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.

If you’re a real estate entrepreneur trying to scale while doing everything yourself, there’s a better way. The Time and Freedom Starter Pack gives you the exact first steps to reclaim hours each week with real support, including what to hand off, where to start, and simple tools you can put into place right away. Download it for free at adriennegreen.com/starterpack.

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.

The post Astrology for Entrepreneurs: Can It Help You Make Better Business Decisions? appeared first on Adrienne Green.

I’ve been using Hospitable for years across multiple short-term rental properties, and in this episode I’m sharing my honest 2026 update on their AI features: what’s actually working in real operations, what’s created more problems than it solved, and how my approach has shifted since my first review a year and a half ago. If you’re a short-term rental investor trying to figure out where AI actually fits in your business, this one is for you. 

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’ve been using Hospitable for years now, not just testing it for a quick review video. And here’s what I think as a real estate investor with multiple short-term rentals on the platform. Now, if you’re new here, welcome. I love to share things that help real estate entrepreneurs break free of the grind and create bigger lives and bigger businesses and really live their dreams that they got to real estate for in the first place.

Now, let’s talk Hospitable. I did a full review of Hospitable about a year and a half ago. And if you haven’t seen that yet, I’ll link it in the description below, or if you’re on YouTube, we’ll link it here. Go check that out after this, because it’s going to go into more depth about the basic features of Hospitable. Now, since that first review, Hospitable has rolled out a lot more AI features. And so I want to talk about what actually works and what really doesn’t in real operations for short-term rentals.

Now, Hospitable, like so many other platforms, wants to get as much AI on their platform as possible. It looks great in demos and in marketing. But the reality is, does it work? Does it help? Automations and AI tools can help or hurt. And I think on Hospitable, there’s a little bit of both, which I’ll get into. Because while tools can look great on paper, when you’re dealing with real guests, real timing, and real conversations, that’s when you actually see what holds up versus what just makes a mess of things.

So let me share one of the AI features I consistently like every time I use it. And that is the improve message option in Hospitable when you’re messaging a guest. Why it works so well is because myself or my virtual assistant, somebody who knows the facts, is controlling the content first and then the AI is making it sound nicer, putting a little spin on it so it sounds really guest friendly and warm and welcoming.

So the specific way I use this improve with AI feature is myself or my property manager virtual assistant writes out the factual message first. Someone asks a question, do you accept pets or can I check in early or something like that? And we’ll write out the facts and then we click improve with AI. It improves the tone, the clarity, the professionalism. It just makes it really positive and friendly and warm. And I love it, it always works out well.

And I think this is a great example that AI is really good at refining something that’s already factually correct. But what I’ve seen is that AI is not great at creating the message from scratch, which gets me into the next AI tool within Hospitable that I do not love. And within guest messaging, there is also a suggest message option. So instead of getting in there and having a human being write the actual message or using a canned response or something like that, you can just click suggest message and the AI tool writes what it thinks the answer is. That answer has never been correct in my world. It has always been factually incorrect. It suggests things that are not how we do business, not our policies, not our procedures, nothing like that.

If somebody asks, can I get an early check-in? It’ll just be like, yeah, sure, whatever. Not quite. I might be exaggerating a little bit. You get the idea that that’s not how we handle early check-in. And so it’s never understood enough context about the situation, about the guest, about how we handle things to be correct.

And I have another example where the AI tools have broken down and not served me well. And that is the auto-reply tool. In my experience with Hospitable, this was one of the earlier AI tools that they rolled out. There’s a canned message option where you can save a template message for FAQs that you get a lot. Like I have one about early check-in. I have one about do you accept pets, all these things. When you get a question that is an FAQ, you can just select the canned message and it auto pops it in and you can send it.

What Hospitable did to level up their canned messages is they started this auto reply tool where you could have a templated response and say, hey, every time somebody asks about early check-in, just automatically send this response. And the AI tool in Hospitable was supposed to sense these keywords, recognize that somebody asked about early check-in, and then automatically send this response. So you get this really fast response time and have a happy guest because you replied right away. But it totally didn’t work well for me.

What would happen is that somebody might use a keyword or have a question and the AI tool would automatically send this auto response, but it wasn’t really what they were asking about. They just happened to use this phrase and the auto response was totally out of place. So I had this just happen. I had turned off all our auto responses, but I accidentally still had one on about early check-in. A guest asked for something that I couldn’t do, something about cleaning and linens, and I couldn’t say yes to them on that. And yet, I noticed that the night before they were scheduled to arrive hadn’t been booked yet. And so in order to have a good guest experience, I said, hey, odds are I’ll be able to get you early check-in. I’ll confirm the day of, but it looks like as of right now, we’ll probably be able to get you in at 2 p.m. instead of 4 p.m. So I wrote that in. Then they replied and they referenced that early check-in. So then this auto reply AI tool triggered and it sent the generic early check-in is case by case message that I have as my template response when people ask for early check-in.

