Navigating Short-Term Rentals and Real Estate Success with Jen Josey

Title: “Navigating Short-Term Rentals and Real Estate Success with Jen Josey”

Episode: 204

In this episode of Profit First for REI Podcast, we have Jen Josey. She is a great real estate investor and helped people grow their businesses.

She talks a lot about how she was successful in buying into one of those courses that cost a lot and how she got up and running.

Let’s talk more about money mindset, short-term rentals, and translation of numbers in business. She will also share what are the things that helped her get to where she is right now. Enjoy the show!

Key Takeaways:

[01:09] Introducing Jen Josey

[03:17] How she started on her real estate investing journey

[07:19] Jen’s first property and first project

[13:40] Finding out Profit First

[17:38] Focusing on short-term rentals

[23:00] Make sure short-term rental works as a long-term rental

[28:29] Jen’s advice

[32:12] Connect with Jen Josey


[06:50] “Surrounding yourself with the right people also was a huge benefit as well.”

[22:52] “Do not buy anything unless it works as a long-term rental because, in this market, you never know if they are going to oust AirBnB.”

[29:01] “Don’t be afraid of paying for coach.”

Connect with Jen:

Website: https://www.therealjenjosey.com/ 

Tired of living deal to deal? 

If you are a real estate investor or business owner who is tired of living deal to deal and want to double your profits, head over here to book your no-obligation discovery call with me. Either myself or someone from my team will hop on a short call with you to get clear on your business goals, remove any obstacles holding you back, and map out a game plan to help you finally start keeping more of the money you work so hard to make. – David


Speaker 1 (00:00):

We were doing exactly what so many of the people that you talk about in your book. We were comparing ourselves to others in the room and scale, scale, scale. And I honestly, I really don’t want to scale and be massive. I don’t want to have 15, 20 employees. I just want to live comfortably. I wanted to be the business owner. I wanted to get start on that path to pull myself out of doing everything, having my hands in all the baskets. And so I attended your conference when you spoke in Raleigh, and it was just to that point where I needed simple CFO in my life.

Speaker 2 (00:36):

If you’re a real estate investor who’s sick and tired of living deal to deal, then welcome home, hear from everyday real estate investors just like you, and discover how they’ve completely transformed their business by taking a profit First approach. This is the profit first for REI podcast, where we believe revenue is vanity. Profit is sanity. It’s time to start making profit a habit in your business. So here’s your host, David Richter.

Speaker 3 (01:04):

Hey everyone, it is David Richter, profit First I podcast. Have a super amazing guest today, Jen Josie. She is hilarious. She calls herself an edutainer because her posts on Facebook are great, but also she goes through this episode and talks about how she was successful buying into one of those courses that cost a lot of money, and then how she actually got up and running and kind of proves some other people wrong that go through there. But then also just the mindset around money being a translator and actually knowing what the numbers mean, the clarity, just a lot of things that helped her get to where she is now focusing on the most profitable parts of her business. I’m excited because you are going to learn something and you’re going to get to know someone who is an absolutely incredible human being with Jen Josie on this podcast episode. Thank you so much for listening. Hey, it’s David Richter. I have Jen Josie right here. I’m super excited about this. She’s probably the person that makes me the laugh the most on Facebook, and she’s a great real estate investor, a great person. She helps a lot of people and mentors and coaches, and we’re going to talk about a lot of things. We’re going to talk about profit first, short-term rentals. We’re going to talk about translation of the numbers, but I’m excited to get Roland. So Jen, how are you doing today?

Speaker 1 (02:14):

I am fantastic, David. Thank you so much for having me on the show today. Well,

Speaker 3 (02:17):

Thanks for being on. I know we also are on here because you’ve worked with simple CFO and I know at the very beginning it’s like we pushed this off until, hey, we’ve actually done some things together and whatever. So I’m glad we have finally got it nailed down because I was on your podcast and you’re definitely one of the best interviewers that I’ve had. Thank you. Yeah, well give the name of your podcast real quick.

