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March 17, 2025 20 mins

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Welcome to The Vacation Rental Key Podcast with T and T.    Tim Cafferty and Tiffany Edwards are here to give you the key to running a successful vacation rental management business.   Listen to their decades of experience in the short term rental business and get "Keys" to make your professional vacation rental management company the best it can be!

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UNKNOWN (00:00):
Bye.

SPEAKER_01 (00:10):
You're listening to the Vacation Rental Key with
T&T, the podcast for vacationrental managers by vacation
rental managers.
I'm Tim Cafferty, and I managetwo companies, one in Virginia
and one in North Carolina.
I'm one of the two Ts.

SPEAKER_00 (00:26):
And I'm the other T, Tiffany Edwards, born and raised
in the vacation rental business.
I help manage our familybusinesses from Key West all the
way to Kauai.

SPEAKER_01 (00:36):
In the next 30 minutes, we're going to give you
our keys to success in thevacation rental business.
Well, to use a phrase I've saidmany times before, I'm back.

(00:59):
And I think we're going to bebetter than ever.
Tiffany, welcome to the podcast.

SPEAKER_00 (01:05):
Thanks, Tim.
I'm so excited to join you.

SPEAKER_01 (01:08):
So we want this first episode to give you guys
an idea about who we are.
Those of you that don't know us,those of you that do know us,
try to keep an open mind.
And what we bring to the tablethat we think will help the key,
if you will, to vacation andrental management.

SPEAKER_00 (01:27):
Yeah, Tim, I'm so excited that we're going to be
able to talk a little bit aboutwhat all we've learned over the
past couple of years and reallybring that to listeners who may
be struggling with things orwant to learn a little bit more
about the industry.
So I'm excited for this newventure.

SPEAKER_01 (01:41):
Yeah, I think for this episode, we're going to
just ask each other somequestions to give you guys an
idea of what we think we can dofor you and what expertise we
might have.
So let me start.
What do you hope to accomplishwith this, Tiffany?

SPEAKER_00 (01:56):
I actually hope that we can bring in several
different takeaways everyepisode.
One of my favorite things is toattend conferences and to have
one or two little nuggets ofinformation that I can take back
to our operations of things Ihaven't thought of.
And usually they're so simplethat it's easy to just bring it

(02:18):
back, but I need someone else tohelp me guide that direction and
learn about the things thatworked and Hey, Sarah.
Hey, Sarah.
Hey, Sarah.

SPEAKER_01 (02:47):
Hope you're enjoying retirement out West.
We always wanted to keep it to apoint where you can listen to
the podcast on an averagecommute to work.
And that's what our goal here aswell is.
I think there's.
Bite-sized nuggets sometimes arethe best rather than the long
form, although there's nothingwrong with those who have
hour-and-a-half-long podcasts.

(03:07):
I just can't pay attention thatlong.

SPEAKER_00 (03:09):
Same, Tim.
We're equal there.

SPEAKER_01 (03:11):
Let me ask you this because you've been around a
while.
Let's talk about that.
One of the fun stories that youtold me was when you were in
college, you actually got intothe vacation rental business and
the marketing end of things withyour car.

SPEAKER_00 (03:25):
I love that we're going straight into that story,
but I actually, I started evenearlier than that in the laundry
room.
So everyone has their story ofwalking uphill both ways.
I actually worked in the laundryat seven years old.
We didn't have air conditioningthen, and we used coin
operators.
So I got to use the coins to goin, but I was only allowed to

(03:46):
use the towels.
So I started there, moved my wayup, but I went to school in
Georgia, and there's a longcommute since we're based in
Florida, and that is our breadand butter of our feeder
markets.
So my mother paid me additionalallowance each month, if you
will, if I was willing to put awww.dustinvacation.com sticker

(04:12):
on the back of my car and driveit throughout Florida and
Georgia.
So I did that for four years andwas, I like to think, essential
marketing piece for her company,which is successful now based on
that initiative.

SPEAKER_01 (04:26):
The original guerrilla marketing.
That's pretty cool.

SPEAKER_00 (04:30):
I won't tell you my age of why that URL was so
important at that time frame,but it was vital.

SPEAKER_01 (04:39):
What do you consider yourself to be an expert in the
vacation rental business?

SPEAKER_00 (04:45):
That's a great question.
And for any of the listeners whodon't know me, or some of them
that may know me, a lot ofpeople know the background that
I have in advocacy andgovernment relations, I have
always worked in the vacationrental industry in some
capacity, but also have workedon advocacy and consulting.

