At the beginning of a real estate investing journey, there’s a lot of necessary exploration. We are learning and trying out lots of new ideas, approaches, strategies and more. But ultimately, if we want to make meaningful progress in our real estate investing endeavors, we need to settle into an investing approach that we can replicate over and over again—that’s when we get the most traction and make the most progress. In this episode, Jeff shares a seldom-discussed key aspect of finding that sweet spot that will create the most possible traction: adopting a strategy that is at the intersection of the head and the heart.
You know, it’s safe to say whether we’ve been doing this for five days or five decades. We’re all on a journey, right? We’re all kind of finding our own way, and finding our path. And really, I think what we’re ultimately trying to do is we’re kind of finding our thing, like what is our own little corner of this giant universe real estate investing, to find the thing that is really ours. And once we find it, then we can get a lot of traction. And in today’s episode, I want to talk with you about what I truly believe and have experienced, witnessed and others to be the number one most important thing to get you to a place where you can achieve massive traction in your real estate investing journey. So Let’s cue up the theme song. We’ll jump right into this important conversation.
Welcome to Racking Up Rentals, a show about how regular people, those of us without huge war chest of capital or insider connections, can build lasting wealth acquiring a portfolio of buy and hold real estate. But we don’t just go mainstream looking at what’s on the market and asking banks for loans, nor are we posting We Buy Houses signs are just looking for “motivated sellers” to make lowball offers to. You see, we are people-oriented deal makers, we sit down directly with sellers to work out win-win deals without agents or any other obstacles, and buy properties nobody else even knows are for sale. I’m Jeff from the Thoughtful Real Estate Entrepreneur. If you’re the kind of real estate investor who wants long term wealth, not get rich quick gimmicks or pictures of yourself holding fat checks on social media, this show is for you. Join me and quietly become the wealthiest person on your block. Now let’s go rack up a rental portfolio.
Hey, thank you for joining me for another episode of Racking up Rentals show notes for this episode can be found at thoughtfulre.com/e187. Please do us a big favor by hitting that follow or subscribe button in your podcast app. It really helps, of course, you to make sure you don’t miss any episodes, which we don’t want that to happen. But it also sends the message back to those podcast platforms that you’re listening. And it makes them want to promote our show to other fellow thoughtful real estate entrepreneurs, like you. So thank you so much for doing that.
Onward with today’s episode. You know, when I first got started in real estate investing, it was, what 17-18 years ago or so. I had purchased my own primary residence before that. And that was a very traditional process. I even worked at a bank. And so I worked with that bank for the financing of that house, a primary residence and we had a real estate agent who happened to be my mother in law as well. When we went to buy our first rental property, three, four years later, we took the same approach. And it was a very conventional and traditional way to buy a piece of real estate. And at the time, I thought that was the only way to do them. And now looking back on it, I realized that there are other ways. But there was sort of that initial segment of my real estate investing journey felt logical, it seemed to make sense. It didn’t feel good or bad, necessarily. I guess I was glad that I was doing it overall. But it did feel like it was probably kind of slow. And it kind of felt sort of arm’s length just sort of sitting behind the desk and sending emails and making phone calls and never talking to anybody and things like that. So that was my first point of reference.
As I started to get more excited about real estate investing, I started learning other new things. I started learning about topics like wholesaling, and flipping houses and different sources of money and different ways to try to buy properties and the ideas of trying to get big discounts on properties and make cash offers and those types of things. I went to a couple conferences. Now I would look back on these and say there’s a very cheesy sort of gimmicky conferences, but I went to those conferences, and I came home and I applied what I was learning and was trying to do some wholesaling and did just a little tiny bit of that bought a property and resold it to somebody else. And when I did that segment of my real estate investing journey, I thought to myself, you know, this kind of makes sense. I can see how this would work. But this really does not feel like me. Maybe you’ve heard me say before that at one part in this segment of my journey, we bought some bandit signs and put up some bandit signs. And I had to put up the bandit signs in the middle of the night because it was dark because I didn’t want anybody seeing me do it. And it probably wasn’t legal to be posting these things on phone poles anyway. And it was all about creating, you know, Google voice phone numbers so that nobody would really know who I was in a cheesy cash buyers website kind of a thing. And well, all I knew there is, that while I could see why this would work and it had been explained at these conferences and podcasts and things like that why this would work, I knew it did not feel like me. And that felt like a real disconnect. And then when I moved on to kind of the the third segment of what I was trying to do, because in my mind, I’m kind of over the course of these couple years, I was stumbling around in the dark, trying to find something that seemed like it was the right thing for me to be doing. So I was sampling a lot of different things.
