LUR 4 | Short Term Rentals


Setting up a successful business requires building a good team and processes. This is especially true and essential in the business of short term rentals that undoubtedly comes with a lot of moving parts. Managing a quick and efficient turn on your properties enables it to get back on the market to keep working for you and providing exceptional value and customer service for your guests. On this episode serial real estate entrepreneur, Cash Flow King and the CEO and Founder of Cashflow Diary, J. Massey, discusses with Lisa Hylton the importance of playing the infamous Cash Flow Game by Robert Kiyosaki and building multiple businesses in the real estate industry including his current venture short term rentals and how this strategy can provide extensive cash flow for investors!

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Scaling A Short-Term Rentals Business With The Cash Flow King, J. Massey

Scaling A Business With Short Term Rentals

I am excited to bring to you our guest, J. Massey. He is the CEO and Founder of Cashflow Diary, a training and development brand for building short-term rental entrepreneurs. Before the Cashflow Diary, he raised capital and invested in traditional real estate, both 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 the hundreds of traditional long-term housing units. When one of his students asked him what he knew about the world of short-term rentals, his answer was not very much.

Once he 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. He has shifted his Cashflow Diary brand to focus exclusively on building and training short-term rental entrepreneurs. Now, he’s building a community of thousands of likeminded people from sixteen 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. I am excited to have J. Massey on. Let’s get started with the episode.

I have on my show, J. Massey. He’s been investing in real estate for many different years and has done a variety of different ways of investing in real estate. These days, his focus is on short-term rentals. Now, we have him on the show and we’re going to go through his story of how he got started in real estate as well as his experience playing and hosting the Cashflow game. Going into short-term rentals, how it works and giving readers a brief overview of what this strategy is all about. Without further ado, thank you, J. Massey, for being on my show. I appreciate it.

Thanks for taking the time and being brave to produce content.

I have been inspired by you as I’ve said before in leading up to this podcast. I’ve done a bit of your Cashflow Diary theory that you have like the different training. I followed your YouTube on the way in which you play the Cashflow game. That has inspired me in real life to play the game and host the game for other people. It’s a delight to have you on my show.

It’s fun. I recommend everyone to play it. It sounds like it’s a game, but it becomes a lifestyle after a while. It’s something that more people should be exposed to.

To kick off this interview with you, I’d like to get into your story and how you got started investing in real estate.

What’s interesting about that is many people ask me about real estate and do I like real estate, which I always find it humorous is because I don’t care about real estate in and of itself. What I care about is cashflow. I care about cashflow because that’s something that can happen even when you can’t physically do something. That’s how we got introduced to our need for an income or for cashflow, was simply because my wife at the time was pregnant and she had a condition known as hyperemesis where she was unable to eat and drink simultaneously.

I had a punctured lung and I was born with asthma, so I couldn’t walk and talk without fainting. We were having to sell personal possessions on eBay and squatting in bank-owned property and do all kinds of things that neither one of us had ever envisioned would be, “This is our life.” It was presented as a solution, which was ironic because at the time when my friend comes and says, “You should get involved in real estate investing.” I’m like, “I’ve got a credit score 398. My electricity is about to be cut off. What are you talking about?” That was the situation.

For whatever reason, I still listened because oftentimes as human beings, what we can do is when someone presents us with an opportunity like maybe someone shared this podcast with you as an opportunity. The first thing that we do is we look at the title and go, “Real estate, I don’t have any money. I don’t have that.” For whatever reason, we talk ourselves out of something before we even understand what it is. For some reason, this time I did not do that. I said, “Okay, but you’re going to have to show me because I got no money. I got no credit. I got nothing. You have to show me literally how to do this with what I have, which by the way is nothing.” They did and that’s what happened.

LUR 4 | Short Term Rentals

Short Term Rentals: Oftentimes, human beings talk themselves out of something before they can even understand what that something is.


I learned something very important and this is one of the reasons why the Cashflow game is so important because as a human, you can learn any game if you’re taught the rules. I was never taught the rules in elementary, primary school or kindergarten, etc. I was never taught those rules. The game, Cashflow, began to teach me the rules and understanding how real estate worked. I was like, “What you’re saying is,” and my wife came up with this and she was like, “How is eBay for houses now?” Because that’s what it was.

