Today we’re giving you an insider's view of a rockstar manager who is running a ton of rentals and has so much valuable experience and data to share. Whether you’re managing your own property, looking to partner with a management company or simply want to learn more about how it all works behind the scenes, today’s guest, Meaghan Moylan, is the perfect person to learn from when it comes to customer satisfaction and operational excellence.

An industry leader with 8+ years of experience in the STR space, Meaghan leads a team of passionate and entrepreneurial-minded professionals at The Outpost Group, a private investment office based in Jackson Hole, Wyoming. The company's portfolio includes Outpost, Snake River Roasting Company, Terrain Landscaping and Snow Removal, O2 Cleaning, and Provisions Catering. Prior to her role with The Outpost Group, Meaghan held several leadership roles at 360 Blue, one of the largest luxury vacation rental businesses in the US. During her tenure with the company, Meaghan also assisted in the development of Key Data, a short-term rental data and benchmarking platform.

In this episode we talk about what it was like to be a reservationist at a large vacation rental company and how the property management business has evolved. She shares advice for working through rate change mistakes and fixing those inevitable errors. She explains the benefits of having laborers work for you in house versus contracting out, why it’s so important to be able to unlearn and adapt to evolving industries, how to set and evaluate KPIs for different sides of your business, what situations warrant a refund, and how to provide an exceptional customer experience. She also provides insight into what she’s learned post-COVID, what the current landscape is for vacation rental management, how to communicate effectively and honestly with the property owners, and what to think through if you’re thinking about bringing on a property manager.

Resources:

• LinkedIn: Meaghan Moylan 
• Website: outpostjh.com
• #STRShareSunday: @sunsetinnvt

Thanks for Visiting is produced by Crate Media.

Mentioned in this episode:

Hosting Business Mastery Method | Join us for our live, free, host masterclass and learn how to OWN your digital real estate!

HBMM | Sign up today at hostmasterclass.com.

Breezeway | Go to breezeway.io/tfv to claim your free implementation when you start a Breezeway account.

Minoan | Minoan helps short-term rentals and boutique hotels enhance their appeal with their customizable, curated retail platform.

Minoan | Visit MinoanExperience.com and tell them TFV sent you!

SEGMENT GAP

Hey, welcome back for another great episode.

My name is Sarah Karakaian.

I am Annette Grant, and together we are--

Thanks for Visiting.

Let's kick this episode like we do every week, and that is sharing

one of you, our amazing listeners and viewers by sharing one of your

short-term rentals here on the pod.

Annette, who are we sharing this week?

This week we are sharing @sunsetinnvt.

Again, that's Sunset Inn VT.

I'm going to give a little bio.

The hosts are Sophia and Ashley, and this is a 1787 inn.

Yes, I said that, 1700s.

And these two ladies, they are the proud owners on the

Sunset Inn and the Ginny House.

They are best friends from high school.

Love it.

They went to college together in Boston University, and then they shared a one

bedroom in New York City for a while.

They both worked for fashion brands during college.

So just think about that and then mix that with this historic inn, you'll

want to do a deep dive on their photos because the design of the rooms is lovely.

And one thing that I just cannot stop staring at in the inn is the wood beams.

Man, they are incredible.

And I don't know if they had to restore them, but it is stunning.

Check it out.

The detail, the stuff that has been left behind, and then the new additions

are just woven with the utmost care.

Um, and yeah, just stunning.

I love it.

They're in business now and they are biz besties, again, and just two women

rocking it with the Sunset Inn VT.

Please give them some love.

Check out the rooms.

Check out all of the, um, renovations that they've done, and it is stunning.

And the kitchen, the kitchen cabinets, loving the green that

they've got going on there.

So if you're in Vermont, Proctorville, specifically, check them out.

So Sophia and Ashley from the Sunset Inn, thank you for using the hashtag, Sarah.

#STRShareSunday for those of you who haven't used it yet.

And also they have an exterior picture of the home, and they do

the history of, um, a captain of the Revolutionary War lived in this home.

They have a story here on who the previous owners were, so check it out.

All right, Sarah, let's get on to the show.

All right.

Today we're to get down to business.

We, Annette and I, always preach about treating your short-term

rentals like the business it is.

And so what better way to give you an insider's view of a rockstar manager

who is running a ton of rentals, really relies on key performance

indicators to make that next move.

Relies on historicals.

Relies on their gut instincts for what to do next.

Today we have Meaghan Moylan, is a vacation rental

manager from Destin, Florida.

After leaving her leadership position of six years with 360 Blue, she moved

to Jackson Hole, Wyoming, where she oversees a portfolio of businesses.

We'll get into that because I also think that's brilliant the way this

property management company operates, including Outpost vacation rentals.

Meaghan, welcome to the show.

Thank you so much for having me and for the intro.

I'm so excited to be here.

Let's do it.

So we met Meaghan at, we were on a virtual event together.

And Meaghan, so you have moved from Dustin, and you were not really on

the-- you were working with an online business; is that correct, in Dustin?

So I was working at 360, which was a vacation rental company

there, and then I was part of the creation and initial build out of

KeyData, which is a SaaS company.

That's where I was getting, the behind the scenes.

Okay.

Awesome.

So why'd we make this move, from Florida to Wyoming?

That's a big move.

Yeah, it was not intentional.

It happened accidentally for sure.

I decided to leave 360 after six years, and I had grown up there,

so I started right out of college.

Had never had a 9-5 in my life, ever.

Didn't know what I wanted to do.

