Amassing Wealth Series: Wealthy Woman Lawyer® Holly Draper Shares How She Invests in Short-Term Rentals

In this series, we’re tackling the question: “What do I do once I start amassing wealth through my law firm business?” There are many avenues you could venture down when it comes to investing your wealth, diversifying your assets, and achieving financial freedom. So, let’s explore one of the most popular investments of 2022 – short-term rentals!

Davina Frederick: Hi everyone
and welcome to the wealthy woman

lawyer podcast. I am Davina
Frederick, founder of wealthy

woman lawyer, which is a
coaching group for women law

firm owners who want to scale
their business to $3 million.

And I'm here today with Holly
Draper, who is a client and

friend. And she is the founder
of the Draper law firm in

McKinney, Texas. They do family
law, they offer family law

services exclusively. And if you
want to, we're gonna let her

introduce herself a little bit.
If you want more in depth

conversation that I've had with
Holly before about our law firm,

you want to go back and check
out the first episode that we

did together a few months back.
So go look for that, because

there's a lot of great stuff
there. But today, we're gonna

talk about something a little
bit different. And so I'm

excited to have you here again,
Holly, thank you. Good. Welcome

back.

Unknown: Sure. Thanks for having
me again.

Davina Frederick: Okay, great.
So why don't you tell us a

little bit about, just tell us a
little bit about the Draper

firm. So everybody has context
for sort of your business and

the scale of your business? And,
you know, that kind of thing?

Sure.

Unknown: So I started my own
firm Draper law firm back in

2000. And in 2008, beginning of
2009, there was a downturn in

the economy, legal Jobs were
hard to come by. So this was

the, you know, catalyst to jump
in on my own. I was true solo

for many years, and probably the
first five years, you know,

there was a lot of stress a lot
of am I gonna be able to pay the

mortgage, am I gonna be able to,
you know, where's the next

client gonna come from, but
eventually, you know, things

sort of took off, I now have
four other attorneys working for

me, we have three paralegals to
support staff. We do family law

exclusively. I started out as
kind of general, whatever walks

through the door. But over time,
I grew to love family law and

focused more and more onto that.
And now I also do family law

appeals statewide in Texas. Our
firm is unique, because we are

all virtual, we were virtual
before virtual was cool. So

before COVID, we were virtual.
We're even more virtual now. But

everyone works remote. And it's
worked great. And I wouldn't

trade it for the world.

Davina Frederick: Wonderful.
Yeah, you have a very unique

business model, which I, which I
absolutely love. And one of the

things that you did, again, we
cover this more in depth in the

other episode, but I just want
to touch on it here. So people

kind of understand how it's a
little bit different. One of the

things that that you did that
was different from what I see a

lot of other solos do when
they're growing, is you started

out by adding lawyers and you
added lawyers, we've added

several lawyers over the course
of a few years. And that sort of

is what catapulted your, your
growth, and got you to that high

six figure revenue mark. And
then we met and started

developing a really good
marketing strategy for you. And

now you're in the multi year in
multi seven figures, right. So

really, really tremendous
growth. So proud for you. Talk

about that just a little bit,
kind of what your thinking was

behind hiring lawyers.

Unknown: Sure, a lot of why I
wanted to grow my firm and had

other people working for me was
I wanted freedom. I wanted to be

able, my family loves to travel,
I wanted to be able to take

lengthy international vacations
and not have to come back to the

big huge pile of work, and not
have to worry about the fact

that I was making no money
during those two weeks that I

went to Europe. So by hiring
attorneys, I had people who

could go to mediation, who could
go to court who could do

everything that I could do, and
who could continue to run the

firm, and everything that was
needed while I was gone. And it

worked out fabulously well.

Davina Frederick: And all
virtual so everybody's remote,

you don't have you have a space
if you need a meeting, but those

things happen, virtually. And
you started that from the

beginning. So that's wonderful.
Alright, so we've kind of

touched on all of that. One
thing I just want to ask you

really quick though is how many
though at last count you said

you that your kids have been to
17 different countries. That's

probably up since I got that
figure. It's probably like 19 or

20 Now, isn't it?

Unknown: I don't know we we try
and count and then we always

forget and what about this place
about this place? It's

definitely got to be over 20

Davina Frederick: Yeah, really,
really cool opportunity for to

be able to take your kids at
such young ages for them to have

this experience these
experiences all ready to travel

and see different countries. So
super exciting that I you and I

have already discussed your law
firm. But I want to sort of what

I want to do today is I really
want to talk about what happens

when you get to a point where
you are making Making suddenly

your your cash rich, and you're
getting money coming in. And

then you're starting to think to
yourself, oh, my gosh, I need a

strategy like, what do I do with
this money? I can't keep it in

the bank account, if I keep
taking it, all of it, you know,

personally, I need some tax
strategy, I need some place to

invest this, what do I do,
because I think that is what

happens once people get over
that million dollar mark, is,

now we're at a new level, and
we're at a new level of thinking

about money, because up until
that million dollar mark, you're

focusing on paying bills, maybe
getting a bigger house may be

taking a couple of extra
vacations a year. But when you

start to get over that, and
you're making a much higher

personal income, as you are,
what kind of thoughts went

through your mind about that.

