Latest / Host Planet: Airbnb, Holiday Let, and Vacation Rental Insights / From Corporate Finance to 16 STRs: How Allison Became The Crafty Co-Host

Transcript

From Corporate Finance to 16 STRs: How Allison Became The Crafty Co-Host · Host Planet: Airbnb, Holiday Let, and Vacation Rental Insights

0:00
Welcome to the House Planet Playbook, your go to guide for
0:03
mastering short term rentals. In this special series, we're
0:07
sitting down with 30 of the world's top property managers to
0:10
uncover what really drives success in the vacation rental
0:14
industry. You'll hear their stories, learn
0:16
the key lessons they've picked up along the way, and discover
0:19
the game changing tech they use to deliver five star guest
0:23
experiences. If you're serious about growing
0:26
your STR business, you're in the right place.
0:29
We've also developed a an e-book featuring the stories of every
0:32
manager in this series and you can download it for free.
0:36
Head to Houseplanet dot Club to find out more.
0:39
In today's episode, we're chatting to Alison Craft from
0:41
Tampa in Florida. Stand by for a deep dive into
0:45
turning a side hustle into your full time job, delivering family
0:49
friendly stays and the power of AI guest comms.
0:58
This special series is brought to you by Hostplanet and
1:01
Hospitable, the smart AI powered property management software
1:05
trusted by hosts worldwide. With Hospitable, you can
1:09
automate guest messaging, sync calendars across platforms and
1:13
manage your rentals with ease, all from one powerful, easy to
1:17
use platform. If you're keen to run your short
1:20
term rental on autopilot, try Hospitable today.
1:24
Visit hospitable.com/houseplanet to see how the platform can save
1:29
you time, reduce stress, and maximize your earnings.
1:33
Allison, thank you for being part of the Host Planet
1:35
Playbook. Let's start with you.
1:37
What's the name of your company, Where are you located, and how
1:41
many rentals do you manage? Yeah.
1:43
So I'm Allison. I'm located in the Tampa Bay,
1:47
Florida area. I'm currently managing 16
1:51
listings. The name of my company is Crafty
1:54
hosting or the Crafty Co host. You can search me in those two
1:59
different terms. But but yeah, so I what was I
2:04
going to say? Yeah, it's been a lot of fun.
2:06
Let's just say that it's it's a lot.
2:09
Fantastic the crafty Co host. I'm the crafty Co host.
2:12
So how did you get started in short term rentals?
2:16
Yeah, so I actually got started back in, well, June of 23 is
2:22
when the idea sparked and and I found this individual, this
2:28
content creator who is all about Airbnb data.
2:32
And so anyway, I found Airbnb through a thumbnail on YouTube
2:36
and I kind of went down a rabbit hole.
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And you know, that was back in like May, June of 2023 and then
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2024 or I'm sorry, December of 23 is when I bought my first
2:50
house, my first rental. And then February of 24 is when
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it went into, you know, I started renting the guests and
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went live and then I started my Co hosting business in June of
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2024. So everything has happened very,
3:07
very fast. And that's that's what I've
3:09
learned. This industry is just you.
3:11
You move really fast. Yeah, very fast indeed.
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So we're now just, well, it's, it's only a year really that
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you've been hosting and and you're already up to 16.
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So tell her, tell her. How did you get up to 16 so
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quickly? I know it is kind of crazy.
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So I actually joined like this mastermind, you know, like this
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coaching for Co hosting and building out your business.
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And you know the, the guy that that has been coaching me, his
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name's Austin Palacios. And so I got on his mastermind
3:43
and learned his sale scripts. And and so anyway, with me
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living in a vacation market, it was actually, I shouldn't say it
3:49
was easy, but you know, it, it wasn't too hard to, to get
3:57
clients and because there's just a lot of opportunity here.
