Keith Gillispie: Why Most New Investors Fail & How to Avoid the Common Traps #250 | SaaS District

In this SaaS District podcast episode, host Akeel Jabber interviews Keith Gillespie, founder of REI Automated, about the common pitfalls that cause new real‑estate investors to fail and how to avoid them. Gillespie shares his personal journey from Marine Corps service to real‑estate entrepreneurship, describing how a lack of time and chaotic, non‑systemized operations led him to create REI Automated—a suite of software, education, and support designed to automate and standardize the investing process. He explains how external forces (market cycles, interest‑rate swings, new legislation, AI and automation) have reshaped the industry, and why internal factors—discipline, mindset, avoiding shiny‑object syndrome, and focusing on a single core constraint—are critical for success. Gillespie outlines a four‑factor deal‑structuring framework (seller need, personal need, business need, market use) and promotes creative financing methods (seller financing, subject‑to, DSCR, private lenders). He stresses the importance of getting the deal first, then building processes, and warns against over‑investing in tools before revenue is generated. Hiring challenges, the need for disciplined team members, and the value of mentorship are discussed. He recommends three key resources (Rich Dad Poor Dad, Stephen Covey’s 7 Habits, and his own free deal‑structure courses) and shares his core values—keeping the most important thing most important and living an exemplary life. The episode concludes with practical advice for new investors, contact information for REI Automated, and a call to action for listeners.
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Hello, hello everyone. This is your host, Akhil Jabbar, and welcome back to another episode of SaaS District. In today's episode, we'll be talking about why do most new investors fail and how to avoid some of these common traps. Today we have our guest Keith Gillespie joining us. Keith is the founder of REI Automated, which is a platform that helps real estate investors build businesses powered by systems instead of constant chaos as we're seeing today in the world. He has helped hundreds of investors close more deals, generate millions in equity, and create true operational freedom through automation using a practical approach grounded in real-world experience, which we'll share about today. So welcome to the show, Keith. Super excited to have you on.
Thank you, brother. What an honor. Appreciate you bringing me on today.
Thank you. Thank you, Keith. I know you have tons of experience, great background. You know, we're here teaching investors who are listening in. They want to learn how can they build, you know, their own real estate empire, their own real estate investment business. If you can share just a little bit before I get into that, a bit about your background and some are maybe some, what are some of the early struggles or mistakes that you made early on that helped you shape how you invest today?
It's the same for me as it is for everybody. It's the single most important asset in life. And it's one of the shortest words in the English language, just 4 letters, time. I had a lack of time. So, I'll take you all the way back to 2016. Actually, yeah, we'll take you all the way back to '16. I got back home from overseas. I was active duty in the Marine Corps at that time, and I had gotten back home. My wife opened the door. She said, honey, I need you to close your eyes. And I'm like, why do I have to close my eyes? You know, like, I haven't seen you in so long. I just want to, you know, give you a hug, right? And so, she had me close my eyes. I walked through the door. I dropped my sea bags and I opened the door. And, she goes, go ahead and look up and hold out both your hands. And so, I'm looking up and I'm holding out both my hands like this and she's recording this. This video is up on YouTube if anybody wants to watch it.
Okay.
And, she places this round cylindrical thing in my hand and she goes, go ahead and feel this and tell me what it is. So, I'm feeling it. And, you know, my brain goes to, this feels like a pipe bomb, you know, like Marine Corps thing. I don't know. And so I go, it's not going to explode, is it? And she goes, no, I don't think so. And so I'm feeling around for a little bit more. And she says, you can open your eyes. And I looked down and there was a baby bottle with a positive pregnancy test on the inside. And then I look at her and realize she's been pregnant this whole time.
Wow.
That I've been gone, and she didn't want to tell me. She never told me once. She wanted to wait till I got home to tell me in person. And so fortunately, I was there for the birth of our daughter, and and quite literally the very next month I was back overseas, and I came home nine months or not even nine months later. But she surprised me again, same exact thing except this time it was in a plastic bag and she was giving me a cookie. It's also recorded. It's also on YouTube. But she was. She got pregnant a second time and I had missed her trimesters again. And I'm like, dude, I have just freaking failed my wife 2 times in a row and I wasn't there for the pregnancies. And so, 2016, I was like, I've got to make something different. I love the Marine Corps. I was in for 8 years. I won't say a word against it. I had such a wonderful time and I learned so much. However, it was taking me away from my family.
Mm-hmm.
