06/06/2025 9:48am

This “Dirtbag” Hiker Built a Boutique Hotel & Real Estate Portfolio

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He lived in an RV behind a duplex. He hiked both the Appalachian and Pacific Crest Trails. Now he runs a boutique hotel in Montana — and built a real...

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In this episode

we were living in a 55 plus retirement community your typical RV resort where

you’re like 10 ft from your neighbor my biggest idea of house hacking was live as cheaply as possible you were the best

tenants they ever had that also I think gives you a lot of good perspective on how to be a good landlord that’s what it’s all about it’s taught me how to be

a tenant but also it’s taught me how to be a better landlord in a way if I can do it you can too one step at a time

[Music] performing as well as Welcome back to the Hybrid Real Estate

Professional Podcast the show where we break down how high performers are building real estate portfolios without burning out or blowing up their lives

today I have a special guest Joe Gimenez beaming in from Callispel Montana joe’s a real estate investor hospitality

entrepreneur and full-time adventurer after hiking both the Appalachian Trail and the Pacific Crest Trail and living

in an RV full-time for over six years Joe traded in his dirt bag life to build

a small and mighty real estate portfolio in Montana alongside his wife Katie he owns a boutique hotel and a handful of

vacation rentals proving that you don’t need a hundred doors you just need a few great deals intentional design and the

guts to do things differently whether he’s backcountry skiing climbing sketchy peaks in Glacier National Park or

disappearing down gravel roads on his bike Joe brings that same spirit of freedom and exploration to his investing

strategy he’s passionate about building businesses that fund a life of freedom and helping others think way outside the

traditional 9to-5 box joe welcome to the show man great to have you love it

thanks for having me Ers adventuring I think is a theme that’s going to come up several times in this conversation and

I’m grateful to have gotten to know you in we’re both in coach Chad Carson’s community and we even got to meet I got

to meet you and Katie in person in Charlotte earlier this year and immediately one of the things I’m

stricken by talking to you is you just have this very you have a zest for life and you really are not afraid to go out there and and experience the world and I

admire that from afar especially as someone who’s got my my lifestyle is pretty constrained and contained at the

moment I applaud that and I want hear a little bit more about how you’ve been able to build a real estate portfolio

while still scratching that adventure itch i would love to hear just at the beginning you talked about living

full-time in RV and almost off-rid for what was it 6 years is that right

yeah about six and a half years i would correct that a little bit it wasn’t quite off- grid we lived originally

we’re from Florida i’m here from Montana now but um we were living in a 55 plus

retirement community which are very common in Florida so we just your typical RV resort where you’re like

maybe 10 ft from your neighbor but there’s like driveways and just to live

for really cheaply i think our lot rent started at $300 a month so just try to

keep expenses low can you explain how you were living in a 55 plus community in your 30s wheeling and dealing

Aaron no I just I think there is there is anyone interested in doing this there is a technically speaking parks are not

allowed to discriminate for age so we we didn’t realize this going in but we actually applied to stay at an RV resort

next to the one we ended up staying in it was kind of sad but they were like “We love you you guys seem like we get

like at the time we were kids good kids.” But they’re like “We’re afraid that there’s a lot of elderly guests

that live here that they might take exception to you guys living here maybe you want to go next door.” We went next

door to the RV park next door and I was ready to just give my spiel and I went there really nicely dressed and

everything like that and I was ready to just like negotiate we’ll pay 6 months up front and all that but they took us

in with open arms i didn’t even have to uh try to negotiate or con do any convincing and then yeah we ended up

when we left there they ended up saying that we were the best tenants they ever had we didn’t complain about the the

grass being cut too short or the the tables being moved in the community center incorrectly so we just paid rent

went to work and yeah they loved us so it was a great experience and it I think that was probably the biggest thing that

set us up to be able to save money for a down payment and then start building this real estate portfolio it’s

interesting you say you you were the best tenants they ever had that also I think gives you a lot of good perspective on how to be a good landlord

right because I I think we all any real estate investor that is in the game long enough what makes a good tenant and what

makes a bad tenant and it also gives you that framing to know how to be compassionate and empathetic but not too

much so to where you’re creating bad habits or ingraining the wrong idea and so I maybe that’s a little thread I’d

love to pull on is do you feel like your experience traveling renting and just experiencing life on that side of the

fence has made you better at what you do now

yeah probably yes i say it all the time to Katie because we self-manage actually we’re selling our duplex right now i’m a

short-term rental expert these days but we had a couple of long-term rentals and I say it all the time like we have a

duplex with one tenant who’s just they’re always calling me and bugging me and texting me and like for the littlest

thing and then we have one tenant who’s amazing pays on time doesn’t just doesn’t bring me problems they just

bring me solutions and I really we really we appreciate her and we love her

because she makes our life easy and I think that’s what it’s all about just we do what we say we’re going to do we pay

on time and in soul we we just basically try to be just stay out of the

landlord’s hair and it’s taught me how to be a tenant but also I think yeah it’s taught me how to be a better

landlord in a way but I will admit I’m not the best landlord it’s very that’s why I’m switching to hospitality it’s I