I was planning to move to Thailand to teach English, and, um,

took a job as a reservationist.

I was going to say, how'd you get hooked?

Okay.

Yeah, I was like, I'll do it for six months.

And my boss at the time was leading the reservations team and revenue, so she was

setting all the rates for every single property, and at that time we had 225.

So she was setting all the rates for every property, communicating with the

owners when they were worried about bookings, and I was so fascinated by it.

So I went home and watched YouTube videos on how to do Excel, how to use Excel, for

the entire weekend because I had no idea other than what I had learned in college.

And I came to her office the Monday after and was like, I

really want to help you out.

What can I do?

I want to learn everything you do.

So she was like, okay, and started giving me some tasks, and eventually,

I took on that role of the director of sales and revenue six months later.

Can you tell our audience though, because a lot of our audiences,

they're owner-operators, so they don't even have contact really with big

vacation rental companies, so what was the role of the reservationist there?

And you said you had 225 homes in the portfolio?

We did.

So it was really I sat at a cube, um, with a headset on, and every time the phone

rang, um, I would answer it because our call volume was so high, and obviously,

it was seasonally, so depending on what time of year we were in, call volume

would really start to increase, and you would just sit at your desk, and our KPIs

then, so our key performance indicator, was what we were really monitored on

how many phone calls we were answering.

Making sure that we were at our desk, answering those phone calls when

they were coming in so we could have the best guest experience possible

and converting those reservations.

So I would get leads, and pretty much the leads, they would all come in,

or the majority of them would come in just someone seeing our listing,

whether it be on the website or on Vrbo.

It was Vrbo back then, Vrbo.

This is the first time I've ever been able to say back then in my life.

But this was very back then.

This is 2015, um, an Airbnb.

Can you share with us, because I think, I mean, there's probably

so many listeners are like, what?

Talking to the guests, interact on our phones.

So can you enlighten us, what are these questions?

Even though the person has seen the listing online, what do you feel

like those top three questions, as a reservationist, you were still

getting answered after people had already reviewed the listing online?

Oh my gosh.

The first one, no matter what, it doesn't matter if the calendar was

open, was, is this property available?

Every single time.

Okay.

Um, so that was number one.

All right.

And at this time, we really liked that the guest was calling in

because having that personal touch, and getting one of us on the phone,

I think there were six, seven of us answering phones at this point.

We wanted to get them on the phone so we can convert that sale.

And we were incentivized that way.

And so it was helpful for us as a team because we knew if we were converting

them, we were all going to make more money, but also it was easier to convert

them when you got them on the phone.

So the first thing they would ask is, is this property available?

Which, of course, yes, it is.

And then they would want to understand the price and the breakdown.

So in 2015, rates were not rolled at all.

So you got to see you're enrolled, I mean, when your fees go into your rental rate.

So had very single fee from the very beginning.

And now you can show just the rental rate and the taxes if you want to, um, which

is helpful for those guests that might not understand that you have to charge

fees in order to make money as a business.

Amen.

A lot of the time we get these phone calls, um, just asking, what's

this cleaning fee, and what goes into it, and why am I paying this amenity fee?

Which was really required of us to charge to pay the

subdivision that the home was in.

And so really just explaining those.

And then in Destin, of course, you want to know how far the home is to the beach.

And here in Jackson it's how far do I have to drive to go skiing?

I love this.

This is taking us back in time with the reservationist.

Okay.

So you learn Excel.

I just wanted to pause there because a lot of the hosts that listen are newer

hosts and they're like, I can't tell you the last time I've picked up the phone.

You made a reservation last week for us.

I did pick up the phone and make a reservation for us.

But it was-- yeah.

And that's the--, I can't remember the last time I picked up the

phone to make a reservation at all.

Ooh, goodness.

I'm dating my--

Oh my gosh.

I'm dating myself.

Well, no, I'm really just thinking through the last time I picked

up the phone to book a reservation.

So, um, interesting.

There's tons to talk about, but maybe we just parlay

this into where you are today.

Your reservationists, what do their jobs look like today in Wyoming?

Is it a lot of phone calls in a cubicle or does it look different?

No, it looks a lot different, which was very hard for me to wrap

my head around when I first started.

I remember being like, why doesn't everybody wear a headset

and they're not at their desk all the time answering phones?

I don't understand.

Where is their Britney mic?

Yeah.

Right.

They have so much more flexibility in their roles now.

They're not having to sit at a desk with a headset on 24/7.

And that, to me, originally was jarring, and now is amazing just to show how

much things really have evolved in the past eight years at this point.

I mean, people don't want to talk on the phone as much as they did back then.

I don't.

I know that I don't.

To y'all's point, I never, ever, ever call to book anything.

I always book it online because we've reached this era of, what's

the quickest way I can do anything?

So they do a lot of talking back and forth on, um, live chat.

So we have a chat functionality on our website.

And guests just want that immediate connection with someone who is

sitting at their desk who can answer them via keyboard really, really

quickly, and they're not having to go through the touch tone of, press

1 for reservations, and press 2.

I mean, we all hate those.

I was trying to call my mortgage lender the other day and I was like,

well, I have to block off two hours.

Just to get through to someone.So much.

Phone call.

Yes.

Which honestly, everyone, this is a great reminder and tip.

It's the golden rule.

Treat others like you want to be treated, but also in terms of customer service,

what makes you angry when you're out there in the world trying to get things done?

How can we remove that friction from our potential guests?

