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November 25, 2025 18 mins

In thisempowering episode, Betsy Pepine, Owner of Pepine Realty, shares how to dismantle invisible boxes and embrace entrepreneurship. If you struggle with dissatisfaction and unseen expectations, you won't want to miss it.

You will discover:

- How to identify confining boxes from family and society

- Why self-reflection reveals your true entrepreneurial path

- What mentors guide you from employee to founder

This episode is ideal for for Founders, Owners, and CEOs in stage 1 of The Founder's Evolution. Not sure which stage you're in? Find out for free in less than 10 minutes at https://www.scalearchitects.com/founders/quiz

Betsy Pepine is a best-selling author, speaker, and serial real estate entrepreneur. Her brokerage, Pepine Realty, has been named to the Inc. 5000 Fastest-Growing Private Companies in the USA multiple times and has earned spots on the Top 50 Florida Companies to Watch and Florida Trend Best Companies to Work For lists. Additionally, the Wall Street Journal has consistently recognized Betsy’s real estate team as one of the top-producing real estate companies in the United States. Betsy also owns a title company, a real estate school, and a property management brokerage. Betsy earned an economics degree from Duke University and an MBA from The Wharton School of Business at the University of Pennsylvania.

Want to learn more about Betsy Pepine's work at Pepine Realty? Check out her website at https://www.pepinerealty.com/

Mentioned in this episode:

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Scott Ritzheimer (00:00):
Hello, hello and welcome. Welcome once again
to the start, scale and succeedpodcast. It's the only podcast
that grows with you through allseven stages of your journey. As
a founder and I'm your host,Scott Ritzheimer, and there's
something that genuinely breaksmy heart. As someone who's
helped nearly 20,000 peoplestart their businesses and
nonprofits set their very firstfoot out on the entrepreneurial

(00:22):
journey. I can tell you, there'sprobably 200 or 300,000 who
haven't and for many of thewrong reasons, folks that are
living up to the expectationsthat someone else laid out for
them, living inside theseinvisible boxes from their
parents, their community, theiremployer and 1000 other places.
And that's just simply, there'slots of right reasons to not

(00:44):
start a business, but that's notone of them. So here to unpack
some of these boxes with us andhelp us to figure out what I
call the dissatisfied employeestage, that pre founder stage of
the journey that everysuccessful founder faced at one
point in time, is the one andonly Betsy Pepine. She is a best

(01:04):
selling author, speaker andserial real estate entrepreneur.
Her brokerage, Pepine Realty,has been named the ink to the
Inc 5000 Fastest Growing PrivateCompanies in the US multiple
times, and has earned spots inthe top 50 Florida companies to
watch and Florida trend BestCompanies to Work For lists.
Additionally, the Wall StreetJournal has consistently

(01:25):
recognized her real estate teamas one of the top producing real
estate companies in the UnitedStates. Betsy also owns a title
company, a real estate schooland a property management
brokerage as well. She earnedher economics degree from Duke
and an MBA from Wharton Schoolof Business and university at
University of Pennsylvania.Well, Betsy, welcome to the
show. So glad to have you here.Let's just start off. You've got

(01:49):
a book out now, and I want tounpack some some pretty cool
concepts they have in the book.But you talk about this thing
called breaking boxes, theseinvisible expectations that trap
us all. So tell us a little Whydid you write the book and for
someone who's sitting therelistening now, who maybe has a
lot of good things going forthem or or maybe doesn't, but
either way, there's just thisdissatisfaction that they can't

(02:11):
shake. What are the boxes thatthey're probably living in and
can't see yet?

