Jermaine Massey is the CEO and Founder of Cashflow Diary, a training and development brand for building short-term rental entrepreneurs.
Before Cashflow Diary, J. raised capital and invested in traditional real estate (single-family homes, note brokering and holding, cell phone towers, commercial real estate, and apartment buildings).
Eventually, he built his real estate investing training program to share what he learns continuously through his years of successful, real-world experience owning hundreds of traditional long-term housing units. When one of his students asked him what he knew about the world of short-term rentals, the answer was not very much.
Once J. started learning about short-term rental strategies, he saw a world of opportunity in front of him. He built his very own 34-unit(46 bedrooms)-and-counting short-term rental business from scratch — which he still owns, grows, and operates — and has shifted his Cashflow Diary brand to focus exclusively on building and training short-term rental entrepreneurs.
Now he’s built a community of thousands of like-minded people from 16 countries that he learns from every day and shares his knowledge through his Cashflow Diary podcast, YouTube channel, Facebook groups, and annual Short-Term Rental Summit training events.
Connect with Jermaine on LinkedIn and Instagram.
What You’ll Learn in This Episode
- What makes short-term rentals a “gateway drug” for real estate investing?
- What kinds of business models are best for married couples who want to grow a company together?
- How can a new short-term rental investor keep up with all the new regulations in this industry?
- Why is listening to the most important part of becoming a better salesperson?
- How can someone leverage short-term rentals without owning property
This transcript is machine transcribed by Sonix
TRANSCRIPT
Intro: [00:00:04] Broadcasting live from the Business RadioX studios in Atlanta, Georgia. It’s time for High Velocity radio.
Stone Payton: [00:00:15] Welcome to the High Velocity Radio show where we celebrate top performers producing better results in less time. Stone Payton here with you this morning. What a marvelous conversation this is going to be. You guys are in for such a real treat. Please join me in welcoming to the broadcast CEO and founder of CashFlow Diary, Mr. Jermaine Massey. Good morning, sir.
Jermaine Massey: [00:00:40] Hey, good morning to yourself. How are you?
Stone Payton: [00:00:43] I am doing well. Really been looking forward to this conversation. Got a ton of questions. Sure we won’t get to them all, but I’m thinking maybe a good place to start is to maybe have you articulate mission purpose. What are you and your team really out there every day trying to do for folks, man.
Jermaine Massey: [00:01:03] Got it. Got it, Got it. Well, hold on. Did you say you were looking forward? Absolutely. Tell me why. What’s that about? I mean, this isn’t your I mean, you do lots of this stuff.
Stone Payton: [00:01:12] Well, I do. I get to do a lot of interviewing and conversations, but I am particularly interested in real estate and learning how to invest and make money in real estate. And so I am all ears and on the edge of my seat to see if I can learn some things, at least what I might begin to start reading, thinking about doing. And so I am particularly interested in this conversation, man.
Jermaine Massey: [00:01:38] Got it. Got it. Totally makes sense. And same for most people. It’s not like you wake up one day and go, Hey, I can’t wait to become a real estate investor. I didn’t do that. But what we do is quite straightforward. I like to say that we create seven figure families. That’s what we do over time. That’s what we do. How do we do that? We start by teaching the principles of having assets, produce your income instead of your labor, which is expressed with short term rentals. So at the end of the day, it’s teaching someone like yourself how to own, build, manage and control assets, in this case a business asset using somebody else’s property at the beginning so that you can produce stable cash flow, but then allows you to purchase your own assets like real estate.
Stone Payton: [00:02:32] I knew this was going to happen. I’ve got already I got to know out of the box because I don’t think I’ve even come across that idea of using someone else’s property. I’ve been operating under the impression I’ve got to go get my own.
