How Real Estate Investors Must Pivot in This Market | Jen Josey on Short-Term Rentals & Surviving Slow Sales

Jen Josey (00:00)
Analyzing properties when they’re getting ready to purchase, they’re not using the right numbers. They’re getting emotional about it. It is literally just numbers. If the numbers don’t make sense, move on to the next one. There’s definitely ways to do creative financing where you can go in and make a deal work a little better.

Michelle Kesil (01:47)
Hey, everybody. Welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil. Today I’m joined by someone I’m looking forward to chatting with. Jen Josey, who is a short term rental investor as well as a coach for investors. So excited to have you here today,

Jen Josey (02:06)
Well, thanks for having me, Michelle. It’s a pleasure to meet you. As a podcaster, I rarely go on other people’s podcasts. I rarely listen to other podcasts, but I was listening to a bunch of Mike’s episodes and just really enjoying what you all are doing.

Michelle Kesil (02:19)
Amazing. Excited to have you here. So let’s dive in. First off, for those who are not yet familiar with you and your work, can you share what your main focus is?

Jen Josey (02:29)
So right now, mean, it’s because of way the economy is, you’ve got to learn to shift your focus and… ⁓

We are putting our focus right now on short-term rentals. We have, we just recently did a new build, a high ⁓ luxury new build, and it’s been sitting on the market just because economy is kind of tanking a little bit. And so it was a learning experience. We have our lenders who are being very understanding with us, and that’s part of the game is really keeping open communication with them. So our focus right now is on short-term rentals. We’re down to just two, but we are really,

making them ⁓ great experiences for the guests. We have one on the beach and one in the mountains and just learning to make sure that we provide experiences for our guests that will last a lifetime full of memories. So that’s just been our focus.

Michelle Kesil (03:24)
Awesome and which markets do you operate in?

Jen Josey (03:27)
I’m ⁓ in Raleigh, North Carolina, so ours is on the east coast of North Carolina and then also on the west coast.

Michelle Kesil (03:36)
Great. And so what do you feel have been some of the main keys that have allowed your business to be able to grow and run successfully?

Jen Josey (03:44)
I think attention to detail. I have stayed in so many short-term rentals where…

They just, they think you can just throw some white sheets and white towels in a neighborhood ⁓ property and just think it’s going to be successful. But there are so many other steps that you need to do, whether our, like our cabin, for example, is very dog friendly. So we roll out the red carpets for our pets and we call them VIPs, very important pups. And we make sure that they have a dog bed, dog bowls. We do welcome notes that include the dog’s name. So a lot of attention to detail.

The beach condo, when you are in a large ⁓ property where there’s an HOA, you have to really stand out in the crowd. You can’t just think, ⁓ it’s the beach and people are gonna wanna stay there. You have to really ⁓ work on the amenities and just making sure that you are keeping that communication open. Like right now, for example, we have construction going on in the building next door. So I’m making sure all the guests know that we are not… ⁓

that they are definitely gonna hear construction noise and they’re very, ⁓ they really appreciate us reaching out and doing that and then we’ll give them maybe some money to go to the aquarium if it’s noisy during the day, which is just down the road. So things like that, which really can take a really bad experience and turn it into a really rewarding and memorable experience.

Michelle Kesil (05:11)
Yeah, absolutely. And why is short term rentals the way that you prefer to focus on your investments?

Jen Josey (06:06)
It’s making the most money right now, to be perfectly honest. We have long-term rentals and that’s just good cash flow coming in, great tenants, but it’s really the short-term rentals that have just elevated that income coming in.

Michelle Kesil (06:22)
Yeah, and what do you think it is about the short-term rentals that makes him more profitable?

Jen Josey (06:26)
You have more turnover in between. You can just have a lot more people stay there throughout the week, throughout the month, as opposed to just having one person paying one thing monthly.

Michelle Kesil (06:38)
Right. Yeah. And so is that the asset class that you’ve originally started with or yeah, how did you get to this point?

Jen Josey (06:45)
⁓ no.

