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“Just because we're younger doesn't mean that we have any less leadership skills.”“Leaders today just...are lacking a lot of maybe foresight in what our younger generations are kind of going through.”“If I'm gonna lead, I am gonna lead my people through action.”“Trust yourself a little bit more. You have what it takes to be in this role. You wouldn't be here if you didn't.”“They were smart enough to know I did need to be there.”“The how usually is a way, but people let that how keep them stuck.”“It doesn't need to be perfect. I just need to start.”“Staying still and stagnant and not growing and learning is so much scarier than just trying and maybe failing.”
Rooted & Relentless is the business strategy podcast for entrepreneurs building service-based businesses designed to grow, adapt, and last. Business strategist Steph Rubio shares practical guidance on a range of topics meant to help you sell, scale, and stabilize.
Think sustainable business growth, revenue strategy, systems, capacity, client experience, and the founder leadership required to turn your skills into a successful, sustainable company.
Steph Rubio (00:00.076)
Up, party people. Welcome back to another episode of your favorite podcast, mostly about business, a lot about life, where we get weird and silly, but keep it super duper real. Today is an extra special episode. I have my friend, business buddy, mastermind member, local person here. I've actually met in person, which is rare I get to say that online. Caelyn, it's Kaylin, when do we get to know each other? It's been almost like a year and a half now, probably, that we.
Caelyn Zupko (00:27.986)
Yeah, I think so.
Steph Rubio (00:29.11)
met for the first time. Welcome to Rooted in Relentless.
Caelyn Zupko (00:32.17)
Thank you for having me. I am so excited to be here.
Steph Rubio (00:34.634)
Yeah, I'm so excited to chat. We've obviously got to do a lot of that and like our work together over the past several months, but this is different when I get to interview you and like let your expertise shine. Before we do that and get into the real fun, let's tell people a little bit about who you are, which we could probably never sum up in a 30-minute episode, but we'll do our best. You are a top producing realtor, turned personal branding and content strategy expert.
Caelyn Zupko (00:55.1)
Yeah.
Steph Rubio (01:01.944)
Who helps other realtors become local celebrities by leveraging real content, which we're all aching for these days? If you look around anywhere, everyone's like, be yourself and be authentic, finally. Thanks to the AI slot. So seeing kind of lead that charge with realtors has been such a joy. I also know that you're a speaker and an award-winning culture and community builder. Anything you want to add to that?
Caelyn Zupko (01:28.263)
Wow, I mean you really just fluffed me right up. no, I think you really hit the nail on the head. Yeah, I love really embracing the cringe online and just being real and authentic and getting rid of that AI slop and teaching other people how to do it too.
Steph Rubio (01:31.458)
Yeah.
Steph Rubio (01:42.476)
Yeah, yeah, and it's important now more than ever. It's really like crazy that being yourself is the the hard concept these days.
Caelyn Zupko (01:45.342)
Yeah.
Caelyn Zupko (01:50.212)
Right. Like people they don't know what to do with it. They're like, You want me to be real and you don't want me to use this like scripted out content that's perfect and polished. No, no, no, no. I want you to like be a person and like make mistakes and show me you.
Steph Rubio (02:04.053)
Yeah, yeah. And I find it fascinating too. I won't steer us too crazy, but like that this is what happens with marketing. You know what I mean? When something goes really far and I see it online more than like any other marketing is like because everyone is like a school of fish comes over here. Well then you get those people that are sick of that suddenly. And that's kind of what we're in now. You got the we all did that and there were scripts and there were frameworks and there were beat the algorithms and then suddenly it was like we were all really sick of that. So I think leaning into it is like
Caelyn Zupko (02:07.686)
Yeah.
Caelyn Zupko (02:24.434)
Yeah.
Caelyn Zupko (02:28.678)
Yeah.
Steph Rubio (02:31.135)
It's a joy. It's a joy to be able to market your business and make money by being yourself and seeing you do that.
Caelyn Zupko (02:32.476)
Yeah.
Caelyn Zupko (02:39.547)
I mean, I mean it makes it so much easier too. Like you get to really, like you said, enjoy it and it comes so much more effortlessly when you just kind of like take what you're already doing in life and put it online, as opposed to like having to be super structured and like stressing so much over my god, did I say the right thing? Do I look the right way? Like it just it burns you out so much quicker on social media and then people go, Okay, I'm not gonna do it anymore 'cause it's too hard. But like you don't need to do that at all.
Steph Rubio (03:01.099)
Yeah. Yeah. Perfect for me. Someone like I've shown up on years with like for years online with like wet hair. I'm like, I don't really want to try my hair. So this is perfect. Thanks. This is my time. What a time to be alive. That's what I've said. Like, why are we hiding from this? This is awesome. Okay. We'll probably get back to some of that, like what you're doing these days, but I want to take it back a bit because I've been doing this for a little while and I'm constantly watching like gaps, or I'm I'm just always fascinated by why anyway.
Caelyn Zupko (03:08.366)
Yeah. Yep.
Steph Rubio (03:30.732)
So when I hear consistent like angster problems and in people I support, I'm always like, wow, why is this an issue? And I have found that across the industry, just about like online and our online space and running businesses, there is a serious lack of just leadership. So I have many thoughts there. And you and I have been talking a bit about young leadership. You have in particular. So I want to spend some time there, really. And when we talk about young leadership.
Caelyn Zupko (03:30.969)
Mm-hmm.
Steph Rubio (03:58.86)
I just want to hear from you. Like what do you mean by that?
Caelyn Zupko (04:02.577)
So I think younger leadership is interesting, right? I started out working at 16. Like the second I could get a job, I got a job. And like by the time I was 18, I was an assistant manager, right? Like I was working my way up corporate ladders.