Jermaine Massey: [00:02:44] You know that when I first started this particular business model man, seven or eight years ago, I had the same paradigm and I was sitting at Starbucks one day and I can I remember where I was when it happened, and I was just doing the math because having come from, you know, cell phone towers, commercial retail as single family houses and mortgages, a whole bunch of type of different real estate, I have a process that I go through when it comes to due diligence. And I was in escrow on a four bedroom house out here in Southern California. And I was just going through the process, making sure the numbers made sense. And then as as disciplined would have it, I ran my process and asked myself, compared to what that is, by far one of the most important questions I think people could ask themselves, because we will say things like, it’s not a good investment or it’s too expensive or isn’t that cheap. And these are all relative terms compared to what? And because I asked myself that one question, I ended up redoing the numbers to realize the $100,000 that I was going to be putting into this particular property would earn a higher return if I rented other people’s property first, as opposed to buying a particular house. And that set me off in a completely different direction. And well, here we are today.
Stone Payton: [00:04:11] So say a little bit more about your back story. How did you land in this line of work and in general, were you always going to be involved in real estate or were you doing something completely different?
Jermaine Massey: [00:04:23] Sorry, that no, I was I was not always involved in real estate. I well, I got started into real estate, not because I was trying to get into real estate. I needed to eat at the time. My my then wife was pregnant. She when she was pregnant, she has a condition known as hyperemesis. She couldn’t eat or drink. I had a punctured lung because I was playing volleyball and then I landed on a guy’s head. I have a public high school diploma. That is my version of a PhD. And when you combine all those things together, what it comes down to is I needed a way to eat. And many of us say things like, Hey, I have to go to work and we’ve got to be careful about the words that we say or I need a job. No, what you need is a source of income. And that’s what I learned. And I started in the real estate space as a wholesaler, what’s popularly known as a wholesaler, because with a credit score of 398, there was no lender that was going to touch me and. I still needed to eat, so I had to find a way to create value. And that was the key that wholesaling taught me is that the marketplace does not care about my situation or your situation. It cares about my solution. And therefore, if I can bring a solution, they will absolutely compensate you for it. And we ended up doing around 200 or so wholesale transactions earning between 2000 to $26000 each.
Jermaine Massey: [00:05:55] And that’s how I got introduced to the IRS because taxes. So when I learned that they wanted their fair share or you could say unfair share, depending on how you look at that, I said I don’t want that to happen again. So I started collecting houses that and that’s it. My real estate career has been comprised of how do I solve the next problem that I am now experiencing. And that’s exactly how I ended up in short term rentals, is what very few landlords, long term landlords will tell you. It’s a great way landlords owning lots of property is a great way to build wealth. It’s a horrible way to build income. And that’s what I found out, is that I needed a more active today income, not just net worth wealth building because the margins in long term landlords were so thin. So I was looking for a way to take an existing portfolio and make it profitable today while debt was still on the property, which is what I think most of your listeners and most of the people who can hear us are. That’s the situation you’re in. You’re barely your margins are so thin and it’s either deferred maintenance or cash flow. And the short term rentals was a way to make that happen. Or is the way, in my opinion, to make that happen for today’s investor.
Stone Payton: [00:07:16] So for the uneducated, uninformed, at least that’s how I’ll characterize myself. Just the idea of a short term rental. It it sounds like it’s going to be a lot of a lot of work, right? Like whereas a long term thing sounds like, oh, I’m going to go through this one transaction and I’m set for a while. But but maybe there’s some misconception, misinformation, some perspective you can offer on that that.
Jermaine Massey: [00:07:43] Did you say maybe some course. Okay. So well that’s like here’s that that’s like saying I mean literally it’s like saying, you know, when I go to Costco or Sam’s Club or if I own one of those, that’s a that’s, that’s just man, that that’s the ticket. That’s the way to do it. But man, if I was, you know, Target or Wal Mart or Nordstrom, that’s just too much work. That’s what you just said to me, because what a short term rental is, it works on the exact same principle as wholesale to retail or like a vending machine. What we buy is inventory. My inventory is time. I buy 365 days at once from a wholesaler landlord, and then I resell those same days one at a time. Now, is there a difference between my customer and the traditional wholesale? Yes, absolutely. There is some work, but like all work, it can be systematized. And it’s not, especially in the real estate space. It’s not like I’m physically doing the work. Your boy can’t design a doggone thing. Don’t ask me to clean. It’s not going to happen because, yeah, that would be really bad for somebody. But somebody knows how to clean, somebody knows how to design, somebody knows how to run inventory and procurement. Somebody knows those things. I don’t my job as entrepreneurs to use other people’s resources to put them together to productive use and improve the quality of life of someone else with our product or service. So it’s no different. It’s just different work. That’s how I look at it.
