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In this episode of She Is a Leader, host Yvonne Heimann sits down with the inspiring Betsy Pepine. Betsy Pepine is not only a best selling author, speaker, and serial entrepreneur. She is also the founder of Pepine Realty and a powerful example of what intentional leadership looks like when it is rooted in integrity, curiosity, and a genuine desire to uplift others.
From the first few minutes of the conversation, it is clear that Betsy Pepine is not a typical real estate leader. Her journey is filled with sharp pivots, honest introspection, and brave decisions that opened the door to a career that aligns deeply with her values.
Instead of following the traditional version of success that so many feel pressured to pursue, Betsy carved out her own path by putting relationships, trust, vulnerability, and community impact at the center of her work.
This episode explores what shaped Betsy Pepine as a leader, how she approaches mistakes as opportunities, why emotional intelligence is non negotiable in her business, and how her nonprofit and her book Breaking Boxes help others find their own way out of limiting expectations.
If you are craving clarity, connection, and a real look at people driven leadership, the insights from Betsy Pepine will stay with you.
How Betsy Turned a Personal Turning Point Into a New Purpose
Betsy Pepine did not begin her career in real estate. Her early professional life was spent in the pharmaceutical world, where she expected to stay for the long haul. But everything shifted during a period of intense transition. A sudden divorce and a corporate layoff left her navigating life with two young daughters and without the career security she thought she had built.
Instead of holding on to a path that no longer felt meaningful, Betsy Pepine listened to something deeper. She realized she had always felt called to empower others, especially women and children who often face barriers that go unseen. This calling became the anchor for her next chapter.
Real estate became the vehicle for that purpose. Rather than approaching it as a sales centered industry, Betsy Pepine chose to build her business through relationships and service. This mindset laid the foundation for Pepine Realty, now one of the most successful real estate brokerages in Florida.
Why Trust Matters More Than Transactions
For Betsy Pepine, success is not measured by volume or numbers. Her approach begins and ends with trust. She often says, “My goal is to earn your trust. If I earn your trust, the right moment will come when you think of me for real estate support.”
This focus on trust is what shapes Pepine Realty. Betsy Pepine teaches her agents that relationships matter more than any single sale. When people feel cared for, respected, and supported, the business naturally follows. This approach has led to long term clients, a lasting reputation in the community, and a company culture where humans come first.
How Betsy Pepine Uses Vulnerability to Strengthen Her Team
Instead of hiding mistakes, Betsy Pepine brings them into the center of the conversation. Every Tuesday at Pepine Realty is dedicated to “Learnings.” Team members share mistakes, missed steps, or challenges from the week, along with what they learned from the experience.
Betsy Pepine leads the way by sharing her own learnings. This removes shame, encourages honesty, and creates an environment where everyone grows faster because no one has to repeat the same mistake.
As she explains, “If you are not failing, you are not growing.”
Yvonne Heimann adds, “You retrain the perception of a mistake. It is not something bad. It is an opportunity.”
This simple weekly practice demonstrates how vulnerability and transparency can transform a team.
Meditation, Mantras, and the Practice of Being Grounded
One of the most powerful insights shared in the episode is how deeply committed Betsy Pepine is to her own personal development. Her leadership style is rooted in meditation, mantra work, yoga, and self reflection. These practices helped her move away from worrying about outside opinions and toward feeling grounded in her own identity.
“It keeps me grounded and true to who I am,” she says.
This inner steadiness creates emotional safety for her team. When a leader is rooted, confident, and calm, people know they can trust the environment they work in. Betsy Pepine models what it looks like to lead from self awareness rather than from fear.
Collaboration Over Competition
Betsy Pepine brings a refreshing and human centered approach to collaboration. She does not see real estate as a competitive battlefield. She sees it as a place where collaboration creates more value for everyone involved.
She shares stories of receiving systems and strategies from brokers outside her market. She also describes referring a promising agent to another local brokerage because she knew it was a better fit for his goals. This decision strengthened both companies and created trust on all sides.
