How to Build a Real Estate Business That Operates Without You

Samuel Eddinger (00:00)
Which is more human-centric, to try to run and grow a great boutique property management company that allows AI to do the administrative functions and humans to do the human functions. I think there’s going to be significant job loss in the future, and I think that’s gonna have an impact on human psychology and psyche in a significant way. And I think that— the best thing that humans can do in light of this world and this transition to AI is to support other humans, and so that’s what I want to equip and help my team be able to do better.

Meghan Escobar (02:08)
Everyone, hello. Welcome back to Real Estate Pros Podcast. I am your host, Meghan Escobar, and today I am joined by someone who I’ve been looking forward to chatting with. We have Samuel Eddinger, and he is operating in the Connecticut area. He is someone who’s mastered quite a bit in the real estate industry. However, where we’re focusing on is his skill set. Man, which way do I want to go here? Samuel is— let’s say he’s a— he’s a master of many things here, but a master operator in systems, I think, is where we’ll focus on. And he’s got some unique styles of how he operates and in his world. So I’d love to hear a little bit more about that. And you know, it sounds like he’s been making some serious moves also in like the AI world and bringing—

Samuel Eddinger (02:36)
Yeah.

Meghan Escobar (02:58)
—those systems into the real estate world. So we’ll touch on a little bit of that. I think that’s something that a lot of people are interested in to hear about today. Some people are scared of it, some people are embracing it, and some people have no idea where to start with it. So with that being said, I— I think our listeners are really going to be able to take something away on how you are approaching things specifically in that area. So let’s— let’s dive in here, and first off, people may not be familiar with your world. Give us a short version of what your main focus is these days and what— what markets you’re operating in.

Samuel Eddinger (03:36)
Yeah, so we’re— thank you, Meghan, for the introduction. I appreciate that. Yeah, so we’re operating in the Connecticut area. I was born and bred here and grew up here, and really love the Connecticut market. We are a pretty blue state. That means that a lot of the legislature is tenant-friendly, and so that gives us some unique challenges. But we’re in the property management space. I do a lot of real estate investing and flipping as well, but ultimately— I think that property management is a great— a great place to— to become an entrepreneur. You’ve got recurring revenue streams. It’s pretty sticky because ultimately you are able to support owners for years. And you know, while there are unique challenges, I— I feel like I can serve a— a community of people that maybe want to diversify and use real estate as an investment, but don’t want to have to do— deal with all the day-to-day headaches of screening tenants and maintenance requests and security deposit dispositions and things like that. So that’s kind of where I am currently: Connecticut real estate investing, flipping, private money lending, all— all things in the real estate industry. Mm.

Meghan Escobar (04:48)
Awesome. Love that. And so one thing that caught my attention about you and you know the way that you’ve been able to navigate through leadership— I know that was one area that you feel you struggled a little bit in. And maybe a lot of people that are getting into entrepreneurship or real estate, they might struggle with that as well. So what’s one way that you feel like you’ve been able to be a great leader as well as, you know, you understanding the the operating side of and system sides of things?

Samuel Eddinger (06:13)
Yeah, I think that for me, everyone has their own leadership philosophy and style. I’m basically great at systems. I always have. I have an engineering degree and background that I did for a lot of years prior to real estate investing. And so I was always good at that. And I’ve kind of leaned into some of that philosophy as a mechanism to try to lead. So, you know, all great leaders lead by example. And so, you know, we— I’m— while I’m maybe— I’m not as able to really reach out and and personalize every experience with my team, because that’s— that’s a weakness for me, I am able to lead by example, get up early, stay late, really focus on the work, and show them how consistency and routine can actually really be successful— help you to be successful in— in the game that you want to play. Like, that’s how I’ve been so successful is every day focus on just doing a little bit more each and every day and trying to get a little bit better. Whether that’s about reading books— I lead a— I read a lot of books. We read books as a company. Our— the current book that we’re reading is Brian Tracy’s Eat That Frog. And so it’s a— about— yeah, a great book. So we read a lot of books as a team and try to use that as— as— as a method. One of our core values is always improving, and so we’re always trying to improve as a company and we’re always looking to—

Meghan Escobar (07:24)
I just finished that book, great book.