It was completely inappropriate to the conversation because we’d already been having this conversation about early check-in. I already told the guy that odds were good that I could give it to him. And so this was really redundant and confusing. And just one of those grimace moments when you’re like, ooh, because you know, sending messages to a guest, it’s like pee in the pool. You can’t take it back, right? And so I immediately went in and made sure everything was turned off. Because that’s pretty much how it’s always gone for me. So I do not love this tool. I don’t think it’s a good example of AI and it doesn’t work for me.

Now, if you’re using this feature and it’s working well for you, I’d be really curious to hear how. Please put it in the comments below. If you are using this auto response AI tool in Hospitable, tell me how you have it set up and how it’s working, because it’s always been a hot mess for me.

Now let’s move on to a newer AI tool that Hospitable has rolled out, which is upsells. This is something brand new where they’re like, hey, you can put in these upsells and charge for them. They tout that you can do things like charge for early check-in, late checkout, things like that. And I saw this and I kind of rolled my eyes because I have been using an upsells tool for about a year and a half.

So before I ever set up this upsell option with Hospitable, I tried to find people who were using it to hear success stories and I couldn’t find anyone. Now, once I went to all the time and effort to set it up and it wasn’t leading to any sales, I did run across a few investors in my network who had also used it and said they had the same response, that they never sold anything with it. I was so excited about this because the HostCo already has vendors in their world. I didn’t have to deal with any of that. It was like, hey, if people want to rent baby equipment, if people want to schedule a massage, if people want grocery delivery, the HostCo already had vendors for that in the Myrtle Beach area as they do in multiple markets. So it was like the easiest possible way to do upsells and still nothing sold in a year and a half with three different properties.

And so I don’t really place much value on this upsells tool. Not necessarily because of the technology piece, it’s just that the upsells niche within short-term rentals hasn’t worked out for me and hasn’t worked out for anybody else that I have interacted with personally. So it’s not really a tech comment about Hospitable specifically. It’s just that the idea of upsells I think is better than the reality.

Personally, I’ve had it on my list for a few months now to have my property manager virtual assistant go in and shut down our upsells with the HostCo, get those messages out of our system, and just streamline our process more because it hasn’t led to anything. So there’s no reason to leave it in.

Now, another AI tool that Hospitable has had for a while now is the dynamic pricing tool. Now, many of us in the short-term rental space are using PriceLabs. It is the OG when it comes to dynamic pricing. You may also be using the built-in pricing with Airbnb. Now, PriceLabs is clunky. It is awkward. I don’t love it. And yet, it works. And I once more looked into Hospitable’s dynamic pricing and tested out their model to see what they would recommend for my properties. And it was not compelling. I have some weekday gaps over the next few weeks because my properties are in beach areas. People will come for a few nights over the weekend, so Monday, Tuesday, Wednesday nights are pretty much open, right?

And what the Hospitable dynamic pricing tool recommended for these weekday unbooked nights was actually to raise the prices. And it’s like, I’ve got these weekday nights over the next week or two, I don’t think increasing the prices is going to be what gets them booked. The fact that’s what they recommended just showed me that it’s really not there yet. As somebody who’s used dynamic pricing and used PriceLabs, I wasn’t convinced this was going to help me get more money or more bookings. So I don’t really see the dynamic pricing tool in Hospitable being there yet in terms of its quality.

Now, I know I’ve said a lot of things here that I don’t love about Hospitable. Again, if you go back and watch the first review, you’ll see I really like how Hospitable does the basics. I just think that a lot of their new AI tools, where they’re really trying to remove the need for a human being, isn’t working. So what is working? Well, their automation workflows are amazing for messaging guests. The check-in message, the checkout message, and all this standard guest communication works flawlessly in Hospitable. If guests don’t have one-off questions and just need the standard message of thank you for booking, get ready for your stay, here’s your welcome packet, here’s your reminder to take the trash out, and all your checkout messages, that works flawlessly 100% of the time. So I love their standard workflow for standard guest messaging.

Another thing I love in Hospitable that has worked flawlessly for me is the Smart Lock integration. I have Schlage and CodeLocks and I love the system that Hospitable has for setting up a unique code for every guest. We have very simple settings of when it starts to work, when it stops to work, and when we do things like early check-in or late checkout, it’s really easy to go into the system and modify the times for that code to work. So I love the Smart Lock integration.