Which also I want to point out, I love how you went home that weekend,

got some Excel, YouTube University, Excel spreadsheet lessons because

you wanted to do something that you didn't have prior experience in.

But what you did was you were a self-starter.

You're like, what can I do to show my superior, or my boss, or the director

that I would love to go in this direction?

And you went and you did something to show them you're excited,

and you followed through.

So that's another great tip for anyone out there right now wanting to get involved in

something, whether it is buying your first property, um, managing several properties.

What can you do for someone who is ahead of you to help you get there?

What was that new job like, um, when you moved from reservations up?

And was it everything you hoped it would be?

So scary because when you are, and everybody knows this, whether

you have one property or 700, when you are changing a rate for your property,

the amount of anxiety that you have of leaving out a zero is just insurmountable.

And it's really funny because I did leave a zero out.

Absolutely.

And I think it was like-- it was an expensive mistake

when I very first started.

And I remember just being racked with guilt and anxiety, and my boss

saying, this is a rite of passage.

When you enter into this role and you start changing rates, it happens.

Everybody screws it up at one point.

You don't do it again.

Once you understand and you feel this guilt and this anxiety of

someone booked this property for--

They stole it.

$40 a night.

Yeah, I know.

And it's awful, the anxiety that you feel, and you want to-- fixing it right away

and having to communicate with the owner.

I mean, it's definitely a mistake that if you make once or twice, you're like, okay,

I'm going to definitely take some extra time the next time I edit these rates.

I think a anxiety or just a fear that we have no matter how many

homes we have, and that connects us, everybody has to change rates for their

property no matter how big you are.

Well, I was going to say, listeners, Meaghan just said it.

It's a rite of passage.

You will do it.

I know this is the big thing, especially on Airbnb that gets you when you

send over a special rate and you forget to put the cleaning fee in.

There's just little things.

Or you know there's a big event coming to your town, you have it

written down on your to-do list, change the rate, you forget to change

it, and then somebody books and you're like, yeah, I gave it away.

I gave it away to them.

My question to you, Meaghan, is did you ever go to the guest and say,

hey, we made a mistake, or did you let the guest have it at that rate?

Yeah.

Oh, so you did.

Okay.

Because they know.

If it's $20, they know.

They know they're stealing.

Yeah.

And there has been a couple of-- this is all back in the 360 days,

there were a couple of errors.

There was one, we had acquired our largest local competitor, and

they also had about 200 units.

And so we doubled in size overnight, huge adjustment.

Forty employees that came over with the acquisition.

It's a great story.

And I was overseeing revenue at the time for, now, all these

new properties in our portfolio.

So I was adding all the rates to them.

I had no connection with the homeowners yet because I'd never spoken with them.

And it was all prior to go live.

Because the day that you announced the acquisition, you go live on your website

and you start booking those properties.

And so it was like 3 o'clock in the morning trying to get

it all done, left out a zero.

And we did approach the guest for those.

And it was an immaculate property, beachfront, over

$2,000 a night to rent it.

And I can't remember if I did it for $200, and I mean, it was a big mess.

Yeah.

Yeah.

It was certainly noticeable, and we called the guest and essentially

just said, please understand.

And then honestly, transparency, I think, we always say clear is kind.

And just saying to the guests, hey, we're human.

We do all these rates behind the scenes.

We completely understand that this feels like a bait and switch to you.

Please know that this is an error on our part, and we're not able to rent this

property for this price, but we have all these amazing properties in this

price range, which look a lot different than this beachfront property that you

were booking, but I'm sure-- I mean, to your point, Annette, they know.

When getting this at $1,000, this seems like a great deal.

This is a teachable moment, what you just said, that's why you

have to be on top of the reservations.

And the person most likely knows if they got a steal of a deal, there's a reason.

And it's one of those things, don't waffle too much.

Get right to the point with them, clear is kind.

And I think the faster you let them know this was an error, once two days,

three days, four, it's like, okay.

Now you're like, eh, I should have-- I'm not on top of my-- first of all,

I'm going to tell I made an error now?

It's taken me days to get back with them.

It's just looking like I'm not on top of it all.

So if you can get to them, I think speed matters in that time.

So listeners, if it happens, you got to make that decision quick.

Am I going to let them know?

And there's differences too.

Is it just a small error and you learn, or is it a really-- like

what you said, revenue is severely impacted by 2000 to 200 a night.

So they know.

All right.

So you just call, and you're upfront.

Let them know.

Upfront as soon as you notice it.

And here's the thing.

When the booking comes in and you're watching those reservations, everybody

is, no matter how many homes you have, you see it, immediately your stomach drops.

Don't waste any more time.

I think that putting off those conversations, I know I have been

there many times, seems much easier.

During Covid, having to call the guests letting them know that the beaches were

closed and vacation rentals were being shut down and we were going to have to

give them a credit versus a refund, I mean, I would rather, in that moment,

have delayed those conversations for days and days and days just so they

could be in the bliss that they were still having their vacation and they

were going to get all of their money back right away and-- just bite the bullet.

Just do it.

You feel better after every single time.

You might leave the conversation a little shaken, or you always

have the option of eating it.

You can pay for it.

And there have been times when we've done that too.

I think it really depends.

I think if you do wait longer than that 24, 48 hours, that's

probably the best thing to do.

Because it is your error, and the guests didn't do anything wrong.

Acknowledging that, I think, is important, especially if you've waited longer than

that 48-hour mark to let them know.

At that point, it's like, you should probably just pay for it.

Just take the L.