I prefer to have guests over tenants that’s But yeah no that’s it’s

exactly right but I asked her that too when I was like “Why were we your best tenants?” And she she said just that she’s “You guys are quiet you guys don’t

give me any problems you’re you pay on time in full and you just stay to

yourselves and you respect the space and you keep your place tidy.” So yeah it made me feel really good leaving just

going from from the beginning full circle not thinking that we were wanted anywhere and challenged to find a place

to stay and save money to being like “Wow she even told us like we could come back anytime.” And it was like no kids

allowed but she even if you guys had a kid you could come back and you could have your kid hey we have a bunch of grandparents here that would be loved to

to be babysitters and yeah it just it taught me a lot but yeah very cool so

you mentioned Sorry go ahead i was going to say thanks for not pointing that out i didn’t I never framed it that way but

yeah well we thought we were supposed to do just pay rent and just be good people it’s simpler than people think but yet

yet there’s still a lot of different types of tenants that create cause problems so it’s good not to be among

those but so let’s retrace a little bit you mentioned that you being a landlord is very different than being in a

hospitality business like you’re in now and I know you guys have will get to the current business but talk about like how

you first got into being a real estate investor i believe it was house hacking is that right that’s right yes so when

we lived in the RV park we lived in a fifth wheel so for those not familiar it’s basically your it’s like a pull

it’s like a pullbehind trailer but it’s the has the big part that goes over the truck bed and it they’re huge so it was

like 32 foot in length and it had three slide outs but uh after living in that

for six like I said six and a half years almost we sold that um and then

purchased a 21 ft motor home that we could drive so we drove this from

Florida to Montana and stopped everywhere in between and to back up a little bit if had I known about house

hacking this is a real estate podcast so we all know the term house hacking um had I known about house hacking I would

have done that early on in my career but I didn’t know it was a thing my biggest idea of house hacking was live as

cheaply as possible so live in an RV park so we bought our So fast forward I

educated myself i found Coach Carson’s podcast i was hooked so I learned about the strategy of house hacking and we

were searching for a small multif family in Montana that we knew we’d live in and we purchased a property put a big down

payment as big as we could it was already rented so both sides there was a three-bedroom one bath and a onebedroom

one bath and we actually drove to the property with our motor home and installed a 30 amp hookup and we lived

in the alley behind this duplex and rented kept both sides rented out so we we lived for free on the property it was

quite a conversation to have with the tenants at the time i’m the new landlord also I’m going to be sleeping behind the

garage here right by the dump spirit so it was part of I think it was I think it definitely was true to I don’t know we

throw the term out dirt bag out there as a hiker as a adventure and it definitely was like in line with that vibe and it

saved us a lot of money so it was awesome yes to be clear I did not come up with the idea of calling you a dirt

bag that was your own term that I read from your bio but I actually like that you have this real connection to being

outdoors and you exploring and seeing the world it’s something that I grew up

in the Pacific Northwest in Seattle area i lived in central Washington there’s just tons of natural beauty all around

and one of the things I regret is not taking better advantage i did get out quite a bit before we had kids and in my

earlier years but it’s something that in my 20s and 30s I haven’t done as much as I would like and so when you reflect

back on you’ve been able to hike the two major trails in the US i’m sure you it seems like still constantly or getting

outside and getting dirty a bit like how has that evolved over time obviously you did it full-time adventuring for a while

and now you have this kind of hybrid life where you’re running your business but you’re still out there scratching that itch can you talk about that like

evolution of what the outdoors means to you wow that’s a lot a great question i

could say a lot on that i think for me so we’re 40 minutes outside of Glacier National Park here in Callispel i think

about it all the time i think in my early 20s I I was in a place where call

it selfishness call it I’m not sure maybe it just may take like I was okay just being in the woods by myself not

having any contact with the world being off- grid and I felt like I was fine i didn’t really I was only thinking about

myself and just thinking like how fun this is and how much freedom this what I had now I’m happily married with my wife

Katie that you mentioned and it’s hard for me we manage a business together we do everything together we have breakfast

every morning she’s an upper entrepreneur as well as myself so we

every morning we just wake up we have breakfast we just talk about our day and

then we go about our day and the cool thing about Montana as well is that where I’m at there’s so many

opportunities for adventure and um like tomorrow I’m going on a 60-mi gravel ride in just in the national forest so

and I can be home in time for dinner so it’s for me I still love to do those longer trips i haven’t planned one

recently but like it’s still I can still have a taste for that and I can still enjoy because it’s hard right quitting

your job for 6 months and being in the woods and not making any money a challenge and I think it’s there’s a

time and a place i think as a young person it was exactly what I needed at the time it taught me a lot about life

