In this empowering 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:
– What mentors guide you from employee to founder
– How to identify confining boxes from family and society
– Why self-reflection reveals your true entrepreneurial path
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the start, scale and succeed podcast. It’s the only podcast that grows with you through all seven stages of your journey. As a founder and I’m your host, Scott Ritzheimer, and there’s something that genuinely breaks my heart. As someone who’s helped nearly 20,000 people start their businesses and nonprofits set their very first foot out on the entrepreneurial journey. I can tell you, there’s probably 200 or 300,000 who haven’t and for many of the wrong reasons, folks that are living up to the expectations that someone else laid out for them, living inside these invisible boxes from their parents, their community, their employer and 1000 other places. And that’s just simply, there’s lots of right reasons to not start a business, but that’s not one of them. So here to unpack some of these boxes with us and help us to figure out what I call the dissatisfied employee stage, that pre founder stage of the journey that every successful founder faced at one point in time, is the one and only Betsy Pepine. She is a best selling author, speaker and serial real estate entrepreneur. Her brokerage, Pepine Realty, has been named the ink to the Inc 5000 Fastest Growing Private Companies in the US multiple times, and has earned spots in the top 50 Florida companies to watch and Florida trend Best Companies to Work For lists. Additionally, the Wall Street Journal has consistently recognized her 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 as well. She earned her economics degree from Duke and an MBA from Wharton School of 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 a book out now, and I want to unpack some some pretty cool concepts they have in the book. But you talk about this thing called breaking boxes, these invisible expectations that trap us all. So tell us a little Why did you write the book and for someone who’s sitting there listening now, who maybe has a lot of good things going for them or or maybe doesn’t, but either way, there’s just this dissatisfaction that they can’t shake. What are the boxes that they’re probably living in and can’t see yet?
Betsy Pepine
Thanks, Scott. I wrote the book because I was feeling confined for a long time and just dissatisfied for a long time, and couldn’t figure out the source of my unhappiness. And through a variety of different modalities, I uncovered that all all the points led to this feeling that I was being I related to being like Jim Carrey in The Truman Show. I don’t know if you’ve seen that movie, but you know, obliviously happy, quote, unquote happy, but then growingly discontent, not realizing that his life was being played out on a set orchestrated by others. And that’s what I felt like my life was, and that it was almost like I was this puppet, and not realizing that I was choosing to be controlled by these attitudes, opinions and beliefs of others, or what I thought those attitudes, opinions and beliefs were, and not really following my own true path. And when I started to dismantle those boxes and break out of them, I felt such freedom and aliveness, and when I shared my stories with others, I sensed that they too were stuck and didn’t know how to disentangle themselves from these very real yet non physical boxes that constrain us. So that is why I wrote the book.
Scott Ritzheimer
Yeah, I love that. I want to come back to this idea of very real but because I think that plays out in a whole lot of places, before we get there, though, I do want to dial in on a place where I see it. This happen a lot, and it’s around education, particularly here in the US, how we treat education? What? Let me just start with a question, what boxes do you see, K through 12 and even college put us in, either intentionally or unintentionally?
Betsy Pepine
Well, I mean, I think it’s changed, and I’m a lot older than you. I’m 57 in terms of education growing up. I mean, you definitely, I definitely felt the pressure to check the boxes in terms of, you know, 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 was little, you know, and that was the expectation to succeed, you must have this degree. I do feel like that’s really changed in the last 10 to 20 years, where I see a lot of I see the attitude shifting. I don’t see that, you know, I know when I interview people, regardless of what position in my company, I don’t even look to see if they have a college degree. I am looking only at experience. So I do. Feel like the messaging is changing for our youth in a much better way than the pressure at least that I felt internally to get these certain check boxes checked off so that I would be a candidate for what I wanted to do. Yeah, I don’t know you’re younger. So you may you and your children are younger if you have children. So you may feel that differently, but I definitely feel that that’s it’s moving in the right direction.
