AI for Real Estate Investors: CRM, Systems and Automation That Scale

Keith Gillispie (00:00)
Oftentimes I see people they’re doing really well, they’re making half a million dollars net profit a year or more, but they are a slave to their business. They are super stressed out. They’re losing their health. They’re losing their spirituality. They’re losing their marriage. They’re losing their kids. I do not believe that. My number one core value is keep the most important thing, the most important thing. And

money will never be that, at least for me. And so I believe that you should be putting systems in place to put people in place and automate everything that you can so that you can pull yourself out of the business.

Dylan Silver (02:02)
Hey folks, welcome back to the show. Today we’re joined by returning guest, Keith Gillispie, a real estate investor and founder of REI Automated. Prior to REI Automated, he built a seven-figure real estate business on his lunch breaks while serving as an active duty Marine and went on to complete transactions in 34 states. And now with REI Automated, he helps investors scale through systems, automation, and operational excellence. Keith, thanks for joining us here today.

Keith Gillispie (02:30)
Thank you very much, Dylan. Super appreciate the opportunity, man.

Dylan Silver (02:33)
Now, how did you build a real estate business while serving as an active duty Marine?

Keith Gillispie (02:38)
Well, there’s a saying that I’m gonna butcher that says something to the effect of necessity is the mother of all invention. And that’s really what it was over eight years that I was active duty, I was overseas thirteen different times. And during those times, both of my children were born. And I would come home and my wife would have to reintroduce me over and over and over to my kids.

And so I loved my time in the Marines, but it was good for only a season. I really needed to come home and be a father for my children, right? And so that was the need is I needed to build this real estate investing business to get out of my W-2, which was active duty in the Marines. And so 2016, we started our real estate investing business. And it’s really hard being active duty, especially in the Marines, right? Especially when you’re gone overseas all the time. You have very little time, you have very little.

mental bandwidth or capacity. And so I struggled very much with my time, with my efficiency, with my effectiveness. And really I only had an hour a day. And that was on my lunch breaks. I couldn’t do it before work. I couldn’t do it after work. Not allowed to have my phone on me while I’m at work. So the only time that I could do it was on my lunch breaks. And and that really was a game changer for me. That, you know, rock I was between a rock and a hard place and that’s really what

morphed into such a beautiful thing that it is now.

Dylan Silver (04:01)
Now, for other folks who are in a similar situation, let’s say they’ve got a very limited time to be a full-time real estate investor, they’ve got an hour a day. Would you say to those folks it’s possible, or do you think that, you know, it really takes a certain kind of person to be able to make use of that one hour to build a real estate portfolio and business?

Keith Gillispie (04:24)
Here’s what I will say with I feel like pretty objective facts. I have about a thousand data points behind me of different companies that I have access to because they use our software. building the systems, building the software, building the automations in one hour per day takes a very special person. I and I don’t want to like

Beat my chest or boast, I was hooked up by a whole bunch of amazing men and women that were in my corner that super helped me out. It cost me a lot of money. It cost me a lot of time. You know, like as with anything, it’s always twice as hard. It costs twice as much and it takes twice as long as you originally anticipate.

And so I will say that it takes a very special person to build everything from scratch. However, with more than a thousand people now who have used our services, I mean, I literally have people that are deployed right now in

Well, they’re overseas and they’re closing deals. She like we have a gal who closed a deal this month. She closed a deal one month ago. She closed two deals the month before. We have another active duty service member. He’s been with us for eleven months. He’s closed eleven deals. one and he’s like full-time. He’s a naval officer and he’s going to college full-time, twenty-three course credits, got a newborn baby girl, just beautiful, you know, but super tapped, very limited on time. So I can

recount story after story after story after story. Not just active duty military, but law enforcement, firefighters, EMS, like first responders. Like we are on call no matter what. I have truck drivers that are driving down the interstate, talking on the phone, right? Everything is recorded, AI analysis, sentiment, action steps, everything is done for them. It’s all automated. After that, the thing that they need to do is just pick up the phone and call the leads.