Hospitable also works great for our team members. It’s really easy to connect with our cleaners’ system and their calendar. And for a few houses, we use a linen service. It does a great job of sending the linen service messages so that they can get things onto their calendar. We can also share a calendar link so they can see things on a calendar. So I love the integrations they have for collaborating with other team members. Hospitable is also really easy for my property manager virtual assistant to use as well. That’s all worked beautifully within Hospitable.

Now, if this is your first time here, you may not know that I actually have a virtual staffing company where we help entrepreneurs, including real estate investors, get amazing virtual assistants who can really do things like be your property manager. If you are interested in learning how a virtual assistant could support your real estate investing, grab my Time and Freedom Starter Pack at adriennegreen.com. The link is below. It’s going to give you the tools to determine whether or not a VA would help your business and help you create a bigger life and bigger business for yourself.

Now, what do I do differently now than I did a year and a half ago when I made that first review? I have seen that with Hospitable, while we have these AI tools, at the end of the day, you need a human being behind the scenes who has the wisdom and the judgment that AI doesn’t always have yet, really controlling things. And then the AI just makes things faster, easier, and puts a prettier bow on it by making those messages read a little bit nicer when you use that improve with AI option.

What that means for me is I’ve really leaned into having that property manager virtual assistant, that real human being, and supporting them with AI so that they can do their job faster and easier. So in addition to things like the improve with AI, we have things that we’re using within ChatGPT that houses our information and helps the virtual assistant get the right answer and solve problems faster and easier. And she has that personal touch and that wisdom that connects the dots and doesn’t make it awkward.

So what is my final verdict on Hospitable in 2026 for short-term rental owners? I still recommend Hospitable with the right expectations. You do need a human being behind the scenes controlling things. You cannot have AI do everything here because the AI in Hospitable is going to embarrass you with some guest communication. It is great for supporting a team, and yet it’s not a fully automated system where you can remove humans from the process.

If you haven’t seen my original Hospitable review, I break down all the core features that I love there. Go watch or listen to that next. And I’d love to hear from other hosts in the comments, what’s been working for you and what hasn’t. Whether you’re using Hospitable or a different property management system, I’d love for you to share and add your voice to this conversation. And then join me again next week.

The post Hospitable’s AI Tools: What Works and What Doesn’t in 2026 appeared first on Adrienne Green.

If you’re building a real estate business and still feel like everything depends on you, this conversation will likely hit home. In this episode, I sit down with Julie Cooper to talk through what it actually looks like to grow a portfolio while navigating financing, rural deals, systems, and team building. We get into the decisions behind private money, the realities of managing different property types, and the lessons that come from scaling without enough support. If you’ve ever felt stretched thin or unsure what needs to change next, this will give you a clearer lens on where to focus. 

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, hello, welcome to another episode. I am Adrienne Green and today I have with me my friend and investor Julie Cooper. Thanks for joining me, Julie.

Thanks for having me. This is awesome. It’s good to see you.

Thank you. And here on the podcast, we help real estate entrepreneurs break free of the grind and live the lives that they got into real estate for in the first place. I know you’ve got a great story about that, Julie, and about the freedom that it’s giving you that we’ll get to at the end. To start off, can you just give us a quick snapshot of what your real estate investing looks like right now?

Yeah, I’m super excited. I retired from education two weeks ago. This is full time real estate investing now. I invest with my siblings, my sister and my brother. We are all in together. Between all of us, we have nine doors right now, and we are working on some other ones as well. They’re a mix of short-term rental, long-term rental, mid-term rental.

We do have a duplex in the mix, so there’s multifamily in there, and we’ve done a ton of renovation with them. Even though they haven’t been fixed and flips per se, which we have done one of those, they’ve been fixed and hold, so we’ve done a lot of renovation through those.

Perfect, that was a great summary. I love how you shared how you’re creating freedom through your real estate investing already. I’m excited for you in that transition.

Yeah, thank you. I know you’re an inspiration. One of these days I’ll be traveling as well.

Well, and you do travel a lot.

Did you see my thing about last week in March? I was everywhere in March. It was crazy. It was fun. I loved it. But I needed to be home for a couple weeks.

Right, yes, and that is a fun thing that you get to say and be like, I need to balance time home versus traveling when you’re a real estate investor that you can’t always say as a W-2 employee.

Right, so much more freedom.

Yes. And I also love that you do this with your siblings. We get a lot of people in the real estate entrepreneur space like husband-wife teams, and yet we also have this sibling dynamic that you’ve got going on, which is less common and amazing.

