Return Home >
Sign up and get updates sent directly to your inbox.

Subscribe to Real Estate Investing Unscripted on Apple Podcasts, Google Podcasts, Stitcher, or Spotify.

This week's episode features fellow podcaster and investor extraordinaire, Jen Josey!

Jen hosts the REIGN ( Real Estate Investors Growth Network) Podcast: A place for real estate investors to "share their badassery" and expand their reach in the community. She's known for keeping it real with investors about her personal experience in the industry, and the perfect guest to have on our show. 

Make sure to subscribe to the podcast to keep up to date with all of the latest episodes of the Real Estate Investing Unscripted Podcast, from your friends here at Upright!

How do you like your content?

Listen! (OR subscribe wherever you get your podcasts!)

Read (transcript below)!

Brendan: Welcome back to Real Estate Investing Unscripted, where we get real with real estate investors and experts throughout the industry. I'm your co host, Brendan Bennett, and with me is your other co host, David Dugan. And David, our guest today, a true Jill of all trades. She does podcasting, blogging, she's an investor, she's a real estate coach, and she always brings the energy, and we're super excited to have her on.

David:  Yes, and in addition to that, she's actually a client of what was formerly Fund that flip and is now upright. Here's your promo shot. There we go. Given how much fun Jen is to talk to and the fact that she does podcasting herself, why don't we just kick it over to you, Jen, and allow you to, uh, kind of give us your own intro here and, and give us the, uh, the background on yourself. Jen, welcome to the podcast,

Jen: David and Brendan. Always good to see you. I remember the first time I hung out with you, Brendan. It was a much prettier scene. We were in... Cancun, I think it was.

Brendan: Cancun.

Jen: Yes. Very good. 

Brendan: for the tab retreat. 

Jen: the Tab Retreat shout out to my, my brother from another mother. Terrence fair. so a little background on me.

First of all, thank you for having me. This is an honor. I saw some of your other past guests. I was like, Oh my goodness, I'm hanging with the big boys now. Um, so my first passion in life was I was a school teacher. I taught middle school music for 16 years, and then I woke up one day, realized I hated children.

So I went to an equally abusive industry and I chose health insurance because everybody loves health insurance. And unlike my first passion of teaching, I just, I could not connect with the whole aspect of corporate America. I'm really glad I had that experience. It's made me better at what I do, but I just, I couldn't.

I needed a change. So I was 40 ish and, uh, I was up late one night. There was an infomercial. We were just talking about gurus and there's a guru on TV and I was like, Oh, let's just do it. We were, we were just talking about football too. And you have the armchair quarterbacks that know how to fix everything in the game.

Well, we were the armchair designers and we watched all the HGTV shows and I was like, we can do that. So we signed up for this program. We paid a ton of money and never looked back. that's how I got started in it. we start with Jolific Homes and I, I love the whole concept of naming companies because I feel like people who do initials are super boring.

So and I love your, the name of your new company. One more time.

David: Upright.

Jen: And it's because that's the where you want your money to be going up and to the right. 

David: That is correct, Jen. Absolutely. Haha. Hahaha.

Jen: So, um, we started the education program, paid a lot of money, didn't look back. I was able to quit my job. Corporate America job within eight months. We made our money back. We started Jolific Homes. So our business name is our last name Josie plus the word prolific and we call it Jolific. And from there we bought our first short term rental which started our rental Jolific Properties and then we opened up the Acorn Agency, which is an investor friendly agency for realtors. And I was really kind of missing the whole teacher hat throughout all this. And so that's when I created RAINN, which is the Real Estate Investor Growth Network. And it started as a mastermind and has evolved into my podcast, which huge.

I'm in my fourth season now, just last month, I been hit the three year mark. And so I started my fourth season and loving it. So thank you very much. It's I'm telling you, it's challenging, but how often do you all release your.

Brendan: We are every other week right now. So we're recording, uh, every 10 days and then getting one out every two weeks. But, uh, we're only, what, 15 episodes in, you and I? So, to be four seasons in, Jen, that's, that's no small feat.

David: We're learning from the vet today.