Samuel Eddinger (07:36)
—to find people that live out the core values that we have. And it makes the leadership a little bit easier, right? Because if we’re all— if we’re all focusing on the same set of standards, you know, you can c— you can call people out, you can hold them accountable to those standards that we as a company hold— hold dear to us. So, you know, it’s— it’s definitely a challenge for me. It’s definitely something that I’m continuing to work on. I read a lot of books on leadership— one’s The Coaching Habit. John Maxwell’s one of my favorite authors for— for leadership as well. I have a number of leadership books that I still need to read, but ultimately it’s, you know, it’s finding your own way on how you want to lead because there is no right way to lead. And if you— I think that the point is if you don’t lead from who you really are as a person, it’s never really gonna work. So you gotta kind of find your own leadership style and g— dive headlong into it. And all because you don’t lead like Elon Musk or a Jeff Bezos or a Mark Zuckerberg or whoever a great leader is that you admire, doesn’t mean that your style’s wrong.

Meghan Escobar (08:38)
That’s a really solid piece of advice, and I— I think that a lot of our listeners will be able to resonate with that, or— yeah, I think resonate is the perfect word. Because one thing that you said that was super, super powerful is you need to find your way of leadership. And that’s not going to be anyone else’s way, but most importantly, leading by example. You know, waking up and doing the early mornings and reading the books and doing the body movement and all the things that, you know— most successful people when you talk to— when you ask them and you, you know, get in there and ask, just conversate with them, they’re gonna tell you some of those same standards apply to their world. And you have to be able to show up as that version of the person if you’re expecting someone else to, you know, lead that type of lifestyle.

Samuel Eddinger (09:26)
Your— your team is always watching, and so you for sure have to make sure that you’re setting a standard that’s beyond what they can accomplish easily. If you set a lower standard, that will become the standard of the company.

Meghan Escobar (09:39)
Yeah, agreed. Agreed. And every operator that I know, you know, they— there’s a moment where things got real for them. Maybe that was a deal that went sideways or a time that they had to just pivot really fast. Would you mind, Samuel, sharing one of those moments for you?

Samuel Eddinger (10:30)
Yeah. Some time that I had to pivot really fast. I— I think that one of the things— actually, I guess it was a really good moment in time. I remember that I started growing the company, and my first hire, I was all excited, did the whole interview process, read the book, hiring book Who, and was really excited about this person. And I was in a play with my daughter, and I got an email from him saying, “This is not gonna work. I left my credit card in the desk.” And I— it was really an existential problem. It’s like, am I gonna be able to make this? My first hire quit on day one. Like, am I even ready to be a leader? Am I ready to do all of these things? And— and ultimately, I— I really was at this existential questioning moment in my life. And I said to myself, “Maybe I should just give up.” Right. “Maybe I should just give up.” And at that b— around that time, my brother, who was my partner, said to me, “Sam, I’m gonna give you three options.” One is we can keep— he was fifty percent owner of of the company. One is we can keep that ownership situation the same. Two, you’re unhappy, you’re— you’re not sure of yourself, you got anxiety, this is not healthy for you. Give up and go back into engineering. There’s nothing wrong with that. Or three, he said, “Buy me out. Double down on yourself and buy me out.” And I thought about it for a few days, and I decided to buy him out. And it was the best decision I ever made because I was in this moment of uncertainty about what I wanted to do, where I wanted to go, and he gave me options that gave me the clarity to make a decision on what I truly wanted. That, no, I’m gonna give up and not be an entrepreneur anymore, or I’m gonna double down and be the best entrepreneur I can be, and I’m not gonna have anyone else hanging over my head. Not that he was, but that all of the profit, all the benefits that I got were gonna be uniquely mine to realize for my family. Or we can keep doing it the way we’ve been doing it. So yeah, that was a situation in my life where, you know, I was kinda at this point and I had to make a move pretty quick because being in that uncertainty is never a healthy point. You have to get to a point where you can clearly know where you’re going.

Meghan Escobar (12:51)
Mm-hmm. That is just bringing something up for me, something that you said pro— pre-podcast: if you engineer the life you want, you can have everything. And you also followed up by saying you just need to be really clear on what you want. And I’ve heard this from many mentors of mine, myself, like the universe will provide whatever it is that you believe in, right? So the— the— the higher powers, right, will provide you with everything that you want in life. The problem is most people don’t know what they want or they aren’t very clear. We mentioned clarity quite a few times. That was a really strong— a strong share. I— I— I’ve taken a lot from it and I’m like, I don’t know which way I want to navigate it. But another thing that— that you mentioned in that story was you were at a play with your daughter. You also a father and a family man. You have six children and a wife. How— kind of a couple-fold question here. I got one, I want to know, what was the emotion going through you at that point where you— you felt unclear? And then the second one that you can kind of lean into is how do you navigate, Sam, being a successful businessman as you are with your— your hands in so many different things— 20 properties, 50 units, the— you know, the consulting potential coming— coming in the future, and also being a family man?