in general and now just being able to operate my business and I still do that

it’s fun i almost feel like I’m cheating at life in a way like from the tech side there’s a lot of tools and tech that

you’re aware of Aaron that enable that right like before it was a lot harder like we use a property like for our

short-term rental business we use a property management software that I could just operate from my phone and

then we go on motor home trips we still have the motor home that we we lived in behind our first duplex and we I

actually just dewinterized it two days ago so Katie and I will go on church where we will actually be like in the

national forest with no service but we do have Starlink now so for example I

could still go out go for a hike disconnected completely and then Katie can manage things while I’m gone and

then in the evening we just check our messages make sure nothing happens so it’s a lot easier I will say to do it nowadays than it was 10 years ago but

also like I said I think I live in a place that I can get maximum adventure with little commitment if that makes

sense i don’t know it’s my dream place it’s not for everyone we don’t have clubs and fancy restaurants but if you

like the outdoors Montana is is the move yeah so I I love that and one of the

things I talk about a lot on the show and also just out in the world when I’m meeting different people whether they’re investors or not is building your income

streams and your businesses and and whether it’s a W2 job or a side business build it around the lifestyle that you

want to live and you guys are exact symbol of what that looks like where you

knew what you valued and what you wanted to be doing with your time you knew that you still wanted this stuff to be able to fit into your day-to-day life and so

you found a place a physical location that you like living that has access to all that stuff and you also built and

designed a business that allows you to put your guys personal touch and your love for all those things and impose it

into that business so that you can share that experience with people that are coming through and that kind of ties to what you were saying earlier where you

did the landlord thing you learned a lot you were a good tenant you were you were learning the ropes of the landlord but

then it sounds like you naturally somewhere along the way shifted towards hospitality and so what initially prompted that and

then of course like maybe take that into how you landed on this bigger project that you guys have right now

yeah so we purchased our first duplex as a investment property um I knew that we

were going to build a small portfolio that was the plan and so we did that

knowing knowingly we purchased that property we technically didn’t move in um and then we purchased our second

property about 8 months after the first one and we purchased that as a primary

residence um so we and we moved it was another duplex we it had needed a lot of

work it was accidental I would say as people might be aware short-term rentals

they command a lot more rent than the typical long-term rental it takes some more expenses up front but we realized

okay after we overpaid for this property pretty during COVID years but we knew we

had to increase our cash flow and we knew we already had a max for hospitality both my wife and I my my

wife Katie actually went to school for hospitality and she’s a wedding planner and I knew like we we were very involved

in couch surfing i don’t know if you guys are familiar with that but basically we just hosted a lot of

travelers international travelers people traveling across the country so we already loved hosting and loved just

meeting new people and specifically travelers so we knew we had the knack for it um I just we didn’t have any

experience short-term renting so we just thought okay let’s just try this thing let’s we remodeled one of the units of

the duplex on the second house and that was funny because we still had the motor home and we were living in the unit

while we were fixing it up the second unit was like trashed horrible condition and we had our RV parked on the property

and we were fixing it up and we were living in it while we were fixing it and then we prematurely listed it on Airbnb

we were pretty much ready we just had to do some deep cleaning and finally finalizing and we got our first

reservation that was pretty extreme we had to move out we had to move out and

move back into the motor home but we got a reservation for a week and the rest is history we just we I think we tasted the

increased cash flow and it was like “Wow this is pretty good.” And we live in an area that is very popular during the

summer people come here for fly fishing biking that kind of thing so I think getting a couple of strong reservations

early on made us we enjoyed the additional cash flow and income but we also were like “This is fun it’s a way

to make more money and also meet your people and meet travelers.” I don’t know it made sense sorry rambled there no not

at all actually I think few things that are important to highlight there because a lot of people consider short-term rentals because they like the idea of

more cash flow the the idea of having somewhere they can stay themselves they like all that but they don’t think about

the fact that you’re probably having to interface with people all the time if you don’t already have the composure or

character that is interested in socializing sometimes guests do want

additional touch points or they might want advice or or guidance on where should I go what should I do so your

wife Katie she studied hospitality but then you guys also got some reps of like couch surfing and just like interacting

with strangers in a fun and I don’t know welcoming way and so you knew before you

even started this business that you guys could handle that and it was something enjoyable to you and again you’re

sharing you’re sharing your love of this area and the outdoors with people the

proof of concept was twofold right it was that yes you saw the additional cash flow that came in and how that’s

probably better than landlording and also the proof of concept was your guys’ ability to handle that type of business

cuz I do think there’s a difference between getting the landlord the long-term rental 8:00 p.m like the

faucets loose phone call versus the short-term rental message of hey what’s a cool place to go eat dinner around

here or hey I appreciate the w the welcome note that you left me maybe I had a couple questions about it it’s

like a different feeling giving to people like that than it is to some of the stuff you deal with as a landlord would you agree yeah no I I would like

to comment on a little bit on that thanks for pointing that out yeah i tell people like one you have to enjoy