And so I I’ll say very confidently that you don’t need to be a special person. I have literal minors, 17-year-old kids that are crushing it. My oldest client is 84 this year, using our software, crushing it. So there’s a huge gamut. And again, I can recount story after story. I think it’ll get boring at some point, but we have, you know, left and right lateral limits that are huge of people being successful. You have to have the right education, the right software, and the right support.

With those three ingredients, I really think that anybody can be successful.

Dylan Silver (07:28)
Now was REI Automated born out of that necessity? When did this come about for you?

Keith Gillispie (07:34)
Yeah, so unofficially REI Automated started all the way back in two thousand and seventeen. It wasn’t called REI Automated and it was never meant to be a commercialized thing. It wasn’t meaning it was never meant to be sold to other investors. I just realized that I only have one hour per day. And so that hour had better be as efficient, as effective, as automated as humanly possible. And so we set out to create our own our own software. And it really didn’t even start as software, it just started as SOPs, right? Just checklists, just systems and refining those processes.

As we got really good at streamlining those processes and removing any friction points, we began to automate a lot of it, which of course the naturally birthed software. And it started with a CRM, and now we have six different verticals under the Deal OS, the deal operating system. So we have DealLabs, DealStream, DealFeed, DealBase, DealBots, DealGPT. And so those are the commercialized aspects that we’ve now turned all of these systems that have helped me be super efficient.

In my one hour of time and literally like I haven’t done a deal in fifty states, but I’ve done deals in thirty-four states and I haven’t been to thirty-four states. it works virtually as well with very limited time. And so now it’s been able to go out and help thousands of other real estate investors in their companies.

Dylan Silver (08:48)
You mentioned the different ways where you’re able to help folks and how it’s scaled into several different sub-platforms, if you will. When you were starting, was there one segment of this that you were hyper-focused on?

Keith Gillispie (09:03)
Yes. It absolutely was the CRM. I I hired people. I I believe that most of most of the things in your business should be either automated or delegated. If you’re truly gonna be an owner of your business and not necessarily an owner-operator within your business, you have to either automate the tasks or delegate the tasks. and that CRM was a I would consider it like a linchpin, like it’s a pivotal role

We have 389 automations in our CRM. Like, that’s how many things that we’ve been able to automate. All of the mundane, menial, repetitive, stupid, like minutiae tasks that we as entrepreneurs do to like, I’m not good at paperwork. I’m not good at holding people accountable. I feel like that’s micromanaging. I’m not good at follow-up. I’m not good at making sure that my admin logistics, my P&L is up to date, my blah blah blah blah blah. There’s so many things.

That can be automated. And if they’re automated, your business runs very smoothly.

However, if they’re not automated, they simply don’t get done. Yeah. We as the owner aren’t gonna do it. And that’s when there’s huge gaps that we fall into in our business and and we cease to have control over our numbers. We’re not tracking our metrics. We don’t have a a pulse on what is happening with the team. We don’t know what our

Our fatal flaw is, you know, like what is our core constraint? All of those things can be fixed by having a CRM that does the majority of these things for you. And like I said, we’ve effectively made it. I mean, the house isn’t gonna flip itself. It’s still super hard. Entrepreneurship is the hardest thing that you’re gonna do. The real estate market is tough right now. But what I will tell you is our CRM, basically, you have to just pick up the phone everything else, we have systems for it.

Dylan Silver (11:21)
On a granular level, how does that work without giving away the secret sauce here? How does that go pick up the phone?

Keith Gillispie (11:26)
And then

at the end of the day, here’s what I believe. I call it the Mickey D’s Method. So you live in Texas, I live in in Florida, thousand plus miles displaced. If we went to McDonald’s and we ordered a Big Mac and we came back and we showed it to each other and we smelled it, we took a bite, it’s gonna come out looking the same, smelling the same, tasting the same. Why? Because it’s the same ingredients, it’s the same exact process down to the temperature of what you know how they cook the patty and the temperature and the time that it’s on before it begins to beep. They don’t even trust you to squeeze the mayonnaise yourself. They have a little thing that you, you know, shoot the little gun that shoots it out.