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So when I first started, I, you know, I spent some money on
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marketing dollars. Obviously I created my business,
4:08
created a website, you know, I looked legit and also too, I had
4:13
my own rental that I was self managing and operating and I was
4:16
doing all of that out of state. So I I basically just immersed
4:20
myself in this industry and really just learned as much as I
4:25
could. Like any minute of the day I'm
4:27
listening to a podcast, listen throwing up YouTube something
4:31
and and I'm always learning about hosting tips and things
4:35
like that. So it's nonstop and I basically
4:38
he got obsessed, let's just say that.
4:40
So what did you do before? Oh, so I was in corporate
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finance. So I, so I worked in corporate
4:47
finance for like 10 years and, and anyway, so after having my
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first kid, obviously, you know, you go through the whole thing,
4:55
the maternity leave and then you go back to work.
4:58
And so it was all fine and dandy.
5:00
I was working a cubicle job. And like I said, I have been at
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that job for 10 years doing basically the same kind of role
5:08
in the same cubicle. And so anyway, and then once I
5:11
had the, my second boy is when my mindset started to shift a
5:16
little in terms of, you know, the whole postpartum, going back
5:21
to work, putting my infant in daycare.
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I don't know, things started to, to change in my mind and I'm
5:28
like, I don't know if I want to keep doing this.
5:30
I want to have more time, freedom.
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And that's when I went down that rabbit hole of, OK, how, how can
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I, how can I achieve this while still making an income and
5:40
fulfilling my, you know, need to work because I love working,
5:46
right? But I just didn't love driving
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to a cubicle and kind of being handcuffed because it, it was
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just that like it was really difficult trying to find time to
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even go to doctor's appointments and just finding time off.
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And so anyway, that's, that's that was the whole shift there.
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And I ended up quitting my W2 and going full in on this
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business back in December. So I've only been like full time
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on my, you know, crafting Co host for six months.
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So because I quit, you know I put in my 2 weeks in December
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and it was right before the holiday break is when I said
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goodbye. Amazing.
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And and is the change paying off?
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Are you wishing you'd have done this sooner?
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Yeah, exactly. I think the timing was just
6:34
right to be honest with you, because I, I held on to my W2 as
6:39
long as I could because, you know, I'm a very conservative
6:42
person. It was, I was scared to, to
6:46
quit, to be honest, because I had a nice 401K, the 401K match,
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you know, I had all the things and, and you know, it was very
6:55
nerve wracking to, to say goodbye to that.
6:59
And so anyway, Long story short, once I hit I would say 50 to 60%
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of my cash flow like because I was working in the management
7:08
business on the side as like my side hustle.
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So once I hit that like 60% and I had stuff in the pipeline and
7:16
my sales like I knew that clients wanted to work with me
7:19
and I was going to be onboarding certain listings after the new
7:22
year. I knew that I was like, all
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right, this is time to jump and just go full in on this
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business. You're all in.
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Fantastic. No, no, no looking back now.
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OK. So, So what helps your brand,
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you know your management style, what helps you to stand out
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among the competition? Yeah, so, well, my profile
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picture says it all like it's a picture of my family, right?
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I'm very family oriented and focused.
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I know what you know these moms are going through to plan for
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their vacation, especially if they're going out of state,
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getting on a plane, etcetera. Do you have a pack and play?
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Do you have a high chair? Are there baby gates?
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Is there a door alarm because you have a pool?
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You know, we don't want our little ones sneaking out.
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You know, we want to be, you know, we want a safe space and
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we want fast, fast Wi-Fi. You know, we want all the things
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in the comfort, the cleanliness, everything.
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So it's just thinking about those things catering to that
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type of guest. I know I'm going to win every
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time. And so, and another thing too,
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like that's for like my guest branding is family oriented and
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in terms of my clients, multiple clients have told me it's like
8:29
also we love working with you because you care.
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So it's like that was like my barrier to entry is just caring.
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And I have that boutique style, you know, because that that's
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how I sold them. I was like, you know, you're
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going to be dealing with me. You're not dealing with a a
8:42
massive management company and you know you're going to get
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that one-on-one experience with me.
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And, and anyway, I think they really like that and they knew
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that I'm just a authentic, trustworthy person.