And it was good only for a season. And for the next 2 years, I went overseas and in total I was overseas 13 times. And each time I came home, my wife had to reintroduce me to my own children because they didn't know who I was. And that was really hard for me. So, so real estate, we got started in real estate in 2016, and that was my avenue out. That was my vehicle out of the Marine Corps and into self-employment, entrepreneurship, business ownership. And my gosh, it was so hard because I didn't have time. A lot of people, they have a 9-to-5 W-2 job. Well, the Marine Corps is not a 9-to-5 W-2 job. It's a lifestyle. Like, you're bringing work home with you. You're going over 24 hours at a time that you're working. And so we invested from 2016 to 2020. I was kind of just floundering, finding my footing. We were doing a lot of wholesales and fix and flips, but it wasn't until 2020 that I really feel like I had systemized the business. And that was really the birth of REI Automated of now like, hey, we've systemized this. We've built our own software and it's really freaking good. And my mentor was like, Keith, it's kind of a jerk move to hold this close to your chest. You should provide this to other people. REI Automated was never meant to be commercialized aspect to sell to people. It was just my solution to my problem so that I could get out of the Marines and come home to my family. And so really it was my mentor's prodding that was like, bro, you need to get this out into the world. So in 2021 is when we formally started REI Automated and I started coaching people and educating them on how to do real estate and then also providing that software Whether it be a lead generation software or CRM software or scripting or deal analysis software or whatever, we have tons of software. And then later on, a couple of years later, we bolted on a support pillar as well. So now it's education, software, and support where we're now coaching and mentoring and people get like a client success manager and a developer and executive assistant, things like this in order to help them as they get their footing. Because that's what I want to be, the person in the company that I wish I had 10 years ago when I got started, you know. So that's kind of, that's the story. That's the evolution in, I guess, 5 minutes or so.
So maybe going back to, you know, 10 years ago to today, right now we're in 2026, you know, March 3rd. So when you started years ago without that system that you have, and now 10 years later, what would you say has changed? You know, how you think of investing? What has changed in the game and the market of real estate? And how is this tool maybe helping you become a better investor?
There's a couple of things that I'll bring up. One of them is internal and one of them is external. When it comes to— let's go, let's start external and then work our way in. So external, the landscape of real estate investing is completely different. Like we have, these 10 years have absolutely been shattering to people because things have progressed and we've had so many weird Things happen like COVID, for example, and interest rates plummeting and people are overbuying, you know, $60,000, $80,000, $100,000. They're bidding up these houses in '21, '22, '23, and then interest rates like got really high and it's a stale market. There's all these laws coming out against wholesaling. AI and AI follow-up, both inbound and outbound, and like recorders, like AI agents, There's been more developments in the last 10 years than likely the last 25 or 30 years previous to that. And oh my, I have seen people who have had really successful businesses. They've been in the game for 20 or 30 years struggle like very, very hard. They've been struggling just really the last, I'd say 3 years. It's been difficult. And they haven't been able to adapt to the changing environment when it comes to the market has gone stale in comparison to 3 years ago, 4 years ago, 5 years ago, the market has gone stale. There's lots of legislation regarding wholesaling, which was a very primary exit strategy for many people, especially newbies. And with how much AI and automation there is, if they haven't adopted it, then they're not adapting to today's day and age. And people who are way less skilled are now competing at their level, if not above their level, and they're not keeping up. So they're losing out, they're having a hard time. So those would be the external factors, because we can't control the interest rates, we can't control the market, we can't control AI, we can't blah, blah, blah. But then on the internal level as well, having systems and processes in place So that your time, right? It's all coming back to time so that your time is as effective and as efficient as humanly possible. Having systems put in place so that the majority of your tasks are automated and the rest of them are delegated. This way you're not— what's the best way to describe this? Robert Kiyosaki wrote a book called Rich Dad Poor Dad. And he also wrote another book called The Cashflow Quadrant. Where he breaks things up into, are you an investor? Are you a business owner? Are you self-employed or are you an employee?
Right.
And so what I'm trying to get people to do is not go from an employee down to self-employed, because at this, that is the first natural step, of course, taking the leap of faith away from your job. And now you're kind of a one-man show. You're the solopreneur. But at the end of the day, I don't think that anybody starts a business with the intention of creating a well-paying but extremely stressful and taxing job for themselves. I believe that everybody who starts a business has the hope of one day being able to pull themselves out at least a little bit.
Right.
And put some people and processes and automations in place. But intentions die early. And I don't see people doing that very often, because they just don't know what to do. They haven't systemized their business. Therefore, you can't automate it, you can't delegate it, because it's all stuck in your brain.
Yeah. So I guess, I mean, you're helping them save time on, you know, managing their operations and maybe be able to scale, right? Like, it's harder to manage, you know, 5 different properties by yourself without a process, you know, you might be able to do it, might take long. But if you're trying to get to 50 properties, then you know, it's a lot different, right? And it's not as easy. So, I mean, from everything you've seen, like you've worked with hundreds of investors outside of, you know, maybe not having enough capital to scale, or maybe buying at the wrong time. Is it the processes or what else is other reasons that you see most investors fail within their first few years of trying? Like, you know, they want to get out of that self-employment, they want to get employment, they want to follow your footsteps and say, okay, I want to buy back my time. So that I can spend time with my family. I want to start buying some property. Um, but it's not as easy as, as, as you make it seem, maybe as, you know, some people realize it's a lot more work and, and, uh, maybe not as rewarding as they thought it would be. Right. Just buying one property and living off of it for the rest of your life. Right.
Right. Yeah. I see a lot of people make the mistake of getting shiny object syndrome. And please hear me out that I am the worst person at this. I, to this day, have shiny object syndrome, and I have to constantly put it at bay. And just to, I don't know, prove the point and really like hammer it home in comparison, because we all compare, so we may as well do it. I have signed up for 57 courses. Most people don't get past, you know, 3 or 4 or 5. Signed up for 57. Like, the last one was just a couple of weeks ago.