And and so I believe that we need to have a Mickey D’s Method in everything in our business, everything, absolutely every single thing that you do in your business, how you triage the seller, how you determine your ARV, how you estimate your repairs, how do you determine your entrance strategy, your exit strategy, how you raise your private funds. There is a process for absolutely everything. And creating that process is super important for us to flesh that out, remove this these friction points.

Make sure that there is no weird edge cases that will throw it through a loop because when you automate something, man, like if you’ve missed an edge case and it happens eight percent of the time, then it’s going to happen often enough that you lose money, right? Like you this really needs to be like 99.9999% of the time. It works flawlessly. That’s when you can automate something. And so we’ve just done the process so many times over and over and over.

Regardless of what it is, whether it’s like I s like through the whole thing, how do we generate the leads? How do we triage them? How do we do the deal analysis? So on and so forth. What are the exact steps, literal step by step, regardless of exit strategy? If we’re gonna wholesale it, if we’re gonna wholetail it, if we’re gonna retail it, if we’re gonna wrap it, rent it, novate, lease option, each one of those has certain steps that are handled in order, in this precise order. And like I said, the majority of it is automated.

There are some things that shouldn’t be automated. And I believe even with AI, I’m a huge proponent of AI. We have 30 agentic AI agents that work for us, 24-7. So I’m a huge proponent of AI. However, I don’t think that the phone call should be automated. I’ve experienced it myself. I have AI bots. It’s we call it DealBots, that that make follow-up calls that take inbound calls. And I’m here to tell you, it just made me feel icky.

When that AI was trying to negotiate price with me on a real house that I actually wanted I I said I want to feel what this feels like to be the seller. And I didn’t like it. So that’s the one thing that I think as of right now, it shouldn’t be automated to an AI bot.

Dylan Silver (14:38)
Now, when we talk about what this looks like on a granular level, gonna be different for each real estate strategy and the niche that the operator has, can we get into specifics about a success story of someone using REI Automated?

Keith Gillispie (14:52)
Yeah, well, I have several actually. which one do I pull from? There’s a there’s three that come to mind because they’ve just done you can go to go to our YouTube channel. We have these client highlights. I’m about to do another one with a big guy, his name is Gilbert. And we’ve been able to completely turn it around. I wonder if I yeah, you know what, I have this client highlight right now. He’d literally just submitted it. I’ve got HUD one, HUD two, selfie.

view he’s booked for this week. JD, my old boss. let’s talk about him. My old boss in the Marines. He was my staff NCOIC. I got out of the Marines 2020. He got out of the Marines 2024. 25 is when he retired. And he knew darn well that I was doing real estate while I was active duty in the Marines. I wouldn’t talk about it that much.

Like he kind of knew that I was doing this real estate thing, right? He got out of the Marines, he got a government job, and he’s like, dude, I know there’s more to life than this. And so he reached out to me. And he recently did his first deal. It’s been just a couple of months here. And I don’t think it was a smoking deal. I think he made like twenty-seven thousand dollars, if I remember correctly. but he bought this house. He lives in Hawaii, and this house is in the Midwest, just out middle of nowhere, dude. And it was kind of like

Man, should we even do this deal? Like it’s really podunk middle of like Iowa or something like that. And he bought it at such great price, such great terms, did a little renovation. I don’t encourage people to do big renos on their first deal, especially. I don’t even like doing big renovations. I do like one per year. so a little, little renovation slapped it on the market. Like I said, I think he did just less than thirty thousand dollars.

