Episode Transcript
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(00:00):
In today's episode, we'rejoined by four time bestselling author,
speaker and entrepreneur, Ann Lackey.
Ann is the co founder of HireSmart Virtual Employees, a company
that's optimizing remote workby connecting businesses with skilled
virtual assistants.
In the Philippines, herjourney began in real estate where
(00:23):
she and her husband built asuccessful property management business.
Learning valuable lessonsalong the way.
In this episode, Ann sharesthe turning point that led her to
start Hire Smart VirtualEmployees after a personal staffing
issue on a long awaited vacation.
Discover how her innovativeapproach to business has helped countless
(00:44):
companies adapt to remote workeven before the pandemic made it
mainstream.
We'll explore her insights onscaling businesses, the importance
of adaptability, and why shebelieves in investing in mentors
and education.
Plus, Anne discusses theevolving role of AI in her industry
(01:05):
and what's next for her business.
As always, if you found valuefrom this content, please like and
subscribe.
Hello everyone and welcome toanother episode of the Beyond Fulfillment
podcast.
I'm your host Dave Gulas andthis week my guest is the co founder
of Hire Smart VirtualEmployees, Ann Lackey.
(01:25):
Welcome Anne, how are you?
It's good to see you here andgood to meet your audience today.
Thank you for having me.
Yeah, I'm doing fantastic andthank you so much for taking the
time to be here.
We know how busy you are, sowe greatly appreciate it.
My pleasure.
Okay, so as I mentioned, Ann,your co founder of Hire Smart and
we'll get into what thatcompany does here in a minute, but
you've had quite a long andfascinating entrepreneurial journey.
(01:49):
Can you just talk about yourbackstory and how you got here?
Sure.
Well as you said, it's beenlong and varied.
I am kind of started myentrepreneurial journey in real estate.
That's kind of how I kind ofcut my teeth teeth and getting into
business.
And so my husband and Istarted our property management company
for our own rentals back in2002 I think is the the year.
(02:13):
And we started buying rentalproperties because we realized that
corporate America wasn't goingto really do it for our future.
And so we worked two jobs.
I mean basically I workedduring the day, you know, for my
full time job and then we didour side hustle of acquiring rental
properties.
And in 2005 my one of myfriends said you're really good at
(02:35):
this property management stuff.
I see that you're able tocollect your rents.
And she says I need a partnerto manage my clients portfolios.
Would you be willing to.
And I was like okay, so westarted our property management business
in 2005 and grew that pretty well.
I retired from corporate in2009, so I'm working like all the
(02:58):
time during that period of time.
Retired in 2009, still doingreal estate.
Of course, we went through the2008 bubble and rebranded and did
a bunch of different stuffwith that.
And then basically we startedhire smart virtual employees because
I had a marketing manager quitvia text on my first vacation in
(03:20):
seven years.
And so we started looking forwhat are some solutions for employers
to have good people that canwork remotely and save, save money.
So that's kind of how it all started.
And then again, as everythingmy husband and I have ever done,
(03:41):
we had friends and I was like,huh, you've solved this problem.
Can you help me solve it?
And so we started hire smartvirtual employees 10 years ago, helping
other companies have thesolution that we did for ourselves.
Fast forward now into 2025,and here we are helping many, many
clients across the UnitedStates with their staffing problems.
(04:04):
So that's kind of the.
The short version of my verylong, varied past.
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Okay.
All right.
Yeah.
And a whole lot to get into there.
So I appreciate the,Appreciate that overview.
So let's start way back at the beginning.
So you're in corporate America.
(04:46):
You said it's not doing foryou, doing it for you.
And you realize that's notgoing to secure your future.
So you decided to get intoreal estate.
So how, like, how did you getstarted in that process?
Well, that actually is a kindof a story in itself.
So my husband and I were incommission sales.
That's what we did.
We, I worked in IT services.
(05:06):
My husband worked inrelocation services.
And we had a small networkinggroup that would trade leads back
and forth, people that weremoving that needed to relocate, that
type of stuff.
And in that group of 12 peoplethat year, two people ended up getting
cancer.
And one of them subsequently died.
And he was, he was acommission sales rep.
And so we watched him becomefinancially destitute over the year.
