and they can refer you anywhere in the world. It’s incredible with technology, Zoom, and all of that.

The other one I joined about six months ago is the BNI international group, just real estate agents. This is where the golden nugget comes in. First, join a BNI group or any networking group because they’re amazing. We’re all like-minded people, and we all want to give and help one another.

With the BNI Real Estate Group, our goal is to do one-on-ones, get to know one another, and refer one another.

When you work with a BNI person, for the most part, I haven’t met one who isn’t like me, passionate and wanting to help. I recently referred an agent in Scottsdale for a buyer for four to six million, but I like him and trust him and know he’ll do a great job. As soon as he showed those people, he called me that day. He wasn’t even home, and he called me and said, “Thank you so much for the referral. They’re great. We had a great connection.”

That made me feel good because if I’m going to refer someone, I want to make sure they’re going to take care of them the way I would take care of my client. In a nutshell, professional networking is not like anything else because it’s not walking into a cocktail room not knowing anyone. It’s walking into a room full of people who are like you and want to help.

Great points. I love that. We’ve talked about how you get that business in. Now let’s talk about your operations and how you serve that business. At your level of production, what does your support structure look like for that real estate team? And how do you know when it’s time to stop doing things yourself?

That’s hard when you’re speaking to a control freak. For a long time, I did everything, and I didn’t have a calendar. I had it all in my head. Now I’m getting better. I’ve been working on a calendar, and I hired a virtual assistant in the last six months.

Now I have a podcast, I have a book, I’m getting all kinds of inquiries now, and I’m full-time in real estate. I’ve hired a VA. I tried to hire one that wasn’t local, and I know the price is so much better, but for me, I have to be able to see someone. Even though I don’t see her all the time, she is in my BNI group, so I see her every Wednesday. There’s no communication gap. I can rely on her.

I’m not saying you can’t rely on a virtual assistant who is out of the area. I think it just has to be the right connection. She is on it, and we have the same time zone. I don’t know how VAs would work on a different time zone. It’s been really great. She’s very responsive. She understands my abbreviated questions or thoughts that come out of my mouth. She can figure out what I’m saying. She kind of understands in advance. She doesn’t forget things, so that’s super important. I’ll say something, and she’ll bring it back up. Maybe I forgot, but she brings it back up. It’s really important to have that.

Of course, having a transaction coordinator for your deals is super important, so we’ve had that forever. In the beginning, you’re doing most of your paperwork to learn. I think right now the problem is newer agents aren’t learning because there are these TCs in place that are doing almost everything for them. That’s kind of a blessing and a curse.

Having a transaction coordinator and sending all my papers means I can be out meeting people. Today I’m going to go meet the manager of a senior center because I also serve seniors. I’m a senior real estate specialist.

With my structure, my husband, my son, and myself, I’m kind of out there. I’m getting the house ready for market, doing the design, meeting the contractors, et cetera. My son and my husband like to be at a desk. I like to be all over the place meeting people. I do a lot of one-on-ones and building relationships and referrals, but they’re super great on the follow-up and the contracts and the disclosures. Not that they don’t do everything, but that’s how it lands with us. I’ll do the marketing, and I’m trying to get my son now to move over to do more of the websites and that sort of thing.

Recently I’ve started working with a graphic designer. I do a lot on Canva. I love Canva. We can talk about tools in a minute, but did I answer your question?

Yes. You see the value of bringing other people in and having them bring their skills that complement your skills. That’s really nice. I know client experience is also important in the kind of clients that you serve and the price point that you serve. How do you protect that client experience while still leveraging your team and having other people start to handle some of that work?

When I bring in a client, when I’m starting to work with a client, I am always right there to speak with them. We’ve never really had a buyer’s agent. I don’t understand how people do that because if it’s me and my husband, and now my son will do it too depending on if there’s a schedule conflict, I try to be that first point of contact. If it’s my client and I’ve brought them in, I like to be that first point of contact.

Let’s say there’s a disclosure we’re going to send out for a buyer. I’ll include the team on that, and I’ll introduce them to Adam or Chase, but they’re family. It’s different than someone else. It would be really hard for me. I know I should maybe have buyer’s agents, but it’s really hard for me to let go because I am such a mother, and I want to take care of those people.

I will introduce them to my team, and sometimes they’ll show a property if I’m unable to, but it’s gentle. I’m always there. I always say, “Text me, call me, email me, but text me for a quicker answer. I want to answer all your questions.”

I think one of the biggest things and one of the most important things is that it’s a really stressful time for a buyer or seller, so they need answers right away. People know no matter what time it is, I’m going to respond. If I see that coming through, I will respond. I don’t want them to wait at all.

When I’m working on a deal with an agent on the other side, and if they’re not responsive, it’s very frustrating. Communication and collaboration are so important. I have something called the Five C’s of Real Estate. Communication and collaboration are so important.

I’m working with a client right now, and she said, “I didn’t want to call you. I don’t want to bother you. I know you probably didn’t know the answer yet.” I said, “No, as soon as I got the answer, I called you. I didn’t want you to wait, but you can always call me. Don’t worry about that.”

You have to say that over and over again because sometimes clients feel like they’re bothering you. But if you don’t keep them in the loop, they’ll get frustrated, and you don’t want them to do that. When it is time to talk about something important, you want to make sure that you’ve kept that communication open so they’re not frustrated by the time you call them with perhaps bad news. You want to keep that relationship going.

Great. Now let’s switch and talk about your book and what it contains. My understanding is that this Mindset in Motion Method is a five-step framework for aligning your vision with execution. Can you walk us through that framework?

Absolutely. The framework is called the Mindset in Motion Method Framework. It can be used for anything from excelling in real estate, conquering a personal goal, a business goal, overcoming an addiction, going through divorce, going through the empty nest, going through any transition, as well as elevating yourself and pursuing a goal.

