I am Adrienne Green, and here’s a look inside my conversation with Mark Gordon, a luxury broker who has spent more than 25 years working the ultra-competitive Vail, Colorado market. This one is worth watching if you have ever wondered what real estate looks like in a market with almost no room to negotiate, no fix and flips, and sellers who genuinely do not need to sell. Mark walks through the scarcity economics that shape every deal in Vail, why he built his entire business around education instead of sales tactics, and the deliberate way he is thinking through bringing on his first hire after decades of doing it all himself. If you are scaling a business that still runs almost entirely through you, this conversation will give you a lot to think about.

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 listeners, welcome back to another episode. I’m Adrienne Green, and today we’re here with Mark Gordon. Now, here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start. And Mark has a really cool perspective on that as a very experienced realtor in the Vail, Colorado market. So, for listeners who aren’t familiar with the Vail market, can you give us a quick picture of what your business looks like there?

Yeah, so if you’re not familiar with Vail, obviously we are a ski town in the Rockies. What’s very interesting about us is we have no history besides being a vacation tourist spot. The town itself is as old as I am. 1962, 63 was the first ski year.

And before that it was just ranch land, and I think they grew potatoes and lettuce, pretty much nothing here. And we created this amazing vacation spot. So what’s nice is for second homeowners, which makes up most of my business, the town itself is very welcoming. Tourism, the luxury wilderness experience, is very much in the town’s DNA. So an incredibly welcoming, relatively business friendly ski town mountain town.

That is so unique, that it’s so young and that it really didn’t exist before it became there as like a ski and vacation location. Like that is cool.

Right. Yes, some mornings those 63 years don’t feel so young to me. But as far as a town goes, Vail is very young, which is really cool. So when I was on the town council in ’05 when I got elected, the mayor of the town council that I was on was one of the founders of town. And so I got to serve.

wow.

with someone who invented the town. And I would get to go ski with Earl Eaton, who was a uranium prospector and found the back bowls. So I’m like in that middle area where I straddled Old Vail and moving into New Vail, which is cool. And my business is primarily, most of my revenue comes from second home sales, vacation home sales, third, fourth and fifth homes as well. But I have a very political soft spot to work with primary residents, first-time home buyers. I got my start in town politics as a housing activist. So I work very hard to make sure that we don’t become a cruise ship in the mountains, that we remain an authentic town where a guest can come into town and

Right.

Yeah.

have a bartender who lives on the same street as them and can tell them where to go find this secret powder stash.

Right.

And that’s so important. That’s such a challenge that so many of these vacation destinations are facing right now, worldwide, as tourism has picked up so much post COVID and everybody really appreciates the luxury of being able to travel and visit and go on vacation. So we’re all doing it a lot.

Yes.

Yes. And we had a little bit more of the issues than we have ever had in the past post-COVID because everything was so busy. But we’ve settled back into our normal understanding that we couldn’t live here if our guests didn’t come here. And I certainly wouldn’t be able to go see the New York Philharmonic at an amphitheater a fifteen-minute walk from my house for twenty eight dollars and sit on the lawn if it wasn’t for our guests. So we appreciate them, and they are part of the community.

Right. And I think already, as we’ve spoken, Mark, people can understand or get that you’re much more of an educator who’s obviously passionate about where you live, rather than simply a salesperson or transactional. How did you arrive at that positioning of focusing on the education, and what’s changed in your business once you leaned into that approach?

I will be vulnerable and reveal some things about myself. Hopefully the viewers and the listeners find that interesting. I come from a long line of salespeople, but I also have always had a little bit of a negative feeling towards salespeople. I watched Glengarry Glen Ross, Death of a Salesman, all that stuff. So I’ve got that in there.

When I went to graduate school, I was teaching at Indiana University film classes. And so I’ve always been somewhat of a teacher. And so it wasn’t so much a change in my business as that was by design, the way I’m going to work. I’m going to work as an ambassador for Vail, and I’m going to let Vail sell.

And I’m just going to answer questions and point things out. It’s interesting in real estate, and your viewers will understand this. There are clients for every type of realtor. There are some people that really want someone who’s more of a selly realtor, because without that push, they would never do anything. They need that.

Yeah.

Mm-hmm.

Right.

for themselves to make themselves happy. My clients tend to run from a sales approach. If I started pulling trial closes, I want to put a sign behind my desk that says, never a trial close. Which do you like, A or B? So it’s just the way it works. And what makes it interesting is because

Right.

I tend to attract clients who become friends. And I think that’s a little bit easier in a vacation spot because I don’t have to be full-time friends with them. But when they come in for the week or they come in for two weeks, we go up on the mountain, we make turns, the families get together and go eat amazing restaurants, or we go on a hike, and we do all of those types of Vail things that people just love.

Mm-hmm.

Ha ha ha.

Right. I think you’ve really hit on something. You’ve chosen a strategy that is authentic and resonates with you, and therefore you attract people that you do genuinely like, and it’s probably part of the reason you’ve been able to do this for quite a while and haven’t gotten burned out, because you’re not forcing yourself to do a strategy that is fake for you.

Right. No scripts, no trial closes. Although, obviously I’m in a sales position, and there’s nothing wrong with a sales position. My business depends on me closing. So yes, there is definitely a sales part of it, but I lean into the town to do the sales.

And an interesting thing about the business here, about real estate in Vail, is we are not the type of location that the DuPont Registry will bring in someone who’s never been to Vail and buy a house. We’re not Las Vegas, we’re not Miami, we’re not any of those types of places. Pretty much a hundred percent of the people that purchase with me are people who already love the town.

Who’ve been coming to the town, whether their parents brought them here, or they just came for a week and fell in love with the town. But people have a history with Vail before they make that decision to start looking at homes. So we all have that in common. And that’s what’s really cool. So the people that live here have the same love as our guests for the Vail lifestyle. So it allows the hedge fund guy from Connecticut to become an actual friend with the bartender and go out the next morning and go ski together or go on a bike ride together. It’s a really unique place.

Mm-hmm.

That is very cool. I love how you describe that. Something that I know is true there is that there’s a scarcity, right? Scarcity economics, there’s not a whole lot of supply. And that’s in direct contrast to what we’re seeing on the national level right now with housing, where supply is creeping up and up and up. So I’d love for you to give some insight for people in terms of what your business is like that’s different with this scarcity play of just there not being that many houses in Vail.

Yeah, it’s interesting. So the town itself is surrounded by national forest. So unlike some other ski towns that have private land, we cannot have sprawl. And in fact, our ski areas are on national forest; they just have a long-term lease. So we can’t go any further than the seven miles as wide as we are, and the very narrow town, because once you start going up the hills on the valley, it turns into national forest, which is beautiful, because from my house, I see amazing forest right there. Whichever way we look, we see the forest. And we don’t have to worry about sprawl. So our development is redevelopment. And we do have a pretty much constant back and forth between how do we redevelop and what is the right density. And there’s very valid arguments on each side of that, because we’re a small town and we’re quaint. So no, we don’t want skyscrapers. But the environmentally conscious way of developing is to increase that density, because if the building happens in Vail,

Mm-hmm.

Right.

Right.

Right.

we have our free bus system. No one has to drive. We have a pedestrian village that’s modeled after Zermatt. We can keep everybody in the one place without spending too many resources. And the town is now investing a lot of millions of dollars in building employee housing right here in town, which is pretty cool to see.

Mm-hmm.

I think I got off track from scarcity, scarcity, yes.

Yes.

And I see the educator piece coming in, and I love that we’re having that true discussion about the challenge of density and providing housing for everybody who’s working there, but then also, high density housing is its own beast. So back to the original question, yes, when you’re working with your clients who are looking for those vacation homes, what does the supply look like, and how do you work within that?

Yeah, so because there’s no more Vail to build and spread out to, there’s redevelopment, and there’s a lot of purchase at the very high end. People purchase homes that to some people might seem perfectly fine, and then they’re buying that home for the land and redeveloping it. And sometimes there are

Mm-hmm.

fifteen million dollar scrapes just for the land. So what I do with the scarcity is I make sure to pre-educate before they show up and we go out looking at homes for what they can expect. First of all, that scarcity keeps the negotiation margins very tight.

Wow.

Mm-hmm.

Right.

The statistics show over many, many years that it almost never happens that a home closes for over a 10% discount off of the asking price. Only in the Great Recession were there some times where it might go to 15 or 20%. But other than that, we are within that 10%.

Mm-hmm.

Right.

So we do get a lot of people who are amazing negotiators, who are incredibly successful business people, and in their context, they’re great at it. But when they come to Vail, I need to do a little bit of education on the best way of negotiating to get the right home at the right price.

Mm-hmm.

Because sometimes different negotiating techniques, depending on who the realtor is on the other side, a lot of the sellers, I know who the sellers are because we’re a small town. We have to develop negotiation strategies that fit for that particular house.

Right. Right. I’m nodding along to this, because I think for all of our listeners who are

doing real estate long distance, this is so important. When I was an active real estate agent in Chattanooga, Tennessee, I helped so many long distance investors, and we had to pre-educate them on how negotiations are done here, because Chattanooga, I suspect like Vail, is a very relational market. It’s not a huge area. And if you make a low offer thinking they’ll come back with a counter, they’re not. They’re just going to come back and say no, and they’re not going to want to sell to you anymore.

Yes.

there’s an emotional aspect. So for all of our listeners, this is real if you’re investing long distance.

Yes, and real, yeah.

And we also have on top of that emotional relationship and the emotions that get involved, it’s even more pronounced here because almost all the sellers have the wherewithal to not sell. They put it on the market because they want to sell, obviously, but they don’t have to sell. And most of them with short-term rentals

Right.

Mm-hmm.

can either offset most of their expenses and carrying costs, or all of their carrying costs. Our property taxes are very low here. So carrying costs are very low. And they get to use it on a powder day. So there is not that need to sell. So if you come in at the wrong number, if you try to, for lack of a better term, bully the seller or fish for a good counter, you wind up not getting them.

Yeah. Yes. And that can be hard for people from some markets or regions to understand. Now, Mark, I’d like to do a bit of a tangent here, because we have so many real estate investors who listen, and you mentioned the short term rental market. So for a potential short term rental investor who’s listening, in a nutshell, how would you describe the short term rental market in Vail?

It’s interesting. In ski towns and vacation homes throughout the country, there is real pushback against short-term rentals. I’m involved in the Resort Alliance, which is a subgroup of resort associations of realtors, mostly mountains, but some beach areas, that get together, and we’ve been doing studies and working on ways to push back against

the onerous short-term rental regulations. Vail happens to be a pretty business-friendly, laissez-faire market. So our short-term rental regulations are more about guest experience than keeping people from being able to short-term rent. They just want to make sure that if someone is short-term renting, the guests who rent that

are having the Vail experience, and not a bad experience, because we care about every one of our guests, whether they’re in a hotel, staying with friends, owning a home, or renting a home. So with our short-term rentals, I do get quite a few people walk into my office. I’m right here in Vail Village, and they talk about wanting an investment. And

Right.

Right.

we start talking cap rate, and their expectations are a normal cap rate, what an investor would expect. And in Vail, you are doing really well if you get a two-cap. This is not a cash flow market. And if you want cash flow, as you know as an investor, a strip mall in Denver gives you a whole lot more cash flow than a second

Okay.

or vacation home in Vail, even if you’re short-term renting it. But it’s a lot more fun to own a home in Vail than a strip mall in Denver or in Louisville, Kentucky. So if you’re going to use the property in addition to investment, it works because of the appreciation. It’s a long-term play. I ran some numbers from like 1980 to right before COVID,

Ha ha ha.

Right.

so it included the Great Recession, included some other smaller recessions, and we are averaging over seven percent per year. And that doesn’t include the hundred percent increase from post COVID. So forgetting that as an anomaly, we are over seven percent per year in appreciation. So as long as you are not forced to sell at any particular time,

Okay.

COVID, right?

and you can sell when you want to, you theoretically will make money on your Vail investment, but you’re not going to get it in a cash flow yearly basis.

Right. That was a fabulous summary of what the market is there. Gold star from a real estate investor there, gives people a perfect example, and I do as an investor think, okay, well there’s limited development that can happen there. Vail is a name that’s known around the world, so that tells me that appreciation’s going to be pretty solid there. So love that.

Good.

Right. And it’s a very sophisticated market. People know what they have. Even the banks in the Great Recession knew what they had. So I don’t think there’s ever been a real estate steal in Vail. You can negotiate and have a strategy and get in the lower range of market value, but you never get a steal here.

Right.

Right. And I think the flip side of that is when you have to sell, you don’t have to stress about people not realizing the value of what you have or having to sell at a huge discount, because there’s just tighter parameters around that market value.

Yeah.

Yeah. And there’s also almost no fix and flips here. Because of the sophisticated buyers and sellers and investors, the cost of a renovated home versus a non-renovated home really is just the difference of the renovation cost. So there’s really no room for profit margin.

Right.

Yeah, and I’ve seen that in markets as well, and it’s a good point to make there, and it goes hand in hand with that sophistication, like you said. Now, I know you’ve been doing this for a while, and I’d love for us to transition to where you can pass along some of your pro tips to other real estate entrepreneurs who are listening. So I know you have maybe over twenty-five years of experience with these transactions, and I’m curious if there’s been anything that you have systemized, proceduralized, or anything like that, anything where you can rinse and repeat and do things again and again that have made your life easier.

I’m a little bit unique in that I take pride in the fact that I think I’m uncoachable, because I’m just stubborn. I’m just a very old dog. But real estate, whether you’re an investor or a realtor or a second home, real estate is not rocket science.

We are not trying to land a booster back onto a little barge in the middle of the ocean. There is a very definitive roadmap to be successful in real estate, as long as you bring a certain level of competence, which actually doesn’t even have to be that high of a level of competence if you follow that roadmap. You need to prospect.

Exactly.

What prospecting looks like is different depending on what market you’re in. Now, I was just on a panel discussion for the Residential Real Estate Council for the certified residential specialist designation yesterday, actually, about it being the end of the year and what do you do to end the year strong. And I was the only vacation market. So

the other realtors, who are brilliant and very successful, were talking about pop-bys and events for their clients and all of that type of thing, but I can’t do that, because my clients don’t live here. So I prospect in other ways. Prospecting. You need to prospect. And when your pipeline runs dry,

Right.

look at your CRM, look at your list of past clients, look at your leads that you have, and just start making phone calls. Just do what you’re supposed to do. And if you’re prospecting and you’re following up, actually I used a bad term. I try not to use it. Past clients. There’s no such thing as a past client. It’s a relationship that should be ongoing. Make sure

Right.

that you are top of mind. You are always there. And when you reach out to them, in my opinion, do not reach out to them with a script.

You’re not a salesperson calling them. You’re someone who knows them. And for a one or two month period, you were best friends because you were talking four times a day. Continue that level of relationship, because this really is a relationship business from the realtor perspective. From the investor perspective, look at the roadmap. There’s thousands of books, and everyone is just a variation on the same

Ha ha ha.

general patterns. Sometimes an author or a coach sings to you, and that’s great, and then you follow that program, but it’s basically the same program. Did I answer that specifically? Yeah.

Yeah, I think that’s a good point, and that’s something I’m laughing about because I say multiple times that real estate is not rocket science, so we’re on the same page there.

Yeah, it’s

Now I know as we worked on scheduling this podcast, you do have some support, a support team that helps you do all the things you do, because I know you’re so active as both a real estate agent, and you also have everything you’re doing civically, with all of that, and then you’re involved in so many different realtor associations and committees and all of those things. So what does your support structure look like behind the scenes to help you with all of that? And then how did you decide what you keep on your plate versus what to hand off?

It’s very interesting that you asked that, because when I was looking at your website, I know that’s a big point of what you work on and are really into. And as I was reading through that, I was thinking I might need to have a different type of relationship with you than just being on the podcast; we might need to talk about that. Because for almost the entirety of my career, I’ve been a one-person show. I just do it all. Luckily, I’m blessed to be in a market where I don’t have to do 60 deals a year. I do fifteen to twenty, and I’m doing fine. And that gives me the time to work on NAR stuff and organized real estate stuff and do the things that are my why. So

Right.

there’s also a strategy there. A lot of people, when they hire somebody or bring on a virtual assistant, or bring someone on who’s a non-virtual assistant, or even a transaction coordinator, I think the last thing I would ever bring on is a transaction coordinator, because every time I get to talk to my clients, it creates that relationship

and strengthens that relationship. So even if I’m calling to say, hey, the due diligence deadline is today, they hear my voice. I like to talk, so it’s rare that the phone call is just me saying, hey, the due diligence document deadline is today, bye. So it’s creating that relationship, but

Ha ha ha.

Ha ha ha.

when you ask that question, right now I am in the process of bringing someone on and figuring out what the structure is. Are they going to be an assistant? Are they going to be a coworker? Are they going to be a colleague? Do I pay them, or do they work for commission? Do they search out their own business? They would have to be licensed. So I’m in the process of actually strategically thinking that through right now.

And I do have an assistant in Claude. I use AI despite the problems, despite some of the inaccuracies, because I don’t know any humans that are accurate a hundred percent of the time either. I’ve figured out ways to save myself a lot of time using AI.

Ha ha ha.

huh.

Awesome, awesome. And I love how you’re being so intentional and thoughtful as you structure this role and think about bringing someone on, because that’s where a lot of people get into trouble, when they don’t think intentionally and do it with some forethought, and they’re just doing it reactionary because they’re at a hundred and ten percent, overloaded, and they’re like, my gosh, I need help, and they just hire as fast as they can. That’s setting you up for success, Mark.

Good to hear. I hope so. So far, so good. And it’s an interesting thing, the thought of bringing somebody on, especially when for years I was very much a one-man show, I would do everything from my prospecting. And then now, about six months ago or so, I hired a firm to help, not just with social media, but they interview me every

once a month, and they book me on some podcasts, like this one, and they interview me, and then they write with me stories that then get placed in media, which helps me get picked up by the different AI systems. And I become a source. And that’s one of the goals. So it’s not so much specifically looking for someone to buy a house in Vail,

Okay.

Right.

but it’s to create my place within the real estate world. And the reason I’m thinking about bringing someone on now is that I’m going to be the ’27 president-elect of the Colorado Association of Realtors, and the ’28 president, and then past president. So I know that there’s going to be a lot more tugging on my time. So I want to have somebody

Right.

who’s here in Vail, who loves the town the way I do, who has the same sales philosophy and can get along with my clients, so that we can work together and make sure the business stays strong.

Right. I love that. And I think also what you said about how you brought on this service firm that’s helping you with the social media and with placement, that’s another source of not doing it all ourselves. We don’t have to bring it in internally. We can hire that out. And that’s something everybody in the real estate industry should look at. So I think you highlight a great opportunity to leverage as well.

But I will never give up that relationship. Opportunities to have human to human contact with my clients and my friends. That’s what ensures a real estate agent’s success. Brokerages fly their flags, brokerages can give you your tech stack, but the relationship belongs to me, the agent.

Right, that’s a good point. Well, there has been, I love this conversation, Mark, there’s been so much wisdom shared about the real estate market, about Vail, about these resort, vacation home communities. I love this. So if somebody would like to reach out, Mark, and continue the conversation with you, follow-up questions about Vail, or if we’ve got a listener who’s like, my gosh, Vail sounds amazing, I can’t wait to buy a place there, what is the best way for them to contact you?

I answer my own phone. So call me at 970 331 5821. I will pick up. I don’t have an automated pickup system. It’s so funny, realtors are the only ones who say, my god, it’s a number I don’t recognize, I better answer this. Everybody else pushes it off. We all answer. My phone number’s out there, who knows, it could be someone wanting to buy a thirty million dollar penthouse, I better get it. It never is, it’s always a scam, but that’s okay.

I love it, I love it.

Hope springs eternal. Well, thank you so much, Mark, for all of your wisdom shared. And for our listeners, that is a wrap on today’s episode. Please join me again next week for another fabulous conversation.

Right, exactly.

Thanks.

The post The Ultra-Luxury Market Where Cash Flow Isn’t the Point appeared first on Adrienne Green.

I am Adrienne Green, and in this episode I talk with Sandy Lee, who spent over 30 years in engineering and construction before buying her first short-term rental at 52. Within two years she had grown that single ski condo into a four-property portfolio spread across Colorado, Alabama, North Carolina, and Texas, all while spending just five to ten hours a week managing it. We get into the systems that made that possible: how she automated guest communication, how she chose markets before the growth was obvious, why she eventually hired a revenue manager, and the pricing mistake that cost her real money before she fixed it. If you are managing property in more than one market, or wondering whether it is too late to start, this conversation 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!