Yeah, it has been such a great experience. We live in two different states. Two of us live in Alabama and two of us live in Las Vegas. One of my sisters is a principal, so she’s busy and doesn’t have as much involvement with it, but it’s drawn us so much closer together as adults.

I love that. I have sometimes shared how one of the greatest things I love about our travel lifestyle is getting to spend so much time together as a family. I really want my three kids to be close. I want them to be the kind of siblings who would go invest together or grow businesses together in the future.

Yeah, we attribute that to our mom. She raised us so that we all respect each other. Our age differences are quite a bit, and that has actually benefited the connection that we’ve had through real estate.

I love it. Let’s talk about your value add investing. How do you decide which financing strategy to use?

That depends on the deal. Our investments are in Alabama and Costa Rica. Depending on where it is and how much the investment is, that determines the financing. We’ve purchased properties outright, done seller financing, and used private money.

Seller financing is by far the easiest if it works out. That depends on the situation with the seller. I always ask that question because it can benefit both sides. If that doesn’t work, then we look at other lending.

Over the last few years, I’ve made connections with private money lenders. Last year I raised over $850,000 for our projects. That allows us to attach funding to the projects and be more effective with our own money.

I would love to dive into the private lending piece. It’s more expensive than conventional loans. Why is it still a win?

It can be shocking at first when you see the interest rate. But because of the timeline, it makes sense. If you’re borrowing for six months, eight months, or even twelve months, paying a higher rate can still work.

It always goes back to the numbers. You need enough margin in the deal. But the ease of access to the money makes a big difference.

With traditional loans, the paperwork is extensive. With private money, it’s more direct. It’s tied to the project, and the process is much simpler.

Right, and it allows you to do more deals.

Exactly. And when you actually run the numbers, sometimes the difference in interest is minimal compared to the opportunity.

And with draw structures, you’re only paying interest on what you use.

Yes. If you’re borrowing $100,000 but only using $20,000 at a time, you’re only paying interest on what you’re using. That makes a big difference.

Right. And fees matter too.

Yes, fees can add up quickly.

When you’re looking at deals now, what are your non-negotiables?

We’ve learned not to take on too much. Historic properties are a whole different level. We probably won’t take on another one soon because of the complexity.

Another non-negotiable is sticking to the numbers. There have been times where we stretched because we wanted a property, and it always comes back at the end.

Let’s talk about rural properties. What’s your experience?

We like rural properties, but lending is difficult, especially for short-term rentals. You have to find lenders who allow both.

We also learned to ask about utilities upfront, like well, septic, or city sewer, because that affects expenses.

Have you found benefits?

Yes, creativity and space. With one property, we already have multiple phases planned. There’s also more flexibility without HOA restrictions.

Let’s talk about systems. You’ve grown your portfolio. What’s helping you manage it?

We need better systems. We use Google Drive and shared communication. It works, but there’s room for improvement.

Our goal is to get a VA because there’s a lot to manage.

That’s part of the process. You build and refine over time.

We’ve also learned to focus on finding the right people instead of doing everything ourselves.

Yes, the “who not how” approach.

Exactly. We’ve gone through different team members to find the right fit.

That’s normal. Hiring takes time.

Yes, we’re willing to go through multiple people to find the right one.

Let’s talk about Costa Rica. What led to that?

It was a unique opportunity. I was there on vacation, found out the property we were staying in was for sale, and explored it.

Seller financing made it possible. Financing internationally is difficult, so that helped.

We ran the numbers and moved forward. We closed in 30 days, which is unusual.

There were challenges, but it was worth it.

Would you do it again?

Yes. It comes down to asking the right questions.

What about maintenance in that environment?

We rely on our property manager. Regular maintenance, pest control, and upkeep are essential.

We also monitor moisture and structural wear.

Julie, this has been great. Where can people connect with you?

You can find me on my website, movewithmomentum.com, or on Instagram and LinkedIn.

Perfect. Thank you for sharing your experience.

Thank you.

The post Your Biggest Asset Is Actually Your Liability appeared first on Adrienne Green.

If you’re building a real estate business that’s growing but still feels dependent on you, this conversation will likely hit close to home. I sat down with Brittany Brooks to talk through what actually happens behind the scenes as you scale, the breakdown points most people don’t see coming, and the shifts required to move from doing everything yourself to building a business that can truly support 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!

Welcome back to another episode. I’m Adrienne Green and today I have with me my longtime friend Brittany Brooks. Brittany, thank you for being here with me.

Happy to be here!

And on the podcast, we help real estate entrepreneurs escape the grind to actually create the life of freedom that they usually got into real estate for in the first place. So Brittany, I’d love for you to share with our listeners, what does your real estate business look like right now?