Yeah.

I call it eat the frog.

Someone once told me that because I was like, I don't want to do this thing.

But then it just weighs on you.

So eat the frog.

Get it done.

All right.

Talk to us now about the company that you work for.

What is your position now?

How many homes do you have?

And yeah, what does the team look like?

Paint us a picture.

Okay.

So let's see.

It's a totally different role than I had previously.

So I am the executive director of the Outpost Group, which is, you

can really see it as a mini private equity firm, almost like a family

office, I guess we would say.

It is definitely not a huge, massive corporate structure by any means.

I think that I chose very carefully to go from small business to small business.

Even with 600 homes, we were still very much a family at 360 Blue.

And the same is true at Outpost.

So at the Outpost Group, we have Outpost vacation rentals, and we

manage 250 properties that are all located in Jackson Hole, Wyoming.

Well, actually we have two in Watercolor, but those are family-owned

properties, and that's in the Panhandle of Florida as well.

But for the majority, 248 of them are located in Jackson Hole, Wyoming, which

is where our business is located now, and all of our employees are here as well.

Um, we also have a coffee roasting business that we purchased

about a year ago, which has been such an exciting adventure.

And that business, we were one of the largest customers, or the largest

customer, um, because we put mini bags of coffee in all of our units.

So it just made sense when the owner was looking to transition out.

And with that, we branched off and we started a little coffee shop in

downtown Jackson that opened last June.

So that's an interesting company.

And then we have Terrain, which is a landscaping and snow removal company.

Really the idea there is so many of our properties, of course, need snow

removal and landscaping all year long, um, depending on what season we're in.

And being able to control that experience by having our own company

and being the vendor allows us to take better care of our owners.

We also have a cleaning company called O2 Cleaning, which, um, all of our

housekeepers are employed by O2 Cleaning, and they're not contractors, which

is really different in the industry.

The first time I had ever seen that.

And then we have, uh, Provisions, catering, which we are a partner in.

And Provisions has been great because they're private chefs as well.

So we utilize them as our in-home private chefs for any high-end clients

that we have that come in that want to have a private chef experience.

And they also cater large scale events.

So if anyone's coming for a wedding, then, um, we're able to

really sell them on Provisions.

And I think that's it.

It's hard to keep track of them, but the Outpost Group, we have, essentially,

centralized marketing, finance, HR, and a little bit of operations with

this little family office that we have.

So we do all the marketing for all the entities.

We do all the finance, all the HR, so payroll processing, we create all

the budgets, um, and then we help out on the operations side as well.

So it's a little bit of a different setup than most companies, but

it's been really great for us.

Yeah.

This is why I think having you on our podcast is so brilliant, because

you have me all hyped up and inspired.

Because I know I talked to--

Do you want a landscaping company?

No, I talked to Annette about this before.

She saw me pull some weeds last week and now she

wants a landscaping company.

I can lay some mean mulch.

It's called Annette Mulching Services LLC.

No, because I've asked and I've thought about buying a laundromat.

Because in our metro market, laundry is such a pain point.

Or starting a cleaning company.

And obviously, it's for a very, very, very small business.

That's a big--

But it's possible.

But it's not, not possible.

And so I have so many questions for you because I feel like our listeners

are also like, wait a minute.

I haven't thought this big yet.

I could do these things.

Or they have the business already, or a family member or

someone they know they could loop in.

AD MARKER

My first question to you is, is it okay to assume that you

not only service your properties that you manage but you also offer

these services to the community?

Is that correct?

Yes, that's correct.

Do your homes take precedent?

It's okay, because I would.

I'm not lying.

Work comes first.

Because we have guests if--

Yes.

Okay.

So it's difficult.

So snow removal season, if there is an avalanche or something crazy,

because things like that happen in Jackson, Wyoming, which is

very new to me, but it is real.

Or if there is a flood because of an ice dam on someone's roof, and

if they're not an Outpost client.

If it's an emergent situation, then they definitely take priority.

On a normal day, we definitely try to prioritize.

God, this is terrible.

No.

I don't think it's terrible.

That's why you guys have--

That's why you built it.

Yeah.

I'm going to ask you the most-- just get it out there.

Comparatively, when you were in Destin, did you have any of the

stuff in-- you did not have any of the stuff in house, correct?

Because you said this is the first time you're--

No.

Our cleaners were contractors, and everything else was

really contracted labor.

Yeah.

Do you feel like-- is it a night and day difference?

Could you ever imagine going back to contractors again?

Is it a whole new world having all of this right there under the same roof

at your disposal, and as employees?

Yes.

I definitely think it depends on your location.

That has a huge, huge part in it.

In Destin, there are 15,000 vacation rentals along the stretch

of 30A and Santa Rosa Beach, a little bit past Destin, 15,000.

In Jackson, probably 800, 800 to a 1,000.

Very, very small.

The cleaner situation or the housekeeper situation in Destin,

there are thousands of housekeepers.

Here in Jackson, you don't have any outskirts to live in.

There is not really a cheaper area.

There is, but it's going to take you an hour and a half to drive

here, and you're not going to be able to get here in the winter.

And I think that this is the case for a lot of ski markets, um, or

mountain destinations in general.

Just the labor crisis is so real.

And I think having our housekeepers as employees that are eligible for

health insurance and other benefits makes all the difference in the world.

It is definitely more expensive as a company, but the retention of housekeepers

is a night and day difference.

Absolutely.