Speaker 1 (02:40):

It’s the Real Estate Investor Growth Network podcast, and it’s the acronym re R-E-I-G-N. But you have to actually type in all the words to find the podcast.

Speaker 3 (02:51):

Oh, fun stuff. I love the big names. That’s why I was like, when I first got simple CFO solutions and it’s still our email, I’m like, we bought simple CF, but it’s a nightmare to go from one to the other and I wish I would’ve had that at the beginning, but go type that in. If you’re listening to this podcast, you’ll love Jen’s too. So she’s got a great podcast. She’s a great interviewer, she’s a great person. So let’s get to know you. What started you on the real estate journey, Jen? Like what and how long have you been doing it?

Speaker 1 (03:18):

So I was a former middle school teacher for 16 years, and then I woke up one day, realized I hated children, so I am kidding.

Speaker 3 (03:26):


Speaker 1 (03:26):


Speaker 3 (03:27):

It took 16 years. Oh man.

Speaker 1 (03:29):

16 years middle school music. I actually loved it. I’m just being sarcastic, but I absolutely loved it. And I just, towards the end, I got really burned out. So


I was just decided one day I got to get out of here because I’m not doing the students well because I’m just frustrated, et cetera. So I went to equally abusive industry. I went to health insurance because everybody loves health insurance. And I did that for about six years and was quickly climbing the corporate ladder to realize I was halfway up the wrong ladder. And it was a late night infomercial, one of those gurus. And we signed up for the two hour meeting and then paid 300 for their three day course. And by the end of it I was like, take my money. And it was the best decision we ever made. It was a lot of money. I’m not knocking that, but I have made it back. We made it back within the first year. So it was just one of those things where people, they look at education programs and they think it’s just so much money, but do you want to be in the same place a year from now or do you want to go out there and start taking action? So I’m very grateful that I had that experience and will never look back. I was able to quit. I was working for Aetna. I was able to quit Aetna by the end of that year within I think it was eight months. Wow.

Speaker 3 (04:53):

Wow. What got you started so quick? Because I hear a lot of people going through the education, I’m sure just like you, and then they don’t make their money back or they never do anything. So what would you say that separated you from the people that go through that program?

Speaker 1 (05:05):

It cost about $35,000 to join. And for me, the frugal teacher, I was like, I will always have that mentality. I will not buy anything unless it’s on sale. And it freaked me out. And it was one of those things where the saying, I burned the boats. I will not go back. I saw so many people in corporate America get fired, and I was just thinking, when is it going to be my turn? And thank goodness that never happened, but I went for it. There was no turning back for me, just making that huge investment.

Speaker 3 (05:38):

You’re making that huge investment, but okay, there’s some people that do that too, but that they don’t have good success after that. What made you different, I want to know, what did you do? Did you take the action? Did you buy a house and it sucked. I want to know that first year and you’re quitting Aetna. How were you able to do that?

Speaker 1 (05:57):

Just massive action. Action. I rearranged my schedule. I would go from seven to three at Aetna, so they allowed me some flexible hours and then I would go home and from three to nine I was going through the modules and the education program. I was looking up properties, I was attending local events. I think that was a huge one for me. I met you at one of our local events here in Raleigh, North Carolina, and it was just getting that core group of people around me to help push me and to see what they’re doing and having that around me all the time and surrounding myself with those people. I think that also was a huge reason as well. People get into, they’ll pay $50,000 for an education program, but they just never take that first step. And I think surrounding yourself with the right people also was a huge benefit as well.

Speaker 3 (06:55):

What I heard was the first thing you said was rearranging the schedule. I think you put it intentionally on your calendar to do this stuff of I need to move around the work schedule. I need to be able to put the modules in and look for properties. And then you went and found other people that were doing it too and surrounding yourself with good people. So that was another big step. What was your first property? Was it a wholesale deal, a flip deal? What did you do first rental.