Last month.
Last month in February. And I feel like I'm probably going to continue to buy courses, frankly, because I'd like to think that I'm the student of my craft and I'm learning from the greatest of the greats in all of America. It started in 2016. I signed up for Fortune Builders, and then from Fortune Builders went to Rich Dad Coaching with Robert Kiyosaki, and then John Martinez and Grant Cardone and Dean Graziosi and Brad Chandler and all these people that are well-known in our industry. Tiffany Burns and Pace Morby and Jamil Damji, you know, like huge industry names down to the small guys, because you can learn a lot from them as well. But here's what— here's the— I think the right word is antithesis of this, or like the opposite. Let me also show you the other side of the coin. I already have a business.
Hmm.
I already am good at what I'm doing and my processes, my fundamental principles of how my business operates are there. In the beginning, if you implement what this guy is doing and you half-ass it, and then before you've even executed it fully and entirely, and you have this like, all right, I'm good. This is a smooth operation. You shift gears and now you're following this guy and what this guy tells you. And again, you half-ass it and you don't get it locked in. And then you shift over here. It's like, oh my, stop. Do one thing and get really good at that. And people will say, oh, Keith, you know, most multimillionaires have 8 streams of income. Yeah, Dumbo, they didn't go after all 8 of them in the beginning. They got really good at one and then they bolted on the second and they bolted on the third after the second was solidified, so on and so forth. That's how they build their wealth.
Right.
Um, so you cannot look at what somebody successful is doing. Success leaves clues and it's like a trail of breadcrumbs. You have to start at the beginning. You cannot do what they're currently doing. You have to do what they once did.
Okay.
If you want to have what they currently have. And this is a mistake that I see a lot of people make is they, is they switch from program to program to program and they never fully execute.
They don't commit. They don't, they're not, they're not, yeah. They don't stick to it long enough. Right. They're not patient enough to allow the results to—
Not disciplined. I think people are patient enough, but they lack the discipline in order to, number one, delay, delay your gratification. And number 2, do the hard thing first. Those are the 2 things that I think that people suck at.
I'm assuming, you know, that probably helped you a lot, you know, being in the Marines. I mean, people, yeah, discipline, 100%, you know, financial discipline, health discipline. I mean, I think if there's one thing I'll teach my kid, it's definitely, you know, learn to have those 2, right? I think you'll get far in life with, if you can stick to those.
I'm wearing my favorite shirt. Uh, stop whining, start doing. This is kind of, uh, this is kind of my motto. It's like, dude, I don't really care about your excuses. Just do this one thing. I'm not going to tell you 3 or 4 things to do. Just do this one thing. Your core constraint is fill in the blank. This is like a doctor, right? When people come to me, when clients come to me for coaching and mentorship, they have all these problems. They'll have 5 or 6 or 7 problems. It's not my job to fix all 6 problems. Not right now. Just what is your core constraint? What is the thing that is hurting you the most? What is holding you back? That's the thing that we need to fix. You cannot simultaneously focus on all of these things. That's a shotgun approach. Instead, you need to be laser-focused. This is my core constraint. Therefore, here is the diagnosis and here is my number one thing, my action set moving forward. And that takes discipline. Truly.
When you were speaking about AIM, you know, here, you know, we're talking about things changing a lot in this last few years. You know, you were speaking with hundreds of investors, supporting them, coaching them. Working with them, what have you, what do you see or anticipate being a good area? If you're, if you want to start, if you want to start today to start investing in real estate, where would you start and where would you focus and continue to build momentum?
Yeah, I think, oh, that's such a great question. A lot of folks are a little bit of a one-trick pony. And what I mean by that is, is they know wholesaling and they only know wholesaling, or they know rentals and they only know rentals, or they know fix and flips, but don't They don't know how to wrap notes. They don't know how to do novations. They don't— lease options, foreign to them. Like, there's all these different— what about buy— instead of just buying everything for cash, what about taking a mortgage subject to? What about buying with owner financing? What about a hybrid of both of those? What about DSCRing? You know, DSCR stands for debt service coverage ratio loan. So what about getting a DSCR purchasing product or a refinance product? Like, there's all these different entrance strategies and there's all these different exit strategies. And so to answer your question, they need to systemize their deal structure. So here's what I'll— here's the analogy. I'm the king of bad analogies, okay? So run with me. You have a McDonald's nearby you, correct?
I think so, yeah. A couple minutes away.
They're all around the world. You go to your Mickey D's and I'll go to my Mickey D's a couple minutes away. We're both going to order a Big Mac and we're going to come back. And we're going to look at ours and we're going to describe it, and you're going to look at yours and you're going to— they're going to come out looking the same. And I'm going to smell it, I'm going to describe it, you're going to smell it, you're going to describe it, and they're going to come out smelling the same. And then I'm going to take a bite, you're going to take a bite, we describe how it tastes, and it comes out tasting the same. Well, how in the world, thousands of miles apart, can we order a Big Mac and it comes out looking the same, smelling the same, and tasting the same? Because it's the same ingredients and the same process every time.
They've standardized it.