Hello everybody, welcome back. I’m Adrienne Green and today we’re here with Sandy Lee. As you know, here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start, and Sandy is a great example of that. Sandy, thank you for joining me.

Thank you so much for having me.

For our listeners who don’t know you yet, can you give a quick snapshot of your portfolio today? Properties, locations, what kind of investing you focus on?

I focus on short term rentals only. My vision was that I wanted some vacation homes that I could travel to during retirement and then also do something good in the world with some hospitality. So I have four homes in Steamboat, Colorado, in Orange Beach, Alabama, near Asheville in North Carolina, and then one in the Hill Country in Texas.

I’m excited for a few things here with you, Sandy. I’m excited to talk about going deep into that one niche for you, which is short term rentals. And I’m also excited to talk about how it is managing these properties in these four different markets. But we will get there over time. Let’s start with, I understand your background is decades in engineering and construction and you bought your first rental at fifty two. Talk to me about that. What made you start real estate at fifty two?

I love being the super old starter here. It’s interesting that I didn’t start until I was 52. I didn’t even have this thought. I spent all these decades in engineering and construction, really loved going to work every day. I really loved the idea of building something and seeing it finished, and that was a wonderful career. But as I entered my 50s, I could see the oil and gas world starting to shift a bit with everything that’s happening in the world.

I could see that maybe my 50s weren’t going to be the same kind of career that I’d had in other decades. And I felt like I’d done it. Meanwhile, my son was going to school in Colorado and kept joking about getting a ski condo. It sounded like a joke at the time, but it clunked around in my head in the background enough. Meanwhile, I was running our private equity group at the company and learning about long-term investments in a way that I hadn’t before. And it all just started to click, that maybe all of this could come together with some long term investments that really build wealth in the background.

There’s so much to dig into there. My husband is an engineer by training as well and engineers can be very comfortable with their day jobs.

Absolutely loved it. Loved it for so long.

You make good money, it’s safe, engineers like security. And yet sometimes we get that rude awakening, which thankfully for you wasn’t too drastic. It was just a little bit of an inkling that those jobs aren’t as safe as we thought they were.

Sure. And there’s a great thing about climbing the ranks in the company, and that goes great. But then what? As the reorgs keep happening and things keep shifting, it just wasn’t as fun as it used to be. And as wonderful as that private equity experience was for me at the end of my career, it just wasn’t who I am. But what it did give me was so much training in financial modeling and really understanding how investments work.

And it became clear that my great big 401k wasn’t doing what I wanted it to do. And these investments can do so much more. They provide me places to vacation. They provide me great wealth building tools in the background and cash flow to live on every day. I was like, okay, this is the big eye-opener that I just hadn’t seen before. I had been thinking about long-term rentals and they just weren’t clicking with me. I went and looked at a few properties and it just didn’t seem like what I wanted to do.

So this vision came over time, but now I travel to all of these properties. I really enjoy them in the off seasons when they’re not making money. And then they have this great business for me as well.

I love that. As somebody who is a full time traveler right now, I can totally relate. You get to have the houses set up the way you want them with the amenities you like in all these different locations.

Right. And you find that what you like is probably what other people like as well. So it does feel like going home when you’re running it for other people. There’s a thing to that. But after I go in for half a day, I generally do my own little deep clean and then it feels like my house again. And I get to enjoy it for a couple of weeks, make some upgrades while I’m there, do some work, make it better for the next guest. It is a life that I am really loving.

Love it. Now you mentioned that when you were working within the private equity scope you were able to learn skills that transferred, which is amazing. And that’s what we tell people all the time. If somebody can pay you to build the skills that you are going to use in your entrepreneurial journey, go for it. What skills from your engineering career turned out to be surprising assets when you started investing?

My engineering career spanned engineering, but then project management for a lot of my career. And then I ran some of our services departments as well. I couldn’t have scripted it any better, but I think this is true for everybody. There was a time when I got to run IT, when I got to run HR, but then there were all these years of project management. When you think about that, every home you buy, no matter what kind of rental it is, is like a little project that you’re managing start to finish.

All of that translated beautifully. The leadership for sure, everybody has a team and what it looks like to lead those people. It was really valuable to understand how to relate to people and what that really matters in your business. But then the financial modeling part from the private equity, I got to go to Columbia and train for a while. All of these skills just sort of came together to be what felt like the perfect resume for this business. But again, I think everybody has that same thought when they’re 50. They’ve gathered a lot of life skills that they may not even be thinking about in their career.

And that’s where, if you’re out there doing something and you’re living life and you’re trying things, rather than just scrolling on your phone all the time or playing video games all the time, you’re going to be learning some skills that are going to be helpful. So I love your example of that.

Absolutely. My mom had this quote that she always said: make a decision, do something, do not be stagnant. She really taught me that from a young age. And it’s proving to be true. I’m retired, but I’m not retired. I keep starting businesses. I love it. I love all the activity. And certainly running short term rentals has given me a place to put some energy.

Well, and your mom’s quote leads perfectly into what I was going to ask you about next. When I was an active real estate agent I worked with a lot of engineers who wanted to get into real estate investing, and I love engineers. My husband’s an engineer, I can work well with engineers. The challenge was, engineers are notorious for analysis paralysis, for waiting for the right time to start. Or it needs to look on paper like a home run before we’re even going to make an offer. What would you say to a fellow engineer who is in that mindset or facing that challenge?

This is a great question. I get this all the time. Actually, my consulting clients, a lot of them are engineers because they’ve connected with me on that way. So I personally call myself an 80 percenter. If 80 percent of the deal looks great, and in this case it’s an asset that you can sell two years from now, get comfortable with that and decide whether you can go forward with the purchase. It does not have to be perfect, but one of the great things about this business is how those returns stack. You’re not just making money on the cash flow. It’s important that it cash flows. It’s important that you have the reserves to be able to handle anything that comes up. But it’s also making money on appreciation. It’s making money because your guests are paying down your mortgage. And then there’s some tax benefits. So for that person who’s still an engineer or whatever they’re still doing right now, take advantage of those tax benefits while you’re still working because it will multiply. That’s an important thing to do while you still have that big salary.

Very good points. I love it. And I love how you mentioned all the different benefits of real estate investing, which I agree, they all compound.

They all stack together beautifully. And I never knew that until I was 52. Until I really looked into all this. I was like, wait a minute, this is great.

Alright, so what I’d like to dive into now, Sandy, is your systems and delegation, because I understand you grew pretty quickly. Short-term rentals are a lot, as somebody who has a few of them, and you have them all in different markets. I’d love to hear how you figured this out. So we’ll go first with, you went from one property to four in two years, which is a pretty fast pace. What systems did you have to put in place to keep that growth manageable?

I think this is really important, especially for new investors who sometimes might have a tendency to just buy a property and throw it on Airbnb to see how it does. I think that’s a big mistake. I think even with your first property, if you set up your tech stack right from day one, including a property management system, something to handle the dynamic pricing for you, how you’re going to do your accounting, if you set these things up from day one, you’ll be set to scale in whatever way that’s right for you. I think it’s smart to do it even with one property because it saves you so much time in systems and operation. I kind of made my business a button click. A button click is obviously an exaggeration, but from day one, so many things were handled for me by the technology.

Right. So you really approached and set this up from an engineering mindset of, we’re going to get the systems in place, we’re going to make it do it right the first time, not good enough is perfect, not slap it together, we’re going to make a system, and that’s what allowed you to then go boom, boom, boom, rinse and repeat.

Absolutely. And for one property, that looks like maybe $100 a month in software. Sure, there’s some work to piecing those softwares together and putting them together. I think it takes about 40 hours to really set up a good listing properly from everything that you have to do. And then there’s the time on site. So maybe 60 to 80 hours total when you consider the software, the setup, the furniture, everything, whether you’re doing that yourself or delegating some of it to other people.

There’s an investment of time at the beginning, but does that pay off. To your point about how this looks in the rest of my life, I spend about five to ten hours a week now on my four properties. It’s just not a lot. And I think that’s largely because of the systems I have in place.

Okay. So let’s get into those systems, because short-term rentals have more moving parts than long-term rentals. You’ve got turnovers, sometimes multiple times a week, you’ve got guest communication, you want to manage that pricing and keep it dynamic and appropriate for that season. So how do you delegate all of that without losing control? And if part of that is the tech stack, feel free to dive into that.

Sure. So the tech stack was the first most important thing. And I use Hospitable as my property management system. I think there are several great ones out there, but I love the fact that Hospitable, even when I set it up many years ago, already had some tools in their messaging that helped make that more automated than some of the others. So my messaging, all of the standard ones go out automatically. When I get a new reservation, it welcomes the guest with the new reservation.

When I get, for day of check-in, it’s like, hey, happy check-in day, and gives them all of the details, all the way down to asking for that five-star review at the end. Those five messages that guests get are automated, so I never touch a button. Turnovers usually happen without me even knowing that they’re happening, which is exactly the way I want that happening in my business. The next most important thing, of course, is the people on the ground. I’m far away from all four of my rental properties.

Right.

And I wanted it that way because I wanted them to be vacation homes for me and my extended family. But getting a good cleaner and a good handyman are absolutely paramount. And if you’re buying in a market that has a lot of short-term rentals around, you’re probably going to find a cleaning company that could maybe do the handyman work for you as well. A lot of them have been smart enough to set up their businesses to sort of have that monopoly on you. And that’s been great for me. I’m happy to push the easy button there and have people that I can text. You treat them well enough that they want your text when it comes in. That’s the leadership piece. And then they’ll work hard for you, give them great bonuses at the end of the year. I think it’s important to have a team you can count on and treat them like gold because they really are the most important part of your business.

That makes sense. Now, has any of your system changed as your portfolio grew or as you’ve evolved as a short term rental host? Is there anything you’re doing now that you didn’t even think about on day one?

Yeah, there are two big things and I would love to dive into both of them. The first one is when I bought my first place in Steamboat, I don’t think I knew on day one what a business this was going to be for me. So that one I actually started with a property manager. And by the next property, which was less than six months later, I set up my systems and handled it from there. That first property, I had to wait for that contract to be over to get out of that property management contract.

They took 29 percent of my revenue. And I’m sure that’s a lot of the stuff that you talk to your people about, that it’s not as hard as you think if you delegate all of the pieces properly. And that was the thing. This is the whole reason I teach now, that I don’t want someone making the same mistake I did and thinking that they can’t possibly do this in another state without a property management company. So that’s something I changed, absolutely.

Now the other thing I changed was that I’m using AI a lot more than I was even six months ago. Certainly years ago, it wasn’t really a thing. But I’m using AI in my tech stack, not for messaging. When there’s a problem or a question, I love to answer those myself, but I only have four properties. I’m using AI for all the data things that I did by hand before in spreadsheets. I’m using AI for pacing studies and for goals worksheets and for that three-month look ahead. I use it for calendar gaps. I use it to write some emails to past guests to see if they’d like to come back and stay with a discount. Some of my favorite things, I’m using it for guidebooks, and they’re so much better than the guidebooks I had before because frankly AI is brilliant. And then I’m using it for supplies. You’re talking about systems.

Stocking supplies in four different markets is a whole complex thing. I use Minoan, but I also use Walmart. I also use Amazon. So I’ve set up a specific email that my AI has access to that gets all of those receipts. It has this great complex data set available of what’s been ordered for each property, what guests are arriving, because it connects to my Hospitable, how much the usage rate is for everything down to sponges, and then when I’m going to likely need to order again. So I get little reminders from AI: go order some white towels for this property, or some sponges for this property. I just find that amazing, frankly amazing.

Yeah, that is. Because that is rather complex, but it’s great because we can have that data of when did we do these things before, but without AI it’s so difficult to get, analyze, and utilize that data.

I think I was just super reactive before, which was okay, but it brings a little bit of a stress level into your life. The more you can be ahead of some of these things by having the data in front of you, the smoother your business will run.

And you mentioned part of the supplies issue is four different states, that’s a lot. Let’s talk about scaling across different markets. I understand there’s some personal use aspect, there’s probably also some market aspect. What does evaluating a new market look like for you before you decide that you want to buy in that market?

So I talk about the personal use a lot, but really it’s a business first and foremost. The numbers have to work. So when I think about going into a new market, I really try to look at not just where the numbers have been, because that’s everything that’s published out there, but I try to look forward and see where a market is going. What’s going to happen in the next three to five years in that market that’s going to make the curve of those revenues higher than it might be on paper?

Some examples of that, because I don’t think that translates without really talking about what I mean by that. My Steamboat property, the whole reason that we bought there in the first place, and that was my first one, we loved it. We had gone there forever. But Aspen had just purchased Steamboat a couple of years before. They were putting in a new gondola, they were adding a bunch of land on the top of the mountain. And at the same time, Steamboat was about to put in some strict regulations on short-term rentals.

So I knew that if I bought in the green zone, I’d be part of a shrinking supply of short-term rentals for an expanding mountain. And that was the best math that I could think of as a good reason to get into a market where the property value was definitely going to go up quite a bit. And it did, it rose 25 percent. This was way after COVID. This was 2022. So the prices had already doubled. It still went up another 25 percent after that.

To me, that’s what it’s all about, finding that market that’s on the rise. Same thing near Asheville. I bought on top of a mountain where there was a ski resort that was closed but being renovated. So I took the bet that it was actually going to open, and it did a year later. So things like that everywhere. My Alabama property, the Gulf Shores airport, had just gone commercial. So I bought a year before the airport went commercial down there and it finally opened. It was actually late on the schedule. But all of that is just going to make some of these markets grow a little faster than others. That’s always the thing that I’m looking for.

That makes a lot of sense. Now let’s get into the logistics, because kind of like what you talked about with supplies, managing properties across different regions creates real logistical challenges. You’ve got four different cleaners, four different handymen. So how do you keep standards consistent when you’re not physically present in each market?

To say that I keep standards consistent is pretty tough to do. You’re right. I started out thinking like an engineer that I could just have a checklist and a cleaning book and it would be the same everywhere. But what I’ve learned is that you have to flex to how your people work. If you let them do what they do best and you really work with them and get to know them, I think that works better. So I have two cleaners that really like to work in Turno, which is a fantastic system. I put all of my pictures in there of how I want it to work and that’s all automated. I have another cleaner that wants to be paid through Cash App. No problem. So maybe the answer is that I keep my quality standards up with great communication, but my actual standards for how I work with them, I flex to what they need. Now I only have four properties. Maybe somebody with 20, 50, 200 has to come up with a different way to do things. But with me only having four, it’s able to flex to what the group’s need is at each location.

That makes a lot of sense, because I feel like a lot of short term rental owners go in with a cleaning checklist and all of this, and they want to micromanage the cleaner, which I get, because we want to feel like we can control the quality by controlling the process. And yet some cleaners have their own process and it might be better than ours because they are professional cleaners, not us.

Right. I’m getting all five star reviews. So I cannot complain about the work that they’re doing. I have to celebrate it. I have to tell them great job. I have to ask what they need from me. And then I have to kind of let it go a little bit.

Right, that’s a key part of leadership, realizing what we can control and what we trust others to handle.

What we shouldn’t, right.

So was there a property or a market that taught you something about what not to do?

Absolutely. I think any of us would be lying if we said otherwise, that it’s all been perfect. There have been a few great lessons. One was in Orange Beach. I bought a new build, first of all, maybe not the best investment, but it does pay for itself. So that home is doing just what I wanted it to do. But because I loved that home so much, I priced it like it was a beautiful home.

And I really learned some lessons around that. For one thing, I outsourced my revenue management about a year and a half ago. That’s one of the smartest things that I’ve ever done. It’s an investment for sure, but when I compare it to my yearly revenue, it’s nowhere close to what I’m bringing in more by having a revenue manager. What they do is they control price labs for me, they advise me, we meet once a month just to go over everything.

And I’m definitely making more money with a revenue manager in place who looks at it every single day in some detail. The specific lesson I learned in Orange Beach was I had a rule that I was never going to price a night less than the cleaning fee. Well, that was just silly. That was just pride over, I love this house and I’m never going to price it under this number. And my revenue manager was like, well, if you do, you’ll probably make 10 percent more.

And sure enough, my occupancy went from forty-three percent to seventy-one percent during that year that I made that shift. And my revenue went up ten percent. So you can see, I priced it much lower, filled up a lot more of it, and made ten percent more money, which for that market was significant.

Yeah, that’s a huge jump. That’s amazing. Now, what shifted in how you thought about your business once you retired from your engineering career and this became your full focus?

So all of that happened so quickly. I bought those four properties within two years, and that last property came right after I retired. I always say, and then I retired. It was all sort of at the same time. I took my last bit of stock from my company and I bought one more property. I did that very specifically because I wanted the cash flow to be able to support my life without pulling any money out of savings. So that was the goal. So what shifted really was just that I had more time and more flexibility. I think I always thought about this like a business, even when I was working and still running three properties. I just had less time. But now that I have more time, I’m doing so many other things. I’m releasing a book in a couple of weeks. I’m running this other business to help educate others because I found that there was a real gap in the short-term rental education market. And so I’m just finding more time to do more projects. That’s all it is.

When you take somebody who’s a type A hard worker, likes to help other people, and you take away their day job, what do they do? They give themselves more jobs on the side.

Absolutely. So many more jobs. I’m busier now than I have ever been, but I’m still traveling like crazy and I’m handling that busy from Steamboat and from North Carolina. I can run this business from anywhere. I went on a three week cruise to Australia and New Zealand at the beginning of the year. No problem. Ran it from there. No big deal. An hour a day, right, it just wasn’t a big deal.

Love it. As a big traveler, I’m like, yes, that is part of the joy of real estate investing. We can have these businesses that we can run from anywhere, even with something like short term rentals, which people may have this limiting belief that you have to be hands on, you have to be present. You can still run it from anywhere. It’s cool.

You really can. It’s not like the guests want to talk to you every day. They want a few questions answered, but they don’t need to have huge relationships with you while you’re there. It’s just another set of procedures that can run in the background. I will say it might be better for someone who doesn’t easily get super stressed out, who is able to let things roll off their back, because there will be issues. There’s always going to be issues.

That’s a good point. Now let’s shift to some of these other projects that you’ve started since you retired from engineering. Let’s talk about how you started teaching other investors through STR Jumpstart and what’s a big misconception you see new short-term rental investors walking in with?

I started at fifty two, but I really started researching at age fifty, and I listened to every podcast I could get my hands on, every book I could find. I ordered them all and I read everything. I tried to find training and I could not find what I’m doing now. And so that’s why I started it. It was years into it, just about a year and a half ago, that I even got this idea, and I didn’t put it into place until about eight months ago.

STR Jumpstart is step-by-step lessons. It’s got a ton of downloads, it’s got a 12-year financial model that is really in-depth that you can use. You can put numbers in for 10 minutes and have yourself a quick evaluation of a property, but I use it for my long-term day-to-day financial modeling. Why I started that was really just because I think I get so much joy out of this business. I love it so much more than I ever thought I would.

And it’s that combination of getting to buy homes and decorate them and be hospitable to other people, be a part of their vacations in their lives. And then I get to share these homes with my kids, my brother and sister-in-law, their kids, their grandkids. We all get together for holidays together at these homes that I honestly never would have been able to afford on my own. It’s not like anybody can just go out and buy a bunch of houses.

So that’s why I started, really just because I wanted to share that joy and love that I have for this and help other people set it up like an engineer, maybe is a good way to say it. Biggest misconception, you asked me. I think the biggest misconception is maybe how hard it looks from the outside. It can certainly be overwhelming. Maybe even listening to this conversation between the two of us, someone might be a little overwhelmed. But when you get into it and see the step by step, take it one step at a time.

It’s just not as scary as people think it is. And the great thing about this kind of business is that you can always sell the home if it doesn’t work out. It’s not like starting a business that is a restaurant or something in a storefront or a bar. You can sell the home if it doesn’t work out. I find it to just be the most amazing investment ever.

There’s a lot of good points in that, Sandy. I love how you built what you wanted when you were starting. And I also love what you said about people being overwhelmed. I get that too. And I know in our family one of our sayings that we come back to a lot is, how do you eat an elephant, one bite at a time, because we can really break things down. And that’s what I want my kids to know so that they don’t get scared and overwhelmed and then just don’t take action.