Betsy Pepine (02:16):
Thanks, Scott. I wrote the book because I was
feeling confined for a long timeand just dissatisfied for a long
time, and couldn't figure outthe source of my unhappiness.
And through a variety ofdifferent modalities, I
uncovered that all all thepoints led to this feeling that
I was being I related to beinglike Jim Carrey in The Truman

(02:42):
Show. I don't know if you'veseen that movie, but you know,
obliviously happy, quote,unquote happy, but then
growingly discontent, notrealizing that his life was
being played out on a setorchestrated by others. And
that's what I felt like my lifewas, and that it was almost like
I was this puppet, and notrealizing that I was choosing to

(03:07):
be controlled by theseattitudes, opinions and beliefs
of others, or what I thoughtthose attitudes, opinions and
beliefs were, and not reallyfollowing my own true path. And
when I started to dismantlethose boxes and break out of
them, I felt such freedom andaliveness, and when I shared my
stories with others, I sensedthat they too were stuck and

(03:31):
didn't know how to disentanglethemselves from these very real
yet non physical boxes thatconstrain us. So that is why I
wrote the book.

Scott Ritzheimer (03:42):
Yeah, I love that. I want to come back to
this idea of very real butbecause I think that plays out
in a whole lot of places, beforewe get there, though, I do want
to dial in on a place where Isee it. This happen a lot, and
it's around education,particularly here in the US, how
we treat education? What? Let mejust start with a question, what

(04:03):
boxes do you see, K through 12and even college put us in,
either intentionally orunintentionally?

Betsy Pepine (04:13):
Well, I mean, I think it's changed, and I'm a
lot older than you. I'm 57 interms of education growing up. I
mean, you definitely, Idefinitely felt the pressure to
check the boxes in terms of, youknow, there was never a question
of, it wasn't even what college.It was what grad school were you
going to from the time I waslittle, you know, and that was

(04:34):
the expectation to succeed, youmust have this degree. I do feel
like that's really changed inthe last 10 to 20 years, where I
see a lot of I see the attitudeshifting. I don't see that, you
know, I know when I interviewpeople, regardless of what
position in my company, I don'teven look to see if they have a

(04:56):
college degree. I am lookingonly at experience. So I do.
Feel like the messaging ischanging for our youth in a much
better way than the pressure atleast that I felt internally to
get these certain check boxeschecked off so that I would be a
candidate for what I wanted todo. Yeah, I don't know you're

(05:18):
younger. So you may you and yourchildren are younger if you have
children. So you may feel thatdifferently, but I definitely
feel that that's it's moving inthe right direction.

Scott Ritzheimer (05:26):
Yeah, absolutely we're we're back in
that mode now. My oldest isabout to go into high school,
and so it's been a reallyinteresting journey for me these
last couple of years, going backto my high school days and just
how catastrophically they failedme for anything about adulthood,
but and how do we not reproducethis for our kids? But one of

(05:46):
the things that happened to meat school, which I don't want to
say, has had a big impact on me,but I remember it to this day,
and so I'd be lying if I said itdidn't, is actually had a it was
a math teacher told me that Iwas a waste of a beautiful mind
and and the question that comesout of this for me is, how do
the words of adults when we'rekids shape the adults that we

(06:10):
become later in life? How didthose words create boxes in and
of themselves?

Betsy Pepine (06:16):
Oh, I mean, they are the boxes. I mean, any you
know, when you think about thatvoice inside your head is, I'm
not a psychologist, but I'veread a lot of books, and they
tell you that voice is a is acombination of all of the of the
major parental or authoritativefigures in your life, including
teachers, and so that whatevermessaging you the fact that you

(06:39):
remember that this many yearslater, means that that was one
of those voices, and that wasthe the that that teacher had
that position in your mind, andso it absolutely directs the
path that a child takes andforms beliefs about yourself
that you know you can choose tobelieve or not to Believe, but a

(07:01):
lot of children don't have thewherewithal to understand that
that's just one person'sopinion, right?

Scott Ritzheimer (07:06):
Absolutely. So one of the things that
complicates this, I think, quitea bit, is that many of those
boxes have some kind of utility,right? They keep us safe in some
way, shape or form. They preventus from going bankrupt from time
to time. But one of the veryreal areas that these boxes can

(07:28):
kind of take root is in ourfinances, right? And so kind of
tying in some of the legacy ofeducation and how that starts to
shape us early in our career.One of the obvious ways, like, I
mean going through Duke andWharton at UPenn, you probably
have an idea like, it's notcheap. There are loans that need
to be repaid. There's a veryreal financial so whether or not

(07:48):
someone has has business debt orstudent debt or just needs to
put money, just needs to makeenough money to put food on the
table, how does the very realneed for financial stability,
create boxes beyond that need.