Speaker 1 (07:19):

So I was actually at an event with two of my coaches and they’re like, Jen, do you have your first deal yet? I was one of those where I was about six months in just who’s going to sell me a house? Who’s going to lend me money, whatever it is. And I just had that analysis paralysis and was just really afraid to take that first step. And so I remember sitting at this event and they’re like, Jen, do you have a project yet? And I said, well, I’m talking to this guy on Craigslist and it’s this property in Rocky Mount North Carolina, and there was some development and stuff going on. The railroad was moving back there, et cetera. So it’s like, why don’t you have it under contract? How much is it we’re going through? And so the guy wanted, I think about 55,000

Speaker 3 (08:09):


Speaker 1 (08:11):

They’re like 55. It was a 4,200 square foot home built in 1910. Whoa.

Speaker 3 (08:17):


Speaker 1 (08:19):

Woodwork, all this stuff. And so they said, Jen, why do you not have this under contract yet? I was like, they’re like, go call right now. So I like went out with my cell phone and as I’m walking away, they’re like, Jen, don’t forget. Everything’s negotiable. I was like, everything’s negotiable. Alright, I’m going. So I get the guy on the phone and I said, so yeah, I’d like to present an offer and by any chance is that price negotiable? And he said, sure, what’s your number? Well, I did not get that far in my thought process. I did not have a number in mind.

Speaker 3 (08:48):


Speaker 1 (08:48):

So literally I’m like, I picked my high school basketball number, which was number 44, and I’m like 44,000 said, okay. I’m like, alright, I’ll send you a contract and we’ll see you soon. And I hung up, I was like, I have it under contract and no plans. We would go out there and part of our education program is you have to use licensed and insured contractors.

Speaker 3 (09:11):


Speaker 1 (09:11):

Couldn’t get them to go to Rocky Mount North Carolina, which was about an hour and 10 minutes from Raleigh where we live.

Speaker 3 (09:16):


Speaker 1 (09:18):

It was stressing us out. So we literally just whole tailed it. We had it under, I’m sorry, we purchased it with our self-directed IRA, by the way. And we put a new thermostat on and we paid 30 bucks to the neighbor to mow the lawn. We scraped some paint and just put it back in the market. And so we sold it for 67,000 just a couple weeks later. So we got some good cashflow going and that was able to pay off some of our education and it was nonstop from there. So I am glad we had that experience. But yeah, our first major one was after that in Durham, which was a full gut job.

Speaker 3 (09:57):

That was a full gut job. Okay. Oh

Speaker 1 (09:59):


Speaker 3 (09:59):

How long ago was that? How long ago was that first deal?

Speaker 1 (10:02):

So we started our education program in 2017, April, and then it was probably October when we got that property in Rocky Mount and then the beginning of 2018 when we started our first gut job. So totally learned, and again, that network of people locally really helped us through that first project. We didn’t have a general contractor, so we found another investor who had their GC license and they gave us a very discounted rate and helped us through it. But what I loved about it was I got to make those contacts with the contractors. I did the

Speaker 3 (10:37):


Speaker 1 (10:37):

With them, I hired them, I scheduled them, I did all that. He gave me some names to go with and I still use some of those contractors to this day. So that was, yeah, it was a great way to make connections in the community and build our business from the ground up basically.

Speaker 3 (10:52):

That’s very cool. I like that a lot. Okay, so that was your first deal and then you said your bigger deal came in Durham later on. When did you make the jump where you said, I don’t need Aetna anymore? What was that decision? Was it the number of deals you had done or some profit or you’re just like, Hey, I’m all in and I’m quitting this so I can focus on the real estate. What was that thought process of jumping out of what you were doing for your job?

Speaker 1 (11:17):

So it was at the end, we made that quick money on the hotel,

Speaker 3 (11:22):


Speaker 1 (11:23):

Property, and it made sense for Vance and I that I was able to run the project full-time starting in January.

Speaker 3 (11:30):

And Vance is your husband, right?

Speaker 1 (11:32):

Vance is, yes. He’s very

Speaker 3 (11:33):

Lucky people listening. Yes, he is.

Speaker 1 (11:35):

I told him, I’m like, Vance, I’ve always wanted to sleep with a gc. And I was hoping he’d say which one, but he ended up getting his GC license. I was like, that backfired on me. But anyway.