I was stepping into these leadership roles that I didn't really know at the time were like setting me up for these things. Like I just was working and like had a really I have a really strong work ethic and I like to go above and beyond like big big people pleaser here. so I really just, you know, like naturally stepped into those roles. And I think that that's something that isn't really talked about. And also it's something that is sort of taboo in a way.
Because I think there's a common misconception that, like, you're young, you don't have the experience, you don't have what it takes to actually be a leader. But leaders today just I think especially like older generations are lacking a lot of maybe foresight in what our younger generations are kind of going through, the changes that we're seeing, especially when you come into the online space. You know, I think a lot of people are very much so stuck in the old ways. And
They're not really willing to listen to younger leaders when we have so many thoughts and ideas and like the way that we're being raised is really changing the way that we're coming up into leadership. So I think it's an important conversation to have because just because we're younger doesn't mean that we have any less leadership skills. Like, you know, again, I spent 40, 50, 60 hours a week working in these leadership positions that really put me ahead of some of my peers who were.
double, triple my age that were were working underneath me and they didn't like working underneath me simply because I was younger than them. But I had developed the skills that it took to run multi-million dollar businesses. So I think there's a lot to learn in like stepping back and kind of listening to younger leaders because we might have a thing or two to say.
Steph Rubio (05:54.881)
Yeah.
Steph Rubio (06:03.681)
So here's the interesting part of that is that leadership, period, there should be a big component of listening anyways. And I think that's where people get it wrong. So what you're saying to me is just a part of leadership. Like to me, that's a part of the job. You know, and I I don't think of leadership necessarily as a job. The interesting part is over my time, like why I'm so passionate about leadership is because I have
Caelyn Zupko (06:12.332)
Mm-hmm.
Caelyn Zupko (06:20.193)
Right.
Steph Rubio (06:29.985)
Well, I studied it. I studied theories of leadership a couple of years ago and I learned a lot from that. Like, I mean, we love a good theory, right? Anyway, it's like we can't prove this. We'll just talk about all these things. But really focusing on like and one thing I know to be true and have witnessed is there are leaders in title and name, right? And there are leaders in practice. And theories of leadership really brings that there are leaders and followers. Like you're either one or the other, right? You're a leader or a follower. And it does play on that. Like it's not managers, that's different.
Right. Because you can be a manager and not be a leader. And so that's what that differentiator is to me. So I find it fascinating that you're like, I think that if leaders like older leaders could listen to younger leaders. Well, if they're not, then they're not actually a leader. They're just a leader in title to me. And I've seen this miss a lot. And it's like not going to shock people that a lot of this comes from the traditional leadership of businesses that have traditionally been white men and typically older white men because you had to climb, climb, climb, climb to get there, right?
Caelyn Zupko (06:58.966)
Absolutely.
Caelyn Zupko (07:24.662)
Mm-hmm.
Steph Rubio (07:28.671)
And so that's just been perpetuated that you can be a manager, that you can climb this ladder, but then you can sit there at the top disconnected from the people that you're even supposed to be leading and making decisions like in silos. And I've just seen it be extremely harmful. Or I've seen these same people sit at a leadership table and struggle to make difficult decisions with the data in front of them instead of making like the emotional ones and funny. Again, it was
Men when women are apparently the emotional ones. And we're the one over here, like, no, no, no, this is what the data's telling us and what we should do to make money. I see some synergies too. And like Caleb, it's funny because when we started working together, obviously, like what we're doing doesn't have much to do specifically with young leadership, has a lot to do with what you're doing with your social media and stuff. So some of this I didn't even know, like you being a GM at 22 and the synergies in our own stories, because I became a district manager over four sales stores at 25.
Caelyn Zupko (07:57.781)
No, right.
Steph Rubio (08:25.073)
well I say that and then I'm like, Well, for a week because I walked away. I said no, thank you. Like I took it out of flattery and I was a single mom at the time, freshly single mother. And so I was like honored, flattered, and when I saw the pay come through, like when we started the pay, I was like, nah girl, because I was gonna be gone too much. I was gonna be traveling to stores and staying overnight in hotels away from my infant son at the time.
Caelyn Zupko (08:31.294)
Yeah.
Caelyn Zupko (08:44.245)
Yeah.
Steph Rubio (08:52.117)
Which I agreed to do. Had the money been different, that would change our situation. And I might have done that for a while. But anywho, same. I mean, I guess we could debate like is twenty-five young looks young, but to lead four sell stores, yeah. I think so. So what makes a leader, in my opinion, and what I've seen is not age. it is absolutely skill sets. And leadership is leading yourself, it's also leading others.
Caelyn Zupko (09:05.765)
Yeah, absolutely.
Steph Rubio (09:19.623)
And I think to lead others you have to lead yourself, which sounds like probably some of why you landed there. You're also a old eldest daughter, right? Yes. You've been leading your whole life. I mean, come on.
Caelyn Zupko (09:27.355)
I am an eldest daughter. Mm-hmm. Yeah, no, that ticks all the boxes, honestly. Like it make when you hear how my progression happened, you're like, you're an eldest daughter? That makes sense.
Steph Rubio (09:39.147)
Yeah. So when you when you think back on that time, like you became a GM at twenty two, I'm curious what had you already done at that point that made you qualified for the role, right? Their version of qualified, 'cause someone saw you as qualified to take it, even if other people couldn't see past your age.
Caelyn Zupko (09:55.536)
Yeah. So, long story short, I had sort of like out of high school, I went to college for a year. Mm moving happened. We moved down the east coast to Virginia. and I just didn't continue at the same college. I didn't want to have to commute back and forth, like travel all those things. and I kind of was like, I don't really know what I want to do with my life. I'm a little bit lost. I was nineteen or twenty at the time. So I joined I started a part time retail career.
