September 9, 2025 • 27 mins
Veterans and transitioning servicemembers often face challenges when seeking civilian careers.
Former Army officer Kirby Atwell faced burnout in his first attempt at entrepreneurship post service. He stayed true to his calling, seeking a mission that would bring him freedom after his military service.
Learn how he knew when to move on and how to make a pivot to unlock a more rewarding business that supports veterans in need in the real estate field. Tune in to the second episode of Veteran Entrepreneurs, a special four-part podcast series from The American Legion Tango Alpha Lima podcast.
Special Guest: Kirby Atwell.
Links:
- Watch video of this episode on YouTube
- Living Off Rentals
- Dune Dwellings: Premium Vacation Rentals Near Lake Michigan
- Sell My House Fast IN – We buy houses in Michigan City – Green Vet Homes
- Rich Dad Poor Dad: The #1 Best-Selling Personal Finance Book Ever
- Home - D'Aniello Institute for Veterans and Military Families
- Bunker Labs – Perkins&Will
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to Spotlight Veterans Entrepreneurship, a special
series from the American LegionsTal podcast.
I'm your host, Ashley Gorbulcha.In each episode, we sit down
with a veteran or military spouse entrepreneur who is
leading the charge across different industries.
We will explore the challenges, breakthroughs and real stories
(00:21):
behind building a business during and after military
service. Today we are joined with Kirby
Atwell, AUS Army veteran, real estate investor and host of
Living Off Rentals podcast. After 11 years of military
service, Kirby built a thriving business focused on high cash
flowing vacation rentals and nowhelps others achieve financial
(00:42):
freedom through strategic investing and education.
Kirby, welcome to the Tangua Filima podcast.
Actually it's awesome to be here.
Thanks for having me. Of course, of course, I am
always impressed with those who are managing all things house
related. As someone who bought a home
more recently in his own home prior, I can only imagine the
(01:06):
the quantity, quality and competency that business acumen
that comes with having multiple properties.
And I know our listeners are very excited to hear from you
today every. Every property has unique
challenges, that's for sure. Yes, yes, after I got some of
the first bills, I realized whatI got myself into.
That all being said, let's get into it.
(01:28):
So, Army officer to Airbnb entrepreneur, you bought your
first rental property in 2006. Well, still an active duty.
What sparks your interest in real estate investing?
And how did your military mindset influence your early
decisions? As Yeah.
Yeah. So in the intro, it made it
sound like such a seamless transition from, you know, Army
officer to very successful, you know, real estate investor, but
(01:52):
that's not exactly how it went. But to answer your question, you
know, in in, I was commissioned 2005 out of West Point and I
picked up the book Rich Dad, Poor Dad.
And I sometimes call it the gateway drug in the real estate
investing because there's so many people that come on my
podcast and have the same story.They read that book and they're
like, this is what I want to do.And so not knowing much of
(02:14):
anything beyond just reading thebook, I went out and bought my
first rental property and learned a lot.
I was in El Paso, TX, I was stationed at Fort Bliss at the
time and so learned a lot on that one.
Luckily is a very low cost property and a good one to cut
your teeth on and then kind of caught the bug of real estate
investing. I was like, you know, this is
something I could do the rest ofmy life regardless of what else
(02:36):
I'm doing, you know, And so thatreally appealed to me.
And so bought a couple more whenI was in the Army and then
eventually transitioned out in 2011 and that's when I jumped
into a full time. That's impressive and it's so
interesting to hear you say the rich dad, poor dad.
I read that book when I was 16 or 17 years old and only reason
(03:00):
I had heard about this is I wentto a high school friend of
mine's house and they were having board game night.
And for those who are not familiar, Rich Dad, Poor dad,
the the author of that book, there is an entire investment
strategy money game that they created to increase financial
literacy. And actually played that for the
(03:20):
first time when I was in high school.
And it was so fascinating to me.And nobody was really talking
about money. And like, I really credit that
family for putting me on the right track.
And so it's so nice to hear thatand not, I guess I was
surprising to hear that a lot offolks in your space are also
leaning into that. Yeah.
And I asked Robert Kiyosaki, who's the author of that book,
(03:42):
and it's, it's the number one personal finance book of all
time. And I asked him, I said, why is
this one, you know, such a, a profound book?
Because he, he was on the 100th episode of my, my podcast.
And I said, why did they have this impact?
So many people say the same thing.
And he said, once you figure that out, come back and let me
know because he said, I've been trying to figure that out ever
(04:03):
since it was written. But you know, it's just one of
those kind of lightning in a bottle type things.
And it just has a big impact on a lot of people.
Absolutely. I, I couldn't agree more if that
memory, I haven't revisited thatin a very long time.
So thank you, Kirby, thank you. So you've transitioned out,
(04:26):
you've started accumulating properties, right?
So let let's talk about from thefirst property to full scale
operation, right. You said success is not
necessarily linear. It's kind of some straight Marks
and it's squigglies and then stuff gets messy to figure it
out. So you went from owning a single
rental to building a rehab of vacation rental empire.
(04:49):
What were your key operational decisions or market systems that
allowed you to scale efficientlywithout?
Burning out. So I'll just kind of share the
story a little bit of how this came about.
So I, I left the military in 2011 and I went from being the
commander of a homeland defense site in northern Japan.
We, we had a radar there, billion dollar radar that
monitored North Korea and I had 100 guys that around my site and
(05:13):
I was in charge of. And so it was kind of a, a
higher profile job. And I went from that to moving
into my parents basement and trying to start this real estate
investment company basically overnight.