Samuel Eddinger (14:19)
Yeah. So to answer your first question about what— where was I in that moment, it was, you know, a lot of questioning, a lot of confusion, a lot of self-doubt. I think any entrepreneur that starts off that doesn’t have a level— you have to have a level of confidence in yourself, but also self-doubt, that whether you can really do it, and and being able to kind of deal with that— the d— you know, the confidence but the questioning, I think it’s really hard. But it’s— it’s really necessary to— to get to the next levels. One of the things that I do naturally is I use anxiety as a tool to help determine where I should focus my attention. So anxiety in and of itself is— can be debilitating, but it’s— I believe all emotions are blessings. And so what anxiety is really saying is, “You should pay attention here. There’s something here.” And so I don’t like to be anxious, and so I use that as a vehicle to say, let me fix my company in these ways. Right. So maybe this— this insight of this guy quitting was, you really need to focus better on being a better leadership leader, or you need to be X, Y, Z, whatever it is. So that’s kind of what I was feeling in that moment.

Meghan Escobar (16:16)
How were you able to navigate through life being such a successful businessman and having so many responsibilities on the business aspect side of things, but also prioritizing family?

Samuel Eddinger (16:27)
Yeah. So a lot of it is, and I would say that being an entrepreneur gave me more freedom to do the family thing better, even though a lot of entrepreneurs work a lot of hours. What it allowed— so one of the big things, and I see in the back of your bookshelf, Traction. So one of the things that we did was implemented EOS into our company, and so I’ve always focused on, how do I get out of the day-to-day? And the way that I do that is by building teams— building systems and building teams. We have a team of t— about twelve people for two hundred and something units. Anyone that saw this would say, “Wow, you have way too many people.” But it allows me to really focus on trying to become an— a CEO-type person, do leadership development, not have to get into the day-to-day. We’ve had a number of issues recently with a scammer who essentially, fraudulently, got access to some systems that we utilize and was able to scam people out of money. And I didn’t really have to get that heavily involved because I have a team around me that can do it. So a lot of these really kind of hairy situations I’m able to stay insulated from. And that gives me the ability to really focus on those higher tasks— you know, be it the culture of the company, be it the leadership development of the team, be it the systems and what we’re doing as a company, be it with AI or— or other things. And it gives me the autonomy to— to be on podcasts and things like this and not have to worry about what’s going to happen today. And this freedom and flexibility allows me to do things like go home early if I want to or not. We did a six-week cross-country trip across America two summers ago. You know, so we designed a life that we wanted to have. And had I been working, you know, for a regular company as I did historically, that’s— those type of experiences are way less likely because I’d be limited by the amount of vacation I have, as an example. And so really, like, when I design my life, it’s really more about, how do I design something so that I have the autonomy to go take off on a moment’s notice on a vacation? I can do that, right, because I have a team, and in property management, I don’t have to be hyperlocal. So I can bring my computer if I need to, but I don’t have to. And so a lot of it is just seeing other people have done the things that you want to do, like taking a six-week trip across the country or, you know, not really being part of your company for a month or whatever it is, and then leaning into it. I think when you do it, and even if you do it unsuccessfully, it shows a lot of weaknesses in your company. And that six-week trip across the country really showed me that my company could operate without me. But it could not grow without me. Right. And there really wasn’t growth of the company. Yeah. And that’s okay. Right. Like, it’s a good understanding. Okay, I don’t really have a company that can become better without me. How do I go about and work on training and building systems and people so that I can actually get to that level? And that’s much harder, but that’s kind of the work that I’m working on now.

Meghan Escobar (19:30)
That’s beautiful. And I think that’s the kind of stuff that most people don’t talk about, right? Like, what separates the folks who are just here to dabble a little bit and make some transactional sales or whatever it is versus the ones who are here to stay in the game long-term. So you have clearly— clearly done the work to— to prove that this is something that is— is— a is— is a long-term thing for you, and how do you— how do you create these systems that can help the business run and grow at the same time? So that’s— that’s incredible. What do you feel like, with you kind of ending with that, “That’s what I’m working on now,” what is that focus for you on the next big goal or the next scale movement for you?