And just feeling like a lot of times it's a little bit like they're

not really a part of the team when they're contracted laborers, and

you don't really get the opportunity to spend a lot of time with them.

And this situation, when they are employees, you feel like one team.

And I think there's a level of appreciation that's there for the

housekeeper that maybe doesn't exist when they are contracted laborers.

I would love also, and this is where you can't really quantify

this in spreadsheets, you just said, hey, it's more expensive to have

this stuff in-house, but I believe over time, it's an investment.

It's a human capital investment, and over time, I think, hopefully, makes

you a lot more money just because you're not having to give any refunds

because of the type of work that's done.

You are not having to scurry, and just mental mortgage, that space that it's

taking up, and all of your heads wondering if things are going to get done well.

And so it's one of those things that I encourage everybody, it's hard in

the beginning because you see bigger dollar signs, but in the long term,

I think it's a huge investment.

Do you know when they decided to do that?

Was it because it was such a pain point or what that inflection point

was for them to bring it in-house?

Pain point is definitely part of it.

I mean, I think that every manager goes through this time period of, Sarah,

you mentioned it earlier, you start to think, do I need to buy, or should

I start my own landscaping company?

Because depending on these vendors sucks.

It's terrible.

And in Destin, it was pool vendors.

Oh man, I can't imagine.

Yeah.

Oh my gosh.

Eight percent of our properties had pools, and when the pool heaters

weren't working, which they never do, in Jackson, it's snow removal.

You've got to get out of the driveway.

And when you're calling vendor after vendor and they have

no-- you're not a priority.

They have a million other jobs to do.

They're the only vendor in town because you live in Jackson, Wyoming.

And so they have this monopoly and control over you.

And so I would say it's probably two to three years ago.

It was definitely before my time at the time I started.

And it's funny because when I first started, I was like, can't believe

you guys are doing it this way.

It's so expensive.

It's very similar to the sales crew or what we call the reservations team.

When I first started, I was like, well, what do you mean they're not

at their desk answering phones?

You have to unlearn what you have learned over time, which is that

contracted cleaners are the way to go, and your reservations team, no

matter what, should be answering every single phone call within 10 seconds

and sitting at their desk all day.

Some people might say that those are a thing of the past, and I think that

unlearning what you've thought you'd known, especially in an industry that's

really new, I still think vacation rentals are really new, and I think we

have evolved so much over time, and it really requires-- it's so funny because

I preach to the team all the time.

They're probably so sick of hearing it, like, we will pivot no matter what.

I am never too dedicated to one decision.

We'll admit when we're wrong.

We will change our processes accordingly.

We'll try something, it won't work, we'll try something else.

I'm never married to anything.

It is important, especially in this industry, to evolve

as the times start to change.

And it's funny because I'm looking back on this being like, am I a hypocrite?

But I definitely had to change my mind, and I think that it's

been for the better, 100%.

Because there's probably things that you think about "pivoting", or not

having your mindset on something, but then there are things that you don't even

think about that there's a way to pivot.

Because it's so ingrained in all you've ever known that, of course, you

come to this new company and they're doing things way different, and you're

like, oh my gosh, your mind is blown.

So my question to you is, you have a lot going on.

You have a lot of different businesses.

They're not all directly related necessarily.

I mean, they all help each other out.

But you mentioned key performance indicators.

I think this is a great conversation for, if you've got one property, you

still need to measure your performance to make sure that you're staying

profitable to not only 250 homes but all these ancillary businesses.

What do you guys focus on?

So I think when you're talking about the vacation rental industry, um,

in general, like you said, whether you have one home or 250, a lot of times it's

really easy to focus on your revenue.

And that's your main key performance indicator.

I'm at $60,000.

Last year, at this time, I was at $55,000.

Where is that $5,000, and how can I make it up throughout the year?

Revenue is a huge piece of it.

That's my background.

That is what I always go back to because that is literally how you

can keep your business afloat and your owners happy if you have owners.

But there are so many operational KPIs as well.

So on the maintenance side, I think it's really important to understand your

own performance, whether you have an in-house maintenance team or you have

contracted, um, laborers that come in and fix a plumbing issue that you have.

Understanding how many of those work orders you're getting.

So how many complaints have I gotten about this toilet?

I've gotten three complaints this year about this toilet, and it typically

takes the contractor that I'm using three days to resolve this issue.

And I'm usually having to refund $50 a day for it, or whatever number.

Okay, well over time, that's $150.

That's three guests that the toilet has impacted.

And understanding those numbers and writing them down, whether it be in

a spreadsheet, I would always choose a spreadsheet over everything else,

or if you're a larger organization and you have a software that you can

input this information in to monitor, that's when you want to pick up the

phone and call your owner and say, maybe you should get a new toilet.

Having this data is really, really helpful.

Or if it's your home, maybe you should get a new toilet.

This data tells us something.

Or if the resolution time with this one vendor that you're using is

longer and longer every single time, maybe it's time to switch vendors.

But I think that if you're not monitoring this and you're not writing it down, we

are all so busy, and we forget about it.

So we call the same vendor.

So we don't fix the toilet.

And at the end of the day, it's eating the frog.

I saw this thing.

It's eat the frog first.

First thing you do in the morning, eat the frog.

Get it over with.

Get it done.

And so I think monitoring the performance of those things, like I

said, whether it's in-house or you're using contractors, on the guest service

side, how many, um, complaints have I gotten this month, and how long has it

taken me to resolve those complaints?

How many dollars have I refunded this month?