There was a time when a company would say the store was going out of business and what we did was we would go and buy their going-out-of-business inventory and I’d put it on eBay. Mind you, I did nothing to it. I exposed it to more people via eBay and make money. We started doing that same thing with houses. I’m like, “I had no idea this was possible.” That’s how we got started with wholesaling. We did about 200 of those transactions and we earned between $2,000 and $26,000 each. That began to change our world because you’ve got to understand, squatting in bank-owned property, we were told you can’t own a home. You have a foreclosure. All of the things, I’m like, “If that isn’t true, what else isn’t true?” That’s how it started.

Going from that, after your stint into wholesaling, what other aspects of real estate did you also go and get into?

What happened was when we were doing all those transactions, we did them all quickly and it was like, “This is great.” We got introduced to the taxman and that began to create a different need. I’m like, “That was fun, but how much was there? That’s not cool. I want something different.” It became what I call our house collecting phase. I’m like, “Is there a way to not pay anything?” How many houses does it take to do that? That’s what started it. I was like, “Cool,” and we started owning and keeping the houses. I wanted to be more efficient with my time because it can take a lot of time to close a deal. If I close a deal, I might as well get more bang for the time by going into apartment buildings. We started owning the mortgages on houses. We ended up in commercial real estate with cell phone towers and anything that could produce cashflow was the idea. It put us in a position in which at around age 38, we were able to effectively be retired with a large portfolio and not a whole lot to do.

At this point, for people who are reading and for myself as well, what advice do you give to people as you have transitioned into different asset classes and playing different real estate in different ways? What advice do you give to people as they transition through different types of investing?

The main thing to realize or at least the thing that is by far the most important is understanding the basic concepts. I’m from a military family. I tend to make military references because it’s the world I understand. That means things like a single point of failure. When you begin to perceive risk in life differently, you can make different choices. I had to go through the transition of, I was told the same thing many of us were. Go to school, get good grades and get a job and that’s one source of income. That’s all that is and it depends on one person, me.

I had the fortune of being taught vis-à-vis our circumstances that if something happens to me or my wife, our income is gone. We can’t guarantee that something like that won’t happen again nor do I want to live in fear of that happening. What else can I do? Being willing to face the fact that there’s greatness inside of each one of us. It’s already yearned to come out. In fact, I would submit that there’s a number of people who are reading right now. The reason you have read not only this far but to all the other episodes before and all the ones coming is because that greatness is seeking expression.

For me, it took my life getting much worse to be willing to take the risk. That’s probably the biggest caution. That’s the biggest warning, comfort kills dreams. Your comfortableness kills the dream. That’s the thing. I don’t know what I would have done and be willing to do the things I do if those things did not happen. If I was not forced to go out and meet strangers because mom growing up said, “Don’t talk to strangers,” but if you’re going to be in business, you’re going to talk to a lot of strangers. That’s how it goes. The comfort, be very afraid. If you feel like you are comfortable, “I got all that figured out, I already know that,” when you hear that, if you are saying that to yourself or in your head, you’re in trouble.

You touched on the Cashflow game earlier, but I wanted to dive into that a little bit deeper. I know based on some of the content that I listen to, which is that someone had invited you to their house on a Black Friday to play a Cashflow game and that’s when you played your first Cashflow game.

That’s the thing. The true-life lessons, the things you need to know. Why do we get to play a board game to find it out? Do you know how random that is? I happened to like board games. My wife happens to like food. They were offering both. We did not know what it was or what was about to unfold, but lo and behold, it suddenly there were answers in the board game and I’m like, “What is this?” That’s what happened. We didn’t go there with any intention. I thought, “Whatever the game is, it will be great. We’ll go on about our business.” We were not seeking transformation. It just happened and there we were. Suddenly, we were confronted with like, “If I can do it in a game, what if we tried to do this in real life? What would happen? Let’s go find out.”

That’s what we did. I know it sounds very elementary. There were no charts involved. There was not any deep due diligence research study. It was, “The cards in the game say this, let’s see if we can find something in the newspaper that looks similar.” If we would do it in the game, let’s do it in real life. I was like, “Okay.” My wife ended up finding a number of them. I’m like, “That worked. Let’s keep going.” I want to say it was more complicated than that, but it wasn’t.

Why do you still play the game now?

I’m still learning. I’m still getting better. The constant never-ending improvement, we’ve all heard that before. I’m also a father. My kids need to play the game. My wife continues to play. Probably the hidden secret that most people don’t even understand, they have no clue. Everyone’s out there trying to get leads and increase their ROI and conversion. One of the best ways, especially for the people in real estate or financial services and nearly any business, your business, your customers need a better relationship with you.