I got out of the military, flew home and, and I knew this is
what I wanted to do. And this is not the path that I
would recommend for most entrepreneurs.
(05:34):
Like, you know, it, it's, it's alot more prudent to build a
bridge before you just like jumpoff.
But I was just like, you know what, I'll figure this out.
I had visions of having this straight line to success.
And I thought, you know, I'm just going to do all these deals
and make a bunch of money and, and it was a struggle.
You know, I, I lived in my parents basement for about a
(05:57):
year and a half. I was going to school, Business
School at night, trying to learnwhile I was implementing during
the day, trying to build this business And at the same time
going through this transition of, you know, going from Captain
Atwell to just some guy living in my parents basement who says
he's a real estate investor but has never really done many
deals. So I was kind of reinventing
(06:19):
myself at the same time. And so it took a while to get
traction and didn't really know what strategy I was going to
pursue within real estate. I just knew I was attracted to
real estate and at the time, youknow, I, I didn't have AW2
income anymore because that wentaway with the military.
And so financing was, was difficult.
(06:40):
And so I partnered with a couplefriends of mine from high school
and we decided to start a, a real estate flipping company
initially. And so we started flipping one
property. You know, we rehabbed it, bought
it, rehabbed it and sold it. And then we did a few at a time.
And over the next five years, wedid 70 flips around the
Chicagoland area. And, you know, it was
(07:01):
interesting because we kept kindof being recognized as as being
successful. People were saying, wow, you're
doing all these deals. But it we're, we felt like we're
on this hamster wheel. Every time we do a flip, we'd
make some money, it'd go right back into the business and we'd
be back at Square 1 and you could never get ahead of it.
(07:21):
We thought we'd just do more deals.
We do bigger deals. Eventually, you know, we'll get
ahead of this and we'll start making more profit.
And that just was never the case.
You know, the, the, the, the infrastructure, we kept
thinking, well, we need to hire more people and we need to send
out more marketing and get need to get an office.
And so the, the overhead just kept growing along with the more
(07:42):
deals we were doing. So after five years of this,
this is when I realized, OK, what I really need to create is
passive income. You know, that that was what got
me interested in real estate in the 1st place, you know,
perpetual income coming in whileI could do other things.
And so that's when I transition into rental properties in 2016
(08:05):
ish. And initially it was long term
rentals, which was nice. You know, I, I started to
experience the power of cash flow, monthly recurring income.
But then I realized once we moved from Chicago over to
Northwest Indiana, I tried out short term rentals and I tried
these this niche of lower cost, higher cash flowing short term
(08:26):
rentals, which are kind of like the non traditional, like most
people think of high end short term rentals when they think of
vacation rentals or Airbnb's. But these are typically smaller
multi units in more affordable areas that can cash flow really
well. And so transition into that and,
and realize that the cash flow was much better.
(08:48):
And so since then, since 2017, we've built a business around
this and I sold off all the longterm rentals and it's just been
it's, it's totally changed my family's life.
Wow, that's incredible. And you stated that it's bit of
a non traditional thing to do. So how did you kind of did that
(09:11):
come from you just kind of doingthe the analysis yourself or did
you have a mentor or somebody who was like?
Yeah, it's a great question. And I wish I could say I was
just really smart and, like, figured this thing out, but that
wasn't how it went. So we moved from Chicago to
Northwest Indiana. So we we're we bought a
property. It's the town's called Beverly
Shores right on the southern tipof Lake MI.
(09:33):
And you know, it was all 1970s inside, had the green shag
carpet and the wood panelling and you know, it's like a time
capsule to 1975. So we were going to rehab the
house and move into it ourselvesand it had this unfinished walk
out basement. And so we've been doing some
long term rentals. And I said to my wife, I said,
you know, we've got this unfinished basement.
(09:55):
I said we could turn it into like a game room or TV room or
something for us. But what if we just, you know,
turn it into a separate one bedroom apartment and it has its
own entrance? And I keep hearing about this
Airbnb thing. What if we just try it and see
what happens? So we did.
And we thought worst case scenario, it's adding equity to
the property. You know, we could use it as a
long term rental. So it seemed like a pretty safe
(10:18):
thing to do. And we rented, we start renting
it right before Memorial Day that year and it just started
booking up like crazy. And it booked up the whole
summer. We made $22,000 that summer on
this windowless small one bedroom apartment and I was
sitting there going, I have longterm rentals that are entire
(10:38):
houses that don't make $22,000 in a whole year.
And so we just made this on thisdinky little apartment.
So that's when the light bulb went off and there's this
epiphany of like, OK, what if wecould scale this?
And, and I started looking at other properties around there
and think and, and seeing that based on the other ones that are
on Airbnb already, I can see kind of where their pricing is
(11:00):
and how many, how often they're getting booked.
I was like, you know, worst casescenario, we can always
transition back to a long term rental, but let's just try this.
And we just started learning lesson after lesson, make every
mistake along the way, but then slowly over time optimized it to
where you know, the properties just kept getting better and
better. That's impressive.
(11:25):
That is an impressive amount of cash flow in a summer.
Wow. My gosh, My gosh, all the
listeners out there. Yeah, exactly.
And we've never, and by the way,we've never looked back from
that because we're always going to.
We call it a house hack where basically you use some portion
of your house to rent out on on as a short term rental and that
(11:50):
can offset your costs and basically allow you to live cost
free from a from a housing standpoint.
And so we did that in the basement for a few years.
Then we wanted to move to this farm that we live on now.