hospitality if you want to get into short-term rentals like it is there is a lot of benefits like you said the buil

the ability to block off your calendar if you want right if you have a lake house or something and you’re like “Oh

my family’s coming for a week we want to stay there and enjoy it.” That’s great you got to think about the opportunity cost of blocking that off right so we

tell all of our family you can’t stay with us in July or August um but also

yes it is hard and we do love people but it is challenged when you’re dealing like long-term rentals you’re dealing

with people’s homes there’s a lot of emotions behind it right like you got family you got stress and you’re dealing

with people’s day-to-day life which is not always not always positive people go through struggles and trials and stuff

so you’re dealing with that as a landlord it’s more of a I think the ten tenant landlord relationship is just

historically it’s more at odds but for short-term rentals as you pointed out people are on vacation they’re it might

be their bucket list trip for us they’re coming to Montana they’re from the East Coast or something and this is the first

time they’ve ever visited Montana so they’re already like in a good mood they’re open to just the experience and

a good time so they’re like celebrating a lot of times but I think that’s it’s conducive to a better experience now

you do still get texts annoying texts in the middle of the night sometimes but the another thing I would say about

short-term rentals is like for example as a long-term rental like if okay if

the furnace is broken and it’s winter in Montana you got to get that fixed right now emergencies obviously we fix right

away but cool thing about short-term rental like long-term rentals sometimes you can schedule those repairs but say

if it’s not an emergency but like a lot of times your short-term rental guest has to stay for 3 days and there’s one

aspect of the room that’s not right and a lot of times those are more like okay it’s harder to schedule that out or you

want to fix it now so you can like keep the guest experience at the top level so that’s just something to think about

it’s not just you can’t defer as easily sometimes as the long-term rental yeah and that’s actually about Yeah that’s

another topic I wanted to hit on is expectations so you guys you have a beautiful boutique hotel i went through

the website before this like each suite has its own name it’s thoughtful like thoughtfully designed i’ve heard you

guys talk about I know we talked about when we met in person like the level of effort you put into making people feel

welcome the personalization like trying to understand maybe the purpose of their trip so that you can even leave

individualized guidance if you know somebody’s there for a family ski trip that’s different than someone who’s

there for a bachelor party that’s different than someone who’s there for any other type of reason so you guys

take it upon yourselves to be proactive and provide a good experience but also the guest has their own expectations and

I think that’s probably one of the hardest things to manage if I had to guess is that when people come in and they’re booking something that’s

positioned as like a premium experience do you find that people it’s hard to meet people’s expectations do they come

in with unreasonable ideas of what their trip would be like or do you find that it’s pretty you guys have found a happy

medium of providing the type of service where like everyone kind of wins in the long run amazing question i think more

more short-term rental people should be asking this so I think the biggest thing

why people the biggest reason people leave like bad reviews is mismanage

expectations so we carefully avoid using terms like luxury and high-end that type

of thing because that’s subjective right your version of of luxury is going to be different than mine i sleep in tense and

on the ground and on the mud so it’s so we still have we have this like kind of underell overd deliver like style it’s

just our style and people they end up commenting on “Wow this was like a lot of times people will say we booked their

our fancy place in Whitefish or whatever and then we booked Switchback Suites because it was 10 minutes from the

airport.” And they’re like “Man I wish I would have stayed at Switchback Suites the whole time.” So yes like we’re in

downtown for example another thing we do we’re in downtown it’s actually fairly quiet we’re not on a main like highway

but we’re one street off of that or one there’s one property like there’s a buffer two properties blocking us from

the high from the main road here and I say highway and it’s a two-lane road because it’s Montana that bet but

there’s sometimes where people we make sure to put that in our listing description right we even had actually this is a good example two days ago we

had this woman who was like “Hey what’s the yard like is there a place for us to sit outside and hang out and is it

forested?” and we straight up told her like “Hey we would love to host you but basically we’re like I don’t think we’re

going to be the best fit because we’re in town we our main benefit is that we’re central you can get to almost

anywhere very fast we have high-speed Wi-Fi full kitchens all those things luxury or high thread count linens and

towels and people love that we have a digital guide book where local guides that’s what we pride ourselves in but if

you want a place where you can like sit by the creek and enjoy the beautiful serenity of the a cabin in the forest

then we’re not that i think that says a lot to a lot of people try to be

everything for everyone and I think it’s important to find your target avatar

your your perfect potential guest we like to call it so you’re not trying to because you’re not going to be a great

host for everyone right you rather just find your p your type of people and then do really well for that like maybe our

if our client was families that want quiet and peaceful time in the mountains

in the forest then we would market for that and that would be us but like we pride ourselves in we’re for the

traveler the young traveler people who want amenities like fast Wi-Fi they want to be able to walk to downtown walk to

the coffee shop my favorite series um and they just want to be central to

everything and they’re they used to they know how to use tech right right we use smart locks for everything so that kind of thing and we put that in our listing