And like very quickly, like from my interview, they were like, okay, we're gonna start you out as a sales associate, but like we're kind of like fast tracking you into this like sort of part-time leadership position. and it built from there. So I had just always been somebody who was like an overachiever, like, you know, let me underpromise, overdeliver. And I was always just somebody who was really outgoing and like working really, really hard, staying longer than I needed to, covering shifts, stepping into leadership roles without even really realizing it, you know. So by the time
We PCS to Florida in 2021. I had worked in like full-time assistant management roles and was working an hour away. And I was like, okay, this is too much. So I ended up working in a new field, like career field. I went from clothing retail to beauty and makeup. So not even like three months in, my GM promoted to a bigger store. So we had no general manager for a little while and I was sitting there.
Steph Rubio (11:10.369)
Okay.
Caelyn Zupko (11:22.158)
And you know, she calls me one day and she was like, Have you have you ever thought about being a general manager? And I was like, Yeah, like it's my dream. I want to climb the corporate road or I would love to be in district management one day. so yeah, I mean, I'm interested. And she was like, Okay, well, do you want the store? And I was like, Huh? Huh? I thought this was like years down the road development wise, because I had just started with this new company, right? I was like, nobody really knows my skill set. but she and my district manager had talked separately and they were like, Yeah, you like you're the perfect candidate.
Steph Rubio (11:44.033)
Yeah, well.
Caelyn Zupko (11:50.084)
The store is a smaller volume store. I mean, still multi-million dollar a year store, right? But smaller stores, so great for growth and development. So I was sort of I don't want to say handed the position because like I did work my ass off for it, right? Like I had the leadership skills, the development, but it sort of fell into my lap where it was like I wasn't expecting this for years to come. I was expecting to have a lot more development. But at the ripe old age of 22 years old, I was given the keys to my own store. and it was
Steph Rubio (11:54.839)
Yeah.
Caelyn Zupko (12:17.973)
life changing in a lot of ways because I at the time like that was my dream, right? I wanted to develop my own team. I really wanted to show that like I was capable of doing this and in a lot of ways I did. I just I took the store and ran with it and like culture was my number one pillar. Yeah, we actually got recognized for our culture specifically and I've won other culture awards since then because I said, okay, I if I'm gonna lead, I am gonna lead my people through action and making sure that everybody feels like this is a place where they can come.
Steph Rubio (12:22.603)
Yeah.
Steph Rubio (12:37.293)
Yeah.
Caelyn Zupko (12:45.516)
And not only work, because that's your main goal, right? Work to make money for the company, but at the same time, like I want it to feel like a culture where people enjoy coming to work, they enjoy working for me and for this company, and they have a growth and development path. So, and I think that that's something undervalued again in the older leadership and management space where it's sort of okay, I manage the day-to-day operations in the store and that's all I'm gonna give to it, where I was like, No, where can I take this in?
Steph Rubio (12:59.661)
Yeah.
Yeah.
Caelyn Zupko (13:13.431)
five, ten, fifteen years and how can I make this a better place?
Steph Rubio (13:17.131)
Yeah, long term. I mean, obviously you're a leader. Like we're this is what the c topic is about. So I'll have to tell you that, but there's so many things standing out that I I bet you maybe didn't necessarily recognize then and hopefully do now. But well, a lot of people don't realize unless they are leading and truly leading is that like you mentioned, you know, yeah, we know people come to work to make money, truly. At the end of the day, like that's what we're doing. but you want it to be a place they want to come to. Well, there's a strategic trade off to that.
Caelyn Zupko (13:18.945)
Yeah.
Steph Rubio (13:45.036)
Because when you make it a place that people actually want to come to work. Like, yes, we want to make the money. So the money's a big part, benefits are a big part, right? Like make it money they want to come for. But the better the workplace and the more excited and the more belonging they want to come. And the money now they want to stick around, which means you're retaining talent. And the strategic trade offs of retaining talent, like you've heard me talk about before on stage, but the benefits to your business are one,
Retaining talent is more cost effective for your business than hiring new talent because, well, flatly, you are not spending time and man hours interviewing, interviewing, interviewing and training new people. And we're not constantly training new people. When you're keeping people around, then they reserve that institutional knowledge. If you think about just a server that you trained to know the menu, to deliver the food, to give good service, right? And then you have to do that again. That's wasted money.
That's harming your business. So it's actually better for your profitability, for your margin, for the bottom line of your business. again, good leaders know this to create a good place that people want to come to. And this is absolutely applicable in our online space with people who are hiring freelancers or hiring contractors, maybe not full teammates. So if you do teammates, it's the same thing. If you hire out a job one time, like it still applies that the better experience you give them has a trade-off that
Caelyn Zupko (14:59.5)
Mm-hmm.
Steph Rubio (15:07.493)
sometimes you don't even realize unless you're looking at this depth because when they have a great experience with you and they see that inside of your business and they see how you are behind the scenes, they will now go forth and carry your brand too and your reputation. So you, I think maybe we're leading even more advanced than you realized at the time, but people above you too hopefully realize that.
Caelyn Zupko (15:29.471)
Yeah, I mean we had the highest retention rate in our district. We had the highest culture rate in our district. It was something that I was super excited about. You know, we might not have always hit our numbers. Little baby store was hard, especially after my first year, because in my first year we blew everything out of the water. And then my second year, I was like, okay, it's hard to cap this, right? But I mean, I think the honestly, I think that culture and those retention and those other metrics are sometimes more important than the bottom line, like profitability, because it's the longevity of the brand, right?
Steph Rubio (15:37.621)
Yeah. Yeah.
