The Anchors of STR

What is The Practical Property Manager?

Transcripts from Steve Schwab's newsletters

Cedric: It was just short of two
years in business when I felt the

weight of losing our first homeowner
because of something we had done.

Looking back, I had unrealistic
optimism of thinking we

would never lose a homeowner.

I still remember the feeling
that hit me at dinner that night.

My mind wouldn’t stop.

Unable to sleep, I got up at 4 am and
without any real plan, drove five hours to

the owner's home to meet them in person.

My hope was to save the relationship.

The Mexican US border opened at 6:00
am, and I was there in the dark with a

coffee I bought from a roadside stand,
waiting to cross north to drive to Tucson.

By 9:00 am, I was parked in a Home Depot
parking lot, calling the homeowner.

“Hey Mike, this is Steve, I drove
to Tucson to come talk to you.”

Silence.

“Mike, are you still there?”

“Steve, you didn’t have to do that.”

“Mike, I wanted to show you how
important your relationship is to me.

When can we meet?”

I spent 5 hours that Saturday
with Mike and his wife, Betsy.

In the short-term rental industry, we
spend a lot of time talking about growth.

How to find new homeowners.

Conversion rates.

Cost of acquisition.

Brooke Pfautz built an entire
company around it with Vintory.

But for all the energy and money poured
into portfolio development, I rarely hear

operators talk about the most important
KPI in business development: churn.

We ask our team to share
new properties every week.

We don't often ask, "Who kept an
owner from leaving this week?"

Customer retention is
business development.

It’s not a lack of growth
that hurts a STR company.

It’s losing owners you already have.

Vacasa didn't fail because they
couldn't find new homeowners.

They failed because they
couldn't keep the ones they had.

Average operators think this is a
transaction and logistics business.

Good operators think it's
a hospitality business.

Great operators think it's
a relationship business.

The best operators know
it's all of the above.

Competence, character, and compassion.

That's what builds a trust-based business.

Baseline STR Anchors

They say that the majority of a guest's
opinion of the property happens in

the first 15 minutes of their stay.

The same principle applies to homeowners,
it just plays out over a longer timeline.

My friend Graham Donoghue, Group CEO Forge
Holiday, shared the power of retention

through the lens of Homeowner firsts.

This stems from the psychological effect
of anchoring bias, the idea that early

experiences disproportionately shape how
every future experience gets interpreted.

These first moments become the
emotional benchmark everything

else gets measured against.

In Casago, we nicknamed
these: Heroes and Zeros.

You get to be one or the other.

No in-between.

The contrast in outcomes is significant.

When you execute these moments
well, retention increases as much

as 80% over the first three years.

The anchors are specific.

The first communications
after contract signing.

The first time an owner
sees their listing.

The first reservation.

The first damage claim.

The first work order.

The first owner statement.

These STR anchors are your baseline.

Once an owner decides “these people
care about me” or “these people are

disorganized,” they begin filtering
everything through that lens.

That’s confirmation bias as work,
and it stacks the odds against you.

A negative first impression
doesn't just create a bad memory.

It creates a filter that makes every
future interaction harder to win.

Get the firsts right, and
you don't just keep owners.

You build believers.

Anchor 1: First Communications
after Contract Signing

Send a thank you.

A real one, for goodness sake.

It still shocks me that homeowners hand
over their most valuable asset, their

property, their investment, often a
place full of personal meaning, and most

operators never stop to acknowledge it.

No gift.

No handwritten note.

Nothing.

Bill Feath, one of the most successful
STR hosts and coach I've come to respect,

calls this "Earning the Right to Fail."

The idea is simple: when you show someone
early that they matter to you, you're

making a deposit into the emotional bank.

So when something goes wrong,
and it will, they already know

they're not just a number.

That deposit is the difference
between a homeowner who gives you a

chance to fix it and one who quietly
starts looking for your replacement.

A thoughtful gift and a handwritten
note cost almost nothing.

What they buy is trust before you've
had a chance to earn it the hard way.

Anchor 2: First Listing

An owner just handed
you something personal.

