
FREE ebook: "How to Buy Your First Investment Property" - https://bit.ly/3NJLquO Ready to escape the 9-to-5 grind and achieve financial freedom? In this episode of the Rich Dad Real Estate Show, Jaren Sustar sits down with Connor Cushman, a...
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Jaron Sustar
Welcome to the Rich dad real estate show where we talk about the good news and bad news of real estate, hosted by yours truly, Jaron Sustar. Down in the show notes you will find my free ebook, how to buy your first investment property here at the Rich dad company. Our goal is to give you the tools to escape the rat race and achieve financial freedom. And my ebook is going to help you do that through real estate. So today we have a very special guest and good friend of mine, Connor Cushman. Connor is an absolute legend in the short term rental space. He was in the corporate world, left it, now does real estate investing full time. Not only does he buy properties for himself, but he helps others get into the short term rental space as well. Connor, welcome to the show.
Connor Cushman
It is great to see you, Jaren.
Jaron Sustar
I am excited to hang out with you today. We've been talking offline because you're working with me to help me buy a short term rental. And so I'm excited that you're going to get to share that knowledge with all these listeners because I only partner up with people who know what they're doing and you know what you're doing. So I can't wait to extract everything that's in your brain today and give it to the listeners. So you obviously got to the short term rental space but if I remember correctly, before that you were working a W2 somewhere in the tech space. Maybe you were doing tech sales, something along those lines.
Connor Cushman
That's right. That's right. So I actually just completed my two year anniversary of leaving my full time job. I had what I considered to be my dream career coming out of college, joined a company called LinkedIn that many would be familiar with, owned by Microsoft, great benefits, amazing people, super cool opportunity that I was very excited about. And one of the things I like to highlight from my story in the context of the rat race that we talk about in the rich dad, poor dad book is the idea that everyone's version of what the rat race feels like is different and unique. And one of the things that one of the feelings I had in my version of the rat race in what I thought was my dream career was this feeling of guilt that I was aspiring to more despite all that I had in front of me. Right. Um, and so for some people the, the experience of the rat race is just a really crappy job or manager who's abusive or just bad situations and, and obviously maybe guilt isn't the problem and it's really just like mental health and getting to the next Opportunity that's a little bit safer of an environment. But then I think for many people and maybe the majority, it's this like tension, this internal tension, this guilt of feeling like well I should be grateful for this job or the market, you know, the macro economy is kind of unstable and uncertain. I need to just put my head down and be more focused on my work and more, more grateful for what I have in front of me. But there's this pull towards like self employment, freedom, escaping the rat race and pursuing your higher, higher potentials is often how I think about it. So while I had this amazing tech, tech career, a great situation, leaving, leaving that, that experience and getting into short term rentals has been life changing for me. And I think the power of just one or two short term rentals unlocking that for people is really exciting to me and something that, that really filled me.
Jaron Sustar
How do you think is the best way for folks? Because I believe that what you said with the guilt thing, that's a great point. I think a lot of us struggle with that. How do, how do you think is the best way from somebody who you may still be battling this because I think we're all on this journey but to feel content and thankfulness for what we do have while still pushing forward to achieve more.
Connor Cushman
Yeah, I don't think I'm qualified to.
Jaron Sustar
I beg to differ. I say you are. You're a psychologist along with an investor. Didn't you know that?
Connor Cushman
Fair enough. Well, so yeah, to some degree when you, and you know this, when you get into the just roaming the self employed universe, you deal with a lot of these internal struggles and you're forced to kind of reflect tactically like writing things down and just journaling. Even though I don't do that enough, the times that I do just kind of write down the things that are going well, the things that I'm struggling with just being present and like pausing for a moment, getting away from the phone addiction that I struggle with and probably many do, and just being present for a moment is a moment where I feel more connected and more present and more grateful for where I'm at and, and then kind of optimistic and, and solution for like solution thinking about the problems and the tension that I feel to get to that next level. Right. So if that's a tactic that maybe just is a, it's a basic thing but, but overlooked by, by a lot of people I think, I think, yeah.