We monitor refunds like crazy, and we set goals for the team that's

responsible for giving those refunds, that guest service team, so we can

ensure that we are keeping an eye on how much money is going out the door.

And if it's this one incident that keeps popping up, that we're fixing

it and communicating right away with that owner that it needs to

be fixed for future reservations.

If you can, give us some examples of what you do refund

for when a guest reaches out.

So if a guest books a specific unit for a hot tub but the hot tub doesn't

work for their entire stay, we all know those, I booked this property for this

reason, and then it doesn't-- I know.

And you're like, okay.

Um, so we do refund for those.

And I think it's hard to put a value on those things.

That's really where you find yourself in that position where you're like,

okay, what is the actual value of a hot tub every single day?

How many days have they not had it?

And you have this like internal battle of, I could either offer

them $150 and they laugh in my face and think that I'm so insensitive,

or I could offer them a $1,000.

And they're like, I just freaking took this $1,000 street to the bank.

I wasn't even intending on using that hot tub.

And I think that is really where I would say I'm very much a data

person, but I think gut matters there.

Talking with your guest, understanding their story, and how much use they were

going to get out of this particular item.

Cleaning complaints, I would say, number one, we all deal with them no matter what.

Even if our cleaners are employees, of course, there are instances we have

where we have to refund cleaning fees.

Um, and I think that really depends on how impacted is

this guest's day by this issue?

And really quantifying that to you is understanding your guest, and how

upset they are, and why they're here in the first place, and what they were

planning on doing with this hot tub.

Or if they were going to have a dinner tonight with their whole family, and

now the floors are all disgusting and we have to send a cleaner back.

I know that that's not a cut and dry answer, but I really

don't think there is one.

I think it's different every time.

And the cleaning, just to touch on it, you will send

someone back out plus do a refund there in some situations, correct?

Some situations, absolutely.

Um, and I really think that that's our way of, we want to

lock in this guest to come back.

Not every single guest we want to come back.

We've all experienced those as well.

But for the most part, we're trying to lock in a repeat renter, and it

depends on how severe the situation is.

Okay, if there's sand on the floor or dirt on the floor, then like,

hey, we'll send somebody back.

We'll get that mopped up right away.

And if the guest is like, absolutely, that sounds great, no,

we won't refund their cleaning fee.

If the guest comes in, a bathroom's disgusting, they found sand in their

bed, um, that used to happen in Florida all the time, unfortunately, we're

sending someone back right away to remake the bed, and we're going to

take some money off your cleaning fee.

I think it just depends on the severity of the situation.

And of course, you get the guests that are irate, but you also have the guests that

are like, sure, of course, remake the bed.

No big deal.

We totally understand.

It happens.

Yeah.

Those are the best guests.

Thank you to those guests.

Also, I feel like I'm getting a lesson in, if I want a better refund as a consumer,

I just need to come in guns ablaze.

No.

I don't have that in me.

I wish I did, but actually, I don't wish I did.

I'm okay with being a flexible guest.

All right.

We could talk to you all day.

I said a million times.

So I do want to get into, as the business you are 250 properties plus

all these businesses, what's going on right now in your market, in the way

you guys are running things as you see the future vacation rentals now post

Covid being, um, new to all of us?

What's going on?

I know that's a vague question, but take that for whatever you will and give me the

first thing that comes to your brain as to how you guys have pivoted since then.

Things are a lot different now.

It's really funny, when I first started in 2015, our hands were on the wheel all

the time when it came to rates in revenue.

We are decreasing pricing.

We're increasing pricing.

We are very, very hands-on.

Absolutely no cruise control.

Covid happened, and after the couple of months that we all had of, are

our businesses going to fail, what does this mean for us, are we going

to make it out of here alive, then things blew up in the industry, and

you're cruise control all the way.

All you were really doing was pressing the increase button on your rates.

And what you had to worry about was, can I take care of all these guests that I have?

I've never seen anything like this before.

You were so focused, or we were so focused.

I think the whole industry was of service.

You're very service-oriented.

Revenue, we're printing money right now.

We're not having to worry about anything.

And I think that we've seen, um, I know that we have in Jackson, and I've talked

to a lot of other managers as well, since beginning of 2022, maybe last

spring, things look a lot different.

You are not on cruise control anymore.

There has been a regulation that has started to happen, and we've gone back

to this 2019 pre-Covid era demand levels.

The world is open.

People are traveling to all destinations.

I mean, you talk to one person and they're like, it's because

travel to Europe opened up.

That's why everybody-- and then you talk to another person and

they're like, it's the economy.

Gas prices are really high, and people are wanting--

We don't know.

I think it's a combination of everything, but all we know is

that it does not look like what it used to for the past three years.

We are not on cruise control anymore.

We do have to lower rates sometimes.

And, um, I think educating employees that came on during Covid that maybe

weren't used to that has been difficult.

Understanding that setting rates for next year doesn't necessarily look

like increasing across the board.

It is very, very intentional at this point, and we have to monitor that demand

more than we ever have before because it is not completely unconstrained, and we

have so many people wanting to book and we don't even have enough availability.

Um, and I think that that's a good and bad thing.

I think it's initially scary because you're like, okay I've spent the last

three years not really worried about this.

But I also think there are blessings in it that your team needs a break.

Our team needs a break.

We all needed things to go back to normal.

They were going to eventually.

And I think now, for us, it is a lot more reliance on those KPIs, and talking

about the importance of marketing, and ensuring that our rates are a fair

price compared to our competitors, and that we are taking really good care

of the guests and coddling them when they're here so they want to book again.