This is the mindset that has made Betsy Pepine a respected leader in the real estate community.
How to Break Free From Limiting Expectations
Betsy Pepine’s heart for service shows up far beyond her brokerage. She founded Pepine Gives, a nonprofit that partners with Habitat for Humanity to support families facing housing insecurity. Through education and hands on preparation, these families receive the tools they need to succeed as homeowners.
Her book Breaking Boxes continues this mission. In it, Betsy Pepine explores the limiting beliefs and expectations that shape our lives. She shares her own story of growing up in a family that expected her to become a physician and how she chose a different path. The book and the companion course help readers understand their own “boxes” and how to step out of them with clarity and confidence.
Final Thoughts
Betsy Pepine is a powerful example of what leadership looks like when it is guided by intention, self awareness, and compassion. Her story proves that you can build a successful business without losing your humanity. You can lead with trust instead of pressure. You can collaborate instead of compete. You can break out of the boxes that hold you back and help others do the same.
If you feel ready to redefine the way you lead, Betsy Pepine has resources that can help you begin that journey.
Her work is a reminder that leadership becomes transformational when it stays rooted in who you truly are.
Betsy’s Free Toolkit: https://beyondthebox.betsypepine.com/breaking-free-toolkit-opt-in-page
Meet Betsy Pepine
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📄 Video Transcription:
Yvonne Heimann [00:00:01]:
What if your biggest career setback was actually the nudge you needed to unlock your greatest purpose? Today we’re exploring what it really takes to build a mission-driven business in the cut-throat world of real estate, while staying true to your own values. So many face job dissatisfaction, unexpected life changes and the pressure to measure success by someone else’s standards. Add to that the challenges of creating trust in the field known for being transactional, finding ways to lift up the community instead of just chasing profit and breaking out of old family and societal expectation
Betsy Pepine, best selling author, entrepreneur, and founder of Pepine Realty is here to share how she turned personal upheaval into a thriving business and a force for social good. We’ll discuss how Betsy weaves empathy and transparency into leadsership, helps families facing housing insecurity and what breaking out of life’s ‘boxes’ can mean for your own growth. Get ready to feel inspired and challenged to lead differently.
Yvonne Heimann [00:01:13]:
So let me introduce you to Betsy Pepine. She is a best selling author, speaker and serial entrepreneur in the real estate actually. So her brokerage Pepine Realty has been named as an Inc. 5000 fastest growing private company multiple times and has earned spots on the top three 50 Florida companies to watch and Florida Trend Best companies to work for list. The Wall Street Journal has consistently recognized Betsy’s real estate team as a top producing real estate company. Betsy owns a title company, real estate school and property management brokerage. You have been endorsed by her mentor and Shark Tank own speaker Shark however whatever we want to call her Barbara Corcoran. That’s guys we already know this is going to be an amazing episode because Yvi has tongue twisters again.
Not only that, Betsy founded Pepine Gives, a 501c3 non profit foundation that helps family facing housing insecurities and earned an economy degree. Economics degree. Oh my God, my German is coming through today. Somebody saved my tongue from Duke University as well as an MBA from the Wharton School of Business. Betsy, welcome to the episode and welcome to the podcast and welcome to Yvi’s tongue that sometimes just is having way too much fun of her own when the German comes back through.
What a resume, what a amazing journey and what a commitment I have to say I have. I have a perception of the real estate just like some people have a perception of sales, sales guys that sell you the cars. However, fortunately, even though my perception is just a perception, there are people like you, there are people that in real estate don’t just push for sales, people that care about the people they work with, people that care about the people they service. And I’m curious, I already just by the bio can see, see your personality shine through. How did it all come about to be such a multifaceted entrepreneur, to educate, to do the real estate business, to start the 501C3. How did this all come together?
