Manage to Exit

Can ChatGPT tell you what your property management business is worth? A seller recently tried — and the number came back $300,000 too high.

In Episode 6 of Manage to Exit, Aaron McElhiney and Hunter Goodall go hosts-only for a short, direct conversation about two things that quietly cost property management buyers and sellers real money: relying on AI to value a business, and choosing the wrong banking partner for an acquisition.

On the AI side, they explain why ChatGPT is a useful starting point but a dangerous authority — it doesn't have access to the off-market closed-deal data that actually drives valuation, it's agreeable by design, and it anchors sellers to numbers the market won't pay. With 450+ closed transactions behind them, Aaron and Hunter show where AI helps, where it misleads, and why value is built on cash flow and EBITDA, not gross revenue.

On the lending side, they break down a real New York deal that stalled for months under a general SBA lender — and how switching to a bank that specializes in PM acquisitions turned a stuck deal into a 45-day close. The lesson: 'SBA preferred' does not mean the right bank for your deal.

If you're buying or selling a property management business, this episode will save you from two of the most expensive mistakes people make.

Chapters:

00:00:00 — Cold open: AI, valuation, and the right banking partner
00:00:35 — Introducing the hosts and the show
00:00:51 — Story time: when ChatGPT valued a business $300K too high
00:02:50 — How to actually use AI in a valuation (without getting burned)
00:07:30 — Why the off-market data gap makes AI valuation unreliable
00:11:07 — The New York deal: why the wrong bank kills your timeline
00:13:36 — Choosing a lender: relationship, trust, and industry fit
00:16:11 — The PMI advantage: lending relationships that scale to franchisees
00:19:47 — Closing: the right banking partner is critical

Ready to know what your business is worth?
Book a free, confidential valuation call with Hunter ➔
No broker fees. NDA-protected. Only you, Aaron, and Hunter until you decide to move forward.

What is Manage to Exit?

Manage to Exit is a PMI Acquisitions Team podcast sharing practical playbooks for buying, building, and preparing your property management businesses for successful exits.

having the right
banking partner is so critical.

If you're trying
to get into acquisitions,

whether you're doing one deal
or $100 million worth of deals,

it's like you gotta find
who the right banking partner

is that that fits
what you're trying

to accomplish there's probably
a lot of interesting ways to use

AI with the information
that is out there, too,

when it comes to, like, even
preparing your business to sell

or what factors might impact
value, which add value

to their business like there's
definitely ways to utilize that.

All right.

Welcome everyone to the Manage
to Exit podcast myself Aaron.

And we've got Hunter here

we are the acquisitions
team here at PMI.

And we talk all about
acquisitions in the property

management space.

So thanks for tuning in.

All right.

Okay, so story time, you know,
we look at a lot of deals,

and something came up this week
that I was like, oh, okay.

We got to talk about this.

So, we were looking at a deal.

And, you know, every deal
that we look at, especially with

property management businesses,
we have so many past deals.

One of
like all these different sizes.

So we have so many comps

specific to property management
that we can refer back to like,

okay,
we can value this business.

And we have a handful
of very similar

sized businesses
to kind of back up.

Why we think the business
is worth here.

Right.

And we're looking at this
business and we're like, okay,

here's where we would
put this, this valuation.

And we've closed recently closed

like four deals
that match that size. Right.

And then somebody plugged
in, hey,

what's this
business worth into ChatGPT.

And it was like 300 grand

off like off of what we were,
you know, going for.

And I'm like,
I don't know that I would trust

a high like, value a business,
you know, like,

I don't know if it's It's
got to be part of me.

Yeah, I got to be part
of the equation in some cases.

But yeah, you're right
there. There is a big gap there.

And it really just shows,

you know, you've got to pull
in multiple resources.

You can't just assume
that chat's going to give you

chat doesn't have access to the
closed deals that we've seen.

Right. We've done

450, 460 plus transactions,
all off market deals.

And we've never shared
those comps with anyone else.

Aside from people
we're doing valuation for.

So but yeah, chat gave us
a pretty wide range there.

Really created
kind of like a little bit of,

you know, I'd say
like false expectations for,

for a seller to write.

Yeah.

And I think it's it's dangerous
on both sides of that equation.

You know, it's it's like for us.

Yeah we, we do use ChatGPT,
but it's to assist us in like,

hey, I know what I'm doing,
but could I use like,

what am I not seeing here?

And so it's like, yeah,
we have AI.

That kind of helps guide
some of some of our valuations.

But we've done this
so many times that we know,

hey, I need to push back here
like chat.

I see where you're going.

Like why you're
putting the price tag up here.

But there's there's
some subjectivity

that you're missing. Like
I know what to push back on.

And then chat is so kind
and polite

and there's always going to be
like, you're right.

You know.

Yeah. And so.