Unknown: So I'm very much not a
workaholic. And I'm not the type

of person that wants to work
until I die. I have always had

an aim towards how you know, I
want to be practicing law or

running my law firm, by choice,
not by not because I have to, to

pay the bills and whatnot. So
that has led to a lot of looking

for passive income streams, and,
you know, other investments and

ways of investing so that I'm
not doing the day to day work of

generating wealth and income.
And I've done a lot of reading

and listening to podcasts and
all those things about how

wealthy people do it and how
they you know, it's smart people

are wealthy people don't work
for money, they make money work

for them. Right? So it was
figuring out, okay, now I'm

doing really well with my law
firm, and what did we do to make

our money work for us so that we
have freedom to whether that's

to you know, get a golden visa
and live in Portugal, you know,

there are a lot of things, I
want options. And by investing

wisely and creating passive
income streams, that's gonna

give us freedom and choices.

Davina Frederick: So what are
some of the ideas that you

considered when you started
thinking about passive income

streams or multiple streams of
income? I've always

Unknown: believed in investing
in real estate. That was the

plan for a long time long before
we were in the position that

we're in now financially, we
started have assumed long term

rentals are that's what people
buy to invest in real estate and

use where we live used to be
able to buy a house for 100

grand and you know, put a little
money into it. And you know, you

might rent it out and make 500
ollars a month. And but the

house would appreciate a little
bit and you're getting a little

bit of income, and you're
building wealth that way. We

ultimately ended up selling our
long term rentals. And now we

invest in short term rentals,
because I've found that it is,

there's a much higher income
stream that comes from short

term rentals than long term
rentals. It's a little bit more

intensive in terms of work. But
if you have a good management

company, and you don't do the
work yourself, then it's worth

it.

Davina Frederick: Yeah, yeah. So
I want to has a lot to unpack

about this. I'm going to talk
about, um, you're, at what point

did you decide to switch from
long term to short term rentals?

Like, what was the year when did
that happen?

Unknown: So we sold our short
term rentals, probably in or not

our short term or long term
rentals, in probably 2016 2017.

We sold them to put a pool in at
our house at the time, and then

okay, well accumulate money, and
we'll do it again. And we didn't

invest again until start looking
at what we're going to invest

that and in again until about
early 2020. So pre COVID, 2020.

And our first short term rental
investment in our primary place,

we have done short term rental
investing has been in Broken

Bow, Oklahoma, and we live in
North Texas, and a lot of people

here were starting to invest
there and we started hearing

about it for about, you know,
maybe this is a good idea. So we

went up and it was a very
different market then looked at

a bunch of properties found a
great one that was a spec under

construction. If I knew then
what I know now I would have

pulled the trigger on several of
those properties because you

know, I could probably return to
it now but that was where we

started our short term rental
journey.

Davina Frederick: So why why was
broken bow appealing you were

hearing about it? What kinds of
things were you hearing that

made it appealing as a short
term rental market?

Unknown: So it was appealing
because it was close enough that

you could go check in on
something or deal with a crisis

if you had to. It was also
appealing because it's a very

year round destination. So a lot
of beach places, okay, you got

three or four months of summer
travel, and then nobody wants to

go there the rest of the year.
And I didn't do a ton of

research to begin with, it was
more just hearing things from

realtors and other investors
that were local and seeing what

they were doing and thinking I'd
like a piece of that.

Davina Frederick: Yeah, I think
it's interesting that you say

that true, true confession,
right? Like, I think people,

people often think that people
who invest in other projects, do

research ad nauseam, and
especially lawyers, but I often

find this the case when I have
conversations with people is

they hear about something from a
friend or relative or whatever.

And then they, you know, they
check it out. And then they go,

oh, you know, let's try it. So
for people listening, who think,

you know, I have to I'm not
educated enough to know enough.

Sometimes your education comes
through the doing, right. I

mean, you learn something with
your long term rentals that way,

too.

Unknown: Yeah. And it's, I
consider real estate to be

relatively low risk. Even if the
market takes a downturn, unless

you're buying way at the top.
Real Estate traditionally goes

up in value, and people are
going to take vacations, and I'm

also a risk taker. I'm not
afraid to take a risk and a bit,

you know, if it doesn't work
out, then I learned my lesson.