Yeah, every time, down to the temperature of the griddle when they put that burger on, and then they lower the lid and they press a button and it's a timer. And as soon as that timer goes off, beep, beep, it has the most irritating beep until somebody lifts the handle and takes that burger off. Down to they don't even trust you to put the right amount of mayonnaise because I may be heavy-handed and you may not like mayonnaise, so you don't put very much on. They, they have a trigger squeeze with the same exact amount of pump pressure. Their, their pickles are down to 3 millimeters of each other. Every single pickle, there's always 3 pickles and they're always within 3 millimeters of each other, no matter where you go, because everything is standardized. There's a system. There's a— there's almost literally a conveyor belt. If you think about how they toast their buns, it literally is a conveyor belt. You know, like everything is systematized. We need to do the same exact thing. In our real estate investing business, every single house, no matter where it is, I've invested across 34 states across the United States. I bought houses from anywhere. Literally my cheapest house was given to me. And the most expensive house I ever bought was $2.1 million. I've had houses where I've put in no money for renovation and I've bought houses where I put in $220-something thousand dollars, just call it $230,000 in renovation. So I don't care where it is geographically. I don't care what price point you're buying and I don't care the condition. How much you need in repairs. Every single house needs to go through the same exact deal analysis so that you know how to structure it both with your entrance strategy and your exit strategy. That way, just think about this. I'll leave you with this, or I'll close out this with the last analogy. Think about a lock. And I wish I had a key right now. Imagine I were to hold up a key, like the key that you open your door, your house door with.
Mm-hmm.
And it has those teeth on it, right? So there's levels of those teeth. It's 4 levels. It's either level 0, which is all the way down, 1, 2, or 3. And so think about every deal has 4 teeth on it.
Mm-hmm.
The needs of the seller, the needs of me personally, the needs of my business, and the highest and best use of the property, like based off of where we are in the market cycle. Those are the 4 variables that we have to solve for in every single situation. What does the seller need? What do I need? What does the business need? And what is the market telling me to do with this house? Based on those 4 things, that's the key. That's the combination that unlocks the lock. Our process needs to be the exact same thing so that it comes out whether I analyze the deal or you analyze the deal or Ms. K analyzes the deal or Sam analyzes the deal. We're all going to come up with the same entrance strategy and the same exit strategy. Why? Because it's based on the same fundamental principles. If there's any system that I would add in my business, it's a system for deal structure. By the way, not to like self-promote right now, but I have a deal structure course and anybody who listens to this, it's theirs for free. I think I gave you a link in the email before this, but they can just click on that link. It's 100% free. There's no gotcha. There's no catch. There's no bait and switch. Literally, it's, it's 100% for free. I do charge for it, but anybody who's listening to the podcast, um, thanks for tuning in.
Thank you, Keith. We'll definitely share that. I appreciate that. So just, just speaking a little bit more about the process, I think this is important, right? Because when people think they're looking to get started, you know, they're, they're ready to start on one, uh, one type of deal flow, which you're talking about. So one is, you know, systemizing and building a process for your deal structure and how you're going to execute it. How are you going to? You know what kind of deal, you know thesis you have. You're going to you're going to build that and you're going to follow it strictly. But if it's your first property, you know you probably don't know. Like are you just learning and trying to figure out okay this seems like a thesis that I would like to try out like commercial real estate. I'm going to buy some land and develop it. Am I going to buy you know there's just so many different variables and different ways of doing it in your area. Or are you building the process like of what you're talking about? This is this is our operation process. This is our financial offices. This is our this is our. These are the the construction crew we're going to use, and like do you get all that locked in and build the process beforehand? Or if you're especially when you're first starting out, like when's the right time to to think about this?
Oh, that would be so that would be so detrimental if you're building out the process of here's the construction crew and here's the finance, here's the lender, here's the agent, here's the title company, here's the home inspector, here's the ba ba ba ba ba ba ba ba. That's So stressful. So analysis paralysis, because then people are going to be like, all right, I need to get a lender. And then they're talking to 15 lenders and they're trying to choose the best one when it's like, brother, do the more important thing. You're getting the cart in front of the horse. The more important thing is that you get the best darn deal that you possibly can. So let's go find the seller.
Mm-hmm.
And then let's structure it next because potentially you're getting the lender put in place And we don't even know if we're going to structure it. Well, you may not even need a lender, like how I teach it. Most of the time when I'm buying a house, I don't even put money up.
Hmm.
I know that sounds totally crazy, but I've been doing this for 10 years. And I've never put more than $1 of my own funds into a deal. And, and I don't really like banks. So the whole like buying conventional or FHA or— no, no, no, no, I like unconventional ways of financing houses. I like creatively financing houses.
So buying it, seller financing, or what do we—
Yeah. Seller financing, buying it subject to, a hybrid of both, using DSCR funding, private lenders, hard money lenders. These are the sorts of things that I like because they're asset-based lending and it's not based on my credit. It's not based on how much I, what my debt-to-income ratio is. It's not based off of how much money I make in my job or how much I, you know, committed to the IRS for the— committed is the wrong word— claimed to the IRS the last 2 years. They care not about any of this. They care on the merits of the deal. Based on the deal, what is the loan-to-value, right? What is the debt service coverage ratio loan? What is the ARV? These are the things that they care based on the merits of the deal, not based on the merits of me personally.
Right.