Well, after a long journey of breakdowns and breakthroughs, we are living a life by design, a business by design, very intentional monthly annual reflection. I own a real estate brokerage. My husband and I used to have a top real estate team in the city of Jacksonville. So we’re in Jacksonville and it’s called Momentum Realty. We house and manage about 280 real estate agents now and helping them live incredible lives and build big businesses. What we say all the time is you get into real estate to get out. We are helping them build their businesses to scale and potentially find freedom and get out of real estate. I know it’s crazy to say, get into real estate to get out of real estate.

Right, well, real estate gives you so many opportunities that if you’ve been in real estate, you don’t question that phrase. It makes sense.

Yeah. You love it, but you’re like, how do I get out of this? And why did I choose this? But I love this. It’s like this toxic relationship that you see the light, but you’ve got to get there.

Right, exactly. And there’s going to be ups and downs along the way. That is what we will share in today’s call. What I love about having Brittany on for our listeners is a lot of our speakers are in the investing space. But this podcast is for all real estate entrepreneurs. Brittany, while she is a real estate investor, her primary seat was as an agent and is now as a broker. I’m loving her coming on and sharing that part of the story. But Brittany, how did you get into real estate in the first place?

So this is a fun one. I forgot to say, real estate investing. This story will involve mainly real estate investing at its start that led into creating a business and multiple businesses and streams of income within real estate. The quick version is we went through the home buying process ourselves.

John and I were both working in mergers and acquisitions, real estate M&A, and I was doing small cap company mergers and acquisition activity as an analyst. We were living the grind for corporations and doing exactly what we were supposed to be doing from college to graduating and getting prestigious jobs.

We were telling ourselves that we should want that and that this is what you’re supposed to be in. We went through the home buying process for the first time. At the time we were like, this is not okay. John eventually ran the show, went to the seller himself and delivered our offer. Our agents were not as active as we thought they should be.

We come from a place of demanding excellence and standards and professionals doing professional jobs and they weren’t. With our background in accounting and finance and John in real estate activities through his corporate job, we were like, there could be something here. I think the first thing for every entrepreneur is they say, I think there could be something here. Then you wonder if things could be different. Then you wonder if it can be you and you have an identity crisis.

So I’m pretty conservative in terms of risk, playing the safe game. The thought of going into real estate and quitting my job, I was a CPA at the time, I had done everything I was supposed to do, was very daunting. So John is like, I think I want to quit my job and become a real estate agent. At the time, the premise of having the title of real estate agent has a certain connotation to it.

You’re going to become a real estate agent? What are you doing?

Yeah, I feel like it’s maybe a step above ambulance chasing attorneys. It has a certain vibe.

Yeah, you’re like, okay, we kind of get the feel of who you are. He decided to get his license. I said, you’ve got three months. We were not engaged at the time. We were just living together. We had moved from Washington, D.C. to Jacksonville. Even just that, following a boy to Jacksonville, for me, I was like, what are we doing? Already we’re entering crisis mode.

Now my boyfriend wants to quit his job and become a real estate agent. I said, you’ve got three months to make money and I’m not going to be anybody’s sugar mama. He made it work. Pounding the pavement every day. We’re in Florida summer heat, knocking on doors, dropping off flyers, trying to get his name out there, buying leads. He said, I’ve got nothing to do all day. I’m trained to work 10 to 12 hours a day or more. I’ve got nothing to do but sit here and dial.

He started the business at the end of 2015. We did get engaged. He bought my engagement ring with the first house sale commission that he made. It ended up working out well. He sold about 65 homes his first year.

This is working.

Then he was knocking on me to come over and join the business. I said absolutely not. This is your thing. I’m still in tunnel vision of doing what I’m supposed to do and living in the corporate path. Then he showed me the numbers. He said, I make three times what you make and I work half the time.

You can’t deny the data. We are financiers at our core. Data tells the story. When he showed me the numbers and the profit, I also saw the joy he was having with clients every day. It was a different experience. He said, I’m either going to hire someone or I’m going to hire you as a buyer’s agent. The business had gotten too big for him to handle on his own. This was our first moment of leverage.

Eventually I did it. It was painful because I loved my job and my team. But there was a bigger picture being played out. That was 2017 and I joined him. I sold 66 homes as a buyer agent.

So I came on as a buyer agent only. I did not touch listings. We decided very early on to have separation of duties. You do not cross into the other person’s swim lane unless you ask for permission. We were not allowed to give each other feedback unless we asked for it. We had to get individual coaches because you’ve got two high drivers that want to help each other grow, but it can collapse into resentment.

Working with your spouse can be amazing and it comes with its own set of challenges.