Jen: it is a lot, and what a great gig this is to hang out with experts in our industry, ask them anything you want, and just, I feel like I'm spoiled because of who I get to talk to all the time, and now I get the opportunity to be on your show, so thank you all very much for having me.

David: You're welcome. And I would say likewise, right? It's um, you know, as somebody who is, is in real estate, but in the grand scheme of things, green to real estate. And Brendan I know has, you know, kind of his own portfolio that he's been building. it's not only fun to talk to our guests like yourself, but it's also super valuable and educational for us because it, you know, it's, it's on the job training for us.

We get to pick the brains of some of the best minds in real estate. It's awesome.

Jen: Love it. Agreed.

Brendan: And Jen, before we start to kind of dive into some of the different parts of real estate that you're in, cause you have a, you have a hand in a ton of different of the different value streams, uh, within real estate. You mentioned that you and your husband are in business together and I think it'd be cool just to get a backdrop of what's that dynamic like.

Um, do you, does one person handle more the finance and accounting side? Is someone focused on acquisition? Just give us the rundown of how you and your husband manage the business together.

Jen: Well, I have on my office door, says Jen Josie, HBIC. Do you know what the HBIC stands for? 

David: Yeah, 

Jen: Am I allowed to say that word? So,

David: Oh yeah, 

Brendan: you can say that. 

David: Say whatever you want.

Jen: working in a partnership with me is probably a lot to handle, but anyway, I'm the head bitch in charge. And so, I married Vance on purpose because he is an accountant and I was like, Oh, that is the one thing I can't stand. I'm just kidding. There's other reasons why I married him, but, um, he is on the accounting side.

He is a good test taker. He has his GC license. I told him one day, I'm like, Oh, you know, I've always wanted to sleep with a GC and You know, I, I was hoping you say which one, but instead he got his GC license, bram, bram. And, uh, he also got his real estate license. And so he does all the paperwork side of things.

I'm the looks and the mouth behind everything. So, but I can crack a whip when it comes to working with contractors. That's the whole teacher part of me. just making connections. Everything is, is more my side, but he is. It's definitely the brains behind a lot of it and my huge support system.

Brendan: Very cool. Yeah, we've, we've um, I've gotten the chance to work with Vance a few times over the last couple years on the, from that flip and upright side. And as you said, very, Easy going guy, someone that seems like very dependable on the construction and the accounting side, so, definitely understand how that dynamic works for you guys, for

Jen: absolutely. And I'll give a pointer to anyone out there listening. If you work with your spouse, even though you share a toothbrush holder together, we still every Sunday at five o'clock have weekly meetings and it's huge and it's literally like a spreadsheet and we take our laptops off and out, excuse me, and we're just sitting there crossing each other and entering in the same spreadsheet together.

But, you know, our wins for the week, what's our goals for the week, um, what's our stucks? you know, whatever it is, you know, catch up from last week. And it's great. We've been doing this for five years now. And I can literally say, Oh, back in 2019 in June, we had so many projects coming and what were we doing marketing wise?

So we can go back to that spreadsheet for that year, go through the tabs because each one has the Sunday date on the bottom of it and go through that. So if anybody's listening, that works with their spouse. It's huge to do that. And you may think they know everything that's going on, but they truly don't.

You really need to have that one on one connection there. And at the bottom of the spreadsheet, we do what's called a Bravo Boost. And so you have to say one nice thing about the other person. And I will literally put my, I'll be waiting in the cell to see what he puts in his cell first before I hit enter and let him see what I put.


David: you have to find a new compliment every single week?

Jen: it gets tough. It gets tough. I'm telling you. Yes, 

Brendan: You gotta recycle them 

David: at some point, right? Yeah, yeah.

Jen: it's got to be business related because he'll like, Oh, she did a great job organizing this party. I'm like, Nope, has to be business related. So

Brendan: So, Jen, you mentioned, you know, your 16 year background in teaching, and then I know you do some teaching in the real estate world as well, so I'd like to dig in just a little bit there. I think a lot of people that are getting new into real estate, maybe people that are listening to the podcast right now, they're like, I need a coach, I need a mentor, I need someone that's going to be able to help me.

some of those services are free. Some of those services are paid. Uh, some of those services are really, really expensive depending on where you're at. If you're... Awake at 2 a. m. You might see a guru course for 50 grand promising you the world. So what I'm curious from you as someone who's experienced as a real estate coach, what should someone be looking for in a real estate coach?