Speaker 3 (11:45):

Well, you got your wish though.

Speaker 1 (11:47):

I did.

Speaker 3 (11:48):

Careful what you wish for.

Speaker 1 (11:50):

So it was just kind of putting our energies in the right way. Vance could support us on his salary alone at that point. So I was able to work the project a hundred percent of my time and then we started getting more and more. In fact, it was funny, I would post a lot of pictures on social media just to really build my social media presence, which has definitely helped you enjoy my posts in the morning. That right? Oh, I have. Her

Speaker 3 (12:19):

Posts are nuts. It’s great.

Speaker 1 (12:22):

And I do try to, I’m an edutainer, but through that I was posting pictures with my contractors and a friend reached out and said, Hey, a friend of mine has a condo that she can’t sell. Is that something you’d be interested in flipping? I’m like a condo. I’m like, okay, I’ll check it out. And I actually loved it. We can flip condos or townhomes five to seven days. My sweet spot is built between 1985 and 1999. They typically have already had a new HVAC unit installed. They had great cabinets back then. I can just go in and replace or paint the cabinets. We would do countertops, flooring, paint, and put on the market. And we ended up doing our sweet spot was doing about five at a time, condos and townhomes and keeping those rotating and constantly marketing to townhome and condo communities.

Speaker 3 (13:18):


Speaker 1 (13:18):

That was a great way to

Speaker 3 (13:20):

Keep it going and to stay in the real estate world. So then tell me about the journey. So you would then started building or you started doing the different process. Sounds like condos and different things like that. So then you also told me before the show started, you’ve also made some pivots. So talk about that. When did you learn about Profit first and then how we met? Just tell that story.

Speaker 1 (13:40):

So it was funny, I was sitting at a conference in, I think it was Cancun and you were coming to speak at an event in Raleigh, North Carolina. And I said, well, I should probably read this dude’s book before he gets here. And so I downloaded it and I was reading it and you talk about this guy Gary Harper, and I was literally outside the room walking in to listen to Gary Harbor speak. That’s great. And I met his wife who was what English teacher

Speaker 3 (14:09):

Was more like cafeteria. Yeah, you want a funny story? During high school we got one of those free hours and I helped with preparing lunch and she was the one there, so it was just a goof off hour basically.

Speaker 1 (14:23):

Got it, got it. So I was like, who is this guy? David Richter? And so really I dove into the book and I think it was the introduction where you’re talking about you and your wife and how you called her the ultimate spender. You were the ultimate saver. And I was like, oh, is he in the room with me? I mean, you were talking to me, David and going through the book and I have it here with me. And I was rereading it. I was like, let me just freshen up on it before I have this interview. But you were talking about the difference between being a real estate investor and being a business owner. And so up to this point, this was about a year and a half ago, we were doing exactly what so many of the people that you talk about in your book.


We were comparing ourselves to others in the room and scale, scale, scale. And I honestly, I really don’t want to scale and be massive. I don’t want to have 15, 20 employees. I just want to live comfortably. I’m a little older than you just celebrate my 50th birthday. I know that’s hard to believe, but doing the difference, I was way in that column for real estate investor and I wanted to be the business owner. I wanted to start on that path to pull myself out of doing everything, having my hands in all the baskets. And so I attended your conference when you spoke in Raleigh, and I mean it was just to that point where I needed simple CFO in my life. And the reason is Vance, he’s an accountant by trade and he speaks accountant. I do not, I just trust that he’s going to do all this.


And so it got to a point where I started coaching with Tar El Musa with his coaching program. And as a coach, I coach with him and he’s fabulous, by the way. It’s a great coaching program if you are looking to get involved and it’s a lot cheaper than these other ones. But anyway, so Vance, we ended up hiring Simple CFO, which was one of the best moves that we did. Now we are still in the process of applying profit first to our lives and to our business. But lemme back up a little. Our goal at the beginning of the year was to get a hundred doors. We started getting into multifamily and I wanted to buy out of state so I didn’t have to deal with contractors anymore. I’ve been doing this for a couple years, flipping houses, and it was ready. And again, listening to everyone around me get into this and I joined a coaching program.