Jaron Sustar
I think you're spot on. And one of the things that's helped me throughout my life And I battle with it. I think anybody who's driven and wants more. So if you're listening to this, you're driven and you want more. And so you're going to battle this at some point. One of the things that I have learned is that the gold is in the journey. And so when you reach the destination, whatever that is, hey, I want two short term rentals or I want 20 rental properties, I want to do $200,000 worth of profit and flips. It is great to achieve it, but it just lasts for kind of like a split second. I mean, you could talk to any athlete, for example, in the NFL if they play all season and win the Super Bowl. Winning the super bowl was great. But when they get back and reminisce, they talk about the journey along the way and the fun they had with the guys and everything they learned, all the trials they went through. And I think that is the same with us. And it's almost like a catch 22 because we talk about escaping the rat race and we want to because if not, we're going to be in this hamster wheel that goes on and on and on. But if we, if we live every day with an escape mentality, I feel like that can almost put us into fight or flight constantly to where we're forgetting to learn and enjoy the lessons, which is the real gold along the way. And so I would encourage folks, strive, set goals, just like Connor's talking about, but take every day step by step. Once you've set that goal, you know what you want to achieve, you write it down, you've put a plan to put it into place. Now we can be present and focus on those daily tasks that are going to get us to where we want to go. And then we don't live a miserable life because so many people chasing success like people think miserable people are only, you know, poor folks who don't have anything. I would argue that there's maybe not just as many, but there's a lot of wealthy people who are miserable every single day because they don't take time to be thankful for what they currently have. And in this season of Thanksgiving, you know, I think it's pretty darn important.
Connor Cushman
Yeah. Just to, just to add to that, I heard a comparison once of, of a beautiful life is like a canvas, right. Made up of a million different brushstrokes. Right. So to your point, those brushstrokes in our life would be moments with friends or service to in on behalf of others or exercise running. For me, it's running on the local greenway trail or playing with my kids or having that successful closing or that launch of a new short term rental that I'm really excited about. And if I go Back to my W2 time, I do think I did an okay job of allowing those moments, that part of my journey, to be still a beautiful part of my canvas of life. Right. There were amazing friendships that I made with my coworkers or super smart people that I learned from. There were corporate, corporate job benefits that I took advantage of. I got Lasik surgery because my company offered Lasik or I maximized my 401k which, you know, my 401k loan was what I used to fund my first STR so we could get into that. So, you know, there are definitely opportunities in your current environment in place to have beautiful moments and have a fulfilling life as you work towards that next step. Right.
Jaron Sustar
Love that grow where you're planning. So there's all these different directions you could have gone with real estate. So you wanted more. You knew from reading books like rich dad, poor dad, you knew. Real estate, like many of us, was a great vehicle to get you to financial freedom. It's been proving itself literally since the beginning of time. Those who bought property since the world started and held onto it, they tend to get wealthy. And so you were smart enough to say, you know what, I don't need to reinvent the wheel here. This thing works. So which route am I going to take in this thing? And we, you know, I get the opportunity to interview a ton of people and a, a lot of different areas of real estate. I mean, we got commercial, we got storage, we got single family, all these kinds of things. You chose short term rental. How come?
Connor Cushman
Yeah, so I think what's cool about short term rentals is it's kind of this. I think of myself as a, as an entrepreneur that got their start in real estate. And I don't know what that looks like long term, but I suspect that I will have many entrepreneurial ventures and I just so happen to start in real estate, which I think is a great place to start. It's this half step towards entrepreneurship in many ways because it's so stable and so predictable. There's so much data that you can look at and feel confident that you're taking a pretty calculated risk with low downside. Specifically short term rentals, I think is like. Because I have a couple of long term rentals too, and that was actually my first, you know, real estate purchase, so to say. But short term rentals are kind of this next step in the progression towards business ownership or operations. Right. So a short term rental is a business that lives on top of real estate. And to think of it otherwise, I think is, is wrong to, and I think many people go kind of make the progression from long term rentals to short term rentals, not anticipating how much of an exponential leap it is in terms of operations and stress and hats to wear and roles to fill. And it really is, it's, it's this business that um, and, but because of that, because you're filling all these different roles and doing so much more work, you're supercharging the cash flow and income opportunity right to the tune of 2, 5, 10x. So I saw that I, I decided I was willing to put in that extra level of work and take that extra level of risk to get to a cash flow and freedom place quicker. And that's certainly been the case. It's, it's been, it's just totally supercharged my journey towards financial freedom in one to two years instead of five to ten. Right.