What are some things that maybe stay away from and, just overall your experience as a coach over the last handful 

David: of years?

Jen: great question. Uh, so Brendan, I, I'm telling you, let me start with what not to do. So if you have someone in your community that is a step ahead of you, a couple steps ahead of you, um, Do not say to them, Hey, can I take you out for a cup of coffee and pick your brain for an hour? Let's just not go there anymore people, please, because our time is much more valuable than a cup of coffee for that hour.

Instead say, Hey, I hear you just got that project and it looks like there's a lot of stuff that needs to be hauled away. Can I come and help you haul away materials? Yes, absolutely. Ask me whatever you want and, uh, and bring beer. So it's, it's one of those things where be polite on how you ask. So, what to look for.

It's really dependent on what you. What you're learning styles are there's a lot of programs that are literally they're evergreen where it's you watch video and They tell you something and then and some people they learn great that way There's others where it's all in person live events and you have to do a lot of traveling and that gets expensive Think about things like that There are the ones who have the Facebook groups that are a lot more interactive and sometimes you don't have the time to be there at those times when they're doing recording, stuff like that.

So that's kind of the start of it to see what's a really good fit. But I think the key here is if it's too good to be true, it is most likely too good to be true. So if it sounds that way... then I would not even go for it. You know, get rich quick scheme. None of this real estate business is get rich quick by any means.

So I would, you know, run far from those people who over promise and under deliver. And there's a ton of them out there.

David: There's a ton of them. We've all been to the weekend boot camps where it's, you know, Take control of your life. Get rich quick. I'm going to teach you how to make a zillion dollars in a weekend. Um, so I appreciate your, your realistic approach and, and transparent approach to that. you have the, the coaching business, obviously, but you're still maintaining your actual real estate business.

Talk about that. How are you managing both of those at the same time? And is that a challenge to juggle both of those businesses at the same time? Or do you guys kind of have that on, on cruise control at this point?

Jen: excellent question. Um, I actually, I coach for a coaching program. Um, I work with Tarek El Moussa, who was one of those that I would watch on HGTV. Like, I can do that. And he is one of those that I love everything that he, he's a little ADHD. He's going to kill me for saying that, but he gets these great ideas.

He's like, let's do this, let's do this. But he is such a genuine person and his coaching program really meshed with me and he gives us a lot of space to teach, you know, real stuff. He's, you know, way up here on HGTV and has all these people doing stuff for him. So he forgets sometimes how hard it can be.

So that is super important. Also, when you're looking for a coaching program to see who's working for that person, but there's a lot of opportunity there. And so when I started coaching to go back to your question, That's when Vance took over a lot of the, management side when I started doing coaching, which is.

It's typically Monday through Wednesday and then Thursday, Friday is when I'm doing podcasting. We also in our business are now focusing more towards multifamily. I am kind of over the single home flips, even though I just bought another one cause I was like, Oh, it's such a good deal. And guess who's funding it?

You all. Yay. Thank you. Um, you know, coaching and it's just one of those things where we've gotten into a groove in the very beginning when you're writing offers, you're writing 25 offers to get your first one accepted. Now we're to a point where we are really skilled at writing the offer, making those connections, really winning over that deal.

So out of four offers that we write, we could typically get two of those. It's pretty much 50 50 percent close. So that also frees up a lot of time for us for me to do more of the coaching. Podcasting, blog writing, all that fun stuff. I'm actually creating an online course right now too. So my brain is a little brain dead, which is why I slur my speech starting this.

And I swear I'm not even drinking. I'm just, I, I had a late night with my, my first football game of the season. So anyway, I digress. So I hope that answers it.

it's to a point where we are in our business, we're getting better at it, so it's not taking as long to do certain things, which frees up our time to do the coaching.