Betsy Pepine [00:04:12]:
So it was not my first career. My first career was in the pharmaceutical industry and I was in marketing in big corporate headquarters in the northeast of the United States and thought I would be doing that for my life. Even though I didn’t enjoy it, I enjoyed what the what the industry provided for me in terms of benefits and work life balance. But when I was 31, 32, I became suddenly and rather unexpectedly divorced with young, very young children and also got laid off from the last pharmaceutical company that I worked for. They laid off the entire commercial division because our product did not get FDA approval. So those two events happening fairly close together and at a pivotal moment in my life when I had one and two year old daughters, I think it just makes you kind of rethink everything, you know, kind of reset and figure out, okay, maybe, maybe universe, God, source is not, is is giving me a sign that I’m not on the right path. Because I wasn’t happy. I wasn’t happy in my job, but I was forsaking that because of the income and everything else the job gave me.
So anyway, so that’s when I pivoted to real estate and I had it not been for those two at the time, I thought unfortunate events which turned out to be the best blessings of my life, I would still be there. But then, but my whole goal in life has always, I’ve always felt from a very young age, this drive to improve and empower the lives of others and especially the marginalized and, and part of that is women and children. And so that, that, that regardless of what I’m doing, that’s always in the back of my mind. That’s always why I exist, that’s why I wake up in the morning. And so when I got into real estate, I do think that one of the reasons that I’ve been so blessed in the industry is because it is not at all a transactional business for me. I’ve always treated it like a relationship business. I, I tell clients and I tell our agents all the time with a hundred percent sincerity. I don’t care if you buy or sell from me.
Betsy Pepine [00:06:30]:
I really don’t. My goal is to earn your trust. I know if I earn your trust, there will be, there will come a point in time where you’re going to real estate services and then you think of me. That’s my only goal, is to earn the trust. And so that’s, that’s been my mindset. That’s what I teach the agents that come and work for us now. And I do think that that’s really helped me in my career. So, so that’s kind of my underlying philosophy.
And then when I started to do well in real estate, I, I did want to serve others. And I thought, well, what better way to serve others than stay in what I know? Like I know and love, you know, I love real estate, but let’s serve a population that won’t. Even though everyone needs real estate services, everyone needs shelter, right? Yeah. But a lot of people can’t use the services through the traditional front door. And so we created this nonprofit and now we have a partnership with an organization called Habitat for humanity. And we help cost burden families get into homes. And it’s truly, it’s what I love about it is it’s a hand up, it’s not a handout. I’m not into handouts.
I’m into, you know, teaching people to fish. And so through habitat and through our partnership, we, we vet them, we make sure that they are teed up. These families are teed up for success. So they have to do programming, educational programming in how to maintain a home. Because a lot of these, a lot of these families are coming from a car. They don’t know how to maintain a home and also how to maintain a family budget because they’ve never had those skills. You know, they weren’t in families that modeled that for them. And so I really feel like it’s a great way for somebody who wants a second chance that’s willing.
They have to, they have to put in 240 hours working on their homes. It’s not, again, it’s not a handout. And they buy the homes now. They buy them and we have great habitats. Wonderful about finding every single program that a homeowner can qualify for to get the rate down, to get the first time home buyer incentives up. But they are still purchasing the home. It is their home. But we’ve teed them up so they have a high probability of success.
Yvonne Heimann [00:08:48]:
And you are in general really intentional about transparency and vulnerability, just sharing financials as well as mistakes with your team. Can you share a story where this approach of transparency and vulnerability and sharing made a significant impact on your team and with that also on a business outcome?
Betsy Pepine [00:09:17]:
Oh, there’s so many because every Tuesday in our, in our, we have a company meeting every Tuesday and we have a section which is my favorite section, which is, we call it Learnings. And it’s, everybody comes and shares what maybe other people would think of as failures, which I don’t believe in failures, believe in learnings. And so they come and they share. We all share what we learned in the last week because of something maybe we forgot to do. You know, we’re all human, we all make mistakes, but let’s not make the same ones. And so by sharing them, we exponentially grow because we’ve now learned from everybody else’s mistakes. So we’re not going to make those. We may make our own, but we’re not going to make those.