No, we started in 2017. were doing fix and flips. We joined Fortune Builders, an education program. And actually I just recorded my 300th episode of my podcast, which is the RAIN podcast, which stands for Real Estate Investor Growth Network. And I got to interview Thanh Merrill, who is the founder of, one of the founders of Fortune Builders. So we did Fortune Builders, it’s very expensive coaching program, paid over 30,000 for it, but we never looked back.

of those where you learn as you do type programs. so we start with fix and flips, and then we accidentally got into flipping condos in town homes, which kept our contractors happy in between the big major renovations, kept them busy, which also when I needed them in a pinch, they would show up. So that was great. Then we kind of fell into this cabin that we still have, which is a little cash cow. It’s a tiny cabin, 486 square feet, just outside of Boone, North Carolina.

And it has been such a rewarding experience with that one. We then ventured into our long-term rentals. I told my husband I always wanted to sleep with a GC thinking he’d say which one, but he ended up getting his GC license. So we opened a ⁓ construction company. And then we also have a brokerage as well, which is just an investor-friendly brokerage. ⁓ then we got into ⁓ multi-family. So we owned a…

Michelle Kesil (08:00)
Ha ha!

Jen Josey (08:14)
12 unit in southern Virginia, which was a horrible experience to be honest. We had, we did not put the right people in the right seats on the bus ⁓ running that thing. So it really ran it to the ground. But we were able to get out, kind of break even a little bit on that property and it did cashflow while we did have it, but it was definitely a huge learning experience. And then we, during our fix and flip time, we would do pop the top where you take off the roof and add

second floor and it was part of this whole presentation with our local RIA and at one point I had investors sending me properties and I got sent this one he’s like it’d be great pop the top for you we get there we buy it and the ⁓ the our

structural engineer said, Jen, sorry, this is not going to sustain a second floor. So we ended up having to tear down and rebuild. So that was our first stint in new builds, which love new builds. There’s no surprises. You don’t take out a wall and go, what is all that back there? But it was great. And then we thought we’re going to be sailing on this new build ship for a while. And that’s when ⁓ we have this luxury ⁓ new build that we’ve done. And like I said, it’s been sitting a while. ⁓

everything in the economy. There’s a lot of properties in Raleigh, North Carolina where I’m located that are just kind of sitting right now. So in real estate, it’s the way it is, you have to learn to pivot. So now we’re focused on doing either some more long-term rentals, but I like the short-term rentals because we need the cashflow.

Michelle Kesil (09:45)
Yeah, amazing. What an exciting journey.

And so is the short-term rentals and the coaching business what you’re most focused on right now.

Jen Josey (10:29)
So I have just, ⁓ I’ve always spoken at events and done, I’m a former school teacher. So I taught middle school music for 16 years until I woke up one day, realized I hated children. So then I went to an equally abusive industry. I went to health insurance because everybody loves health insurance, but I’m glad I had that corporate America experience.

I really was missing wearing that teacher hat when I got into real estate and real estate is a very lonely game. So when I was able to get on stage and talk about one of our past projects, it just lit a fire in me again. And I just love doing it, but I was also new in real estate. So I’m like, I don’t know enough to be a coach at that point. So I created a mastermind and it’s really just a selfish ⁓ stint for myself here because I’m just surrounding myself with people.

want to be around who, you cause you’ve missed that water cooler talk from jobs and things like that. So I created that and then that evolved into my podcast, which then evolved into more speaking gigs and being on stages. do a,

not a retreat, but more of a travel experience. So this past year, we went to Iceland, no speakers, no nothing. It’s just literally traveling with other real estate investors and exploring the earth. And next year we’re going to Greece. So we have events like that. But about three or four years into real estate, I had someone who really believed in me and he said, Hey, there’s this guy Torek something. I’m like, do you mean Tarek El Moussa? He’s like, yeah.

That’s him.

He needs coaches for his coaching program. Like what? And Tariq Al Moussa is one of the reasons why I got into real estate by watching Flipper Flop. And so I was within three or four years in this new business, I’m sharing the stage, national stages across the country with Tariq Al Moussa, meeting these amazing people. And it has just been such a wild ride. So I really enjoy that. ⁓ And just, I’m looking forward to expanding more on the, on the speaking gig as well, venturing more to just entrepreneurs and

a little bit further from real estate. that’s been one of my focuses at the moment. Yes.