I like that much better. And so a lot of times people get all sort— they just get their panties in a wad trying to get the perfect Lender in place and the perfect contractor to work on their house and the perfect— it's like, dude, we don't even know if we're going to buy a house in this area. Why would you get the whole freaking team lined up? You're just— frankly, you're just wasting everybody's time. You're just teasing everybody. Oh, I'm going to borrow money from you and I'm going to use you to list my house and I'm going to use you to do the construction on my house and so on and so forth. But you bring no value to them and you're just stringing them along. Right. Yeah. Let's get the deal first.
Let's get the deal first. So what is some successful tips you recommend to people to finding their first deal? What are they? What do they typically misunderstand about that early on? And maybe, you know, how do you think about building sustainable investing business here to actually grow, especially on deal flow? I think that's a. Is this speaking to realtors? Is it? What do you? What do you suggest there?
There's two things that I'll. I'll answer with that. Number one is that a lot of folks don't understand that it's not about the money. That was a double negative in that sentence. How can I word this better? Most people believe that if they offer more, they'll get more yeses. And this is absolutely, positively, entirely false. I will go up against—
Like more in terms of the purchase price or?
Yeah. Yeah. Like if I can, if I can give them as close to what retail is, then I'm going to get more yeses. And this makes sense. I mean, the logic is flawless. The more, the more I can offer somebody, the higher the probab— the statistical probability that they're going to say yes. But at the end of the day, the people that we are helping, typically they don't need more money.
Mm-hmm.
They need a faster close. They need to sell to somebody who isn't going to back out of the transaction. Somebody who isn't using conventional financing because their house isn't financeable. It's in terrible condition. Somebody who can clear up dirty title because they inherited it and then they got divorced and then somebody passed away and blah, blah, blah, blah, blah. Somebody who has liens on the— right, there's a multitude of problems that we can solve, whether they're getting— I've already alluded to a couple of them, but I have my big 5 motivators are divorce, inheritance, pre-foreclosure, health or safety issues, and people being a tired landlord. Like 80% of my houses come from these big 5 motivators. And And money isn't what solves those issues. It's creativity that solves those issues. And people think that throwing money at the problem is going to get them more deals. And what I would say to that is the person who wins the bidding war loses the most money. The person— let's say there's 10 people.
Yeah.
We're all bidding On this property, it's getting the price is getting higher and higher and higher, and then this person wins. That person just lost the most money. Think about this because then you have your expense. Let's say you bought it for this much, and it's only worth this much.
Right?
But then after you you renovated it, you put in this much, and then your holding costs are up here. You're going to take a you're taking a loss. The person who wins the bidding war is the one who loses the most money. It's not about throwing money at the problems, it's solving the root of the problem. So you have to get good at having uncomfortable conversations. You have to be good at asking really deep and personal questions and building trust and rapport. Those are the skill sets that pay really well. Throwing money at the problem is not actually the solution.
That's a really good tip. So really, I mean, that's why finding— I mean, at the root of that, you have to find the right Seller. I think that's the right thing, right? It's not really the property. It's the right seller at this point.
Who's—
yeah, who matches that profile, who's not looking for optimum price point, knows what they're, what they're going to hold on it. They don't want to rush. Yeah, you want the one—
That's exactly correct.
I need to sell it right. And then structuring it in a way that's, you know, still, it's a win-win situation for everybody.
Yep.
But you don't have to overpay for it. Love it. Yep. So maybe talking a little bit more about the mindset piece, which I think is important. You said, you know, there's some traps that people fall in at the beginning, it gets them stuck, or maybe cause them to quit too early, or maybe to share some system or habits they should maybe think about putting in place from the beginning. And just, just to help people maybe start thinking today, look, they want to get started there, maybe have some people they want to talk to, some potential sellers, but let's slow down and think about something else here, but without getting into too much planning and analysis paralysis and trying to put all your ducks in a row, right?
Yeah. Ultimately, People are not clear on what they want. And I feel like I can say this with at least some level of authority because I have 3 to 4 conversations with new investors every day and have for the last 5 years that RE Automated has been in existence. So I get to talk to a lot of people. That's hundreds, if not thousands of people that I'm kind of talking to, almost interviewing for 45 minutes. I just put them in an interrogation, if you will, and just berate them with questions to get a perfect understanding of what they need, So that I can then help them. And here's the hard-to-stomach truth is people don't know what they want.
The buyer or the seller or the investors?
The investor themselves is not clear on what they want. They're foggy. Maybe they have like a general direction, like, I kind of want to go this way. But like, if there's 365 degrees, let's try to do better than just like, I need to go that direction. And so, what they do is they get caught up in shiny objects and, oh, this person has the way. No, this person has the way. No, this person has the way. Hold up. Is that person in the place where you want to be?
Hmm.
If so, follow them. If not, then they're— I'm not saying that they're not successful. They're just going down a route that's not your route, right? What's right for them may not be right for you. It's not to say that what they're doing is wrong. What they're doing is obviously working. It's just not gonna fit my lifestyle. And so I see people chasing shiny objects and spending way too much money. They, they, they need all this sexy stuff. It's like, I need the $800 CRM and I need the $1,500 AI voice agent and I need the, the 16-powered dialer, freaking 16-line power dialer. That's $400 a month. Oh my, you pick up the phone and call for sale by owner people. It's free. You suck on the phone anyway. Like, let's just get down and dirty on your skillset cannot be offset no matter how good your CRM is, no matter how good your AI agent is, no matter how good your power dialer, 57-line power dialer is. If your skillset—
Mm-hmm.