Samuel Eddinger (20:16)
Yeah, so i would say there’s two. One is my daughter and my family and coming into the business. What does that look like? Like, I don’t believe in nepotism. And so— but I also recognize that if my children want to take over the business, like I want to allow and encourage them to be able to do that if they want. So my daughter just turned 18 recently and she joined the business about a year ago. And— and so she is exploring if that’s something that she wants. And I don’t push her to do that. I encourage her if she wants to, but I’ve realized that you can’t make— it’s— it— unhealthy and unhelpful to make someone do something that they don’t want to do out of compulsion. So that’s one thing we’re focusing on. I’m gonna be staying in the business somewhere between eight and twelve more years, and we’re gonna be working on a tran— a transition plan if any of my children decide that they want to be in the business. That’s one thing. More— more closer, we’re looking at AI in a significant way to transform our company. So ultimately, I recognize there’s— there’s— there’s a mentality that says, “If you had to start over, what would you do differently?” Right. So if you— if you took yourself into this little mental experiment and said you sold your company or you did something like that and you decided that you wanted to start over, what would you do the same and what you would— would you do differently? And I think we’re on this precipice of AI where it can do so much— that so much that thing so much naturally that people had to do manually. And I think that there’s a lot of really cool things that you can do to make the people experience better. And so we’re really focusing for the next twelve to twenty-four months. We’re gonna be completely changing our company, all of our systems, all of our software, with a different focus. It is more human-centric, to try to run and grow a great boutique property management company that allows AI to do the administrative functions and humans to do the human functions. I think there’s going to be significant job loss in the future, and I think that’s gonna have an impact on human psychology and psyche in a significant way. And I think that— the best thing that humans can do in light of this world and this transition to AI is to support other humans, and so that’s what I want to equip and help my team be able to do better. And there’s a lot of things we can talk about it if you want specifics. But I think to me, that’s where I’m going in the next 12 to 24 months is revital— sorry, second time, revamp—

Meghan Escobar (22:50)
If I— if I—

Samuel Eddinger (22:52)
So revamp the company to be able to— to be able to do that better. And so that’s— that’s kind of where the— the AI— where I am with the AI is not to use it as a mechanism to re— remove people, but to enhance their ability to do human things.

Meghan Escobar (23:08)
And I think that’s an incredible perspective to put on it because, you know, so many people— conversations that I have had that have never touched AI because they’re so afraid of that concept of, “It can replace me.” It— it— whatever that is, it’s like they’re just scared of it. And the truth is it’s here, right? It’s not— it’s not going anywhere. And so, just like you stated, you know, if you engineer the life you want, you can have everything. You— and then fear, you know, fear comes up in every aspect— being fearful of this system, this— this thing that’s out there, this artificial intelligence. You can fear it, right? Or the anxiety that might come up around it, you know, like you mentioned, you use that as a— as a— as a fuel for you, right? That’s a fuel for you to figure out, okay, what is this come— why is this? Why am I anxious around this? And I think so many people are scared of that— that emotion that comes up around things that are unknown. What is one piece of advice that you might— might give somebody that might feel those type of emotions— the fear, the anxiety around a system like this?

Samuel Eddinger (24:16)
Yeah. I— for me, I think that there’s— there’s a lot of teachings about while history doesn’t repeat itself, it rhymes. And so there’s— there’s stories about some people called the Luddites, and they basically were people that resisted the Industrial Revolution. And so I— I think that— and there’s plenty of other experiences of what happens in light of transformational change. For me, it starts with an acceptance. Right. You— you have to accept that this is going to happen. And and what I believe is we’re currently at the precipice of a transformation where intelligence doesn’t matter anymore. And I used to really put a lot of focus on intelligence. Right. I’m— has historically been told throughout my life that I’m one of the most intelligent person— people have met. And now I recognize that intelligence doesn’t really matter in light of AI because AI is more intelligent than no mob— Nobel Prize-winning people. What matters now is the ability to adapt and be flexible to a changing world. And so the— the truth of the situation is for you to survive whatever is to come, as long as you can adapt and be flexible and work on those things to adapt and be flexible, like, you’re gonna be fine in the future world, whatever it may be. And so I’m really leaning into that a lot. Like, I— like, there’s plenty of professions within property management that don’t really talk to people. And so if those professions, like accounting, don’t learn AI and learn how to leverage it as a tool to help make them better, those people are not gonna be needed in the future world. And so learning how to adapt, how to leverage the tools, how to be able to use it as a method to become more productive is exactly what every person needs to do to be employable in this future world. And so we’re actually reshaping our company as well. And any people that don’t have significant levels of adaptability and flexibility, they’re not going to make it in our company. And I’m trying to encourage and teach them and upskill them, but ultimately— this is— this is— this is happening. And it’s— it’s a challenge for me as well, right? Like, it’s— so don’t get— don’t make this seem like, he’s just good at it. No. You know, I’m— I’m in therapy, right? I talk to therapists all the time. It’s cognitive behavioral therapy, right? So all it is is make a small change, just go into it, go into the fear, small baby steps. And next thing you know, if you do it, you’re gonna be like so many other people that are addicted, going down the rabbit hole, building great systems that they’re like, “Wow, I never knew I could build a XYZ system, right?” And you can build some amazing things. And then you’re less fearful of it. So, you know, just go into it, take the anxiety as a— as a tool, and just little by little, just do some fun things with it.