The five steps are this. The first one is you have to establish a goal, and you have to be crystal clear around that goal. You can have a lot of goals, but start with one and be really crystal clear around that goal.

Number two is you have to believe. I don’t care how you’re going to get there. Just believe it will happen.

Number three is internalize. You have to feel that goal. What’s it going to be like when you achieve that goal? See yourself in that goal. This is where you can start doing a collage, Pinterest, journaling, but start to really internalize that. What is that goal going to be? What is it going to be like to achieve X or get through X?

The next one is share. It used to be just share, then I changed it to share with supportive people. We can’t share everything with everyone because people might think you’re crazy, or they’ll think you can’t do that. You don’t want negative naysayers in your mind. You need to only share with supportive people.

When I decided a month before the LA Marathon that I was going to run the marathon, and I had not trained for it, do you think I would have shared that with everyone? No, because people would be like, “You’re going to be 60. You don’t train. You barely eat right. How are you going to do that?” I did not want that. I was trying to prove to myself that you can run a marathon on mindset alone.

I did read stuff. I listened to books, audio, YouTube on the military, not on running. I was thinking, how does the military, how do these soldiers become superhuman? How do these Navy SEALs do what they do? That’s how I trained myself, not physically. I had to share it with supportive people.

The last step is to activate. This is the tough part. This is the place where people ask, “Do I really want that goal? Do I really want to do that?” Or people going through a divorce sometimes get stuck. Activation is the hardest step, but this is where you have to bring in all your supportive people and mentors and accountability partners and coaches, family, whoever is going to support you and be your cheerleader.

I talk about in the book, too, that you can reach out to people you do not even know. No one knows what you need until you ask. I’ve done that a number of times, and I have a good friend in Bob Burg because I reached out to him.

I love that. Of course, I’m also wondering, how did the marathon go?

I crossed the finish line, and I burst out into tears. I do not know why because it wasn’t a goal like having a baby or anything like that. For me, it was, “I just want to prove you could do it.” But when I crossed that finish line, I burst out into tears. What did I just do? It was pretty amazing. It was kind of crazy.

I have to share something with you right now because I believe, and this is in the book, that when there’s something in my mind or something that I’m considering doing, oftentimes if I’m going to do it, it shows up. This just happened this morning, and I’m going to unveil it here. I do not know what will happen, but it will be documented if it does.

Because of my book launching number one bestseller on Amazon, I’ve been getting a lot of emails and a lot of opportunities, which has been incredible. But I got an email today, and I have about 600 emails I’m trying to get through. This one was from the Great Adventure Race, inviting me to seven continents, seven marathons in one week and seven days. Private flights, first class, et cetera.

First of all, I’ve only run a marathon one time. I did not train for that marathon. So I responded, “That sounds amazing. Thank you for the offer. However, I would need a sponsor.” I didn’t say no. I didn’t say I don’t want to do it. I said I would need a sponsor. That’s where I left it. We’ll see. Of course, I did a deep dive on their website to even know what this was.

I don’t know until I know, and it’s a possibility. One of my quotes I always say is, “Look for the extraordinary in the ordinary. That’s where the magic lies.” We’ll see.

It’s great what opportunities present when you’re open to them.

Yes, and what happens is a lot of times people aren’t on the lookout. They might be looking at their phone. They’re not paying attention. Every day when I wake up, I’m thinking, “What is that cool thing that’s going to happen?” Not one thing. It could be big or little, but I’m always on the lookout for the magic.

That leads right into the next question I had. I love the framework. That is something for people to use to level up their mindset. What challenges do you see? What are the mindset traps that you see a lot of people in the real estate space fall into before they figure out that Mindset in Motion Method and start using it?

The biggest one is, because I just interviewed a coach and I asked her the question that annoys me the most. I said, “What do you say when people say to you, ‘I don’t have enough time’?” That is my biggest pet peeve.

We cannot control time. We can manage our time. If it’s a priority, you will implement and take action. Everyone’s busy. What you’re saying to me is one of two things. One is, if you don’t have enough time, you don’t care, and it’s not important to you. It’s not a priority, so let’s just stop there. I don’t want to coach anyone who says they’re too busy.

The other one that often frustrates me is “I don’t know.” Well, you can find out. As a coach and a mentor and an owner of a company, if someone has a question, I don’t care if you’re a new agent or a seasoned agent. If you have a question, you can call on me. You can call on our other partner. You can call on my husband Adam, who’s the broker. We will give you that answer. We will tell you where to find that answer.

Whatever the question is, you can probably ChatGPT it, Google it, ask someone, ask a professional. There are coaches all over the internet sitting there waiting to help you. You can ask them a question. You’re not going to have to hire them, but ask the question. Get the answer. It’s not hard.

People ask me questions all the time or ask me for a referral or recommendation. They say, “You don’t know me, but I know you offer advice a lot and you’re really connected.” It’s just part of my DNA. I can’t help it. Not everyone is going to be that way.

But if you’re speaking to a client and a client is asking you something, say, “I’ll get right back to you.” Get the answer. You don’t have to know everything, but you can find out. You can ask someone who can help you and point you in the right direction. “I don’t know” means “I don’t care.”

Very true. I feel like in this day and age, it is easy. We have information overload. Saying, “I don’t know,” is silly because we can find information easier than ever. It’s amazing. It’s so cool. My kids will ask me questions, and I’m like, “Well, that’s as simple as a Google search or AI.” Then I get to learn alongside them too, so that’s fun.

Absolutely.

What I would love, Debbie, is if you can walk us through a time when a deal or client or something did not go the way you planned and how you were able to keep that mindset and not fall into scarcity or worst-case scenario. What did that look like for you?

Let’s see, what would be an interesting story? I’m going to go back to communication. It really just takes communication. Whatever the story is, it’s about communication because miscommunication causes friction.