And so the barn that I'm standing in where my my office
and podcast recording studio is also on the other side of this
wall has an Airbnb in it. And our guest just checked out
(12:11):
this morning, the cleaners in there right now and we have a
new guest checking at 4:00 PM. And, you know, it just stays
booked up and that 800 square foot apartment pays for a 45
acre farm because it just stays booked up and it really doesn't
impact our life. So it can be such a you can get
creative around, you know, some space on your property, whether
it's a tree house Outback or a basement or a finished garage or
(12:34):
a barn that can pay for the entire property.
Right. And I imagine too obviously like
you've got the business account set up, you have your own
personal finances, right? But when you're thinking about
write offs for your business, particularly because it's tied
to your house and equity and it's, there's got to be, it's
(12:57):
got to make you feel good sometimes, right?
Because you're like, write that off.
I can write that off. And I think that I'm sure
listeners would be interested tokind of learn just a bit about
how someone that works when you have an Airbnb, just very
briefly like how you as your home as the homeowner use the
Airbnb and then like what are the some of the write offs or
(13:18):
some of the perks and things that can be utilized?
Yeah, absolutely. That's a great point.
And it's, it's slightly different whether you have a a
Airbnb as part of your personal home or whether it's a separate
Airbnb. But either way, from a tax
standpoint, you know, the IRS really encourages you to own
businesses and own real estate, right?
(13:38):
There's a lot of benefits that come with that from a tax
standpoint. And short term rentals is
actually one of the best out there.
There's a, there's a, a rule called the short term rental tax
loophole. You can look it up, but it's, it
basically allows you to write off a big portion of the, the
(13:59):
short term rental, the value of the short term rental against
your active income, your W2 income.
So with long term rentals, you can't do this because it's
considered passive income and a passive business.
So you can't write off those losses against active income.
But with short term rentals, it's more considered more of an
active business. And so you can write in in with
(14:21):
the new tax bill that just went through, you can bonus
depreciate up to 100% in the first year.
So you take a portion of the property, basically anything
that's going to wear out in, I believe it's 20 years or less.
And, and so you take that portion of the property and you
can offset that entire 100% of that portion in the first year
(14:44):
against your, your W2 income. So a lot of people who own short
term rentals don't pay any income taxes.
And, and so a lot of like high income earners or, you know,
people with W2 jobs that are paying a huge tax bill will buy
a short term rental just for thetax benefits set, you know, let
alone the, the, the cash flow that you can create as well.
(15:07):
But the tax benefits are huge. You're right.
Oh wow, makes me rethink. I'm like looking around my
property. Don't mind me.
I'm like, what spaces can I use?Because you're, you're
absolutely right. There's, there's plenty of
incentives. That's why we're doing a podcast
(15:28):
series on entrepreneurship and business, because people need to
know about these things. And we do live in a, a, a time
where the housing market has been a little, little, I'm
trying to find the right word. We'll just say unaffordable for
most. So it's, it's interesting to see
(15:49):
that there's a, an uptick in like vacation rentals and homes
or short term rentals. Well, the other the other cool
thing too. Is this is incredibly
educational and I know of listeners and viewers will
appreciate it. Yeah, yeah, yeah, absolutely.
And and you know another thing too, I know a lot of the the
listeners are veterans. And so the cool thing is you can
(16:12):
use your VA loan to do this as well.
So if you think about it, you can buy a property up to 4 units
that, and this is, you know, our, our farm is financed with
the VA loan. So you get 100% financing.
So you bring $0.00 to the table.And if you carve out one of
these spaces, whether it's another unit, you buy 2 unit or
(16:34):
it's a farm like this and you turn a barn into an Airbnb, you
can live for free. Then you know that that space
can pay for the entire mortgage.So you brought $0.00 to the
table to purchase a property andthen you pay on a monthly basis
$0.00 in a mortgage because it'spaid by somebody else.
So essentially you can live in your house for free.
(16:57):
You know, so it's, it's really incredible once you start to get
a little bit creative and, and understand what's available to
you because this is, I mean, theVA loan is one of the best
benefits out there. Absolutely as a proud VA home
loan user, not once but twice. I think the third time I use it,
(17:20):
I will likely buy a farm maybe looking in West Virginia.
Just saying, you know, nice. Not too far away, not too close,
all the things. Yeah, exactly.
But gosh, I I'm familiar with somany different land grant
programs. Just again, this weird niche.
I will go down a rabbit hole, but I was like, yeah, what if I
had a flower garden out in West Virginia?
(17:42):
So the more you talk about this,the more I'm like, I'm going to
add that to the next 10 year plan.
Maybe sooner might bump it up a bit re prioritize.
With that being said, so you have been able to additionally
create a your first vacation rental investment blueprint.
(18:06):
I would love for you to talk a little bit about how you've been
able to, you know, pass forward the knowledge in a way that
productizes your, your knowledgeand additional income and how
that's been a teachable platformfor you.
Yeah, absolutely. So I obviously enjoy real estate
(18:29):
a lot. I've just, like I said, I viewed
it as something that I'll do forever, you know, because you
could invest in real estate to your 100 years old.
It's not like, you know, being aathlete or being in the military
where eventually, you know, you're, you're done with that.
You know, it's, it's something that is more of a skill that
you, you, it, it truly is a skill like you get better and
better, you accumulate more knowledge and lessons learned
(18:51):
over time. And it's something you can just
do on the side if you want to while you're doing other things.
And so I was really passionate about it and passionate about
it. And I started my podcast in 2020
just just to kind of share what it was that I was doing.
You know, people were asking me about it.