And so the next segment was one in which I wasn’t doing the cheesy gimmicky marketing, but I was connecting with sellers, and then I was having real conversations with them. And we were getting along well, and it felt good. But I wasn’t getting deals done still. Because every situation and each person I would talk to, they had a different scenario and different needs. And all I really kind of knew was like, gosh, I guess you buy a property at a huge discount. And that’s how you make it work. But I wasn’t finding those opportunities, but I was connecting with the people. And so when I was in this segment, I was thinking to myself, gosh, this feels good. To me, this really does feel like who I am. And I liked the way I’m interacting with these people. But it’s not working per se, because I’m not actually getting any deals done. I’m sort of lacking what it takes to get the deals done. But the methodology feels good, it just isn’t functioning quite correctly yet. And it was only after I met my own coach, then it moving into the fourth segment, which I’m now you know, many decade or so into thankfully, that I found something that was an approach that really, really worked, and really, really felt good. And it was at that point that I started to realize, and I’ve become more conscious of this.
These last few years as I’ve been a coach, I get to see other people and how their journey goes, I started to realize this simple, simple truth. That traction happens for us in our real estate investing journey in our endeavors, when we find ourselves doing business at the intersection of our head and our heart. In other words, we are doing business in a way that makes sense to our heads. So we have the functional part of it that it’s actually working effectively. And we’re doing it in a way that feels right to our hearts, because then it feels authentic to who we are. I want to dive into the head and the heart a little bit and just break each one of these downs so that you know exactly what I mean. And then we’re going to talk about what happens when you’re not at the intersection of the head and the heart, just as I was in the first three variations of how I was trying to do real estate investing, until I found the fourth one that really truly was at that intersection. So the intersection of the head and the heart is going to be different for each person.
If you are listening to this podcast, if you’ve been listening to this podcast for a while and you’re coming back, there’s a chance, I think there’s a real good chance, that the intersection of the head and the heart for you might be similar to the intersection of the head and the heart for me. But there are other people who are probably not members of the thoughtful real estate entrepreneur community whose intersection of head and heart is in a completely different spot. And I think that’s okay. But what I think is most important as we all seek to find that intersection of head and heart. So let’s talk about the head.
The head is, not surprisingly, the logical side of this equation. It’s really the functional kind of side of this equation. Is the strategy I’m employing actually working? Is it likely to get me where I’m trying to go? Right, if my goal is to make $500,000 a year in cash, then, you know, flipping might be the vehicle that’s most suited to get me there. Whereas if my goal is to have 10 or $15,000 a month of passive cash flow in, the vehicle to try to get me there’s probably going to be more about rentals and things like that. So the question with the head is, is the strategy that I’m trying to use here, is it actually working or is it likely to accomplish what I’m trying to accomplish? Right? And we all know that there are 80 billion different ways to do real estate investing, right? There’s, you can slice and dice it in so many different ways. There’s a residential, million versions of residential investing, million versions of commercial investing. There’s not even owning properties but just lease optioning them or, I hear people talk these days, about rental arbitrage where they’re just renting a property and subletting it out to somebody else in some manner. You can take any of these and apply them to long term rentals. You can take any of these and apply them to short term rentals. You could take a triple net, commercial industrial real estate kind of approach with these. You could do flips. You could do wholesaling. You could buy properties on lease options. You could do anything. And we all know, because we’ve all seen so many different books, and so many different types of podcasts, and so many different sessions at conferences and topics, that there’s so many ways to do it that that by itself is frankly, quite overwhelming.
You could add into this head section, what is your sort of approach to financing? Are you going to be strictly conventional in the residential sets? Are you going to be not just doing residential but sticking to banks only? With other things like commercial deals? Are you going to say I’m going to focus on being a great hard money borrower and having recurring hard money relationships? Or recurring private money? Relationships? Would you be like me? And then say, ultimately, I’m going to focus on seller financing? Specifically, as much as possible? Am I going to be a cash buyer? What’s my attitude and mentality around debt and the purpose and role of debt? And how does that influence my financing strategies? But the head is all about the logical side of this. Does this way of real estate investing work? For me? And what I’m trying to accomplish? Does it make sense? Can I see how if I do this thing, over time, it’s gonna get me where I’m trying to go. So all of this is happening above your shoulders, so to speak. This is your you using your brain to decide rationally and logically if the strategy you are trying to employ is the one that’s going to work to get you where you’re trying to go.