(05:29):
Unfortunately, he did pass,and he left a wife with two children.
And there was no, there wasnothing there to support his kids.
And of course, if he wasn'tworking he wasn't making any money.
And so that was a light bulbmoment for us as commission sales
reps.
We realized we're only as goodas what we're able to produce today.
(05:50):
And we needed to figure out away to have money coming in without
us having to work for each andevery dollar.
Which is why we chose rentalreal estate.
It made sense to us.
My family had always haddabbled in real estate, and so it
wasn't unforigned to me, but Ihad a lot to learn.
And so we dove head in.
(06:12):
We bought four properties ourfirst month in the business because
that's the way Mark and I roll.
And we have not looked back.
We still own those properties today.
They're still income producingassets for us.
And we love rental real estate.
We love the flexibility it gives.
We call it mailbox money.
And so we knew that that was away that we could secure our future
(06:35):
that corporate America wouldnever be able to do for us.
Okay, all right.
So you get, you have thatrealization, powerful reminder with
a friend.
And what happened there?
You get started, like yousaid, you dive in headfirst, four
properties right away.
Uh, I'm sure there was alearning curve, right, and, and some,
some mistakes along the way,but you figured it out and got rolling.
(06:59):
Well, we paid professionals.
I think that's one of the things.
So if, you know, we're talkingabout entrepreneurial journeys, one
of the advice I give to peopleis pay people that are smarter than
you to help you figure it out.
Like people that have run thatroad before.
So we, we invested in oureducation, we invested in the right
partners.
We really made sure that wehad at our disposal people that would
(07:22):
come alongside us to help usminimize the mistakes.
We still made plenty ofmistakes, but I feel like we probably
made less mistakes because wewere willing to, you know, partner
with people, invest in them,pay for education, all of the things
that we recommend that people do.
You know, having coaches andmentors is really an important piece.
(07:42):
People that have walked beforeyou to get it done.
So that's one of the pieces ofadvice I would give to someone if
they're starting theirentrepreneurial journey.
Okay, all right.
And so as you mentioned, youwere doing your own property management
and that doing it very well,that a friend realized how good you
were doing and they asked forhelp in their business and thus the
(08:04):
next company was born.
That's correct.
Okay, so going from managingyour own rentals for properties then
to starting a whole propertymanagement company, I mean, what
was that process like?
It Was grueling.
Right?
I mean, when you make mistakeson your own properties, the only
people that you hurt areyourself versus when you are managing
(08:25):
other people.
You have a different level of responsibility.
Now again, because my husbandand I came from corporate, we were
used to policies, procedures,rules, guidelines.
So we brought that into ourproperty management business when
we were working ourselves.
So it wasn't as much of anadjustment when we went and added
other people's, but theaccountability factor was there.
(08:47):
And we, in our first year inthe business business, we added 80
properties to our, to ourmanagement inventory really.
And we learned a ton thatfirst year.
We learned a ton of, you know,what to do, how to screen.
We're pretty good tenantscreeners in, in general.
(09:08):
But again, there are thingsthat you don't know just because
you haven't had the volume of people.
But that year we had a lot of volume.
And so we continue to refineour policies and our procedures and
our guidelines and every.
We have.
And even to this day, anytimewe make a not a mistake, but we do
think that doesn't workexactly the way we want it to work,
(09:28):
we dissect that and we go,okay, where, where would we have
stopped that?
Or where would he have started that?
What would, what was it thatwe can do to mitigate that going
forward?
So we are constantly likelooking basically 360 degrees, like
what do we need to know thatwe didn't know?
What can we incorporate thatto make us better going forward?
(09:51):
We don't look at mistakesmistakes, we look, we look at them
as seminars or educational opportunities.
We always say that like someof our best learning opportunities
were big seminars where weended up writing checks because we
just didn't know what we know.
But we didn't look at it as a failure.
We just looked at it as, okay,well I learned that not going to
do it again.
(10:12):
Okay.
And that's, that's such apowerful mindset for entrepreneurs
because you know, so often.
Right.
Like in the school system weretaught to not make mistakes.
Right.
And that can be verychallenging type of programming to
overcome if you're going into entrepreneurship.
So how did you develop thatmindset to where you really.