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So, so those are the two kind of branding that I have so.
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So how do you now keep your owners happy?
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What would be your top tips for keeping owners in the picture
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and and happy with your service? Yeah.
9:10
So I mean that's, that's such a great question and it's really
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just more so just communication and setting up expectations from
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the get go because that was the mistake that I made in the very
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beginning is setting clear expectations.
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You know, because I I I do like having that open line of
9:29
communication that you have my cell phone.
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It's just when certain clients may, I don't know, I, I don't
9:35
want to use that word, abuse it where they're sending, sending
9:39
me texts non-stop voice memos, calling me and just like
9:43
micromanaging. So that's where like, OK,
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setting expectations like you're handing your property over to
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me. You're going to need to, to
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trust me in this. And so anyway, just just having
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that, you know that from from the beginning and I'm trying to
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think of what else like, yeah, just like that open line of
10:04
communication that that that's what makes them happy.
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And then and then just just knowing that I'm communicating
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to the guests like immediately and, and getting those five
10:14
stars. And because once they see those
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five stars coming in, then they they are very happy with that.
10:21
Absolutely, yeah. We all want those five star
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reviews. So in in terms of the guests
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then what are your top tips for delivering a great guest
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experience? Yeah, that's a great question
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too. And I know that you recently
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had, you know, the host buddy AIJ on on here not too long ago.
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And I am a big fan of his software and I feel like his
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system has like I integrated his software into my business, OK.
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And I, you know, I did all the smart templates, the upselling,
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all of it. And it, I feel like that's kind
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of transform the guest experience in terms of
11:00
communication because I was just kind of doing the basic stuff as
11:04
a host, you know, sending that automatic thanks for booking.
11:08
And then quiet, like just silence because I, I listen to
11:12
this pot or I don't know if it was a podcast or some kind of
11:15
interview with a couple of ladies from Touchstay and they
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were just like awkward silence is just that it's awkward.
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So don't make your guest experience awkward.
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Like continue to communicate with them.
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Like give them value, meaning give them ideas of, you know,
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booking experiences, you know, and, and like booking a charter
11:41
or booking a fishing trip. Like, like give them the the
11:44
tools and and everything like that to, you know, to to enhance
11:49
their stay. Any more tips for delivering a
11:53
great guest experience? Yes, so of course it's the the
11:57
upfront communication, you know, giving them the value of what to
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do in your area. Like you're like, this is your
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market, like you need to be the expert and tell them the local
12:08
spots, you know, where to eat, what to do, kind of give them
12:12
their that local insider information.
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That's huge value there. And then obviously the other
12:17
value is kind of what I alluded to before is giving your guests
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what they're expecting. The the safety, the comfort, the
12:28
cleanliness, those bare minimum essentials is will will help
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with the guest experience as well.
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And then obviously, like, I don't know, like if you look at
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my listings that I have and that I'm managing, the biggest thing
12:41
are the amenities, you know, the playground, the pools, mini
12:44
golf, the hot tubs that you name it, you know, we have the
12:48
amenities for it. Not every listing that I have
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has that. I mean, I, I manage some
12:52
apartments that are perfect for, you know, your, your, your
12:55
workers or people that are coming to visit, you know, at
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the nearby hospital and things like that.
13:00
Like it's perfect for for those clientele, but I also have for
13:05
the families as the majority of my listings and those are the
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ones with the amenities just packed, just the game room and
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all the things. So that's another another thing
13:15
for the guest experience. What are the biggest challenges
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and opportunities in the market that you operate in?
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So the biggest opportunities, I mean, it's everywhere.
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I like I said, I'm in Florida. We're a vacation rental city.
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It's been, you know, Airbnb came in way, way after like the
13:37
vacation rentals have already been here.