description we put that in our copy everywhere so a lot of people don’t stay with us because we and that’s good but

their expectations they know what they’re getting and so we end up we pretty much only get five star reviews

because we’re getting a guests that are meant to stay with us and hopefully that makes sense so yeah a followup on that

then so you guys know your guests very well now you’ve owned this place for almost two years correct

just over March 31st here we are in May so yeah a little bit over two years awesome congrats on that and then so my

question is you know your customer now because you have two years of experience and data to see what do people like

about this place what draws people in what are things that don’t work but when you bought the hotel originally I know

you guys did some renovations and added suites and all that did you already have an idea of who your ideal person was or

did you let that kind of reveal itself as you started having guests good question i think we we had an idea but I

didn’t realize how important it was to literally define it like I have a it’s

on our social media literally we say perfect for work from home nomads and

adventurous couples like it’s just we point blank say it we get guests all types of guests but we just clearly

defined it and I didn’t cuz you can’t change your location i knew we were in town like we weren’t the beautiful place

on top of the hill overlooking the city the town in the forest like we knew what we had but it developed i realized like

just through learning just obsessing over short-term rental optimization and learning about that that yeah you really

have to define your guest i think another thing it’s market specific like people are already coming here

kellispell again we’re close to national park having the duplex which was the second property that we bought as a

short-term rental gave us it was like low stakes training lower stakes now that we have a 8 unit with a business

partner that we dearly respect so we’re like we can’t mess this we can’t mess this up the town home it was Katie and I

we owned it we locked in a really good COVID years interest rate of 3.5% so

it’s lower mortgage lower stakes and we were able to make more mistakes and then we just applied at to the 8 unit so

picks up a little bit and says how we backed into the 8 unit we didn’t just go from you know living in our motor home

in the alley to switch back suites right there was some step in between there yeah so I actually want to I want to

talk about that because I think you and I both bonded a bit when we met because of the idea of we started with a smaller

portfolio like you said the stakes are lower the maybe single family homes or small multif family we did the long-term

leases the self-managing landlord thing and I think for both of us respectively

it was like a really big learning experience and it allowed some of those early maybe you pay a bit of an

ignorance tax which I think is a good thing when you’re learning some of these lessons you need to learn them enough to

internalize them and then when you go on to a bigger project you hopefully don’t have to repeat some of those early

mistakes do you feel like you would be you would have been prepared for the

boutique hotel and what you’re running now the business partnership had you not had that earlier experience because I

see a lot of people trying to cut the line i just want to get your take on that absolutely not we wish that great

question no we would not have been as prepared at all and I think we have a

strategy it’s a little bit of a my friend the other day told me we went to a coffee shop and they they had cups

that said they had little questions of the day and I really enjoyed that and the first question one of the questions that I got was what’s one thing you

appreciate about your the person you’re having coffee with and the question yeah was like what’s one quality and she said

I love your ability to you in business so you really you think about things you

you have a good strategy you strategize you run the numbers you do all those things that you’re supposed to do and

Then you just you just unhingedly go in if thought man like I was like I don’t

know if I should be offended or actually what I thought about it and I was like wow that’s the nicest thing someone ever noticed about me is that there was

definitely a lot of just taking action and just trying it i’m sure Aaron you can relate to this like at the end of

the day you can only study up so much but we have the strategy with the hotel that like if we get the same we’re quick

to pivot we’re quick to correct we’re quick to learn from our guests what they what their reviews or what they tell us

we have this if people mention something maybe it’s constructive criticism or something negative three times then we

correct it right away so even our rental agreement as we like our pet policy

every single thing like that is formulated like from trial and error so

now I I feel pretty confident in saying that like our systems are pretty dialed but like from day one like it was

definitely what my friend said it’s just just full sand go for it and then make the mistakes and again like we wouldn’t

have been able to do that as easily we made some mistakes with switchback speeds nothing too crazy we’re still in business so couldn’t have been that bad

but yeah like for example I’ll give you a funny story like with the town home our very first guest Katie and I we love

house plants we we just like greenery and just making the place feel it just feels more alive and we put all real

life plans in our first short-term rental and then our first reservation the guy I think he stayed for it was a

long reservation it was like a couple of weeks or something and our first guest like he proceeded to come in meanwhile

Katie and I were living in the driveway in our motor home we moved back um to fix the second unit and he proceeded to

close all the blinds like complete zero sunlight and after he checked out we

went back in to check the space and every single one of our live house plants were ded from that experience now we’re like

“Okay it’s not as nice it’s not the same exact effect but we just put fake house plants in all of our units.” So that was

just one example we wouldn’t have known we were just naively “Oh it’s so beautiful everybody else has fake house

beds but we’re going to be smart and have real house plants to make even a nicer vibe and we’ll learn that lesson

real quick on our first guest i love it so yeah yeah no and I think you you hit

on something really important that I also it’s a common theme among the interviews I do it’s a common thing that