And so it’s really become a forum where, you know, sometimes I see agents like vying for who had the best learning, you know, so they’re not. There’s no shame attached to it at all. Because to me, if you’re not failing, you’re not growing, right? You. If you’re not pushing the edges, you’re not growing. And so that’s. That’s just been beautiful to watch. But, I mean, I. I am the first to admit whenever I’ve made a mistake, whether I’ve, you know, even when I was in production, you know, if I.
If I didn’t write, and every agent does this one time or another, they. They forget to write something that’s supposed to convey with the house. You know, maybe it’s a washer and dryer, maybe it’s a refrigerator, maybe it wasn’t supposed to convey, but you put it in, and then the seller’s like, oh, no, I’m taking that with you. And so you. You have to buy that item for the buyer. And so I’ve had to do that, and I’ve had to then say to my team, you know what? I’m an experienced agent still in production, and I made this mistake. And, you know, but here is what I’m doing to make sure that this doesn’t happen to me again. So we share with.
On a weekly basis, we share these mistakes, big and small. I mean, sometimes it’s. We had one the other day. The commission was somehow not negotiated, so the agent did not get paid. And that. That’s something that a lot of agents would be like, oh, my gosh, I hope nobody hears about that. That’s so embarrassing. But it happens, you know, and so what can we.
Yeah, and what can we do then, as a company to help prevent that mistake from happening to our other agents? So it’s a great. To me, it’s a great, safe space for people to share and learn.
Yvonne Heimann [00:11:40]:
And I love how you with your team, pretty much retrain the perception of a mistake. Is something bad or something I should feel ashamed of? Maybe when you do the same mistake twice, three, four times, five times, then we should talk about that. Right? But it’s that. That reframing of. It’s not a mistake, it’s a learning opportunity. And I know that you don’t just do that with your team. And in your everyday life, you lead similar in your mindset, you’re really intentional about meditation and reading and podcasts and. And mantras and yoga and bioenergetic work and all these things.
And I’m curious, how have these practices helped you through challenging times? How have these practices changed how you show up as a leader and how you work.
Betsy Pepine [00:12:45]:
Um, gosh, so immensely. And it’s, it’s been a journey. I wish I had started it when I was 20. You know, I didn’t start that journey until I was, until about 40 when I just was feeling increasingly unhappy. But it, those practices and it’s still a journey. It’s not like I’ve arrived. It’s, you know, I will always be on this journey. But they, those practices keep me so much more grounded and true to who I am.
It’s almost like, you know, you, I’m not nearly as impacted by the, the, the opinions of others, which is really hard in this world. You know, everyone has an opinion about what you do and when you can get out of that and, and really, truly be secure in who you are and know who you are and not being impacted by what others may think of you or perceive of you. That’s very powerful. And I think that gives off a sense of security and safety for those that you lead because it’s like a, it’s, it’s a safety net, you know, instead of a leader. Because I’ve had leaders that haven’t been emotionally intelligent and it’s very disconcerting and you feel very vulnerable when you, when you have a leader like that. And I feel like I’m the opposite of that.
Yvonne Heimann [00:14:10]:
And I think when we do our own work, which through whichever modality and really dig deep into this question of who I am, who do. How do I want to show up, who do I want to be. It also changes our whole energy because suddenly we are now showing up. I don’t want to say perfect but in an energy of knowing, in an energy of I can manage whatever life throws at me. Rather than these fear based closed up.
Where the emotional intelligence isn’t there, where the self recognition isn’t there, where just the energy isn’t there.
Betsy Pepine [00:14:58]:
Yeah. There’s a tremendous sense of peace. Yeah, I agree. I mean it’s a different energy. It’s a confidence that I mean truly. And it doesn’t mean everything goes my way by any means, but it means that. It means that.
Yvonne Heimann [00:15:13]:
I know Universe likes to test us to make sure we are secure in who we are. So let’s just test if you’re really sure in that. Let me throw something at you. We know how she can. But I.