13:38
It's been here for years and years, you know, decade, yeah,
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decades. So like there's so much
13:44
opportunity here. It's, there's a, like I said,
13:49
the, the barrier to entry is it's, it's pretty low because
13:54
there's a lot of homes that are just being mismanaged and some,
13:58
you know, maybe some frustrated owners or even, you know,
14:01
guests. So you can come in and, and, and
14:05
really give that speech of I'm a boutique style manager and I can
14:09
turn your ship around and, and really help boost your revenue
14:15
and give that, you know, that one-on-one experience instead of
14:20
just being managed by a big management company.
14:22
So and. What what are the big challenges
14:25
in Tampa? Have you got any regulation to
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deal with or or anything like that?
14:30
Oh yeah, there's definitely, there's definitely regulations
14:33
here. You want to make sure you do
14:35
your research, you know, absolutely.
14:39
There are a lot of regulations here.
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I mean, they've been around for ages and actually recently they
14:46
just became more strict in terms of licensing and certificates
14:51
and inspections and things like that.
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So, so yeah, definitely do do your research on on the Florida
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market. I'm in Tampa, Clearwater, Saint
15:01
Pete area. So those are like the areas
15:04
that, yeah, you definitely want to do a little bit of research
15:06
before you either buy or you just start managing.
15:10
I can remember going to the water years ago and I think over
15:13
20 years ago, our family came over and we stayed in Kissimmee
15:17
in, in a gorgeous like 8 bedroom villa.
15:20
So yeah, you know, the, it's been around for a long time,
15:22
hasn't it? Vacation rentals in Florida,
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very, very long time. What's been your biggest lesson
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learned since you started? I don't know, You haven't been
15:31
going that long, but what's what's something that's really
15:34
stuck out that you've maybe you'd wish you'd known at the
15:36
start? Yeah, I mean, actually it's more
15:40
so geared towards longer stays. So I actually have like this
15:45
apartment that I'm managing and I, you know, I had this what I
15:48
thought was a great guest. I mean, it was a female.
15:51
She came in and she needed a place to stay as she renovated
15:55
her home that got hit by a hurricane.
15:57
So it's like great, she's willing to pay the market rate
16:00
for our furnished apartment and it was a great revenue stream.
16:05
I'm not even going to lie. It was, it looked fantastic,
16:07
plastic on paper. And this was the first time I
16:09
ever dealt with like a a midterm or like a monthly stay.
16:14
And so this was a big lesson learned on my part.
16:18
And like I said, she checked all the boxes.
16:20
She was very, you know, very nice.
16:21
I even called her on the phone. Yeah, just like she was asking
16:25
for a couple of things. But anyway, so a month goes by,
16:29
I, I do not get a cleaning crew in there.
16:32
Big mistake. I should have had a cleaning
16:34
crew go in at least halfway through her stay to, to do a,
16:39
you know, a mid clean stay. So that was mistake number one.
16:42
I did not do that. And then, you know, the month #2
16:46
comes in and she's now asking for more time.
16:49
And I was like, that's fantastic, you know, yeah,
16:51
absolutely. We'll we will extend your stay.
16:54
So we extended her stay and then again, I should have had
16:58
somebody go and check the property.
17:00
And then so after like extending her stay, you know, I blocked
17:05
the calendar and maybe like another two weeks after I
17:08
actually got a booking, you know, for like a short term
17:11
stay, like a weekend getaway. And so, so anyway, as, as you
17:15
know, we were approaching her check out date like she was
17:20
asking for more time and I said, OK, we can do, we can do another
17:24
week, but I have another person coming in.
17:26
So you're going to have to leave on this day.
17:29
And so anyway, Long story short, you know, she she leaves and
17:34
then I go to the property and it's a disaster dog.
17:39
Basically the dog pooped and peed in the house.
17:42
It's all over the walls. She was hoarding.
17:45
There was so much it was so bad and I had to check in that day.
17:49
So that was another mistake. Never do a turnover on on when
17:54
IA midterms day, you know, And so it was a guest from excuse my
17:59
language, it was a guest from hell.
18:01
And and so anyway, I learned, I definitely learned the hard way.
18:06
I was there cleaning the walls and I was helping my cleaning
18:09
crew as best as I could. The cleaning crew wasn't done
18:12
until 8:00 PM that night, so I had to obviously apologize to
18:17
the guests. I even refunded them for that
18:19
night. They still were OK with it.