But

Davina Frederick: yeah, you make
another decision. Right? Yeah,

Unknown: I'll find something
else to dry. She doesn't work

out.

Davina Frederick: Yeah. Um, you
you also your timing, though,

really worked out? I mean,
obviously, the pandemic was a

terrible thing. But it was also
a really good thing for short

term, that short term rental
business, right? Did you find

that to be the case?

Unknown: Oh, absolutely. If
because we bought only did our

first property I mean, the
market has gone through the

roof, we bought our first
property. So when you buy short

term rental, if it's your first
short term rental in a

particular market, you only need
to put 10% down if you're doing

a second home loan, so you're
putting a relatively minimal

investment down. So we put it
down, you know, all in between

the downpayment and furnishing
it. And all of our out of pocket

expenses, we probably put
$80,000 into this first

property. In the first year, we
net $80,000, in income from

rentals, and we sold it after 14
months, and we net 265,000 on

the sale. Wow. So we, you know,
we had to do, you don't wanna

pay taxes on that gain. So then
we split that into two

properties in Broken Bow, one
that we put 10% down, and when

we had to put more down because
you can only have the one second

home at a time. But you know, we
contracted for one of those two

properties before it was even
started. So it was just a slab,

basically. And so that one has
gone up in value significantly

to both of them have the one
that was new construction has

probably gone up 50% in value,
since we bought it. The market

has taken a turn down from the
peak. But COVID was driving the

people to want to go somewhere
that they didn't have to fly. So

everybody in North Texas was
driving to Broken Bow for

vacations, and then you're in a
place all by yourself away from

everybody else. But that allowed
a lot of people to get to know

about it. And with the growth in
North Texas, it's booming

northern suburbs, tons of
effluent people moving in here

all the time. Those are people
who are going to want to get

away for the weekend. Those are
going to people who are going to

want to you know, not just go to
Europe for the summer, they're

also going to want to go spend a
week at my broken bow Lake and

take the boat

Davina Frederick: so they gotta
lake up there you got trails,

the forest, you know, there's
some parks around there and

stuff like that. So it attracts
people who like those outdoor

activities. Um, I have some
questions about the your actual

deals, one of the things so one
of the things that you said was

it's only 10% Down with your
vacation home. I think most

people think I've got to come up
with like after my first house

where I got the FHA loan, I've
got to come up with 20% If I

want to buy another house, so
talk a little bit about about

more of that of that and how you
found out about it and you know,

all of that.

Unknown: So I connected with a
lender who does a lot of Broken

Bow cabin lending. I've worked
with a couple bowl and they both

exclusively are not exclusively
but largely did that. And so you

want a lender who knows the
market who knows what this

investment is like and all of
that. With 10% down, it depends

a lot on how expensive is the
property. So we have one that's

well over the conforming loan
limits. So if you get over that,

then you have to deal with a
jumbo loan. There's a lot more

involved with that. But you can
still do 10% down and have a

jumbo loan. Obviously, interest
rates are going up. It's a lot.

What more to consider with that.
But so our second one, we had

to, because well, so we'll have
numbers two and three, really,

number one was sold, we move put
that into numbers two and three,

Davina Frederick: before you get
into that lbs Why did you sell

number one

Unknown: we sold because the
prices were going up so

dramatically. And even though
our family enjoyed going to the

cabin, it was really about the
investment. And we started when

we saw the price is going up and
up and up. And we started asking

everything's for sale. Just
what's the price point and when

do you know when to sell. So
another cabin owner had given

him the formula they'd come up
with, which was if you can net

more on the sale, and you can
net in four years worth of

income you sell. So at the
point, I heard that we weren't

there yet. But then when the
prices kept going up, we

realized great, we're past that
figure. And maybe we can turn

one cabin into two with really
very little more out of pocket,

then it's going to build our
wealth. So that and the 1031

exchange, which is deferring
taxes when you're essentially

climbing the property ladder is
a really, it's designed to help

people build wealth.

Davina Frederick: Right? Right.
So now you had two cabins there

are at this time you had two
cabins here and give us an idea

of kind of the property values
and broken bones like when you

started and what they've sort of
climbed to, because I think you

know, it's a it's a pretty
wealthy community. In Broken

Bow,

Unknown: well, the cabins are
expensive. The community itself

would be considered, I would say
it would not be considered

wealthy. But this is kind of a
tourist, the tourist piece of it

is high end. When we first
started looking in 2020, you

could get a honeymoon cabin, one
bedroom, one bath for somewhere

in the three to 350 range. Now
you're looking 550 to 700 for a

honeymoon cabin.