Caelyn Zupko (15:58.452)
you're not having to start over and start over and start over. You're continuing a legacy that's been built and you can really grow stronger as a I'll call it a community that way. Because I mean it was at the end of the day, it was a a a community of employees who all enjoyed working together. They all enjoyed coming to work and doing the work that was necessary to grow this huge corporation.
Steph Rubio (15:58.552)
Yeah.
Steph Rubio (16:18.081)
Yeah. Well it's but it is part of your profitability at the end of the day. If like you're looking at revenue, right? When you're saying hitting your numbers like your revenue, that's the money you're bringing in. Yes, right. So maybe other stores were hitting that and you weren't, but that's not the end of the story. There are tons of line items after that that bring you down to profitability. So if you're having turnover and you're retraining, that's a part of it. So you were just as or equally as successful in many ways where other people might be missing that mark. So yes, they could
Caelyn Zupko (16:23.879)
Well.
Steph Rubio (16:46.798)
sell, yes, they could make money, but location plays into that when you're talking retail stores. You know what I mean? Like there are things out of your control there, certainly. I'm curious yeah but
Caelyn Zupko (16:51.654)
Yeah.
Well, and it's funny, go ahead. I think the other point too is that, you know, that was really the reason that it was one of the key reasons that separated me from retail at the end was that it just became a shift from, okay, you're doing all these great things in the store, but now like bottom line is the most important thing. How much money are you making? Are you reducing shrink to like, you know, theft and things like that? And like how much more are you making above your goal? And it was just
Make more money, make more money, make more money. And there was no more emphasis on, okay, like there's other things that you're building outside of our bottom line. And that for me was just my breaking point where it was like, it doesn't matter how much I do, you want more out of me, I'm done.
Steph Rubio (17:37.302)
Yeah. Yeah. I mean, I saw this like again, like similarities there, but completely different company and cut kind of context. And why, like you've heard me say, I've removed myself from corporations because I got sick of basically being like rendered ineffective. Because a lot of people think, and I see this in our space, you need more money, and everybody thinks that's selling and revenue. Well, sometimes you can just find money in what you're already doing. And so sitting in rooms like that where you're looking at tons of data and numbers and
Caelyn Zupko (17:47.495)
Mm-hmm.
Caelyn Zupko (17:56.624)
Yes.
Steph Rubio (18:06.605)
planning for businesses ahead and where to put time, money, and resources. And you'd have some of this, some of us that were like, okay, this is a startup business, but we're in like year six, seven, eight, right? So not brand new business, still startup in the tech world and stuff like that. But the hodgepodge of systems and stuff like that that you have works for a while until it doesn't. So when you you're looking at like we need more money, what a board wants is the company to be profitable.
Caelyn Zupko (18:32.665)
Mm-hmm.
Steph Rubio (18:34.305)
But then you sit there with ineffective leaders and they're like, well, that means sell more. I need this salesperson. We got to keep that salesperson around because we need sales and they're doing a crap job. Now, when what we were trying to look at is full picture and we're begging them to make operational efficiencies one of the key metrics, right? One of the key priorities for the coming year or something like that. And we're talking like
Caelyn Zupko (18:51.322)
Yes.
Steph Rubio (18:57.739)
Making our hiring process more streamlined. All of those efficiencies you realize in there, now you're spending less manpower money, right? On all of these. Let's how are we looking at our sales process? How are we looking at what we're logging in the system so we don't let those sales go cold? Like all of these operational components just continuously, and I see this all the time, felt like
They weren't priority because money was priority. Well, there's money everywhere. It's not just in your sales. And some people miss that. And I know I know it can be difficult because it's like, well, I can just sell and make money. Okay. But you can also upsell to people you currently have. You can also keep those people around instead of re new ones. Like, I mean, I love this. So let me not get us too far off the rails. I still want to talk just a little bit about the leadership. When you think about like
Caelyn Zupko (19:22.628)
Yeah.
Steph Rubio (19:43.884)
You mentioned at one point there that like you had people, you know, under you for lack of better words, that you were leading and managing that were older than you and probably weren't crazy about the idea. when people were doubting you or questioning you, even if they didn't out loud about like if you were old enough or experienced enough, did that make you doubt yourself or did it make you more determined to prove them wrong? Actually, I guess that doesn't have to be an or, it could be an and. And did it make you want to prove yourself?
Caelyn Zupko (20:06.616)
Ha ha ha.
Think it it is definitely an and and I will say too, like I am my own worst enemy. Again, eldest daughter here, hello. I have very, very high expectations of myself. So even going in, I was like, I literally said about this district manager. I was like, hey, so you know I'm only 22, right? I don't have like this crazy experience. Like you are aware of this, correct? And she was like, Yes, yeah, I I am in fact aware. So I think that it that was probably my own biggest issue or you know.
Steph Rubio (20:16.716)
Yeah.
Steph Rubio (20:28.695)
Yeah.
Caelyn Zupko (20:36.947)
in my entire experience there was that I held myself back a little bit because I was like, my God, what are they gonna think based on my age? What are they gonna think based on like their perceived lack of my experience? But at the same time, like I did have some older women underneath, like direct reports to me who were not only just not happy that I was their boss, but like did some things to go out of their way to try to get me in trouble or get me fired. And it was very frustrating because it was like, what are we in high school? And I g I'm the one saying this to you. That's hard.
Steph Rubio (20:46.829)
Yeah.
Caelyn Zupko (21:06.93)
And it was also just incredibly hard to coach them too because you can only give them so much without trying right, they don't want it. And then they it creates friction because they're like, Well, I'm older than you and I know more and that's like you can only go so far with that without going upper level coaching. So it was like there were definitely some barriers to execution there as far as my own self-doubt and then the self-doubt of some fears, but I did like you know, I through actions, again, like proof them wrong.
Steph Rubio (21:11.58)
they don't want it. Yeah, they don't want it. Yeah.