18:21
They went out for dinner. They, you know, extended their
18:23
time out on the town and then they were able to check in at
18:26
8:00 PM. But they got a free night stay
18:28
out of it anyway. So that was a big lesson
18:31
learned. Oh gosh, what an experience.
18:34
We've all had them. We've all had them,
18:36
unfortunately similar to that. Wow, good goodness, me, the dog
18:41
dog mess on the on the wall. We can deal with that.
18:43
I know, sorry it was so bad. What do you love most about
18:50
hosting? OK, so I don't know why I love
18:54
this, but it's the It's creating the systems, it's creating the
19:00
the automations. I I I don't know what it is.
19:02
I I so my property management software I use hospitable love
19:06
them. Obviously, I integrated host
19:09
buddy AI and I just integrated stay Fi and so so I know I have
19:14
stay Fi. So, you know, my guests now have
19:17
like a landing page to go to facts about the property, local
19:22
things to do in the area, experiences, and then, you know,
19:27
book again, like book direct. So, and I, I just started
19:30
working with Bruce Lee, which is how I found you guys, by the
19:32
way. So Bruce Lee created my website
19:36
train. Like I feel like my business is
19:37
literally transformed overnight. And so I have a great booking
19:41
website now or direct booking website now.
19:43
And, and so, so with all those tools is like that.
19:48
That's what keeps me up at 2:00 AM working on.
19:51
I don't know why, but that's that's what's exciting about
19:53
hosting is creating the the systems and the processes to to
20:00
have a smooth operations. So that that is my yeah, what I
20:05
love the most. Love it.
20:07
That's great. Yeah.
20:08
Setting up those processes so it's all going to be smooth.
20:10
Brilliant. And if somebody came to you,
20:12
Allison, and said, look, I'm, I'm in a full time job now and I
20:15
want to quit and I'd love to follow in your footsteps and do
20:18
what you're doing. What would your advice be to
20:20
them? Yeah.
20:22
So if you wanted to leave your W2, my advice is to hold on to
20:28
your job as long as possible until you do, until your side
20:32
hustle is making that 50 to 60% like cash flow in terms of
20:36
profit each month. And that you know that you have
20:39
sales in the pipeline that are coming up, that, that that's a
20:42
perfect opportunity to jump ship.
20:44
But you definitely want to work on that side hustle as you
20:48
currently have your main hustle and then your side hustle
20:50
becomes your main hustle. And then you can get rid of that
20:53
job and, and then go all in. Like I always say, like burn the
20:57
boats, you know? So one, once you find that fire
21:01
under you and you have listings that you're managing currently
21:06
and you are becoming more confident, that's when you just
21:10
go all in on your business. And that's what that's exactly
21:13
what it is. It's a business and so you're
21:16
quitting your 9:00 to 5:00 to to work 24/7.
21:19
I had to say it like that, but it's I created a lifestyle
21:23
around this business now. And maybe, I don't know, people
21:27
may have a different view on that.
21:30
So yeah. Yeah, I think, you know running
21:32
your own business, yes, it gives you the flexibility it.
21:36
Does. But you're not going to stop.
21:40
Don't. Don't think it's fewer hours
21:42
because it definitely isn't. It's.
21:44
Not all right then, Alison, we've got a few kind of more
21:46
quick fire questions now. So which PMS do you use?
21:50
Hospitable. Which dynamic pricing tool do
21:54
you use? The price labs pretty generic.
21:58
Price Labs, Which piece of tech couldn't you live without?
22:02
Well, I mean, this is random, but I can't live without the
22:06
electronic door locks. I don't know what it is.
22:08
So that's, I know that's, and obviously, I mean, I mentioned a
22:11
bunch of software that I use, but if I had to deal with manual
22:15
keys or physical keys, my business, it would be a pain.