Davina Frederick: The

Unknown: cabins that would sell
for 750 in 2020 are now 1.5

million.

Davina Frederick: Yeah, it's a
big jump. It's a big jump. So

where are you now? Do you have
to have three? How many do you

have there? I know you have a
third property, please.

Unknown: Yeah, right now we have
two and then we have two more

that are under construction. So
I'm hoping it for free, it's

don't continue to go up or we're
going to have a problem because

we can't walk in those rates
until you're getting pretty

close to it being completed. And
if they were both specs, so we

weren't doing construction loans
or anything, we just put down a

down payment and are waiting for
them to be done. During that

time rates went from our
interest rates on our last two

or two current cabins are 3%
Three and a half percent and now

they're gonna be significantly
higher for these two.

Davina Frederick: Yeah. And so
you so that's gonna be for and

broken bone and you also have a
property in Galveston, correct?

Unknown: Yeah, when we did our
1031 exchange of our first

property, I started looking
started really researching other

locations because I felt like a
we don't want to need to keep

our eggs in one basket and be we
were having a hard time finding

a property and broken bow.
Because the market was just so

hot. So I'd started you know, a
lot of the, like 30 A in Florida

or Smoky Mountains, but they've
gotten really, really cost

prohibitive and the markets are
already super high. So I was

trying to find a market that was
not quite so high that it would

be a good investment. So being
in Texas that led us to

Galveston. We'd actually almost
purchased a property there as

part of our 1031 Exchange. And
the day we were going to close a

tropical storm hit and our
contracts that we didn't have to

close to later that week. So we
didn't close it under there was

quite a bit of damage done to
the property and we panicked and

we backed out of that rut we
want to deal with paying a

$10,000 deductible on storm
damage every summer. But then

later we ended up deciding to
get a condo because the risk

seemed a lot low. We're with a
condo than with a house in terms

of storm damage. So right, we've
got that late spring, early

summer, was pretty much once it
got on the market, which took

longer than I would have liked.
But it basically has been fully

booked the whole time. Now the
problem with the condo, which we

enlarge, so we kept getting out
bid on things. And so we

realized, if we want to get a
property, we're gonna have to

pay cash. So we took a HELOC on
our primary residence to pull

cash from our house and pay cash
for the condo. But the idea

being then we would turn around
and take out a mortgage and we

paid the HELOC. When we learned
after the fact, if a building is

more than a certain percentage
investment properties, then you

can't get a conventional
mortgage on the property. So

that was that's done a little
bit less than learning the hard

way. So now it's if we want that
cash out, eventually we'll have

to sell it. But for now, we'll
just keep running it out and

have income coming in from that.
Yeah. And generally we'd like to

have mortgages on these
properties not pay cash, because

for example, if you're buying a
$500,000 property, and you only

had to put 10% down, and it's
bringing in $50,000 a year,

well, if you're making $50,000 a
year on your $50,000 investment,

that's pretty good. But if
you're making $50,000 a year on

your $500,000 investment,
because you paid cash, that's

not as good.

Davina Frederick: Yeah, yeah, it
makes a lot of sense. Now

you're, I can see where you
would be easier to get a

property manager to help you out
with broken bow because you now

you've got multiple properties
there. And then you got this

sort of low one out on
Galveston, but I assume you have

some property management company
that's helping you sort of

manage that or some some way to
help you manage that

Unknown: with our with our first
cabin, our plan was salt manage.

And we did that for almost a
year. And it wasn't that hard,

but it was time consuming. And I
finally reached the point I

realized, I'm trying to
outsource everything else in my

life. Why am I doing this
myself? Why am I the one getting

a phone call at 10 o'clock at
night because the neighbors are

noisy. So we've ended up finding
a broker, we have fantastic

property managers, they charge
super reasonable percentage is

worth every penny, they pretty
much handle at all. There's a

big crisis, they'll let us know
and ask what we want to do. But

I really don't have to worry
about those things that take

care of the maintenance, they'll
take care of, you know, hey, we

recommend a deep clean or we
recommend you power what we

powerwash the deck or whatever.
And we say yep, go for it. And

they'll just charge it to our
account. We have a property

management company and Yeah,
listen to that I'm not thrilled

with so we're gonna be looking
at you know, may look to switch

there, but I think we're spoiled
by our fantastic one and broken

bow. Some short term rental
areas, the property management

fees are very high. We had
looked at, you know, we'd love

to have a place in a ski area.
And Colorado is way overpriced.

You can't make money really,
unless you're paying cash. But

so we looked in New Mexico, and
property managers are 35 to 40%.

Davina Frederick: We can't

Unknown: do that you're not
going to be a prophet. Yeah.

Davina Frederick: What so what
give give an idea of a good

percentage for property
management.