Betsy Pepine [00:15:24]:
Right, right. And. But I, I do feel and I think it’s also just by. I’m 56 now and I think the older we get, the more experiences we have and the more we realize the more we’ve been tested and, and, and come out alive. We know we can handle truly anything that comes our way with grace and will come out all the better for it. Even though we may not understand it at the moment. I have such confidence that this is working for me, not to me. And that helps get through pretty much anything that gets thrown my way.
Yvonne Heimann [00:15:54]:
And that philosophy, you don’t even just keep in, in your business and with your team, you take that hall to a whole new level. Because you mentioned plans to collaborate with competitors, right? I don’t, I don’t live in the real estate, just from an outside view. As I mentioned, I have a perception of the real estate business. There’s a couple of people like you where I’m like, okay, let’s have a conversation here. Stepping into this and saying, you know what, I want to take this out of my team. I want to collaborate with others. I want to exponentially grow the impact we can have, provide more value. And I would love to talk about how you have seen collaborations with “competitors”.
I think we are in the same opinion that there are never ever competitors. How has it benefited not only your business and their business, but also the community? When we get past that perception of fear and somebody is going to take something away from us because they’re in the same industry or in the same location and step away from that fear and actually collaborate. How have you seen that impact your community?
Betsy Pepine [00:17:22]:
Yeah, well, I do, I definitely believe in a mindset of abundance, not scarcity and it’s not a zero sum game. So that’s the mindset I go in with. I’ve seen beautiful collaborations where. And I haven’t. I’ll take that back. So I see it more when you’re collaborating with people not in your, your geographical market. So I’ve, I’ve have had a lot of colleagues in other areas of the country where they have unbelievable success in a certain piece of the real estate business. Maybe it’s the way they lead gen, maybe it’s the way they handle a transaction from, from contract to closing.
Maybe it’s the way they add additional service providers to their portfolio to help their customers. And then they share, they package name, brand and share that their methodology to their competitors. And some of our best systems and processes have come from people in the trenches like me willing to share that with me. So that’s, that’s beautiful. A more local example. Just recently I had a gentleman, I sit on the board with him at a, at a bank and he came to me, told me what his career goals were going to be because he wants to transition slowly out of what he’s doing and be a commercial broker of real estate. We have a commercial. We do commercial real estate.
Betsy Pepine [00:18:55]:
We do residential commercial. We do residential real estate. We do commercial real estate. But listening to what he wanted, yes, I absolutely could have convinced him to come and join us. But I always think that person could be my brother, my uncle, my dad, you know, And I, I’m like, I know in my heart that is not the best. My company is not the best place for him, given what his goals are. So I sent him to a direct competitor two miles down the road. And they were probably shocked because.
And I didn’t say anything. I didn’t know if he was going to say anything. And then I got a night, a very nice text from their broker thanking me very much for sending this gentleman their way. And they ended up hiring him. And I actually had lunch with him a week ago, and he is so happy there. So it’s like, it’s that. It wasn’t like, when I’m that, like I told you at the beginning, I’m not transactional. I’m relational.
And so I definitely earned that gentleman’s trust. I sent him to my competitor to go make a living. Right. Because I knew that’s. That’s what I felt was best for him, not joining my company.
Yvonne Heimann [00:20:01]:
Yeah. And I, I’ve been in. In similar situations where it’s like, yes, we could, but is it the best for you? And sometimes it’s not. And just what we perceive being the right decision. Right. Enough other people wouldn’t react that way. And I also know you are planning or you are working on launching a course and expanding your speaking and growing everything you are offering and how your people, how you are helping people and supporting people.
I’m curious what inspired you to build these new offerings and. And what are the transformations you hope participants experience?
Betsy Pepine [00:20:50]:
So that whole piece is through my. The initiative that’s been generated and the opportunities that’s been generated from the book that I launched last year. And so the book is about a totally different topic. It’s about breaking out of, I call them metaphorical boxes that we find ourselves in throughout our lives. And how my journey through those boxes, through, in and out of them. And, and when I launched that book, I got great feedback. And they’re like, okay, that’s. I loved your examples, but how do I do it for myself? So then that’s why I wrote the course, because the course is more practical on, you know, kind of like workbook style.