Steph Rubio (21:20.535)
Yeah.
Caelyn Zupko (21:33.834)
I was able to show like, no, I am very capable of leading this company. I am very capable of running this store the way that my district manager expected me to. And we blew it away time and time again in our sales results, in our culture, in our retention, in our, you know, things like our loss prevention audits and other audits and things like I was like, you may think this way, but here is the data to show that I am undeniably fit for this job. And if you don't like that, you can leave. The door is there.
Steph Rubio (21:59.936)
Yeah. Yep. You can roll out one thing I I just found fascinating about what you said is like you almost doubted yourself out of the role to start with. Like you were like, I'm only twenty two, can I do this? Or do you know that, right? I don't know if it was like doubting yourself, but like you were letting that age affect you too. And some of that I think is external like limitations that we absorb ourselves. It's the assumptions of the world, right? And we just assume those. And it's a shame how long I even let that kind of stuff like
hold me back. Like there's a lot more to my story. I mentioned being like a you know, district manager at twenty five, like being offered that and then ultimately turning it away. But there's also a blip in my life because of so much going on with divorce and being like a young single mom that I f even forgot about that or I didn't consider it part of my story. And what makes me who I am today and how I lead business was like, a lot of people see me as the systems girl. And I was like, I am but bitch I've been selling and was classically trained and leading
Caelyn Zupko (22:43.648)
Mm-hmm.
Caelyn Zupko (22:54.729)
Yeah.
Steph Rubio (22:56.791)
20 salespeople or again saying no, thank you to leading 20 salespeople. And I led four, I think, in my store at the time, which was the highest producing store across the company, which was across like two or three states. So Yeah, terrible job. No big deal. But like I didn't again, there was like this gray area of my life where I put that out. I was like, okay. So when I'm thinking about the full thing, like how long I've been leading, and again, I said I'm like fascinated by the why and how things work. And I'm always thinking about these deeper layers. So like the kind of
Caelyn Zupko (23:07.424)
Casual drop there.
Steph Rubio (23:26.315)
waves of all of my life and how that comes into who I am now and like how long I've been leading, but like what makes this a good leader. And again, it's something I had to study in theories of leadership was this concept of like, well, are you born a leader or can you be trained a leader? You know, and stuff like that's a hot topic people like to debate. And and I think there's a little bit of both, right? We can look at really young kids and see them emerging and doing it. But there's also this training component that you absolutely can. And I think one of the key components of leaders is like
Caelyn Zupko (23:39.935)
Mm-hmm.
Caelyn Zupko (23:45.278)
Yeah.
Steph Rubio (23:55.378)
never getting to this place that you see yourself as like the leader at the top of like I've made it as a leader because you can always be led as well. and it's harmful to get to a place for you, the ecosystem, the business, whatever it is you're trying to lead, to get to a place where you think that you can't be or shouldn't be. when we go back to twenty two year old Caelyn is there anything you would do differently at the time based on what you know now?
Caelyn Zupko (24:05.887)
Absolutely.
Caelyn Zupko (24:24.882)
Yeah, I mean probably a million different things, right? But I think mainly like just trusting myself a little bit more. I think I let a lot of external noise in and affect a lot of the decisions I made as a leader. You know, I while I did lean on my team a lot and like really wanted to make sure that the comp it was a great place to come and work, I think we went a little too far in that direction and sometimes like their voices overshadowed my own and overshadowed
leadership and then we got into some situations here and there where you know I was like man I wish I had done that differently but it was because I didn't trust myself enough right I was kind of always looking for that external validation I wanted to be the manager that everybody loved I wanted to be the person that people wanted to work for and I was it just was that like I let those other voices drown my own out a little bit and I would definitely go back and be like no like trust yourself a little bit more trust your gut you have what it takes to be in this role you wouldn't be here if you didn't so lead
in that and not what everybody else needs you to be.
Steph Rubio (25:26.571)
Yep. my God. Okay. So fast forward, there's some of this is not just an age component. I think is important to note for people because we are talking about like young leadership and how fascinating it is that you could even land a role like that young because again, the limitations most people put on that you absorb yourself is like, you can't because you're young. Like what experience you had to lead other people and all of that. But the it's not always age based because
Caelyn Zupko (25:32.368)
Yeah.
Caelyn Zupko (25:44.357)
Mm.
Steph Rubio (25:51.564)
That's something I experienced myself and I didn't get myself out of in the positions or anything like that. Like doubting myself being in the room and still feeling unqualified to be in the room, which is crazy. You know how I tricked myself? And now this is a reminder of me. I used to talk about this a lot in my own messaging a couple of years ago and I haven't lately, but people are like by being in this room. So when it happened for me is and I wasn't twenty-two, I had to be, I'm like thirty-six now, so thirty, thirty-one area, I found myself.
Caelyn Zupko (26:00.529)
Yes, yes.
Steph Rubio (26:19.241)
at one of these leadership tables for the first time. I was an executive assistant project manager. And I grew up with nothing, Caelyn, like you know this, right? Like I've been working since I was sixteen too. So again, we're very similar there. And just worked, worked, worked because I had that need and to make money or had some needs to meet. And so I have just always worked and I didn't climb a l climb a ladder. People also mistake that that like I talk about being on these corporate leadership teams. That's not how I landed there. I worked
Caelyn Zupko (26:26.49)
Yeah.
Steph Rubio (26:45.663)
I worked waitressing jobs, I worked banking jobs, I worked insurance jobs, I worked those sales jobs. I've just worked my butt off. And through that landed myself this opportunity as executive assistant project management, which means then I was in this room of executives doing all of this, these talking and this big level planning and looking at all these profitability stuff. What a lot of what I know and lead today, and I'm looking around freaking terrified of like, What the fuck me? What am I here? Like
Caelyn Zupko (26:51.493)
Mm-hmm.