I liked talking about it. And so I, I did that for a few
years while I was still working,I worked a corporate job because
(19:13):
after I was done flipping, I hadto go back and get a corporate
job while I was building up the rental portfolio because I
needed active income. And so I was still working a
corporate job, driving downtown to Chicago, but doing my podcast
on the side. And then a few years later,
after we accumulated 8 short term rentals, that was the goal
to be in a place where I could leave the full time job.
(19:37):
I left the job and people were I, I kind of built a little bit
more of a base of listeners to my podcast and people were
asking me, you know, this is great information, but like, can
you walk me through it or coach me on how, how this works?
And so it's kind of a natural transition for me to create a,
a, a coaching program around this where I walk people through
(19:57):
step by step exactly how to get their first really high cash
flowing short term rental. So I created that had no idea,
you know, what was going to workor what people wanted and just
have tweaked it over the years. This was four years ago.
And now I've worked with just over 300 people through that
program to create, you know, their own cash flow and buy
(20:20):
their own properties. And it's just been some of the
most fulfilling work I've done because.
Some people who started four years ago are now on their 15th
property, you know, and, and they people come back and say
this, you know, this cash flow has allowed me to do things that
I never would have been able to do otherwise.
And, and it's truly changed their lives.
And so, so it's just been reallyawesome to, I can still do
(20:42):
again, the real estate. I, I always have a, a deal or
two going at a time. We're building up our portfolio.
We have 39 short term rental listings at this point, but at
the same time I spend most of mytime working with other people
now to help them implement the same strategy.
Outstanding I am so happy that you've leaned into the education
(21:04):
piece because you're coaching and the we'll just say the
scribbly line of success, right?You're helping people probably
cut that spring in half. And so when we talk about like
balancing purpose with profit, they're on a farm.
(21:25):
You're raising a family, you're helping others, you're
educating, you're donating to veteran organizations, you're
wanting a profitable business. What does success look like to
you now compared to when you started?
And how do you stay grounded when things scale quickly?
Yeah, such a great question. So I think in the beginning, the
(21:49):
having the goal of just, you know, being able to provide for
yourself and, and make, you know, the, the goal of making
enough money to live off of, I think is a, is a very noble
goal. It's, it's a, it's a great goal
to have in the beginning becauseyou know, when, when you can't
pay for your groceries on a monthly basis, which I was
there, you know, it, it's hard to think about purpose beyond
(22:12):
that. You know, I'm going to go change
the world, but I can't, you know, pay for gas in my, my car.
So, so I think the first goal should be around providing for
yourself for, you know, like being able to put your own mask
on before you help other people.And but then very quickly, if if
you put your mind to it and you're focused and you're
consistent, you're going to get there pretty quickly.
(22:34):
And so then at that point, it doesn't necessarily get you out
of bed the same way to make an extra $1000 or an extra $10,000
or an extra $50,000 a month or whatever it, whatever your goal
is. The, the, the, the money just
doesn't, it's not as life changing as the, the first
amount that you need to live offof.
(22:54):
And so then purpose becomes the question, I think.
And, and so I think it requires you to start doing some self
reflection around what your values are and what's important
to you and what you want to contribute to the world.
And, and so once you start doingthat, I think it changes the way
(23:15):
you operate. And so for us, it was like
initially we were like, OK, if we can get to 8 short term
rentals, we can leave our full time jobs and, and live off this
and, and live the lifestyle thatwe want.
We have three young kids with one on the way.
And we wanted to spend a lot of time with the kids.
We wanted to get them involved in the business.
We didn't want to be the parentsthat left at 6:00 AM and got
(23:37):
home at 6:00 PM and saw our kidsfor like 1/2 hour before they
went to bed, you know, so that we worked really hard to get
there. And then after that, the
question comes up, what's the next step?
You know, is it just to be able to do nothing then the rest of
your life, you know, not contribute anymore?
And so impact was the thing thatkept coming up for us.
And so the two ways that we really focus on impact is #1
(24:02):
helping other people to kind of follow the same strategy and get
to financial freedom themselves.And then number 2 is supporting
veterans. It's a, it's a huge 'cause that,
that we're really passionate about.
I used to, my full time job usedto be working for Bunker Labs,
which was a nonprofit that helpshelp the vets start businesses.
(24:23):
So I was around veterans all thetime.
And so we contribute a portion of our, our profit every year to
veteran related causes. And so then the intent of the
business becomes, you know, the purpose that you're pursuing as
opposed to just more profit. Absolutely.
(24:48):
The full, full circle. I'm I'm hearing you were at
Bunker Labs. I've had some connections with
that organization. I know that they're with
Syracuse right now. What a what a unique
opportunity. And I know that I've actually
been to a few Bunker events and it's actually where I met some
of my closest friends that I have photographed on the wall
over here actually at event. So, so thank you.
(25:12):
Thank you for creating that space for veterans like myself
and contributing to such a meaningful project, a group
organization. Words are hard sometimes, Kobe.
I do my day and I benefited fromit personally.
Really. You know, highly.
Before I joined the the. Organization.
(25:33):
I very, very fond of it. I'm of course, very fond of your
story. This is incredibly educational.
I think that a lot of people have questions about this space
but don't always necessarily like know who to speak with,
where to go. And you are doing amazing work
and you talk about impact and you are doing that, my friend.
(25:55):
Legacy is a beautiful thing and you're creating that and what
you're also creating with your family too, being able to be
present and be value aligned, have that self-awareness and you
know, be consistent. If there's one thing I've
noticed about entrepreneurs is that there's like a little bit
of madness slash obsession with what you want to do and that
(26:18):
purpose that drive. You have to re kind of configure
that and check in with yourself frequently because life happens,
pivots happen. And I just want to say thank you
so much for taking the time to share with all the listeners and
viewers your amazing story, Kirby.