Absolutely. It’s like we said at the beginning, move forward, do something, don’t be stagnant, don’t be scared.

Yes, exactly. Now if somebody is sitting where you were at, fifty to fifty two, doing this analysis, weighing whether to make the leap and get into short term rentals, what’s the one piece of strategic advice you’d want them to hear first?

Certainly to go in with their eyes open. I think it’s important to educate yourself on the business before you start. And I think it’s important to do a lot of analysis on different homes before you decide which one to buy. What you’ve heard from me so far is a whole bunch of joy, go do it, this is amazing, everybody should do this. And I definitely agree with that. But I also think people need to really be ready, educate themselves early, and do some analysis before they start.

I think some of the people who got in too quickly a few years ago are the ones that are maybe backing out of it now, which is great for the rest of us who still want to be here. But the number of short-term rentals went greatly up during COVID and now it’s coming back down again, which is, I think, good news, because the operators who stay should be the ones who care about the business, who care about putting out a good product.

I know I was in a women’s mastermind where, as real estate investing was all the rage post COVID, they were all getting into it and they didn’t realize. I’d ask them, what are your numbers? What are your projected returns, et cetera, because it’s an investment, it’s a business. And they wouldn’t have it. They were just doing it because it was a fad, and a lot of them have now since left the space. So I can say from personal experience, I see exactly what you’re saying there, Sandy.

My blood pressure just went up when you said that. You’ve got to know your returns. It’s so important to figure out whether your money is working harder for you in this business versus the stock market or wherever else you had your money before. I think that’s all about calculating those annual returns in a way that makes sense that you can compare to other places you’d put your money.

I love how you said that. Now, Sandy, as we wrap up, if somebody would like to connect with you or learn more about STR Jumpstart, what is the best way for them to do so?

Sure, they can find me at strjumpstart.com or on all socials at STR Jumpstart. You can find me on Insta. I’ve just started on TikTok, which is a whole new thing for me. I’ve got a book coming out September 15th called Building Joy. And it is just what you’re hearing from me today. It’s all the stories behind the business and how much I love it and how someone could get started.

I love all of that. Well thank you so much, Sandy, for joining me today. And thank you to our listeners for listening to another episode. If you got value from this conversation, make sure to subscribe wherever you’re listening, YouTube, Spotify, Apple, and then join me again next week for another great conversation.

Thank you so much.

The post The Real Cost of Skipping a Revenue Manager on Your Rentals appeared first on Adrienne Green.

I sat down with BJ Gremillion, founder of Property Rush, and this is one of those conversations where the practical details stack up fast. BJ walks through how he rebuilt his entire business model after realizing he was the one absorbing all the risk on every flip, why he now front loads major repairs like the roof, AC, electrical, and plumbing before a property ever reaches an investor, and what actually separates a trustworthy long distance operator from one that will cost you. If you invest out of state, work with a property manager, or have ever wondered whether you are the one carrying too much of the risk in your own deals, this conversation 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!

Hello, lovely listeners, and welcome back. I’m Adrienne Green, and today we’re here with BJ Gremillion, which I’m super excited about because he is my own property manager on a couple properties. And BJ is a living example of how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start. So thank you, BJ, for joining me today.

Happy to be on. Thanks, Adrienne.

So for our listeners who do not know you yet, can you give a quick snapshot of who you are and what you’ve got going on right now as an investor and as an entrepreneur in the real estate space with Property Rush?

It started in Arizona. I started investing in real estate in Arizona in 2009. About fifteen years later, we experienced our first crash, in 2022. That was a big year for us because our business was centered around land acquisition and development at that time. If you know about that and interest rates, you understand where I’m going with that. So after that, about a year before 2022 happened, we started looking at other markets, one of which was Chattanooga. We saw an opportunity there. So we ended up leaving Arizona after about twelve years with my prior business partner.

We ended up going to Chattanooga, Tennessee, because we saw an opportunity in the real estate world. I’d done a lot of research and looked at a lot of different markets. We visited about four different markets, and when we landed in Chattanooga, it clicked. It wasn’t anything other than just a gut feel that we were in the right place. So we started investing and bought a few homes just to test the water.

Because that’s what we do. And it went well. We felt good enough about it. So there came a point where we had to decide. It was like the proverbial thing, one foot on the dock, one foot on the boat. You have to figure out which one you’re going to pick. So we decided to go with a canoe on that one and travel across the country to Chattanooga, Tennessee. I have a beautiful wife, five kids, and for us that was a big deal because we had never known anything but Arizona. All of our kids were born in the same hospital, my wife’s family is from there, a lot of our cousins on that side were from there. So it was a big deal for us. We ended up leaving and went to Knoxville first because we felt that would be the right call for schools. Turns out, funny enough, after a year

we were flipping a home in Chattanooga. My wife fell in love with it. We ended up choosing to live here because I was commuting back and forth, and really we had just lived in Knoxville for the kids’ school. So then we ended up coming to Chattanooga, and it’s funny because our kids will tell you now that they love the school they’re in now more than they did in Knoxville. So I wish we could have known that in the beginning and not

had that chapter of one year in Knoxville, because that would have saved us a move and all that. But everything happens for a reason. So we’re here. And to answer your question, sorry, this is a longer answer, but what we ended up doing was creating a business model that we felt would serve people well. It’s a simple turnkey property management company.

What that means is we focus on start to finish. We find properties we feel are in good areas, we purchase them with our own capital, we remodel them with our crews to our standards, which are very high standards, and then we turn around and sell to an investor who then has us manage that property for them. So the idea behind the business model is to help

wealthier individuals who have some discretionary income looking to invest in real estate, but they don’t want to be in real estate. They don’t want to have a job in real estate. They don’t want to figure it all out on their own. They’re smart, in my opinion, to not have to get into the weeds and figure that all out. Instead, they skip the line, go straight to us, and we’re able to provide them a great product, a great property with the management included, so they don’t have to worry about lifting a finger. So that, in a nutshell, is why we’re here.

I feel like we could dive into pieces of that one answer and it would take the entire episode. But I know there’s a lot more. For listeners who know my story, I moved to Chattanooga in 2020 before leaving at the beginning of 2020 for our travels. So obviously BJ and I saw the same thing, with the real estate market being such a great thing in Chattanooga. Now, on the personal side, BJ, I am curious.

What was so amazing about this house that you guys fell in love with and wanted to move from Knoxville to Chattanooga?

For us, community is a big deal. The subdivision we found is in Mountain Shadows. We were approached by a lady who wanted to sell it for a crazy price, and I said, are you sure? It was going to be a great flip and we were excited about that. But then my wife, she does the design on a lot of the homes. When she came out, it’s funny, she’s talked about this because we’re big believers.

We prayed about all of our decisions, and she didn’t really feel like she got an answer about moving from Arizona to Tennessee. It was more of, I trust you, and I don’t know if this is the right decision, but I’m going on faith based on you. So no pressure. That was a little scary. But then, on this move to Chattanooga, there was a point where she was walking through the home and she started

picturing every kid’s room, and she was like, they could be in this one, they could be in this one. And as she was doing that, she said, wait, we’re not going to live here though, that’s weird, why am I doing that? So it was after that she called me and said, why are we selling this again? You’re commuting back and forth an hour and a half every day, why don’t we just move there? And I said, it’s because I didn’t want to say anything and have you

be upset with me for even suggesting the idea, since you’d already moved across the country. So it had to come from her. And when she said yes, I thought, great, because I’d been thinking that the whole time, but I didn’t want to say anything because you’d already done a lot as far as moving out here. So that’s how it worked.

I love that. And what I love is, I have a community for women real estate investors, Heart Rock Collective, and we talk about women in real estate investing and one of the special gifts that women have is the sense of intuition. It’s funny, I remember hearing about some guy in real estate who said he will never do a deal unless his wife gives her

blessing, no questions asked. So I love that you guys used her connection and her intuition there as a major deciding factor.

She is the rock. The best business advice I have ever received is not from a coach or some guru. It’s always been from my wife. She really is our rock and foundation. And also, she is the designer, but it’s such a cool thing to have, because I believe everyone has gifts given to them. And usually we get a couple, right? It’s not like

we get the whole card deck. You get one or two that you’re probably good at or natural at.

for me, I’m not great at vision. I’m not great at looking at a home and understanding the potential and seeing where things can go. She has an innate sense, she can’t believe that I can’t see it. It’s great though, because I say, look, I don’t know what you’re talking about, but if you think it’s a good deal, I’m doing it, because you’re going to figure it out. And every time, without fail, she nails it and exceeds what I even thought. She makes fun of me because if I go to investors and do a walkthrough with them and start

telling them what we’re planning on doing, she says, whatever he told you, just stop, don’t even listen to anything, forget it. Because sure enough, she’ll go through and say, no, we’re actually doing this. She would have done that at night in bed, doing floor plans on her iPad, and I had no idea. So we’ve learned to stay in our lanes.

Well, and the other thing you’re hitting on that resonates with me is, we don’t all get the whole deck of cards. We all have our gifts, and the beauty of when we can partner with other people is when their gifts complement our gifts, whether that’s a spouse or a business partner, and then it’s easier for us to stay in our zone of genius because they’re each in their own areas.

Yeah, why do opposites attract? That’s exactly why, because I’m pretty deficient in a lot of these areas and they’re not. In a perfect world, you find a spouse that completes you, and then your kids get to enjoy it too. That’s why I’m such a big believer in marriage, it’s so cool. We were talking last night with our kids about this. I have sixteen as the oldest, down to six. We have six year old twins, and they’re my

favorite just because I love that age, and they’re twins, a boy and a girl, there’s nothing better. I was talking to them and they always go back and forth. They’ll say, Dad, you’re my favorite, or, where’s mom, she’s my favorite, and they go back and forth, and I say, guys, isn’t that so cool

that you feel that way about us. The cool thing is you get us both. Day to day it just depends on what they need. If they need nurture and love and consistency versus the wild, crazy, fun side, they get both, but in doses, not too much of one or the other. It’s a good balance.

Okay, we’re going to switch to another thing you mentioned in that first question, there are so many nuggets there. One of the things you mentioned is that with Property Rush, you keep people from getting another job in real estate. That reminds me of Robert Kiyosaki’s cash flow quadrant, where we go from employee to self-employed, which is where a lot of people go in the real estate world. They leave their W-2 and they’ve made themselves a job, flipping houses or something like that. Then they can

progress to business owner and potentially to the investor spot where the money is doing the work for them.

If I were to generalize, nine out of ten people go from employee to self-employed and just make themselves another job. I did that. And yet for people with a high income earning W-2, it makes a lot more sense to jump to the investor route directly.

I’ll tell you, it’s funny how timing works. This podcast, if you want to talk about how hard it is to be a business owner or run your own business, I could go on for a very long time, because there are times and seasons where you get kicked in the mouth over and over and you think

holy cow, I thought we were good at this. We’ve done thousands of remodels up to this point now. You’d think it would get to a point where it’s clockwork and it all works perfectly and it’s just a system. But then you realize you’re working with people

and you’re working with old homes that have problems you can’t foresee. So just when you think you’ve got it figured out, God has a funny way of humbling you quickly. I think we’re in that season of realizing there’s a lot of things we need to button up and do better on, and there always is. That will never go away, because we’re always striving for perfection. But I have realized that if

I could keep my job and still be in real estate, because I think everyone realizes they need to invest in the stock market and real estate. I saw something the other day that if you do not own assets, you will be left behind faster than ever before. Cash just doesn’t do it for you anymore, because, if you kept a hundred dollars in the bank in 2009 or 2010.

And that’s back when we used to think if we made a hundred thousand dollars we would be set, that was our dream. Now if you make a hundred thousand dollars, you’re borderline poor, and again it depends on lifestyle and where you live, but now we’re at a point where we need a much higher level of income just to get by and pay the basic bills. That really is because a hundred dollars back in 2009 is now worth about sixty cents

today, and that’s just from inflation, not doing anything, it ate away all that money. So you need to own assets, and I think the best hedge against inflation is real estate. That’s why we do what we do. But the reason people don’t do it is it’s like Everest. If you want to get into real estate, you’re starting at the bottom, and then you have to figure out, where do I buy, who do I trust, is this realtor telling me the truth, probably not.

Is it going to rent, I don’t know, and then who am I going to get to do the remodel, who am I going to get to manage it, am I going to manage it, and then with your budgets, throw that out the window, it’s going to go up thirty percent from what you initially thought, because everything’s expensive. So it’s like if people get to do the fast pass, skip that line,

and just say, yeah, I’ll take that home that is perfectly manicured, done, and leased out and managed. Why wouldn’t you? To me it’s a no brainer, but again there’s also people like myself who, if I was told that when I was twenty, would have said forget it, I could do that myself. So it just depends on what phase of life you’re in or how you think about it.

Right. And that’s one of the things I love about real estate investing, there is a seat and an option within it for everybody. If you’re that twenty year old who only has a few bucks to your name and you have to bootstrap it, then fine, put in that manual labor, do that flip or that burr yourself. And yet for other people whose time is worth more, there are other options, like these turnkeys you’re offering.

It’s so true. Yes, there does come a point where you realize you’d rather pay someone who’s really good at it, to do this without having to go through all that headache and hassle of figuring it out yourself. Totally agree.

I’ve done a few flips and burrs, value add renovations in our portfolio, and I swear, every one gives you a few gray hairs. It’s super stressful. That’s part of why we moved to the private lending seat on the bus, because I did not have any special gift or skill for value add. That was not my zone of genius. So it’s like, let’s move to a different aspect of real estate investing that works for us.

You guys have skipped the line. I’ve always said there’s a progression in real estate where it starts with the bootstrap, you do a flip or a burr, and do that a handful of times. Some people do it longer than others, but they stay in that lane for a long time, then they get burned out, and then they figure out, why don’t I be the bank? Because the bank never loses. They always make the money no matter what, and they get paid first while I get paid last.

Some of us learn that later than others. I’m glad you’re quick students of the game, you realized quickly, let’s just skip the line and go straight to the lending, because that’s where everyone wants to end up, being that person lending the money, saying, good luck, go have fun, and then if you default, great, I just got a property. So you’re smart to be in that position.

I’m glad we make it look easy, it’s been an adventure but it’s worked well for us. Now I do want to get into something. If we’re talking about trust, that’s one of the challenges with real estate investing. A lot of people do it long distance, which I love, I don’t think you need to invest in your own backyard. And yet it’s really important to trust your team when

you can’t just drive by the house or anything like that. So let’s dive into that a little. I know you work with a lot of long distance investors too. What would your wisdom be for them on how to vet operators, long distance?

Okay, so that’s my number one point with investors. These properties we’re selling, they’re replaceable. They’re more or less the same, give or take a few things depending on what you’re looking for. The properties themselves are replaceable. The operator, on the other hand, will make or break your experience. If you start with a property in mind first and then you’re figuring out

who the contractor is if you’re doing it yourself, and then figuring out who the property manager is, because you’re doing remote things, you’re doing it backwards. I did the same thing. Everything I talk about is learned experience, all done the hard way. I’ve never had the intuition to think, maybe I should do this so I don’t have to go through that. I have to go through every single brick wall myself. So yes, I’ve been an investor,

turnkey in Alabama and Michigan, and I have lots of horror stories that go with that. But really it came down to the operator, because I trusted too much. What I tell people, and this is a big deal for us, is I understand where out of state investors are coming from. It’s scary to invest in something you don’t know, you don’t know the area, the cities aren’t familiar, so you get scared about it.

There’s definitely an element of trust, and I always encourage people to do this, I’m okay with you flying out here and looking at the properties, touch, feel, make sure you like the areas and drive it. That’s important. But more important, you have to meet with the operator. I had a mentor of mine who does turnkey real estate in Kansas City, and I watched him

interview a property management company. This was when he first came out here with me and we were thinking about doing this together. I was thinking about being a partner with him, and he’d done it before, so he was showing me the ropes. He went to this management company and took basically an hour of their time. He sat them down and asked them

so many good questions that I thought, whoa, this is almost uncomfortable for me, it was like an FBI interrogation. But he did such a good job that by the end of it he said, that person knows what they’re talking about, this person is full of it. And he was right, he was dead on.

And honestly, by the end of it he said, I don’t think any of these make sense, I wouldn’t trust any of them with my money and my capital. That’s when we realized we needed to start our own property management company, because they just didn’t meet what we needed, our standards. We had high standards, and it’s important to have high standards.

That was a big lesson for me, because in the past I would think, he seems like a nice guy, we had a five minute conversation, I feel good, yeah, go ahead. And you’d think, why would you trust someone with a three hundred thousand dollar asset to do whatever they want with it? So there were a lot of lessons in there.

Right. And I remember hearing that your goal was originally to do the house renovation, and you started doing the property management because you knew your clients who were buying your finished houses, your turnkey properties, needed property management. You couldn’t find what you wanted locally, so you made it.

Yeah, anyone who’s been in real estate and dealt with property management companies, and you’ve obviously dealt with us too, so I know we have our challenges and weaknesses, and nobody knows those probably better than me. But you also have to be self aware as a business owner and know that’s a problem you probably need to look into. It just came down to having those high standards, and

for me, I tried it. I actually gave a couple management companies a few of my properties just to see how they would do, and I was amazed at how low the bar really is. They didn’t even do the basics, like answer a call every once in a while, or an email, just let me know if it’s going okay. If I have to fly out there to see what’s going on, that’s probably a bad thing. So it was a rough experience. And

the other thing that surprised me was, everywhere you go is a little bit different. You’ve been all over the world, so you see culture is a real thing. In the South, what I realized was it’s a copycat, everyone does it just because that’s how it is and that’s how everyone does it. I’d say, well, why do you do that, and they’d say, well, I don’t know, it’s just how it’s done.

So I’d say, why don’t you try this model, and they’d say, because it’s just not the way we do things. That doesn’t make sense. There was, for example, an eight percent or ten percent management fee, every single company across all of Chattanooga is eight or ten percent. Nobody does a flat fee? Really? That hasn’t dawned on anyone? So I thought, okay, well, it’s not unique, anyone could do it, but

for whatever reason they didn’t, and I know why, there’s a lot more money in the percentage model. But I hate the percentage model because it’s backwards. We prefer three thousand dollar rentals over thousand dollar rentals. Why does it pay me three hundred dollars over here or a hundred dollars for a hundred thousand dollar house, or a thousand dollar rental, that doesn’t make

sense, because it’s actually more work to do the lower income properties, so it’s inverted, and that’s always driven me crazy. So that was just an example of, I think we can do better. So we did it.

Yeah, and I agree a hundred percent. I have a family member who just bought in Tuscaloosa, Alabama, a student housing property, a duplex or triplex, and

this family member is upset when she visits because that management company is getting thousands of dollars a month, since it’s a student rental, they’re renting by the room, multiple doors. She says, what are they doing for that? And I don’t think they’re doing much. That’s something with the percentage based model, when you’re getting over a thousand dollars for one property with multiple doors, you have a pretty high bar your client is going to expect of you in terms of

the value you’re adding there.

Totally, a hundred percent. With us it’s like we treat everyone the same. It’s a hundred bucks or eighty five dollars for multifamily per door. That’s just how it is, transparent.

It makes it a whole lot easier to say yes to that from an investor standpoint. So now, one thing we talked about a little before the call, BJ, I’d love for you to share the recent pivot you had in the business.

Yeah, there are certain things that keep me up at night, and really what it comes down to as a business owner is anytime you have capital exposure

and uncertainty, that keeps you up. I’ve never really had anxiety until, I’d say, since 2022 happened. Now I struggle sometimes to sleep and stay asleep because my mind is always racing. When you take a minute to isolate what’s causing those issues, for me it came down to, right now the model was I was doing everything myself. I was finding

properties, putting my capital into it, using my guys to fix it up, and then everything was on our shoulders, hoping it would sell. It’s funny because we went three or four weeks without a contract with an investor buying one of our properties. I thought, I have seven properties right now I need to unload, nobody’s biting, what’s going on, you stress. And then, funny enough, the week later

this flood of interest came in, and now we’re two or three deep on each property with backup offers on everything, and they’re all sold out. Now I’ve got a different problem, I need to go find more properties and inventory because I stopped since I was nervous, and clearly that’s a bottleneck. So what we ended up doing was realizing, okay, we’re going to go to a model where

we work with the investor at the beginning, on the front end, and say, okay, what are your goals, where do you want to be, do you want multifamily, single family, Tennessee, Georgia, what do you want, and then say, okay, if I find that property, I’m going to present it to you, and if everything looks good with the budget we have in mind and the rental rate, we’re going to do this together. So they reserve the property on the front end, and then we went from

basically having an inventory of homes and hoping someone would buy it, kind of like the MLS flip model where you flip homes and try to find a buyer later down the road, to now having a built in buyer, an investor already committed, putting capital up front to buy that property.