Jaron Sustar
Yeah. I think short term rentals are definitely known at least if you're in the real estate space for producing more cash flow than traditional long term rentals have. And when you are able to play in that space, then it sets you up for a lot of success down the road from the cash flow perspective. But also when you look at the short term rental space. You tell me if I'm wrong, Connor. It seems as though most short term rentals are in decent areas. So like where you may buy a traditional rental, like a lot of my long term rentals are in what I call B to C class areas. They're good areas. But a lot of these short term rentals are in potentially A class areas. And so you're able to capitalize not only on increased cash flow, which we'll talk about here in a second, but also potential for more increased appreciation because you're in the really nice neighborhoods in our neck of the woods here in the Southeast. You're in, you know, the beaches on Florida or you're in the mountains in Georgia, or you're in Gatlinburg and Pigeon Forge and all those areas and they usually go up in value over time because people are going to continue to go over there. So what makes a short term rental jumping back to cash flow? You know, you hit on it. It's a business on top of real estate. Why does it generate so much more in income compared to a long term rental?
Connor Cushman
Yeah, you know with, with long term rentals you have the ceiling and you have this, you have this predictable range of. Say you go on Rentometer or Zillow and you look at comps and you say, okay, I'm buying this house and it can rent for 2 to 2,500. That's pretty much it. There's not a whole lot you can change there. Whereas with short term rentals there are great data tools that you can use to name a couple data Rabu Air, DNA, STR Insights, Awning. These are data tools. You can go look at markets and analyze addresses and you can see that there are these properties that you pay 3, 4, 500,000 for and there's, there's revenue potential of 90 to $100,000 because you have these massive population groups that are spending their weekends, their holidays and even weekdays for various reasons, crashing at a cabin for a night or two and they're paying 2, 300 bucks a night and they love it. And they're, you know, in a market like a North Georgia for example, which is kind of my home market. There's not hotels in Blue Ridge, Georgia and Ella J. Georgia and Dahlonega, Georgia. And so they, they want to stay at these cabins. There's a number of reasons why they come to the area and if you do it right, we're definitely in an industry that is professionalizing and maturing. So you and I talked a couple years ago and we talked about the adoption curve. We're further along the adoption curve. There's more institutional money, there's more professionalized organizations that are operating at scale and the comp. The bar is being raised. The standard for design, furnishing amenities has continued to be raised. However, still lots of opportunity for someone that understands that to come in, operate well and drive massive, massive cash flow.
Jaron Sustar
We'll be right back with Connor Cushman.
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Jaron Sustar
Rich Dad Real Estate show. We're talking about the good news and bad news of real estate with Connor Cushman. Connor, before the break, you mentioned that you bought your first property with a loan off of your 401k that you had built up while working a W2 job. So there's a lot of ways to fund real estate deals. I teach. Most of the stuff I teach is how to buy real estate without having to use a lot of your own money or without having to leave a ton of your own money in the deal or getting creative if you are going to use your own money to where you can make money on your money or you can get it back quickly or we can just use somebody else's money. And so I love creative ways of buying real estate. And what more creative way than to leverage a 401k to do it? So walk us through that process.