(26:38):
So thank you so much for joiningus today.
We appreciate your insight and alphas.
We are happy that you've joined us as well.
As always, please subscribe, drop a rating to the show,
whether it's Apple Podcast, Spotify, or wherever you are
listening to your podcast. We look forward to speaking with
(27:00):
you soon. Thanks for having me.
Welcome to Spotlight Veterans Entrepreneurship, a special
series from the American LegionsTal podcast.
I'm your host, Ashley Gorbulcha.In each episode, we sit down
with a veteran or military spouse entrepreneur who is
leading the charge across different industries.
We will explore the challenges, breakthroughs and real stories
(00:21):
behind building a business during and after military
service. Today we are joined with Kirby
Atwell, AUS Army veteran, real estate investor and host of
Living Off Rentals podcast. After 11 years of military
service, Kirby built a thriving business focused on high cash
flowing vacation rentals and nowhelps others achieve financial
(00:42):
freedom through strategic investing and education.
Kirby, welcome to the Tangua Filima podcast.
Actually it's awesome to be here.
Thanks for having me. Of course, of course, I am
always impressed with those who are managing all things house
related. As someone who bought a home
more recently in his own home prior, I can only imagine the
(01:06):
the quantity, quality and competency that business acumen
that comes with having multiple properties.
And I know our listeners are very excited to hear from you
today every. Every property has unique
challenges, that's for sure. Yes, yes, after I got some of
the first bills, I realized whatI got myself into.
That all being said, let's get into it.
(01:28):
So, Army officer to Airbnb entrepreneur, you bought your
first rental property in 2006. Well, still an active duty.
What sparks your interest in real estate investing?
And how did your military mindset influence your early
decisions? As Yeah.
Yeah. So in the intro, it made it
sound like such a seamless transition from, you know, Army
officer to very successful, you know, real estate investor, but
(01:52):
that's not exactly how it went. But to answer your question, you
know, in in, I was commissioned 2005 out of West Point and I
picked up the book Rich Dad, Poor Dad.
And I sometimes call it the gateway drug in the real estate
investing because there's so many people that come on my
podcast and have the same story.They read that book and they're
like, this is what I want to do.And so not knowing much of
(02:14):
anything beyond just reading thebook, I went out and bought my
first rental property and learned a lot.
I was in El Paso, TX, I was stationed at Fort Bliss at the
time and so learned a lot on that one.
Luckily is a very low cost property and a good one to cut
your teeth on and then kind of caught the bug of real estate
investing. I was like, you know, this is
something I could do the rest ofmy life regardless of what else
(02:36):
I'm doing, you know, And so thatreally appealed to me.
And so bought a couple more whenI was in the Army and then
eventually transitioned out in 2011 and that's when I jumped
into a full time. That's impressive and it's so
interesting to hear you say the rich dad, poor dad.
I read that book when I was 16 or 17 years old and only reason
(03:00):
I had heard about this is I wentto a high school friend of
mine's house and they were having board game night.
And for those who are not familiar, Rich Dad, Poor dad,
the the author of that book, there is an entire investment
strategy money game that they created to increase financial
literacy. And actually played that for the
(03:20):
first time when I was in high school.
And it was so fascinating to me.And nobody was really talking
about money. And like, I really credit that
family for putting me on the right track.
And so it's so nice to hear thatand not, I guess I was
surprising to hear that a lot offolks in your space are also
leaning into that. Yeah.
And I asked Robert Kiyosaki, who's the author of that book,
(03:42):
and it's, it's the number one personal finance book of all
time. And I asked him, I said, why is
this one, you know, such a, a profound book?
Because he, he was on the 100th episode of my, my podcast.
And I said, why did they have this impact?
So many people say the same thing.
And he said, once you figure that out, come back and let me
know because he said, I've been trying to figure that out ever
(04:03):
since it was written. But you know, it's just one of
those kind of lightning in a bottle type things.
And it just has a big impact on a lot of people.
Absolutely. I, I couldn't agree more if that
memory, I haven't revisited thatin a very long time.
So thank you, Kirby, thank you. So you've transitioned out,
(04:26):
you've started accumulating properties, right?
So let let's talk about from thefirst property to full scale
operation, right. You said success is not
necessarily linear. It's kind of some straight Marks
and it's squigglies and then stuff gets messy to figure it
out. So you went from owning a single
rental to building a rehab of vacation rental empire.
(04:49):
What were your key operational decisions or market systems that
allowed you to scale efficientlywithout?
Burning out. So I'll just kind of share the
story a little bit of how this came about.
So I, I left the military in 2011 and I went from being the
commander of a homeland defense site in northern Japan.
We, we had a radar there, billion dollar radar that
monitored North Korea and I had 100 guys that around my site and
(05:13):
I was in charge of. And so it was kind of a, a
higher profile job. And I went from that to moving
into my parents basement and trying to start this real estate
investment company basically overnight.
I got out of the military, flew home and, and I knew this is
what I wanted to do. And this is not the path that I
would recommend for most entrepreneurs.
(05:34):
Like, you know, it, it's, it's alot more prudent to build a
bridge before you just like jumpoff.
But I was just like, you know what, I'll figure this out.
I had visions of having this straight line to success.
And I thought, you know, I'm just going to do all these deals
and make a bunch of money and, and it was a struggle.