Is not a good, what we call in the marketing world, it's not a good product market match. Like, meaning you're not solving the problems of the people that you're talking to, you're just— you're throwing money down the drain. And I see people doing this all the time.
Absolutely.
And admittedly, this was kind of one of the reasons why I started doing software is because I realized, like, number one, I can make a butt ton of money on it. Just calling a spade a spade. I can make a lot of money on this. And number two, I can sell this for way cheaper than what people are willing to pay because I see in the marketplace that people are willing to pay three, four, five, six, seven, eight hundred dollars for a CRM. Mine's two, and it does like literally ten times what theirs does. And it's made for real estate investors, not some bolted on, you know, like GoHighLevel, for example. It's it's for marketing people. It's good for like dentists and doctors and appointment setters. It's not specific for real estate investors. The whole real estate stuff was bolted on as an afterthought.
Mm-hmm.
Um, so, so I see that and I see this as a huge way of helping newer real estate investors by number one, providing something that's far cheaper than anything else in the marketplace. And number two, providing something that is way— has way more specificity in exactly what they're needing. That number three, Sets up very good fundamental principles in how they structure deals, how they analyze deals. Like our triage call is built in, our deal analysis is built in, our perfect presentation is built in, our purchase and sales agreement is built in, our KPI tracker is built in. All of these things, they're there included from somebody who's actually— who I have a successful real estate investing business and have for the last 10 years.
What do you mean? You mentioned that they're spending too much money. Just last question here, and then we'll jump into the rapid-fire questions, which is, you know, I believe that comes from some kind of form of procrastination. I think a lot of people, you know, they don't want to do the hard work, like you said, of like calling the owner directly or doing some of these soft things that— so they spend time trying to optimize all these tools and platforms, spend a lot of money, and it's just like, okay, but, you know, do the real work. And, you know, they don't do what actually moves the needle.
Yeah.
And do you think it's just because of lack of confidence in their skillset? Just, or they don't have the experience of picking up the phone and, you know, feel confident to talk to them. What's the biggest thing that's actually holding them back there? Why do you think they're actually procrastinating?
Here's the fact of the matter. Okay. I don't know how PC you want to keep this. I'll try to stay, I'll try to stay within like a little bit of, so it's, I mean, it's mental masturbation, what they're doing. It feels really good, but it gets you nowhere.
Right.
Well, I want, I need to, I need to make my CRM perfect. I want to have all these automations. And once I have it built out, then, then they're going to go from this workflow to this workflow, to this workflow. Dude, you only have leads. You haven't even converted a sale. What are you doing? But this feels good, whereas calling doesn't. And instead of here, so I have, I have a mentor right now. His name is Tom. He has 88 Rules of Business and, and he makes us memorize at least the first 11, like these 11, he drills into us. And rule number 1 is put revenue in first position. Well, a lot of people, they don't put revenue in first position. They chase the things that sound really good or that feel really good. And so it's just a dopamine hit. The second, he has also another rule. It's not one of the first 11, so I don't have it memorized perfectly, but it's something to the effect of your software should never outpace your revenue. Meaning you need to be constantly breaking your software and it's like, oh my gosh, if I were to spend the $40 per month on this CRM instead of the free version, then finally I could go from $20,000 per month to $40,000 per month. But if you ain't making $20,000 per month, then you don't have a right to be paying for— I know that sounds disproportionate, but I'm throwing real numbers at this. If you're not making $20,000 a month in your business, then you shouldn't be paying for a CRM. You need to go out and do more deals. You need to work on yourself, your skill set, your mindset, not your software. Your software is not going to fix your problem. Rest assured, I have coached a little over 1,000 people, 1,000 different businesses. Software doesn't fix your business when you don't have principles in place. If your skill set is holding you back. Software is not going to fix your stupid skillset. You need to have your— here's another way of saying it. Your business bank account will never surpass your mental headspace. If your headspace is down here, you're always disempowering to yourself. You're asking bad questions or saying negative statements, or you have a scarcity mindset. Your business is going to be capped by that. You need to work on yourself, even though it doesn't feel good. I know it's not a dopamine hit. I was literally on a call with my mentor not more than 2 hours— 1 hour and 41 minutes ago. And this is what he was talking about. Like, do the hard thing. Just eat the frog. I think there's a book called Eat the Frog.
Right.
Do the hard thing first.
Right.
And your business will grow. Why? Because your mindset is growing and no amount of systems or software will fix a poor mindset, or for that matter, a poor skillset. And so he has this rule, like, make sure that you're not paying for these softwares if you're not even generating revenue. Let's focus on the most important thing, which is put revenue in first position and let that revenue drive the business so that you're not always trying to play catch-up because you bought the sexiest software out there that has all the whiz-bang features that you don't even know how to use. Exactly.