Connor Cushman
Yeah, real quick. I think it's important to highlight the, my favorite principle from rich dad, poor dad, which is my, my poor dad said I can't afford it. And my rich dad asked how can I afford it? Right. So this, this question of how can I think is like if there's a takeaway, I hope it's that, that you ask the question how can I? And repeat that question as you go through the process to continue to find creative solutions to your problems. And my wife and I, Aubrey, were laughing because it's Christmas time. We were thinking back to eight years ago when we were first married. We had no money, we were both students, we had some debt and I still wanted to create a great Christmas for her. And I remember just to give you an example of kind of how my brain works as far as like finding scrappy ways. I remember I would go on like these gift car trading websites and I would buy like gift cards at like a 25% discount and then get them in the mail and then put them together and then wait for the sale at the store so I could get the thing I wanted to get Aubrey for Christmas. Right. And I've kind of always just been like that way. And I think there are probably lots of people that are like that, the scrappy and creative. And I think if you're that, just try applying that to like real estate. It's not that different. Just find creative ways to make it happen. So I remember I was at my job, didn't have a ton of cash and I was asking the question like, how can I find a way to get some money down? And so I discovered for my first cabin, so I discovered 10% down second home loan. And I discovered that I had the option through my employer to take a 401k loan. Pretty straightforward process. Not that hard if you have a decent 401 program. And sure enough, it was a couple clicks of a button and that money deposited into my checking account payments back to myself into my 401k tax free. Right. So it's not a distribution, there's no penalty, it's just a loan to myself and then a low interest payment. I'm actually still paying that. I think I have a year left, Very low payment, super low interest rate and the interest is actually just paid back to myself anyway. Right. So just total hack of a situation that I think many people have access to and don't realize. And that was how I funded my first deal. And I will say if I want to highlight, I'd like to highlight like a mistake I made in. And it actually goes back to the question of how can I and me not asking that question. And that was the first deal I went for. I missed out on probably $500,000 by missing out on this deal. And it's because I did not ask the question how can I enough in the process, right? So my first short term rental I put under contract with an agent and right away, within a week or two, the sellers decided they no longer wanted to sell, which is a problem. I really wanted to buy, they didn't want to sell anymore. I think they started to realize like, oh, we are getting rid of a really good property here. But it was, it was their obligation to sell the property to me and I pushed forward. Looking back, you could argue that maybe I should have just let them back out if that's really what they wanted. Ultimately, they got that outcome anyway because I lost the deal. But the mistake I made is that my lender just moved too slow. We missed our timelines and he did not fund in time. So on the day of closing he was a day late and I lost the deal.
Jaron Sustar
Wow, that's insane.
Connor Cushman
And I could see that coming from like a week or two out. And I had, I asked the question like, how can I make this work? I think I could have gotten a solution and I could have kept an amazing deal that is now, yeah, $500,000 of lost opportun there in terms of equity and cash flow. And that one still stings. The good news is I moved forward very quickly. And I think the first deal I'm talking about with the 401k loan, I think I had under contract within two to three weeks after that. But I did not ask that question, how can I enough? And I wish I would have. And since then I've tried to apply that as much as possible.
Jaron Sustar
Why do you think a lot of people don't go through that thought process of how can I? I feel like a lot of people, as soon as they hit, like they may listen to things like this, they may read books, listen to other podcasts, they kind of get started on the journey and then they hit that first roadblock and then it's kind of like, I guess it wasn't meant for me or oh, I'm not ready to push through this. I don't know what that is. But I do know this much that anything worth having Usually takes some work and takes some sacrifice. And I know for me, and I'd love to hear your perspective. All the deals I've done, I don't know if there's just been a very smooth one. You know, from actually finding the deal, to analyzing the deal to finding funding for the deal, to closing on time, to due diligence. Like, that's why I say this a lot. 1 percenters are called 1 percenters because 99% of people give up before they get to the pot of gold, but just keep going. Like, how do I ask that question? How do I get it done?