You know, I, I lived in my parents basement for about a
(05:57):
year and a half. I was going to school, Business
School at night, trying to learnwhile I was implementing during
the day, trying to build this business And at the same time
going through this transition of, you know, going from Captain
Atwell to just some guy living in my parents basement who says
he's a real estate investor but has never really done many
deals. So I was kind of reinventing
(06:19):
myself at the same time. And so it took a while to get
traction and didn't really know what strategy I was going to
pursue within real estate. I just knew I was attracted to
real estate and at the time, youknow, I, I didn't have AW2
income anymore because that wentaway with the military.
And so financing was, was difficult.
(06:40):
And so I partnered with a couplefriends of mine from high school
and we decided to start a, a real estate flipping company
initially. And so we started flipping one
property. You know, we rehabbed it, bought
it, rehabbed it and sold it. And then we did a few at a time.
And over the next five years, wedid 70 flips around the
Chicagoland area. And, you know, it was
(07:01):
interesting because we kept kindof being recognized as as being
successful. People were saying, wow, you're
doing all these deals. But it we're, we felt like we're
on this hamster wheel. Every time we do a flip, we'd
make some money, it'd go right back into the business and we'd
be back at Square 1 and you could never get ahead of it.
(07:21):
We thought we'd just do more deals.
We do bigger deals. Eventually, you know, we'll get
ahead of this and we'll start making more profit.
And that just was never the case.
You know, the, the, the, the infrastructure, we kept
thinking, well, we need to hire more people and we need to send
out more marketing and get need to get an office.
And so the, the overhead just kept growing along with the more
(07:42):
deals we were doing. So after five years of this,
this is when I realized, OK, what I really need to create is
passive income. You know, that that was what got
me interested in real estate in the 1st place, you know,
perpetual income coming in whileI could do other things.
And so that's when I transition into rental properties in 2016
(08:05):
ish. And initially it was long term
rentals, which was nice. You know, I, I started to
experience the power of cash flow, monthly recurring income.
But then I realized once we moved from Chicago over to
Northwest Indiana, I tried out short term rentals and I tried
these this niche of lower cost, higher cash flowing short term
(08:26):
rentals, which are kind of like the non traditional, like most
people think of high end short term rentals when they think of
vacation rentals or Airbnb's. But these are typically smaller
multi units in more affordable areas that can cash flow really
well. And so transition into that and,
and realize that the cash flow was much better.
(08:48):
And so since then, since 2017, we've built a business around
this and I sold off all the longterm rentals and it's just been
it's, it's totally changed my family's life.
Wow, that's incredible. And you stated that it's bit of
a non traditional thing to do. So how did you kind of did that
(09:11):
come from you just kind of doingthe the analysis yourself or did
you have a mentor or somebody who was like?
Yeah, it's a great question. And I wish I could say I was
just really smart and, like, figured this thing out, but that
wasn't how it went. So we moved from Chicago to
Northwest Indiana. So we we're we bought a
property. It's the town's called Beverly
Shores right on the southern tipof Lake MI.
(09:33):
And you know, it was all 1970s inside, had the green shag
carpet and the wood panelling and you know, it's like a time
capsule to 1975. So we were going to rehab the
house and move into it ourselvesand it had this unfinished walk
out basement. And so we've been doing some
long term rentals. And I said to my wife, I said,
you know, we've got this unfinished basement.
(09:55):
I said we could turn it into like a game room or TV room or
something for us. But what if we just, you know,
turn it into a separate one bedroom apartment and it has its
own entrance? And I keep hearing about this
Airbnb thing. What if we just try it and see
what happens? So we did.
And we thought worst case scenario, it's adding equity to
the property. You know, we could use it as a
long term rental. So it seemed like a pretty safe
(10:18):
thing to do. And we rented, we start renting
it right before Memorial Day that year and it just started
booking up like crazy. And it booked up the whole
summer. We made $22,000 that summer on
this windowless small one bedroom apartment and I was
sitting there going, I have longterm rentals that are entire
(10:38):
houses that don't make $22,000 in a whole year.
And so we just made this on thisdinky little apartment.
So that's when the light bulb went off and there's this
epiphany of like, OK, what if wecould scale this?
And, and I started looking at other properties around there
and think and, and seeing that based on the other ones that are
on Airbnb already, I can see kind of where their pricing is
(11:00):
and how many, how often they're getting booked.
I was like, you know, worst casescenario, we can always
transition back to a long term rental, but let's just try this.
And we just started learning lesson after lesson, make every
mistake along the way, but then slowly over time optimized it to
where you know, the properties just kept getting better and
better. That's impressive.
(11:25):
That is an impressive amount of cash flow in a summer.
Wow. My gosh, My gosh, all the
listeners out there. Yeah, exactly.
And we've never, and by the way,we've never looked back from
that because we're always going to.
We call it a house hack where basically you use some portion
of your house to rent out on on as a short term rental and that
(11:50):
can offset your costs and basically allow you to live cost
free from a from a housing standpoint.
And so we did that in the basement for a few years.
Then we wanted to move to this farm that we live on now.
And so the barn that I'm standing in where my my office
and podcast recording studio is also on the other side of this
wall has an Airbnb in it. And our guest just checked out
(12:11):
this morning, the cleaners in there right now and we have a
new guest checking at 4:00 PM. And, you know, it just stays
booked up and that 800 square foot apartment pays for a 45
acre farm because it just stays booked up and it really doesn't
impact our life. So it can be such a you can get
creative around, you know, some space on your property, whether
it's a tree house Outback or a basement or a finished garage or
(12:34):
a barn that can pay for the entire property.