(10:32):
I've never heard it put like that.
You view a mistakes as aseminar where you write a check and
you get a valuable lesson.
But like how did you developthat type of mindset towards mistakes?
And I'm not really sure Iremember how we did that.
I just knew that that was kindof what we attributed it to.
Again, we paid for ment wepaid for education, so we were used
(10:53):
to writing texts to help, forpeople to help us.
And so I think, like, I canremember one, one really bad, you
know, rental mistake that wemade when we were buying a property
and selling a property and welooked at each other and we went,
well, it's the cost of a seminar.
And we never made that mistake again.
So I really don't know if, ifit was a conscious like thing, but
(11:16):
that's just kind of what weattributed it to.
And again, it's.
It's usually the things,again, it's things that you don know,
that you don't know is most ofthe time what gets you.
And this was something that wehad never encountered, we had never
thought of.
And so when it happened, wejust kind of looked at each other
and went, that's not good.
But here's what we learned.
(11:37):
And again, now not only dohave we learned it, but we now teach
other people, like, hey, thisis an issue.
You need to be aware of it.
Make sure you don't make thesame mistakes that we make.
So we try to pay it forward topeople as well.
Okay, all right.
So you have the propertymanagement company, like you said,
adding 80 properties in yourfirst year.
So you start scaling and youcontinue to grow that.
(11:58):
And, and then what happened next?
What happened is 2007 and2008, you know, that was the big
real estate bust, right?
It was kind of like musical chairs.
Everything kind of came to a halt.
And so the investors that wewere serving were no longer buying
because they could no longer get.
Get loans.
And so we had to shift, we hadto rebrand, we had to figure out
(12:19):
what are we going to do tomake up the gaps in the income.
Now we still had the portfolioof ourselves, plus we had managed,
we were managing for otherpeople, but at that point, some of
our investors weren't able tokeep up with a mortgage.
And so we had to deal with howdo we, how do we unravel some of
this?
So it was a very difficultlearning curve for us.
(12:41):
And if, you know, me and Mark,we really love people and we love
to do the right thing.
And so, you know, when some ofthese investors weren't paying their
mortgages, and yet I havetenants that I have that are counting
on me for a place to live andthey go into foreclosure.
I mean, that was a reallydifficult time in our business because
(13:01):
they counted on us, right?
And I, I can't, you know, sohaving to navigate that and doing
it in a way that was respectful.
Do you know, to the best of my ability.
Really did kind of help merealize, okay, we're not always in
control.
But what can I control?
What can I do to help this person?
(13:22):
What can I do to.
To make sure that they're okayand treat them with.
With dignity as they deserve?
So a total shift of mind inthat era.
And we then also startedthinking, okay, well, we're no longer
selling homes to investors.
Where else can we sell homes?
So we actually started workingwith more traditional buyers and
(13:44):
sellers, and so we ran a realestate team to help with that.
We did that till about 2013.
And Mark and I realized in2013, we didn't really like working
with traditional buyers and sellers.
That just really wasn't our thing.
We much preferred the investor buyer.
And so we did some othershifts along that as well.
(14:05):
So the lesson in all of thisis don't be afraid to change tax
if things happen.
Like, don't get so set in oneparticular phase of your business
that this is what you're goingto do.
Be able to be fluid and morphand change and then change again.
I mean, if we had to talkabout how many times my husband and
I have rebranded ourselves,it's probably been close to 20 times.
(14:27):
I mean, just different thingsthat we do.
So hopefully that kind ofanswers your question.
Yeah, yeah, absolutely.
And, you know, like you said,not getting set in your ways, being
able to pivot when thesituation calls for it, I mean, that's.
That's powerful.
But the core theme too, itseems, is that regardless if it was
(14:48):
investor buyers, you know,traditional residential buyers, you
still had this expertise inreal estate.
So it sounds like theexperience, you're able to stack
those skills and thatexperience that even when you did
need to pivot within the realestate industry, you still had a.
A high level of expertise.
So I would assume it made thepivot that much easier.
(15:09):
It did, actually.
We got small business of theyear in 2010, believe it or not,
and we were recognized in 2011in our county.
And that's out of all businesses.
That's not just real estate.