But let’s shift and talk about the heart side of this too. Now, again, just to kind of a little disclaimer, I think if you’re the kind of person who’s listening to this podcast, and maybe you’ve listened to previous episodes, you’re probably inclined to be willing to think about these kinds of things. But if it’s your first time listening, then you might think that this sounds really touchy feely. And I actually want to say, I don’t think it’s really very touchy feely at all, I think this is very, very realistic. Because every single one of us listening to this is a human being. And whether we like to acknowledge that we have feelings and emotions and how those feelings or emotions impact what we do or not, it’s true that those things actually happen. So what is the heart side of this? Well, I would say the heart side of this is simply put, how it feels to you when you’re doing the thing you’re doing when you’re doing the thing that your head says will work or should work. How do you feel when you’re in the process of actually doing that? This is the emotional experience that you’re having as you do it.
Now it could be a conscious emotional experience it is such that you feel it and you can tell right there in the moment, how it’s making you feel but it could also be subconscious as well and then we’ll talk in a minute about what happens if your subconscious is not feeling good on the heart side. And how that can impact you. Is this way of doing business a good fit for you? Does it match how you see yourself I will just give you the dead simple example is it when I put up the bandit signs during that little chapter of my you know process of wandering through the woods trying to find the strategy that worked for me. I felt very uncomfortable because this idea of being somebody who had to put up a sign in the middle of the night did not align with how I saw myself. I saw myself much more as kind of a good citizen rule follower kind of person. I was a good student, kind of a follow the rules not a renegade rogue kind of person. Not this felt a little bit underbelly ish to me, that did not align with how I saw myself but my head said, this makes sense, Jeff, keep doing it. So I forced myself to do it. Even though in the moment, it was real obvious to me that it didn’t feel like who I was. I often have joked that I felt like every time I did something in this strategy, I felt like I needed to take a shower afterwards.
Another important part of the heart is does it fit with what you’re doing? Does it fit with your own talents, and gifts? Is it really capturing who you are? Is it harnessing what you are best at? It took me a long time to see and thankfully through the help of a lot of coaching from my coach Greg to help me see that the number one thing that I do best is just develop rapport with somebody sitting in their living room that people tended to feel comfortable with me. And that we could develop likability between us quickly and easily in that any strategy I would employ that didn’t center around that was ludicrous because that was the best thing that I was able to do. And when I was doing that, I actually always felt like I was being authentic to who I was. I think an important question is, do you feel proud of what you’re doing and yourself? For doing it as you do it? And shortly thereafter? So I mean, some examples of things related to the heart side of things. How are you meeting with and interacting with sellers? Or are you not ever meeting and interacting with sellers? But instead, you’re meeting and interacting with real estate brokers? How are these negotiations conducted? Do they all happen in the same day real quickly, coming to a cash offer that says, accept us? Or don’t accept this here today? Is it a longer kind of protracted drawn out? Negotiation over time? Is it about you interacting with people who you perceive to have motivation? Or people who you think would be motivated, but it’s not easy to tell yet? How do you create value in these situations? Like how do you feel good that the other person is being well served at the end of this? How do you feel about your brand, and I don’t necessarily mean your logo and things like that. But like your reputation, how you are perceived in the market, if you did this for five years, and you built up a reputation in the community? Are you comfortable with that reputation and how people perceive you, as a result of how you have done business. So these are all the elements of the heart side of things.
So the head is very logical, it’s like this is the functional strategy I’m using to get where I’m trying to go. And then the heart is more about, here’s how I go about it, here’s the flavor of the style, the spirit with which I do and execute the strategy. And I would say together the head in the heart, create your strategy, right. And it’s been very clear to me now for several years that the intersection of my head and hearts that I have landed on is that I am all about owning properties for primarily the long term, long term rental investing quality properties in good locations. That’s a part of what I do that makes that feels right to me, and makes sense on a logical sense for what I’m trying to accomplish in my portfolio. And I only ever buy properties directly from sellers not listed properties, because that just doesn’t really fit who I am. And it puts my greatest talents on the bench instead of in the game where they need to be. And I do that direct buying with sellers in a very relationship oriented manner. And I don’t rush the negotiations, and I just develop rapport with people. And that is central to how I do it. And so my strategy is the intersection of the strategy that works for me, which involves sophisticated seller financing and great properties in a manner heart that is relational. And people oriented, more than transactional and more than property oriented.