So there’s a little bit of skin in the game, they’re a little more committed, but it’s fun for them to see beginning to end, they’re part of that journey. It reduces the number of days I need to sit on a property, because that eats up capital, since I’m paying people like you. So it definitely answered a lot of those questions for us. But I did feel I couldn’t just jump into that model right off the bat, because in my opinion, I wanted to prove myself,

that there is demand, that this is the right path, that there’s a viable business here. So we did a hundred properties basically with this first model, and they all sold out, they’re all doing great for the most part, it really has come true, what our vision was. Now it’s, okay, we need to step it up, reduce our risk, and hopefully get to a point where I’m not the one responsible for all this capital out there, and eventually get to a point where I’m the investor, like you, lending to people, and getting into that phase. So that’s the direction, this is step one towards that direction.

I love this from an investor standpoint, because I think of all the times you go into a house and think, I wish they had cheaped out on this or overspent on this, which isn’t important, and you wish you could go back in time with them and redo those choices. That’s what you’re effectively having investors do.

Yeah, it definitely is.

What I love from an investor standpoint of what you’re doing, BJ, is I can think of all the times I’ve gone into a house or a property and thought they either cut corners or overspent on certain areas, and it makes me sad when I might have to redo something that’s already brand new, because I’m originally from California, I don’t like waste, I’m very environmentally friendly, or when they overspent on something that isn’t going to increase rents, so it makes the numbers not work.

And you let people avoid all of that with your model.

Yeah, and you know, this is where the experience comes in. I used to be all about the Instagram look, the cool finishes, that was the exciting part. Now I could care less about the finishes, because I’ve realized you have to understand the market you’re in. Maybe that would matter in Arizona or California, but when you’re in Chattanooga, good enough is good enough. They will not pay you, they will not reward you for nicer finishes. They won’t. And

it’s because everyone’s on a budget, it’s just the reality of where we’re at. People are living on a budget. Knowing that, I know my renters, there’s a cap on what they’ll pay for rent, and I’m not optimistic about rent anymore, I’m pessimistic about rent prices. So we pretty much always hit them within about a hundred dollars every time. That’s only because I’ve learned. But the other thing I’ve learned is investors,

everyone always says, well, rental properties don’t cash flow anymore, long term rentals don’t work anymore, because that’s the new thing, real estate doesn’t work anymore, and that tells me this is a fantastic time to buy. Do the Warren Buffett thing, when everyone is fearful, be greedy, and when they’re greedy be fearful. So this is absolutely a fantastic time right now, we’re having a heyday, because now I can buy stuff for whatever price I tell, because who else are you going to go to? So it’s fun right now in that regard.

But getting back to the point of finishes, what I focus on, and the reason people say they don’t make money on rentals, is because they’ll say, well, I had to repair my AC unit and that was six thousand dollars, or I had to do a new roof and that was ten thousand dollars.

So I start with all the CapEx expenses, and I always say, start with all we care about in the beginning, MEPs, mechanical, electrical, plumbing. I look at the foundation, we do the sewer scopes, I know where all the traps are. I’m flushing out every one of those at the beginning. I want to do a pre-inspection, tell me all the bad stuff. If it’s knob and tube wiring, we’re doing all new electrical on the whole house. We’re doing all new plumbing, all new flex.

Pipe like this, these are all things I know will come back and bite you. Yes, you’ll make money in the first couple years, and then you’ll have to do all these repairs. So with us, our whole selling point is we’re going to do a new AC pretty much all the time, new AC, new roof, new electrical, new plumbing. And then you get to see

on the front end, a lot of times people will say, you’re making all this money, and it’s actually, no, on that one I lost money or I made a hundred dollars. There’s been times where there’s a spread of a hundred thousand dollars and you’d think you probably made a lot of money, but no, I spent it all on the big stuff, so now there’s no money left. That’s another reason I’m kind of tired of being the very last person to eat.

When you’re a flipper, just know that’s the reality, you get what’s left over. If you’re not protecting yourself on the front end, you obviously make money when you buy, and those are things you learn, you can’t make up for it after you’ve already purchased it. You’re pretty much set once the concrete starts to form. So those are all things where I think, let’s bring an investor in, he can see where all the money is going, and

then realize there’s some margin in there, obviously we have to stay in business, but it’s not fifty thousand dollars. And by the way, with this model, if we just had one recently that appraised for four hundred thousand and we sold it for three hundred sixty, I could look at it two ways. I could look at that as leaving money on the table, or

the way I look at it is, this investor just had forty thousand dollars of equity day one and didn’t have to do a thing. He got an investment property where he’s putting twenty five percent down, he’s already going to make a fifty percent return on that, plus all the rental income and tax benefits. It really is a cool model in that regard, because they get to enjoy equity and cash flow. So we’re willing to take on a lot of the brunt of

the chaos that goes with fixing up.

So there are two things I love about what you shared here. First, as somebody who’s replaced four HVACs this summer on rental properties, from a finance perspective, when you’re doing it after the fact, it just comes out of your income for that year, versus if you can do it during the renovation like you’re doing, then you’ve paid for it with your renovation loan and you just have the mortgage after.

That’s so much better from a managing your cash and expenses standpoint. I love that. And the second thing is, it’s great that somebody could have you help with all this, have everything, and sell it for three hundred sixty and get that equity, that’s really the goal of doing this. I love that, because people worry, there’s a scarcity mindset of, if I have somebody help me with this, then I’m not going to make any money. It’s great that you give an example where people can do this,

they can have your help and still make money. My favorite is where everybody in the party is winning, and that’s what you’re working to set up.

Yes. Everyone’s got to eat, everyone’s got to win. If you do that, you realize as a business owner, I don’t need to hit a home run, I need to hit a single or a double. And then they come back to you and say, you treated me fairly, we did good together, let’s do it again, and that’s where the magic happens. It’s the repeats, you don’t have to spend money on marketing to find other people.

So my goal is to get to a point where I have ten or twelve investors where we’re basically a private advisor kind of thing for those individuals, so they can enjoy being in the market without having to be in the market.

I love that, and I feel like it almost becomes a who-you-know thing, you’re only going to take on clients when they’re referred by another great client, and it’s very exclusive. I’d love for investors listening to think about what must be true or different about a business like that, versus one that’s having to spend tens of thousands of dollars to sponsor a conference multiple times a year. There’s going to be some pretty huge structural differences in those two businesses.

Totally, we don’t spend any money on marketing. That’s just because, from the beginning, I felt it should be referral based, word of mouth, and it’s worked out that way. There have been some sleepless nights wondering if I should have done a lot more marketing to find these investors, but fortunately it’s worked out.

Well, BJ, this has been a longer episode than normal because it’s been so fabulous. I’m really excited about everybody who’s going to listen and get some takeaways from this. If people would like to learn more about Property Rush or connect with you, what’s the best way for them to do so?

Our website is propertyrush.com, and it has everything you need on there. You can set up a thirty minute call with me if you’d like to discuss and see if we’re a good fit. And then Instagram, I’m on there as well as Facebook, and thankfully I have a weird last name, so there’s not many BJ Gremillions, I think I’m one of one, as far as I know, maybe there’s another one out there, but I’m pretty easy to find because of the last name.

I love that. I know for a large part of my upbringing I wished I had some normal name like Rachel or Heather, but now as an adult, similarly, I’m glad I have a name that’s not as common.

Totally, people remember it. And funny story, our property manager, believe it or not, is also BJ. I’ve never met another BJ out here, but it just so happened that the one I did find is our property manager.

That’s fun. Well, for our listeners, thank you for listening. Please reach out to BJ if you’re interested in this turnkey relationship and being one of his VIP clients. And thank you for listening to another episode. Join me again next week for another amazing conversation.

Thanks again.

The post He Was Carrying All the Risk on Every Flip, Then He Changed the Model appeared first on Adrienne Green.

If you have ever felt like your business runs on leads that go nowhere, you are not alone. In this episode, I sit down with Sheldon Wolf, a founder, investor, and operator with over 35 years of experience across real estate, finance, and technology. Sheldon built Intellitary, an AI-powered platform he calls the “Un-Brokerage,” designed to pre-qualify buyers and sellers before they ever reach an agent. We get into why most lead generation is a waste of money, what it really takes to build a business that survives the next market shift, and what he believes the real estate transaction will look like five years from now. If you are ready to rethink how customers find you, this conversation 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!

Hello and welcome. I’m Adrienne Green, and here we talk about how, as a real estate entrepreneur, you can get out of the grind and start getting the freedom that you really got into real estate for in the first place. And to speak to that, today I have with me Sheldon Wolf. Sheldon, thank you for joining me.

Thanks for having me. It should be a lot of fun.

So Sheldon, my understanding is you’ve spent over thirty-five years as a founder, investor, and operator across real estate, finance, and technology, all things I love. So for our listeners who are just meeting you, what does your world look like today?

Insanity, of course. I would have it no other way. I thrive on chaos. To me, a lot of people, business is business, it’s their job, it’s what they do. To me it’s a sport. You step into the ring each and every day and you slay the dragons. That’s what it comes down to. I’ve been doing it since nineteen eighty nine, and you can be sure I’ve seen enough ups and downs and all arounds and all that crazy stuff, good times, bad times. The one thing I speak to a lot is the fact that I actually tend to thrive when things are crappy. So the worse things get, the better I get. It’s that athlete mentality where you step in the ring and you know you’ve got a tough fight, you’re gonna fight that much harder. And that’s exactly how it works.

What I’m hearing here that I love is an abundance mindset, right? We’re gonna, like you said, slay those dragons. This is gonna be fun because we’ve gotta do it one way or the other. We can either be complaining about it or we can have a positive attitude and be like, these are wonderful problems I get to solve. I love that.

Well, it is a lot of fun to me. I would not see myself doing anything else. Everyone always says, Sheldon, why don’t you just sell off your properties, retire, like what are you doing? How much money do you need? This isn’t a money thing. It doesn’t matter what I’m working at. It’s a play to win thing. It’s beat your own record. It’s not about I have to beat someone else’s record. I don’t need to be bigger than this guy or that guy. I need to do better than what I did last year, or that one year, five years ago, or whatever I built I can do better, or what if I did what I did but I made it do this and this. It’s that kind of mentality. It’s like going into a game where you know you already win.

And I bet every real estate investor listening can relate to that. We all have somebody in our lives who tells us exactly what you just said. Why are you still doing this? Why do you have the hassle? Why are you dealing with these tenants? Why are you dealing with that busted pipe or whatever happens, right? When the truth is, like you said, it’s about being one step better than I was yesterday. So tell me a little bit about your current fun game of Intellitary.

Intellitary’s juicy, and I’ll tell you what makes it really interesting. I’ve worked from the investor point of view. I’m an investor and I’m an entrepreneur, founder, all those fun words. But I built Intellitary backwards. My blueprint starts at the end. This is something that people who are highly successful would understand. But if you’re both the founder and the investor, you pretty much map it out. I’m well beyond the wall. There’s gonna be a wall that’s gonna blow in, and whether it’s in two years, three years, five years, this goes right through the wall. So I’m past that. We start with the profit and all those things that people don’t like to talk about. They like to talk about the revenue but they never like to talk about the profit, because usually there is no profit after the cost of acquisition, all those other fun things. So this works itself backwards, but what it actually is,

Okay. Yes.

It’s nineteen eighty nine, nineteen ninety-two, nineteen ninety-five, all those illustrious years of old school hand-to-hand combat real estate transactions, and I’ve put together thousands, very few people put thousands of transactions together. I put thousands of transactions together. This is everything I’ve done, my entire legacy, turned into an AI orchestration layer that follows the same monetization system I’ve used for thousands of transactions over three decades. The easiest way to explain what Intellitary is, it’s a customer orchestration layer that’s very customer centric. What that means is, where the world is built of brokerages, and I’m assuming you have quite a few real estate listeners and maybe some brokerage listeners and a lot of investors, typically the brokerage recruits realtors.

The more realtors,

it follows a formula. If you’re a brokerage and you have 10,000 realtors, you factor in the math and say, the average realtors all put together equal this many transactions per year, which equals that. So they’re on this big march to recruit as many agents as possible, on an all-time basis. That is their agenda. And now you see this kind of march where they’re buying old legacy brokerages. You see the sale of RE/MAX, you see the sale of Fathom and all these other companies being

Yeah.

bought by bigger companies with more firepower. And then what you see is me, I call it an Un-Brokerage. I’m building something the opposite way. I’m not interested in having the realtors. The realtors are there, we’re going to cooperate with them. We have programs that we’re building out for the brokerages, but we’re interested in orchestrating and originating customers, because our view of the future of real estate is whoever controls the customer controls the real estate world. If you’re a brokerage or a realtor and you don’t have customers, well, I’m sure anyone can tell me what that looks like. That’s where the revenue comes from. That’s where the profit and all the wheels start turning, is when you have the customers. No customer, no business. Very simple. So we built it backwards. The easiest way to explain what I built is Best Western Hotels, which everybody knows, but what they are, they don’t always own the hotel. They’re an orchestration layer and their only purpose is to take the customer we speak about and drop them off at the check-in desk at a hotel in any city in almost any part of the United States and Canada. That is their goal and that is their purpose, and they’ve done their job when they’ve got their traveler at the check-in desk. We do the same thing with real estate. We take a pre-screened, pre-qualified customer who wants to buy, sell, get a mortgage, all those fun things on the monetization path I’ve invented, and deliver them into your front seat or to the front door of the house they want to see, or to the brokerage where they’re gonna assign a transaction. I’ve essentially built something where, if you’re a brokerage, you’re just gonna get an extra fifty thousand transactions, and then the next step is, if you’re going to originate fifty thousand transactions this year and hand them to this brokerage so their realtors can harvest the results of that, well, the fact of the matter is that fifty thousand transactions are fifty thousand transactions not going to their competition. And that’s essentially what I’ve built.

I appreciate a lot of what you shared there. As a licensed real estate agent who was active for a period of years, I can attest what you’re saying about those brokerages is exactly how they do it. They focus on, let’s recruit agents, let’s recruit agents, and then the agents are gonna go hunt, because it doesn’t really cost them much to have those agents, right? But the brokerages don’t really worry about customer acquisition. They do what they can, but they figure it’s the agents’ jobs mostly. So of course

Yeah, exactly.

the next logical question to me is, how is Intellitary getting all of these high-quality clients?

Well, the fact of the matter is, we use AI technology that, let me put it this way, was personally designed. I’ve been very, very involved right from square one. I developed it, designed it around my own success. So when I say this thing goes back to my roots, there’s a reason why I’ve put together thousands of transactions. There’s a reason why the average realtor literally only does two to three transactions per year. That’s the average. That means nothing when you think about it, because there are realtors out there who do six deals a month, five deals a month, even some twelve, ten, all over the map. But then there’s a lot of realtors who just do very little. They coast. And it’s not that they don’t know the industry, obviously they’re in the industry. Their biggest problem is customer acquisition. So if you’re a brokerage on that side of it, you have a whole bunch of agents in your office that are not really providing revenue. They’re there, and maybe you’re getting a hundred dollars a month as a monthly fee, and then maybe when they sell something, if they sell something, you get a percentage of their commission. But that’s not enough, because when I read financials, and trust me when I tell you I read everybody’s financials, if they’re out there and they’re publicly traded, I’ve read your financials and I know your flaws. There’s some companies out there where the realtor gets a deal and the brokerage only gets two hundred and seventy-five dollars off the commission and literally a hundred dollars a month. There’s some that take zero transaction fees per month. So when you read

their financials, it’s nothing but red ink all the way down, and they’re bragging, look at our revenue. But look at that column next to it, which has got red ink on it. Your system’s not working. But we have 25,000 agents. That means nothing. I’d rather have a hundred agents and be a brokerage making millions of dollars than a brokerage losing hundreds of millions of dollars every quarter with 25,000 agents. To me, it’s not about how many agents, it’s about the transactions. Transactions are where the revenue hits the door of your office, and that’s what I’ve built. You worry about recruiting, do what you guys do best. I’ll worry about how the customers are going to be delivered to you. So I built a system, a delivery system, and it’s actually ironic because it operates and functions kind of the same way Uber does. So a customer, Joe Smith, who is pre-approved, who’s already sold his home, wants to view 123 Cherry Tree Lane. It literally pops up and gets dispatched the same way. He wants to see it at three o’clock. This realtor’s available, that realtor is available, and whoever picks it is meeting this customer, and they already know who, what, when, where, why, and how. They know everything they need to know, and the meeting’s booked. The second thing it does is it transfers the customer

in real time. It’s all fully functional. You go to the website and you’re gonna have a conversation with Chloe AI. Chloe AI, much better looking than me, I will say, but you’re gonna have a conversation as fluid as the conversation you and I are having right here, right now, with somebody who looks as real as I do, but better. She’s gonna get you to sign up, which is literally give me your name, number, and email. And as soon as you do, she’s gonna then call you and say, hey, it’s me, Chloe, I was just chatting with you on Intellitary. But now that she’s got you on your phone, she’s able to sign documents with you, hot transfer your call directly to someone in that area right now who can set up that showing for you. It’s all fluid, it doesn’t break. It literally runs down a

perfect real estate track right to the brokerage door. That’s essentially what it’s doing. It’s designed to handle customers the same way this guy would. So as good a software guy as I am, as good an AI tech as I am, and as well as I completely understand the integrations, I’m also the guy who’s done thousands of transactions. I see a lot of companies that are built by a great software guy, but he doesn’t know the industry. So when you see, well, why did it fail? They got to a billion dollars and then they crashed. Nobody understood the industry. So I bring both, I bring the best of both worlds, the tech and the industry, to the table.

So what I’m hearing about Intellitary is it’s a new take on a model that’s been around for a while in terms of helping with that lead generation, right? Helping bring that ready, willing, and able buyer or client to an operator’s doorstep. We see that in the real estate agent space. We also see a lot of companies trying to do it in the real estate investing space, because that lead generation is tough. So we love when there’s a good company working to fill that gap. Now here’s my question, Sheldon, for our listeners who are these real estate entrepreneurs. Intellitary, you know, you’re not the only one out there helping do that lead generation. What are the top questions an entrepreneur or operator should look at when they’re vetting a company like Intellitary, somebody who promises to bring them a beautiful client right to their doorstep?

Okay, so here’s the difference, because I’ve been in this game a long time, and I’ve seen lead gen come up, I’ve seen how they get their leads, how they process their leads, who gets their leads, how many people get the same lead. I’ve seen it all. It’s the oldest rodeo in town. So I decided I’m not interested in producing leads. I want to produce actual bona fide customers, where instead of just getting a name like most realtors, or even in the investment side of things, you’re getting a guy’s name, his phone number, and his email. And whether he applied right here, right now, three hours ago, or three days ago, the bottom line is, what you’re actually buying right out of the top is a 50-50, because 50% of all leads, you’ll never actually

get in touch with the customer. I don’t want to produce that. I want to produce something transaction-ready. Something where a clone of me, who would handle a lead as good as I would, is actually discussing and getting the commitment, getting the loyalty, finding out all those questions realtors are too embarrassed to ask, like, hey, have you been pre-approved? Tell me a bit about your income, all that stuff. And

all those fun things. I ask, how soon are you looking?

Very simple question, but guess what? It’s not what you think. It’s how motivated are you, and it’s how you answer the question. I’ve built in what I call heat scoring. So every answer is a score in a matrix I’ve built, and that’s going to determine how serious this customer is. I do not want any of my agents running around with a guy who’s bankrupt who can’t buy but says he wants to buy, or just wants to look at properties. We’ve pre-screened everything, it’s vetted.