Stone Payton: [00:09:30] So so speaking of the work for you, where do you plug in? Do you plug in by educating someone like me, or do you get involved in some of the the execution of the where does your work begin and end in this regard?
Jermaine Massey: [00:09:46] Never. I never end. But at the same time, I do both. We run a portfolio across multiple states and we teach individuals to run their portfolios across multiple states and countries. We’ve had the privilege of working with individuals now in 17 different countries on this particular business model. But on a day to day basis, myself and the team, yeah, we process anywhere. I would say right now we’re probably at 102 hundred reservations a month. Wow. So ourselves and we I’ve forgotten how many people we have helped learn to run portfolios like this as well. And again, that that’s the thing. Some people, when they’re thinking about short term rentals or Airbnb as a popular call it, they’re only thinking about one or two. I’m not the guy for that. I only know how to do this Well, when you want to do ten, 20, 40 are most popular student or successful student got up to 120. They’ve since gone on to own a couple of hotels. They’ve been featured in Conde Nast as well as on Netflix. So it’s stuff like that. That is that’s my game. I don’t know how to do it small. I only know how to do it such that it creates a seven figure family.
Stone Payton: [00:11:07] So so the mechanism the mechanism is is cash flow diary. Is it like a course that you go on online? Is it is it personal interaction with with you or someone on your team? Is it a hybrid of that kind of thing? What’s the mechanism?
Jermaine Massey: [00:11:21] Yeah, no. Well, we tried the we tried the course model like everybody else. We but we do still provide the videos for those who really, really think, oh, we can figure it all out on our own, right. Our experience has taught us that it takes a whole lot more to teach them. One, I mean, about the only background I think could get it halfway decent is someone who comes from the logistics world simply because the amount of moving parts to execute this as cleanly and smoothly and as inexpensively as we do is really it. To me, it feels like a work of art. Or maybe if you ran a cruise ship, if you did something like that that you’re in. But no, it we it’s what I like to call an accountability program. It’s not a there’s not a lack of information. Still. There really isn’t. Right. So the information. Yes. Is it out there now? It’s not organized. So there is some value to that. But and let me just go off the deep end for a second. A couple of weeks back, we had a student say, hey, do you have an SOP? That’s a standard operating procedure for when when a guest dies inside one of your units now. If you go in search today on the Internet, you can’t really find that for a short term rental operator. But we have that right.
Jermaine Massey: [00:12:56] What do I do when XYZ happens now and now that I’ve gone off the deep end, everybody’s mind is coming up. Yeah, but what about this? And this and that and the other? And imagine having documented, vetted processes that anyone could follow in order to execute that so that you, the owner business operator. I tend to find out about things that happen like during our weekly debrief. I don’t find out until the problem is solved, cleaned up and somebody else is already there. That’s where I am today. But at the end of the day, that’s what I’m talking about. You can provide any product, business or service with the proper systems in place at scale without it having to take all of your time. But the truth of the matter is this business is really hard. From 0 to 7 units, it gets easier from 7 to 15, and after 15 we’re talking maybe one hour a day if you have put in the proper systems. But again, most people that I run into can’t fathom what I just said. They are right now having some sort of conniption fit, thinking about like, wait, wait, wait, what? How many did he say? Because they can’t they’ve not seen it. They don’t think it’s possible, but yet it’s what we’ve been doing for a number of years now.
Stone Payton: [00:14:18] So how does the whole sales and marketing thing work for you guys? And I really mean it on a couple of different fronts. One is getting some critical mass of people wanting to learn these things and get involved from the Cash diary standpoint. And when you’re out there, I don’t know, selling people on on working with you in any perspective, insight, experience on the whole sales and marketing thing, it would be helpful to me personally, but also, you know, our listeners as well, because they’re all so many of them are entrepreneurs out there. They’re having to sell in some way.