I think depending on those repeat renters now more than ever is really important.

Yeah, it's different.

It's really different.

Since you are a management company, how are you letting

the owners know that though?

It's an easy conversation to have here on the podcast, but what are you doing

when you're confronted with someone?

And I know we have a lot of listeners that are like, what's going on?

Is the market saturated?

So how are you having the conversations with the owners that

there is a steep decline in revenue?

So it's funny because there's another internal battle.

I think there are so many in this business where you're like, do I wait for my owner

to notice that things are a little bit softer than they were last year, or do I

get out in front of them now and tell them what's going on without causing panic?

I would always choose the ladder.

I think it goes back to clear is kind.

Owners are going to notice, or some of them are at least, the

revenue-driven ones that have to pay their mortgage, that depend on this

income to send their kid to college.

Whatever it is.

They're going to call you.

You do not want to be on the other end of the phone when you haven't

already reached out proactively.

It's just not a good look.

And I think it's one of those eat the frog first things too.

They're not fun conversations to have to talk to your owner, but I think that

you are the expert in this situation.

You have access to the data because you do.

You have your past data, you have tools.

There are a thousand tools that exist right now to use.

I would encourage using one, or even talking to somebody else in your

location I think is really helpful.

And I think as managers, there is a little bit of anxiety there, wanting

to keep things really close to the best, um, but I always encourage it.

Everybody's going through the same thing you are too.

You just want to know that you're the best, and that you're keeping

an eye on things, that you have the data in front of you.

So we send our owners an email every single month with revenue information.

Of course, you want to put a spin on things.

I don't necessarily think that making everything seem

great is the right decision.

I think just letting your owner know that you're aware and what your

steps are to fix or remedy whatever you might be seeing in the data.

So for example, hey, occupancy for this July is 5% lower than

it was this time last year.

We understand that you're likely looking at this too, and you're keeping an eye

on your reservations in the future.

The great news is, June, 15% better than it was previously.

We see those weeks fluctuate from year to year.

On the marketing side, we have scheduled your home to have new photos taken.

We are sending out these two emails to our database of 10,000 people this month,

and we typically see a return of X.

And I know that sounds like scary, but this is pretty easy data to get ahold of,

like I said, no matter what size you are.

Um, and I think once an owner reads that email, they're like, oh, okay.

They see it, but it sounds like they're really on top of it.

Yeah.

and listeners, I will encourage you, if you're not a manager of other people's

properties, do this for yourself because Annette and I see it all the time.

Our people tell us they feel like occupancy's down, they

feel like their revenue's down.

And we often ask them like, okay, but do you know that it is, and compared to what?

And like you said, okay, July is down, but June is up.

We have to look at this holistically.

And so a lot of our listeners are owners of their own property, and

I'm sure most of you got into this and own your own property to build

wealth, but also to cash flow.

And so it's just important to keep these metrics for yourself

too, and to report to yourself.

What if our listeners, Meaghan, they are self-managing

right now and they're like, you know what, I don't have the time anymore?

I love my property, but I want to see if I can hire someone to help me with this.

What would you tell our listeners who are maybe thinking about hiring

a management company or a co-host to help them with their property?

If you were in their shoes, what would be the top two or three things

that you would make sure that the company that they're going to hire

is doing or promising they will do?

Okay, so this is a great question, and I have a house in Florida

that is currently for sale, but I have toyed with renting it out for a long time.

So I think about this pretty often.

Um, I think the first thing that you need to understand as an owner,

and this depends on what type of financial situation you have.

For me, it is, what do I need to cash flow?

To be able to either pay my mortgage or have this play money that I want, whatever

you have for your second property.

So what do you need at the end of the day?

Because it's going to come down at some point to a management fee, whether

it is a 15% management fee, or in ski destinations, often it's 35%.

That's the norm.

And so if I pay 35% to a manager, am I still going to be able to pay my bills at

the end of the day if I have a slow month?

So that's the first thing.

The second thing is, is there a dedicated person that I can communicate with?

I think it's really, really helpful.

I think for a lot of companies you call in.

And we talked about this earlier, having to call in and press the touch tone.

Um, one thing both at Outpost and at 360, you have a dedicated property manager

that you were assigned to as a homeowner.

Love that.

It makes all the difference in the world.

This is your home.

You care deeply about it, especially when a lot of strangers are in your property,

uh, no matter how amazing they are.

That is a little bit scary to think about.

And you want a connection with somebody that you don't have to go

through 30 minutes of waiting on the phone to get to this person.

This person knows your home.

They're in it frequently.

Um, you can communicate to them what is really important to you.

I think that that's also very important when you're shopping

for a management company.

Oftentimes you find owners are either very, very income-driven, or they're

not so income-driven, they're very driven on the care of their property.

Communicate that very early on because your manager needs to know that.

They're either going to lower your rates during a downtime.

I could go on and on all day about how lower rates does not increase

wear and tear on a property.

I think that that is like the biggest myth in our industry.

I think most people would probably disagree with me, but like I've

seen people spend $30,000 on a property and totally trash it.

I think maybe there's more entitlement.

When you do spend $30,000 on a home or a significant amount--

anyway, I think that's a myth.

Not afraid to say it.

But I think communicating that want with your, um, with property management

companies when you're shopping around, and I encourage people to shop around.

It's very, very important.

Um, and then asking your manager, okay, do I have a dedicated person?

I know my management fee at this point.