Connor Cushman
It's messy. It's messy. It's always messy. I do a lot of deals for myself and other people and it's like, I just tell people now, like, just be prepared on the day of closing or the day before where something's going to fumble right in front of the finish line. And it's always messy. And success in real estate at scale or success in any business venture at scale is just solving a lot of problems. Like, just solving a lot of problems. And so I think people get overwhelmed with like a big problem and they don't do the, they don't do the, like, take a bite of, out of. Take the bite of the elephant one bite at a time. Eat the elephant one bite at a time. Right. Um, another thing that I was thinking about, and just to touch on briefly, a principle from Tim Ferriss's book Four Hour Workweek that totally changed my life, is the idea of fear setting and actually writing down the consequences of inaction. And so it's this idea of framing your fears or problems or decisions that you're afraid to make and actually writing down like the worst case scenario and what that looks like and what you could do to solve that worst case scenario. And likewise, you should also sit down and say, okay, I'm evaluating buying my first short term rental. I'm really scared of these things. If this doesn't happen, then I'm going to be bleeding $2,000 a month. And if I'm in that scenario, what will that look like? Like, how would I navigate that? What. Who, who could I go to to get help? Or, you know, so that's fear setting on the action side. Then there's the inaction side. And you say, well, what if I don't ever get a short term rental or don't ever do my first deal? What does that look like? And actually write out, like, what that feels like. What would you, what would you, how would you feel about Yourself, how would you feel about like how you're achieving your full potential as a human being or how would you feel about your current financial situation and feeling, you know, stuck? And so writing those things out I think is helpful to then help you kind of like clear the brush and just like walk the path forward that you know you need to walk.
Jaron Sustar
I love that. I love that exercise, putting that down on paper of what, what's the worst case? Because usually the opportunity cost of inaction is greater than the risk of action. I always tell folks you gotta. When it pertains to real estate, you've got to brainwash yourself to truly believe that it is riskier for your future financially to not invest in real estate than it is to invest in real estate. And I truly believe that because I've been on both sides of the coin and I know if I would have kept doing what I was doing a decade ago and was in the same spot, financially, life would be way riskier today than it is with the large portfolio and the flips we've got going and everything that's working that allows us to do as a family what we want to do. But it took years of action and years of saying, yeah, there is some risk. How do we mitigate that? Like you said, write it down, figure out how to mitigate it and then go take action. It really is somewhat simple. I don't want to dumb down what can be a complex process, but with the right team members and the right knowledge at that point, it's just you going and taking the step and it is worth it. And I would encourage you that your future self is actually sitting there banking on you right now, making the right decisions to change the trajectory of your life. So I want to get into a little more of the tactical talk when it comes to short term rentals. When you were evaluating buying a short term rental, what are you looking for? Location wise, number one. And then what are you looking for? Just on a macro view and we can dive into some of the micro numbers. But macro view revenue versus purchase price.
Connor Cushman
Yeah, absolutely. So I was listening to your, your recent episode with Michael Alfonte and I think he did a really good job of breaking down. He and I share a lot of similar thoughts on looking for that 20% annual revenue relative to purchase price. Right. So $500,000 cabin, you should be projecting a likely scenario of a hundred thousand dollars. Right. So that fraction is revenue on top, purchase price on the bottom. Look for 20% ratio. Right. If it's a little less and you Want to, you want to have ways to just like quickly filter through lots of deals. So that's a good rule of thumb. If it's a little less, but the property is really interesting or unique for some reason, you could still dive in. If it's more, then you probably want to spend extra, extra attention there. From a tactical standpoint, it's more important than ever to think about how do I stand out and separate myself from the pack. So not all of us can like Michael Alfonte, go for the million dollar properties and that's okay. I actually think I'm kind of different from him in that regard that I've kind of stayed smaller and most of my clients stay sub 750, sub 500 and that's okay too. Right. And it might just be that you, you don't, you're not trying to get to a million dollars in revenue a year. You might just want 2 grand a month or $1,000 a month and you just want 13 or $400,000 cabin. That's going to help kind of give you some breathing room. Right. And so $300,000 cabin, 60k in revenue. You're going to always run a scenario analysis. And that's one thing that I really harp on with my investors is when it comes to short term rentals, there's so many things that can swing revenue, including things you can and can't control. Right. And so you have to be prepared to look at multiple scenarios and say going back to kind of the fear setting thing, I think it's likely that we'll do 60k. I think there's a decent chance we do more. I also think there's some possibility we do less. And I'm comfortable with this set of risks and probable outcomes. Right. So that's kind of the revenue side. I have a free calculator that I'll, I'll have on my website for you to share that people can use. It's not perfect, but just get a calculator going, start running numbers and it becomes pretty, pretty routine after you do it a few times.