Years ago, I came up with this: we’re colleagues, not competitors. I had to explain that to my son and his friend once. He said, “Are you not going to be friends with my mother now because you’re at a different company?” I said, “No, we’re collaborators. One of us has a listing. One of us has a buyer. We need to work together.”

We’re collaborators, and we collaborate as referral agents with agents all over the world. We’re our biggest advocates.

I was working on a deal, and you have to think, what is the reason? Where’s the disconnect? I was the listing agent working with the buyer’s agent. The buyer was a woman. It appeared to be just a woman without anyone else part of that transaction. The contingency was delayed. The communication was not there. I kept calling the agent.

“Can you give me a call? Can you give me a call?”

She’d respond with a text, but there was nothing in there. I said, “No, can you please give me a call? Because I think if we have a conversation, we’re going to be able to get to the other side of this.”

I finally had to call her broker because the broker was a friend of mine. I said, “I don’t mean to tell on her. I just know if she picks up that phone, we are going to get through this.” The agent called me right back. I said, “Hey, I just want to know what’s going on. What’s the hesitation? Why this? Why that?”

She said, “My buyer’s father is very worried about her because of X.” Now we have someone else in the deal.

I asked, “Where is the father from?” She said, “Los Angeles.”

I said, “In the East Bay, different markets are very different. All markets have their own way of doing business. We’re in the Oakland, Piedmont area in the East Bay. He has a mindset of how they do business in LA.” Since I work in LA, I know the mindset of the agents, the sellers, and the buyers. It’s very different.

Once she said the father was in LA, I knew how to get through to the other side. I knew how to communicate with my client about what was going on in his mind. We were able to get through the deal seamlessly to a close, but it was only because she finally picked up the phone so we could have an understanding.

That’s the problem. Texting is great. Email is fine, but once in a while you’ve got to pick up that phone. Especially when you’re working with a buyer and it’s all new to them, you’ve got to explain things to them through the mouth, not just through text. You can say, “Yes, meet you at five o’clock,” or “Yes, this is this.” But when you have to go a little deeper, pick up the phone and make the call.

It’s so funny that you chose that example because when I was an active real estate agent, that exact issue would pop up. Not all the time, but when it does, your job as an agent is to facilitate the deal. But so many agents were like, “I just want to text.”

Exactly. I’m working on one right now. Thank God it’s not been a difficult deal, but to get them to pick up the phone is hard. I don’t understand why they don’t. Why are they hiding? I don’t know if it’s an age thing. I don’t know what it is. It’s bad.

I’m with you. I think it comes down to that “I don’t have enough time” issue we also talked about. People feel that phone calls take up time.

Debbie, as we wrap up here, what does the next chapter of your business look like? And what advice would you give to somebody who is starting where you were on day one, 35 years ago, and wants to be where you are in 35 years?

I had a 16-year-old come into my office. She was referred by a friend. She came into the office, and she was darling. I thought, “Wow, she’s 16.” We were having a conversation, and then all of a sudden she said, “Can I ask my questions?” I thought we were just there for a casual meeting and that she was going to ask me a few questions. She had two pages.

I said, “Sure, shoot.” She started asking, and I was answering, and we went down the list. Then I said, “You know what? I think you’re ready for my real estate book, The Art of Real Estate.” It’s very dense, but if you’re truly interested in real estate, then that’s where you go. It’s for buyers, sellers, anyone looking to buy or sell. It’s for agents, anyone, but it’s pretty dense. You have to be into it to want to read it. I gave it to her because she was so motivated.

One of the things that I’ve learned in my 35 years is be persistent. Don’t give up. People give up too soon.

We have one of our agents. He’s a flight attendant and an agent, but he works really hard. He doesn’t complain about time. He continued his day job or night job or overnight job, but he always shows up. When he first started, he was doing Saturday and Sunday open houses even though he was flying in at midnight, and he was showing property before the 2 o’clock open house. That is someone I’ve used time and again because he doesn’t complain about time. He’s always happy, and he just does the work.

When someone says they don’t have enough time, look at these people. They’re making the time. Be persistent. Don’t give up. Have a second job. Do something on the side while you’re starting. It can’t be something that takes too much brain power. It has to be something where you can make money because you have to be available to your clients.

One of the biggest things I can say is join a professional networking group. I feel like in 35 years, I’m so behind just starting six months ago in this BNI Real Estate Group. I’m like, “You guys have been at it for 18 years, and I’ve already seen results from it.” I’m so far behind the ball.

What my future looks like is continuing to serve clients, continuing to grow my referral business. I’ve done it forever, but I want to continue to grow. Through podcasting, and I have my own podcast, Mastering the Art of Success, I’d love to serve and refer more agents. I love referring like-minded agents to help my clients.

I want to speak. I’m going to be speaking at Luxury Real Estate, LRE, in Denver on September 28th. Most real estate agents know Luxury Real Estate International, so I’ll be the keynote speaker there. The press release is actually going out today.

Exciting.

Book me for a keynote presentation. I can do it on Zoom or in person. I don’t mind traveling. I’m going to be speaking at the next two Women’s Council of Realtors chapters, one on June 4th and one on September 17th. I’m open to inspire and help people elevate their business.

Perfect. That leads us to this. If people would like to connect with you, what’s the best place for them to reach out?

BookDebby.com. It’s D-E-B-B-Y. BookDebby.com. Thank you.

BookDebby.com. Perfect. We’ll have that underneath. Thank you so much, Debbie DiMaggio, for joining us. If you got value from this conversation, please subscribe wherever you’re listening and give us a review. It really helps me out. Join us again next week for another episode.

Thank you.

The post “I Don’t Have Time” Is Killing Your Real Estate Business  appeared first on Adrienne Green.