Betsy Pepine (08:07):
I don't know. I actually think that's changing
too. I've seen some prettyresourceful I call them kids
because the kids come through mycompany, and they are, I've got
children a lot older than them,and they're they're very
resourceful, and they don't haveto go into a lot of debt. They
understand there's so manyresources now that are available

(08:30):
to them for free, which shockedme, because growing up, I don't
know if I was just not attunedto that, but I remember one
student came in from, you know,she was on fuller scholarship.
But I live in a town that's gota university the state of
Florida. University of Floridais here. She's on full
scholarship. And then, you know,she got me as a mentor for free.
She was getting coaching, othercoaching for free. She was

(08:52):
getting her marketing for free.She was just, I was just shocked
at how she in her mind, shedidn't have to, she knew she
didn't have to pay for anythingif she had the right
connections. And I was like,wow, that's fantastic. So I
think, I think that there don'thave to be the boxes that we
think there might be right if weassume that there has to be a

(09:16):
lot of debt. I don't know thatthat's necessarily true. I think
that might be a limiting belief.

Scott Ritzheimer (09:20):
Yeah. So how do we protect but it's a great
segue into, what do we do withthis information? So how do we
start to identify what some ofthese limiting beliefs are, and
how do we start to break free ofthem?

Betsy Pepine (09:32):
Yeah? I mean, I think anytime you feel a source
of discontentment ordissatisfaction, typically what
I have learned, and I definitelyhave learned this later in life.
I wish I had learned it earlier,but the first sign is in your
body, your body will tell you ifsomething's working or not
working before your mind willand I came from a very cerebral

(09:54):
family, we didn't talk aboutemotions and feelings. In fact,
if anything, they werediscouraged and they were told.
We were told it was flighty andunreliable. And you know, what
does the science tell you? Whatdo the facts tell you? And then
lead with that, but ignore whatyour body is telling you. And I,
I've learned to actually do thereverse your body will tell you
before your mind can. So that'syour first sign. Is when your

(10:18):
body is in getting in touch withyour feelings and and where will
they lead you? So that's goingto be your first time. And then
dissecting what is it that'smaking you uncomfortable? Then
once you identify the box thatyou're that's no longer serving
you, then how do you extricateyourself from that box? And
that's that's working throughwhat fear. It's always a fear.

(10:40):
What fear is holding you back?Fear of failure, fear of social
stigma, fear of loss, fear offinancial security there. I
mean, there's so many differentfears, but it some fear is
holding you back. And so it's,it's actually, like you said
earlier, boxes serve us. Thatbox, even though, you know it's
no longer serving you. It's, itis serving you in some way, but

(11:02):
it's probably a detrimental way,but it's a comfort that almost
like a security blanket thatyou're not willing to
disentangle from. But Iencourage everyone write it out
on paper. What fear is thatanything on paper looks so much
less fearful on paper than itdoes in your mind, where things
can just go crazy, but writeyour fears down. And then I

(11:24):
always do an exercise, okay,Betsy, what's worst case
scenario? And worst casescenario is never that bad.
Worst case scenario, the outcomedoesn't turn out the way I had
hoped, and I have to pivot.Yeah, that's it. I've done that
before, and I'll have to do itagain, and I'll have learned
something so great, a lessonthat I get to take with me for

(11:47):
the rest of my life. That'sworst case scenario, so that
that doesn't sound that bad onceyou start working through that
process, and then it makes it somuch easier to start taking
those small steps to getyourself out of a box that's no
longer serving.