And I guess this goes full circle back to our initial conversation, which I think if you dive to the root of that is like, have that discipline to do the hard things. And I think, yeah, we can have discipline to like explore tools and like do all those fun things that feel good. But having the discipline to do things that you don't want to do, that you don't feel like doing, but you know matters. It's like going to the gym, you don't feel like it, you're tired, doesn't matter. It doesn't matter. Just do it. Just do it. As your shirt says, just stop whining and do it.
Stop whining, start doing.
That's right. Exactly. So I think that's the, the, the, the theme of this episode. We'll change it to that.
Yes.
Love it. Love it, Keith. Um, let's shift gear. Ready to, to, to do it? Let's do it. Let's do it. All right, Keith, what's, uh, one activity you enjoy outside of work, outside of investing that gets you into a flow state?
Um, I like walking. So right before this episode, while I was on the call with my mentor, I had to change my shirt because I was wearing my tank top, getting some vitamin D. I did. Every single day I do a 3.2-mile walk. It takes exactly 1 hour and it is so good because when you move your body, you move your mind.
Absolutely.
And ideas come to me. I'm able to write things down, record some voice memos, use AI. You know, I literally will have a conversation with Claude while I'm, while I'm on my walk and then send voice memos to my team. Because great ideas are coming because I'm in a flow state because I'm moving my body. Absolutely.
With music or without music?
Oh, without music. No, I would absolutely prefer to sit in silence. I believe— well, there are studies that go both ways, right? People say binaural beats is probably the most impactful and most studied thing. And here's the thing though. Because I'm a little bit of a nerd. You can have the binaural beats audibly, but if you're not moving your eyes with it, then actually you're not stimulating your brain in the way that binaural— the originator of binaural beats, um, man, you said this is rapid fire.
That's right.
She, she was walking through her garden and she was looking to the left at this flower and she was looking to the right at this flower and she, she's walking through And, that's how binaural beats came about was actually the pacing of her eyes, not the pacing of anything audible.
Okay.
And so, that stimulation though between the hemispheres of our brain, that's how it was founded. So, if you're listening to binaural beats but you're not following something with your eyes, you are almost negating the impact that it has. And then, classical music I think is the most studied. Which I'm not a huge fan of classical music and I was a professional musician. So, I'd rather just sit in silence because then it forces my brain to come up with cool new ideas. Exactly.
Listen to the silence. So scary. What's one piece of advice you wish you had known? And if you can go back, you would tell your, say, 25-year-old self. I mean, maybe before you had your child, before you— yeah, let's say 20, 25-year-old self.
Cool. So, find the right Mentor is super, super important. I wish I had found the right mentor way sooner than I did because I struggled so needlessly for so long. Going back to time, time is our most important asset. You can make more money, you can have more things, you'll never have more time than you have now. So for me, I'm young, right? You said go back to your 25-year-old self before you had kids. We actually stopped having kids 8 years ago.
Yeah. Okay.
So I'm only 30 years old. And so we started having kids really young. Me and my wife have been married for almost 12 years. Next month will be 12 years. And our children are 8 and 10. So let's go back to when I was 20 years old.
Sounds good.
When I, when I had just started and I'm just on fire and like the world is my oyster. I believe that I can be a millionaire in like 3 months. And this is so exciting, you know, like, yeah, just what's the phrase? Like being naive is bliss or something like that.
Ignorance is bliss.
Ignorance is bliss. Yeah, man. Time is the most important asset and you need to protect it like your life depends on it because it literally does. And hiring the right mentor is so important. And if you hire the wrong mentor, you will destroy yourself. You will literally destroy your business, your finances, and potentially your life. I know people who are in jail right now because they hired the wrong mentor to do something that is illegal and unethical, and they're in jail for the next 20 to 30 years. I personally know them. That sucks. And the thing is, they didn't even know that what they were doing was wrong until they got brought into court.
They were just trusting their mentor. I guess they were just listening, obedience, maybe questioning. Yeah. Yep.
Yeah.
Keith, what are some of the biggest challenges you're currently facing in order to continue to grow REI Automated yourself? Meaning, you know, what keeps you up at night these days?
This is super easy. Oh, this is going to sound so rude. People are lazy and I have a hard time with hiring. I've hired, um, I've hired 8 people in the last 12 months and I fired 7 of them.
What are you looking for? Is there somebody, some kind of position you're looking for that you want to shout out to or—
Uh, sure. I'm looking for a setter. Meaning somebody who sets appointments on my calendar for real estate investors to get on my calendar. And it could be a DM setter because I get like 120 to 130 messages on Facebook, Instagram, TikTok, and I can't respond to all of them. I already have 2 full-time setters and they're like, they're tapped out. And/or I also need a phone setter, somebody who has perfect English. I will not take anything less than perfect English. And who is very comfortable talking real estate terms, number one. And number two, which is even more important, is probably the skillset of being okay challenging people who you feel like they already have it figured out. Challenge them and you'll find out that they don't.
Hmm.
So that's actually the positions that I have fired most of those 8. 6 of those were setters and 2 of them were marketing people, email marketing people, both of whom are fired. And only 1 of the DM setters have panned out.
Interesting ratios. Yeah. So that's a challenge.
I'm not a—
Yeah, because people just don't want to.