And it helps readers and participants engage in their own lives and how they can identify which boxes are holding them back, which, why are they staying in the boxes and how do they extricate themselves out of those? So that’s, and then that’s how the speaking opportunities came to be because people read the book and then they said, oh, will you come and speak at my company? So that’s how that whole. It’s a different business.
Yvonne Heimann [00:21:59]:
We, we always love to just get on a sidewind and my audience is completely used to it because I love the title of the book, Breaking Boxes, where it’s like we get caught up so often in a box, right? It’s, it’s human habits. It’s the same thing over and over again because that’s what our brain thinks is safe for us. So I love the title Breaking Boxes and the idea of building up on it and giving additional resources to it. Now I’m curious, what is one of your big boxes you have broken?
Betsy Pepine [00:22:38]:
Probably the biggest one that impacted my life was everybody’s born in a, in, you know, you’re born into a family, right? And so there’s, there are expectations, beliefs, opinions, just because you’re in that family of origin. So there are, there are boxes relating to your family of origin. In my family of origin, there was tremendous pressure for me and my sisters to be physicians. My dad’s a physician. We grew up working alongside him. He, like I’m doing with these cost burden families, he teed us up to be physicians.
He created the educational piece, he paid for it, he provided the opportunities to work in the hospital. It was, it was on a silver platter for us, but I didn’t want that. And the messaging in my family was that’s the highest level of success. Anything else is a demotion. And so it was very, very difficult for me. When I was in college, my second year of college, I made a call to my parents and told them I was trying to dropping out of pre med and pursuing business. And yeah, you would have thought I had told them I was dropping out of school. I was, you know, now the black sheep of the family.
Betsy Pepine [00:23:56]:
I was, I mean, I was, I mean I felt it whether it was in my head or. They were very disappointed. And you know, they thought that I was lazy. They, they didn’t understand why I wouldn’t want this tremendous gift I was being offered. And honestly it wasn’t until I went back and got My MBA at a reputable school. Did I feel like I had redeemed some level of status back in my family, you know, and so it was just very difficult. And I. But it was a box.
And I couldn’t go through my life being someone I didn’t want to be. And so that was probably the biggest, most difficult box, especially at that age, because I was, what, 18, 19, you know, 20 when I made that decision. That was very difficult. Yeah, so that was probably a big one. But there’s some. I mean, we all face boxes. You know, our gender is a box, our religion’s a box, you know, and they may serve us, but elements of it may not serve us. You know, and maybe it serves us at certain times in our life and it.
At other times it doesn’t. We put other people in boxes, not meaning to, but we do. We do. We make assumptions about people we know. You know, I. I do. I still do it and catch myself. Betsy, you don’t know anything about this person.
Why are you putting them in a box? You know, so, so, yeah, so that’s probably the biggest one. They’re the one that was most impactful to my life.
Yvonne Heimann [00:25:29]:
Now, Betsy, tell my audience, where can they find you and where can they start taking their own boxes down?
Betsy Pepine [00:25:36]:
Sure. So I’m all over the social media at my name, Betsy Pepine. I have a website, betsypepine.com. My book is available there as well as on Amazon and on all the major book retailers online. My course is available on my website. There’s also a free toolkit on my website, BetsyPepine.com for anybody that wants to get started on breaking boxes.
Yvonne Heimann [00:25:59]:
And thank you so much. Thank you for being an inspiration. Thank you for everything you do to give others a leg up and the help to learn to fish themselves. I love the approach you are taking with your 501C3 to not just give handouts, but give hands up. And thank you so much for joining me today and thanks everybody who is listening. You know what’s coming. If you haven’t hit that follow and subscribe button yet, what are you doing? You just met Betsy. There is a huge collection of amazing women in past episodes and in future episodes.
You don’t want to miss out on that. So if you haven’t subscribed yet, go do that. Betsy, thank you so much again for joining me. And bye, everybody.