Caelyn Zupko (27:09.231)
Yeah. Yeah. Yep.
Steph Rubio (27:12.289)
This dude graduated from Harvard. I haven't even been to college. Like I, you know, I've since finished. But all of these things and I was discrediting myself and I wasn't speaking up as a result. So I won't spend a lot of time here because I've done episodes on this. Actually, one of my earliest episodes was about my mentor in that room, the CEO who was a woman, noticing because not in that room, because we would meet one on one, right? And I talked to her like this. And all of it was mine. I wouldn't hold back because I wasn't dis discrediting myself with her.
Caelyn Zupko (27:29.838)
Yeah.
Caelyn Zupko (27:37.348)
Yeah. Mm-hmm.
Steph Rubio (27:41.676)
And she would see the smarts and she would be like, What you need to be saying this in there, right? So and then I would, and then she would come behind me and slack and be like, Yeah, girl, smart, do that again. And I slowly got the confidence. What I then realized, and I would trick myself into when it happened again, because it took a while, was that, and I used this to tell other people, looking around that room, all of those smart as hell people I just said, this woman who was in her fifties, who is a COO of a tech company, smart, making bank.
Caelyn Zupko (27:45.76)
Yeah.
Caelyn Zupko (27:52.868)
Mm-hmm.
Steph Rubio (28:09.729)
The CEO is a Harvard grad, right? The CTO had been doing it for 20 years. Brilliant chief technology officer. All these smart people, the chief revenue officer bringing in millions and me thinking I don't belong there. You know what I was doing? I was underqualifying myself, but I was also assuming all of those smart people I just said were smart weren't smart enough to know that I didn't belong there. You know what I mean? Like really the four or five people that I just said were so much smarter than me.
Caelyn Zupko (28:32.736)
Yeah, absolutely.
Steph Rubio (28:38.177)
like made a mistake and let me in the room and didn't realize I didn't have degrees and all that. No, they were smart enough to know I did need to be there and that they did need that. It was me that was doubting myself. So like by doubting yourself by thinking I'm 22, are you sure you are discrediting the people who gave you the role, assuming they weren't smart enough to know that you were the one who should have been there. So like just trick yourself into remembering that if ever necessary.
Caelyn Zupko (28:42.306)
Yeah.
Caelyn Zupko (28:47.372)
Yeah, that's a point. Yeah.
Steph Rubio (29:06.571)
And I think the other piece that needs to be said is that community and that mentorship can do all of this for you, can help you get there when you can't get there yourself. So if you can't trick yourself into that and you're still struggling with like imposter syndrome, that's what it was for me. Looking around, being like they got it wrong. They're gonna figure out any day now. But it be me and stuff like that. Exactly. I'm gonna say one thing and they're gonna be like, This idiot, what were we thinking? And
Caelyn Zupko (29:27.159)
It's a matter of time. We're on timer.
Yeah.
Steph Rubio (29:34.454)
And that's not how it works. And my mentor helped me realize that it changed everything in my life. Like I talk about that, like the way I show up, the way I'm confident, the fact that I mentor now is because she changed the game for me and how I show up. But that community too. So if it's direct mentorship or community, because when you can't see it yourself, other people can just be like, Shut up, bitch. You are that girl. Right. But yeah, and in business, especially what we're doing now online.
Caelyn Zupko (29:55.799)
Yep. You are that girl.
Steph Rubio (30:02.369)
We don't have that naturally. You have to find it and you have to create it. I'm not like we're solopreneurs. We're running lean teams, if at all. We're not showing up in a room of leaders who will do that and mentors that'll pull it out. You have to find that and create that. But don't like cost yourself as a result. Cause it certainly can cost you if you spin in your head and you let that doubt creep up on you and like doubt your own abilities. What a travesty. Cause the other thing I've now learned, thanks to all of that and therapy, my therapist is like, when have you ever not?
Caelyn Zupko (30:24.738)
Right.
Steph Rubio (30:29.739)
worked hard for yourself. Like when have you ever not pulled through? And I was like, well, I don't I don't know. But exactly. Exactly. So like it's just here in your head, you know, and you're doing that. So I'm curious like how you like how this, how young leadership, how especially 'cause that's years ago now, right? Like how does that show up in what you do today? Because obviously there's some leadership to everything we do and there's leadership to running a business and people are struggling need some leadership skills, I think, sometimes.
Caelyn Zupko (30:31.307)
Yeah.
Och där är jag.
Steph Rubio (30:58.593)
But you're doing like personal branding content for real estate agents, helping them become the local celebrity and really create like a lead generation strategy there. How does your young leadership play into what you do today?
Caelyn Zupko (31:13.685)
So I mean, even in the real estate space, I'm young, right? Like I got into real estate young and I'm still pr I'm still almost always the youngest agent in the room, if not one of them. And, you know, now that we're sort of transitioning out of real estate, I thought it was important that I really carried my knowledge into content strategy. So I'm a big proponent of fake it till you make it. and I spent most of what I've done in real estate so far faking it until I made it. I
just kind of put myself forward as the go-to. I listen, I literally called myself Pensacola's best realtor for a year and a half. and you know, you might look at sales volume or whatever and be like, you're not the best realtor in Pensacola. But for me it was important that I just embodied that mindset, right? I was like, well, I might not be the top producing agent. I might not be the agent with the most experience or the most deals, but I can promise you that my work ethic and the way that I will show up for you will make me Pensacola's best realtor.
Steph Rubio (31:53.175)
Yeah.