I really like this company.

Okay, so now you understand that I am really in the middle.

I care deeply about the care of my home, but I also need to be able to cash flow.

Now my manager knows this.

What are your strategies?

Do you have somebody that's dedicated to revenue that's really

keeping an eye on those things?

Is it all automated on a computer?

I would not choose someone who had fully automated revenue.

I would want someone that has either a dedicated person or a

dedicated team that is keeping an eye on those things that's really

studying the trends in the industry.

And what are you doing to market my home?

Which everybody gets that question, but I do think it's really important question.

Is it a company that's really focused on OTAs, that they really want to do

whatever they can to, um, just get your property on Vrbo looking great, have

it ranking high with the algorithm?

Or is it a manager that really focuses on direct bookings and they want

to have as much website presence as they possibly can, so they're not

putting as much energy into the OTAs?

Then I would ask them, okay, what's your direct booking person?

God, I'd probably be terrible at book picking a manager.

They would be like, miss, you should do it yourself.

Leave us alone.

No.

Those are great things to think about.

Yeah.

Yeah.

Marketing and revenue.

I think that's a large thing, people.

Like you just said, oh my gosh, they have a list of 10,000

people that they can market for.

They have a revenue manager there.

Uh, my last question about this is, because I know this

is all over the board too.

And you don't have to say which company, just to keep it out there.

What happens if you're managing and you have an owner that really wants to use

the property during all the peak times?

Is that a clause in your contract?

I'm just thinking, if I'm looking for a manager and I'm like, well, I want

to use it on Christmas, and I want to use it on New Year's, and I want

to be able to give it to my friends and family whenever, how do you deal

with clients like that that basically want to remove all of your revenue

generating dates from the calendar?

We appreciate you so much as a homeowner, but we are a business,

and in order for us-- here's what we really do, is we give them the data.

We have a full reservations team, a full guest service team.

We have someone dedicated to your property.

All of these employees are being paid more than a livable wage to be

able to take great care of your home.

We have a revenue manager.

We have a full marketing team.

Um, these are benefits that are offered to you in exchange for a management fee,

but both of us are only making money when we are bringing in reservations.

We're not making a management fee if you don't have any bookings, so we have

a caretaking property or a caretaking program that we would love to talk to

you about where you don't have to rent your home and we take care of it for you.

Oh.

Boom.

Yeah.

We have that at Outpost, and at 360 we called it maintenance only.

And so one thing at 360 Blue that we had was, we would automatically convert an

owner to the maintenance only program.

I think it was 30 days, if they stayed longer than 30 days or something.

Because a lot of times when owners are staying, they're requiring a

lot of your team, and you are not making a single penny off of it.

They're in town.

They want to talk to you on the phone about getting a

private chef over to the house.

They have an issue with the toilet.

All the things.

And, um, that can be challenging when you're not bringing in any money.

And especially if you have a smaller operation and you're paying your team

members, you need them focused on homes that are bringing in income.

I love that.

So both of the companies had a maintenance program or a caregiving program.

Love it.

I know.

Because it's not no, it's not yes.

Not way you want to do it.

Yes.

I know.

And we can offer you this program.

It's perfect for you.

Meaghan, this was amazing.

I could talk to you all day.

You guys are crushing it out there.

We're so excited for all that's ahead for you and everything

you're doing for the industry.

Is there anything you want to leave our listeners with before we sign off today,

anything we didn't touch on or that you wanted to share just sitting in a seat

that you sit in with our listeners?

I think that it's a tough industry.

A lot of times in the roles that we're in, it's not very glamorous.

We are talking to angry people, or we are dealing with complaints, or

we are just inundated with things, whether every single guest is happy.

It's just a hard job.

You're doing a lot every single day, and especially for those that only have one

person, and it's themself, and they're managing one property or two properties.

I think that you get into the minutiae of your day-to-day,

and it can be pretty exhausting.

So I would say that what we do is actually really exciting because for the most

part, these people that are coming to stay with us, and I think that this message

gets lost in the day-to-day so often.

I know it does for me.

Sometimes they're saving up for two years to take this vacation, and it

means so much to them, and we really are making these incredible memories,

and they are actual people too.

We all go on vacation when we save up.

We take the time off work.

We're so excited.

And I think doing whatever we can to really recognize that as hard

as the job is on a day-to-day level, it is so meaningful to our

guests, I think is really important.

It brings a little bit of happiness back into the job when

things can start to get rough.

And if you have one property, and I know it's probably really easy to

get lost in the day-to-day, but what I would say to you is, stay up with

what's going on in the industry.

Talk to managers in the area.

It is impactful to you.

Change is impactful to you, whether you have one property or 200.

So communicate with somebody that you can consider a mentor in the industry, or

get on LinkedIn and make connections with people in other destinations if you don't

want it to be in a competitive market.

Read VRM Intel.

Become a member of Verma.

There are things that you can do to make connections that make you feel a little

bit more connected in the industry.

We're going to put your LinkedIn in the show notes, so hopefully

you'll get some outreach requests.

And we want to have you on an after show on Instagram so we

can-- I want to talk about coffee.

I want to talk about how the coffee's impacted the business.

No.

Meaghan, you are a wealth of really cool things that your company

is doing and that you're doing.

So we can't thank you enough for your hour this morning when we were recording this.

Yeah.

And so, listeners, we hope you enjoyed this conversation as much as we did.

With that, I am Sarah Karakaian.

I am Annette Grant, and together we are--

Thanks for Visiting.