Unknown: So our property, our
Broken Bow percentage is 18%.

And then our I think in
Garrison, it's 23%. The

Galveston company had sort of a
sliding scale, if you had a more

expensive property, your
percentage was lower.

Davina Frederick: No
Interesting. Interesting,

because they make more dollar
wise. Yeah, right. What kinds of

what mistakes do you think
you've made along the way? If

you had to do over you would do
different besides, I would have

bought up a whole lot of
property and broke.

Unknown: I would have started
earlier. Yes, for sure. You

know, I do kind of regret
selling the first cabin just

because it was a fantastic
cabin, and we loved it and I

miss it. But from an investment
perspective, it was absolutely

the right decision to make. I
would have gotten a property

manager sooner. I did drop some
expensive balls when I was

property managing it myself. We
we had a couple issues where

there were double bookings
because of some mistakes that I

had made with the software. And
then we're trying to frantically

find other cabins to put people
in and paying out of pocket to

put people up and that was the
trigger that led to hiring a

management company was I right?

Davina Frederick: It would be a
lot of work. I think that's

there will be a lot of work in
managing short term rental

because you're if people were on
vacation, and people are on

vacation, especially if they're
paying a lot of money. Need for

something, they want things to
be the way they want them. And

so it's a little bit more high
maintenance situation, as

opposed to long term renter,
they're just like whatever are

coming and go, you know, long
term renters, you know, the

house is flooded, and you need
to come fix this sort of air

conditioner brachii. But with
short term, it's, you know,

stuff like you said, the
neighbors make a noise, well, I

can't fix that, or those kinds
of things. So they can't find

something when they get there.
So there's always a sort of a

little nitpicky phone calls that
I imagined we'd get on your

nerves so bad, just constantly
people sort of calling you to

fuss about something that your
your hours away, you get to

think about,

Unknown: yeah, and there's a lot
more wear and tear on short term

rental than there is on long
term rentals. So having somebody

who may even if you're self
managing from far away, you have

people on the ground there,
because you have cleaners, you

have maintenance people, you
have to have the contacts, you

got the security guy, he's gonna
go over and yell at the

neighbors. But I'm having a
property management company

that's checking on the
maintenance, making sure your

air filters are changed out when
they need to be doing all the

things that have to be done more
regularly than a long term

rental, or your personal house,
which you take really good care

of. I found it to be worth every
penny for where I am in life.

Now we know we have friends who
aren't in the same financial

position we are and it's a
stretch to buy a cabin, but they

did it because it's a good
investment. And they need to get

every penny they can out of that
property. So they self manage.

And it's certainly doable,
especially if you had somebody

that worked part time or a stay
at home parent or somebody who's

retired somebody who isn't
working, right, isn't running a

law firm on the side, you know,
at the same time, then it's

certainly manageable. You just
have to make the right

connections and get those
contacts.

Davina Frederick: Well, yeah.
And if you turn it into, you

know, I know, there are a lot of
people who turn it into their

sort of full time business. And
they might go a little further

with sort of managing them
themselves. If that's what they

do. They've got multiple
properties, and they're managing

them all. But if you're looking
at sort of growing wealth, and

it goes back to what you and I
talked about all the time with

law firms is you you're really,
you're not really wealthy, and

as long as you're tied to the
day to day of the thing. And so

it's the same thing with any
investment that you make. You're

not really wealthy, if you're
tied to it day to day, and

you've got to be present,
because true wealth is time,

time freedom, and the money to
enjoy with that time, you know,

so what, what, what kind of,
what do you anticipate will

happen? Yeah, there's a lot of
discussion right now about the

real estate market, we already
see home prices coming down for

sellers. In Florida, we still
have really high rent, and

property values. I mean,
everybody's getting their

property assessments right now.
And you're seeing huge gains on

your property assessment. And so
there are different opinions

from people saying some people
say, Yeah, we're not going to

this will never fall like it did
in 2008. And then other people

are going, wait, wait, it's
common, you know, but I don't

personally don't think it will
ever I don't think I think there

will be a little bit of a price
drop as things sort of

normalize, because of the
pandemic. And, you know, all of

that. But I don't think we're
going to drop back down to where

people are going to lose
tremendous value in their house

to the point where, you know,
they're upside down. What do you

think?