Jaron Sustar
Yeah. And you do a good job. Just when I work with you as a client of breaking down, hey, this is kind of worst case scenario revenue. This is what we think it could do. And then this is best case scenario, you know, if you crush it with all the amenities and everything that goes into. So what are you seeing that's most important right now? You said, hey, you need to stand out. And I think, I think that's important. You mentioned, you know, we're in late in the adoption phase of short term rentals right now. We're later in the adoption phase than we were just a few years ago. And there's been some bad press on short term rentals in recent years. Like short term rentals are dead. They're dying. They can't make any money. You know, I've had this conversation with a number of folks. I know you've had it. That's just not true. I mean, it's just not true. It's the hospitality business. It's not going anywhere.
Connor Cushman
Right.
Jaron Sustar
It's going to have more competition, which we're seeing, but it's not going anywhere. And so knowing that we're in that later adoption phase, what have you seen with your properties, with your clients, properties that have allowed you guys to keep that revenue going strong while some of these bad operators have taken a hit?
Connor Cushman
Yeah, absolutely. So I think the key is, and number one, I'll say I've closed. I closed on three new short term rentals this year and they're my best performers by far. And you would think that. Oh, but you bought properties years ago when interest rates were 3% or whatever.
Jaron Sustar
Yeah. Aren't interest rates? Isn't that the only thing that dictates returns, Connor? That's what everybody thinks.
Connor Cushman
Yeah. So people are shouting, you can't do Airbnb anymore. I can't afford it. I can't find good deals. It's this poor dad mentality of I can't. And then the question is, is really just asking, how can I, how can I find a deal that performs? And, and I think asking that question and sitting with it relative to your situation is it's important to kind of sit in that and look at your situation, where are you located and find those opportunities. So some examples of that would be finding that pocket of the market where maybe there's only 10 competitors instead of a hundred and it's just the next town over, next to an area that's really popular. Or finding that pocket of the market within the bedroom count. Maybe you're in Helen, Georgia, and there's three bedrooms like crazy, but there are only a handful of one bedrooms. And so that's your, that's your pocket of the market to, to compete and dominate. And maybe it's actually a pretty high bedroom count, but you look at the operators and you see that there's just not a high level of operations that you can come in and dominate and be the best. And then other things outside of that would be like structural design, like unique exteriors. So there's a lot of popularity, a lot of growth in the area of tree houses and tiny homes and container homes and a frames. If you have the skills and willingness to kind of navigate that development process, the sky's the limit in that space and then maybe a little bit easier and more accessible to the average Joe who's getting into their first deal is just really going hard at the amenities and trying to find these little unique things that no one else is doing in your market. And you have to have, you have to have some vision and, and you have to be, be in tune with what people like. And, and to some degree that's, that's a skill that is maybe hard to quantify, but some examples of that would be like a barrel sauna with a glass wall at the back that looks out at the view. Right. You don't see a lot of those in a lot of markets or one that I recently did. I'm giving away my secrets. But like an outdoor pool, soccer table where you've got, you know, a 5 by 10 turf area with some soccer balls and soccer pool outside. Right. That's pretty unique. You do a couple of those things. Stack that on top of good across the board in terms of furnishing, management, pricing, all that, you're going to have a star that shines and you're going to get the revenue that you want. And that makes sense. Right?
Jaron Sustar
People are looking for an experience when they go. I mean, I think it's good to put yourself in the shoes of the buyer, you know, or the renter when, when you're looking at these things. And I try to do that through all phases of life, not just in the real estate space, but like how are these people thinking, what are they wanting when they're leaving their house, going on vacation? And most people want an experience and you know there's going to be those people who want the cheapest, that's fine. You know, I don't like playing in that space. It's usually a race to the bottom. Let them go buy their cheaper or rent their cheaper place to stay for their vacation. But there's a lot of people who want, who want the greatest experience. Do you think it's fair to say as a blanket statement in the short term space it's better to either have a large home, four, five, six bedrooms, or a smaller home, one bedroom, two bedroom, compared to like a three bedroom or maybe a four bed. Is that a blanket, is that a fair, blanket statement to say, or you think it's dependent on market.