Whether it's a second home
or an investment property,

that place carries meaning.

And it just became public.

That's an identity transfer, and
it's psychologically vulnerable,

whether they say so or not.

In that silence, they're
evaluating everything.

Did you see the beauty of this home?

Did you understand what makes it special?

Did you tell its story, or did
you reduce it to inventory?

Did you present it with pride,
or did you rush to get it live?

A generic listing sends a signal they may
never articulate but will never forget:

"Your home is just another unit to us."

A thoughtful one creates
something different.

It tells them: "We see what you see."

Anchor 3: First Reservation

The first booking is not just revenue.

It’s about proof.

Proof that the market wants their home.

Proof that they made the
right decision trusting you.

The speed to first booking, communication,
and excitement around that first

reservation psychologically matter far
more than the booking value itself.

This is why great operators celebrate
first bookings internally and externally.

Because emotionally,
momentum creates belief.

And belief is what keeps an owner
through the slow seasons, the

difficult guests, and the hard
conversations that are coming.

Anchor 4: First Damage

Every owner knows damage will happen.

That's not the moment that
defines the relationship.

What defines it is what you do next.

This is where they find
out who you really are.

Do you hide the problem?

Delay the call?

Minimize the concern?

Get defensive?

Or do you show up like a steward,
someone who treats their home the

way they would treat their own?

Here's what most operators miss: a
well-handled damage event often creates

more loyalty than a flawless track record.

Not despite the problem.

Because of how you handled it.

That’s the Service Recovery Paradox.

Trust built through competent
recovery can run deeper than trust

built through perfect performance.

Guests remember great recoveries.

So do owners.

Anchor 5: First Work Orders

This is where owners start
judging operational seriousness.

It's also where they begin asking a
harder question: is your stewardship worth

the cost, or would they be better off
managing it themselves through an OTA?

The ground game is what
separates you from the platforms.

They can't do this part.

You can.

The owner is evaluating
everything: Was it proactive?

Documented?

Fairly priced?

Efficiently handled?

Clearly explained?

Did it feel transparent, or
did it feel like a surprise?

The first maintenance
interaction sets the lens.

Either you're a protective steward,
or you're an uncontrolled expense.

Anchor 6: First Statement

This is the moment the relationship
becomes economically real.

Owners aren't just reading numbers.

They're interpreting fairness,
transparency, competence, and alignment.

They're asking, consciously or
not, whether you're on their side.

Confusing statements
create cognitive stress.

Clear statements create
psychological safety.

That document is saying one
of two things: "You can relax.

We have your back."

Or: "You'd better keep
watching us closely."

80% of decisions are emotional
before they are rational.

Churn is no different.

The firsts shape how homeowners
interpret everything that follows.

But anchoring is only the beginning.

Like any long-term relationship,
homeowners are constantly

evaluating three things, even
subconsciously: "Am I happy here?"

"Do I believe there's something better?"

"Is this still worth what I've invested?"

Psychologists call this the
Investment Model of commitment.

The longer the relationship exists,
the more emotional and financial

weight those questions carry.

What most operators miss is that
homeowners emotionally leave long

before they formally terminate.

Responses get shorter.

Engagement fades.

Conversations lose warmth.

Small frustrations that once
would have been overlooked

start carrying more weight.

The homeowner quietly starts exploring
alternatives while still under contract.

By the time most operators
notice, the relationship has

already dissolved emotionally.

There are far more anchors
than the ones I've listed here.

Map your entire homeowner journey
and engineer each touchpoint

for trust and retention.

I have over 300 owners in my hometown who
have been with me for more than 10 years.

The operators who keep homeowners for
decades understand that retention isn't

built on performance metrics alone.

It's built through relationships.

As for Mike and Betsy, they didn't stay.

They left for another
property management company.

But I kept the relationship alive.

A few years later, they introduced
and advocated for us at a

new resort in a nearby city.

That became Casago's first
expansion to a new market.

And there, they became
our homeowners again.

They're still with us today.

25 years later.