Right. And I imagine too obviously like
you've got the business account set up, you have your own
personal finances, right? But when you're thinking about
write offs for your business, particularly because it's tied
to your house and equity and it's, there's got to be, it's
(12:57):
got to make you feel good sometimes, right?
Because you're like, write that off.
I can write that off. And I think that I'm sure
listeners would be interested tokind of learn just a bit about
how someone that works when you have an Airbnb, just very
briefly like how you as your home as the homeowner use the
Airbnb and then like what are the some of the write offs or
(13:18):
some of the perks and things that can be utilized?
Yeah, absolutely. That's a great point.
And it's, it's slightly different whether you have a a
Airbnb as part of your personal home or whether it's a separate
Airbnb. But either way, from a tax
standpoint, you know, the IRS really encourages you to own
businesses and own real estate, right?
(13:38):
There's a lot of benefits that come with that from a tax
standpoint. And short term rentals is
actually one of the best out there.
There's a, there's a, a rule called the short term rental tax
loophole. You can look it up, but it's, it
basically allows you to write off a big portion of the, the
(13:59):
short term rental, the value of the short term rental against
your active income, your W2 income.
So with long term rentals, you can't do this because it's
considered passive income and a passive business.
So you can't write off those losses against active income.
But with short term rentals, it's more considered more of an
active business. And so you can write in in with
(14:21):
the new tax bill that just went through, you can bonus
depreciate up to 100% in the first year.
So you take a portion of the property, basically anything
that's going to wear out in, I believe it's 20 years or less.
And, and so you take that portion of the property and you
can offset that entire 100% of that portion in the first year
(14:44):
against your, your W2 income. So a lot of people who own short
term rentals don't pay any income taxes.
And, and so a lot of like high income earners or, you know,
people with W2 jobs that are paying a huge tax bill will buy
a short term rental just for thetax benefits set, you know, let
alone the, the, the cash flow that you can create as well.
(15:07):
But the tax benefits are huge. You're right.
Oh wow, makes me rethink. I'm like looking around my
property. Don't mind me.
I'm like, what spaces can I use?Because you're, you're
absolutely right. There's, there's plenty of
incentives. That's why we're doing a podcast
(15:28):
series on entrepreneurship and business, because people need to
know about these things. And we do live in a, a, a time
where the housing market has been a little, little, I'm
trying to find the right word. We'll just say unaffordable for
most. So it's, it's interesting to see
(15:49):
that there's a, an uptick in like vacation rentals and homes
or short term rentals. Well, the other the other cool
thing too. Is this is incredibly
educational and I know of listeners and viewers will
appreciate it. Yeah, yeah, yeah, absolutely.
And and you know another thing too, I know a lot of the the
listeners are veterans. And so the cool thing is you can
(16:12):
use your VA loan to do this as well.
So if you think about it, you can buy a property up to 4 units
that, and this is, you know, our, our farm is financed with
the VA loan. So you get 100% financing.
So you bring $0.00 to the table.And if you carve out one of
these spaces, whether it's another unit, you buy 2 unit or
(16:34):
it's a farm like this and you turn a barn into an Airbnb, you
can live for free. Then you know that that space
can pay for the entire mortgage.So you brought $0.00 to the
table to purchase a property andthen you pay on a monthly basis
$0.00 in a mortgage because it'spaid by somebody else.
So essentially you can live in your house for free.
(16:57):
You know, so it's, it's really incredible once you start to get
a little bit creative and, and understand what's available to
you because this is, I mean, theVA loan is one of the best
benefits out there. Absolutely as a proud VA home
loan user, not once but twice. I think the third time I use it,
(17:20):
I will likely buy a farm maybe looking in West Virginia.
Just saying, you know, nice. Not too far away, not too close,
all the things. Yeah, exactly.
But gosh, I I'm familiar with somany different land grant
programs. Just again, this weird niche.
I will go down a rabbit hole, but I was like, yeah, what if I
had a flower garden out in West Virginia?
(17:42):
So the more you talk about this,the more I'm like, I'm going to
add that to the next 10 year plan.
Maybe sooner might bump it up a bit re prioritize.
With that being said, so you have been able to additionally
create a your first vacation rental investment blueprint.
(18:06):
I would love for you to talk a little bit about how you've been
able to, you know, pass forward the knowledge in a way that
productizes your, your knowledgeand additional income and how
that's been a teachable platformfor you.
Yeah, absolutely. So I obviously enjoy real estate
(18:29):
a lot. I've just, like I said, I viewed
it as something that I'll do forever, you know, because you
could invest in real estate to your 100 years old.
It's not like, you know, being aathlete or being in the military
where eventually, you know, you're, you're done with that.
You know, it's, it's something that is more of a skill that
you, you, it, it truly is a skill like you get better and
better, you accumulate more knowledge and lessons learned
(18:51):
over time. And it's something you can just
do on the side if you want to while you're doing other things.
And so I was really passionate about it and passionate about
it. And I started my podcast in 2020
just just to kind of share what it was that I was doing.
You know, people were asking me about it.
I liked talking about it. And so I, I did that for a few
years while I was still working,I worked a corporate job because
(19:13):
after I was done flipping, I hadto go back and get a corporate
job while I was building up the rental portfolio because I
needed active income. And so I was still working a
corporate job, driving downtown to Chicago, but doing my podcast
on the side. And then a few years later,
after we accumulated 8 short term rentals, that was the goal
to be in a place where I could leave the full time job.
(19:37):
I left the job and people were I, I kind of built a little bit
more of a base of listeners to my podcast and people were
asking me, you know, this is great information, but like, can
you walk me through it or coach me on how, how this works?