Cashflow is something that can happen even when you can't physically do something. Click To Tweet

You can’t get to know them better and they can’t get to know you better than by playing a board game. It sounds crazy. Yet there’s so much that you can learn by watching how other individuals play a game. There’s so much that they learn about you and you learn about them. The relationship changes at that point, especially because of this one phrase, “He or she who’s willing to educate the market, dominate their market,” period. Because you took the time to educate them on something that they may previously have considered to be too complicated, but you made it simple vis-a-vis a board game. You now transition. You become more of an advisor. You take on a different role and we all have that one teacher and instructor somewhere on some subject that suddenly lit you up around something you were previously dead too.

Whether that be math or history or God forbid, chemistry but you get what I’m saying. You can become that person for other people. From there, you build your business, whatever that may be. In this digital world where it’s all click and quick, one of the things that we have to be cognizant of as small business owners is that relationship is everything. You may have 20,000, 30,000, 40,000, 60,000, 70,000, 100,000 or 250,000 on your email list. You better get good at keeping a relationship with 250,000 people. You may have 2 million, 10 million downloads on your podcast. It’s wonderful. It’s still a relationship that you better figure out how to make sure you nurture and take care of them and all of those things because that’s what’s necessary in order to make it happen at the end of the day.

It’s an awesome responsibility but at the end of the day, it’s so secret because you can set it another way. If you can get access to the board game, which is also saying, “If you’ve got access to Amazon,” and they’re everywhere, you are in business. Get the board game, bring people over and play. See what happens and then do it again next week and the week after that. Over time suddenly, you’re like, “I’ve got people asking me to come to hang out and play a board game.” That’s amazing. I thought there were no leads or something. It’s amazing what’s possible.

At this one, I want to dive into the short-term rentals, which is the way in which you play in real estate primarily these days. To start off, the business model of how this works essentially.

Understand for me a lot of it always will come down to some logical numerical decision. There are some numbers somewhere that were run, that told me what to do. If you do the math right, math will tell you what to do. I know I used the math word and for those of you who like, “Not math, please.” I won’t give you a word problem this time. With that being said, that’s also the answer. When I looked at the return on investment and time, these were all things that spoke very loudly because running a large portfolio is great. It’s wonderful. It’s a great way to build wealth. What most people won’t tell you is that it’s a horrible way to build income until all of the debt services are gone.

Until that mortgage has retired, you are fighting deferred maintenance all day, every day. That is the fight back and forth. What’s broken now? How can we repair it and when do we need to repair it? You’re asking your financial team, “Can you come up with a schedule that’s going to make sure that the cashflow runs specifically this way?” It is a masterful orchestration of making sure that all of those things continue to happen so that you can still provide clean, safe, affordable housing to people as you originally intended. That’s the juggling act that is the best way of putting it.

What happened is that was inspiring me to find more active income because, on the tax side, we succeeded in being able to have our adjusted gross income be where taxes became a non-issue. I was like, “That’s interesting.” It suddenly felt like a wasted benefit. I started looking for ways to increase active income with the standard taxable stuff. I’m like, “We got this down, so let’s get this higher.” One of my students at the time came to me and simply said, “We were able to raise the capital. Thank you for teaching us how to do that. We didn’t do what you said.” I’m like, “What do you mean?” That’s usually the sign of something bad.

They said, “This is what we did and we’d like you to look at the numbers because this what we did is now competing with what we currently do,” which at the time was student housing. I’m like, “This is competing with student housing? Student housing is rather profitable. What are you talking about? I need to see some numbers.” When they showed me the numbers, I stared at them. I was like, “I know what this sheet says this. The sheets say that’s every month. Are you sure?”

They looked at you and they’re like, “Yes.” Because see they weren’t sure if I was like saying, “Are you sure” as in that’s good or “are you sure” and it’s like, “We have a problem.” I am not intentionally, but I was still silent and staring. They were sitting there waiting. Eventually, if you can imagine, I’m at my favorite restaurant. The food is on the table. The bratwurst is staring me in the face, but I can’t take my mind and my eyes. My attention is on this spreadsheet. I’m like, “I have never seen anything like this.” That’s what I told them. I was like, “You don’t even understand what you have.” That’s how it started.

You’ve got to understand my email inbox, even still to this day, is not short on people with offers and deals and all of these things. This was the only time I have looked at something and went, “Not only is this good, but I’m going to do it too. I’m going to help you do it better.” That’s what happened. I was like, “It’s all in the numbers. For those of you who are the spreadsheet kind and you like math, I’ll say this quickly, and for those of you who have yet to understand some of the languages I’m about to use, that’s okay too. You can look it up on Investopedia later because that’s what I did. If you can imagine increasing your top line revenue by at least double while increasing your operational expenses by no more than 10%. You can imagine what that does to your net operating income. It becomes insane.