22:20
But yeah, so shout out to Slage. I don't know if I'm saying that
22:24
name right, but that app, I love that app and having electronic
22:27
door code is. That's the tech I cannot live
22:29
without. Nice, great shout out there.
22:33
Ideally pets yes or no maybe. Judging by that story before,
22:37
definitely no, but I'll let you answer.
22:40
I'm going to say yes to pets still because there's, you know,
22:44
you still get those good dog owners or good pet owners,
22:48
you're going to have that, that 1% that's going to be bad.
22:51
And it's it's worth the gamble because they do bring in
22:54
additional revenue. Similar similar question hot
22:58
tubs yes or no? Yes.
23:01
Hot tubs, Absolutely. Ideally a self check in or a
23:06
personal welcome. I mean, self check in all day.
23:09
I don't know, I can go on about that.
23:11
But yeah, self check in. Ideally as well a telephone call
23:16
or an AI response. Well, as I was just talking
23:19
about host buddy, I'm all about AI right now, absolutely AI.
23:23
But I have, you know, I've listened to Mark Simpson from
23:27
Bruce Lee and you know, it's like having having that personal
23:33
touch, calling the guests after they book, that is something
23:37
that will, you know, set you apart 100%.
23:40
And what's your most memorable hosting moment?
23:45
Oh gosh, my most memorable hosting moment.
23:47
Well, oh man, obviously it was that one terrible experience.
23:53
Usually the bad ones stick with you as opposed to the good ones.
23:56
But But, yeah, just just hosting for families that, you know,
24:02
that just want to create experiences with their kids.
24:05
I mean, I'm about to do that this weekend with mine.
24:07
And that's like seeing their face, like, hey, I just booked
24:11
this place. Like check out.
24:12
Like, like, like I show them the pictures and then their reaction
24:15
of going nuts as a mom, that's, that's worth it.
24:19
So just just knowing that I'm providing that experience like
24:22
that, that's memorable, you know, to me.
24:25
Yeah. I love that shout out time then.
24:29
Is there an individual in the STR industry who's helped you
24:32
that you'd like to give a shout out to?
24:34
Oh, absolutely. So the guy that started it all
24:37
was John Bianchi. So John Bianchi, he's known as
24:40
the Airbnb dating guy. You can find him on Instagram.
24:43
He founded the the the company STR search and he was the one
24:47
that help me find my first property and that became cash
24:51
flowing. And so once I started operating
24:55
and managing my own property is when then I found this passion
24:59
of hosting and now it changed the complete trajectory of my
25:03
life. So John was a pivotal person in
25:06
in my journey. So shout out to John.
25:09
Great shout out for John there and question to finish then
25:13
ultimate goal for your business. Yeah, the ultimate goal
25:17
obviously, you know, is to grow my business, but to build out a
25:22
team because right now, you know, I I am kind of doing
25:26
everything on my own. And so so just building up,
25:31
building out the team that I can grow with sustainably.
25:35
That's the ultimate goal. And, and yeah, so and just to, I
25:40
don't know, just to leave a legacy with for my kids and, and
25:44
continue to purchase short term rentals and maybe even get into
25:47
that unique stay, you know, industry of tree houses or, or
25:53
you know, the tiny homes like on land.
25:56
Like that's something that's interesting me right now.
25:58
So I've been poking around on that.
26:01
Superb Allison, thank you so much for sharing your journey
26:05
and for being part of the House Planet Playbook.
26:08
Thank you. I appreciate it, James.
26:10
All right, that's it for today's episode.
26:11
My thanks to Allison for sharing her journey and for being part
26:15
of the Host Planet playbook. Remember, this series is brought
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to you in partnership with Hospitable, the all in one
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notch guest experience or just get some of your time back.
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And here's the good news. Host Planet Playbook listeners
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three months. Head to hospitable.com/house
26:52
Planet to claim your offer and start running your rentals on
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autopilot. For more free education for
26:59
vacation rental hosts, head to House Planet dot Club where you
27:03
can sign up for our newsletter, listen to our podcasts, and
27:06
download our suite of of ebooks. Until next time, happy hosting.