Caelyn Zupko (32:07.451)
And so I used social media to kind of market myself that way and built a pretty big following, built a huge community that won me awards for that. And then I'm transitioning that into showing other realtors how to do it, right? I love teaching. I love showing other people the same way I did. I'm not a gatekeeper here. I will tell you my strategy. I will give you my thought leadership. and now I'm doing it as a job, which is really fun because I get to just kind of talk about what I've done in my own business and teach other people how to do it.
So I think it's really just like rolling in the components that I have kind of had my whole life, like just being a natural born leader, a natural teacher, and just showing other people the way and building that community the way that I.
Steph Rubio (32:47.125)
Yeah. Where did you have to become like a beginner again in that? It sounds a little bit some of the areas of like just like I don't know. I've never led a retailer before. You're like, I don't know, I've been never been a realtor before, but we're gonna figure it out.
Caelyn Zupko (32:50.695)
Yeah.
Caelyn Zupko (33:00.066)
See, my theory at first was okay, well, real estate and retail have to be pretty similar, right? You're selling something to somebody, you kind of have to work through the sales process. Real estate is a lot more than that. I hate to bring it to you if you think that a lot of people yeah, a lot of people think that being a real estate agent is the easy way to make money, and I promise you it is not. Hit me up later if you want to talk through that. But now, even going into content strategy, like I still feel a little bit like a newbie where it's like, Okay, I did this myself, but how do I replicate it for
Steph Rubio (33:08.512)
Next.
Steph Rubio (33:12.301)
More regulated.
Steph Rubio (33:18.912)
No.
Steph Rubio (33:27.767)
Mm. Yeah.
Caelyn Zupko (33:27.972)
multiple people, right? You know, it's a learning curve. But I think a lot of people let the learning curve scare them and they let them t they use that to talk themselves out of doing something. Like honestly, a lot of realtors fail in their first year of real estate because they're new at it. There's not obvious mentors in real estate and they don't have a direction. So they just kind of fail out because they're like, I don't know what I'm doing. They flounder and they fail. So I think it's important to show like you do have to keep showing up for yourself, investing in yourself.
Steph Rubio (33:49.345)
Yeah.
Caelyn Zupko (33:54.774)
And like really just kind of like trusting that you can do it, you just have to put in the time and the effort.
Steph Rubio (34:00.619)
Yeah. And I mean, real estate is entrepreneurship. Like still, you're running your own business, you're your own contractor typically. You are learning sales like never before. And I don't even know if some people know that. Like, yeah, you're selling houses, but like you are learning the art of sales from generating the leads to having the conversations to getting to the close. So there is this like trials and tribulations and betting on yourself component.
Caelyn Zupko (34:06.31)
Mm-hmm.
Caelyn Zupko (34:11.93)
Yeah.
Steph Rubio (34:24.481)
that is absolutely necessary. I don't know if I've told you this. You know my sister's a realtor. We've obviously been talking about that and like feedback on some of what you're doing, but I started to get my real estate license. I was taking the tet the studying, not taking the test. at the same time she was and we were like, we're gonna do this under this broker and we might start a business one day and all of that. And then my husband got the job here ten years ago and we moved here and I'm like, Whew, thanks, dodge that bullet. Just kidding. Yay.
Caelyn Zupko (34:39.332)
Yeah, yeah, yeah.
Caelyn Zupko (34:47.898)
Mean it is a lot and it's not for everyone. Again, people think that it's just like this easy get rich quick, and it is not. There is so much that goes into it. First of 65 hour licensing course, and then you have to pass the real estate exam, which most people fail their first two or three times. but it's it's a lot of risk and it's investment heavy in the beginning. Your licensing fees, your brokerage fees, your signs, your business cards, like
Steph Rubio (35:01.889)
Yeah. It's a lot of work and a lot of risk too.
Caelyn Zupko (35:12.214)
It is very costly and I mean you're working for yourself for free until you get a closing, basically. So
Steph Rubio (35:17.877)
Yeah. Yeah. I think I wrote this down too, so I'm backing up here. Like I wrote innovator whenever we were talking there because you you I forgot how you said it, you definitely didn't say it like that, but something along the lines of like you're just figuring it out or like fake it till you make it, right? And I was like, Yes, in a way, but like you're innovating because like yes, a lot of people are creating Facebook groups and stuff like that, and they use that as lead generation and then all, but you went hard at it and have become well known in our area for that.
Caelyn Zupko (35:35.15)
Mm-hmm.
Steph Rubio (35:44.534)
And now, like you said, you're figuring like you're having to innovate again in transitioning. Like, do you know what you're doing? Yes, but that's in the delivery. Now you have to convince people with your messaging that this is what they need and all of that. So there's figuring out again and figuring it out again. how did your previous leadership experience help you trust yourself through these transitions?
Caelyn Zupko (35:53.282)
Mm-hmm. Yeah.
Caelyn Zupko (36:05.976)
I mean, I think at the end of the day, like I've made it, right? I every time I've had some new shift, new change, like I've just figured it out. And I think it's very easy to get caught up in the I'm not good enough. I can't do this. What am I gonna do? Because you know, you have to transition or pivot or whatever. But I've always just been able to put my head down and just do the damn thing. So that's kind of where we are now where I'm like, I don't really a hundred percent know how this is all gonna work out, but I'm just gonna do it. I'm gonna figure it out and I'm gonna do it and it might not be perfect.
Steph Rubio (36:24.482)
Yeah.
Steph Rubio (36:30.701)
Yeah.
Caelyn Zupko (36:33.771)
I think that's been maybe my biggest lesson is that it's probably not going to be perfect. And I am very good at letting that paralyze myself. But we're learning to like push forward and go, okay, no, it doesn't need to be perfect. You just need to like do it. We can make it perfect later. And that's really important because I think the perfection really like stalls people and keeps them from reaching the dreams that they want. Whereas I like I know that the, you know, the perfect little pieces will fall into place or they won't. And that's okay because it doesn't need to be perfect. I just need to
Steph Rubio (37:00.983)
Yeah.