A guy who says, no, I’m actually very serious, I do want to see 123 Cherry Tree Lane, it’s the perfect house for me, have one of your guys meet me there, and then it gets dispatched, very simple. Or, yes, I do want to sell my property, I’m looking for this, here’s my house, here’s all the details on my house, and then that gets sent out to three of our agents to do a proposal on it,

an evaluation, and what the best commissions are that you’re gonna offer this customer. So it’s all real customers, we’re not interested in leads. I’ve been in that game before, a long time, and you’re buying mostly garbage. The true statistics, and you can ask any realtor out there, they’ll tell you the same thing. Number one, you’re only going to talk to 50%, if that, of the people you’ve actually paid to speak with. From there, you monetize at about two to three percent. So what does that mean? You have to go through a hundred leads to really get a couple that are even potentially where you’re gonna see some revenue. Now, does it all make sense in the end? It makes sense, because if you do a deal and it’s a big enough deal, your commission’s gonna be worth it and it all makes sense, but it’s a hell of a lot of work just to get one customer to transact. Where we’ve eliminated all the fluff and garbage, this is as if I took the call myself. In fact, better. And I’ll tell you why it’s better: Chloe on Intellitary can handle 20,000 phone calls at once. 20,000 unique calls. Me at my best, no matter how good I am, I can take one call. I’m doing your podcast, I’m not on 20 other podcasts, I’m not on 20,000 other podcasts. I’m here right now. That’s my limit. Chloe can talk to 20,000. So that’s what she does.

And how can a business operator who’s vetting companies like yours differentiate between that level of closure rate you’re offering versus other competitors or other options they might have?

Well, there’s no, I look at everything I build and I don’t believe there’s that kind of competition. And I’m the guy that, when I step into the ring, if somebody says, hey, I can build that out, I can do this, I’ve seen a lot of software guys come and go if they don’t understand the industry. If you’re not a guy who understands what it’s like to put thousands of transactions together, I mean, I built a funnel back in the day, I never actually left my desk. So I may have sold more real estate than anyone else, but I never actually left my desk. I built thousands of properties, and almost every property I sold wasn’t even built at the time. These were invisible homes, all sold off blueprint. So if you can build that kind of machine, where you’re selling real estate without showing houses, without going through property, without going through all these different processes, but it was a lean machine where a customer would be at my desk, they’d already be pre-approved, I’d know everything about them, and my entire day was spent writing transactions. That’s what I’ve reinvented with

Intellitary. And really, I don’t believe there’s anything. There are a lot of lead companies out there, you can buy real estate leads all over the place. But the fact is, I talk to realtors every single day, I talk to brokerages every day, and they’ll all tell you the same thing: yeah, I’ve spent six thousand dollars on these, I got zero in return. If you don’t have that rate of return, then it’s a complete waste. Advertising, same thing. You could spend five, six thousand dollars on advertising and get nothing but garbage calls and nothing that turns into anything. This is taking all the fluff out of the game, so you’re not buying a whole bunch of names and phone numbers, so to speak.

Well, and one thing you mentioned in your answer there, Sheldon, was the idea of using a system, right? And that you built a system you’re replicating here with Intellitary. So let’s talk about systems, and part of that is the delegation, right? When somebody’s working with a company like Intellitary, they’re really handing off some of the work they would do to a technology, to another customer. Now, you’ve spent your career thinking about systems, software, so that we are not

manually doing all the work ourselves. Like you said, you can only take one call. Usually that starts with mindset. What would you recommend to listeners who are struggling with the idea of going from solopreneur, DIY, I do it all, to let’s leverage systems, let’s leverage technology? What would you say needs to happen with their mindset? What’s your wisdom?

Well, the thing about it is scaling and growth is the most important thing. If you don’t harness that, you’re going to be at a standstill. It’s so important that you have that vision. One of the things I said a little while back is I build things backwards. I start at the goal, and I work it backwards, and I’ve factored in all the good times, bad times, and all the fun things that are gonna come along the way, the triumphs and tribulations. I’ve factored in the fact that there’s going to potentially be a wall. There’s a company out there, a massive company, billion dollar company, but they didn’t

factor in the wall, and they’re a very volatile company because they’re affected by things like interest rates. Something as simple as interest rates freezes the market. Meanwhile these guys acquisitioned a whole bunch of properties, but the properties were acquisitioned six months ago, five months ago, seven months ago, and now they all come to fruition today. How you bought the houses then

is not gonna stand well today. So things like that have to be taken into consideration. Things like the volatility, things like walls coming up, whatever you’re doing has to be designed to be beyond the wall. So, you know what I always say, in a cyclone, even a turkey will fly. When times are good, everybody’s making money, everyone’s driving around in their nice BMW and Mercedes. When times go bad,

my apologies. When times are not so good, all of a sudden that smile comes off the face real quick, and that’s where you have to be able to fight and understand that there’s ways around things. So whenever you’re building a system, embrace technology. I hear so many agents say, this AI thing, instead of celebrating and saying, how do we use it to our advantage,

Mm-hmm.

they’re complaining about it. It’s taking people’s jobs, I hate this AI. No, you hate it because you don’t want to spend any time engaging it or learning it or understanding it. Instead, you need to embrace it. If you do not embrace technology, you’re gonna get run over by technology, because if you’re not using it, your competition is. So I speak to brokerages every day and they’re saying, well, we just upgraded our system five years ago. Well, five years ago in technology land, your five year old phone probably doesn’t even work anymore. It’s on 2G or 3G, and everything becomes obsolete. That’s why I built Intellitary. It’s meant to go and punch

through that invisible wall that comes our way, whether it be a dot-com bubble, an AI bubble, or this bubble or that, there’s always another bubble. Anyone who doesn’t believe that hasn’t been around as long as I have. I’ve been through many bubbles. It’s designed to do that. If you’re trying to solve today’s problem, that’s a problem, because today’s problem is already solved by 5 p.m. By tomorrow it’s been copied, and by next week it’s obsolete. So anybody who’s saying, but I just changed my software five years ago, three years ago, we just bought today’s today, tomorrow’s tomorrow, and we need to focus on tomorrow, next year, five years. Because five years will come, and it comes sooner than you expect. You don’t want to be caught empty with no good new technology. Good technology today, doing what I did in 1989, wouldn’t work today. Doing what I did in 1995, that wouldn’t work today. Doing what I did in 2000 wouldn’t work today. As good as I am at meeting a customer hand to hand, putting a deal together, that part works. But

how I’m getting that customer, how I’m acquisitioning the customer, how I handle the customer, how the entire monetization system works, that you have to stay in touch with, because that will change.

And you’ve mentioned on several of your answers here about a wall. Can you dive into that? What is the wall for the real estate industry that you’re seeing in the near term?

Let me put my investor hat back on here. The fact of the matter is, everybody, unless you’ve been hiding under a rock somewhere, can see what I see, and I see affordability being a problem. I bought my first property when I was in my very early twenties, maybe twenty, twenty-one. It wasn’t a problem because properties were a hundred thousand dollars back then, where that same starter-like home today is pretty much starting at half a million dollars. A million dollars doesn’t even take you that far. It gets you a decent house, a nice house, but it doesn’t get you that big sprawling million dollar mansion of yesteryear. So the fact of the matter is, people these days aren’t buying their homes until they’re in their 30s. The next generation is gonna wish they could buy their home in their 30s, but 30 becomes 40. It’s this evolution of affordability, and I see it becoming something unless somebody is smart enough to figure out how to make

a property affordable. The house doesn’t need to be built cheaper. There just needs to be better ways to buy real estate. That’s always been my strong point. So when the rates went up, I did buy downs. Everyone else had an eight percent interest rate, I had a five percent interest rate. Whatever we were able to legally push and buy down and promote, that’s what we did. We found ways to work with down payments. We found ways to stretch it out. I had the luxury of spending a lot of time in the building and development industry, so I was able to

stall out payments while the home was under construction. I was able to do investor deals so by the time the guy’s house was built, he’s already making forty, fifty thousand dollars and he hadn’t even moved in yet. There’s always a strategy to get past the wall. You just have to know what this wall coming up is. I think real estate,

most people naturally think, well, what about these mini homes, we’ll just build smaller homes, cheaper homes. That’s partially right, but that’s not gonna solve it, because someone still wants to buy a home. People still want that so-called American dream. So I think it’s a matter of creative programs. It’s not really the hardware, the hardware’s your house, it’s the software. It’s how you’re going to make that transaction happen. That’s always been my strategy, because at the end of the day, drywall is drywall, lumber is lumber, roofing is roofing, concrete’s concrete. All those things have elevated, and all those things go up with the cost of living. So how do you fix that? The cost of labor goes up because the cost of living goes up and people need to pay more. So you need to deal with the software end of it. If the program is the software,

the hardware is the home, that’s what you need to deal with. It’s always on the other side, but people don’t automatically think that. They think, well, there’s gotta be a way to build the house cheaper. You don’t need the house to be cheaper, you just need to make it so that this guy can afford to pay. Usually it’s a matter of, he’s gotta pay to live somewhere, he’s gonna pay rent. How do you make it so the mortgage payment smells more like that? Because people at the end of the day don’t really care how much they paid for the house. They care, can I afford to live in this house? That’s really the truth of it. And that goes to all the investors out there.

That’s a lot of good points there. Now with AI and everything that’s happening on the forefront, I’m curious what you envision the day to day role of a real estate agent looking like, let’s say five years from now.

The AI will be completely, so to really answer your question, I’m gonna answer it backwards. It’s not about the agent. The agent will have AI, or they’ll simply not be in the business, or they’ll be one of those agents we talk about that does maybe a deal a year because their friend just bought a house from them, or a friend of a friend just bought a house from them. So let’s talk about the customer, which is the reason I built Intellitary.

It’s the customer that behaves differently today. The realtor doesn’t behave differently. Their goal is to find a customer, show a home, sell a home, or list their home and sell their home and then sell another home. That part’s exactly the same. How you’re communicating and where you’re getting the customer is a little different. But at the end of the day, we have a smarter customer. The customer is the same customer, but they’re smarter only because the technology allows them

to have access to better information faster. So I’m a home buyer and I’ve got a phone in my hand now which has AI on it. So I need the realtor less and less because I could already find out where the schools are by asking a simple question. I can already figure out the crime rate. I can already tell that I can’t afford to live in that area because it already knows

my budget, it already knows my debt ratio, it knows all that stuff. It already told me how much I can afford, how much I’m gonna qualify for with my income and my debts. So the customer who knew nothing about real estate two years ago

all of a sudden knows everything, and they’re a genius. Whether the information is 100% accurate or correct is a whole different story. There’s a lot of misled customers out there, but they transact differently. Where are we in five years from now? You’re gonna have a customer that will be able to do a beginning to end transaction. To me, everything is just data and field mapping. So you’ll have a customer that will be able to press a button and make an offer, all that fun stuff. Do I think there’s a need for realtors and brokerages? Absolutely. I’m a preservationist. As great as I love my technology, I’m using the technology to preserve the industry. Do I think a customer will be able to just write an offer, press buttons, add in whatever conditions are recommended for their situation? Yeah, I do.

Do I think that will be the same for the law industry? Yeah. But do I think people should be their own lawyers? Not necessarily, depending on your situation. But there’s a lot of liability, and real estate is one of the most expensive investments or assets you’re going to obtain during your lifetime, whether you have one property or an armada of a hundred properties, it’s still the biggest,

most expensive investment you’re going to jump into. Do I think that having a human is always good to have? Yeah. I play with AI I don’t even know how many hours a day, because I’m always developing something. But it’s not a hundred percent accurate. Do I think there’s gonna be flaws in five years from now? Yeah, of course. There’s gonna be flaws in ten years from now. There’s gonna be flaws always in everything. Everything is a double-edged sword when you’re playing with technology. Okay, I got it to do this, but now it’s struggling with that. It’s doing great with that,

but that’s right. So where do I think the realtor is gonna be in five years? It’s more like, where’s the customer gonna be in five years? How do I get B to connect with A? That’s how I look at it. How do I get this data over to this guy so he can do his job? Maybe his job is less and less. Maybe he’s just simply receiving an offer from this customer, reviewing it, and putting together conveyancing, all those fun things.

So I see it just integrated differently. But I think it’s always gonna be the same. At the end of the day, it’s a person wanting a roof over their head. So as complex as it gets, I like to bring things back down to simple.

And I think that’s a great place for us to wrap up, Sheldon, where we have this wisdom from you about technology and the human component and how they’re going to continue to work together going forward. Sheldon, if somebody would like to connect with you or learn more about Intellitary, what is the best place for them to do so?

The best way to hit me up is to email me at Sheldon, S-H-E-L-D-O-N, at Intellitary dot com. Intellitary is I-N-T-E-L-L-I-T-A-R-Y dot com. You can also find me on LinkedIn, feel free to add me, feel free to connect. Very easy to communicate with, you can ask me absolutely anything. You’re also welcome to go to my personal website, which is sheldonwolf.com.

Perfect. Well thank you so much, Sheldon. And for our listeners, thank you for joining me. Join me again next week to hear another great take on the real estate industry today.

The post How One AI Handles 20,000 Buyer Conversations at Once appeared first on Adrienne Green.

Before you dive into the full conversation below, here’s a quick preview: in this episode I sit down with Cameron Tope, who owns more than 30 rental properties himself and manages over 300 more for investors in the greater Houston area, all run remotely from San Diego. Cameron walks through the breaking point that led him to build his own property management company, the systems he uses to turn a property in 10 days instead of 30, why vacancy costs investors far more than a management fee ever will, and how operating as both an owner and an operator shaped every decision along the way. If you want a real look at how systems, KPIs, and delegation work together in a scaling operation, this is worth the watch. 

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!

Got it, here’s the full transcript in one continuous piece, start to finish:

I am Adrienne Green. We focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start, and Cameron has a lot of wisdom to share on the subject. So can we start, Cameron, with giving our listeners a quick snapshot of your world in the sense of real estate. Properties you own, what you’re doing for others, what it looks like for you today.

Today I have just over thirty properties myself personally that I own. And we manage about three hundred for investors in the greater Houston area. And I do this all a hundred percent remotely from San Diego, California.

Amazing. Love that. And my understanding is that there was a breaking point with property management that made you decide to build your own company. Can you talk to us a little bit about the pain point you had and what prompted you and how you made that decision?

When I graduated, I was a petroleum engineer, and that pretty much meant I was going to Houston, Texas. I’m originally from Ohio. And when I got down there, oil was sitting somewhere around $120 a barrel. And within six months, it went way down to $30 or $40 a barrel. Everybody’s freaking out. I’m freaking out. I’ve got $30,040,000 in student loans. How am I going to pay that back? And there were some folks who were super cool, calm, collected, some old timers.

And I picked their brains and they said, I’ve got five, ten paid off rental properties. And that started everything. So once I started buying these properties, I had probably five to ten and I was still working as an engineer for British Petroleum. And I need somebody to manage these things. It’s starting to get a little overwhelming. And I could not find anybody. So the breaking point really was, I know the meeting specifically, because I had interviewed a handful of people all over

the spectrum, from the guy driving around in a truck that has no license, “I collect rent door to door and I’ll send you a check,” all the way up to some large multi-state multi-city companies who had thousands of doors. And I scheduled a meeting with this larger company and they frankly blew me off, and that’s when I was done. I’m gonna do it myself. So I got a handyman I had been working with who helped me out and really started looking at it as:

How do I build these systems and checklists? I’d done this before with the properties I built up, but instead of just, “hurry up, get the tenant moved in, make sure everything’s good,” think about this collectively, holistically as a process, and how do I replicate this to deliver the same great move-in experience, for example.

Right.

I love that, how sometimes good enough feels like perfect, we just do our little piece. And sometimes we need to really make a system that’s replicable, that is an actual process. So looking back, what did you get right in those first few months of building Emerson that you would tell another investor to replicate?

Firstly is just getting started. As an engineer, I probably spent a year trying to analyze properties and figure out exactly what I wanted to do. What market do I want to go? Short term? Long term? What’s the strategy? But a lot of it’s just getting started. You’re not going to have everything figured out. You’re going to scrape your knees, you’re going to have some issues. I remember thinking when I was managing my own properties very early on and just had a handful, I’m never

gonna go through an eviction. I’ll make sure I screen the tenants so well that I’ll never go through an eviction. Well, you cannot outsource or eliminate every single risk. So the first thing you got to do is have some reserves, have some stuff set aside and get started. And you’ll learn so much. But

Having that financial position to be able to make investments, that’s probably one of the first things to do outside of taking the initiative, because things will go wrong. As I mentioned, you cannot outsource or eliminate every single risk. So make sure you have a cushion and don’t go and max out credit cards like some of these gurus say, and stretch yourself thin, or look at all these low money-down strategies. That worked when we were at three and four percent interest rates.

Right.

With no money down strategy, I actually have a friend out here that had a VA loan, and they put no money down, rolled in closing costs, but now they’re looking to sell the property and they have no equity. So you’ve got to know everything’s a double-edged sword. And making sure you’re investing from a place of financial strength allowed me to scrape my knees, to make mistakes, and not get taken out of the game, because real estate is incredibly forgiving, but you have to be in it long enough to see that

Exactly.

Mm.

Mm-hmm.

benefit. If you’re trying to flip, you’re really dependent upon the market. But if you’re buying for 5, 10, 15, 20 years, you can make a lot of mistakes. And I have made a lot of mistakes, but the rising tide lifts all ships and it smooths out your losses, smooths out your mistakes. So that was probably one of the biggest things I did: I kept my job. I didn’t quit and try to get a loan and start buying properties. I kept my job, I started buying, and I invested from a place of strength.

I think there’s a lot of wisdom in that answer that people need to hear. And it’s funny when you said, take action, do it. When I was an active real estate agent working with a lot of investors, I worked with a lot of engineers. And yes, analysis paralysis is a real thing, especially for engineers. So all the engineers listening, you definitely need to hear this piece about taking action. But then also, what you said about

making sure you’ve got a little bandwidth. If we’re gonna use these high leverage strategies, it’s high risk, high reward, and realizing that

there are things that can happen with that risk. And then also the time horizon. So often in our society in general, we expect things yesterday. Amazon can now deliver same day. And the truth is that’s not the way the natural world works. In a lot of cases, in real estate, we can get into a lot of trouble when we try to compress the time horizons for our returns. So I think you made a lot of really good points there.

I like to use an old Warren Buffett quote: you can’t make a baby in one month by getting nine women pregnant. Things take time. There are certain things that take time, and I wanted it too. When I was in my twenties, I was ready to set the world on fire, trying to gobble up real estate. But those properties that made me a hundred, one hundred and fifty dollars a month now make five, six, seven hundred dollars a month. And it really is just inflation and letting real estate do its thing over time.

Yeah.

Right.

Exactly. Now let’s take the flip side of that question. We asked what you got right and would recommend. Now let’s look at what did you get wrong early on that you learned from and shapes how you do business today?

A lot of that would go back to a parallel of the analysis paralysis. When I got into this as an engineer, I was trying to detail everything. Whether you’re buying properties for your portfolio and want to buy multiple, or you’re looking to systematize an agent business or management business, I detailed processes down to the last step: “we’ve got to do this, we’re gonna write this down, we got this checklist, and if this happens, then this,” and so on.

Adrienne, I’m embarrassed to say a lot of those processes we didn’t even use again. Because by the time you have another move out, three, four, five, six months down the road, you’ve learned so much. Maybe now you’ve implemented, now you’re at 50 doors and you implemented another software. So I was detailing all these things so I wouldn’t forget the next time I did it, but it was too detailed. So now a big change we make in the business is when we have a new process, we start super high level. We get a Google Doc and we just go: what’s the outcome? What’s the trigger? And we say, what are the main high-level steps? What are the basic steps? Not technology specific, not software specific, just what are the steps that need to happen? And then we go back and start filling stuff in. Because if you try to detail everything, it becomes a hodgepodge. You’ll go through, create a 20, 30 step process, and then you realize in the beginning you don’t do that piece, but it’s halfway through. You’ve tried to hire

Right.

your assistant or have somebody else do it and they’re like, well, hold on, this doesn’t even work anymore. Now you got to go back in. And it creates a big mess. So for somebody who’s starting out, when you’re trying to go into a new process or implement something new, start super basic. That will help. Then you can add stuff onto it, but start basic, start simple, kind of the KISS method.

No, I hear you, we’ve had those same issues with SOPs and processes, and I really have to say to my team now, what is the minimum we need to say for somebody to effectively do this? That is our standard. Because otherwise you get too detailed and then it gets too difficult to follow, or it becomes out of date.

Now what I appreciate about, sorry, go ahead.