In this conversation, I sit down with real estate entrepreneur Robert Howell to explore how he built a thriving business around mobile home parks and land-home packages. We discuss his journey from event marketing to full-time real estate investing, the lessons learned from scaling a business, building remote teams, working with virtual assistants, leveraging private money, and creating affordable housing opportunities. If you’re looking for practical insights on growth, delegation, and using leverage to build a business that supports your life, you’ll find plenty of takeaways in this episode.

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Hello and welcome. I’m Adrienne Green and today I have with me Robert Howell, and get ready as we are going to talk about how you can escape the grind and get the life that you really wanted in the first place through real estate. Robert, thank you so much for being here with me today.

Thanks for having me. Excited to have this conversation.

Now to ground our listeners, can you give me a quick snapshot of your current real estate business?

For sure. I invest in mobile home parks as a long-term strategy and tax saving strategy. And that’s a great part of my business. I love it. I’m always looking to buy mobile home parks. And then second to that, really first to that, I should say, is my land home business. I buy raw land and put brand new manufactured housing on it, and then sell that land and the home together as a package.

You are the first person that I’ve had on the podcast, and we were talking about before I recorded, I think we’re on episode 94, who has done these land home packages. What I’m always interested in first is how did you get into this niche?

That’s a good question. If I back up the story a little bit, I started my career doing event marketing and traveled around the US, traveled around the world doing event marketing for Fortune 500, Fortune 100 companies. I was working actually in Tokyo, Japan when COVID hit. I was working the Tokyo Olympics for Coca-Cola and COVID hit. I was like, crap, what are we going to do?

I’ve got to do something different other than events, because there may never be an event again. And so I got into real estate. I said, I’ve always had a passion for real estate. I’ve owned a few rentals, not anything really that intentional, but I had bought a few rentals. And so I had pivoted at that moment. I said, hey, I’ve got to do something different. Started buying and selling, wholesaling really houses. As a result of that, I ran across a guy that owned a mobile home park.

And he said, hey, you want to buy this mobile home park from me? I said, I don’t know anything about mobile home parks, but I do know about affordable housing because that’s what I was really focused on. And so I bought that mobile home park. And as a result of that, I got my mobile home dealers license. And that allowed me to buy directly from the factory in order to get the best prices. And in South Carolina, you have to have a mobile home dealer. You’re supposed to have a mobile home dealers license to be selling more than two mobile homes a year, whether that be inside your mobile home parks or separate.

Anyhow, I got the mobile home dealer’s license. I was doing some house flipping by that point too. I said, well, instead of house flipping, maybe I should just buy land and put a new mobile home on land. And so I did that, started to do it, loved it. I said, I’m never going to flip a house again, because there are so many surprises with flipping houses, and started doing land home packages. It started slowly, probably did a handful a year. And last year we did 50 land home packages. This year in 2026, hoping to do maybe 100, we’ll see. But love it. It provides a need, doesn’t solve it but helps to solve the huge need we have in affordable housing.

Well, and what I love about your story, something we talk about a lot here is the process of going from, a lot of people are occasional or part-time or hobbyist real estate investors at first. And that often goes one of two ways. Not many people stay hobbyist real estate investors for decades. They either realize that to do it well, they’re going to have to put in more time and energy than they want to, and they sell their properties and get out. Or they lean into it and scale up, which is what you decided to do.

That’s right. And I’d left out, when I started, I was doing event marketing and I was buying and selling a little bit because it hit and we were still doing a little bit of events. In the meantime, I bought a roofing company. And so I had the roofing company really as my day to day. But I knew I wanted to do something a little bit different. I wanted to be an entrepreneur, which was in the roofing company, but still really had this burning desire to be a real estate guy.

And so I ran the roofing company really as my day to day. And then at night or on the weekends, I would be looking for mobile home parks to buy or doing land home packages. And then in 2024, I sold the roofing company and turned full-time focused on real estate.

Our journeys are often not like these straight paths. We always wish they were, I think. We can sometimes loathe the winding nature of getting to where we eventually end up, but that’s the most common one.

There’s no straight path, that’s for sure. Every day is a curvy road, how about that?

I know. To help us, because I think what I love here is you’re really a real estate entrepreneur. I think there’s a lot we’re going to be able to pull out as you’ve gone on this journey. To give us an idea, I’m curious with these land home packages that you do now or focus on, are you focused in a certain geographic area? Are you doing just South Carolina, just certain communities, or are you doing this all in person remotely? What does this look like in terms of geography first?

For sure. I do 90, 95% in South Carolina here in the upstate where I live and then down in the low country. But I have also expanded to, we’ve done a few deals in Tennessee, done a few deals in Georgia and North Carolina. So really the Southeast. I’ll do land home packages anywhere, but we really want to be the expert in the market. Don’t want to spread ourselves too thin. But primarily focused on South Carolina, we’ll do it in other states. And when you ask virtually or in person, in the upstate, it’s in person, of course, because I’m local here and I can easily drive around and see the projects. Down in the low country of South Carolina, that’s about three and a half hours for me. And so I’ll still go down there every other week and see the projects, but pretty much virtually on a day-to-day basis.

I love that. You’ve got your regional expertise, where you can really master and know that area well and that’s what you focus on. And yet you don’t have to be the boots on the ground going by the property every day or anything like that, like you might have when you were flipping. Now as you’ve grown and you continue to grow this year, I think what our listeners often enjoy is hearing about the things that broke and how you fixed them. So as you’ve worked to really make this a business and scale up, what were some of the things that broke and how did you fix them?