Now, that’s my intersection. And that’s great. And you’re probably not surprised to hear that if you’ve been a listener of the show, your intersection does not have to exactly be the same as that. But it is critical that you find that intersection.
So let’s wrap this up by talking about the reason why it’s so important that you find that intersection. Let’s talk about what happens if you don’t find that intersection. If you don’t find that intersection, and you’re doing something that feels right to only your head, or feels right to only your heart, you will always be limited. To go back to my example. Right? When I was first getting started that chapter, where I was putting up the bandit signs and had the buyers website and all that. It felt right to my head. It made sense to my head logically, and people had explained on the podcast and conferences and all that books. Here’s why this makes sense. Here’s how you can buy real estate and make money. It made sense to my head, but it did not feel right to my heart because it didn’t feel like it was authentic to me. So what happens in a case like that, what happens is usually subtle, if not obvious, self sabotage. Because you’re trying to do something that you also subconsciously deep down maybe even consciously know isn’t really the right thing for you to do but your head keeps override. Didn’t you say Nope, it’s okay that it doesn’t feel right. It doesn’t matter that doesn’t feel right. This is all about the numbers, keep going, keep going, keep going, and doing things that don’t feel right to you. But the exact opposite can happen as well, in that next segment of my, of my journey when I was connecting with people in the right way, and having the right kinds of conversations with them, and developing trust and rapport, but I still wasn’t getting deals done. It’s because I had, I was in the sweet spot of my heart, but I was not in the sweet spot with my head. Because I didn’t have the sort of toolbox to know how to get deals done on a practical level, that were matching those types of conversations that I was having the conversations felt really, really good, but I didn’t know how on a real technical, tactical, practical, you know, type of way to get a piece of real estate bought, and in a way that would create profit for me in those scenarios. And so that, you know, I felt good, but I was very, very discouraged, because I wasn’t getting the results.
So when you have, you know, your head is working, but your heart is not working, you start to experience some self sabotage, oftentimes, but when your heart is working in your head isn’t working. And it’s not making sense on that level, you can feel good about what you’re doing, but feel very discouraged very quickly. So my friends, what I wish for you is that your journey, and wherever you are on that journey, I think you we’re all experiencing this, whether we’ve been doing it for just a short period of time or a longer period of time, we’re all always navigating more and more and more towards and into the pocket of that sweet spot. And my hope for you is that ideally, sooner than later in your overall journey, you land at this intersection of your head and your heart. Because I know from my own personal experience, and from witnessing now as a coach lots of other people that when you find that spot where your strategy for how you are doing real estate investing, matches with the the tone and the spirit and the style that feels honest to goodness like you and feels authentic to you and genuine to you, then you’re truly being yourself, and you’re being yourself in a way that’s doing stuff that actually works. And that’s when you will get tremendous traction in your real estate investing endeavors. And that’s what I want for you.
That is it for today’s episode of Racking Up Rentals. Again, show notes for today’s episode are at www.thoughtfulre.com/e187. Please do us a big favor by hitting that subscribe button would be so appreciated. And if you would rate and review this show just real quickly, doesn’t have to be long or eloquent. Just a rating there and a couple words would be super, super helpful and very appreciated.
Did you know that we have a Facebook group for Thoughtful Real Estate Entrepreneurs too? We do and you should be a part of it. It’s called Rental Portfolio Wealth Builders and we would love to have you join us there. Just go to group.thoughtfulre.com and you will be taken right to that page we can hit the Join button. If you liked this episode, please take a screenshot of that and post it to Instagram and tag us; we are @thoughtfulrealestate. I will see you in the next episode. Until then, this is Jeff from the Thoughtful Real Estate Entrepreneur signing off.
Thanks for listening to Racking Up Rentals where we build long term wealth by being win-win dealmakers. Remember: solve the person to unlock the deal and solve the financing to unlock the profits.