Exactly. We thought we would kill each other at the beginning. But you can do it the right way with the right systems and coaching. We became the number one Keller Williams team in Jacksonville in 2018 and it took off. It was amazing.

We were just married, no kids, and we dove head first into everything. Then we had our baby in 2019. That was when the first big breakdown happened.

We became a two person, $40 million sales team selling hundreds of homes a year between the two of us.

Two high drivers just demanded levels of excellence from our programming and training for so long that we couldn’t see outside of that. No one could do it better than us. You go into it with that mindset, and then you crash down and burn.

All of a sudden, I have our first child in 2019. I can’t go out on showings. I’m sleep deprived. John is trying to handle two massive businesses as a solo agent and trying to cover me.

At the time, we had an operations manager. We had hired an operations manager and then two showing assistants. This was the first start of being so desperate that you have to find leverage.

Because sometimes you have to get to a place to realize that you need something. But it would be a lot better if you prepared for it ahead of time and didn’t have the storms that came.

And that’s something I always want listeners to hear. How many stories have we had where someone says they were at a low point and had to build systems or delegate or leverage other people? We’re giving you the shortcut. Do it before you get to that point of chaos.

So you had the operations manager, you had the showing assistants. What happened from there?

From there, we were going to burn it all down.

If you haven’t gotten to that point, you start thinking, am I just going to sell this, burn it, and walk away? That’s a natural thing that happens.

You get to a place where you can’t face it anymore. You can’t have any more stimuli coming at you. Especially in client services, you just want to turn it off.

We got there through years of figuring it out along the way. But the goal is that people can learn from these breakdowns and not repeat them.

Ego is a very interesting thing. When you believe you can do it all yourself, you don’t see outside of yourself. Ego can drive a business to a point, and then it all comes crashing down.

John broke his back. We had a newborn. We had no family nearby. They came to help for a few weeks, then went back to their lives. We still had this massive business and people needing us constantly.

Eventually, we started resenting the business.

We were going to sell it. We were going to sell it to our showing agents and just collect referral fees.

At the same time, we had started house hacking. We moved every six months, upgrading homes, using commissions to acquire properties. We built up four to five homes and started doing BRRRR deals.

So at the point of breakdown, we had rental properties producing some passive income.

That was also the first year we made a million dollars in commission.

We thought we could live off rentals, shut down the business, and live minimally.

We started selling everything in our house. We thought, how minimal can we live?

But that’s not a life of purpose. That’s a life of scarcity.

We decided to move to North Carolina. We made eight offers on homes and couldn’t get one.

That was a turning point.

It was like something was telling us to pause.

We realized we were running from the problem instead of solving it.

We used a whiteboard and mapped everything out. What do we love? What’s broken?

We realized we loved mentoring. We loved people. We just couldn’t handle the volume.

We were also paying massive splits to our brokerage, and our team members were struggling financially because of it.

We looked at everything and realized we were already building the foundation for a brokerage.

So in 2020, we launched Momentum Realty.

We created a lean, virtual model. No unnecessary overhead. Focused on top producers.

Over time, we expanded to include newer agents as well, because experienced agents needed leverage.

From 2020 to now, we’ve grown to 280 agents.

That growth came with breakdowns and rebuilding systems.

When we started delegating, it was out of necessity.

What I started doing was tracking my time.

Instead of jumping straight into time blocking, I tracked everything for a month.

Then I asked, am I the only person who can do this?

If not, who should do it? An owner? A hire? A virtual assistant?

Then I grouped tasks and built job descriptions.

That’s how we started hiring VAs.

The first round of leverage actually started at home.

Cleaners, meal prep, basic things that free up energy.

Then we moved into business leverage.

You start thinking about your dollar per hour.

Even if you enjoy something, you start asking if it’s the best use of your time.

We also did this with each other. What are our strengths? What should each of us be doing?

It’s about questioning everything.

Delegating sales is the hardest.

Lead generation is the highest value activity.

We outsourced recruiting for the first time.

It didn’t work the way we expected.

The message got diluted.

Our close rate was much higher than the recruiter’s.

We tracked everything. Calls, appointments, conversion.

There was a gap.

Then we looked at ROI.

Our model is lean. We charge less. So the numbers didn’t support hiring a recruiter.

That was a hard realization.

We’re still navigating what roles can be delegated.

We have a lean team, about five to six people supporting 280 agents.

The question becomes, how lean can you go?

And what is the next role to hire?

There’s a belief that someone can do something 80 percent as well as you.

I don’t agree with that.

You can find people who do it better than you.

That’s the goal.

We learned that leverage can work incredibly well when it’s aligned.

Don’t be afraid to hire leverage.