Learned a lot along the way, that’s for sure. Been doing this for several years now. One of the very first projects that we did, just to talk about things breaking, we moved a mobile home. We bought a piece of land, moved a mobile home on the piece of land. Our neighbor next door to the land said, hey, you can’t put a mobile home here. And sometimes we get that and people think that they just don’t like mobile homes for one reason or other. We’re like, don’t worry about it. You’re just a neighbor that’s mad. So we kept installing it. Well, finally, he serves us, or the HOA actually, come to find out there was an HOA that the closing attorney missed, sends a lawsuit and serves us with papers to say, hey, in fact, you can’t have a mobile home here. And so that was probably one of the biggest oops moments, like, man, that was a big mistake. But again, the attorney missed it as a deed restriction. We were able to secure title insurance payments for that piece of land, but it was still a big learning as we went. That was probably our biggest, man, that’s a bummer moment. But it worked out in the end. We sold the house, we moved it to another parcel and sold it and were able to still maintain a profit. But that was an interesting one for sure.

That is, and I think a couple lessons that I’m hearing there. First, and this is something that I have also seen in my own experience as an investor and an agent, the title attorneys or the title companies, they miss things. If you do a decent number of deals, you will have a time when they miss things, and that title insurance is clutch. And then the second thing is, although you’re in the middle of what seems like a disaster, typically it’s not going to be as bad as you imagine it’s going to be. You were able to move the house to another property. What did you end up doing with that land since you couldn’t put the mobile home there? Did you sell it as is or what?

The title insurance company bought it back, or took the land back when they made the insurance payment to us.

Perfect, so it was their problem then. Well, that is a good lesson learned. Is there anything, I know we often depend on these title companies and title attorneys to do their jobs. Is there anything you found where you can kind of check those yourself? Have you added anything to your process where you try to check any deeds or restrictions or anything like that?

Yeah, now what we’re doing is being very clear with our intent for the property upfront when we’re purchasing the property from the seller, in case the seller knows something. And then also with the closing attorney, making sure it’s very clear, hey, in fact, we are going to put a mobile home here. Just want to make sure there’s no deed restrictions. Because in this instance, this HOA that I was mentioning, it was only five houses on a very busy road that you would never suspect to have an HOA. And so now we’re just very clear on our intent and it’s part of our process to double, triple check with a closing attorney.

I’m curious, in Tennessee, because I was an active investor in Tennessee from about 2020 until we started full-time travel in 2024, it was such a trip when we moved to Tennessee because there are counties where unless you’re in an incorporated city, there is no zoning. There just is no zoning. You can do whatever you want on this land. And yet there would also be these HOAs in these rural areas that would have certain restrictions, you could only have a house of a minimum size, like a minimum size of 2,000 square feet because they didn’t want tiny places to go in, no mobile homes, only permanent foundations, all these things. What do you find in South Carolina primarily and around where you work, are there any kinds of restrictions on the land or zoning? What do you run into the most?

Typically, like you said, in a lot of counties that we work in, there is no zoning. And people ask me all the time, do you have trouble finding places to put these? But the reality is not that often, because the counties don’t have zoning. They’re allowing you to have the property rights that you deserve. But when we do find a restriction, it’s either because we’re in city limits and we found a parcel that’s in city limits, or it’s in an HOA, or there’s a deed restriction when somebody originally subdivided the land. And typically that deed restriction is going to say no mobile homes or no trailer. If it’s really old, it’ll say no trailers. Sometimes we get square footage requirements, like maybe mobile homes are allowed, but it has to be a double wide or it has to be 1,300 square feet plus. But it’s a very small percentage of the deals that we do where we run into those restrictions.

Well, that’s great. And for our listeners who are in other states, like maybe California or Washington state, I know it can be a trip to be like, my gosh, there are counties and there’s land where there’s just no zoning. You can do whatever you want with it. Yes, it’s there. Crazy as it is to imagine, because it’s very different from your reality in some states.

If you’re in California, make sure you check your zoning.

Totally. It’s a different world. Robert, let’s talk about one of my favorites, which is leverage. We can have a couple different kinds of leverage. I’d love for us to talk about how you leverage other people, how you have a team, things like that. And then we’ll get into leveraging with finance. But as you’ve grown, as you’ve established this business, as you’ve sold a roofing company, I imagine it’s not a one-man show. What does your team look like and how did you get there?

Yeah, when we started, to your point, it’s just a one-man show. A land home package, they are pretty simple, pretty light work. But as we’ve done more, once you get over the 15 or 20 deals, you need more people to help you in the office. So we have a project manager that helps us manage the projects. And then we have a team of virtual staff, virtual assistants in the Philippines, that help us with different aspects of the business, whether that be finance or maybe it’s just helping with the project management software or a sales assistant, work that can be done virtually. And then on site, we have a great team of contractors that help us manage a project. Typically we’ll have between eight to 10 subcontractors that will do their specific niche of the trade and we’ll work with them to get the project done. And really we’re managing our timelines, scheduling them, making sure that they do a good job. We have a great team. For the last two, three years, we’ve worked with the same contractors over and over again on every single project, so we really trust them, they really trust us, and it’s a great team. It takes a lot of different types of people to be successful and to manage the project.

I was going to ask, with you covering a large geographic area, you have that same team of subs who, will they travel a few hours to do jobs in different parts of the Southeast?

We have different subcontractors. For example, for the upstate it’s one set, down in the low country, which is about three hours away, it’s a different set. There are guys that are willing to travel, but what we found is based on volume and based on just capacity, it’s better to have a localized crew that probably travels within about a two-hour radius of a central point.

And especially with these teams that are not local to you, how did you find them? Did you strike gold and get a great one the first time, or did it take a few tries?

Took a few tries for sure. And as we’ve grown and scaled, the guy that we started with maybe isn’t a great fit. He’s a good fit for doing one home a month, but he’s not a great fit for doing five homes a month. And that has to do with capacity, but also maybe the equipment that he has. But in order to find new contractors, word of mouth is really key for us, finding people that are in this industry, networking with those people and finding out who are the best subcontractors that we can work with. And a lot of the times that comes from the existing subcontractors that we have. I think back to when we started, we’re still working with several of the contractors that we started with in their specific niche, and they’ve referred us to other great contractors. The grader that we work with, he was referred to me by another real estate investor for a job that wasn’t even related to land home packages, but he did such a great job that we’ve continued to hire him for other things.