No, I was just gonna say, when processes become too detailed, they’re incredibly hard to update as well, Adrienne. It’s exactly what you said. Well, I don’t even know what to update here. I’ve got to spend all this time looking through a twenty-seven page SOP to move a tenant in, and I don’t even know where to make a change. You’ve got to wait till you make a mistake, or somebody comes in and the software doesn’t even work anymore. We don’t do that anymore. With AI there’s a lot of different ways it can expedite looking through a process and expedite making changes, but still, if nobody’s gonna use it because it’s too detailed, start with the basic to get the effective result.

Now, Cameron, one of the things I love about what you’re doing is you operate both as an owner and investor and as an operator in the property management world. So often the challenge we have as investors is we have service providers who don’t think about it from an investment mindset or standpoint. So what systems or processes have you built within your property management world that only made sense because you see both sides of the table?

There are so many things, Adrienne. It’s just even how we build the processes. How do we make sure the owner is informed of what’s going on? How do we know when they need to take an action? It’s littered throughout the processes. There are little things here and there we do to make sure everybody’s marching to the same beat of the drum, and that we don’t forget we have a fiduciary responsibility to the owner clients. So there are so many things, but I think one of the

biggest decisions we made is to have a single point of contact for the owners. There are some large multi-city, multi-state companies with a McDonald’s model where one person does one thing and the next person does the next, almost like a conveyor belt or a manufacturing facility. So when an owner calls in, they need to talk to leasing to understand what’s going on with leasing, talk to maintenance to understand maintenance, talk to accounting to understand why their statements are messed up.

We don’t do that. We have one single point of contact for the owner, our asset manager. Our asset managers have several dozen years of experience. So you’re talking to somebody who has been there before, has walked that path, understands your goals and your investments, instead of calling in and getting routed all over the place and trying to talk to three different people to solve one problem. It’s always frustrating, right? You call in for a credit card and it’s, sorry, other department, transfer.

You have to explain again, sorry, another department, transfer. You have to say your name, your address, your date of birth all over again. Do you guys not have this in this system? It’s incredibly frustrating. So we’ve done that where each owner is assigned one asset manager and has one single point of contact.

That makes a lot of sense to me. I know it’s something we do in our business as well. Because

as you can see things from the client or owner perspective, and it’s funny, you hit on one of the most frustrating things ever for me, having to call a credit card company. I am nice and chill until I’m having to do that. It’s something about that process that drives me crazy. So I feel it. Great example. Now let’s talk about how a single maintenance issue moves through your systems today from tenant report to resolution. I’d love to get an insight into that process, because I’m sure there’s a

lot of takeaways for those of us who are operators in other investment businesses as well.

So the tenants have a twenty-four-seven maintenance portal. When I started, there were only a handful of options for property management software or maintenance systems, and some of them were incredibly expensive for the operator with four or five doors. Now they’ve democratized that quite a bit, so a tenant can have a twenty-four-seven maintenance portal. The tenant goes in, makes the request, and that goes directly to our maintenance coordinator.

Our maintenance coordinator looks at the request, and this isn’t AI, this is somebody experienced in maintenance, and goes, okay, that’s a garbage disposal. Here are the triage steps we’ve already laid out, because 99% of garbage disposal issues start with the same thing. Hit the reset button. Do you have a wrench to turn it? Is it plugged in? Do you hear a humming noise? Is there food in it? We’ll walk them through basic troubleshooting. We don’t want them doing electrical or plumbing work, but

if it’s something simple, we have those steps because it saves the owner money and gets the tenant’s problem solved more quickly. And if it’s not something simple, we dispatch our vendor. We work with about 50 different vendors, a lot of them specialized, and we make sure we get the tenant’s response very quickly. We use Property Meld as our maintenance system, so we’re measuring when that request came

in, how quickly it was responded to, how quickly the vendor accepted the request, and how quickly the vendor completes it. We’re watching all that, and our goal is to have it done in three days. If the tenant submits it on Monday, by Wednesday it’s been troubleshot, dispatched, the vendor has been out to the property, and we have a resolution. The vendor goes out, looks at the problem, and says, this is small, or it’s a piece of drywall work, or whatever.

They’ll handle it, take pictures, respond back to us that it’s completed, and then we get the invoice from the vendor and put that on the owner’s ledger. There are some other choke points that could happen, where we thought it was going to be just a faucet, but it’s old CPVC and it’s a huge repiping job, or it started cracking behind the wall and we have to remove siding. We stop right there, get an estimate, and go back to the owner and say,

it’s going to be fifteen hundred dollars to open this wall up and do these items, we need approval. So that whole time we’re keeping the tenant involved and having, for anybody listening, whether you have one door or a thousand, paper trails are incredibly important. Even if you’re just texting with your tenants, get stuff in writing. Because I don’t know how many times a tenant gives us a one star review and says, I submitted this two weeks ago and haven’t heard anything, when actually they submitted it yesterday, or

at midnight on Saturday and we responded Monday morning, or we responded on Sunday, and it took us a day or two to resolve, but it’s not as bad as they say. If we have that all timestamped and in writing, it makes the troubleshooting, to see if there’s a problem with the vendor or otherwise, much easier.

Yes. A couple of things there. I love what you’re saying about the paper trail. And it’s funny you used the garbage disposal example, because

with short term rentals, garbage disposal issues are my number one maintenance issue. So I think a lot of investors can relate to that. But the paper trail, and then the KPIs, and then the people: it’s a mix of systems, data, and the experienced person operating behind the scenes making sure it all works.

Yeah, and our maintenance coordinator has two main KPIs. One is resident satisfaction. After every maintenance request is complete, the resident gets an automated email asking, how did we do, one through five. I’m watching those every week. They get a quarterly bonus based on resident satisfaction. The second is speed. How quickly did we respond, are we hitting our three day KPI. And those two are very

interlinked. I could get somebody out there tomorrow, but if they do a poor job resolving the issue, you get a one star. So you have to balance speed with quality. We also have KPIs for the vendors. All those stars tenants put in for vendors, we look at that quarterly and say, wow, ABC company has five one star reviews, what happened, and we diagnose those. And we have a yearly

vendor appreciation event where we recognize the guys with the best reviews and responses. We’re also rotating vendors, offboarding and onboarding based on resident satisfaction score, because keeping tenants happy matters. If they leave, owner revenue leaves, and turnover is high risk. The number one reason residents leave is lack of attention to maintenance.

Right. And what I love about this is that role can have just two KPIs. I feel like a lot of people, when they start setting up systems and KPIs, think a role needs ten KPIs, and when everything’s important, nothing’s important. So I love that you nailed down the two that matter for that role.

Well, we used to do it just on speed of repair, but then it was, wow, they’re resolving it really quickly, because once you have a KPI, people try to game it. So we added a second KPI. You just start, and like you said, if everything’s important, nothing’s important. That’s such a true statement. Just start with something, and you might have to add one or two, but don’t overcomplicate it. I look at about a dozen KPIs every week across the entire company. Each role,

especially as you grow, should really have one, two, maybe three KPIs.

Now we’ve talked a lot about leverage, building a team, handing things off. I’m curious, what is one process or responsibility inside Emerson that you were the last one handling, and what did it take to hand that off?

There are still a lot of tasks I’ll do. Let’s say we go through a process and it’s 80, 90% done, but there are a couple little tasks in there. I’ll take the task, assign it to me, and when that process runs, I’ll get that task and it’ll say, update instructions. So once I do that, record a Loom video for the next person, or write the instructions out, I go into the back end of our process system and assign it to our maintenance coordinator or a

resident experience associate, or leasing, whatever it might be. So I still have several tasks throughout the processes, but that allows me the freedom to complete the process, outsource 80-90% of it, and just have those couple tasks I still need to do. I’ve got a thousand things on my plate firing at me at all times, so it’s nice to just have it: only when it happens, I don’t have to think about it. Okay, this is the actual scenario, let me go to the ledger and look at everything in real time. So that’s one

thing. You can also push those things, you don’t have to have the full process delegated to delegate it. Delegate what you can, and you’ll see, once you delegate it, the person you delegated to will be able to tell you what doesn’t make sense. That’s always a huge thing. When you do something for five or ten years and then try to delegate it, you realize there are other pieces in here that were just tribal knowledge that I

did. But to answer your question, the main process I was still in until recently was the make ready process. From the time a tenant moves out until we have the new tenant in place, making sure the whole turn is a seamless experience, because when there’s no revenue, that’s when the owner is paying very close attention. That’s when owners offboard. It’s the highest risk of losing an owner. And frankly, a lot of folks

might be sitting on their hands or not taking that as seriously. So it goes back to what we look at closely: how quickly we can get properties turned. Our KPI is 10 days. If the tenant moves out at the end of the month, we want that property ready and listed on the market. We rekey the property, look for property code, get estimates, get those funds, dispatch the vendor, make sure the work was done properly and meets our rent ready requirements, take photos, put the

sign and lockbox out, and that property is listed. All done in 10 days.

That’s fast. I love that. That’s very much an investor mindset. Now another aspect of delegation and team is hiring. When you’re hiring for a role within your property management business, what are you looking for that most investors or property managers wouldn’t see?

This is such a timely question, because we just had to let somebody go, she had only been with us for about a month. I realized that with trying to come up with questions about culture and can you do your job, and looking through resumes, we’ve made this mistake, so we’ve implemented, we changed this in our process. Asking the basic questions. How’s your internet speed?

Are you working other jobs? Some people, especially remote, might be working different time zones. Do you have a quiet place to work? Are you okay with this time zone? Very basic. We have a lot of ambitious goals, trying to get to several thousand doors in the greater Houston area. So we’re very clear this isn’t a position where you can have multiple jobs, or think you’re just gonna be sitting there doing nothing most of the time and then have to

jump in. We have daily meetings, KPIs, we’re very ambitious. The final meeting I have with every single hire is I’m almost trying to dissuade them from joining. Before I was, yeah, this is what we’re doing, this is where we’re going, trying to not

be too positive, sell the dream, sell the vision. But now I’m a little more negative. Not in a bad way, just, hey, we’re kind of a startup. We don’t have an HR department, we don’t have a benefits department, we don’t have all these things ironed out. Every process isn’t done. We don’t have people that only handle one thing, you’re gonna be wearing multiple hats. Sometimes you’re going into the unknown, and we need to be ambitious and ready to jump in,

even if it’s not your job, which is one of the phrases I think I hate the most. But it’s one of those things where you’re able and willing to jump in and want to be part of this. So I dissuade them a little on that last interview, and that has seemed to make some people go, you know what, they’re right, I was looking for more of a cushy job that I don’t have to work this hard. And I get that. That’s fine. A part-time person, or somebody later in their career who doesn’t want to grow or learn,

wants to do what they’ve been doing and do it the same way, that’s not a fit. So the big things have been very basic questions up front about quiet workspace and situation, since we’re 100% remote. And then the final interview with me is telling them all the downsides of working with Emerson, making sure they don’t feel bait and switched. Those have been the big things.

That makes sense. I love that insight, and I agree, sometimes you don’t want to oversell it, because then you get people who won’t like the reality. So let’s talk about, what intrigued me is you said you’re pretty much remote and virtual for the business, you’ve got people all over.

We have people in five different countries.

I love it. And there’s a lot of value to that, and it also means you have to be really intentional with how you manage and lead them. Let’s talk about accountability. How do you handle accountability on your team, since people are remote, you can’t just see whether they’re at their desk. How do you know something is off before it becomes a bigger problem?

Adrienne, I think we hit it earlier. It’s the KPIs. How do you have an objective measure for success for that role? When we’re posting a job, we’re talking about the leasing person, they need to have days on market, that’s the biggest KPI for that role. If it’s a turn coordinator, it’s move out to make ready, 10 days. We put that in the job description, make it as clear as possible, so they know that every week we’re looking at all the

make readies, all the properties with maintenance requests, all the moveouts, everything we’re looking at, but objectively. Instead of, yeah, I feel like we’ve had a lot of evictions lately, or I feel like these things are taking a while, it’s, actually everything looks good, or it doesn’t. And what I like to call taps, hey, we’re starting to see move out to make ready days creep up, we’re starting to see days on market creep up. That’s a tap we look at weekly to say, let’s look into that. What is it?

Maybe it’s this one property we knew was gonna take longer, a ranch house way outside of town, no big deal. But hey, if it’s four or five different properties, and we notice feedback from agents that the property’s not clean, or doesn’t look well done, the paint’s not touched up, those KPIs, especially broken out by role, that person is accountable for it, and we look at it every single week. I had a meeting this morning with the entire team and we went through

the KPIs, is there any issue, is it on track or off track, if off track, what’s the issue, why is this KPI not in range, and we talk about it together, and try to do a deep dive. Sometimes there’s no deep dive needed, an appliance part took two weeks, nothing we could do, outside of our control. But sometimes, wow, we realize this vendor is being very late, getting one star reviews,

we need to do something. So let the KPIs drive the accountability, and it prevents it from being an attack, like, you’re not meeting up to this. It’s just, why is the number the way it is, and let’s dive in collectively as a team, use all our brain power to figure out how we can get this number back in the normal range.

I love that, and I love that use of KPIs, because it changes the conversation and gives you hard data. So as we wrap up, one final question. Sometimes investors think they want a certain thing from a property management company, and it’s not really what actually matters. What’s the misalignment you see between what investors think they want and what actually protects their returns?

I think it’s cost, and I don’t blame them for this, I did this in the beginning too. How much is a management company, they’re $100 a month, $200 a month, whatever, fifty dollars a month. We can see that cost very easily, because on your PL you see your rent coming in, your mortgage, and a management fee. That’s a cost. But

what you don’t see, and what I really had to learn, is vacancy. I’ve done so much data and analysis on this for our owners regarding vacancy killing cash flow. There are property management companies, we’ve hired people from them, where 30 days is their turnover time from move out to listing. That’s one eighth or one twelfth of your rent for the year, which is eight point three percent,

already off the top. If it’s a $2,000 a month rental, you’ve lost two grand already, which is a little over $150 a month. If you could get that down within a week, you could almost pay somebody’s management fee in that first month. So it’s really looking at how much money you’re potentially losing at the end of the year. If you’re looking at your 1099s or PL and wondering why,

you didn’t make any money this year, well, if the turnover took 30 days, or 60 days to lease, and you keep stacking these things up, the property wasn’t really able to make money during that time period. If you’re out of commission 20, 30% of the year, that’s a lot of money to make up. If it’s two or three months at $2,000 a month, that’s six grand, or $500 a month for the year lost. So that’s one of the big shifts,

making sure you get that property in service as quickly as possible, not just looking at cost. We believe in one point of contact to help expedite decisions and have somebody experienced lead you through the process. But if you go out and hire a $50 property manager, sometimes the most expensive thing you can do is hire a cheap property manager. That person might be outsourced, like your credit card company, where you have trouble talking to somebody experienced. I just don’t want to hand over three to five hundred

dollars a month in rent to somebody who doesn’t have the experience to protect it.

That makes a good point. Well, Cameron, thank you, you’ve shared a lot of wisdom as an investor and as somebody running a property management business, that will be very helpful for our listeners. If a listener would like to get in contact with you, and you also do long term property management in Houston, tell me more about that, is that your market?

Yeah, just Greater Houston area. Long term rentals, Greater Houston area. If somebody wants to get in contact with us, just Google Emerson Property Management, or go to EmersonPropertyManagement.com, or search my name. You’ll find us there. We have free rent analyses, all sorts of guides, and an accidental landlord toolkit if you’re having trouble selling a property. We give away a bunch of stuff for free on there, so you can get in there and get educated.

I love that. Awesome. Thank you so much, Cameron, and thank you to our listeners for joining me for another episode. If this was helpful, please make sure to thumbs up and subscribe wherever you’re listening, and join me again next week for another amazing guest.

The post One Owner, One Contact: The System Behind 300 Managed Properties appeared first on Adrienne Green.

Every real estate entrepreneur reaches a point where the business they built can no longer run through sheer effort alone. In this conversation, I talk with Niyi Adewole, who went from a single house hack in Louisville to a 30-unit rental portfolio, a ground-up self storage development, and a 10-agent investor-focused real estate team spanning three states. Niyi walks through the tasks he held onto for far too long, from invoicing to transaction coordination to guest messaging, and exactly what pushed him to finally hand them off. We also dig into how he evaluates new opportunities, how he manages a business across multiple states without ever setting foot on some of the properties, and why he believes consistency beats big bets every time. If you have ever felt like your growth is capped by your own hours in the day, this one will give you a lot to think about. 

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 listeners and welcome back. I’m Adrienne Green and today we’re here with Niyi Adewole. Here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start, and Niyi is a great example of that. Thanks for being here with me.

Thank you for having me. I’m pumped to be on.

To start off, give us the quick version of your portfolio and business and what they look like today.

My name is Niyi Adewole. I have been investing in real estate for over a decade and built that portfolio well before I got a license. I got licensed in 2021 and have now built out a team. What it looks like today is I have a self-storage unit that’s 225 units that we built from the ground up a few years ago. I used to have 30 long-term rentals, but I traded those in to build that self-storage and buy some other properties. I own eight short-term rentals, five long-term rentals, and I land on flips and then help other investors get started in real estate as well.

I love a lot of your story and we’ll dive into the pieces, but some of the great things I’m hearing is that you’ve adapted and pivoted. You didn’t just stick with what you started with as you learned and grew and different opportunities came, and you weren’t afraid to sell what you started off with to transition into this higher level of real estate investing that you’re doing now.

Absolutely. And it was not all me. This is definitely with partners and help from the outside because I wasn’t the one that came up with that self storage idea. I consistently took action every single year, building that portfolio. And when an opportunity arrived, I looked at it, ran the numbers, said, this makes sense, and I took action.

Love that. So let’s go back a little bit more to the beginning where you went from a three unit house hack straight into a 12 unit as your second deal. That’s a pretty big jump. What made you comfortable scaling that fast? What wisdom can we have for listeners who may be in that same place? And what would you tell somebody who’s maybe a little fearful of a jump like that?

I would say the main thing is taking that first step. Having the courage to go after a 12 unit, it’s not something I would have done for my first deal. Not at all. I had to do the first deal and then sit on the sidelines for about 18 months saving money and looking around for another deal before this opportunity came up. And the reason I felt comfortable taking that one down is because I got that first house hack. Prior to even getting that first triplex house hack where I lived in one unit and rented the other two out, I’d been listening to and reading books, and listening to different podcasts to gather information and understand what I was doing in this space. When I took action on that first one, it gave me the power to take action on the second one. And the second one was literally three houses down from the first one. That 12-unit opportunity was on the adjoining street. I felt very comfortable having walked that neighborhood many, many times, and comfortable in the numbers I could pull in because it had similar unit sizes to that triplex to go after it.

I love how some people might have been too scared to make that jump to that twelve unit but you realize, this is in my neighborhood, this is an area I know, I know these numbers really well, so I’m not going to get scared away arbitrarily just because it’s a lot more doors.

Absolutely. The main thing with it is that the zeros just get bigger. There’s nothing that really changes with the numbers outside of the lending piece. When you go after twelve units versus four or less, you’re looking at more of a commercial loan, which is slightly different. But from checks and balances, renting out units, getting the most that you can from different tenants, renovating units, all that is about the same. Now you’re just bringing it to a higher scale and it depends on what level you’re at, your life, to be able to take that one on.

Now, a lot of your story is about evolution. Let’s talk about asset class. You’ve done small multifamily, ground up self-storage, a lot in the short term rental and midterm rental space. How do you decide which asset class deserves your attention, or how did that evolution happen?

My bread and butter is residential, small, multifamily for long-term rentals. That’s what I did the first five years of my investing career. I went from that triplex and was able to build it up to 30 units. That was all I was going to do. This works, no need to do anything else. But I started meeting other investors along the way and they encouraged me, before the pandemic boom, to try out short term rentals. When I got promoted through my W2 at the time, which was medical device sales, and moved to the southeast, I bought a house hack and turned that house hack unit into a short term rental just to try it out. At that time, if I could make fifteen hundred dollars a month, I was going to be golden. I said, let me try this thing out. I know I can get that long term, let me see what we can do short term, just put some furniture down there. I was able to pull in about twenty five hundred a month. That’s when my eyes were opened to the short term rental market.