David: You mentioned one thing that I was fascinated about, and it was going from making the 25 offers down to, you know, four offers, and how you optimize that side of your business to free up time. How did you do it? I mean, that's a loaded question, right? There's probably a million answers, and it probably takes years of experience, and, you know, some other...

Advice from other investors, but like, I'm, I'm curious, what were the, the things that you kind of boiled down to get that so efficient?

Jen: there's really not like a specific answer for it. I just kind of get more of a feel for projects, we've been around it for so long now. And... When it's an off market deal, for example, and there's a lot of competition. say it's a pre foreclosure and they're getting five or six postcards a week.

They get your postcard. My postcard is different. It doesn't say, Hey, I hear you suck at making payments. Call us today to, you know, save your, save you from bankruptcy. Mine is literally generic thinking of selling. We buy your home as is we offer a fair price and we can close on your timeline. So very easy.

Generic term or verbiage and then our pictures on it, so they end up calling us and then when we go there and do the walkthrough again, they I build rapport with people. I will find out the price they want before we even leave. I I'd rather do things like that in person. There's so many people out there that do things online and I scares the hell out of me to do that, even though we did buy something out of state recently.

So Something that was a 12 unit. So we're, we're happy about that. But, just really honing in your skills and knowing, oh, they're definitely going to want this. Or I can tell that they've had a lot of people give them offers. I can say, listen, I may not be your highest offer. But I'm going to be the easiest transaction you've ever had.

And that's really how we've gotten several of the off market ones. As far as the on market, you just kind of get them tweaked enough to know that, Oh, they want a quick close. They want this, you know, just to really find out what their pain points are. And that's how we've really just shrunk it down to get about 50 percent of the offers we put out there.

Brendan: And Jen, are you guys sourcing a lot of your deals through your own lead gen wholesale efforts? I know you guys have mentioned before the use wholesalers as well. What do you think that split is right now versus how much you guys self-identify versus ones that come via wholesaler?

Jen: So I do postcards myself. That's it. and I like inbound leads. I do not chase down my deals. I hate cold calling. In fact, we were at an event and Tarek's like, Hey, we're going to all cold call. I'm like, Oh shit, I've never cold called before. He's like, what? I'm like, I've never ever done it. So, um, so we have inbound leads.

I would say the split is probably about 25 percent is coming from wholesalers, about 25 percent come from referrals. I have an online presence, so people know, you know, I've built my credibility online, so people just bring me deals, which is fantastic. 25 percent comes from the MLS, which is a great place to buy right now because stuff is sitting a little bit longer.

And then the fourth one would be my direct mail campaign because I love those inbound leads. A. B. M. Always be marketing. Big believer in it.

Brendan: So Jen, we're going to transition a little bit into a very like deal heavy, uh, side of the podcast where I want to talk to you about the new construction project that you have ongoing right now. I want to walk through that and then we'll get to some of your other deals as well. So, I know a very high level you guys are purchasing or have purchased a property in Raleigh, North Carolina.

You guys are knocking it down and planned. To build a single family house for sale. Can you walk the listeners through the numbers on that deal, purchase price, reno? After repair value, and then what what's that gonna look like? Bed, bath, count? What kind of fixtures you guys doing? Just to get a sense of what that new construction looks

Jen: Loaded question. All right. So the, this deal just kind of popped up again on the MLS. We, I was not wanting to do any more single family homes, but this one just came around. I was like, Oh, it is four minutes from our house. convenient. And so we just went for it. We, and the numbers made sense at full price and right there alone.

Cause a lot of, investors go in and think they have to low ball everything. This one made sense at full price. So I think the purchase price was 3 85. We're doing a teardown rebuild. It was a. Uh, horrible conditions. There was a very funky addition that, was added. And in the master bath, there was a hot tub, like literally a hot tub in the master bath.

Classy. So this area is very up and coming. And it's in between a historic area and a, um, a college actually. So there's a lot of multi, well, million dollar homes. You know, one to 1. 5 million homes. So for us, we are, a lot of them are larger. This lot just doesn't allow for a very large footprint. So we're kind of keeping the same, but going up and a little further back.