And I think chat
maybe one of the AI tools

we're probably most familiar
with and most people are

there's obviously
a lot out there,

but even last week
I was dealing with a seller

who owns a short term
rental management company,

and we were going back and forth
post valuation.

I'd already given a valuation,
and all of the counter terms

and questions
were all directly from chat.

It was copy and pasted.

I was not negotiating
against the seller.

I was negotiating against chat
at that point

and there was
definitely a disconnect.

The seller was relying
so heavily

on chat's influence
that I don't really know if they

they fully understood
what they were asking.

They just assume that chat knew
more than they did.

And, and they were happy to
just kind of push that on to me.

But but yeah,
just get interesting.

Right.
It's a it's a valuable resource.

But you got to know
how to use it.

Yeah.
I don't know that I like chat.

We'll get there.

You know,
I think it's increasing

in its abilities
every single day.

And it's
getting smarter and smarter.

But I don't know that it's
a wise decision to rely on it.

You know, like

there's so many people

that are trying
to buy businesses out there

or trying to sell businesses,
and it's like,

oh man, I'd be cautious.

Like ChatGPT is gray.

It's a good starting point.

But you know,

if you're trying

to buy a business
and you're like, hey, chat,

what should I pay
for this business?

It might it might tell you
to overspend by a few hundred

thousand dollars, you know,
and and at the same side, like

if you're a seller

and chat's like, hey, your
business is worth $6 million.

And when in reality it's not,
it's like,

well,
now you're going to be anchored

to a false idea
of what your business is worth

and you're going to it's
going to be really sad

when offers come in
much lower than that, you know?

And so it's like
on both sides of that, it's

it's a helpful tool.

But I don't know that I would
rely on it.

You still need to have

expert help to,
to look at it to be like,

now here's, here's

where I missed, yeah,
I think a lot of it too

is about asking
the right questions. Right.

And I believe even,

you know, that
that common question of like,

hey, what question am I
not asking that I should be.

Right?

And I think,

you know, for a seller
to utilize that tool

in combined research

with some of our valuation
pieces based on close deals,

like what happens when you push
those closed deals

into their model
that they're suggesting.

Right. That's
that's the interesting part.

Like you can't just

I'm looking at our space and in
particular property management.

And I'd say
our average deal size

is still probably just around
$1 million. Now.

And if a seller comes to us and
wants a comp on a $200,000 deal

or a $3 million deal,
we can provide a comp,

but that's probably
a pretty wide range

for some of the, like,
publicly available information.

From chat.

But yeah, it's interesting
because I'm getting more

and more of that negotiation
through chat from from sellers

than even buyers using that,
you know,

to what they think
is to their advantage. Right?

Yeah.
It's like it's a helpful tool.

But Man one
it's like you picked up

on that immediately
when you saw that you're like,

this is copied
straight from chat.

Like everybody can tell
that's chat, you know.

But I think it's it's
very useful to help guide.

But don't rely wholly on it.

You know what I mean?

Like it's

maybe it'll get there someday,
but it's not there yet.

It's just your starting point.

It's the diving board
to get started, you know.

But I would definitely I would

I would rely more on that than
just googling.

What's my business worth?

You know, I think

I think chat will give you
a better answer than that.

Yeah. And I mean,
I think you and I both

see that quite a bit, right?

Where someone online
may have read that a business

could sell for three
x, for example,

and they maybe don't
quite understand

if that's three x
on gross revenue or on cash flow

or on, but,

and that common misconception
where someone thought, yeah,

they thought their business
that was generating $1 million,

you know, gross
is potentially worth 3 million.

And so it's just not
it's not on gross.

It's on cash flow. It's on Ebit.

There's some value behind the,

you know, gross revenue
multiple.

But cash flow is where we start
Ebit us where we start.

So yeah chat will help you.

You also need
some other resources.

You need other people
to help you as well.

Right.

yeah, that definitely became
apparent on this one where,

you know, they they ask chat
what's this business worth?

And it was like,
oh dude, I wouldn't pay.

I definitely would not pay that
much for this, this business,

you know.

So it's always interesting.

I think most

small business transactions

and maybe I'll insert this
into the chat right now,

but I'm trying to think about

all the transactions
that happen off market.

Right.

Like there's
a lot of these deals

that are closing
not just in the PM space,

but across small businesses
that are purely off market,

that transactional data
isn't going anywhere.

It's,
you know, it's between business

brokers, it's
between attorneys, accountants.

So you know, in such a niche
market like we have,

I'm guessing that maybe
only the larger deals get,

you know, really published
in a way,

maybe more of that information
is available.

But for the majority
of these transactions, like what

we do on an average size
around a million,

how much of that
that close deal,

you know, data is actually
available through chat.

Now. I need to know.

I gotta go
research it right now.

There's not a lot.