It’s funny how when you get started, it’s almost just random. You’re going to get the random plumber or the random electrician, but then you get one that’s good and you keep them, and they’ll tell you, hey, I worked with a great electrician on this other job, you might want to get him in here or something like that. And eventually you build out that A team.

I feel like we have it right now, which is great. It makes our life easier. But that may change a year from now. People’s life changes and their business focus changes, or maybe capacity changes. But right now we have an awesome team.

Well, kudos to you. You have a lot of your team that’s remote, whether it’s the contractors that aren’t right in your backyard or it’s your remote team in the Philippines of virtual assistants. And that can be an extra level of management and leadership and oversight, to make sure they’re doing their job. Do you have any wisdom you would share with listeners to help them be successful with managing remote teams?

I’ve learned a lot of lessons along the way. For the subcontractors that are local in terms of managing them versus managing the virtual assistants, it’s two different management styles. But for me, it’s treating people how you want to be treated. And so the subcontractors that we have, we really treat them like partners, and I would consider a lot of them friends. How do you treat a partner? How would you want to be treated? You want to be paid on time. You want to be communicated to effectively and efficiently. I like to go on site and meet them and have conversations with them. Even though I don’t need to go on site, I like to go and have them be there and meet them and talk to them and see how their life’s going and how the job’s going, how the business is going. We also have quarterly celebrations where we’ll get the whole contractor group together and we’ll have dinner. Last quarter we went to a barbecue place and it was awesome. Everybody got together and they said, man, this is great. None of our customers have done this. And it was really great to spend that quality time with them, and they brought some of their kids and their family, which was really cool. From a virtual standpoint, with the virtual assistants, same thing. I think a lot of people think, they’re virtual assistants, they’re in the Philippines or wherever they may be, and maybe they treat them differently because of that. But the reality is they’re still humans, and they’re still trying to make a career. They just happen to be living in a different place. And so we treat them just the same way I would treat my coworker here in the US, respectfully. We communicate with them. I would hope that most of them would say, hey, this is the best job I’ve ever had, just by the way that they’re being treated.

I love that. The way you work with your local team, it’s funny, as somebody who’s originally from California, I’ve lived in Washington state, I’ve lived in Virginia, and then I’ve lived in the Southeast for a bit. The way you’re managing that team is so stereotypically Southern. Let’s get together, let’s have meals, let’s celebrate and be in community. And it makes a difference. It really does make a difference. And it’s funny, that’s what keeps people in jobs more so than a high salary or something like that. It’s the connections and the community that they feel where they work.

100%.

Well, let’s switch to the other kind of leverage that I know you use as well, which is financial leverage. You use loans, you use other people’s money. How does that look for you?

We do a lot of projects and we use other people’s money to have leverage to be able to scale. We use a combination of banks, private money, people like me and you that have been successful in business or in real estate that are looking to make a good return on their money. We also use some hard money companies. We have some good relationships with hard money companies and we’ll use them to buy the land and also develop the project. And depending on capacity, our first preference is to work with private lenders. We have a lot of great private lenders that we work with and we structure deals with them, here’s the amount that we need. Typically a project for us is 150 to 175K and we secure them financially against the land and against the development. So they have a first position on their notes and mortgage and they get a good return. Typically we’re paying between 10 and 12%. That’s the way we work with private lenders and same with banks and hard money. Typically we’re working with a lender for four to six months, which is usually the term. And upon success, they usually come back and say, hey, let’s do another project together. It’s a good diversification from the stock market to get a solid return.

You explained that so well, what exactly it looks like working with these. Now, sometimes investors look at private money or hard money and they look at these double digit interest rates, and that can give them pause. Tell me how you’re still making money while paying these loans at double digit interest rates.

That’s a good question, and I hear that a lot from early investors, having to pay 12%, or even hard money, you might pay 14%. And it’s like, that’s crazy. But what I learned early on is, don’t count other people’s money. If I can borrow money from you and that allows me to go and make, on average we’re making $30,000 or $40,000 profit after paying you, I can go and pay you. On average we’re paying a lender somewhere between eight and 12K, or eight and 14K depending on the project and the amount of money we need and interest. And after I’ve paid you as the lender and paid all my closing costs, I’m still making $30,000 or $40,000. That’s huge. And so I’m not worried about paying 10 or 12 percent, because at the end of the day I’m still making money, and I need to respect your money because you need to make money too. Am I strategically thinking about my funding sources and how I can get more competitive interest rates and expanding my private lender network? For sure. I think about that every day. But I’m not worried about paying 10 or 12 percent.

Right. And you said it really well. I feel like it’s often the newer investors who really freak out about that. I get it because there’s a little bit more of a scarcity mindset when you’re new to it. Everything’s a little scarier as well. Once you get into it for a little bit, you realize, hey, it’s a win-win. They’re enabling you to do more deals so you can make more money, because you can scale more than you could if you were only using your own funding.

Yeah, 100%. It’s the difference between, do you want to make some money or do you want to make no money? If my option is to pay a lender an interest rate and maybe some points to make some money versus I don’t do the deal because I don’t have money, then I’m going to choose to do the deal. Assuming I can make a comfortable and conservative profit, then I’m going to do the deal.

Exactly. As we wrap up here, I’d like to focus a little more on land home development. What sort of investor is land home development a good fit for?

That’s a great question. My opinion is it’s good for everybody. But if we’re going to niche down and think about who this is for, we work with lots of different types of people in our education program. I’ll just list some of the people that I’ve seen to be really successful. One is the wholesaler. You’re a wholesaler, you’re making good money, but maybe you want to go to the next level in real estate. This is a great opportunity. You know how to find good deals. Your next step is how do I learn something else in real estate to add additional value, make more money?