Michelle Kesil (12:42)
Amazing. That’s so exciting. What have been some challenges that you’ve experienced and overcome in your real estate career?

Jen Josey (12:52)
So challenges have been. ⁓

So because we are more on the, my husband and I were more on the solopreneur track, we wear all the hats and that can get really tough. And we have discovered that we need to start putting better people in the seats on the bus and running, driving this business for us. And that is going to be one of as.

for a challenge, are going to start looking to have either project managers, we’re not gonna do…

project managers for the short-term rentals, because that’s just, you’re throwing your money away if you’re doing that. But for projects, for our next project, that’s definitely, we’re have to have someone there. My husband doesn’t need to be riding, driving to Home Depot at seven o’clock in the morning before we got to start our day to go pick up lumber for the job. So that has just been one thing. So it really slowed down the whole process, which then we’re paying monthly interest payments to our hard money lenders. So it did not work.

paid an interest, we could have paid someone to do it and got it done much quicker. So that has been one of the challenges that we have definitely figured out and need to work on absolutely.

Michelle Kesil (14:01)
Yeah, definitely. And what advice would you give to someone that’s earlier on in their investing journey or just starting out?

Jen Josey (14:51)
Join an education program. I can’t stress it enough. And make sure it’s one where you vibe with the people. There are so many gurus out there and I coach for one right now. It’s called Rental Property Pro. It’s run by John Blackburn who is a friend of mine. I don’t wanna run my own coaching program. So I’m happy to just take calls and you send me whoever you want me to coach. I love it. I only coach Monday through Wednesday and it makes me better at what I do by coaching.

That’s one of the best forms of learning is through teaching. And so I cannot stress it enough. You can absolutely get free education doing YouTube and doing ⁓ just reading blogs or whatever it is, listening to podcasts, just like this one where.

you absolutely can do it. But when you have someone, when you have an actual coach who is guiding you through and holding your hand, you’re not going to make the mistakes that many of us did. So we are going to help you to avoid making those very costly mistakes. So it’s not throwing your money away. It is investing in you. I paid almost over $30,000 for my coaching program, but I also made that back within six months. I would have not been able to do that if I was just watching things on YouTube. so I think it is absolutely important and beyond.

getting a coaching program is taking massive action. And you can study and study and study and think, you know, I’m gonna do it when I’m good enough for it, when I’m ready for it. Done is better than perfect. So I just, that’s my advice for those starting out is get out there and start doing it and have a coach who is guiding you along the way.

Michelle Kesil (16:29)
Definitely. And you mentioned that there’s mistakes people often make. What do you think those common mistakes are?

Jen Josey (16:36)
⁓ I think…

Analyzing properties when they’re getting ready to purchase, they’re not using the right numbers. They’re getting emotional about it. It is literally just numbers. If the numbers don’t make sense, move on to the next one. There’s definitely ways to do creative financing where you can go in and make a deal work a little better.

But in those situations, I think the biggest mistake is people are not buying correctly. are thinking, it’s going to be this, it’s going to be that. And they’re projecting ahead where you have to be super conservative, especially in this time. ⁓

with your numbers. I think that’s probably the largest mistake going on right now.

Michelle Kesil (17:10)
Yeah, absolutely. And what do you see as like some of the exciting opportunities for real estate in how things are changing now?

Jen Josey (17:19)
⁓ I think rentals are where it’s at right now. I really truly do. There are areas in the Midwest. Memphis is a, you know, hotspot right now, but you know, there’s other areas like Little Rock, Arkansas, Indianapolis, Indiana, other hotspots like that where Akron, Ohio is another one where you can still buy very cheap, put a little bit into it and then force appreciation of the property. And that way you’re not having to sell it and hope that the right buyer comes along. You’re just getting to that appraisal.

and then refinancing it, getting rid of your lenders in the beginning and refinancing it into your business. So I think it’s a little bit more structured and you can really have a little bit more control over it as opposed to flipping a house and hoping the right buyer’s gonna come along. It’s been rough the last couple of years trying to sell properties. So that way, just getting to an appraisal, I can handle that. It’s all about rentals right now for me, yes.