It's not like there's

there's a database out there
that you're like, hey,

X amount of companies like, hey,
I want to buy a,

roofing company.

And it's like, okay, what are
what are the multiples on this

That's going to be

tough to go off of
because are they combining?

Are they looking at multiples
of publicly traded companies.

Like what size companies
are they looking at.

Because when you're in the, sub
$5 million range,

it's like that's not
public information.

You know, like it's it's
all I think what's the stat.

It's like 80 or 90% of business
transactions are not on market.

So it's like it's
all just there's

there's not a database for it.

The reason we have a database
is because we do this a lot.

But it's like that's not common.

You know.

Yeah.

I mean,

I think there's probably
a lot of interesting ways to use

AI with the information
that is out there, too,

when it comes to, like, even

preparing your business
to sell or what

what factors might impact value,
which add value

to their business like there's
definitely ways to utilize that.

I'm just trying to understand
too, you know,

what other opportunity
moving forward is there?

You know,

like with our valuation tool
that's been built in-house,

you know,
how can I improve that model?

Right?

I think that's maybe
an interesting discussion.

Just as as it progresses.

How do we take advantage of that
on a larger scale?

And I know you and I
are already looking at

some of those opportunities now.

I think within the next year
it'll be really exciting.

Maybe
that's a little foreboding.

Maybe that's maybe that's
telling people what's coming.

But, I'm thinking I'm
thinking of our New York deal

and thinking about the
what have we learned from that?

We're
working on this deal right now.

We're, Oh, my
gosh, it's been taking forever.

And we finally realized

why the bank keeps coming back
with more questions

and more questions
and more questions.

And then all of a sudden
they're like, oh, by the way,

now we need all updated
documents and financials

because it's been 90 days.

And then we're going to ask
more questions

and more questions
and more questions.

And then all of a sudden we need

updated financials because it's
been another 90 days.

And there's some other factors
in there.

I think the bank is being

acquired by another bank,
and that's really what's

causing them to drag their feet
so much is,

you know, don't rock the boat
during the acquisition.

But regardless,
it was really eye opening

going through that experience
where we were like,

okay,

so this is kind of your
local bank that you're using,

and they are just general
SBA lending.

They don't specialize in
anything versus when we

all of a sudden we switch to
Live Oak, where they have a team

that focuses on property
management acquisitions,

and they get right to it.
They're like, oh yeah, okay.

Yeah, we need X, Y

and Z documents and we can
we can start this.

We could probably get it done
in like 45 days.

And it's really eye
opening to see, like

just because someone says a bank
says that they're an SBA

preferred lender does not mean
they're the right bank

for the deal
you're trying to buy.

There's a lot of people
out there trying to land

on small businesses, right?

I think you and I together

probably get, you know,
a number of emails every week,

but someone else trying to grab
some of this market space,

on the lending side, but,
but yeah,

I think the more and more deals
we work on,

the more appreciative I am to
of working with a bank that,

I mean, if they're waiting for
anything, they're waiting on us,

you know, like we're not
waiting on them hardly ever.

So we need people
at that to push the process.

Obviously the timing. Right.

Like everyone

has heard that, you know, time
kills deals is and,

you know,
working with the lender

that maybe isn't familiar
with this space,

you know, how
that could impact the deal?

I mean, we're looking at that
right now,

right, with this deal.

And luckily we've got a good,
you know, preferred

lender that can step in
and make that happen.

But, you know, those delays
with the bank that maybe

has less experience
in this space,

you know,

on these larger transactions,
I mean, that is an issue.

Right.

But when it comes to lending,

not to dive
super deep into that.

But, you know,
what's our typical process?

Maybe share a little bit
about that as far as like,

you know, we obviously like to
comp this out a little bit too.

And and understand
what other lenders

are out there, maybe something
local in some cases. Right.

Yeah, I'm
totally fine with people

like a buyer saying,

hey, I've already got a great
relationship with my bank.

I want to use them. Awesome.

If you've got
a great relationship

there, that's so much of the

lending process is like,
they have to trust you.

You have to trust them like it's
it really is a partnership.

And,

so it's like if you've got
a good relationship, go for it.

Use them.

As long as they're like, okay,
we understand

this business that you're trying
to buy and how it makes money,

and here's the money
you need to buy this. Great.

Right.

that's kind of ultimately
how it works is just

you need a lender that that can

say they understand you.

They trust your ability.

They do understand
the business that you're buying

and how it makes money.

And and you know, the risks
associated with that.

And they're comfortable
with that

because some banks, it's like

they just
don't have an appetite.

Or maybe they get so many,
so many businesses

that they're trying to land

on so many of these deals

that it's
like they really can be picky

and some are starving

and they're just like,
well, in on anything.

Like we just need something.

And so it's like,
you got to find the right one.