(05:06):
What people don't realize isthat I've been a ghost in many
of our family businesses.
We have several and I I havebeen in operations.
I've been a rental manager.
I have worked with owners.
I've worked with maintenance.
I've gone in and had to look atreservations and marketing.

(05:27):
I used to check people in forhours that, you know, check in
day, because back in the day, itwas only one at a time.
And so I've really evolved.
My favorite aspect is projectsand overseeing larger projects
and working with team on thoseprojects to success.
within our different businesses.

SPEAKER_01 (05:48):
When you look at businesses out there, vacation
rental businesses particularly,do you see a theme?
Is there a common mistake you'reseeing in what people are doing
and running their vacationbusinesses today?

SPEAKER_00 (05:59):
There's lots of common themes.
I think a lot of times, and I'llsay first and foremost, is that
we We spend too much time onfires and not enough time on
evaluating what works and whatdoesn't work.
So we purchase a lot of itemsthat we think are going to be
quick fixes, but we don'tnecessarily look back to see if
they are benefiting the businessor if our employees are trained

(06:22):
well enough to use it or they'reutilizing all of the capacities.
I think we move away from thebasics and a lot of components.
I think we also are really badat self-promotion.
We don't necessarily tell ourowners all of the things that
we're doing good or bad how manytimes we're in a unit how many
times we take money off oroffset or go above and beyond

(06:46):
for the guests and i thinkthat's something that people
need to take the time to sit andreally evaluate but it's more so
of everyone kind of leading byfire as opposed to measuring
three times and then cutting sotim Starting back off with a new
podcast, what are you mostexcited about to share with our

(07:08):
new listeners and your formerlisteners in this new venture?
I

SPEAKER_01 (07:13):
feel like there's unfinished business, Tiffany,
which is why I'm back.
And again, as I said previously,Sarah is like my sister and love
her to death and still talk toher quite a lot.
And there was that vibe that wehave.
I think you and I share asimilar vibe.

(07:34):
I want to have fun.
Certainly, I have enough goingon.
I'm not going to do somethingthat isn't fun, so I want to
have fun.
I want to also touch thosepeople.
One of the things that was mostheartwarming to me is to go to a
conference and have someone,frankly, that I didn't know.

(07:54):
come up to me and say, I feellike I know you because I've
listened to you so often, and Ireally appreciate what you're
doing.
And those moments came prettyoften, and I really enjoyed
those interactions I had withpeople.
I think the latest one was whenI was at the Darm Conference.
I had two young ladies come upto me, and we took a selfie, and

(08:14):
they were telling me about theepisodes they liked and how they
had changed their businessbecause of some of the insights
that Sarah and I had given them.
That is really a great feeling.
And I feel like I'm giving back.
I also feel like I'm at a pointin life where not only am I
trying to run successfulbusinesses, but I think I can

(08:35):
help others.
And that's what this industrywas really built on going back
to decades ago.
When you go to the conferences,you would share.
And if you're doing somethingreally cool that's helping your
company, you wouldn't mindtelling people.
four or five or 10 people aboutit.
And in turn, they'd tell youwhat they were doing that you

(08:56):
could take back home, back toyour point about the little
nuggets.
And so that's what I'm reallyexcited about.

SPEAKER_00 (09:02):
Well, and you've been in the business for so long
and held so many roles.
What is your absolute favoriterole and part of the business?

SPEAKER_01 (09:12):
Boy, I really enjoy the employee side of things.
I know I'm

SPEAKER_00 (09:17):
Oh, that's

SPEAKER_01 (09:23):
my least favorite.
That is really energetic.
I'm actually in the process ofhiring a key employee right now.

(09:46):
And it's exciting for me to talkto these applicants about the
culture that we have here.
We've won awards nationallyabout being best places to work.
We've won awards from ourproductivity.
But it's really all about thepeople that are here and the
vibe we have.
And so that's, as I say, when Iwalk out my door and my
assistant asks me where I'mgoing, I'm going to do my

(10:08):
rounds.
I go and darken every door everyday, whether they like it or
not, to see how they're doingand what I can do to help them.
And people who have listened tosome of my podcasts in the past
understand that I'm really bigon goal setting.
And I think that that's thething that really gives me just
great happiness.