When you do that and look at your debt-service coverage ratio, instead of trying to squeak out 1.25 or 1.2 or whatever your lender will let you get away with, you’re starting to look at 2, 2.5, 3, 4 and it becomes a non-issue because it’s like, “We can make that work.” When you start to put those metrics together and you start trying to figure out if you’re going to value the building on a GRM level or cap rate or whatever you’re going to do, you suddenly see the value that’s created in the marketplace and it’s hard to ignore.

To dive a little bit into this, someone says, “I’m interested in doing short-term rentals.” What would be their first couple of steps that they need to do in order to get into this business?

That’s again where the understanding the why’s, how’s, the deep dive in the training and stuff, that’s what we go down to. When it comes to the first steps, what’s important is to understand the ‘why’ we suggest. Before you buy the property, we want you to lease the property. There’s a number of reasons for that because you’ll get a higher return on investment. At the end of the day, it’s a higher return on investment, but it’s also less risky. When you think about the process that you go through to buy a piece of property, given your experience at the time you take it on, it’s crazy. Here’s what I’m saying. I’m saying take a twelve-month risk and explore this idea around real estate.

What most people have been sold, what media would have you believe is, “No, don’t do that.” We want you to take a 30-year risk with the same amount of experience and spend so much more money in the down payment alone. Please do this. This makes more sense. This is what we’ve been sold. We do it. I don’t know what you save up and depending on the geographic area you live in, 20% of a house would be a lot of money. If you’re out here in LA, that’s multiple hundreds of thousands of dollars and you have one property. Set another way, you have one unit of production. That’s important because when you’re dealing with the macroeconomics that all of us are dealing with vis-a-vis inflation, etc., you have to earn money faster than they can print it.

When you only have one unit of production and $200,000, I promise you, if you do the math, your $200,000 of cash in the down payment, you’re not seeing that for a while unless you refinance. You’re not seeing it again. It’s going to be years, possibly a decade. When you take that same $200,000 and put it inside of a short-term rental portfolio and you’re leasing the locations, even in Los Angeles, even in expensive places, you can still knock down somewhere between 8 to 12 short-term rentals, depending on the square footage. You have twelve-units of production.

LUR 4 | Short Term Rentals

Short Term Rentals: Organizing cashflow is a masterful orchestration of making sure everything continues to happen so that you can provide safe, clean, affordable housing to people as you originally intended.


They would be all leased?

Absolutely and you could have 8 to 12 of them. Now, you’ve got twelve units of production. Here’s what happens. The cashflow that comes back, your $200,000 is likely back in your hands, anywhere between 10 and 18 months, somewhere in that range and you’ll have your $200,000 back.

That $200,000 investment would probably go into leasing fees and maybe furnishing the properties because it’s short-term.

Everything that you do for your own home in order to make it functional is the same thing you’re going to do here. It’s the same. You got to buy a bunch of blenders. You got to buy in some cases, depending on your geographic location, refrigerators are included with leases, sometimes not or whatever. You’ve got your refrigerators. You’ve got your couches and dining areas. You got whatever it is the customer that you are looking to serve desires. That is what you need to have and need to make sure it is there. There is no version of getting around that. There’s a lot of logistics around that piece. It’s often outside of a lot of skillsets. It takes a team to pull this together because I’m not a designer. I hire designers. I don’t want to assemble furniture. We hire them too. I’m not a painter, so we hire painters. There are so many things that go into that.

It’s 100% a business because you’re setting up this legitimately a business. Real estate is a business, but for a lot of people, if they’re buying one house, it can feel like, “I’m buying this one house and I’m renting it out.” Whereas if you’re going to get into short-term rentals and you’re having 8 to 12 units, you’re going to need to be creating a business that you’re hiring people and having systems in place.

That’s where we excelled and that’s what I was able to help the individuals who were showing me the concept. That’s what I was able to bring to help them scale with all the systems because when you’re running a portfolio, hundreds of units, cell phone towers, and all this other stuff, but I live in California. All that stuff was in Colorado, Georgia, Michigan, Tennessee, etc. The one thing I understood was systems. I got that part down. I don’t have to go. I know how to execute all of this stuff without physically being present. You bring that to the short-term rental industry, and what begins to happen is lives transform and you bring a financial understanding that I’m not saying don’t buy a property. I’m saying when you buy property, it’s important to understand the commitment that you’re making and given your stage of life right now, I’m sure buying property isn’t going to produce the highest return on investment. We broke it down into a three-phase system. In the beginning, you’re in phases one and two. You can get to phase three and you probably can get there faster than you think.