Scott Ritzheimer (12:01):
Yeah, that's so good. So Betsy, you working
in the the realty space? It'svery entrepreneurial industry,
right? There's a pretty bigburden on the individual like,
hey, go out and make it happen.And so you see a lot of folks
who come and go, you see a lotof create a lot of success, and
others who it's not the rightthing. What has that taught you

(12:23):
about what it takes to be asuccessful entrepreneur?

Betsy Pepine (12:27):
Yeah, unfortunately, in my industry,
the bar is really low to get thelicense, and so it's just a one
week class and the test. And soI think sadly, a lot of people
assume that then it must be thateasy to make a living in the
space, and it's not the vastmajority of real estate is sold
by a very small percentage ofthe realtors out there. And I

(12:52):
think with any endeavor that anentrepreneur makes, you have to
treat it like a business,especially with
entrepreneurship, there's thereis nobody telling you what to do
and holding you accountable. Sowhere I people, where I see
people fail, is they don'tunderstand that you really do
have to be the manager ofyourself. And so some people

(13:13):
just their personalities are notcut out for that, and they need
accountability from fromsomebody other than themselves,
and they don't have thediscipline and the mindset to
make it as an entrepreneur. Imean, you have to, you have to
be disciplined in in the planyou have. You also have to be
very, very okay with trying andfailing. I always say

(13:34):
entrepreneurs fail at morethings than most people, but
that's what makes themsuccessful. The most successful
people, I believe, areentrepreneurs, and they fail the
most, but that takes a certainpersonality to be able to be
strong and understand thatfailure is just a part of the
game.

Scott Ritzheimer (13:51):
Yeah, yeah. So true. I love that. Yeah, you've
dialed in on two really bigpoints that are just worth
reemphasizing, but you've got tobe willing and able to manage
yourself, and you've got to bewilling and able to fail and get
back up again. So so good. Wishmore people knew that ahead of
time. So, Betsy, there's thisquestion that I have that I ask

(14:13):
all my guests. I'm veryinterested to see what you have
to say. And the question isthis, what would you say is the
biggest secret that you wishwasn't a secret at all. What's
that one thing that you wishevery founder, or even pre
founder, listening today, knew?

Betsy Pepine (14:26):
Well, there's so many things, but one on the top
of my head would be that youdon't have to go at it alone.
You know, I I got a coach aboutsix years into real estate. I
wish I had gotten a coach on dayone, I didn't think I needed a
coach. I and I still have acoach. I will always have a
coach. But in addition, if youcan't afford coaching, although

(14:48):
there is free coaching if you,if you can't do that, there's
always people willing to helpyou. And I always like people to
identify two types of mentors,the mentor that is just a couple
steps ahead of you, and then.Mentor that is years ahead of
you, and it's important for meto always have both sets,
because one is very obtainable.I can see what my next year or

(15:08):
two, that what I'm striving for,and then the one that's 10 years
out, and you will be surprisedat how many people will help you
if you let them know you want tobe helped. You know that's the
natural human condition is tohelp people. And I think there's
so many people that are scaredto ask, but the minute you say,
You know what, I don't know itall. I'd love help. People are

(15:29):
willing to help you that areabove you and further along than
you are.

Scott Ritzheimer (15:33):
That's powerful. That's powerful.
Betsy, there's some folkslistening who'd love some help
unpacking some of these boxes.And where can they tell us
again, the title of your book,where they can find a book, and
where they can reach out for youas well.

Betsy Pepine (15:47):
Sure. Scott, my book is breaking boxes,
dismantling the metaphoricalboxes that bind us. It's
available on Amazon and all themajor book retailers online. I
am all over social media with myname. So my website is
betsypepine.com there's a freethere's a free workbook in
there, as well as a course thatis a corollary to the book. I'm

(16:07):
also on all the social mediaplatforms with my name at Betsy
Pepine.

Scott Ritzheimer (16:11):
Fantastic, fantastic. Well, Betsy, thanks
so much for being on the show.Really was a privilege and
honor. Having you here with ustoday, for those of you watching
and listening, you know yourtime and attention mean the
world to us. I hope you got asmuch out of this conversation as
I know I did, and I cannot waitto see you next time. Take care.
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