SPEAKER_00 (10:27):
I love that.
And that's exactly what I'm notgood at.
But it's so important to buildthat culture.
And I think that that speaks toyour point.
Overall, what the industry is,is celebrating each other,
building each other up.
Years ago, there didn't seem tobe much growth in this industry.
You stayed in one position, butnow there's so much personal

(10:50):
growth.
There's so much education aroundthis industry.
And you've really seen theevolution of that, but obviously
curated a culture within yourbusinesses to take hold of that.

SPEAKER_01 (11:01):
Yeah.
I've worked for other people andworked for other companies.
And when I was in my lastposition before I started this
company, which believe it ornot, we are celebrating our 20th
anniversary this year, which ishard for me to fathom.

SPEAKER_00 (11:15):
Have you planned a party?

SPEAKER_01 (11:16):
We're going to have a party.
It's not quite all together, butyeah, we're going to have it.
But one of the things I rememberwas My last position, putting
away half my paycheck so I couldstart this new venture.
And I remember saying to myselfthat I didn't have to do things
the way others did it.
And I'm going to want to dothings the way I want to do it.

(11:37):
And it needs to be fun.
It's worked out really well.
So do follow your passion.
Success does come.

SPEAKER_00 (11:44):
That's a good point.
That's one of the other thingswe definitely want to encourage
is following what that passionis.
And if you are someone who'slistening to this right now and
you're in that role, you know,Tim has successfully done it of
working for someone else,starting something.
And, you know, hopefully a lotof the information that he or I

(12:04):
bring can help potentially makethat transition for you.

SPEAKER_01 (12:09):
One of the things you mentioned earlier was your
love of conferences as much asanything is the camaraderie, but
that's going to be something wereally focus on in this podcast
as well.
We're going to see if we can getsome different angles and some
maybe different conferences thatmaybe you haven't attended out
there before and bring thosetidbits back to you.
Talk to me about your approachto that, Tiffany.

SPEAKER_00 (12:31):
I think it's the cheapest way that people can
essentially attend a conferenceby maybe listening in.
You know, again, my husband andI have always attended
conferences.
I always feel, and you've saidthis before on your previous
podcast, but you should walkaway with something that at

(12:53):
least provides for the financialinvestment that you put in to
attend.
And I think looking at itdifferently and what Tim and I
have talked about for thispodcast is the vacation rental
business is so much more a partof the tourism sector now.
There's so much integration now.

(13:13):
And I think looking at not justwhat is vacation rental
specific, but overallholistically, what all is going
on with the tourism industry andnow how different stakeholders
look at vacation rentals and howare they integrating and how are
they marketing and how are theybringing considerations of our
industry into what theirbranding and strategic planning

(13:37):
and so that's i think reallyimportant for us to look at at a
conference level to see howother players are talking about
us

SPEAKER_01 (13:45):
Love that.
I also find so many new peoplecoming into the industry that
it's not terrible to repeat someof the stuff that's tried and
true.
And also the other thing I thinkof when I meet the new people
who are coming in, and maybe oneof you listeners thinking right
now, they're so smart.

(14:06):
Golly, there are some reallybright people in this industry
now, and I just can't wait to goout there and talk to them.

SPEAKER_00 (14:13):
Yeah.
And Tim, that's a really goodpoint because sometimes it's
great to attend a conference orto listen to these things to
just say, oh, yeah, I do thatand build up a little bit of
validity and confidence of whatyou're doing in your own
business.

SPEAKER_01 (14:28):
Yes.
Looking forward to the nextopportunity coming up in a few
weeks in Savannah.
So I hope to see some of youfolks out there and let us know
what you think of the podcast.
So a couple of housekeepingthings.
We will come to you every twoweeks on Monday.
is our plan, 30 minutes or so.
Don't hold me to that exactly.
And it will be content focused.

(14:51):
We will have a guest every nowand then, but Tiffany has
challenged me.
She says, well, I would like tohave guests who are keynote
worthy.
Explain that to me.

SPEAKER_00 (15:00):
So, you know, again, going back into the conference
is if you have someone whospeaks English, And they, at the
general session or a closingsession, to me, they're a
keynote speaker.
It's who you line up to listento.
And so I think that when we'vetalked before, it's very
strategic of who those keynoteindividuals would be.

(15:23):
So you don't necessarily hearthem quite often, but when you
do, it's very targeted whatthey're bringing to the table.
And so we are going to challengeourselves to bring those
individuals to this podcast.

SPEAKER_01 (15:38):
And it's not easy.
I can tell you from experience,you got to jump through a lot of
hoops to get these peoplesometimes to commit to 30
minutes on a Zoom call, butwe're going to do it by God for
you, the listener.