I went all in on that. Circling back to how I got into the commercial space and building that self-storage from the ground up, that was all by working with an investor-friendly realtor to build up that unit of 30 units. I was buying those in Louisville, Kentucky, all within a mile of each other of where I used to live. I started working with an investor-friendly realtor who owned even more real estate than I did. She was the one who, after working together for six or seven years, said, of all my clients, you’re the one with the most similar mindset and the growth mindset, and I’d love to work with you. I was comfortable working with her because a partnership is almost like a marriage. You really have to know that other person. She brought this opportunity to buy this land, build self-storage, and do a townhome project on that piece. It took about six months of negotiating with the owner, but we were able to close on it and kick that project off. What I did was sell these units to put my portion of the money into that storage as well as to buy some more properties in Atlanta where I reside.

I think there’s a lot of great wisdom and takeaways from that one story. I was an investor-friendly agent actively working for a number of years. I know you are that now. Sometimes investors don’t necessarily value a relationship with an agent. They’re going to go with whoever brings them the deal, they’re kind of agent agnostic. I can see why they’re doing that and yet they’re missing out on opportunities like what you got in Louisville.

I think you’re spot on. I used to be that guy. I still remember that because I’m still an investor. One of the things I used to hate doing was signing a buyer brokerage agreement before we’ve actually done anything. One of the practices we do is you have to sign one before you can show a property now. But the way we work through that piece, especially because we focus on working with investors, is we identify rock star properties and we’ll put offers out there before we even go and see it, just to see if we can get this under contract. And in that we have a buyer brokerage agreement, and then we’ll go check out the property when we have it in due diligence. A lot of investors, at least before they meet our team and have conversations with me and others, tend to not value that real estate professional as much. I would say you’re missing out. Not just on writing offers and contracts, anybody can do that. But when you see that we’ve been through over 180 deals, probably way more than most of the investors we’re working with, and we’ve been able to negotiate a crazy amount of credits, a crazy amount of deals. There was one in particular where we were trying to help a client buy their second short term rental with us up in the mountains. It’s two A frames sitting on ten acres of land. It was listed for one point two million. At that price they didn’t have the funds to come forward and do that and they’d have to finagle and pull from all different places, and they didn’t want to do that. We were able to work out a deal where we’re essentially going to get two hundred thousand in seller credits, to help them furnish the whole place, get it up and running, and only have to come with the down payment. We were able to rework that because we think like an investor and we’ve helped other investors do this. Not to mention, when you look at having an investor friendly realtor, the value is in the list of vendors and the list of contacts, they can help you get to your goal. If you share the goal you’re trying to reach with them and you check in with them constantly and they’re checking in with you, there’s so much help I had along the way. If I need a roofer, if I need a plumber, I’m just going to get the exact person she’s already negotiated with, and they’re going to help me, and we do the same for our clients.

I love that you brought up a lot of good points of what that relationship can offer to investors. And the other thing I loved from that story is how you did the experiment with the short term rental house hack. That’s something I love, how can we just dip our toe in the water, how can we test this out and recognize that this isn’t like before we sell our whole portfolio and pivot to a new strategy. Let’s just see if it’s for us with a little taster. I love how you did that. I’m curious what other wisdom you would have for people along those lines.

I’m always a fan of trying the one that’s going to require the least amount of capital for you to at least test this thing out. If somebody’s willing to delay gratification and they want to get started in real estate, I’m always pushing people toward a house hack. Go get a duplex, triplex, quadplex like I did, live in one unit, rent the others out and have the tenants pay most of your living costs. Now you’re winning on every front. You have to live somewhere. Your living is subsidized and you’re seeing if you actually like this thing. If you don’t, you move out in a year, you don’t have to do it again, you have an investment property. If you do like it, maybe you find a passion and you grow from there. Whereas I have a lot of newer investors who say, for my first property, I’m going to go do a huge flip and a luxury flip. Yes, there are some people who are successful there, and we will help you if you’re adamant, but we always pause for a second and say, why do you want to do this for your first one? It’s going to require a certain amount of money. Even though you’re getting hard money, they’re still going to charge you points. You’ve got to put down twenty percent if it’s your first one. There’s a lot going on and it’s almost like riding a motorcycle without a helmet. Whereas doing a house hack where you’re going to put down five percent, three and a half percent, it’s really hard to mess that up. It’s like riding a bicycle with the tricycle pieces that help you as a kid. It’s a way to get started with a little bit less. We always push people toward doing something like that for their first investment, as opposed to going all in and putting down fifty percent on a property.

I think that’s something also when people work with an investor friendly agent, you get that wisdom, and one thing I know from when I had my team, that resonates, is a good agent isn’t just going to say, yeah, that sounds great, to the thing that’s going to give the biggest commission. If somebody’s wanting to do that luxury flip, that’s going to give the biggest commission, and a good investor-friendly agent’s going to say, let’s set you up for success, even if I’m going to make less on this first one, because my priority is you as the client, as the investor, doing well. If you like the investing, I’m going to make a whole lot more money in the long run because you’re going to keep doing it again and again.

Adrienne, what you just hit on is the key. We share this with our clients. That is literally our model. It’s not the first property, but we want to be there for you through the first 30 units that you build. The same way I did with the other agent who’s now my partner in the self-storage. With her, over a six or seven year period, I bought thirty units and I’ve now sold those thirty units. That’s millions of dollars in revenue for her business that she doesn’t have to keep coming back to the well for. I was coming back because she was excellent. She’s been awesome. She’s been awesome as a partner. My goal is to develop the same thing here. We’ve already had multiple clients who have come back for their second, third, fourth. Right now, under contract, I have a client buying his fourth short-term rental. He moved down from New York, he lives in Metro Atlanta and he’s doing this full time now because they’re killing it. I have another client buying their second property. They bought a four-plex maybe two months ago. Now they want to buy a short-term rental to save on taxes because we connected them to our investor-friendly CPA and they’re talking to them about saving on taxes. When you look at my team of 10 agents, half of that team came from people we helped as clients first, by their first, second, or maybe even third deal. Then they liked the process so much that they went and got licensed, joined the team to help others. We’re thinking more long term. That’s why we wanted to get into this niche of helping investors, because not many realtors can speak the way that you speak and I speak. We’re actually investors trying to help people. Most realtors are kind of out there just showing regular houses, which is fine, but we wanted to purposely target this niche because if we do this well, we’re going to have repeat business for a long time.

Now we’re going to talk a lot about systems, because I know on your investing and management, property management side, and also with this real estate team, there are a lot of systems. Let’s break down some of that for our listeners, both investors and agents, with some wisdom they can walk away with. The first shift I want to talk about that we see a lot in the investor space is you were managing your own units and now you are managing or co-hosting or helping other units in the short-term rental and midterm rental space. I’m sure there were some lessons learned, maybe some the hard way. How did that shift, starting to manage your short-term rentals and midterm rentals, teach you about your own operation and help you improve your systems?

You’re going to have to go through the fire. There’s going to be an in-between period where you can’t necessarily pay people a whole lot to join the team, but you’ve got to push through, and you’re going to be working an insane amount of hours during that time period to make it happen. Specifically talking about the short term rentals, I started out just managing that one in the basement, the house hack. It was doing so well that after three months, I bought a full-on house in the same neighborhood and we made that a short term rental. I was connecting with other investors in the city because I was newer here and started managing some of theirs. Very quickly I went from just managing one to like four or five by the end of that year. Then word of mouth started getting around and others started coming on board to help. Initially it was just me. It was me and software. I use a software called Hospitable, which allows you to automate a lot of the guest messaging, which is amazing. It also allows you to automate the cleaner messaging and give them a calendar so they can see where their next clean is. Initially I was just trying to do this through the app, and I missed one or two cleans that were last minute ones, where somebody extended or somebody checked out early and we needed to get the place cleaned. It was terrible. I’d recommend implementing software immediately, like Hospitable or others out there. Then there’s that happy medium point where you start to get to the point where, and my wife will attest, I was still messaging guests at like nine PM, 10 PM. When are you putting the phone down? We got into this so you could have more free time. That’s when I started looking around. There were a couple of people raising their hand and saying, can you teach me this, can you help with this. I brought two of those individuals on and I could not pay them much. It really was selling them on the vision of what this was going to look like a couple years down the road. I was able to do a percentage split of the revenue we brought in from a property management company and they were okay taking that and working together to handle the messaging. That was the first couple hires we made. Fast forward to today, we still have one of those two individuals with us. Now she’s moved into an operations manager role and she’s making a whole lot more, salary plus a couple bonuses. Now we have VAs, we’ve got AI, we’ve got a bunch of different cleaning teams, and all of that has gotten a lot easier. But that messy middle is a time period where you’re going to be working 16, 17 hour days to try to make it happen. Once you get past that and push to that larger level, you’ll have enough income coming in to actually hire people to do all the work. Now I don’t message at all. I don’t do much, I just meet once a week with the team to make sure we’re on track and give guidance on certain things. Then I work with new owners to get them onboarded and I go from there.

I love that. That leads perfectly into the next question. I also love Hospitable, but let’s talk about when you started to get those team members on for property management. When did you start to identify processes you could document and hand off? How did you do that? That’s something a lot of listeners struggle with, they’re like, I know how to do it all, it’s all in my head, how do I hand that off to someone else? How did that work for you?

It took a lot of setting aside time to make it happen. Nowadays it’s easier than ever. I’ll talk about how I did it and how we do it today. How I did it is I read a book called Traction, which I think you’ve probably read and a lot of people should read if you haven’t, as an entrepreneur. One of the things they talk about is elevating and delegating, which is, every single day you should, but every week at least, you should be thinking about, what’s taking up most of my time that’s a repetitive task that can be delegated to somebody else, so I can elevate to another level and bring more business in. I started one at a time taking, this is something I do, like coordinating maintenance. When things come through, how can I shift that over to my guest experience team? When it comes to even the messaging, always look at it in two ways. One, can I automate this? In Hospitable, a question we get all the time is about parking and about Wi-Fi. Can we have an automated message go out? Can we tell people ahead of time and then if they ask, have an automated message? Yes, let’s do that. If it’s something more obscure, what we did is put together a Google sheet. Anytime there was a weird question, I had the team reach out to me, I’d give them a response, and then they added that to the Google Sheet. Now there’s AI within the Hospitable system, and you can just put it directly in there, give it the answer, and it’ll start responding for you. What I’d say for people moving forward when it comes to putting together systems is utilize what we have. Now, when it comes to putting together a system, I don’t even write anything down. It used to be, I’d go into a Word document or Excel sheet. Now I record a voice note, talk through the whole system, copy that, paste it into Claude or OpenAI or whatever AI system you’re using and ask it to create an SOP that’s very simple to follow. That’s what I’ll put in. Taking it a step further, you can also just put that into the Hospitable AI, and it will understand and know the SOP and be able to respond for you and pull from that knowledge portal if a guest has a question. It’s gotten easier over time. I like using Loom too. Anytime I need to show my team, whether it’s the real estate team or the short-term rental team, how to do something, I do a Loom video, two minutes, three minutes, send it their way, and then we keep a repository of that in a Word document that gives you a description of what it’s talking about. If you ever need to find it, you can just search and click it.

I agree with you. I built my team before AI, and yes, we had to actually write SOPs. I made the video and my VA had to type up the SOP, and now you can get a pretty darn good one just by putting the transcript of a call into AI. It’s easier than ever. I love how you saw that. You also made the point that it’s going to take some of your time at first to get those things out of your head and get them transferred. People are reticent to acknowledge that, you almost have to slow down to speed up sometimes.

You are spot on. The best thing I can tell you is use your calendar to control your day. For the elevate and delegate, I still have it on my calendar. I set aside time every Monday and every Friday to think through what’s taking up most of my time, can I delegate this. If I need to put a system in place, it’s during that one hour time frame that I’m recording the Loom video, putting together the SOP with AI now. I make sure I’m checking it twice, checking it three times, because once I get this off my plate, I don’t have to do this again. I’m sure you do the same for things like this podcast. If you were the one who had to record the podcast, find the guests, and do all the edits and all this stuff, which you probably did starting in the beginning days, there would be a lot less guests and a lot less content you could put out. Over time you start to realize you don’t have to be the one doing all this. Even in the realtor business, I did the exact same thing. You can ask my wife, she can attest to this. There used to be times where I’d be working 16 hour days. Now I have a team and we’ve built it in a way where it’s almost like our apprenticeship model. I’m done work every single day by 5 PM. The only time I work a little bit past that is if the due diligence is ending that night and I have to make sure we get something done. I don’t even show most of the properties we’re doing. Some of my more junior agents are out there showing while I work on the biggest priority piece, which is negotiating a deal, making sure the numbers work, making sure it’s in the right area, and setting our clients up for success. All that came from the elevate and delegate and really thinking through how we can move this off my plate so we can serve more. If it depended on me to show every single person, there’s only so many hours in a day. But if I have a team showing all the people, I can help 10, 20 people at one time.

I love all that, it resonates. I’d say for our investor listeners, in my opinion, you get better service when you work with a team than with a solo agent because of what he’s sharing here. If you’re working with a solo agent, your ability to see that house, even if it’s remote and you’re having the agent take pictures for you, is limited by their hours in the day. But if you’ve got a team, they’ve got junior agents who are a lot more available to see that house and do that showing than if you’re working with one agent by themselves. Another thing is, you could speak to more, like you mentioned, you guys do a lot of deals. My team was doing over a hundred deals a year, so we saw everything. Whatever came up, let’s say a low appraisal, I knew a solo agent for whom an appraisal under the purchase price totally threw them for a loop. For us, it was no big deal because we dealt with it several times a year.

You’re a hundred percent spot on and we lean on each other. There are certain things that, as a team leader, I haven’t done before that I’m leaning on my team for. One of my team members is a retired CPA. We helped her buy two properties, one short-term rental, one personal property, before she moved down here from Boston and then got her license to join the team. She moved into a 55 plus community. I’ve been over there to hang out and it’s kind of cool, but it’s a whole different process when you’re buying one of those houses. Fast forward, we had a client two years ago looking to buy in a 55 plus community, and I was able to lean on her for all of her knowledge to help this client. She and I just partnered and she said, this is how it goes, the contract looks completely different, okay, we’re going to do it. It was completely different from a normal process. Because we have that team, we can lean on each other as opposed to trying to figure it out by yourself when you have that client’s trust.

That’s a really good point. Now, let’s say there’s a lesson you learned the hard way. Is there a task you held on to too long before finally delegating, and what pushed you to finally let it go?

One was invoicing. That’s one thing I was a little touchy on, for my short-term rental owners. I needed to make sure I saw each of these to make sure there wasn’t a discrepancy. That invoicing, when you go from four units to now managing over 25, can take up many hours in your day alone. You’ve got all these receipts and things coming in and you’re checking everything. That was one of the ones I was last to let go. When I did and I finally trained somebody on it, the time that opened up and the mental freedom, I didn’t realize, but it was almost making me not want to take on more short-term rental clients when people would raise their hand and ask if I was open to it. I’d try to make up some excuse, well, maybe you should manage it yourself, as opposed to jumping at it and saying yes, let’s do this. That was one of the things keeping me back, knowing this was going to be another headache of sending all these invoices. But now that I’ve moved it off, it’s been incredible. Another piece, I think I held on to doing the transaction coordination for way too long. I did it for the first two years in real estate before moving to a transaction coordinator. That would take up about four hours per deal to put all the documents in and then send all these agreements out and make sure everything’s getting signed. That was a mental weight as well. At that point I could probably only work with three, four clients at a time because I had to make sure all the dates were up and I was reminding people about upcoming dates, and I didn’t want to miss anything. But now adding that transaction coordinator into the team has been a game changer. Now I don’t have to think about any of that. They’re the ones sending all those messages. They put the dates right in our Follow Up Boss so we can see it at any time and it makes it so much easier.

I agree. Everything you’re saying is so wise. A lot of people hold on to finance and accounting stuff. People don’t want to let that go. The truth is that’s something other people can usually do pretty well, and they can’t actually move money, they’re just doing the paperwork associated with it. It doesn’t give them access to move money out of your bank or anything.

Hundred percent. There are so many controls now that you can put in place because we use QuickBooks for that. We pay our cleaners on the first and the fifteenth, and I used to be the one to look at all the notes and figure out how much, then send the payment. I thought on one of those elevate and delegate days, if this is taking a lot of time, how can I cut that whole time? Now I have my executive assistant. She puts all that together because she can see everything, all the cleanings, all of it. She puts it all together and sends an email to the cleaner with me CC’d to say, this is the amount we’re sending, does this look right to you? They tell her any discrepancies. Now I know the exact amount, and it only takes me five minutes to send payments to everybody on a Friday, which is amazing.

Love that. Now the last thing I want us to discuss is how you operate across multiple different states with your real estate team, Georgia, Florida, and Texas. Both for investors and agents, they often feel they’ve got to be able to touch the real estate. People have a lot of challenges with doing anything long distance. I’d love for you to share some wisdom on how you manage a business long distance.

I think this comes back to a little bit of my past. I was in medical device sales for seven years. During that time period I got promoted four times. The first promotion moved me from Philly to Chicago. Then I moved to Louisville, Kentucky, which is why I started investing there. Then I moved to Boston, and the last promotion moved me to Atlanta. In that whole time period I could have made the excuse that I was going to pause on investing because I couldn’t do it in my backyard in Boston, it was too expensive. But I just kept investing. When I was in Boston for three and a half years, I was able to build that portfolio from the three units I started out with to thirty through long distance investing. That got me comfortable with not having to be boots on the ground to see every single one of these properties. I just need to know that the numbers work, that there are checks and balances where I can send in an inspector to check out everything, and they’re going to give me a much more detailed report than I’d be able to see anyway, and I can use that to negotiate. When it comes to the real estate business, it’s very similar, especially in this niche. If we’re in a niche of more retail, where somebody’s going to make this their forever family home, it’d be a little different, where you have to go see every single one of these before you get it under contract. But we’re in the investment niche. What we focus on is making sure we’re really good at running the numbers, making sure we have a good idea of different neighborhoods, or have a specialist in that state who knows about the different neighborhoods they’re looking for. Once we find the deal, we put it under contract with enough days of due diligence that we can get out and see it once it’s under contract and make sure everything checks out. That’s kind of how we work it, and it’s been a joy. The first expansion wasn’t me saying we’re going to go take over the world. The first expansion happened because we had ten or eleven agents in Georgia, and one of them was moving back to Florida because her husband was going to pursue a PhD. I asked if she was still trying to practice real estate, and she said yes. Then some of the clients we helped in Georgia, once we mentioned we were now in Florida, reached out and said they actually wanted to buy a vacation home in Florida. We helped them, helped some others, and just kept growing from there. Then Texas was an agent who reached out specifically to join our team and expand us out there. Now we’re in Georgia, Florida, and Texas. It’s been amazing so far.

That is awesome. I love it. I can just hear throughout all your different experiences that you’re sharing, a few themes: team, leveraging other people, their skills, their wisdom, their experience, and not having fear, coming back to the numbers and not being afraid just because something is different or you haven’t done it before or it’s not how other people do it.

That’s the key. I think now more than ever, with the technology we have, especially being able to do a video walkthrough, being able to research even more detail than we ever could with some of these AI tools, there’s less excuse for investing far away or taking on something new. You’ve got more tools than anybody before us who built these amazing companies and businesses.

Very good point. So thank you so much for everything you’ve shared. If somebody would like to reach out to you because they’re looking to buy an investment property in these areas or looking for somebody to help manage theirs, what’s the best way for them to connect with you?

You can check us out at Ekabo Home dot com, which is EKABO Home dot com. It’s the same name on Instagram. You can Google me. We’d be happy to help you.

Love that. Of course, if you’re driving or anything, it’s all in the show notes or the caption below. Thank you so much. And for our listeners, thanks for joining us on another episode. Catch us again next week with another amazing guest.

The post From Medical Sales to a 10-Agent Investor Team Across 3 States appeared first on Adrienne Green.

If you have ever felt like your business cannot move without you personally holding every relationship together, this conversation is for you. I sat down with private lender Alexis Morgan, who built a fund from eighteen years old with no corporate background, no playbook handed to them, and no shortage of moments where they thought certain tasks could only be done by them. What changed was not working harder. It was learning how to turn relationships, investor communication, and even the parts of the business that felt too personal to hand off into real systems their team could run. If you are scaling a real estate business and trying to figure out what to build, what to delegate, and what still needs your hand on it, this one will give you a lot to think about.