There is a version where the people you bring in are better than you.

That’s when things really shift.

They elevate the business beyond what you could do alone.

That’s when you step aside and see what’s actually possible.

Thank you for sharing that.

And for our listeners, I would love for you to think about what real estate entrepreneur you know who could benefit from hearing this and send it to them.

The post The Operational Shift That Takes You From Solo to 280 Agents appeared first on Adrienne Green.

Most real estate entrepreneurs don’t struggle because of a lack of opportunity. They struggle because they’re trying to scale without the right support, systems, or structure. In this conversation, I sit down with Leo Young to unpack what it really looks like to move from hustle into a business that can actually grow. We talk about leadership, burnout, building teams, and why manufactured housing is one of the most overlooked yet durable asset classes. If you’ve been feeling stretched thin or unsure how to scale beyond yourself, this will give you a clearer path forward. 

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 here we help real estate entrepreneurs escape the grind with private lending and virtual assistance. And today I have with me Leo Young with Cornell Communities. Thanks for joining me, Leo.

Thanks for having me, Adrienne. Very excited to be here.

I know we have so much to talk about that is really going to benefit people. Before the call, we were talking about lessons learned from Tesla, community building, and manufactured housing communities, which is something we haven’t talked about yet, so I’m excited for all of that. As we get started, Leo, for people who don’t know you yet, can you give us a quick snapshot of your real estate business?

Sure, I’m the founder and managing partner of Cornell Communities. We are an owner and operator of manufactured housing communities across the US. We have two goals. One is to improve and offer affordable housing to the community and improve the way that folks live. The second is to give great returns to our investors who make this whole thing possible.

I love that and I love that you come out with what your mission is. We can see that you’re very mission driven and it’s about helping other people. It’s about how can we add value to their lives. And we were talking beforehand about how that relates to the name Cornell Communities itself.

Yeah. The origin of it is twofold. For me, I love meaning and that’s how I structure everything. The name Cornell, my co-founder and I had that in common. He went to undergrad there, I got my commercial real estate certification there, and we thought that was a great connection. Cornell embodies a smart approach. We’re not flashy, we follow a process that works and stick to what we know.

The communities aspect is that yes, our asset class is manufactured housing communities or RV communities, but we want to highlight that we’re really building communities. A lot of people like to make money, that’s the base level. But it’s more important to see the bigger picture. Why are you doing what you do? For us, we’re building communities. We talk to the residents, see what their lives are like, and figure out how to improve it. We budget for improvements to meaningfully change their lives.

I love that and I’ve seen across the board with investors who are succeeding in residential space that when they focus on the residents, that translates to greater returns for the investors as well.

Definitely. It comes down to philosophy. Some people see money as the end goal, but for me it’s a means to an end. It’s a progress marker. Money is a universal store of value. It means I brought enough value to the world. I think that’s something I learned from my time at Tesla. I’m very mission driven. If I’m going to build a team, we better be working on something good.

Right, and we better be helping other people. That’s one of my big things. Whatever we’re doing, we’re doing it to make someone else’s life better.

Exactly.

We often talk about both the mission and the logistics. How do we run a solid real estate business? How do we get from being a solopreneur trading hours for dollars to becoming a business owner? Let’s talk about what you learned from Tesla that you implement within Cornell Communities.

One of my biggest takeaways from Tesla is the role of leadership. As a leader, you embody such an important role to your team. People look to you for guidance. There’s a reason people join your team instead of doing their own thing. As entrepreneurs building organizations, we need to embody that.

Tesla’s mission was to accelerate the world’s transition to sustainable energy. That was ingrained in us. We were all bought in and operating at a high level every day because it felt like what we did mattered. Now the question is how do you create that environment and culture for your people?

That’s something a lot of real estate entrepreneurs need to hear because most haven’t been trained in leadership. They go from being hands-on operators to leading others, and it’s different.

Exactly. Real estate entrepreneurs find a way to make money, but to advance, you have to build a business. That’s a separate skill. You have to put in the right systems, the right people, and measure them the right way.

As you were building Cornell Communities, do you have a story where you learned this the hard way?

One pivotal moment was when my co-founder left. Before that, it was built on hustle. After he left, it was a crash course in building systems and bringing on people. I had to figure out who to hire and what systems to put in place. Putting my ego aside and asking for help was huge. And learning to do things imperfectly. You’re never going to figure out the perfect system. It’s always iteration.

Right, you have to put the ego aside and ask for help. At a certain point, you can’t brute force it. You have to build systems and a team. For me, that happened when I had three kids. There weren’t enough hours in the day, so I had to build systems and bring on support like virtual assistants. Those low points often lead to innovation.