Net profit. But here’s a cool thing. Number one, it was his first deal. A lot of people lose money on their first deal. Number two, he did it completely virtually. He’s never been to that state, much less that city or that house. And he was able to do it from thousands of miles away. And I think that there’s a five hour difference between Hawaii Standard Time and Central Standard Time right now. And he and he was able to do that in spite of everything. Full-time government job, wife, two kids, you know, like he has all the excuses

That anybody ever could. Yet he was still able. He had the education, he had the systems, he had the support, and he was able to pull it off. And so now it’s like, all right, now that you have this money, let’s try to double that over the next six months. Then we’ll try to double that over the next six months. I believe that that’s a really healthy growth, somewhere between a two and four X each year. You can sustain that. In my opinion, you can say sustain that for five, six, seven, eight years, your first five to eight years in business.

Dylan Silver (17:40)
Let’s talk about a different set of investors here, folks who may already be full time themselves and maybe have some systems in place, but haven’t dipped in into automations. Yeah. What does this look like for them? How can folks who have scaled a portfolio or a business implement automations to help them grow even further?

Keith Gillispie (18:01)
Cool. Well first let me be I wanna drive away the wrong type of person for us specifically in REI Automated. We kind of have a threshold right now of 50 deals or more yourself. I’ve had many of those clients and at that point I feel like you should never stop doing what’s working. What you’re doing is already working. I do have a very specific

Way of doing everything as I’ve already stated. And sometimes there’s a little bit of rub at this point is like, I know what I’m doing. You know what you’re doing. Maybe it’s a different flavor and that’s totally okay. There’s no right or wrong. It’s simply right or left. And what may be right for me is wrong for you. And I’m not here to judge. so let me just make that delineation really quickly. Now we have to we we have several clients actually who have done hundreds of deals like I’m talking like 800 plus deals but the majority of that was

As a part of a team, right? They were the acquisition manager on that team. They were a transaction coordinator on that team. So when I say 50 deals or more, I’m really saying 50 deals where you are the owner of the business managing the entire operation. Anywhere between zero and 50, let’s say five to 50 actually. They have some success. They already kind of know what they’re doing. They’re building their portfolio. We can really, really, really help that person go from an owner-operator to an owner.

At this point, now we’re putting systems in place to put people in place. We’re putting systems in place to put people in place.

Oftentimes I see people they’re doing really well, they’re making half a million dollars net profit a year or more, but they are a slave to their business. They are super stressed out. They’re losing their health. They’re losing their spirituality. They’re losing their marriage. They’re losing their kids. I do not believe that. My number one core value is keep the most important thing, the most important thing. And money will never be that, at least for me. And so I believe that you should be putting systems in place to put people in place and automate everything that you can so that you can pull yourself out of the business.

You’re no longer do I have I do not talk to buyers, sellers, title companies, attorneys, contractors, appraisers, none of it. The only time that I do is when my team makes me mad and I’ll make a phone call live just to show I still got it. You know, like it put in check a little bit. This is see, this is how to save the deal.

And then I pay myself the commission instead of them. but otherwise, dude, I don’t I haven’t made those phone calls for about six years. Six years I’ve completely displaced.

Dylan Silver (20:32)
Now, when we talk about folks who are in that spot and they have done a couple of deals, what are the first things that they could and should be doing to automate?

Keith Gillispie (20:42)
I don’t think that automation is typically the first step. I think that systemization has to be like step zero, if you will. And then from that systemization it’s going to split. There’s a great book called “Seven Habits of Highly Effective People”, written by, I believe that’s Stephen Covey. And one of those successful habits of highly effective people is begin with the end in mind. And I think that there’s two ends in mind. Some of the things should be automated, but some of the things should be delegated.

Before either of these can happen, these cannot occur until you’ve first systemized and streamlined the process. Do you know record yourself doing it? What I don’t care if it’s a screen recording or you’re writing out instructions. We use Scribe for some of those things. We use Asana for some of those things where we’re putting this in, and then, you know, here’s the here’s the task. And then there’s like, I don’t know, five components of that task.

And of that component, now you have subtasks. And sometimes they’re subtasks of the subtasks, right? And you’re just built, you’re fleshing this out, you’re building the body of this task. And once you’ve written out the entire thing and recorded a video for each thing, it’s not just showing what to do, but also more importantly, explaining why. That way somebody can take in the Marine Corps we call it commander’s intent.