And we are going to do a 3, 500 square foot home. we have our build price at about 600, 000. So purchase price of three 80 something, three 80, 85, something like that. Build of 600, 000. Um, and that's going to be with high end, everything, four bedroom. We already have the design done. It's not going to be like the McMansions that are throughout the neighborhood.

So it's still going to be, Attractive, I think to more buyers and our ARV is one point between 1. 2 and 1. 3 so in a year when it's going to be ready, I think it's going to be even higher than that. So very good numbers again. Another reason why I was like, fine, I'll do another single family home.

We we accidentally did a teardown rebuild. We bought this one property And it kind of went back a little bit. going how I said, 25 percent of our deals come in from people who just know me. We did a, we had the opportunity to be on a bus tour, one of our projects, and it was in Durham, North Carolina.

And we did what's called pop the top where you remove the roof at a second floor. And we went out, out back a little bit. And it was a great teaching tool. So they, a busload of people came by, we did a whole presentation on everything. And from there, a Um, wholesaler said, Oh, I found this one property be perfect for your pop the top.

It was the last like small one story home in this entire neighborhood. Everything has already been rebuilt. And so we jumped on it. Our engineer went out and they're like, Oh Jen. The foundation is garbage. There's no way you're going to be able to pop the top. So that ended up being our first teardown rebuild.

And I gotta tell you, it was amazing. It's not like renovating regular houses where you tear down a wall and you're like, Oh, now we've got to replace all of this. And so there's no surprises. We know what our numbers are going to be. And it's just a lot more, predictable of our profits that are going to come from it.

Brendan: yeah, I love that. I think, you know, I've heard people say they're not making any more land. They're not, but you can take a house and knock it down. And now you got a lot to build on. So it sounds like you guys have found some success doing that, which is cool.

Jen: Yes, definitely.

David: I, I gotta say the, uh, the hillbilly or the, uh, excuse me, the hot tub in the, the master bath is very hillbilly chic.

I grew up in Lorain County, Ohio, so I kind of dig it. You know, that's, that's kind of like a, Hey, that's, that's like, luxury living. That's luxury living in my neck of the woods, but, uh, no, that, that's awesome. Are you guys planning to go more toward the by existing asset, tear it down, go ground up new build from there?

Or is it just a matter of, Hey, if the deal comes in and that's what it calls for, you take it on now.

Jen: So one thing that I'm really proud about our business is we are very diversified. We have short term rentals. We have long term rentals. We have multifamily. We do fix and flips. We have an agency that brings in some money. We started this construction company now. we're very diversified. I know friends that When short term rentals were just going crazy, they stopped everything else, put all their eggs in one basket, COVID hit, and they were shut down.

They lost thousands and thousands of dollars. So I am really proud that we are diversified, but our focus right now to answer your question, David, is we are looking for multifamily. We want to get more into the passive income of things. But if a great deal comes across our desk, we're jumping on it. So, yeah, but I get right now focused on that passive income.

We love the mailbox money coming in. Gettin old. I just turned 50. Goodness gracious. So, you know, I'm sick of my nails 

Brendan: of the mailbox money, Jen, you talked about a tiny cabin that you guys own that has become quite the cash cow for you guys. Walk us through that. So where is this located? what are the typical people that rent it from you guys? Give us the rundown.

Jen: So we have Acorn Acre. Our logo, the icon that we use is an acorn because we are in the city of Oaks. That's what Raleigh is. So all of our short term rentals are acorn themed. So we have Acorn Acre. It's just outside of Boone, North Carolina, which is three hours from us. And it's 486 square feet. It's on the side of a mountain.

So there's no foundation. And it was really tough to finance. I'll tell you that we really struggled, um, getting it refinanced. Anyone who's out there listening, looking at these tiny homes, most banks won't finance things under 750, 000. I'm sorry, 750 square feet. So 486. Square feet was tough. Also, it's not on a legit foundation.

It's literally on, pillars, I guess, on the side of a mountain. It looks kind of like a treehouse a little bit. But this thing is a cash cow. And one of the most requested amenities is for pets. And so we are dog friendly. We don't allow children, but we will allow dogs. So kids are messy. I'll tell you that.