Caelyn Zupko (37:03.774)
start talking about my thought leadership and the experiences that I have and that will bring ideal clients and it will bring people my way and opportunities that will mean more than spending three or four hours perfecting something that nobody looks at.
Steph Rubio (37:14.677)
Yeah, that you can capitalize on in the way that makes sense for you at that time. Right. I think that like what a lot of people don't realize, I talk about this frequently, is it's like stop worrying about the how for half a second, you know? And because the how, the not knowing how is what peop people let keep them stuck. And the good news is like I talk about this in a lot of way, is that if you don't have something to get there, it is either a skill
Caelyn Zupko (37:25.196)
Yes.
Caelyn Zupko (37:33.151)
Mm-hmm.
Steph Rubio (37:42.22)
Or knowledge or like a connection or something like that, you know? You can find those. You can fill those. You can pay for a course. You can whatever. So why would you start there? Start with like what? You know, your what and your why? Like what is it you're doing? Why? What do you need to make that happen? What gaps? Like I talk about it like that. Okay, now we know we used to see me do this a bit in the quarterly business review. Like we're reviewing all the things. And now the very last thing, once you have all these priorities, is what do you not have to make them happen? Of anything on that priority list.
Caelyn Zupko (37:47.34)
Yep.
Steph Rubio (38:11.649)
that we have now said is matters to get your business where you want to go. What do you need to make that happen? If there's anything not within your means, we're gonna make it within your means.
Caelyn Zupko (38:22.697)
Yeah.
Steph Rubio (38:25.973)
Okay. Let's wrap up here. Sorry, I pause because I can hear you pop. go ahead and give that a second.
Caelyn Zupko (38:31.668)
Give me two seconds.
Caelyn Zupko (38:37.898)
They're so annoying. They were quiet the whole time.
Steph Rubio (38:39.381)
Yeah. Right. We're coming up on the end. They're like, That's it, Mom, we're done here. So yeah, I think it's like important. I'll just wrap I'll say that again 'cause I think they started barking there, but good if I can pick up my thought. yeah, just kidding. I'll totally lost it. like it's just a knowledge or skills gap. So when you when you get to this and you look at it like, okay, here's the things that said I'm gonna do. Are there anything I can't, like like I just don't know how or can't or don't know, like now you have now you just gotta fill that gap, right? Now
Caelyn Zupko (38:43.43)
Mm-hmm.
Caelyn Zupko (38:49.757)
Yeah.
Steph Rubio (39:08.957)
What can you do? And if you can't do that, that's a different story, right? Now, if this is gonna take 25 grand, okay, now are we talking grants? Like I'm coming off the wall here, but the point is that like the how usually is a way, but people let that how keep them stuck instead of just jumping. And I find that starting with that clarity of what it is you're trying to do, like a why, whether that's the whole business you're trying to build or that's just next quarter's priorities, like what are those?
Caelyn Zupko (39:12.69)
Mm-hmm.
Caelyn Zupko (39:30.292)
Mm-hmm.
Steph Rubio (39:35.948)
Then we get to the how, but we're not gonna stop ourselves before we ever even get there. Like what the heck is that? What is that gonna do? Okay. As we wrap it up today, Caelyn, if there are people listening who are staying stuck, who are letting that fear of being seen or whatever it is, or feel underqualified or feel unready and they're letting that stop them and staying stuck, what would you say to them?
Caelyn Zupko (39:41.258)
Absolutely. Yeah.
Caelyn Zupko (40:01.166)
This is gonna sound so cliche, but just do it. Like just jump in, bet on yourself a little bit and do it because the worst thing that can happen is it doesn't work out and that's a learning opportunity and it's a way for you to kind of like pivot, shift, whatever the case may be. But if you don't ever try, you'll never know. And if you don't ever bet on yourself, like how can you grow and be a better person and do all the things that you dream of, you have to be willing to take a little bit of a risk.
Steph Rubio (40:18.475)
Exactly.
Caelyn Zupko (40:28.092)
And I know that that's so scary. Like I get it. As an anxious person, like I understand that it's scary. But is it scarier than just staying still? In my opinion, absolutely not. Staying still and stagnant and not growing and learning is so much scarier than just trying and maybe failing.
Steph Rubio (40:36.097)
Right, yeah.
Steph Rubio (40:43.221)
Yeah. Yeah. It's l I love that little worst case scenario like a staying stuck or not. Okay. With anyone listening who has now fallen in love with your approach and what you have to say, where can they keep up with you?
Caelyn Zupko (40:47.784)
Yeah.
Caelyn Zupko (40:56.366)
on Instagram is where I'm the most active @caelyn.jpeg And then I have an email subscription list where I like to e yap at you all about all the things I got going on.
Steph Rubio (41:04.735)
Okay, cool. I'll drop both of those in the show notes so people can find you, keep up with you, hang with you, go say hi to Kaylin. I happen to talk to her in the DMs I know she's ready to have a conversation with you. So I would imagine I don't put words in your mouth, but if anyone had anything on this episode they wanted to ask you more about, you would be open to that.
Caelyn Zupko (41:13.0)
Always.
Caelyn Zupko (41:21.274)
Please, I love a voice memo, so let's yap about it and work through whatever you got going on and I'm here for ya.
Steph Rubio (41:27.562)
Well thank you for coming on the pod, Kaylin. This has been a joy. I appreciate you so much.
Caelyn Zupko (41:31.748)
Thank you. I appreciate you. This has been so fun and I loved our conversation.
Steph Rubio (41:35.081)
All right, we'll catch you guys next time. Bye.
Caelyn Zupko (41:37.326)
I
Steph Rubio (41:40.568)
I get my mouse here.