Jermaine Massey: [00:14:52] Well, so this is where we have a beginning and unfair advantage. Part of the business model in and of itself revolves around supply and demand economics in every corner of the globe that we have touched so far. Supply is drastically low relative to demand. Therefore, finding guests to stay at, at your locations, that’s that’s a non issue. Let me explain. Most people, when I when they’ve only been thinking about vacations or sunny spots. What most people don’t realize is this is more of a temporary housing business. And there are about 65 different use cases that we’ve identified. Let me give you an example. Today, as you guys are hearing me somewhere in the city right now, somebody’s house flooded. They called their insurance company. That insurance company outsourced the claim to a third party provider. That third party provider has one job find that insured that homeowner a place to stay. That place to stay is a short term rental. And when you understand that, you know, I know that in every city. This is going on all the time. And those are some of the most profitable stays because those are typically 30, 60, 90 day days, simply because of how long it takes to clean up something like a. Pipes bursting or mold. Yeah. But these aren’t things people are thinking about. But also today, when you watch the news or the next time you hear of a hurricane or tornado. Fema gets involved. Those displaced homeowners. Need a place to stay. And guess where they stay. That’s also a short term rental.
Stone Payton: [00:16:52] Hmm.
Jermaine Massey: [00:16:53] Now, let me go one more step further. You’ve heard of this small little country by the name of Ukraine, right?
Stone Payton: [00:17:00] Yes.
Jermaine Massey: [00:17:02] All of those refugees. That came to the United States. Need a place to stay. Do you see where I’m going with this?
Stone Payton: [00:17:11] Yes.
Jermaine Massey: [00:17:13] And so it’s so much bigger than just put your property on Airbnb. And this is how it works. In fact, Airbnb is the low price leader. And don’t get me wrong, you can make some you will make decent money there. And that’s how I started, because I didn’t know any better. I’ve learned a lot since, you know, since we started because I have insight into so many different locations, but it don’t. If you’ve ever watched a movie and you’ve ever seen the internal shot like they’re shooting and it looks like they’re in somebody’s house, it’s because they’re in somebody’s house. They don’t build it all the time. Right. And and you know what that is? That’s also a short term rental. But those are like tens of thousands of dollars per day as a movie set. So there’s so many use cases for what we do that it’s built and then it’s built with the same basic system that undergirds everything. So it’s it’s almost unfair, right? Because like I said, supply is so low that demand is so high. It’s one of those things where you don’t have to be good in order to be present. You just have to be present. Period and you’re you’re wishing or receiving an overwhelming tide flow of people who have demand.
Jermaine Massey: [00:18:35] We’ve got many stories, many examples of when someone’s in the process of bringing new inventory to market. They haven’t even taken photos yet and get reservations simply because, again, there’s a process to it. There’s a way to market and target who it is that you’re looking for so that you don’t just get anybody because there’s still safety screening and security to consider. But once you’ve got those things figured out, like I said, it’s just a matter of bringing more and more inventory to market and having the necessary systems and technology in place to be able to do it. And that’s actually what’s created this opportunity. It’s technology. I mean, technology is slamming into real estate in such a way that many traditional landlords aren’t aware and I’ve been saying this for years, but I’ll say it again, every landlord is going to have to contend with short term rentals, whether you like it or not. You can get mad at me, you can resist, but they’re coming and you’re going to have to find a way to deal with it. Otherwise you’re never going to maintain the occupancy that you need in order to do what you’ve always done because it’s changed.
Stone Payton: [00:19:42] I’m so intrigued with this wholesale model. So to play this out, let’s say that that I bit the bullet with my brother and we bought a little place here in North Georgia to rent out to people who are going to this is a great area for people who like to do the mountain biking and and we did that now could on the other side of the table could we be seeking out people like you to just go ahead and buy those 365 days? There must be a marketplace.
Jermaine Massey: [00:20:09] 100%.
Stone Payton: [00:20:10] Yeah. Never even occurred to me.
Jermaine Massey: [00:20:14] Yeah, 100% that I’ve got people in and we get those emails. All the time.
Stone Payton: [00:20:22] You’re like Gordon Gekko. You’re you look at 100 deals a day.