I reflect on in my own journey which is there is like a spectrum where very

analytical people which I consider myself to be pretty analytical it’s easy to get trapped analysis paralysis that’s

almost a cliche at this point but it’s true like everyone in their own way faces that and ultimately like the

ability to make a decision even if you don’t have 100% certainty because

nothing is 100% certain that is a superpower in and of itself so even though I’m very analytical I do pride

myself on having a bias for action as well to where I’ll try and derisk things

as much as I can by arming myself with information running numbers talking to people but at some point you literally

just have to decide am I going to do this or am I not and if you keep thinking about it for a year and you

haven’t done it then maybe the answer is you’re not going to do it and if you are going to do it then you have to just

find a way to make it happen and so I think that compliment that your friend gave you at the coffee shop is a good

one because he wasn’t saying that you’re a careless like goober that doesn’t think about anything he was just saying

that he it sounded like he he admired your ability to take action and learn from your stakes mistakes and the other

thing I would say too is that like people think of failure as a complete like there’s nothing positive that comes

out of it but one of the framings I’ve enjoyed the most is you either win or you learn it’s not win or lose or win or

fail it’s you win or you have a moment where you get to learn so the house plants is a great example that’s a

lesson it would only be a failure if you failed to take something away from it right and even the toughest moments in

life you can take something away from it that can make you stronger or more resilient in the future whether that’s

your personal life or professionally i don’t know if I don’t know if you agree but 1,000% agree yeah amazing and I

think yeah there’s a lot to be said about that but no I’ll just leave it at that i think for me I used to struggle

more deeply with toxic perfectionism um and I would like not want everything to

be perfect and if it wasn’t perfect I would just give myself anxiety or something like especially dealing with

tenants or anything like that and um I think if that is if you’re going to

continue with if you have that mentality I think real estate investing is going to be a challenge sadly and I say that

as someone who’s recovering and I think I just want to encourage the people i don’t want to be

on this show just as this person look at this guy he has it figured out he has a boutique hotel wow hey you i wish I

could do that i think just knowing that we all start somewhere and then just

when you do get started knowing that all you need to do know is the next step right like at this phase I look back and

I’m just like I even still question i’m like “Wow.” Like how are we here it feels fake i’m sure you can relate Aaron

and as you’re working on those your mansions you just like you’ll get to a point and you’re getting to a point where you’re probably like “Wow look how

far we’ve come we’re here.” I mean if you look at like the 5year previous 5 year ago and you’d be like I would have

never just envisioned I’d be anywhere near this so I think that just says a lot to just we underestimate what we’re

capable of like in a slightly longer term and we overestimate what we should be doing in the short term people just

getting started oh I need to be doing a short-term rental business and they have 10 units under my belt and no I think

it’s important just to do the next step and that’s it sometimes it’s just running the numbers on a property

sometimes it’s calling that agent sometimes it’s making an offer sometimes it’s talking to a seller sometimes it’s

learning about watching a YouTube video about short-term rental systems like it it just one step at a time yeah yeah and

obviously I know we’re both students and I would like to think also friends with with coach Carson who I think has done

an incredible job of balancing the two dynamics one is setting a long-term vision and being bold and kind of like

setting goals that are in line with where you really want to be but instead of being constantly riddled with anxiety

about the fact that you’re not there yet then you take that vision you reel it back and you plan in like quarterly

sprints right come up with okay if this is where I want to be in 5 years or 3 years what can I do in the next 13 weeks

that will make consequential progress towards that goal and then once you’ve defined that you reel it all the way

back to what you’re saying which is do the next right thing what can I do today

or this week that will help me continue to progress along that direction but I

think that sometimes if you don’t have a clear idea of where you’re trying to go then you take action and you feel like

it’s not moving where you want to go because you haven’t taken the time to to figure that out and so that’s where I

think a lot of anxiety comes from is when people they have this deep inner

desire to make progress but they don’t necessarily know what they want to make progress toward and so I think there’s

it’s it is a tough thing to balance but ultimately like you you also learn what

you want to do and what you don’t want to do by trying things like there yes like you’ve found your thing right now

that resonates really well with you you’ve built a lifestyle around it you guys are really happy you’ve got a rich personal life and you’ve got

partnerships friendships and and a life that you love but I’m quite sure that along the way there were times where you

weren’t as comfortable or you were still trying to find your footing and you didn’t have this crystal clear vision of

where you’re going to end up and you probably just worked your way through it and figured it out and same here i had

no clue idea that I was going to be working with my wife so closely to build

residential assisted living mansions right that wasn’t even on my radar a few years ago but it was about taking those

incremental steps and we knew we wanted to build a life where we could have a little more time freedom financial

flexibility to be with our kids and so we just kept moving in that direction and then the path revealed itself and so