So it's, it's a couple's. Tiny home cabin retreat and it's got a little switchbacks down to a creek and it's just heavenly. So for us to refinance it we had our small local bank and they said can you get some other short term rentals and we'll do a portfolio loan. So that's how we fixed that issue and we put it together with two other long term rentals and so we have three properties in one loan and a portfolio loan and it's the cabin that every single time like Makes three times as much as the other ones, and it's half the size, a quarter of the size.

So, um, we are 

David: Is, is Boone where, um, Is that where Appalachian State is?

Jen: Appalachian state. Appalachian state. I know. My brother, my brother, 

my, Vance graduated from there, so he's always, it's not Appalachia. Appalachian. So, I know. I have to hear it all the time. I'm like, why is it the Appalachian Trail then? So, but he has no, he has no, reason for that.

So, but yes, that's where it is. That's the pot school. So yes, we do get those people staying in our cabin. You're talking about our guests. There are guests are, you know, dog friendly. They are thrilled. They're just like us. We love to travel with our dogs. And so that's what we have recreated. And we had a door trim that was scratched up from an insecure dog, which was replaced quick and easy.

Um, we had a couple scratches on our leather sofa, but beyond that, you know, and, and dog owners are also like, my dog scratched your sofa. What do we owe you? Like, they're really, you know, whereas if it's someone with toddlers running around, they're like, whatever I'm on vacation. So. But yes, um, so short term rentals is it's a cash cow.

We absolutely love it. We're actively looking. This is what I was saying before. We're actively looking for a lake house now, and we, we just want to recreate that short term rentals in general have been slowing down quite a bit. It's a lot of factors to it. People are like, The market's saturated. I hate hearing that.

Yes. Some areas do get saturated. Orlando's ridiculous right now, but Orlando, you can still make a ton of money on short term rentals, but yours has to really stand out. That's really been, uh, the key for us is we are more of a destination. Um, short term rental as opposed to being a convenience one where it's close to an airport or close to a venue of some sort or college or whatever it is where people go because they're visiting somewhere.

This is people go there to stay there and enjoy the whole thing. So that's been our focus right now is, is to get another one and recreate that and have another cash cow coming in.

Brendan: Yeah, we've started to hear that from some of our short term rental investors where the kind of, urban type rental that's somewhat located close to things but not really, which is a convenient Airbnb to throw up, those aren't really performing as well. The ones that are destinations, they're near a body of water, they're near some sort of natural landscape, a mountain, a hiking trail, whatever it is, those are the ones that have kind of like survived the test of time.

Those are the places where people continue to frequent. And the money will continue to spit off of that rental for you. Jen, are there opportunities right around that cabin that you guys have in Boone to kind of replicate the same thing, or is this kind of a one of a kind property where it's located?

Jen: So that one is a one of a kind, but we are actively looking in areas around there just to. We love our cleaner up there to be perfectly honest. So if we can find something else nearby on a body of water, we'd love to keep our cleaners because they are fantastic. That's a huge part of the short term rental game is making sure you have a good team that's monitoring the property for you.

David: How much of your time are you spending managing the Airbnbs? Because you're in the hospitality business at that point, right? So it's, there's work involved.

Jen: So I would say You know, I get a notification in the morning, so and so's checking in today. And I literally am laying in bed, and I will say, Safe travels today. And that's all I do. When people book it, I try to respond within an hour. Now, to get around some of these, I forget what the term is, uh, what boosts your posts and stuff like that is that if you have a turnaround time, a response rate of an hour it will boost your listing.

So a trick to that is to do automation. So as soon as they book it, there's an automation that goes to them that says, here's the address of the property. Here's your unique four digit. code for the keyless entry. And so they get that immediately, but then I can follow up and say, thank you for choosing Acorn Acre just to kind of keep the conversation going.

but as you know, I have a cleaner there that's going to do things. We have a handyman nearby. And even if it's like replacing a light bulb, I pay him 50 bucks. And he's like, Jen, why are you paying me for? I'm like, because I'm three hours away and your time is so valuable to me. So overpay if you have to be really treat your team well, which is huge.