I mean, that just shows youthe power of what you can do when
you don't just hide your hidein a hole when things are bad.
But you think about, what do Ineed to do to lift myself up and
(15:31):
how do I.
How do I work?
We were still selling homes,and we did it with no.
No REOs and no foreclosures.
So again, that's the power of mindset.
And being able to say, okay,the world has changed.
How can I change with it?
And what can I do?
What advantages can I adapt?
And you're absolutely right.
My ability and my husband'sability to analyze deals and talk
(15:55):
to a buyer about why this wasa good opportunity for them, or a
seller saying, here's what,here's your net ROI that you're going
to get when you sell wasinstrumental in us being successful
in that area of time.
Okay.
And another question too,something I've noticed as you're
telling this whole story.
(16:15):
So, you know, so often we seethings that, that hold people.
A theme that holds people backis inability to take action.
And entrepreneurs, successfulones in particular, are known to
have a bias for action.
And that certainly seems acentral theme is even when things
were bad, even when youencounter setback, you're will just
go and take the action.
(16:35):
So, I mean, where does thatcome from?
And how, how important do youthink that's been to your, your success?
I think it's extremely important.
And, you know, we, we tend to,if everybody's going left or, or
right, we're going in theopposite direction.
So we typically go against thegrain of whatever is happening, and
(16:56):
we're not afraid to fail.
As we talk about it, it's notfailure if you're not failing in
business in some form orfashion, you' or you're not taking
enough risks.
And so there is an acceptablelevel of risk in any business that
you need to be able to take inorder to have the big wins.
Because here's the thing, ifeverybody's doing everything the
(17:18):
way everybody else is, there'sno differentiating factor.
If you're willing to takerisks when people aren't, that's
where you have an opportunityto shine.
And that's been the way it'sbeen for my whole life.
What makes me that way?
I think I was born that way,quite honestly.
I mean, if you look at kind ofeven before college, I mean, I graduated
(17:39):
college in three and a halfyears with no summer school because
I'm just that kind of a person.
Like, I see what I want and Igo for it.
And I don't really worry aboutthe consequences of it.
I just go.
And so I think part of that isjust part of just who is in my DNA.
For people that are listening,that don't know if that's part of
(18:01):
their DNA, what I would say isit gets easier the more risk you
take and you realize you'renot going to like, totally lose everything
all the time, then you getbetter at being able to assess those
risks and being able to figureout what's your.
What's your threshold.
And my threshold for risk ispretty high, and I've been rewarded
(18:22):
because of that, but it's notin everybody's DNA.
Okay.
All right, so fast forward to2015 and you start another business.
And so often there's a storyor a crisis or just, you know, just
(18:42):
something that's a catalyst towhy a new idea and new business is
formed.
And so you alluded to itearlier when you took your first
vacation in seven years andyour marketing manager quit, and
that was the impetus for thisnext business.
So can you just talk moreabout that?
Yeah.
So, as I said, we ran aproperty management, and my marketing
(19:03):
manager was responsible forposting our listings, taking the
phone calls, setting up theshowings, doing all of that, running
the applications, all of thatfront office type work.
And we drive six hours toOrange beach, which is.
My husband is my.
One of our favorite beaches.
(19:23):
And we get there on a Thursday night.
We wake up on a Fridaymorning, just a little bit later
because we figured we couldsleep in.
We head to our favoritebreakfast place called Duck's Diner.
Hopefully it's still around.
It's been a while since we'vebeen there.
And we literally pull intothe, the, the parking lot, and my
text starts blowing up.
(19:45):
And she says, I'm, I'm leaving.
My keys are on, on the desk,and the remotes are on the desk,
and I'll see you later.
And I was like, what's, why,what's happening?
Could you not have done thisyesterday before I left for six hours,
like, what's happening?
And comes to find out she hada lot of personal challenges and
(20:06):
things like that.
And bless her heart, I, I nowno longer am upset with it, but at
the time, I was really, really angry.
And then my operations manageris calling me saying, why are the
phones not getting answered?
Like, what's happening?
I'm like, she didn't tell youshe left?
She's like, no.
So anyway, we.
We make it through the weekend.
(20:27):
We were supposed to be there a week.
We ended up coming back onSunday morning so that we could kind
of go back to figuring outwhat do we do in this.