Hey, maybe, maybe it doesn’t look exactly like this. Maybe we’re not even using the same exact software, but I understand why he was doing that thing and I can go out and solve it a different way. That’s the most important thing, is determining the why, the commander’s intent, why you’re doing something in order to hit that result. And then it’s on that person to effectively lead themselves and take, you know, take charge of however they want to do the thing. As long as we have a mission mindset right and have a results-driven end in mind.

Let’s delegate that leadership to them. Let’s push it down and allow them to lead that department. If it is, you know, lead manager department, acquisition manager, department, transaction coordination, project manager, disposition, whatever it is, let that person do their own tasks. So first, systemize everything. And these things really have to be bulletproofed before you automate it, before you delegate it. Here’s why I also say this, because we’re gonna systemize it for ourselves first.

If you hire somebody, I made this mistake a lot. I I’ve hired about 80 something people now. I think I’m around 85, 86 people. And for the first probably three or four years of business Dylan, I s totally screwed up. I completely failed the employees and team members that I hired because I expected them to build the system. When instead I should first have built the system and given them something to plug into.

This is how to do the thing. This is why we do it this way. Here’s a written SOP and here’s some video examples. Here’s your training. Your training is, you know, your the onboarding is watching these videos. Here’s your job. At that point, now it’s on me to lead them. It’s on me to uphold standards. It’s on me to mentor them, answer questions. It’s no longer on me to actually tell them what to do.

Dylan Silver (23:43)
We are actually coming up on time here, Keith. Anything you’d like to mention directly to our audience?

Keith Gillispie (23:50)
Ooh, is this my opportunity to talk about me for one minute? so I’ve been really excited about what we’ve built out the last 20 months or so. We’ve come out with six different verticals. AI has been tremendous in this. A lot of people they build out these AI things and then they don’t work or they can’t market it. They don’t have a user base. We have hundreds, if not thousands, of people on these softwares that we’ve built out. So we have six different ones. I mentioned it earlier in in the

Dylan Silver (23:54)
Go ahead.

Keith Gillispie (24:18)
The podcast, but they’re all verticals of the deal operating system. We call it Deal OS. So they all start with deal, which is a little bit confusing, but we have Deal Labs, Deal Stream, Deal Feed, Deal Base, DealBots, DealGPT. I’ll go over like two minute two sentences for each one. Deal Labs is our on-market lead generation software where you find diamonds in the rough of properties that are already listed and you would have totally looked over it if you were just scrolling on Zillow.

We’re scraping, we’re enriching, we’re analyzing, and we’re scoring those so that you can just start at the top, work your way down. You’re gonna find a deal in the first 10. Next, we have Deal Stream. This is our off-market lead generation. A lot of people are already have softwares like this where they can, you know, I want high equity absentee owners who live out of state that are in code violation, and then we send direct mail to them. That’s all built in. We have discounts for the direct mail as well.

We have Deal Feed, that’s PPL, that’s where you know Google ads, and then the leads are coming to you. We’re feeding you the deals. Then we have Deal Base, that’s home base for all of your deals. That’s your CRM with 389 automations. We have DealBots, these are our AI outbound voice agents that are following up for you, as well as inbound agents. So if you can’t get to the phone, somebody calls you after three rings, it goes to your AI.

No more missed calls, no more voicemails. Then we have DealGPT, which to my knowledge is the most advanced Deal GP or GPT ever to be created for real estate investors. It is a fine-tuned RAG model that has been trained on t tens of thousands actually of documentation as of right now. And you can literally ask it anything about real estate and it will have proprietary knowledge, especially involving our softwares, to help you do it. So that’s all under the deal operating system.

You can and if any of that interests you, we have write-ups and videos on all of them if you go to our website, reiautomated.io.

Dylan Silver (26:11)
All right. Keith, thank you so much for joining us here.