Brendan: That's a huge tip. so Jen, segment that we want to do, it's a little bit newer, so we're going to call it the unscripted Deal Deep Dive. So, tell us about a time that a project went a little bit off the script, you might have had to change your exit strategy, your partnerships, whatever it was that kind of threw you a little bit off course, and then, hmm,

Jen: Cause all projects always stay perfectly on course. I mean,

this is going to be hard to pick just one. I'm just kidding. So we recently. I bought a quad in downtown Raleigh, a historic home in a historic neighborhood, mistake number one, and it was beautiful, beautiful home, but again, the historic overlay, there was all these restrictions on what you can or can't do to the exterior of the property, so there is one We also, I thought for sure, this one is going to be so high.

It's half a mile to the bars this way, half a mile to the bars this way. We have six universities in Raleigh. It's just, how could we go wrong with this? So it was an 850, 000 purchase price and we did about 125. There was window units before. So we put in. Uh, central air and heat and all new kitchens, everything.

There was one beautiful historic bathtub that we were able to refinish and keep that. But there's a lot of charm to this property today. I've really put a lot of money into, decorating it nicely. The first thing we did... So if you are buying a property that you want to short term rent, I will not buy anything now.

Hear me anything until I know it's going to make money. As a long term rental. If that number doesn't work, then you've got to walk away. It's very volatile right now. Everything, especially in short term rentals right now. So my, another mistake that I made. Because they're short term rentals in Raleigh. We had issues for a while where they wanted to outlawed it blah blah blah, but you do have to Register it with the county and get a permit to have it.

So we bought it closed on it We're already doing some fixing it up. We start, you know, pulling the permit Turns out multifamily you can't short term All four units. So we had to pivot. I know I was like, I read everything I could find except the damn permit. So, um, it was the rule is if you have multifamily, you can either do 25 percent or two units, whatever is greater and have them short term rented.

So we shifted quickly and did it. two short term and two midterm, which are 30 days or more. And in Raleigh, we have over 60 people. It's like it goes between 60, 63 people a day moving to Raleigh. So there's a huge need for housing and people want to come and do the midterm rentals. For a little while get to know the area to find out where exactly they want to buy so there's a huge demand So we were we were still good at this point going back to David you were talking about management I think that was you David who brought that up how much time because it comes becomes a job So this I was like I'm going to pass this off to somebody else I'm gonna let people manage all five of our short term rentals at this point Huge mistake.

I don't want to name the company, but they charge 10%. They are cheap and that's exactly what you pay for. And it got to a point we, we ended up, I remember when we listed our cabin on Airbnb and literally within five minutes was like, ding, you have a, reservation. I'm like, Oh my gosh. So we put the quad up, we put a lot of heart and soul into it.

And, uh, Nothing crickets. So this company listed it for us. We had professional photos done. Um, it was just priced too high. That's I mean, just if it's too high, you've got to lower prices. I could not get in touch with anyone to lower the prices. It was out of my control. I couldn't control it. It was a horrible such literally a month went by and we're paying like five grand a month in interest for to our A different lender at that point.

And I was like, we just, we were losing money with this company. So I ended up breaking up with them, put it on my own, dropped the prices, started getting bookings immediately. Well, it was a shock. There was a very, like, there's a huge lull at the start of this year, at the start of 2023, January, February, March.

Just slow across the board for short term rentals and I was freaking out. So at that point I said and oh In this process we were trying to refinance it into our own business name So many lenders like oh, I don't know because you know You don't have the the proof because we had that one month with the other person manage other company managing it with zero bookings.

So it looked horrible. It was really tough and so many things were going against us. So we ended up selling it. And that's how totally, I mean, that's the great thing about real estate is if it's going south, you can get it off your book. So we ended up selling it for 1. 2, which was nice. We did make some good, some decent cash on it.

not a ton, but, and then of course, once we have it listed, we get a ton of bookings coming in. It started picking up April and, uh, we sold it probably at the, in mid June. We sold it as a short term rental, fully supplied everything and handed it off to somebody else who had, uh, more money to put down.