I started, I had hired a coach and when we met Diana, who is our CFO through Simple CFO, she first of all became the translator between Vance and I and she is fabulous. And there are things where he’s like blah, blah, blah, blah. And he just goes through and then she’s like, oh. And then she will translate it to me exactly what’s going on. So at the beginning of 2023, we said, our goal is to get up. It was really 101 doors. A friend of mine wanted a hundred doors. I’m like, well, I’m going to get 101 doors just because I’m competitive. But going through and having her break things down and then looking at what our big money makers are with short-term rentals, and I just had to back stop from it. We bought a 12 unit joining this program. It’s not making money yet. It’s cash flowing definitely, but nothing that we could retire on by any means. And so we started that process. But then looking at the books, we have a tiny cabin in the mountains of North Carolina that was bringing in as much profit each month as the 12 unit.

Speaker 3 (18:09):

Oh wow.

Speaker 1 (18:10):

It was nuts. Now the 12 unit is not, I mean it’s not glamorous by any means. We bought it for $250,000. I offered 300. He’s like, do you want seller financing? I’m like, well, no, not at 300. He’s like, well then I’ll take two 50. I was like, dude, you went the wrong direction,

Speaker 3 (18:26):

Right? Yeah.

Speaker 1 (18:27):

So then we decided midway we need to put our focus back on short-term rentals. And people are talking about how everything’s so saturated and everybody goes to air DNA and they want to see the cities that make the most money that have 85% bookings or blah, blah, blah, blah. I don’t do any of that. And I think what has been successful for us is our short-term rental. The one this cabin I’m talking about, which is our little cash cow, it is a destination cabin. We allow dogs, we don’t allow children. It’s for a couple, it’s 486 square feet and traveling with pets is one of the most requested amenities, and we cater to it. So it’s a destination. We had four short-term rentals in downtown Raleigh. And if you went on Air DNA, oh, downtown Raleigh is the place to buy, I would’ve followed it immediately and thought, this is where we need to be. But it did not produce our cabin was, and for simple reasons, it was what they call a convenience Airbnb, a short-term run. I say Airbnb, I only work with Airbnb. I haven’t worked with VRBO or the other ones, but it’s one of those things where people traveling places, they prefer to stay in Airbnbs, but it did start getting saturated, these larger markets, et cetera. So yours really has to stand out and like I said, next month, I’m sorry, October this month we’re looking at profiting $4,000 off a 486 square foot tiny cabin

Speaker 3 (20:06):


Speaker 1 (20:06):

The mountains. So it was Diana and Simple CFO that pulled our blindfold off and was like, Jen, you are so successful at this. We need to start putting more focus on this. So I appreciate simple CFOs so much. And again, we are not in the full profit first and running it, but we have a very clear path on how to get there, which I’m truly grateful to you and your program. It’s wonderful.

Speaker 3 (20:34):

Well, I appreciate that. And it sounds like you went down the short term route, which has been great. And then I love how you said you didn’t do it the same way as everyone else does. Go to Air DNA get on there and you’re really catering to what makes sense and what makes the most money sense as well. And you’re catering to the dog or the pet owners, the people that want to have the destination. I like that. When I go on personally for Airbnb, I’m looking for destination. When I go on business, I’m looking for convenience. So it’s like I’m two different avatars on Airbnb. If I’m going with my family, I want to cool a cabin in the woods that’s very, very nice and very secluded, where the other part, I want to be in Raleigh downtown just because it’s convenient to the other things and to the events that I’ll be at. So I totally get where you’re coming from. It’s getting into the mind of the people that you’re really trying to help and have those destinations for, which is very cool. It sounds like you’ve leaned into that. Okay, so you said you want 101 doors. How long do you have to get there? Is that just I want 101 doors until I die, or in the next year? In the next 10 years, 30 years, a hundred

Speaker 1 (21:41):

Years. So it was going to be for 2023.