Connor Cushman
I think that highlights the importance of having like either an investor mentor or a realtor who really knows their stuff in the market that you're targeting. So it is market by market because yes, if you would have asked me that question about North Georgia over the last three years, I probably would have said, yeah, get out of the middle and stay small or big. And I still probably would say that. But I think everyone's been saying that now for three years and maybe the opportunity, it's dynamic. Right, so. So you'd actually have to take a closer look at the three bedroom. Funny enough, I have a three bedroom in Blue Ridge, Georgia, which is like the opposite of what I tell all my clients to do because I bought it before and then it got competitive and so I kind of encourage people to go elsewhere. But my three bedroom Blue Ridge, Georgia cabin, which is a market that a lot of people like to hate on too, by the way, and other podcasts and Facebook groups for being oversaturated. I'm up year over year on my annual revenue by about 15% of that property. And part of that is reinvestment and design and amenities. But also goes to show that if you do it right, you can win in any pocket, in any segment. And if you're, if you have someone that's like in tune and dialed into the market, they can point you in the right direction. So that's that, like, how can I find the right deal? Is that like who not how question too? Right, like find the who. Find the person that can guide you to the right, the right property.
Jaron Sustar
Which leads me to Connor. If anybody listening wants to get guided to their short term rental by you, how can they get a hold of you?
Connor Cushman
Yeah. Thank you. So you'll put cushmanholmes.com in the link. That's a easy little page to connect with me on different social channels. I'll have some free resources there. I created two free resources specifically for your listeners. There are two self evaluations that you can download, print, write them down. And I know that's old school, but I think it's good to do that sometimes. And the first one is should I invest in a short term rental? And the next one is should I self manage my short term rental? Which is a very important and overlooked question. Get those questionnaires if you're starting from zero and just do that and then connect with me wherever you are in the process. I help people connect with expert STR people all over the country. So if I can't service you in my markets. I've got connections and I also offer coaching and consulting and all that jazz too, just to help people wherever they are in the process.
Jaron Sustar
Love it. Connor, thank you for being old man, one of my favorite people. Great dude, you understand real estate and you're an absolute stud at short term rentals. So thank you for coming on today and we'll talk soon.
Connor Cushman
Thank you, Jaren. I appreciate you, man.
Jaron Sustar
Thank you for tuning in to the Rich Dad Real Estate show today. Again, go down to the show Notes, grab that free ebook so you can learn how to escape the rat race through financial freedom, and I'll see you next week.
Connor Cushman
This podcast is a presentation of Rich Dad Media Network.
Rich Dad Radio Show Episode Summary: "How Short-Term Rentals Build Wealth Fast"
Release Date: December 12, 2024
In this compelling episode of the Rich Dad Radio Show, host Jaron Sustar engages in an insightful conversation with real estate expert Connor Cushman, delving deep into the lucrative world of short-term rentals and their potential to accelerate wealth-building. The episode seamlessly blends personal experiences, psychological insights, and tactical strategies, providing listeners with a comprehensive understanding of leveraging short-term rentals for financial freedom.
The episode kicks off with Jaron introducing Connor Cushman, a seasoned professional who transitioned from a corporate career in tech to full-time real estate investing. Connor shares his journey, highlighting the pivotal moment when he left his stable job at LinkedIn to pursue his passion for short-term rentals.
[00:41] Connor Cushman: "I left a dream career at LinkedIn to dive into real estate investing full-time, and it's been life-changing."
Connor opens up about the internal conflicts associated with leaving a secure job to pursue entrepreneurship. He emphasizes the unique feelings of guilt and tension that many aspiring investors face, as they balance gratitude for their current situation with the desire for more significant financial freedom.