Jermaine Massey: [00:20:26] It’s it’s a lot. But because, again, we just happened to be the intersection of solving a number of problems. Landlords have vacancy. That’s expensive. That’s a problem. People need a place to stay temporarily that’s clean, safe and affordable. So we just bridge both of those gaps really is was what it comes down to. But and we do so in the while providing jobs to the local market. So I mean the number of people that we have to employ for any one reservation and you start to multiply that out across not only one operator who has two, five, ten, 20 locations, but all the students that we come across, it can be it becomes massive and it’s exciting to be honest.
Stone Payton: [00:21:19] So at this point in your career, what are you finding the most rewarding man? What are you enjoying the most about the work?
Jermaine Massey: [00:21:28] So this. Hmm? You’re trying to make me cry. All right, so I’m not going to do that today. No. What it comes down to is I, myself, I am. I’m autistic, and I have ADHD. And recently, one of my students came to to to me to tell me that his son had recently been diagnosed. Same. And first he said thank you for letting me know because he had no idea what it was. And I had been the only person who he had ever run into who said anything. But then he followed that up with. And thank you for teaching me what you’ve taught me, because I see he’s he’s he was prior in the military and as he was exiting the military, we helped him in his late twenties or early thirties to put himself in a seven figure position so he could transition out of the service into civilian life and has a seven plus figure business now. But what he was grateful for was I have the resources. That’s what he said. He said. I had no idea how expensive this was. But thank you, because I don’t have to worry about being able to provide anything for my son. That’s what I do right there. That’s what I care about. I know. Because when a when when a father has the resources, he will lead his family. I know that. I believe that. And all the way through, up and down.
Jermaine Massey: [00:23:16] And the resources isn’t just the money. It’s also the time because we spend and trade so much time. That’s what we were taught, to take one of our most valuable assets and trade it for something that’s less valuable. But if you learn how to use and leverage assets that you build, build, buy, own and control. To create your income. Now you have both. You have monetary resources, time, resources, and now you get the freedom of choice. And that’s what he’s experiencing him and his wife are experiencing today is that they get to choose how to best take care of their son. And and that’s why we’ve got a collection of stories like that. In fact, we just had our first single black female across seven figures this year. And I’m just like, yes, this is awesome. Right? And notice I have to get so I got to get specific now in order to because of the number of people that we’ve been able to help, it’s like it’s not just the first person to ever. It’s just and that’s what’s rewarding is being able to gift to somebody something that I discovered uncovered by a tragedy. Right. And if but for the my lungs and all this other stuff that happened, I would have never discovered that. And then today I get to give it to other people.
Stone Payton: [00:24:49] Wow. All right, man, where can our listeners go to learn more? Start tapping into your work and maybe even have a conversation with you or someone on your on your team, whatever you think is appropriate. Website, email. I just want to make sure they can tap into your work, man.
Jermaine Massey: [00:25:04] Yeah, we’re at Cash Flow Diary on all socials at Cash Flow Diary right now. The one of the ways to get up to speed really quickly is to get what we call our blueprint. It’s cash flow diary slash blueprint. What I will literally do, we pre made an eight hour training that’ll teach you the beginnings from A to Z. You will be able to get at least one unit with the blueprint and that is absolutely at no additional cost. So just go to cash flow diary dot com for such blueprint download it now don’t just download it, watch it and then do what it says.
Stone Payton: [00:25:45] Well, Jermaine, it has been an absolute delight having you on the show this morning. Thanks for investing the time and the energy to share your perspective and your experience. You’re doing tremendous work and we sincerely appreciate you, man.
Jermaine Massey: [00:26:01] I, I appreciate you because I know what it takes to produce content. We’ve been doing it for a while and and you’re doing it and you do it with with joy. So I hope your listeners appreciate it, too, because at the end of the day, us helping each other is how we get it done.
Stone Payton: [00:26:18] Hey, man, absolutely. My pleasure. All right. Until next time, this is Stone Payton for our guest today, CEO of Cash Flow Diary, Mr. Jermaine Massey, and everyone here at the Business RadioX family saying we’ll see you in the fast lane.