Michelle Kesil (18:18)
Yeah, awesome. And so when you’re coaching, this like you mentioned that you’re working for someone else? Do you have your own programs as well?

Jen Josey (18:29)
So I have RAIN Mastermind, which is the Real Estate Investor Growth Network Mastermind. And we do offer one-on-one strategy sessions, but it is absolutely not a coaching program. But if you are part of my mastermind and you just need ⁓ someone who get a second set of eyeballs on a deal, or if you have a really tricky situation with a tenant or something, we have a group of ⁓ former coaches that actually came from the Tariq Al Moussa’s coaching program, which shut down ⁓ two years ago. So they came over with me and

you can just schedule a one-on-one ⁓ strategy session with them to get more insight to it. But again, not a coaching program, but definitely there an opportunity to get someone who you know, like, and trust to help give you better advice on a deal.

Michelle Kesil (19:14)
Awesome. So you said your mastermind is not a coaching program, so what does it entail?

Jen Josey (19:18)
We do, we have guest speakers come in once a month. We call it reignite, which is rain night. If you, if you break it out and we have guests.

do infinite banking we had, we’re having next month. We just had Kenny Bedwell who does really high end short term rentals. ⁓ We’ve had great, great speakers come in and then we also do a mid month mastermind which is not recorded where we just discuss ⁓ mastermind topics. So like tonight for example, we are doing our mid month mastermind, we’re talking finances. Where are our finances going? What are we doing with them? How are we managing them? And it’s more of sharing because the

smartest person in the room is never as smart as all the people in the room. So we really take that collective intelligence to help each other through, you know, situations and help grow our businesses.

And we also have a Facebook group where if you need questions answered, someone will jump on there and answer your question really quick. have, you know, documents, a whole library of things that you can get to and, you know, replays of the reignites and things like that. It’s very affordable. It’s only $29 a month. It’s, it’s not a moneymaker. It’s more of a quality over quantity of folks in there. Cause we want people who are really going to bring something to the table. And it’s just, it’s just a great group of people all across the country and it’s virtual.

Yeah, so I love it. I’m selfish. I’m one of those where I’m like, I wanna be around certain people. So I created it really for myself just to learn from friends also in this industry.

Michelle Kesil (20:50)
Yeah, amazing. Sounds like an awesome community for people to get into.

Jen Josey (20:53)
Thank you.

Michelle Kesil (20:54)
Yeah, of course. So before we begin to wrap up here, if someone wants to reach out, connect and learn more about everything you’re up to, where can people find you and connect with you?

Jen Josey (21:07)
The easiest way is to go to @TheRealJenJosey calm which is Jen with 1 N and Josey is J O S E Y, TheRealJenJosey.com or if they’re interested in learning more about the mastermind they can go to reignmastermind.com that’s re R E I G N-mastermind.com. I would love to get some more subscribers on my youtube channel Which is also under the same name and listen and check out my podcast as well. There’s links in there for for other things as well, but

I’m very late to the video portion of podcasting. I’m only about a year and a half in, so I’m trying to grow my YouTube channel. So please go and just subscribe to my YouTube channel would be amazing.

Michelle Kesil (21:49)
Amazing, what is your YouTube channel name?

Jen Josey (21:51)
It is @TheRealJenJosey, ⁓ is @TheRealJenJosey, yes. Or if you’re just listening to podcasts and you find my podcast, you can just go to the YouTube link.

Michelle Kesil (21:57)
Perfect.

Perfect. Well, appreciate your time and your story. Thank you for being here.

Jen Josey (22:05)
Michelle, thank you so very much for having me on the show. It was a pleasure meeting you and thank you so much for your time today as well.

Michelle Kesil (22:11)
Of course. And for the listeners tuning in, if you got value, make sure you have subscribed. We’ve got more conversations with operators like Jen who are building real businesses and we will catch you all on our next episode.