Just it was a straight cash purchase for them, so.

David: Oh, 

Brendan: wow. 

David: Like a Bob Ross happy mistake, huh?

Jen: Exactly. Oh, I'm just going to put a little tree here. Yes.

Brendan: Jen, I think the advice that you gave so many people, you should rewind and go listen to it again. Do not buy the property if it doesn't make sense as a long term I'm seeing so many investors in the Cleveland market Just that's where David and I are located where midterm rentals are very popular here we have a really strong travel nurse base a really strong traveling professional base and the duplexes that are very Very often on the market here in Cleveland people like man, I can't make it work as a long term rental But it'll definitely cash flow if I make both of them midterms.

It's like That works until it doesn't, and then what happens, right? So you're, you got a 3, 000 mortgage payment, your long term rent's only bringing in 25, 000. Who's supporting that 500, 000 Delta in addition to maintenance, CapEx, all the other additional expenses? So I think that's, that's really important, especially for an Airbnb.

I see a lot of investors making a similar type decision on midterm as well. So, luckily for you guys, you guys are able to spin out of that and make a pretty nice little profit, which is, which is awesome 

David: to hear.

Jen: And I mean, you gotta pivot. That's the whole thing with real estate. And just, you know, and I feel for the people that, Only do short term rentals and, you know, or only do fix and flips or whatever it is. And, you know, like fix and flips during COVID, you couldn't get windows. It took us five months to get windows for a property.

It was, and so we couldn't pass our framing inspection without the windows there. So it literally sat for five months. You know, so again, our cabin was holding us over for that at that point. So that's why you want to definitely be diversified.

David: Good advice. We love it. That's why we chat with people like you. You offer great advice.

So we are curious what we can expect from Jen, Josie, and Vance, since you guys are in partnership. What's up and coming for you guys? What can we expect out of you in the coming years with your multiple different business lines?

Jen: So we had a very lofty goal at the beginning of this year to have 101 doors. We're at 15. So we're, uh, we're at, uh, uh, we're at 19 and we sold off four doors, but, um, Things had to pivot throughout the, this is, that's going to be the, the theme of this podcast is the pivoting podcast, but for us, we hired a CFO to really go through our books, go through our numbers.

Again, Vance is an accountant, but he speaks accountant. I don't speak accountant. So this is more like a translator for us. And she came in and. We really looked through our books and we decided we really need to go back. Our cash cow is coming from short term rentals right now. Destination short term rentals.

So that's what we are putting our focus on. But in the scheme of things, a couple of years down the road, we definitely want to have multifamily properties, smaller units. Uh, I'm not into doing the hundred, you know, plus doors and multimillion dollars. The, just to keep it more mom and pop, more control over it and, uh, cheaper than buy those.

So, um, it's more in our price point for right now. So that's where we see ourselves headed is more mailbox money coming our way.

Brendan: Love to hear it. Jen, thank you so much for joining us today. You shared a lot of really good information. I think showed a very transparent side of real estate that I think is not as common when you have someone on a podcast sharing. Hey, here are my goals. This is what we did. We had to pivot. We had to make some adjustments, but we're still coming out on the other side, uh, you know, healthy and wealthy and moving on.

So, um, thanks again for joining us. And, uh, David and I are going to go ahead and sign us off here. 

Jen: Well, thank you for having me. This has been a pleasure.

Brendan: to this week's episode. Make sure to let us know what you think or write in suggestions or topics for the show at podcasts at upright. us. 

David: And make sure to like and subscribe to Real Estate Investing Unscripted so you don't miss out on any episodes and leave us a five star review. Jen, you were a blast, thanks.

Start Transforming Your Investment Property Now

Apply Now

Looking for an alternative to stocks?

Investing in pre-vetted, real estate-secured loans has generated historical annual returns of 10.8% for Fund That Flip investors. We provide industry-leading visibility into each project and borrower, enabling you to be highly selective and diverse in the loans you choose to fund.

Sign Up

Listen to our podcasts.

Real Estate Investing Unscripted
Investor Insights Podcast