Necessity is the mother of innovation. The reward is the journey, the skills you build, and the team you build. Right now, we’re in a great time to build businesses with virtual assistants and AI. We can offload tasks and build more efficiently.

I love that. Technology allows us to do more with less time. Now let’s shift into manufactured housing. What drew you to this asset class?

It’s not something people grow up wanting to do. I got introduced through my co-founder. The appeal is that demand for affordable housing is always there, especially in volatile economies. Residents stay long-term, often 10 plus years. It’s a durable asset class. And it provides affordable housing without relying on government subsidies, which matters to me.

It sounds like you had some specialized knowledge through your co-founder and that it aligned with your mission and values. For listeners who aren’t familiar, can you give a quick summary of what manufactured housing looks like and what you’re investing in?

Manufactured housing communities are properties zoned specifically for that use. There can be anywhere from 30 to 300 units. Manufactured homes are built in factories and placed on-site. Despite the name “mobile home,” they are not easy to move once installed.

We own the land underneath, provide utilities, maintain common areas, and make improvements like road repairs and utility connections. These communities are often 50 to 70 years old. Because of zoning restrictions and NIMBY attitudes, very few new ones are being approved, so municipalities allow existing ones to continue. Our role is to acquire older communities and revitalize them by improving infrastructure and connecting them to municipal utilities.

So you’re owning the land, and the residents typically own the homes themselves?

Yes, in most cases the residents own their homes. That allows them to build equity, and when they sell, they benefit from that. Our improvements also increase the value of their homes. For us, we’re not responsible for maintaining the homes themselves, which improves profitability. In commercial real estate, value is driven by income, so increasing profit directly increases value.

And they’re paying lot rent to you for the land?

Exactly.

One of the benefits is how long people stay. Since the homes aren’t easy to move, residents tend to stay long-term.

Exactly. From an affordability standpoint, someone might pay $400 in lot rent versus $1,500 for a single-family rental. That cost savings keeps people in place. Some residents eventually rent out their homes, but regardless, we continue collecting lot rent.

Do you focus on certain geographic areas or are you location agnostic?

We focus primarily on the Southeast and Midwest. The Southeast has strong population growth and business-friendly environments. The Midwest offers strong cash flow and stability. We also have some assets in the Northeast, but regulation can be more challenging there. Rent control and other policies can make it harder to justify improvements, which limits investment.

That aligns with what we see across other asset classes as well. It’s still about underlying fundamentals.

Exactly. Commercial real estate value is based on net operating income divided by the cap rate. So increasing income increases value.

You’ve given us a great overview of the asset class. When a new deal comes across your desk, what are you looking for?

The property needs to be large enough to support infrastructure and our team. We typically look at 30 to 200 units. We prefer properties with public utilities because private utilities can require significant capital improvements.

We also look at current financial performance versus potential. Many properties are owned by individuals who haven’t raised rents in years. That creates an opportunity to normalize rents while still remaining affordable.

Another key factor is infill potential. Some municipalities make it difficult to add new units, so understanding those constraints is critical.

And there are also financial pressures from municipalities themselves.

Yes. It can cost a municipality $7,000 to $8,000 per year to service a family in a mobile home community, while they may only collect around $1,000 in tax revenue. That’s part of why they resist expansion.

That’s interesting because many communities still need affordable housing for workers.

Exactly. In some markets, these communities are being redeveloped into higher-value uses like luxury apartments or retail. That displaces residents who then struggle to find affordable alternatives.

That highlights the broader impact of real estate investing. Investors are directly influencing communities and housing availability.

Yes. Many investors care about where their money goes. Investing in housing provides a tangible impact while still generating returns.

Are you syndicating these deals?

Yes. We work with limited partners who invest passively while we handle everything from acquisitions to operations and distributions.

What does the typical investment timeline look like?

We typically hold for five to seven years. Our goal is to double the investment within five years. We often do a cash-out refinance in years two or three, allowing investors to recapture their initial capital tax-free while continuing to receive income.

So investors can continue earning returns even after their original capital is returned.

Exactly. The goal is to create long-term income streams while reducing risk.

That’s incredibly helpful for people exploring passive investing or syndications. Thank you for breaking that down. If someone wants to learn more or connect with you, what’s the best way to reach out?

They can visit cornellcommunities.com to learn more, or reach out on LinkedIn or Instagram. I’m always happy to be a resource.

Thank you for sharing your experience and insights. And thank you for being here.

Thank you, Adrienne. I hope this was helpful for everyone listening.

The post Manufactured Housing: The Operationally Demanding Asset Class Worth Your Attention appeared first on Adrienne Green.