I feel like people want a handout and we no longer have the work ethic. I don't need to be working as hard as I'm working, but I enjoy working and winning is fun and I want to keep up the momentum and I'll put in 10, 12, 14 hours a day. I don't care. I'm great at it. I mean, I'll get up early, I'll stay up late and people just don't have that same work ethic. They're like—
Discipline.
Yeah. Yeah.
And they're not— I think you need to maybe rewire your— reprogram your hiring process and filter for discipline. It's like, how disciplined are you? This is what we're going to do.
Yes.
I'm sure you'll do a lot better.
Yes.
Yeah. Well, Keith, you know, speaking about mentors and maybe books, um, maybe can you share somewhere, what are the best 3 resources? It can be books, mentors, or people you follow in the space who you say have been most instrumental to your success over these last few years.
First, if, if you haven't read the book Rich Dad Poor Dad by Robert Kiyosaki, I think that you must read that if, if we're in the real estate investing sector. Let's go one level less specific, more general, and one level more specific. You are in the real estate investing sector and you already have read Rich Dad Poor Dad. So let's go up more general. Like leadership aspect would probably be John Maxwell's 7 Habits of Highly Effective People. This teaches you how to plan, how to lead both yourself and others, because you can't effectively lead what you first have not learned yourself. And we talked about vision and clarity earlier. Like one of those, habits of highly effective people is begin with the end in mind. A lot of people don't begin with the end in mind. They're kind of just like swinging for the fences, doing random stuff, hoping to get a— it's just magically like the world's going to fall together in the perfect alignment and everything's going to happen like you wanted it to. Let's get really clear on what we want. That's the end that we have in mind, and then reverse engineer the process to ensure that we get there. That's the right way to plan.
Yeah.
So 7 Habits of Highly Effective People for leadership, Rich Dad Poor Dad for real estate investing beginners. And then when it comes to the most specific thing, like what is your core constraint? If you're listening to the podcast and you already are a real estate investor or in this general space, is your core constraint marketing? Is your core constraint deal structure? Is your core constraint deal analysis? Is your core constraint Raising private money, tracking your KPIs, hiring and training team members, automation and delegate, like all these different things. The link that I gave you, I'll promote myself again.
Of course.
Those are all free. Any, any one of those courses. And they're not like crappy lead magnet courses, by the way. They're like 10 to 20 hours of course curriculum. I've taken everything that I've learned from these 57 people that I've paid really good money to learn what they know. And then I've gone, I've, I've I've systemized it. Basically, I've taken what I've learned, I've systemized that thing, and then created my own training around it. Any one of those courses is free to your audience, and with great specificity, it will target your core constraint and help you overcome that to take your business to the next level.
Love it. So add those, those books and as well as that guide into our show notes. So please make sure to check that out. Keith, what does success mean to you today, whether it's personally, Business, financial, life? I guess there's no right answer.
I want— one of my— so I have 6 core values that I run my life around. And the first 2 are really important to me. The first one is keep the most important thing the most important thing. And the second one is to live an exemplary life. I want to become the best version of myself. For me, but also for my family, like my household. I want— because here's the thing, my business could be rocking awesome, but if things aren't good in my family unit within these walls, then my business will literally erode itself from the inside out if I don't have my own life.
Absolutely.
Under check. And so I want to become the best version of myself and live an exemplary life for my wife, for my kids, for my team members, for my clients, and for people who just follow me on social. I definitely do not say that I have life figured out, but I do want to become the best version of myself and live an exemplary life by keeping the most important things the most important thing. And what I mean by that is a lot of time we're not clear. I feel like I'm kind of saying the same thing over and over, but a lot of times we're not clear on what we want. And what we need to get good at is saying no to the things that are not in perfect alignment with what we want. Because if we say yes to one thing, we're saying no to an infinite amount of other things. And if it's not in perfect alignment with what I want, I'm going to say no to it.
Right.
You have to get clear on what you want so that you can say yes to that one thing. Keep the most important thing the most important thing. What is that most important thing to you? If you don't know, how do you even know how to direct your life, much less lead other people?
Great priorities, finding your priorities.
Yeah.
Yeah. Love it. This has been this has been great, Keith. So just to wrap this up, thank you for for everything you shared. Where can you know anyone listening here? Audience investors founders anyone who wants to learn more about your product or to speak to you get in touch with you learn more about you and and your company.
Easiest way would be just find me on on Facebook Keith Gillespie. Gillespie is spelled really weird. It's G I L L I S P I E. And look me up. Our company's name is REI Automated. You can go to my website, www.reiautomated.io. And either way, you'll be able to find me, follow me. We got YouTube, LinkedIn, the whole shebang. Just Google me.
I'll come up. Thanks, man. I appreciate it, Keith.
Good job. Yeah, brother. Thanks, Akeel. Cheers.
Thank you all for watching this episode and joining SaaS District today. Don't forget to like, subscribe, and hit the bell for future episodes where we interview top leaders in the SaaS industry. If you're a SaaS company looking to grow and unlock the true value of your business, get in touch with us at Horizon Capital, and myself or one of our consultants will provide a free assessment to help you get there and hit your goals. If you have any feedback or suggestions for this podcast, please comment down below and help us improve. our content for you all. Thanks again, and see you on the next one.
Bye.
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