The second person maybe is a land flipper. We have a decent amount of land flippers. They’ve been doing land flipping, they have a lot of deal flow, they know how to find good deals on land. But maybe there’s some land that you haven’t been able to sell that you didn’t buy at a big enough discount in order to wholesale it, but it’s at a big enough discount where you can still be profitable in land home deals.

And then the last example I’ll leave you with, there’s a couple of guys that I work with and they’re really good friends of mine now. They’re in their 60s and they both had jobs, but they were kind of semi-retired, but they didn’t have quite enough built up for retirement and they wanted just a little bit of extra retirement income. And so they started doing land home deals and have been extremely successful in a different way than I have in terms of how they find deals, which is interesting to see. They’re now doing two deals a month, and their so-called retirement has built up so much so that one lives in Chicago, one lives in South Carolina, and the guy that lives in Chicago is now moving to South Carolina with his family. His wife is able to quit her job and they’re going to work together closely in South Carolina, which is really cool to see. So that’s another example of, hey, maybe you’ve got a W-2 or maybe you’re older and you’re thinking about retirement but you want to stay busy. Probably a good thing to look at.

Love that. Those are some really great avatars, examples of who’d be great for this. And is this something somebody can do in any state in the nation, or are there certain regions that are ideal?

There are definitely places that are better than others for land home packages. The way I look at it is, I’ll go to Zillow and look at sold comps. And typically I want sold properties to be above $225,000 in order to be profitable. The Southeast is really good, Texas, but there are people that are doing it in California and people doing it in North Carolina. And there’s a guy I know, he lives in Texas but he’s doing deals in Florida, or there’s a guy that lives in Boston and he’s doing deals in Tennessee. Geography doesn’t necessarily limit you in terms of being able to do land home packages, but of course there are better places than others to actually execute.

And that’s great to hear. You can do it in a totally different state, 100% remote. And then the last question I had, what are the typical requirements or barriers to entry that people need to keep in mind?

Typical requirements or barriers to entry, for me there are two things. One is finding good land deals. That is really your first objective, go find a good land deal. Don’t worry about everything else. If you find a good land deal, call me, reach out to me and I’ll help you with the rest. That’s the very first step.

The second barrier to entry is funding. When we started several years ago, funding was really hard. It’s gotten easier, but it’s still not the easiest. There are a handful of companies that will fund these or private lenders that will fund it. But as you know, if you have a good deal, most of the time the funding will follow. And then from there, it’s about operations, and operations is something you can follow a process to get done.

Perfect. And that sets us up well. Robert, if people are interested in learning more or connecting with you, what is the best way for them to do so?

The best is just to reach out to me on my cell phone. People think I’m crazy for handing out my personal cell phone, but I like talking to people and I like talking real estate. My cell phone is 864-293-2798. Just shoot me a text message and say, hey, I saw you on this podcast and would love to have a conversation with you.

I love it. Easy access. Well, thank you so much, Robert, for coming and sharing all of your wisdom and experience with us. And thank you to our listeners for listening. Please be sure to join me again next week for another amazing guest. I’ll see you then.

The post The Affordable Housing Niche Most Investors Overlook  appeared first on Adrienne Green.

I was skeptical of astrology my entire life. Until I started mapping the patterns against my own life and could not explain what I found. In this episode, I share what shifted my thinking, how I went from dismissing it entirely to using it as one lens for making better decisions as a real estate entrepreneur, and why I now think about it the way I think about weather when planning travel. This is not about horoscopes or sun signs. It is about pattern awareness, knowing the season you are in, and stopping the habit of fighting against your circumstances. If you are an entrepreneur making big decisions without perfect information, this one might give you a different way to think about timing and growth. 

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Here is the one-paragraph summary followed by the cleaned transcript:

I was skeptical of astrology my entire life. Until I started mapping the patterns against my own life and could not explain what I found. In this episode, I share what shifted my thinking, how I went from dismissing it entirely to using it as one lens for making better decisions as a real estate entrepreneur, and why I now think about it the way I think about weather when planning travel. This is not about horoscopes or sun signs. It is about pattern awareness, knowing the season you are in, and stopping the habit of fighting against your circumstances. If you are an entrepreneur making big decisions without perfect information, this one might give you a different way to think about timing and growth.

I was skeptical of astrology my entire life. It honestly sounded ridiculous to me. How can the location of the planets in the solar system when you were born affect how you are as a human being? But over the last few months, my perspective has shifted and not in the way you might think.

If you are an entrepreneur or real estate investor making big decisions, this might give you a different way to think about timing and growth.

As real estate entrepreneurs, we’re constantly making decisions without perfect information. When to invest, when to scale, whether or not to bring that person onto our team, when to take risks, and when to play it safe. So the question becomes, are there patterns or frameworks that can help us make better decisions?

So, let’s talk about astrology and how that could affect you as a real estate entrepreneur. As I said in the beginning, my thinking with astrology was always how could these planets possibly affect you as a human being? It didn’t make sense. At one point, I was having a conversation with a friend who was bringing up astrology and their lives and I had my normal “this is ridiculous” thought in my brain and then you know what I thought?

If I believe in a divine creator who designed this entire universe, couldn’t it be that that divine creator made it so that all of these things do interact and there is that interplay of impact and energy and it does make a difference? If this was divinely created, maybe there is some connection. Versus if people really felt like this was all a big bang and it was all random, then I feel like it’d be harder to believe in astrology, because there’s no overall plan or creation or system behind that.

So, I thought, you know what? I’m just going to be less skeptical. I’m just going to say, sure, whatever. Maybe it’s not my thing, but I’m not going to necessarily think it’s wrong like I did before. And I think how I felt before is pretty common for a lot of Christians. They believe astrology is conflicting with their beliefs. And I thought, you know what? Maybe it is aligned because we believe in a created ordered universe.