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I’m Adrienne Green and today we are here with my friend Alexis Morgan. Here on this podcast we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start. Alexis is an interesting story because I don’t know that you ever really experienced the grind. What do you think?

I think entrepreneurship in the beginning is the utmost description of the grind. Not in a traditional sense, but I definitely went through a period of startup and ramping up for sure.

That’s very fair. And yet you are unique because you really started as a real estate entrepreneur before you were ever any other business person, I believe.

That’s correct. I got started in real estate at eighteen years old, and I’ve been doing real estate now almost five years. It’s been the only thing I’ve focused on, the only thing I’ve known, not coming from a traditional corporate background.

I’m curious, you were eighteen, you were in university. How did you get exposed to real estate as an option? How did it enter your world?

It started when I was sixteen. One of my friends, her father was a real estate entrepreneur working in the hotel industry, and they had massive success that you could see because of the vacations they would go on, the house that they lived in. I was always curious what this family was doing. What is behind the curtain? How are they making money? That’s where the curiosity sparked. But the actual action came from a book. I was in college and I picked up Rich Dad, Poor Dad, and that was the formula on how to execute on that dream and that vision. From that book is when I really got started. That was the exposure I needed to know what’s step one, what’s step two, and what’s step three to making this thing work.

I love that, and I love when we get a playbook and we can execute. I believe private lending was the first thing you did, hard money lending?

Before I was a lender, I got started in the buying and selling of property, wholesaling and fix and flip. That was the foundation before I went into hard money lending and private lending.

Knowing that lending is a big piece of your world and what you’ve focused on, how did you get into lending, and why did you decide this is the strategy you were going to run with?

Such a good question. There are moments in my life where mentors left a huge imprint on me. When I was wholesaling and flipping houses, I was always going to events. I always wanted to learn more and get to the next level. I’m a huge learner, hungry for growth. One of the events I went to was around syndications and funds and raising money, and there was a gentleman on stage who said, look, you all out there could be running as fast as humanly possible, spending all your energy running as fast as you can, but if I’m on a skateboard, a bike, a scooter, or a car, I’m going to go faster and further with less effort. He said, make sure you’re in the right vehicle. That’s when it really hit me: I’m working really hard, but what am I working on? What am I really working on? From that moment, I started to look at other aspects of real estate that would allow me to have more leverage, that would allow me to go faster and further with the same or less effort. I interviewed my developer friends, I interviewed other fix and flippers, I interviewed people who bought multifamily. I tried to get a real perspective on these other parts of real estate, and I also talked to lenders. The lenders always seemed to have the most leverage. Deals would come to them rather than them having to do these crazy marketing strategies. They also didn’t carry so much of a fulfillment burden. As a flipper, you have to go in there and do the floors, do the paint, list it, make sure you’re marketing it correctly. For lenders, the fulfillment was essentially due diligence up front, send the wire, and then you make money on and on. I was really attracted to the business model, and that was the click for me that made me switch from fixing, flipping, and wholesaling to being a lender and starting to get cash flow through that aspect. I even talked to people who own rentals, and from my understanding of their perspective, it wasn’t all that it was hyped up to be, as you might see online.

I can relate. I do primarily private lending myself as well, and having done the other pieces, when our borrower is really struggling because their contractor goes to them, that sucks. I have empathy for them, and I’m really glad that I’m not that flipper right now. I’m really glad that’s not my problem to solve because I’ve been there, done that, and I’m good with not solving that problem anymore.

A hundred percent.

Part of the challenge in the lending space is responsibility and reputation, for people to trust you and for credibility. You started your first investment fund at 20. How did you do that? A lot of people have expertise in another industry that they’re able to transfer as credibility here. What did you have to build in terms of systems and credibility for investors to trust you with their capital?

Such a good question. A lot of people ask me how I did everything so young, and the most honest answer I can give is that I didn’t do it alone. The thing about getting started is you’re going to pay in time or money. I would much rather pay in money, whether that’s partnering with someone, a mentor, or getting a team together, than trying to figure it out for ten or fifteen years. How do I get an investor to trust me? How do I get a borrower to agree to my term sheet? The reason I was able to have success at a young age, at 20, when I launched my fund, is because the first thing I did was hire someone to teach me how to structure my fund, how to put a good deck together, and how to raise money. What I will say about raising capital is it comes down to relationships, and that’s something you can never buy. Since I was 18, I was going to networking events, I was posting on social media, I was showing people my character, that I could perform, that I do what I say I’m going to do, that I do good work, all these things that build up a positive scoreboard in the minds of people when it comes to who you are. That you can never buy, but the technical things I tried to fast track as much as possible. I had a partner early on who had done hundreds of fix and flips, and I used him as a way to show our team has experience evaluating these deals and experience looking at construction budgets. That was key to getting started and ramping up: being the connector of it all and putting together the strategy, rather than wanting to make as much money as possible and wanting it all to myself and hoping it works out. I was huge on being willing to have ten percent of a watermelon, or fifty percent of a watermelon, rather than fifty percent of a grape or ten percent of a grape, and trying to do this all myself without anybody’s help or insight.

I totally resonate with that. I know that when I was an active real estate agent and I had a real estate agent team, that was what I would work to communicate to agents to be on the team. It’s like, yes, you pay some to the team, but you’re getting a reputation. We’re bringing you leads, we’re giving you operations, so you can do more business, and you have fifty percent of a watermelon instead of a hundred percent of a grape. But the truth is a lot of people have a hard time internalizing that concept. You and I get it. How did you come to that mindset? Was there something that made you have this idea of abundance and the idea that you can net more even with other people getting some as well? Or was that how you were raised? How can I help other people have that mindset?

I think someone said to me early on, the way you get whatever you want in life is by helping other people get what they want. It’s the law of reciprocity. That was one of the core pillars that helped me develop a mindset like that: if I want to have success and I want to raise money and I want to lend, who do I know that’s doing that? What do they want? Do they need more leads? Do they need more money? How can I help them? Because in turn, I know the law of reciprocity is almost as sure as gravity, that I can start to build some success on my own. That was the first thing. But the second thing, which might be more important than the first, comes back to what I said earlier. You can make money back. If you lose money, or if you lose a t-shirt, you can go and buy another one. But you cannot get time back once it’s spent. The concept for me that I really got behind was: do I want to spend five, ten, fifteen years figuring this out and trying to do this on my own? Or am I willing to pay a mentor or split profits doing this with someone who’s been doing it for five, ten years, who can show me the ropes and speed up my learning curve? Those are the two mindsets that have been really essential for that action to take place: you can’t get back time, so try to cut down how much time it takes you. This is why I read a lot of books. Someone’s lived a whole lifetime. They’ve distilled the most important lessons of their life into 100, 150 pages, and they’re going to give it to you for 20 bucks. That’s a steal, all day. I look at mentorship that way. I look at business partnerships that way. It’s someone giving you decades of experience, decades of knowledge, and those two mindsets really helped me get over that hump of “wait, but it’s all mine.” Once you have this skill set, you like, now I run my own lending business. The first two years I had a partner and I was doing deals with other people. Now I do deals on my own, but I could never have done deals on my own this quickly if I hadn’t taken those two years splitting profits and paying people out. Those years I was gaining knowledge, thirty, forty, fifty years of lending mistakes I know about and didn’t have to make myself because of that time. The time aspect has been really powerful to me, just to put in perspective what it actually costs.

That makes sense. Now let’s move from that mindset starting piece to now you’ve raised this initial fund and now you’ve got to lend it out. You have to figure out underwriting, servicing, investor relations, compliance. Walk us through how you actually lent that first, what was it, forty million in that first raise, and how you actually lent out that 40 million to flippers and value add and everything that you did.

Yes. It’s a lot. Our average loan even still today is like two hundred thousand, two hundred and ten thousand. It’s a lot of volume. You need a team for that to go right. We had to start to create systems and processes. You can no longer do this off the top of your head. In order for other people to come in and keep up with that volume, keep up with demand, make sure servicing is correct, we had to create SOPs. Now in my company there’s this whole back end folder, a data room essentially, on how we do business. How do we talk to investors? We have reports which are like back looking statements, but we also track KPIs which project what we can expect to happen over the next couple weeks, what we can expect over the course of this month, and what we can expect over the course of the year, putting projections out there, not just as goals, but actual actions towards those goals. When it comes to the underwriting, the servicing, the processing of the loans, after the first dozen, when I realized I was sending the same email every time, I said, okay, this has got to go into a template, and I’m going to bring in an assistant. It wasn’t easy. I’ve been through maybe three or four assistants. People come and go for various reasons, they work out, they don’t work out. But it does make it easier when you can onboard someone with solid systems and a book to review, rather than having to start from scratch in live verbal communication all over again.

Exactly. I am very hardcore with everything, that when somebody onboards, we really want to minimize the live verbal communication, the live face to face meetings, for the repetitive stuff, because that’s not scalable. It needs to be a procedure, a recorded video, something that can be repeated again and again, so that if you do have turnover, you have other people coming on and you’re not starting over.

Let’s dive into how you grew a little bit. You’ve got these systems now, you’ve got this data bank, the SOPs, the KPIs. Let’s talk about how you got from the initial raise to where you are now. What was maybe the first role that you hired for that you initially thought only you could do? You were like, I can’t hand this off, I can’t hand this off. Then eventually you did hand it off. Is there something that comes to mind?

Yes, a hundred percent. Handing off the processing was relatively easy because it’s very simple, you have a checklist almost. The systems are the same more or less for the deals. We do the same type of loans, we’re not doing crazy creative loans. But the one thing that I thought only I could do was investor relations. That is not simple. It’s a relationship, you need a lot of emotional awareness and intelligence, and also a bit of sales, and you have to understand the industry because you get these difficult questions. I was convinced, and I still do investor relations, that’s business development, it’s not like I don’t do any investor relations, but the first year it was exclusively me doing investor relations. The second year that I was lending, around January 2025, I brought in an investor relations team, two people who came onto my team, and I had to distill: how can I make this a process? How do I talk to investors? How do I take someone from not knowing me at all to sending a wire to our team? Slowly but surely we created it. I would have them hop on calls with me, then they’d share their takeaways, and we’d take my takeaways and their takeaways and distill them onto a piece of paper. Slowly but surely we created this system. How do these calls work? What are the typical questions that we get? A frequently asked question sheet we created, a flow of how we are supposed to talk to investors. For example, one of the things I tell my team, I meet a lot of people who are ready to invest today because of a referral, because maybe they saw me on stage. There’s a lot of people who are ready, and it’s their first or second time meeting, and they’re ready to invest today. I used to just say, okay, great, let’s do it. But now we actually slow them down. Because we understand the investor psychology from reps, we slow them down and say, look, we want to get to know you first, make sure this is a good fit. That avoids any cold feet, any wishy-washiness. We know all the boxes now that should be checked before someone actually sends that wire. Those processes became very clear, and it was really interesting for me to change investor relations, this whole thing that I thought was magical, into a real system for closing capital, down to the copywriting we send on the first message, to the first call, to the second call, to the follow-up email. All of it now has become a little bit more mathematical, whereas in the beginning I thought no one could do this, this is very hard, this is very advanced, I didn’t think anyone could.

That’s a great example. I love to contrast it with what you said, that the processing was easy to hand off. There are times when something is a relatively set process and we can bring someone into our team, and we can have the SOP ready to go, and they can plug and play. Then as we advance as leaders, as our business advances, we run into these other situations where someone else can step in and help, but we don’t have that system yet. I think of what we have on some of our SOPs, it’s not just a linear checklist, it’s a flow chart, where there can be multiple choices, it can go back and repeat, and everything. I love how it’s a collaborative process, having that new hire who’s observing, seeing things from an outside perspective, and you and them working together to develop that system.

A hundred percent. I think as an entrepreneur who’s trying to scale and formalize, I had a mentor who told me, look, you don’t need to pretend that you have it all figured out. Ask your team what stood out to them. You don’t need to hand them something on a silver platter. I used to have my team review my calls and take notes on things they didn’t know, so I could craft exactly what a new person coming in wouldn’t know. I had imposter syndrome on my first hires, that I had to be perfect for my team. A lot of times now I ask my team, what do you think? What did you think about that? Send me a report on what you took away or what you found most interesting. We’re going into commercial space, so I’m sending them a lot of commercial resources and material, and I say I want you to tell me all the things you didn’t know that you learned, and all the things that stood out to you, so that now I can craft my SOP and my book of material around what a new mind coming into this looks like, rather than what I think they should know about it. That’s been huge, and a big weight off my shoulders, but it also made me lose a little bit of ego. I don’t need to be perfect. I don’t need to pretend that I have it all figured out. These people are trusting me to figure it out, and it’s okay. It’s actually better to ask for their feedback and their opinion a lot of the time. It empowers them too, to feel like they are making decisions and are part of the decision making process.

And the other thing that resonates there is that employees, I think all human beings, one of our top fears is fear of failing. It can be so helpful when you set that expectation, that I’m going to make mistakes, you’re going to make mistakes, we’re all human beings, that’s normal, we’re not going to know the answers every time. It really can make for a much healthier workplace environment.

Yes, a hundred percent. A hundred percent.

Now we’ve talked, you have great wisdom here about growing a team. I’d love to talk about onboarding. When you’re bringing on new team members for whatever role, what is your process for onboarding, so you can get people operating at a high level quickly?

Yeah, this is so good. I’ve hired people in person and virtually, and what I’ve found is that whether you’re in person or virtual, the first two weeks to a month, I try to just spend as much time with the person. I don’t want to be spending time on things that are repetitive, like teaching them something that is a system, but I do think the culture, being engulfed in the culture of who our company is, is so important. Now my team more or less runs, and we have our meetings every week. But in the very beginning, I actually did something called a virtual office, where we would have a Zoom open during business hours, and our team would just come in and hang out, because I wanted new people to get that sense of community, to laugh and tell jokes and say, hey, what’s going on with this, what’s going on with that. I found that was when we were operating at our best. Honestly, talking about it now, we should bring that back. It was such effective communication, almost like having a real office. That was huge, that was really valuable for me, when someone’s coming in, to spend at least two weeks, but I spent sometimes a month, just having an open forum rather than having them shoot me an email or having calls scheduled on the calendar to check in. I would just have office hours, where our team would jump on a Zoom, and everyone’s working. We’re not all talking, but we’re available to each other, we know we’re available to each other. That really helped, as people had random questions that would come up throughout the day. I felt it helped our culture, and helped them feel comfortable casually approaching the team with questions they had.

I love that idea. It’s something I don’t do right now. I have found that when I’ve been in groups that do coworking calls, and in a mastermind or something, they have an hour a week where everybody can hop on, set their goal, and leave their cameras on, and you have that accountability of being there while you work. It’s a little different, but there’s some kind of community that comes from just being present, while you’re doing your individual work, having your cameras on, being on the same Zoom call. It does help create communities. I love that application of it. That’s a new one for me. I like that, Alexis.

That was huge for me as well.

Love it. Now the next question, Alexis, you may not have anything that comes to mind, it’s okay to skip that. I’m curious if there’s a task or decision in your business today that you’d like to hand off. Maybe it’s something that brings your energy down, or it’s tedious, but you haven’t delegated it yet. Is there something that comes to mind?

Yeah, absolutely. That question is easy for me, and it’s the servicing. I still service all of my loans in house, mostly because I want a pulse on what’s going on. Servicing has provided me the opportunity to check in with my borrowers, to check in with my investors. It’s this natural touch point that happens. But I know deep down, if I want to grow this company, I cannot be collecting and sending payments every month. It’s not feasible. I’ll either need to hire a third party or bring in an internal controller. That is the honest answer to that question. It’s a hard one for me. I still have a tug of war in my head. You can probably see it on my face. That one is hard for me.

That’s the reality of business growth and development. There are times when you can see the pros of making a change, outsourcing or something like that, and yet you can also see the con of it too, and we as the business owner have to measure those and figure out the best way forward. That’s tough. There’s a lot of responsibility. It’s not the same as being a W2 employee where you just show up and punch a time card.

Exactly. I think that’s the real thing that happens with entrepreneurship. The level of decision making gets harder. You have to be more and more courageous, more and more strategic. I think those are the character traits and the skills an entrepreneur has to continue to sharpen, because you learn how to lend money, you can lend money forever, you learn how to process a loan, you can process a loan forever, you learn how to do a flip, you can flip forever. But courage and strategy, you never fully master. It’s always a new level of, I need to be more strategic, I need to be more courageous, I need to make decisions better and faster. I do love that part, because I feel like I’m always growing there.

I think that’s where certain people do so well in entrepreneurship. I love how you’re always learning things, and I can relate to that. If you’re not in a situation where you always have the opportunity to learn and grow, you’re probably going to get bored.

Yep, a hundred percent.

So we have to stay challenged to stay engaged. We’ve got a few more questions. I love everything you’ve done with teams and bringing people on so you can grow the business and help more people. What separates a team member who just executes tasks, maybe a B team player, they’re okay, they can check off the box, from one who actually drives results for your fund, those A players? What have you seen as the difference between the B player and the A player?

This is so good. I have a two part answer. The first is, I think you can tell right away, there is some aspect of hiring an A player or a B player that you can tell from their work ethic, from the way they do their work. Is it to the best that they could do it? There’s such a thing as capacity, someone could have the will but not have the skill, so that’s another thing to evaluate. But you can see from the beginning someone’s ability to perform. The second thing that came to mind is I do think there’s an aspect of this that is due to company culture. If you’re not enforcing that proactivity is a core value of your business, how can you expect anyone to be proactive? Everyone’s going to be reactive. One of the core values of my company, we have three core values: integrity, perseverance, and mastery. When I think about mastery, that’s the core value that most likely plays into this question. Mastery means we are always going to try to be the best. That’s a core value I bring people on with, and I say, look, this is how we operate. The question is, we’re pretty good today, but how can we be better tomorrow? We think we’re great, but how can we be greater? Having that be the foundation of a company, it bleeds into everything we do. The people on my team are constantly thinking about what else could be done. It’s a two part answer: you can usually see right away whether this is an A player, a B player, or a C player, and how they operate. But if you place an A player into a culture where they’re punished for forward thinking, where their ideas are not received, where their feedback falls on deaf ears, you can easily turn an A player into a B or C with a bad culture. And maybe you can do the opposite too, you can turn a C player into someone who has initiative, who is proactive, who wants to think ahead and strategize, with a positive culture that encourages that mindset.

I love that, I think that’s a really good point. Which feeds into our last question before we wrap up, Alexis. You mentioned a lot about that culture and how important it is. How do you communicate culture, your expectations, your standards to your team?

We talk about it every week, so we do beat a dead horse, it’s not something that we treat lightly.

It’s a part of every team meeting, like at the beginning?

Usually over the course of the week, at the end of the week we have a review of that week, and we identify what each person did that week to exemplify these characteristics. For example, I had an investor relations team member who did additional research to answer an investor question, and that’s mastery and perseverance. I also had one time, someone sent me an incorrect wire amount, and we sent back what they oversent. That’s integrity, rather than just accepting it and changing the contracts to reflect what they sent. It’s, hey, this is wrong, and we want to make sure we have the correct amounts reflected on our documents. That’s integrity. We talk about the actions of those core values on a regular basis, and I think that helps the team really identify with and get behind how those shape our business.

That’s a really good point, and it has to be explicit like that to really help. Great point, I love it. Now, Alexis, as we wrap up, if people would like to connect and learn more, or have a follow up question, what is the best way for them to reach out to you?

Any platform that’s out there, LinkedIn, Facebook, Instagram, YouTube, all of them, I am at Alexis Morgan Invest. My email is Alexis at peachstatecapital.com. If anyone wants to reach out and has questions, I’m more than happy to help.

Perfect. And if you are listening as you drive, of course all of that is in the show notes, so you can grab it there. Thank you so much, Alexis. There’s a ton of wisdom shared today. I really appreciate you coming and opening up like that. And for our listeners, thank you for listening, and join me again next week.

The post The One Task This Fund Manager Still Won’t Delegate appeared first on Adrienne Green.

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

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

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

Thank you for having me, Adrienne.

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

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

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

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

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

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

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

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

Which is what now has become Host Easy.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

I love that.

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

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

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

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

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

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

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

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

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

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

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

Yes.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Yeah.

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

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

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

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

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

Right, the ego.

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

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

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

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

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

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

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

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

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

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

I love this question.

The first step is always the clarity.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Courtney, you want to take that one?

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

Right, that’s amazing.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Go ahead, Courtney.

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

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

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