This situation.
And what that made me realizeis that we were really vulnerable.
You know, to have one personin the office that had that much
power that literally made mecome back from a week's vacation.
We didn't own a business, weowned a job.
(20:49):
And I was like, we need to fix this.
And so my husband and I hadbeen to a mastermind in the Bahamas
and kind of got introduced tothis concept of full time dedicated
virtual staff from the Philippines.
And we were very curious aboutthat and trying to figure out, okay,
how could we make this work?
And so again, my husband and Iare very good at policies, procedures,
(21:13):
and figuring things out.
And so we said, okay, we'regoing to, we're going to do this
the right way.
We have a staffing partner inthe Philippines that we are exclusive
to them and to us.
So we're doing businesscorrectly in the Philippines, which
is really important to us, andyet we service our clients here in
the US but at that point, Ijust needed somebody to, to help
(21:33):
me with my phones and all of that.
So what the way we startedHire Smart Virtual Employees was
again, we were having a, aconversation with a CEO and she's
literally was 15, 20 minutesinto the conversation and she said,
I timeout.
Like, you're not complainingabout all the staff problems.
And I've never gotten througha lunch without us having this conversation.
(21:57):
So what, what has changed?
And I said, well, I've hired aTeresa from the Philippines and she's
amazing.
She's like, I don't believe you.
I said, what do you mean youdon't believe me?
She said, do you want to talkto her?
She's like, yes, I want totalk to her.
I don't believe you.
So literally, I, I got Teresaon the phone and I said, hi, Teresa,
(22:17):
would you please talk to myfriend Michelle?
And so they had a conversation.
Michelle hangs up the phoneand she says, I need like 5 teresas.
Can you do that for me?
And I said, sure.
And I had not, I had to create it.
She's like, and I want you totrain them and I want you to, to
tell them everything that youneed to know.
(22:38):
And I was like, okay.
So we created ourcertification program, which we still,
we've updated a lot, but westill have the certification piece
to what we do here, whichreally has been the secret sauce
to Secret Sauces for Hire Smart.
And we were able to deliver.
I think we ended up deliveringlike nine virtual employees because
she had a friend that she saysshe needs some too.
(23:00):
So we're going to just haveyou do all of them together.
So I, I created acertification program.
I did the interviewing, I didthe assessments and all the things
that I normally would do as anHR professional.
And I got that her people.
Interesting fun fact.
Teresa still works for mycompany today.
She doesn't work for mepersonally anymore, but she still
works for, for us 10 years later.
(23:23):
I think that speaks a lot towho we are as a company and the type
of people that we attract.
Okay, wow.
All right.
So you have this horriblevacation experience where you realize
you don't own a business, youown a job.
So you set out to fix that andyou find a fantastic solution and
virtual employee from thePhilippines that can really step
(23:45):
in and manage aspects of the business.
And then a friend sees thatand wants the same thing.
And basically that demandturned that turn your solution into
a business.
And again, similar to theproperty management where you weren't
plan, planning this but that,you're, you know, your, your, your
(24:09):
ability got noticed and thusthe demand created a business.
So what was it like this timein terms of not planning?
And then it seems a littlemore complicated too, being that
you're dealing with labor fromother countries and, and all the
other aspects of that.
So what was it like growingthat business?
It's been phenomenal.
It's been a wild ride.
(24:29):
I, I love working and doingthis business.
It's, I mean, I had incorporate, I did a lot of HR and
management and, and so I was,I'm able to bring that into this
business.
This is a much more funbusiness than my property management
business was.
We've since sold the propertymanagement business.
We still have the assets, butwe have somebody else manage the
(24:50):
day to day.
I think, you know, again, forme it's about being open to the possibilities.
And I think again, in yourentrepreneurial journey, what you
need to look at is what's anarea of the market that's not being
served.
Remember, this is way beforeCOVID right?
This is way before people evereven thought about working remotely.
(25:10):
This was, I mean, this was adecade ago.
And so trying to convincepeople that this was a thing in the
early days was hard.
It was hard.
But once they saw the qualityof people that we had, once they
saw the fact that we werereally able to help them.
When Covid did hit, my clientswere rocking and rolling.