I think that’s to your point like people see folks like yourself who you have

something very solid right now but you’re very open and honest about the journey to get there and sometimes I

think that people need to pay a little closer attention to the original beginning of the story than just

focusing on that guy has something that I want but I don’t have it’s no focus on

what you did to actually get to the position you’re in now sure i wanted to mention everything you said was spot on

and it made me think of this book that I read the gap in the gain and for a lot of overachievers or high performing

people struggle with what you were talking about because they’re not there yet and they want to be there and they beat themselves up because they’re just

they should be further along and basically the concept is like celebrating basically looking backwards

at your lives and measuring like where you are today versus where you were yesterday even last year and I think we

should celebrate the small wins we should celebrate everything there was times where no joke I was literally

depressed during just the process of starting this business and operating this business and getting out of bed was

tough so so I look back at that and say man I’m so glad that Katie was there to support me and get out of bed and

sometimes it was just eating and just sending an email or whatever it could be the smallest thing and I’m so glad I’m

in a place right now where thankfully I’ve got I’ve gotten out of that and I have more tools to deal with those types

of things if I do fall back but yeah I think we we need to just give ourselves credit all of us we’re doing well and

celebrate the small wins it can be anything literally anything yeah the gap in the gain is one of my

favorite books as of recent i went to a conference with Dr benjamin Hardy who’s one of the co-authors of that book and I

do think that people probably get tired of hearing me talk about mindset stuff both in my ep solo episodes and with my

guests cuz a lot of the times I that’s where I tend to take these conversations rather than necessarily getting too deep

in the weeds on the tactics there’s plenty of stuff out there about the tactics but I do think the journey and the way that people think about

themselves and the journey they’re on is probably a lot more powerful than learning yet another little micro tactic

there’s a time and a place for that stuff but for those who are still trying to chart their path I would focus on the

mindset for sure so one element on that that kind of last topic I want to hit on here is you mentioned partnerships right

so you guys went from being just you and Katie building your own thing making

mistakes it was your own money so maybe there wasn’t as much pressure to you could make those mistakes and it wasn’t

affecting a group of investors or a partner or anything like that to now you have this project where you do have a

partner who you respect and you care about and you do have not only expectations of your customers but you

have kind of someone else to be accountable to so I guess with that what were some of the biggest shifts that you

had to make in order to feel like you were prepared for that making that leap

wow that’s a big question no it’s a good question i think it should be talked about more though

but you’re exactly right so going from using I think a lot of gurus and content

creators talk about because they’re at the level where they’re raising capital and they’re JVing properties and doing

stuff like that and doing syndications it’s becomes the norm but I think it’s such a small percentage of investors

when we talk about the small and mighty investor in our online community as well we talk about like the majority of us

are just they have a handful of properties in their name right they close with their own money and that’s

that’s huge that’s and that’s way more than the average person by far but I think we lose touch as people that are

partnering and raising capital or using as we call OPM other people’s money but I think it’s less talked about how

stressful that can be and that was the biggest thing that probably um stressed

me out and I just I wanted to do so well i wanted to succeed i did not want to

fail my partner of course I don’t want to fail and lose our own money right no one likes losing money but at the end of

the day you can live with that you’re like I took the risk i messed up that’s my money but the potential of losing someone else’s money is that’s next

level because for me it was less even about the losing the money per se or failing it was more about I don’t want

to mess up our friendship i don’t want to mess up the relationship and I think that’s something that people should I

think tread like tread carefully or move cautiously when they’re raising money i think I didn’t realize this at the time

but so for the longest time I’ll back up a little bit i had this opportunity my my now partner was like “Oh yeah let’s

do something see if you find a property that makes sense write it by me we’ll run the numbers together.” That type of

thing and I was like “Great sweet cool.” And I thought I was I thought it was no big deal and then I found a property and

then we started running the numbers and I pretty much had the green light make an offer negotiate it and I was like I

froze i literally was paralyzed because I was just I didn’t realize it at the time but I was just thinking about all

these things what if I fail and I stopped we I we stopped negotiating for

a couple months and the deal just went flat and just just sat there until there was something inside of me that was like

just eating me alive like it was on my birthday and I was like looking at myself in the mirror literally and I was

just like if I don’t do this I’m just going to question it forever i’m going to regret it like what would have

happened so for me everyone’s at the same but it was like I just got to the point where I was like I can’t not do

this and then I thankfully I got to experience the joys of partnerships and

I think you can go a lot farther with partnerships but I think this is one

thing that everybody if they’re thinking about doing partnerships they need to think about who they’re partnering with i know this is not a very technical

thing of course you need to find someone that has the capital that knows how to knows the mechanics of investing and

that kind of thing but you got to make sure that you you jive right you vibe if

you have a partner that’s very just overly analytical and you’re not and you butt or you just can’t even communicate

because they’re going to get upset if you don’t you’re not submitting your your monthly reports and that’s going to

stress you out like probably not the best partnership right if you can’t be friends if you can’t like sit and have dinner together and just talk human to

human and be friends imagine what things are going to go or you’re struggling right and you’re not cash flowing your