Unknown: Well, I'm not actively
trying to buy any properties

right now, because I do think
the market is high, it has

already started to come down, I
think it will soften a little

bit more, but because of when I
bought, even if the market

softens, I'm never going to not
be able to pay that mortgage,

I'm never not going to be able
to be turning a profit. My

profit won't be as big as it was
in 2020. But that's okay. And I

think it will be a good
consistent long term investment,

I probably won't hold them on,
hold them forever, because

eventually, you know, people
like new and flashy and you get

to a point where either you're
gonna have to renovate or

something to keep up. So I like
the climbing the property

ladder, hold something for a few
years, flip it into something

else or flipping into two other
properties. I don't want to put

all my eggs in one basket,
they're mostly all in one basket

right now. So, you know, finding
other opportunities, try

connecting with, you know, a
broker Bo or have connections

with realtors that can get
things before they ever hit the

market from builders. And so
that's how we've made a lot of

money by getting things that
never hit MLS. So connecting

with realtors in other markets
where we'd like to be a But

trying to remember, it's about
the investment. It's not about a

place for our family to go, I
think people get hung up on, oh,

I want this house on the beach,
because I'm going to take my

kids there, and it's going to be
all special and fun. If you want

that, that's great. I want to
travel the world and go all

these different places, these
properties are about

Davina Frederick: investing.
Right, right. I think that's a

great point. Because I know that
a lot of people will think of

investing well, you know, I'll
I'll get something like I live

in Florida. And so the natural
thing for people who's like,

well, let's go buy, you know, of
each condo or whatever. And if

you can get in an area where we
there are some areas that are

not great, believe it or not in
Florida, for each vacations, and

then there are others that are
fantastic. Of course, right now,

everything is high. And but I
think people get caught up in

this idea of I'm going to have
it we're gonna go and then we're

going to lease it out when we're
not using it. And I think so

people can do that make it work.
But I think there are a couple

of drawbacks that one is that
you probably design it more for

your taste, as opposed to
designing it as a vacation

rental for other people. And for
me, my viewpoint would be well,

if it's my home. Like if it's my
if it's my vacation home, and

I've made it nice. And somebody
comes in and trashes it, I would

have more of a problem with that
than I would if it's if it's set

up for being rented out. Did you
have that when you were kind of

when the cabin was sort of
yours, you were renting it out?

Did you have that kind of
attachment, maybe you're not

like me and I have attachment to
buy, like I did have

Unknown: some attachment to that
first cabin. That's why I'm sad

still, that we got rid of it.
But you know, we would realize,

for example, Spring Break of
2021, we went skiing in

Keystone, or Winter Park. And I
realized we made more money

renting out our cabin in Broken
Bow than it cost us to go rent a

big townhouse in Winter Park. So
we were not ever going to use it

during that time. Because that's
how much money we were going to

lose by not renting it out. So
we were never going to go spend

Christmas there or Thanksgiving
because those are high dollar

Labor Day weekend, you know,
when the rate rates are high,

it's like I'm not I'm costing
myself $3,000 If I'm gonna go

spend this time and my habit and
it's not worth three, or I can

make 3000 By letting someone
else do it.

Davina Frederick: Yeah, so
really separating that out and

the emotional attachment and
saying this is a business

investment. This isn't about our
vacations, because, you know,

you you love to take vacations
in a lot of other places, and

probably rarely vacation in the
same place twice, because

there's only so many new things
to see, right. Whereas there are

certain people who want to have
a vacation home for their family

as your family grows, and they
want to go there every year and

make it a tradition and there
and that's not the same thing as

buying it for investment
purposes, that kind of thing.

Are there some right now are you
just kind of in the holding

pattern are there some you still
sort of actively looking for

communities where it might be
good, not broken bow, but

someplace else that might be
good for real estate investment.

Unknown: I'm pretty much in a
holding pattern, because all my

cash got sunk into Galveston.
And, you know, once I was having

the other two that when you know
when they're completed assuming

that everything goes through for
both of them, that's going to

eat up any other cash to make
those down payments. So it'll be

awhile to leave replenish the
coffers and start looking but

even if I were sitting on cash,
I don't know how actively I'd be

looking right now I wanna I want
to, I think the market will go

down a little bit more. We'll
wait for interest rates to level

out are back down a little bit.
And then I would jump back in

but long term the plan is going
to be to essentially flip one

into two flip two into four
build up the portfolio without

necessarily having to use a
whole lot of other cash.

Davina Frederick: Right because
the money's already there. So

you've already started Yeah,
wonderful. What what do you do

you think the well first of all,
let me ask you this. What are

you forgetting them booked? Are
you using like Airbnb? VRBO are

you doing other sorts of things
social media. I know you're big.

You're big into social media and
on Facebook a lot things like

that. Where do you think your
rentals your market is coming

from?

Unknown: So with our first one
when we self managed, I had a

family we had on VRBO we had an
Airbnb and we had a our own

bookings, direct booking site.
And I got a lot of business

because I would share about it
on Facebook and It had Facebook

page and all that. I got a ton
through VRBO. I got almost

nothing through Airbnb. But I've
heard from other people who had

the opposite experience,
especially I've

Davina Frederick: read recently,
somebody had the absolute

opposite experience. So.