Speaker 3 (21:44):


Speaker 1 (21:45):

Was our focus. And I was marketing to multifamily. We drove to West Virginia by the way, I sent my avatar that I look for are mom and pop properties that someone has owned for a million years. And we go in, they’re tired of maintaining the property. They haven’t raised rents in a long time. And so I sent to mom and pops not businesses in West Virginia, and I maybe sent, I don’t know, 250 postcards and I got about 20 calls, which is I was like, what is happening in West Virginia? And I found out why. So we decided not to invest in that

Speaker 3 (22:24):


Speaker 1 (22:25):

But that was my focus. And so for 2023, our goal was by the end of 2023 to have 101 doors. And we were going strong at the beginning of the year, but it was slow starting. And then our business was suffering. And thank goodness we had Diana with her eyes on everything throughout this. We had a quad in downtown Raleigh that we were short-term renting. For anyone out there who is thinking about getting into the short-term rental business, do not buy anything unless it works as a long-term rental.


Because in this market, you never know if they’re going to oust Airbnb. There are a lot of areas, I think it’s Manhattan that just said no more short-term rentals. I’m in North Carolina. They’re talking about removing them from the outer banks. And it’s because people who live in work in those areas don’t have rentals, long-term rentals. And the landlords are like, I can make three times as much by short-term renting it. So if you are any listeners out there that are thinking about getting a short-term rentals, make sure it works as a long-term rental. So that was our mistake with this quad that we purchased in downtown Raleigh. It was this beautiful historic home and we added HVAC, it had window units before and redid everything. We brand new kitchens, brand new baths, and it just did not take off. We thought it got to a point where things were slowing down with travel and it was that convenient and people were not traveling to Raleigh as much, or it was because so many people went on Air DNA and said, oh, I want to be in Raleigh.


Because a lot of people, so another thing when you’re evaluating short-term rentals is I try to only do I just go on Airbnb and I look for other rentals in the area, I want to see what my competition is. I’m like, I could totally outdo that place and make it look so much more swankier or whatever. And then I do an average of the nightly rate, and I only do 50%. I do 15 nights, the nightly rate times 15 to figure out my baseline. And then anything above that is going to be just icing on the cake. So anyway, I went off on a tangent there.

Speaker 3 (24:37):

No, no, that was good. I mean, it’s good info. It’s good info for people to go out there and to be able to, because I was asking about the 101 doors and what timeframe that was. So it’s like you switched to what the most profitable thing was, and not just for a lack of a better term, the vanity metric of having 101, which you even said, I love that. You’re like, someone else said they wanted a hundred, I’m doing 101.

Speaker 1 (25:00):


Speaker 3 (25:01):

Oh man. It’s

Speaker 1 (25:03):

Focusing on

Speaker 3 (25:03):

A profitable thing.

Speaker 1 (25:04):

It’s still a goal. It’s just been put on the back burner until we get our finances, until we hit that profit first level where we have all of our accounts rocking and rolling, we actually have tax savings in there. We’re putting money aside for taxes, et cetera. When we get there, we will put our focus back on it. But to get there, we have found that short-term rentals is going to be our route.

Speaker 3 (25:23):

Okay, well, very cool. It’s

Speaker 1 (25:25):


Speaker 3 (25:25):

With the thing that, and that you can be profitable on and actually accelerate that profitability. No fun doing a lot of work and not seeing a lot of effort or a lot of doing a lot of effort, not seeing the results for it. So now I’m glad you got that clarity. I think clarity is that power just knowing, knowing which direction to be able to make decisions so you can do something for the future. So sounds like you got that and now you’re on your way to two a better 101 doors that’ll be more profitable, and how can we actually get there? And are you still going to go the syndication multifamily route? Is that what you’re thinking? Dumping the profits in from short term to go that route?