Meghan Escobar (27:07)
Yeah, Atomic Habits. And I know a lot of people listening, you know, most of our listeners are very early in the journey of maybe not sure where to dip their toes in when it comes to real estate or becoming an agent or builder, an investor, whatever it is, or— or we have veterans in the game who are—

Samuel Eddinger (27:09)
Yep, atomic habits.

Meghan Escobar (27:31)
—looking to level up or maybe learning how to utilize the new world and the AI systems and and all of that. but I think they’d benefit from hearing this, you know, when it comes to building relationships, you talked about human connection a lot and how to embrace that and how to— how to, you know, bring AI into human connection and and make them both better, right? And growing your network. What has made the biggest difference for you when it comes to building relationships in this space?

Samuel Eddinger (27:58)
I think for me it’s— and it goes back to a lot of just who I am as a person, it’s about consistency. Right? What happens is, you know, go to the meetups, have a community of people that you agree with, find people that are better than you and ask them if you can take them out for lunch or do a mastermind or— or something. find a community of people like you, but— but stay consistent with them. The— the truth of the situation is I get it— I get told all the time, “Hey, I’m really passionate about real estate.” And I tell these people every single time, “Hey, reach out to me anytime. I’d love to continue to give you advice and to provide value to you whenever possible.” And the truth of the situation is almost no one does. And that’s why I can go ahead and do that, because human nature says people have great intentions and poor execution, right? They intend to make this great life of real estate and things like that, but the vast majority of them like the idea of it, but they are not willing to put in the work. So I think that, you know, putting in the work always with the relationships that you have, going to meetups, talking to people about it, you know, figuring out where you want to play in this game— you can make money in so many different parts of real estate. Like, I probably make money in five or six different parts, right? And there’s so many ways to make a lot of money. I have a lot of friends that have made a lot of money in real estate, but they’re the ones that you see consistently showing up at activities and meetups and just doing it for months and years and decades. And so this is not a get-rich-quick game. This is a get-rich-slow game. So the relationships that you build are really based on that level of consistency. And if you stay consistent and you stay in the game and you go out, you’re gonna make great relationships that will turn into partnerships that will allow you to find op— allow you— allow you to essentially amplify and magnify your reach through other people’s reach. So that would be my advice to anyone starting is— is don’t think that you’re gonna get rich fast. You’re gonna get rich slow, and it’s really about leveraging and networking the relationships over decades.

Meghan Escobar (30:03)
Mm, yeah. That’s— lot of truth in there. And you know, one thing that cannot be faked is relationships in this space. So important. So so important. The— the people you know, you know— you hear— I’ve read many books as well and have mentors, and the thing is I hear consistently is your network is your net worth. People you surround yourself with are— are really going to dictate, you know, how you live your lifestyle and the habits that you create. So thank you for sharing that. Now, Sam, if somebody took value from this after listening and they wanted to reach out to you or collaborate and learn more about what you’re doing, what is the best way for someone to reach out to you?

Samuel Eddinger (30:47)
Yeah, so you can call me or you can email me. So my phone number is (860) 254-7343. (860) 254-7343 Leave a message. I screen all my calls. I’m in property management, so I don’t really want to talk to tenants if I don’t have to. and then my email is Sam, S-A-M, at ironcladpm.com. I-r-o-n-c-l-a-d-p as in Peter, m as in Mary dot com ([email protected]). And again, like, send me an email and I’m— I’d be happy to— to respond. Just make sure your email is not like a solicitation because I have AI that basically screens those out.

Meghan Escobar (31:27)
Perfect. Perfect. Well listen, I appreciate your time, your story, and more— most importantly, your perspective on what you’re bringing to the table here with the human connection and and the systems and all the things, the leadership. We most— we need more people in this space who are doing things the right way. And so thank you again so much for being here, Sam. And for those of you that are tuning in, if you got any value from this, make sure you do subscribe. We’ve got more conversations with operators just like Sam here who are out here building real businesses, real relationships in real time. So we’ll see you on the next episode.