Unknown: And then now with
management companies, the

management companies have their
own booking sites, but they also

push it out to VRBO. And Airbnb.
And I still have these, I'm not

very active about marketing them
now periodically, but especially

with our broken mobile cabins,
they're pretty much booked up,

if I noticed the weekend isn't
booked or, you know, holiday is

not booked. And I feel like it
should be that I might share and

you know, the local Facebook,
business groups or whatever,

Hey, you want to go to work and
bow for Thanksgiving? Or Kevin

still available? Things like
that?

Davina Frederick: What advice
would you have for somebody who

wants to start getting into this
short term rentals?

Unknown: So there's tons of
podcasts, there's and books and

ways of getting educated on it.
And you know, you certainly want

at least a minimal amount of
education for like, I'm pretty

savvy on money and investing and
all that. So I didn't need to

dive in as deep as somebody who
is not so sophisticated, but you

know, talk to other people in
your area, see where they're

investing is there a, you know,
like, in Georgia, people want,

who will invest in the Blue
Ridge Mountains or in North

Carolina, I know, there's lots
people who invest in the

mountains over there. There are
little broken bows all over the

country, that are probably close
to wherever anybody's living,

and finding what makes sense
based on where you are and where

you can get connections. There's
Facebook, there's Airbnb, and

some short term rental Facebook
groups that are generic that

have 1000s of people in them
where people share ideas and get

advice. There's Facebook groups
that are specific to me, I'm

probably in five different
broker bootcamp owners, groups,

and two different Galveston
property owners groups. So you

always can find out ideas, find
out about properties, find

cleaners, find lenders, by
realtors, all the things that

you need.

Davina Frederick: Connections. I
mean, I think that's really the

key is, like you said, it's,
it's expanding connections so

that you can learn things that
you might not learn from a book.

Because a book can tell you it
can. I mean, I think it's

important people read books, I'm
a big book reader, and listen to

podcasts. And podcasts often
will lead me to connections with

people. So the idea of Facebook
groups, that's a wonderful thing

that can come out of that is
just connecting with resources,

because you might not even know
what questions to ask. And then

you're in a group one day and
somebody asks a question, and

you're like, oh, man, I needed
to know that that was so great.

So really spending a little bit
of time, probably doing that

without just jumping right into
something and kind of figuring

out on the way down. Because
even though you said that you

you did that you were having
conversations with people before

then try and figure out where
can I best.

Unknown: And there are services
out there and some of its you

can get a certain amount for
free like air dna.com. There's

mashvisor.com is another one,
where you can find out

information about short term
rental markets in different

places. And what you know, what
does it look like in Broken Bow?

What does it look like in
Destin? Florida, wherever you're

looking at? You can see these
are what properties are going

for. It'll show you average
daily nightly rates. How many

there are so you know, is it
oversaturated? Is it? Is there

nobody here? Maybe there's a
reason?

Davina Frederick: Is there a
ban? I know in Daytona is

Daytona Beach is their
government over there, Man they

wanted they got rid of spring
break. They don't want them.

They barely want the bikers. And
now they've got a ban on short

term rentals. And, and there are
whole hotels on the beach that

are just boarded up from
hurricane damage. And but they

don't, they've banned short term
rentals, because they don't want

the community the floor, you
know, the native Floridian

nature of the community to
change. And they're wanting

enough housing for people there.
And I know there are some, you

know, I was reading somebody
recently in Arizona, where

they're like, hey in Sedona,
Sedona is paying Airbnb hosts

like $10,000 to rent to local
residents for long term and

trying to incentivize people
because it is there so many

people are invested in Airbnb
over the pandemic. And, you

know, whole communities are
like, Well, how do we service

this when we can't we don't have
affordable housing for the

people who live and work here.
Right. So So you definitely need

to check. I mean, I bought
something a condo in Daytona

which is just a little, you
know, half an hour 45 minutes

from my house. I would really be
screwed when the band came

through. Because then, you know,
okay, well that didn't work out.

Unknown: So yeah, there's, and
you can usually tell a lot of

places in Colorado have
restrictions on short term

rentals. Hawaii does. And you
can usually tell if you're

looking constantly on
realtor.com. And I'm bombarded

looking at different places. And
like, oh, man, this looks like a

fantastic deal. I guarantee you
it's not short term rental

eligible, because if it were, it
wouldn't be cheap.