Scott Ritzheimer
Yeah, absolutely we’re we’re back in that mode now. My oldest is about to go into high school, and so it’s been a really interesting journey for me these last couple of years, going back to my high school days and just how catastrophically they failed me for anything about adulthood, but and how do we not reproduce this for our kids? But one of the things that happened to me at 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 it didn’t, is actually had a it was a math teacher told me that I was a waste of a beautiful mind and and the question that comes out of this for me is, how do the words of adults when we’re kids shape the adults that we become later in life? How did those words create boxes in and of themselves?
Betsy Pepine
Oh, I mean, they are the boxes. I mean, any you know, when you think about that voice inside your head is, I’m not a psychologist, but I’ve read a lot of books, and they tell you that voice is a is a combination of all of the of the major parental or authoritative figures in your life, including teachers, and so that whatever messaging you the fact that you remember that this many years later, means that that was one of those voices, and that was the the that that teacher had that position in your mind, and so it absolutely directs the path that a child takes and forms beliefs about yourself that you know you can choose to believe or not to Believe, but a lot of children don’t have the wherewithal to understand that that’s just one person’s opinion, right?
Scott Ritzheimer
Absolutely. So one of the things that complicates this, I think, quite a bit, is that many of those boxes have some kind of utility, right? They keep us safe in some way, shape or form. They prevent us from going bankrupt from time to time. But one of the very real areas that these boxes can kind of take root is in our finances, right? And so kind of tying in some of the legacy of education and how that starts to shape us early in our career. One of the obvious ways, like, I mean going through Duke and Wharton at UPenn, you probably have an idea like, it’s not cheap. There are loans that need to be repaid. There’s a very real financial so whether or not someone has has business debt or student debt or just needs to put money, just needs to make enough money to put food on the table, how does the very real need for financial stability, create boxes beyond that need.
Betsy Pepine
I don’t know. I actually think that’s changing too. I’ve seen some pretty resourceful I call them kids because the kids come through my company, and they are, I’ve got children a lot older than them, and they’re they’re very resourceful, and they don’t have to go into a lot of debt. They understand there’s so many resources now that are available to them for free, which shocked me, because growing up, I don’t know if I was just not attuned to that, but I remember one student came in from, you know, she was on fuller scholarship. But I live in a town that’s got a university the state of Florida. University of Florida is here. She’s on full scholarship. And then, you know, she got me as a mentor for free. She was getting coaching, other coaching for free. She was getting her marketing for free. She was just, I was just shocked at how she in her mind, she didn’t have to, she knew she didn’t have to pay for anything if she had the right connections. And I was like, wow, that’s fantastic. So I think, I think that there don’t have to be the boxes that we think there might be right if we assume that there has to be a lot of debt. I don’t know that that’s necessarily true. I think that might be a limiting belief.
Scott Ritzheimer
Yeah. So how do we protect but it’s a great segue into, what do we do with this information? So how do we start to identify what some of these limiting beliefs are, and how do we start to break free of them?
Betsy Pepine
Yeah? I mean, I think anytime you feel a source of discontentment or dissatisfaction, typically what I have learned, and I definitely have 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 if something’s working or not working before your mind will and I came from a very cerebral family, we didn’t talk about emotions and feelings. In fact, if anything, they were discouraged and they were told. We were told it was flighty and unreliable. And you know, what does the science tell you? What do the facts tell you? And then lead with that, but ignore what your body is telling you. And I, I’ve learned to actually do the reverse your body will tell you before your mind can. So that’s your first sign. Is when your body is in getting in touch with your feelings and and where will they lead you? So that’s going to be your first time. And then dissecting what is it that’s making you uncomfortable? Then once you identify the box that you’re that’s no longer serving you, then how do you extricate yourself from that box? And that’s that’s working through what fear. It’s always a fear. What fear is holding you back? Fear of failure, fear of social stigma, fear of loss, fear of financial security there. I mean, there’s so many different fears, but it some fear is holding you back. And so it’s, it’s actually, like you said earlier, boxes serve us. That box, even though, you know it’s no longer serving you. It’s, it is serving you in some way, but it’s probably a detrimental way, but it’s a comfort that almost like a security blanket that you’re not willing to disentangle from. But I encourage everyone write it out on paper. What fear is that anything on paper looks so much less fearful on paper than it does in your mind, where things can just go crazy, but write your fears down. And then I always do an exercise, okay, Betsy, what’s worst case scenario? And worst case scenario is never that bad. Worst case scenario, the outcome doesn’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 it again, and I’ll have learned something so great, a lesson that I get to take with me for the rest of my life. That’s worst case scenario, so that that doesn’t sound that bad once you start working through that process, and then it makes it so much easier to start taking those small steps to get yourself out of a box that’s no longer serving.