This didn’t mean I suddenly believed in astrology. It just meant I wasn’t as closed off and critical and judgmental of it. And then a few months ago, I went to a wellness retreat. And part of the wellness retreat included an astrology presentation. I listened with this new “maybe it’s not all hokum” mindset.

And what this presenter was speaking about specifically was the Saturn cycle. So Saturn, one of the planets, it takes about 27 to 30 years to make an entire orbit around the sun and return to where it was when somebody was born. And there was a presentation on the effect of Saturn at every 7 years or so as it goes every 90 degrees and you hit what are called squares at the 90 degrees, oppositions at the 180, another square at 270 degrees back to where it was when someone was born and then the Saturn return when it’s back where it was when somebody was born.

Now, these roughly 7-year periods when it gets to this every 90 degree interval are supposedly periods of growth, challenge, and maturity. So, I listened to this, I was like, “Sure, maybe.” And then what I did afterward, I pulled my own birth chart or natal chart, which is where you input into astro.com or some other website your exact date, time, and location of birth.

And based on that, it’s amazing. With technology now, they can give you in an instant the exact location, the chart of all of the planets and the sun and the moon at the time of your birth. And so then I took that, I put it into AI and I said, what were the periods of my key moments with Saturn? These 90 degree intervals, the squares, the opposition, the Saturn return. What were those periods in my life? Dates, years, months, days, years. When exactly did that fall in my life? I was going to test in my own life what this presenter had shared about Saturn and it was crazy.

What are the odds of the results that came up? So to be honest this first Saturn square when I was around seven or eight I don’t remember anything from that point or the opposition necessarily when I was around 14. So when we got to the Saturn square that was around when I was 21 it was crazy. I could not believe it because that period of time was when I got married. You want to talk about a big event in terms of maturity and growth and life-changing, marriage is a pretty big one. And there was no astrologer in my life or advising or being a part of choosing the date when I got married. And yet that really important life event fell during this Saturn square window.

And then when we talk about Saturn return, Saturn being back to its location when I was born, that was a period of time when I gave birth to my first child. So again, you want to talk about big life events. And again, no astrologer was consulted in timing the birth of my first child. And yet, it happened to fall during that window. And what was crazy to me is that I kind of felt like myself and my husband and the people in our lives were helping choose the date of things like our wedding. And the birth of a child was a little bit out of our control. Nature has a part. And yet they also aligned with these supposed periods of growth and maturity.

And that’s when I started to really think, hey, maybe there is a greater power in this astrology than I originally saw and maybe there’s some way that we can leverage that to work with it rather than fighting against it. Now, this is something totally different than what I normally cover and I recognize that. So, I’d love to know in the comments, have you ever looked into astrology? Or do you completely dismiss it? I’d be curious where you land on this. I’d love to hear in the comments.

Now, if you’re still like, “Oh my gosh, this is ridiculous. There’s coincidence.” Let me talk a little bit about what astrology definitely is not. And I am not an expert, and this is what I have learned so far. Astrology is not something that completely controls your life, and that you have no say in it. It’s not making decisions for you. And it’s also definitely not just your sun sign and these horoscopes that you see in the newspaper, popular magazines or anything like that.

First, let’s talk about this sun sign piece. That’s the most popular astrology that you see every day where all of humanity is grouped into just a few different groups based off of the day they were born. And I can see how this would totally create skepticism and it did for me as well. Now, that’s a very simplified version or a pop version of astrology. And I think that in order to really get the benefit of it, you’re having to look at stuff more deeply, like this whole Saturn return that ended up being so in line for me personally. That wasn’t just my sun sign of am I a Libra or a Pisces.

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Now, let’s get back. Using just a sun sign is trying to understand the weather when you only look at temperature. If we know it’s 70 degrees, 70 degrees with zero humidity and sun is going to be totally different than 70 degrees with 100% humidity and sun or 70 degrees and heavy rain. So the sun sign is really just one aspect and it doesn’t give you the full picture just like temperature isn’t going to give you the full picture when it comes to the weather.

So what is astrology? It’s really much more about your full birth chart or natal chart. This includes where the sun, the moon, and all the planets were at the time you were born. And so even if you’ve heard your whole life you’re a Sagittarius or you’re an Aries because that’s where the sun was, that doesn’t necessarily tell your whole picture. What’s going to affect you in the astrology belief is not just where your sun is, but where the moon was and the other planets were at the time of your birth. And then how they interact and go through and affect your life on a daily, monthly, weekly basis as well.

Now, if you want to see what this looks like for yourself, you can go to a site like astro.com. You input your birth date, time, and location. And you can get your birth chart and see not just your sun sign, but all of these other aspects as well. And then the way I think about astrology now is similar to how I think about the weather. Now, those of you who listen a lot, you know that I travel full-time internationally with my family. And one of the key things we consider is weather.

I’m not going to go to Da Nang, Vietnam in October when it rains on average 18 inches per month. I’m going to use what we know about the weather to plan for my best travels. The weather doesn’t control my decisions, but it does help me plan better and help me have the wind at my back and everything working in my favor. And that’s how I view astrology now. It’s awareness of patterns, not control over outcomes.

And I can be aware of these patterns and use them to my benefit rather than fighting against them. As an entrepreneur, I think about this as being aware of the season you’re in. I talked about the Saturn return and how this gives you periods or seasons of a lot of growth and maturity, which can be something that requires some challenge as well. There are different seasons based on how these things interplay. Some that are better for growth, some that are more challenging. And I’m not using this as my primary decision-making tool, but it is becoming one lens that I consider.

So, I’m still early in exploring this. I’m not an expert in astrology, and yet it’s something that I saw that I’d kind of closed off before, and yet I’m immediately seeing it being impactful as I learn more about it. So, thank you for joining me on a different topic today. And again, I’d love to hear your perspective. Drop it in the comments below and let’s see. Are you using astrology? Do you want to use it? I’d love to hear your story. And then join me again next week.

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