Speaker 1 (26:03):

So I don’t think I want to do syndication. I don’t think I want to buy the massive a hundred units. I could do that in one shot and then go through syndication and have pull a bunch of investors together. That sounds like a lot of effort to me. So I like the smaller ones. I try to be above five units so that we’re not having to deal with comps to evaluate our properties. If it’s five or more, we’re in the commercial level,

Speaker 3 (26:30):


Speaker 1 (26:30):

Then the banks are literally just evaluating your property and how it does. And I can turn a property around. I know I have the confidence to do that too, to raise the net operating income by providing a dog fee or including a whatever it is. So little things like that that I’ve learned from my coaches. So it is still on the radar. And I got to say I pivoted because Diana just revealed all of this for us in simple CFO on it. And she is fabulous, by the way. And I also know Michael Glassby. I’ve met him at a couple conferences and he’s another one of yours. And he was on my podcast. He did a renovation of a historic home that he did a condo conversion, which is pretty cool. But anyway, I digress. It’s just the goals are still out there. Long-term, having those doors, whether it be a 20 unit here, a eight unit here, it’s the long-term, five years down the road. But to get to that point, we got to focus on the short-term rentals, which is what was uncovered. Yes.

Speaker 3 (27:40):

Oh no, very cool. And I love how you said she’s the translator too. You’ve got the accountant husband who speaks accounts, and it’s like we got to be able to translate between the two, which I hear that a lot when there’s partners working together or husband and wife for it’s other financial people on the team. So I’m glad she’s also doing that for you. That can be, that’s one of the reasons why I even started this. I had people speak accountant needs to me when I was just a baby business owner. I’m like, what are you saying? What is this? What are you talking about? So I’m glad glad she’s doing that for you as well.

Speaker 1 (28:14):

Yes. Well

Speaker 3 (28:14):

Awesome. Then I just have a few last questions here. Is there any other advice you’d give to a real estate investor that’s listening to this? Anything that you’ve learned in the real estate world that you’re just like here? One last piece of advice I’d love to give.

Speaker 1 (28:29):

Be ready to pivot and don’t put all your eggs in one basket. And I’m very open to it. We’ve had to pivot quite a few times. We started with that property, that massive project, and then we started doing our full gut job. And then someone’s like, Hey, what about condos? And just be open to those things that come across your desk. And now we’re actively looking for another destination, Airbnb, a couple of them if we can.


And don’t be afraid of paying for a coach, because a lot of people get really stuck. I said this at the beginning, they get stuck on that price of what it’s going to cost, but how much is it going to cost you to not invest in yourself and to make that jump, but pivoting, I had friends who put all their eggs in the short-term rental basket and stopped flipping, and that’s all they did. And when Covid hit towns, shut them off completely and they lost thousands and thousands of dollars. I think having a portfolio that is yes, we still have our 12 unit, we have two long-term rentals as well in addition to our short-term and just being diverse in that we are doing a tear down rebuild, starting that in a couple weeks here. And it is just be diverse in how you invest in things and don’t just focus on one, be open to other things coming across your desk.

Speaker 3 (29:59):

Awesome. So there you go. Focus on what is the most profitable and what’s the thing that’s going to help you get to where you want to be open to those other areas. That’s really good advice. And then if you had to start your business over from scratch, is there anything you would do different?

Speaker 1 (30:14):

David? I would absolutely have rentals from the very, very beginning. We didn’t get started until about year two or three, and I would have some of these properties that we should have held onto would’ve been making a gazillion dollars now. So don’t be afraid of it, or I’m sorry. It’s the whole having those rentals so that you have that ink that monthly, you can kind of assume what’s going to be coming in per month and it will then help you support the rest of your business knowing that that’s coming in monthly.

Speaker 3 (30:53):

Well, there you go. So if you had to start over, you’d start off with more recurring revenue from the rentals and getting that foundation laid sooner. But now you’re on the hunt for the 101 for the get

Speaker 1 (31:04):

Down. I’m on the hunt. On the hunt.