You said you break it down into a three-phase system. What are your phases?

Phase one is to simply get your first short-term rental. There is so much involved. I know many of you are thinking, “It’s easy. I know what my house needs.” I’m like, “You do,” which I don’t think you’re aware or present to how much stuff it takes. Now, you’re designing a house for a specific purpose other than for yourself. Things that you like may not necessarily be conducive to running the business for a quick and easy example. I see this all the time, especially with the amateurs who are out there. They’ll put an Alexa or a Google home in their unit because they’re like, “I would like this. This would be great.” Don’t do that because, in most States, that can easily be considered a violation of privacy, but it doesn’t occur to you because you’re thinking, “It’d be wonderful” or a sound generating device or a speaker. You got to think a lot of stuff through in order to make sure that it works. You’re setting the whole thing up, making it work so that ultimately it becomes a space that somebody else feels like they are at home even though they are not.

Would short-term rentals and Airbnb be the same thing?

Short-term rentals are more the industry, that’s what we do. Airbnb is a marketplace. Unfortunately or maybe fortunately, if I was a stockholder in Airbnb, that’s one thing because I would love for people to misuse my company name as a verb. It’s not a verb. It’s a marketplace. What they do is they arrange where buyers and sellers meet, people who have time to sell, look and meet up with the people who have a need to buy time at your location. That’s what they are. Short-term rental expands well beyond the marketplace of Airbnb. We’ve identified 45 different use cases, well-over 65 different marketplaces. Depending on the customer that you choose to serve, like for some of our students, Airbnb is not even a place that they go.

One of the things that come to mind is the laws that a lot of cities have put in place for Airbnb rentals. Sometimes people might think Airbnb and maybe short-term rentals group them in the same box when it comes to city regulations, cutting down on the way in which you can use your property to rent it out on a short-term basis.

As you can imagine, this is something that comes up often. I’ve had the fortune of dealing with this not only in the United States but because this particular business model works across the globe. We’ve got students in multiple countries and I’ve helped them through it too. First, you have to understand that in general, every ordinance I have had exposure to with minor exception when you read them, they’re saying, “Here’s where and here’s how we want you to do it.” That’s what they’re saying.

When you read the headlines and if you trade on that, the newspaper says, “Airbnb banned.” It’s wonderful. If that’s as far as you go, that’s also what creates the opportunity for those of us who are willing to be a little bit more diligent and to go read the ordinance, number one. Number two, when you do read the ordinance, you got to understand what they’re calling, what each city, what each locality is calling a short-term rental. With that being said, let me say it a different way. For all of you who are used to traditional landlording in real estate, here’s an idea for your acceptance.

When you begin to perceive risk in life differently, you can make different choices. Click To Tweet

At the end of your one-year lease or three-year, whatever you do, typically those leases convert to month-to-month contracts. There’s nothing wrong with that. It’s never been contested. There’s nothing wrong with putting your property that same one on a marketplace like Airbnb and setting a minimum stay of 30 days. There is no jurisdiction across the globe that I am aware of where you cannot do that because the definition of short-term rental typically is tied to length of stay, which is defined differently in various locations but none of them as in none at all, even where you live, say something about 30 days or more. Just because you’re using the marketplace of Airbnb or whatever, that doesn’t automatically make it a short-term rental.

With what I’ve said, there isn’t a person who’s reading this that can’t already execute the strategy. What you don’t know is how do I find that person that’s only looking for 30 days or more? Is there enough business for 30 days or more and all of those other things? I get that and the answer is yes. All of that can be handled, done and taught. What’s also missing from the understanding is that the short-term rentals concept has been around since the Civil War period in the United States because it used to be a requirement to get a mortgage, said another way. If you didn’t have an income-producing property on your primary residence, the bank would not give you the loan because they wanted to be sure you could make the payment.

The concept is not new. Technology has lowered the bar, which made it available for more of us. That’s normal. Technology outpaces governance and the pendulum swings both ways. There’s a time where it’s going to swing way too restrictive. However, at the same time, I’ve been watching it swing back the other way as locations like Anaheim, California, for example, begin to walk back some of the things that they said, “No, this, that and the other.” No one ever talks about how those two very loudly because that’s not news.