SPEAKER_00 (15:50):
Well, now it's out there, so we have to do it.

SPEAKER_01 (15:53):
Yeah.
And so one of the things that Iwould like to continue from our
previous podcast that we'llrename is when we do have a
guest on, I'd like to do quickdraw.
Quick questions to find out moreabout those people.
So, Tiffany, I've got a fewquick draw questions for you.

SPEAKER_00 (16:15):
Oh boy, I wasn't prepared for

SPEAKER_01 (16:17):
this.
You don't have to be.
That's the whole thing aboutquick draw.
These are off-the-wall questionsto let you know more about who
we're talking to.
So, What's your favorite movie?

SPEAKER_00 (16:28):
Sixteen Candles.

SPEAKER_01 (16:30):
Really?

SPEAKER_00 (16:30):
It's the first thing that came to mind.
Okay.

SPEAKER_01 (16:36):
How about a skill or talent that you do not currently
possess you would like to have?
Oh,

SPEAKER_00 (16:43):
gosh.
It's more of a superpower thatfirst comes to mind, which would
be stopping time.
But I don't think that I'mcapable of that.
So I would say running faster.

UNKNOWN (16:55):
Okay.

SPEAKER_01 (16:56):
Okay.
So are you a runner?

SPEAKER_00 (16:58):
I used to be.
My hips and my knees don't quitework like they used to.

SPEAKER_01 (17:02):
I'm with you.

SPEAKER_00 (17:03):
I do teach spin.
That's

SPEAKER_01 (17:06):
better.
Better on the knees,

SPEAKER_00 (17:07):
right?
Better on the knees.

SPEAKER_01 (17:08):
Yeah.
Yeah, I'm with you.
21 marathons did me in.
Yeah.
My knees hurting just thinkingabout it.
How about your favorite place tovacation?

SPEAKER_00 (17:19):
Oh, yeah.
favorite place to vacation isdifficult because i love all of
our locations so i won't pickanything domestic i will say
favorite trip moment last yearwe did a truffle hunt in italy
with my children and i would saythat that moment in that place
at that time was my favoritethat's

SPEAKER_01 (17:40):
cool all right and my last one this is a really
important one make sure youthink about

SPEAKER_00 (17:44):
it

SPEAKER_01 (17:46):
Apple phone or Android?

SPEAKER_00 (17:49):
Oh, Apple phone.
Oh my God.
Gosh, did we not, we didn't gothrough this?
Have I not seen your color textblock?
We need to reevaluate.

SPEAKER_01 (17:59):
Oh

SPEAKER_00 (18:01):
gee.
No, all, every computer,everything we've got is all Mac.

SPEAKER_01 (18:05):
Yes.
I'm hanging on though.

SPEAKER_00 (18:09):
I appreciate your loyalty.
and support and you have betterpictures so

SPEAKER_01 (18:18):
well yeah okay so that's uh we're 10 of quick draw
okay so what else you want tocover these people are getting
tired of us i think they want usto go and get some content on i

SPEAKER_00 (18:27):
think the next one if we could tease what our next
podcast would be about it's onethat we've talked about that we
think will be really helpful toexplain kind of our backgrounds
as well but tim if you want toshare a little bit about what
we've what our next podcast willbe?
No.

SPEAKER_01 (18:44):
Never.
No.
Actually, that's going to be thepodcast.
The no's and never's in thevacation rental industry.
Never again's or things not todo.
Does that sum it up?

SPEAKER_00 (18:58):
Is that teasing enough?
It's our full humility of wherewe've ever gone wrong.
And we're going to share it, andit'll be a bit of a therapy
session, but we hope that it'llbring you the opportunity not to
make the same mistakes.

SPEAKER_01 (19:11):
Right.
Okay, so you've already found uson the podcast app that you're
probably listening to at thismoment.
You can find us on Spotify.
You can find us on Pandora, oniHeart, on Apple Podcasts,
obviously.
You can also visit us on ourbrand new website,
thevacationpodcast.

(19:32):
Rental key, all spelled out,with T and T.
Not the ampersand.
You have to spell out and.
So the vacation rental key withT and T.
That's pretty much what we gotfor you today.
One episode down.
How many more to go?
Good job, Tiff.

SPEAKER_00 (19:51):
Thanks, Tim.
We're excited.
Thanks for listening.

SPEAKER_01 (19:55):
So long, everybody.
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