[01:12] Connor Cushman: "Everyone's version of the rat race is different. For me, it was the guilt of aspiring to more despite having a dream career."
Jaron echoes Connor's sentiments, discussing the importance of appreciating the journey rather than solely focusing on the end goals. He draws parallels with athletes who value the experiences and lessons learned along the way, underscoring that the true wealth lies in the daily steps taken towards financial independence.
[03:27] Jaron Sustar: "The gold is in the journey. It's the lessons and experiences along the way that truly matter."
To navigate the psychological hurdles of entrepreneurship, Connor advocates for practical methods such as journaling and fear-setting. He references Tim Ferriss's concept of fear-setting, which involves outlining the worst-case scenarios and devising strategies to mitigate them, thereby clarifying the path forward.
[21:36] Connor Cushman: "Fear setting helps you frame your fears and find solutions, clearing the path to take action."
A significant portion of the discussion centers on the financial advantages of short-term rentals over traditional long-term leases. Connor explains that short-term rentals can generate significantly higher cash flows due to higher nightly rates and increased occupancy in desirable locations.
[11:32] Connor Cushman: "Short-term rentals are a business on top of real estate, allowing for cash flows that are 2, 5, or even 10 times greater than long-term rentals."
Connor shares his strategy for assessing the profitability of short-term rentals, emphasizing the importance of location and revenue-to-purchase price ratios. He recommends aiming for properties that can generate at least a 20% annual revenue relative to their purchase price.
[25:18] Connor Cushman: "Look for a 20% revenue ratio relative to the purchase price. For a $500,000 cabin, aim for around $100,000 in annual revenue."
In a maturing short-term rental market, Connor highlights the necessity of differentiating properties through unique amenities and exceptional design. From outdoor pools to specialized features like barrel saunas, standing out can significantly enhance revenue potential.
[28:44] Connor Cushman: "Unique amenities like a barrel sauna or an outdoor soccer table can make your property a standout, driving higher revenue."
Connor delves into innovative financing methods, sharing his personal experience of using a 401(k) loan to fund his first short-term rental. He explains how this approach allowed him to invest without significant upfront capital while keeping the loan interest directed back into his retirement fund.
[16:37] Connor Cushman: "I used a 401(k) loan to fund my first cabin, paying myself back with low-interest rates, effectively hacking the system to finance my investment."
Reflecting on his journey, Connor admits to early setbacks, including losing out on a significant deal due to lender delays. He underscores the importance of persistence, creative problem-solving, and continuously asking "How can I?" to overcome obstacles and seize opportunities.
[20:01] Connor Cushman: "Success in real estate is about solving problems. When faced with setbacks, you have to ask, 'How can I make this work?' and find solutions."
Towards the end of the episode, Connor provides listeners with actionable resources, including self-evaluation questionnaires to determine their suitability for short-term rentals and options for coaching and consulting services. He encourages aspiring investors to connect with him for personalized guidance.
[34:02] Connor Cushman: "Visit cushmanholmes.com for free resources and to connect with me for coaching and consulting to guide you through your short-term rental journey."
Short-Term Rentals as a Wealth-Building Tool: Short-term rentals offer higher cash flow potential compared to traditional rentals, especially when located in high-demand areas and equipped with unique amenities.
Psychological Readiness: Overcoming internal struggles, such as guilt and fear, is crucial for transitioning from a secure job to entrepreneurship. Practices like journaling and fear-setting can aid in this process.
Creative Financing: Leveraging resources like 401(k) loans can provide the necessary capital for real estate investments without significant upfront costs.
Differentiation in the Market: Standing out through unique property features and exceptional management can significantly enhance revenue and occupancy rates.
Persistence and Problem-Solving: Success in real estate requires continuous problem-solving and resilience in the face of setbacks.
Connor Cushman:
Jaron Sustar:
This episode serves as an invaluable resource for anyone looking to venture into short-term rentals as a means to achieve financial freedom. Connor Cushman's blend of personal anecdotes, strategic insights, and practical advice offers a roadmap for aspiring investors to navigate the complexities of the short-term rental market successfully.