Speaker 3 (31:06):

So if you have a destination place that you want to sell, this is where you can get ahold of Jen, Josie. Go to find her on Facebook and see all of her funny memes and stuff that she posts and then message her because she’ll message you back. But okay, this has been awesome. There’s been a lot of good stuff here where I from, even the beginning that you invested in yourself, even as a teacher that had the, I want to just the cheapest option and stuff, and you invested 35,000, you rearrange your schedule to make sure it happened. You did the modules and the education and all the real estate stuff on your time off. Then you were attending the local events, doing the networking, did that first deal, actually took action, went from there and did a lot more deals. Then got when we started working together, getting the clarity on what’s most profitable and really focusing on that. So don’t be afraid of paying for a coach. Be ready to pivot, have rentals from the beginning. Lots of great information and nuggets here. So how do people get ahold of you or what do you want to share with them? I know you have an Airbnb short term, like course two. So whatever you want to say here to give people that value.

Speaker 1 (32:10):

Wonderful. Thank you so much, David. So the best way to find me, you can go to the real jen josie.com and it’s J-O-S-E-Y. And I have had so many people reach out and say, Jen, because when we had that quad, we ended up selling the quad because it wasn’t performing. We thought it would, and many people were stressing out about, and they said, Jen, how are you so successful with short-term rentals? And so instead of having a thousand different conversations, I literally just put everything into this quick, it’s an evergreen online course. You watch videos. I have my contracts in there. It’s 99 bucks. I’m not looking to make, I just want to serve my community from people have done it for me. So I just want to give back. And you can find that it’s at rain mastermind.com/courses. So that’s R-E-I-G-N mastermind.com/courses. 99 bucks.


The best part of it, and this took me a lot longer to organize, but I made a list, a huge spreadsheet of everything that I purchase, all of my disposable shampoos that I do, my sheets, my furniture, all that stuff is in there. It’s a great reference if you are setting up a short-term rental. So check it out today. Thank you, David, for allowing me to share that. It’s just one of the, I get a little like, because I’m not a guru by any means, but it’s just one of those things like, Jen, can you help us out? And instead of me having a thousand conversations, I just put it all into this quick online course, 99 bucks just will help you get started properly. I also had to deal with bad guests and bedbugs and things like that. So we talk about all the different things that happen in there. So thank you for letting me

Speaker 3 (33:48):

Yeah, for sure. The values in the organization. So it’s like being able to go there and say, okay, what’s the first steps, or I’m having the trouble with this, or the different things for the house. So I know that, go there if you need that help. On the short-term rental side, like I endorse Jen Josie, a hundred percent. So if you go there, it was Rain, was it Rain Network mastermind.com.

Speaker 1 (34:06):

Rain mastermind, rain

Speaker 3 (34:08):


Speaker 1 (34:10):


Speaker 3 (34:10):


Speaker 1 (34:11):

Slash courses

Speaker 3 (34:12):

Slash courses. So rain mastermind.com/courses. Go there, get the course, you’ll be happy you did. If you’re in the short-term rental world, this has been awesome. And if you are like Jen and you are like, I have no idea what the focus on, or I don’t know where the clarity is and I need that clarity, or I want Profit first in my life, go to simple cfo.com, see if we’re the right fit. We can at least point you in the right direction. I just want to bring you value. If you’re out there struggling and have no hope for what’s going on, I hear all the time people for a decade or more and really have never had financial peace. So head over to simple cfo.com, schedule a call with our team. Thank you for listening. Thank you for being here. Thank you for being a part of this Profit First RAI podcast and remember to make Profit a habit in your business. And Jen, thank you for being an amazing guest.

Speaker 1 (34:59):

Thank you for having me, David. I’m a huge fan of yours and you have truly made a huge difference in my life Between Profit First for real estate investing and simple CFOs. So thank you, David.

Speaker 3 (35:12):

Aw, thank you. I didn’t even pay her to say that. This is good stuff. Thanks everyone. Have a good day.

Speaker 2 (35:18):

This episode of the Profit First for REI podcast is over, but there are plenty more where that came from. Are you ready to learn how David and his team can help implement the Profit First system in your business? Schedule a discovery call@simplecfo.com right now. We’ll see you next time on The Profit First for REI podcast with David Richter.