Davina Frederick: Right?
Somebody would already snap that

up. Right away, right? Secrets
to sort of, you know, I love

decorating and that kind of
thing. And I know you decorated

your first one. And then you
hired people to interior

designers to help you do the
others. Are there any sort of

tips on kind of like, what you
want to have or not having short

term rentals? I've certainly
stayed in some that are really

great, really cool. And then
others that are like the

Hackman? Not this is not at all
like what the picture look like.

About that? Yeah, I

Unknown: know, there's a lot of
lists circulating around at

least in the cabin owners groups
about like, these are the basics

that you should have, you should
have X number of plates per

person, and, you know, this many
bowls and all these things. And

we always like to include board
games, and you know, activities

for families to do and because
you're going to walk out in the

woods, you want some family
bonding, usually, you know, a

beach with beach house, you want
all the beach toys and the

boogie boards and things like
that people can use even though

they're and they're generally
cheap and but if they end up

missing, so be it because you
know that billion dollars. I

think a lot of people in Broken
Bow like having playsets at the

added or some sort of unique
features like arcade games

inside pool tables are big Kevin
has a shuffleboard inside.

Having an amazing views. You can
add that if it doesn't exist.

But those

Davina Frederick: are things
think about that when you're

buying a place Location,
Location still matters. You

gotta have you know, absolutely.
Yeah. And the way I heard

someone put it is that you're,
you're really selling any

experience. And that's what why
so many people look, you know,

these for Airbnb VRBO is because
they're looking for an

experience, they can't get into
a hotel. And so creating that

experience by having games
having, you know, fun things and

stuff that you use, I, you know,
we rented a mountain cabin last

year. And we got there and one
of the fireplaces was not a

working fireplace at all. And
the other one was like a down in

this really dark creepy
basement, that you didn't want

to put a diamond. And so having
that having your pictures match

your experience, I think
probably comes into a lot too,

because you get some you know,
we did not leave a good review.

There were many other little
things to that made it kind of

creepy. Do you worry about
security, or, you know, people

walking off with your stuff or
destroying your property or

anything like that? Does that
happen? I mean, does it happen

much.

Unknown: We haven't really had
any problems. When we were self

managing we had, there was a guy
in Broken Bow who he used to

work for a police department or
sheriff or someone and he does

security and he monitored
everybody get put some cameras

in their cabins and he monitors
them. And they'll even know for

your guests. If you have any
problems. You call this guy and

it'll take care of it.
Periodically in the cat owners

groups, we'll see people will
share a screenshot of somebody

that was snooping around a cabin
and or somebody who was driving

off with the outdoor TV in the
back of their truck or whatever.

But we haven't had any issues
like that. Fingers crossed.

Davina Frederick: We stayed in
one cabin where they had a hot

tub. And we're thinking oh
great, a hot tub and a video

camera up facing the hot tub. I
was like, and so they were you

know, understandably what they
they probably had experience

with, you know, things
happening, neighbors coming

moving up the rod, I don't know.
But, you know, there's a fine

line between that you're still
trying to create that experience

for your guests. But you even if
you want to have you know,

security can get a little creepy
if you've got cameras

everywhere.

Unknown: Yeah, I've seen a lot
of discussions about the do's

and don'ts of putting up cameras
where it's you know, you're

monitoring who's coming in and
going, you're not monitoring

what's happening in the bedroom.
You're not monitoring,

monitoring what's happening on
the, you know, in the hot tub,

in the bathroom, all those
things it's really just needs to

be strictly a security issue,
not a spying on the guests

issue.

Davina Frederick: Yeah, I bet
there's a lot of there's an

opportunity for lawyers probably
around the whole short term

rental market it for many, many
things. Have anything else that

you can think of before we wrap
up that would be important for

people to know if this is
something that they were wanting

to explore.

Unknown: I mean, I think it is,
I don't think I know it is hands

down the best investments that
we have ever made. And it's not

even close. You know, I spent 15
years leading up to that,

working and investing in my 401k
and, you know, brokerage

accounts. And I've made more in
the last two years investing in

real estate than I did last 15.
Investing traditionally in the

market.

Davina Frederick: Wow, wow,
that's a very powerful

statement. We'll we'll end it on
that note, then, and get that

give people something to think
about. If somebody wants to

reach out to you connect with
you. How can they do that? Maybe

they want to find out about the
Draper firm. How can they do

that?

Unknown: Sure. You go to our
website, which is www dot Draper

firm.com. And there's a option
there, you can contact me

through the website.

Davina Frederick: Awesome. Thank
you. I appreciate you coming

back and doing another episode
with me as always a delight. We

have many interesting
conversations. So this one is

another word that we've captured
for other people to listen in

on. So thanks so much for being
here. Sure. Happy to do it.

Amassing Wealth Series: Wealthy Woman Lawyer® Holly Draper Shares How She Invests in Short-Term Rentals
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