first year so I think the biggest jump is in investing is going from using your own money to on using somebody else’s

money and I think it should not be taken lightly so I just wanted to say get off my soap box here and just say so just if

you’re not doing that already like working with someone else just give don’t beat yourself up it’s actually

it’s hard it’s stressful taking somebody else’s money so some people do their whole career and never partner and I

think that’s okay right i don’t think you have to i think the push is build up your portfolio and then syndicate because then you’ve made it right i

don’t think you necessarily have to do that it’s not for everyone so I don’t know again I ranted there but yeah I

think it because it is almost I went crazy i stressed myself out too much because I don’t think I was quite

ready if I’m being honest on this show here but I think I doing the partnership

allowed me to become the person that I needed to be a good partner and I think it it literally changed my life so I’m

grateful for that i’m glad I have the best partner that I could possibly have and I can say that with complete

confidence and yeah I’m so glad and I want to do more and we’re doing more deals but but yeah I think it’s

something you have to really think about look within make sure that’s really what you want and sometimes again going back

to you do have to take action but just be aware that it’s not gonna be easy and

hopefully you can find a partner that you fit well together and you kind of yeah it’s good to start just with your

own circle too like just don’t go and try to raise money from everybody random

people on the internet it’s not advisable I don’t think um first yeah start start within your closer circle

absolutely there’s so many good stuff things in what you just said and I guess a couple things I just want to highlight

first of all I think there is a difference too between taking outside investor capital and creating a long-term operational partnership

sometimes someone’s bringing both maybe they’re bringing money and they’re going to be involved in a joint venture or

something where they’re maybe providing advisory service but letting you run the day-to-day which I think is closer to

your current arrangement but all of these things involve responsibility you the second you take someone else’s money

you become a steward of that money you have a responsibility and I think it does change behavior too when it’s my

own money if I make a mistake and I lose $1,000 because I was careless about calling in a deferring maintenance or

doing something that’s a little sloppy it doesn’t feel as consequential to me because I’m the one paying the price but

if that same thousand mistake I had to go communicate to a partner or an investor I would be very it that would

hit me a lot harder therefore I would do everything in my power to avoid that thousand mistake so I think it does

change behavior and that’s probably some of the pressure you were feeling when you felt like “Oh maybe I’m not ready.” But I would challenge that you were

ready because clearly it’s all worked out and you figured out how to like you said become like evolve into the person

that can handle that responsibility can handle that relationship and respects the power of that arrangement and the

other thing I just want to highlight is it’s sometimes people turn to partnerships to solve a shortterm

problem or a short-term pain point i don’t have enough money i don’t have enough time i don’t have the specific

knowledge to solve this one pain point in my business or my goals without

considering all the stuff you mentioned which is can I grow alongside this person can I communicate with this

person would I want to not could I but would I want to sit at a dinner table

with them for an hour and a half and have a leisurely meal and talk about more than just business right like those

are important questions to ask and even if you might be able to solve whatever that transactional need is in the moment

that’s not what a partnership is partnership is not just a series of occasional transactions at least not in

my mind it’s a long-term living breathing organic relationship between multiple people humans and you have to

be able to respect each other grow together and solve problems together so I think you summarize it really well and

it’s such an important topic it’s really great to hear your whole story and such it’s such a cool evolution i love I said

it at the top I’ll say it again to close it out i love that you’ve never lost sight of what it means to adventure and

be connected to the physical world around you that’s something I really admire about both you and Katie and

you’ve built a business that supports that which I think is the underlying kind of moral of this story and this

episode is that can be done you just have to know what you want you have to be willing to take action and listen to

the signals along the way so anything else you want to leave the audience with Joe i enjoyed this a lot man man I wish

we had more time it went by so fast yeah I enjoyed it too thanks for having me on no I just want to leave the listeners

with just just a mega sense of encouragement and just just the message

that like if I can do it you can too i’m just a Joe Schmo dirt bag that came from through hiking the Appalachian Trail to

managing a nice short-term rental portfolio and I want to say just give

yourself credit everyone we’re all starting somewhere i I used to beat myself up as well um because I I wasn’t

meeting my goals today so just celebrate the small wins and enjoy life it’s

beautiful and yeah if you guys want to connect just hit me up i’m always available to to help

i love it man joe’s a total go-giver i highly recommend reaching out to him if you’re getting into short-term rentals

or if you just want to talk about the journey of real estate investing or anything yeah he’s a great guy highly

recommend you reach out i will drop your handles and the link to Switchback Suites in the show notes and we’ll be

doing this again sometime soon i can tell you that much sounds great thanks for coming on man thanks Aaron thank you

for making it to the end of today’s episode as you may know podcasts are very difficult to grow organically if

you’re getting value from today’s episode I’d deeply appreciate if you can take 30 seconds to leave my show a fivestar rating and review this will go

a long way to helping me reach more listeners just like you thank you so much in advance

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