Because we worked on one
in Florida where, yeah,

they wanted
to use their local bank

because they had
a good relationship,

but then they quickly realized
going through the process,

they were like, wait, my bank.

We have a good relationship,

but this bank knows

the business industry really
well that I'm trying to buy.

And I plan on buying more,

and this is going to be
a fruitful partnership

if I build

this relationship here,
even though I've built

this relationship on this side.

So it's like, yeah, not
not all banks are created equal.

So finding the right,
the right one.

Like that's why we tell

we tell people like
talk to 3 or 4 banks, Yeah.

I'm thinking about
one of our buyers

who's out in the Midwest
and has done a number,

you know,
just purely self-funded deals.

And then just within
the last year went through an

SBA backed product through
I'll just mention it up and Lee

Live Oak Bank, who is the group
we're really referring to here.

And it's not a pitch for them
entirely, but I guess it it is

but you know, through that,
that group, through live

oak in their team,

you know, he's been able

to do a number of transactions
all within the last 12 months.

And, and do them quickly. Right.

I think we've seen it
take up to 60 days,

but more recently,
a deal closed in 45.

All of those were over
a million.

One of them.

actually,
I don't know if there was office

space in that
second transaction or not,

but I, I'm curious to know

one of these upcoming deals

that that buyer is doing will
likely include some real estate

as well.

So that's just an interesting
part of of these loans to you.

Is is that something that is
needed for the transaction?

Is that something that the buyer
wants?

Yeah,
a lot of opportunity there.

But also just realizing that
you don't want the bank to be

the one pushing this out,

and you don't want to
lose the deal

with the seller because the
bank's going to take too long.

And, you know,

I think

we've been lucky on that one

you mentioned, but

it's been going on a lot longer
than any of us buyer, seller

and us have thought it would.

But we got the right bank
in there,

and now it's progressing
the way it should have.

Right.

It got to the point
where even the seller was like,

please switch
to this other bank.

Maybe we I just tried like, hey,
we've been working with them

and they've done, you know, x
amount of million with us,

like on other acquisitions
in the last quarter.

And you're just like, oh.

And I was like, yeah,
they understand

this business model.

They understand now
property management

doesn't have a lot of tangible
assets.

It's got a stack of paper

contracts that cash flow,
and they're good with that.

And then they can land on that.

You know they know our process.

So it's

it's like

which is also a really cool
thing about what we do with PMI.

It's like

on the grand scheme of thing,
like our individual franchisees,

they can lean
on the relationship

that we've built with this bank,

because the bank knows
if we bring a deal to them,

they know our process,
they know our success rate.

And it's like they're good.

They know, hey, we could
bring them a deal in Arkansas

or a deal in LA
or in El Paso or wherever.

And they're like,
hey, yeah, we're good to go,

you know, because we've built
that relationship and they know

we're going to make sure
that these businesses close

and there are no defaults.

And, that's that's
kind of a cool thing

because it's like now
these individual franchisees,

they're not the ones that have
to do like 15 deals

and build

a really solid relationship
with the bank because it's like

we've built that in,

you know, through our larger
scale of, hey,

we have like 500 franchisees
trying to buy businesses.

Yeah.

I don't see why Live Oak Bank
wouldn't be a large

part of our $50 million
target in 2026.

I really do think
that a majority of those

loans will go through Live Oak,

and that's
just kind of the appetite

that our network has right
now, right?

I mean, if, like,
we've been scaling up

over the last few years
and now are getting to a point

where we really rely heavily
on these,

these lending partnerships
that we have.

But yeah, it's exciting.

And, you know,
I don't know if that's

I really like working
with Live Oak.

I also suspect that
all the success

they're having
is probably attracting

other lenders as well,
trying to grab part of that.

know, maybe that's a nice,
you know, plug for them.

I don't think anyone else
is providing

the level of service
that they are.

But yeah,
they're a big part of our goal.

And like I said, as a PMI,
you know,

we definitely rely
on those partners because we

we do a lot of the volume.

And you know,
we can't do it alone. Right?

We need the right people
to help us with these deals.

Yeah.

So that that just goes to show
of like

having the right
banking partner is so critical.

If you're trying
to get into acquisitions,

whether you're doing one deal
or $100 million worth of deals,

it's like you gotta find
who the right banking partner

is that that fits what you're
trying to accomplish and that,

you know, a lot of that it
it takes a lot of conversations,

you know,
a lot of launch appointments

or a lot of just activity,
a lot of of experience

working on deals together.

And so it's,

you know, some, some banks,
they're like, hey,

now we specialize in property
management acquisitions

or we specialize

in manufacturing companies,
like whatever it is, you know,

some are just preferred
SBA lenders, which is great.

That means they do a lot of SBA
loan,

but that does not mean
they have a hungry appetite

for the type of business
that you're trying to acquire.

You know?

So just, finding the right
banking partner, it's it's

really important.