This is a lot of good information. If the readers want to learn more about short-term rentals or learn more about you, in general, like the way you’re investing, what are some of the ways that they can learn about that?

I would invite any of you, type Cashflow Diary, into any piece of social media. You’ll probably find us because that’s where we are. We have a podcast. We have all of those things. As an exercise, one of the things that I want you to go experiment with because oftentimes we don’t realize how close we are. I want you to go over to It’s a calculator. You answer the questions and the calculator will tell you how many short-term rental units you need to retire. That’s what it will tell you. A lot of people who have gone through it are finding out that it seems reachable. That seems like I can do it and it is not as many as I thought. I invite you to find out one, for that surprise, second because it’s hard to pursue a goal if you’ve never defined it and now you can find out for free.

LUR 4 | Short Term Rentals

Short Term Rentals: Everything that you do for your home in order to make it functional is the same thing you’re going to do for the properties you’re investing in.


One other question I forgot to ask that I remembered is if someone on step one, on phase one, which is to get your first short-term rental, approximately what is a budget you would say most people need to have to get started. Granted they can get creative but still.

To be clear, will you have people started with as little as $500? Yes. Am I trying to set that expectation for you? No, that would be irresponsible. I tell everyone $25 per square foot, period. That is what you should estimate especially if you are starting with a property that is not your own. Here’s what I’m saying. A property that is not your own and you’re talking about leasing the entire space. Those of you who are trying to go, “I can take this corner of my house, in my room.” You’re going to have a different lower and often startup costs than what I’m talking about here.

What I’m talking about is what we have proven to be in over sixteen different countries, the most reliable, most scalable, most predictable cashflow possible, which is a property that’s not your own outside of your house that you can duplicate the result of over and over again. I tell people to start at $25 per square foot and over time, as you develop your contacts, your vendors and all this other stuff, that number will come down. That number should come down. If you’re following our course material, it’ll definitely go down. As a first go, $25 per square foot, which puts it in reach for most people on credit card regardless of where you live, which is crazy to say. If you’re in California, New York, Hawaii, expensive places, the idea of getting started in real estate on a credit card was never even a thought in your head until now.

Thank you so much for your time. I appreciate it.

You’re quite welcome. Thank you for continuing to carry that flag and reach people that want to make a change and do something.

Thank you.

I enjoyed this episode with J. Massey. I felt it was inspiring listening to his story and how he got started into real estate. I feel like it’s a great lesson as well as a testimony for people out there who might be interested in getting started and thinking that they don’t have any money. That’s a part of these series that these episodes are under, which is all about exploring all the different ways people play in real estate and highlighting that there isn’t just one way to play. Similarly, his strategy, which is short-term rental investments at this time, is illustrating how you as an investor can evolve and change over time and that’s okay.

That’s the beauty of life is that you want to try and do different things. It’s a part of you growing as a person. It’s illustrating that you’re growing because as you grow, you evolve and decide that you want to try and do different things. His experience playing the Cashflow game and being a role model as well as someone who is instrumental in the society for other people because I know for sure that I’ve watched his Cashflow games on YouTube and have been inspired by them. They’ve helped me when I decided to host my Cashflow games here in LA. They’ve been great blueprints in terms of things that I could do and approaches that I could take. Two other things that really stood out to me from my conversation with him is that he spoke about how we all have greatness within us and that greatness is always seeking expression. It’s beautifully told and a part of that is having the courage. I hope that you feel encouraged by this episode to go out there and to embrace, trying different things and trying the things that are speaking to you in your life. Comfort kills dreams.

You need to know how to execute all the stuff that needs to be done without being physically present. Click To Tweet

Also on the same wavelength, but it’s so powerful. As someone who is putting themselves out there like myself here on this show, I can tell you that it’s not always comfortable. From it, I am growing a lot. I learn a lot about myself and I meet a lot of people who in turn, inspire me. Through that, I continue to grow and evolve and it’s beautiful. I hope that you enjoy this episode. I look forward to bringing more content and more real estate investors with amazing stories about how they have gotten started in real estate to help inspire you, educate you and provide you with the opportunities to level up your real estate investing game. Have a good one.

Important Links:

About J. Massey

LUR 4 | Short Term Rentals

J. 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.

Interested in connecting with J. Massey – he can be contacted as follows:
Phone: 949 682 7468
Twitter: @cashflowdiary
Facebook: /Cashflowdiary
Linkedin: in/cashflowdiary
Instragram: @cashflowdiary
Youtube: used/cashflowdiary

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