(25:33):
It's kept going.
There was no, no pause in theservice they were able to offer because
they were already set up towork remotely.
They were already had theskills to manage remotely.
They already, they were sowell poised to take advantage for
their entrepreneurial journeyinto post Covid world.
Right now that we're postCovid, I no longer have the, the,
(25:57):
the problem of, well, thatcan't be done remotely.
Before COVID it was like, no,I need somebody in the office we
really, we, you can't do thisremote thing.
So Covid was really, reallygood to us and we were poised very,
you know, prominently to takeadvantage of that.
But really the people who wonwere my clients.
They were, they were set, theydidn't have a lot of these, these
(26:19):
the same issues that a lot ofmy non clients at the time had.
Okay, all right.
And so let's talk a little bitmore about Hire Smart.
Are there certain industriesthat you, you specialize in or certain
employee classes?
Yes, we service all kinds.
Everything from breweries tojanitorial services to catering companies.
(26:42):
It doesn't really matter.
But I only do support positions.
So what's a support position?
Right, so administrative work,customer service tasks, accounting
support, things to do withsales support, marketing support.
So there's support roles, sothere's really entry level type roles
where typically us people havea lot of churn because you can't
(27:05):
find, if you can find somebodyto fill it, they're not going to
stay there more than sixmonths because they're going to use
that job to hop to something else.
Whereas my people stick aroundfor a very long time.
We pay them very well.
We have full time benefits, wehave dental benefits.
We're rolling out a retirementplan this year that they can, the
clients can opt into for lessthan $22 a pie pay period per person.
(27:28):
And yet it has a huge impacton their, the stickiness and being
able to have people thatagain, really invested in our clients
mission.
So all of that I think, youknow, really kind of makes the difference
if that makes sense to you.
Okay.
All right.
And so as you mentioned, we'rehere in 2025, right.
(27:50):
And you've got exciting plans,you know, like you said, with the
growth of Hire Smart and thenso what, what's next for that business?
Well, I think, you know,really where what's next is.
Obviously we have a lot ofconversations around AI and people
think AI is going to take outall my business.
It's, it's not.
People still like to deal withhumans, but we're looking at AI and
(28:14):
how do we incorporate AI intoour certification class?
How do we make sure that we'vegot people that understand AI and
use it appropriately?
We're looking at what rolesare more AI proof than others.
So I think, you know, I thinkthe first kind of bite out of our
business is going to beaccounting because I think accounting
(28:36):
lends itself to AI fairly easily.
But some of the other thingslike that we offer, like receptionist
people don't want to Talk to a bot.
People want to talk to a person.
I think customer service, Ithink will change up the level of
customer service.
So, so AI will deal with kindof the routine, kind of run of the
mil FAQ questions and then mypeople will step in when it gets
(28:58):
kicked up above that.
I think, you know, what weoffer for executive admin, that's
not going to be replaced by AIbecause people want to have a relationship
with their executive adminbecause it's an extension of the
CEO.
And I think that's going to besomething that we focus a lot of
our attention and training andcertification on.
I think, again, sales supportis another one.
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People like to talk to peoplewhen they're buying us or selling
a service.
And so those are, those aresome of the things that I think we're
going to continue to mature,use AI as a tool, and yet really
be able to take it to the nextlevel for, for our clients.
Okay.
All right.
And if people want to get intouch and learn more about Hire Smart
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and how, how they canpotentially work with you, what's
the best way that people canreach out to you?
Well, if people want toschedule a call with me, the easiest
way is meet with an dot com.
That's the way to get on my schedule.
If you're curious about theservices that we provide, it's hire
smart virtualemployees.com andthey can check us out.
We have lots of resources,lots of good educational tools in
(30:03):
our resource page to encouragepeople to do that.
And of course, we're on socialmedia as well.
Okay, excellent.
And we'll link all that in theshow notes for everyone.
Well, and thank you so muchfor taking the time to be here, sharing
all this valuable wisdom fromyour journey and all these insights
for the audience.
We greatly appreciate,appreciate it.
It's been my pleasure, Dave.
Thank you for having me.
And again, I hope to helpanybody that's listening in any way
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that I possibly can.
All right, and that is all thetime we have for now.
We will see you next time.