Scott Ritzheimer
Yeah, that’s so good. So Betsy, you working in the the realty space? It’s very entrepreneurial industry, right? There’s a pretty big burden 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 lot of create a lot of success, and others who it’s not the right thing. What has that taught you about what it takes to be a successful entrepreneur?
Betsy Pepine
Yeah, unfortunately, in my industry, the bar is really low to get the license, and so it’s just a one week class and the test. And so I think sadly, a lot of people assume that then it must be that easy to make a living in the space, and it’s not the vast majority of real estate is sold by a very small percentage of the realtors out there. And I think with any endeavor that an entrepreneur makes, you have to treat it like a business, especially with entrepreneurship, there’s there is nobody telling you what to do and holding you accountable. So where I people, where I see people fail, is they don’t understand that you really do have to be the manager of yourself. And so some people just their personalities are not cut out for that, and they need accountability from from somebody other than themselves, and they don’t have the discipline and the mindset to make it as an entrepreneur. I mean, you have to, you have to be disciplined in in the plan you have. You also have to be very, very okay with trying and failing. I always say entrepreneurs fail at more things than most people, but that’s what makes them successful. The most successful people, I believe, are entrepreneurs, and they fail the most, but that takes a certain personality to be able to be strong and understand that failure is just a part of the game.
Scott Ritzheimer
Yeah, yeah. So true. I love that. Yeah, you’ve dialed in on two really big points that are just worth reemphasizing, but you’ve got to be willing and able to manage yourself, and you’ve got to be willing and able to fail and get back up again. So so good. Wish more people knew that ahead of time. So, Betsy, there’s this question that I have that I ask all my guests. I’m very interested to see what you have to say. And the question is this, what would you say is the biggest secret that you wish wasn’t a secret at all. What’s that one thing that you wish every founder, or even pre founder, listening today, knew?
Betsy Pepine
Well, there’s so many things, but one on the top of my head would be that you don’t have to go at it alone. You know, I I got a coach about six years into real estate. I wish I had gotten a coach on day one, I didn’t think I needed a coach. I and I still have a coach. I will always have a coach. But in addition, if you can’t afford coaching, although there is free coaching if you, if you can’t do that, there’s always people willing to help you. 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 me to always have both sets, because one is very obtainable. I can see what my next year or two, that what I’m striving for, and then the one that’s 10 years out, and you will be surprised at how many people will help you if you let them know you want to be helped. You know that’s the natural human condition is to help people. And I think there’s so many people that are scared to ask, but the minute you say, You know what, I don’t know it all. I’d love help. People are willing to help you that are above you and further along than you are.
Scott Ritzheimer
That’s powerful. That’s powerful. Betsy, there’s some folks listening 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 you as well.
Betsy Pepine
Sure. Scott, my book is Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us. It’s available on Amazon and all the major book retailers online. I am all over social media with my name. So my website is betsypepine.com there’s a free there’s a free workbook in there, as well as a course that is a corollary to the book. I’m also on all the social media platforms with my name at Betsy Pepine.
Scott Ritzheimer
Fantastic, fantastic. Well, Betsy, thanks so much for being on the show. Really was a privilege and honor. Having you here with us today, for those of you watching and listening, you know your time and attention mean the world to us. I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Contact Betsy Pepine
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/
You can get a copy of her book, Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us, at https://www.amazon.com/Breaking-Boxes-Dismantling-Metaphorical-That-ebook/dp/B0D6CM2JSL/