And so it's kind of a natural transition for me to create a,
a, a coaching program around this where I walk people through
(19:57):
step by step exactly how to get their first really high cash
flowing short term rental. So I created that had no idea,
you know, what was going to workor what people wanted and just
have tweaked it over the years. This was four years ago.
And now I've worked with just over 300 people through that
program to create, you know, their own cash flow and buy
(20:20):
their own properties. And it's just been some of the
most fulfilling work I've done because.
Some people who started four years ago are now on their 15th
property, you know, and, and they people come back and say
this, you know, this cash flow has allowed me to do things that
I never would have been able to do otherwise.
And, and it's truly changed their lives.
And so, so it's just been reallyawesome to, I can still do
(20:42):
again, the real estate. I, I always have a, a deal or
two going at a time. We're building up our portfolio.
We have 39 short term rental listings at this point, but at
the same time I spend most of mytime working with other people
now to help them implement the same strategy.
Outstanding I am so happy that you've leaned into the education
(21:04):
piece because you're coaching and the we'll just say the
scribbly line of success, right?You're helping people probably
cut that spring in half. And so when we talk about like
balancing purpose with profit, they're on a farm.
(21:25):
You're raising a family, you're helping others, you're
educating, you're donating to veteran organizations, you're
wanting a profitable business. What does success look like to
you now compared to when you started?
And how do you stay grounded when things scale quickly?
Yeah, such a great question. So I think in the beginning, the
(21:49):
having the goal of just, you know, being able to provide for
yourself and, and make, you know, the, the goal of making
enough money to live off of, I think is a, is a very noble
goal. It's, it's a, it's a great goal
to have in the beginning becauseyou know, when, when you can't
pay for your groceries on a monthly basis, which I was
there, you know, it, it's hard to think about purpose beyond
(22:12):
that. You know, I'm going to go change
the world, but I can't, you know, pay for gas in my, my car.
So, so I think the first goal should be around providing for
yourself for, you know, like being able to put your own mask
on before you help other people.And but then very quickly, if if
you put your mind to it and you're focused and you're
consistent, you're going to get there pretty quickly.
(22:34):
And so then at that point, it doesn't necessarily get you out
of bed the same way to make an extra $1000 or an extra $10,000
or an extra $50,000 a month or whatever it, whatever your goal
is. The, the, the, the money just
doesn't, it's not as life changing as the, the first
amount that you need to live offof.
(22:54):
And so then purpose becomes the question, I think.
And, and so I think it requires you to start doing some self
reflection around what your values are and what's important
to you and what you want to contribute to the world.
And, and so once you start doingthat, I think it changes the way
(23:15):
you operate. And so for us, it was like
initially we were like, OK, if we can get to 8 short term
rentals, we can leave our full time jobs and, and live off this
and, and live the lifestyle thatwe want.
We have three young kids with one on the way.
And we wanted to spend a lot of time with the kids.
We wanted to get them involved in the business.
We didn't want to be the parentsthat left at 6:00 AM and got
(23:37):
home at 6:00 PM and saw our kidsfor like 1/2 hour before they
went to bed, you know, so that we worked really hard to get
there. And then after that, the
question comes up, what's the next step?
You know, is it just to be able to do nothing then the rest of
your life, you know, not contribute anymore?
And so impact was the thing thatkept coming up for us.
And so the two ways that we really focus on impact is #1
(24:02):
helping other people to kind of follow the same strategy and get
to financial freedom themselves.And then number 2 is supporting
veterans. It's a, it's a huge 'cause that,
that we're really passionate about.
I used to, my full time job usedto be working for Bunker Labs,
which was a nonprofit that helpshelp the vets start businesses.
(24:23):
So I was around veterans all thetime.
And so we contribute a portion of our, our profit every year to
veteran related causes. And so then the intent of the
business becomes, you know, the purpose that you're pursuing as
opposed to just more profit. Absolutely.
(24:48):
The full, full circle. I'm I'm hearing you were at
Bunker Labs. I've had some connections with
that organization. I know that they're with
Syracuse right now. What a what a unique
opportunity. And I know that I've actually
been to a few Bunker events and it's actually where I met some
of my closest friends that I have photographed on the wall
over here actually at event. So, so thank you.
(25:12):
Thank you for creating that space for veterans like myself
and contributing to such a meaningful project, a group
organization. Words are hard sometimes, Kobe.
I do my day and I benefited fromit personally.
Really. You know, highly.
Before I joined the the. Organization.
(25:33):
I very, very fond of it. I'm of course, very fond of your
story. This is incredibly educational.
I think that a lot of people have questions about this space
but don't always necessarily like know who to speak with,
where to go. And you are doing amazing work
and you talk about impact and you are doing that, my friend.
(25:55):
Legacy is a beautiful thing and you're creating that and what
you're also creating with your family too, being able to be
present and be value aligned, have that self-awareness and you
know, be consistent. If there's one thing I've
noticed about entrepreneurs is that there's like a little bit
of madness slash obsession with what you want to do and that
(26:18):
purpose that drive. You have to re kind of configure
that and check in with yourself frequently because life happens,
pivots happen. And I just want to say thank you
so much for taking the time to share with all the listeners and
viewers your amazing story, Kirby.
(26:38):
So thank you so much for joiningus today.
We appreciate your insight and alphas.
We are happy that you've joined us as well.
As always, please subscribe, drop a rating to the show,
whether it's Apple Podcast, Spotify, or wherever you are
listening to your podcast. We look forward to speaking with
(27:00):
you soon. Thanks for having me.
Popular Podcasts
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.