In this episode I interview John Powers. John and his wife, Kaylee, own a prominent residential real estate sales practice located in Virginia Beach, Virginia. Today we talk about how John and Kaylee left the security of both having salaried incomes to going all in on commission income as a family. We discuss how they navigated a succession plan that happened faster than anybody planned both relationally as a family and professionally in the community. We also discuss John's desire to remain humble amidst all of the transition and growth in their business. And be sure to listen to the end as John discusses the dynamics of working and running a business with his Spouse- the challenges and how they made the decision to hire a coach to help them grow in their marriage, have hard conversations, and ultimately produce more connection.
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leland (00:01.174)
All right, welcome John Powers to the Self-Employment Success podcast. We're excited to have you here. Great to be here. Thank you, Leland. Yeah, I'm excited for today's conversation and just hearing more about your story. So to start, just tell us a little bit about yourself, your family, and your business as it stands today. Yeah, so I'm married to my wife, Kaylee, and we have two daughters and another on the way. Our daughters are three and one and a half, so that's awesome and wild.
Um, together we have a residential real estate business. So we lead a team under a brokerage and, um, there's seven of us on the team. Five of us are agents and we have two support staff. One of those is a marketing director and others videographer. So, cause we just do a lot of online video stuff. Um, yeah, so that's been really fun. That's awesome. Tell us a little bit about how you got started in the business.
I feel like a lot of agents work on teams or solo. You guys clearly have a really established team in the Virginia Beach area. So yeah, how did you get started? The beginning was a unique starting because my wife and I were, her grandmother had been in the business in real estate for 40 years and was a really well-known name in Virginia Beach and grew up in Norfolk, the next town over. And.
when you know, Kaylee and I had never really thought about getting into real estate. I mean, I guess I had, but not so much in the way that we ended up doing it. And at the time, she was working, she had gotten her degree in social work, her master's in social work was working at a hospital and I was working in a sales job that I've been doing for a few years and kind of a corporate job that I didn't see myself in long term. And one day, we
friend of mine came to me who was interested in getting into real estate he said hey can I talk to Kaylee's grandma I know she's super successful what she does I was like yeah let me connect you guys and so I talked to her about it and Brenda my wife's grandmother was like yeah let's talk I'd love to talk to him and by the way you guys you guys should think about getting into real estate you know I'd love for you guys to take over my business and I was like huh and he's coming off guard but you know so
leland (02:25.002)
it clicked immediately. I was like, this is interesting. So I went back home told Kaylee about that conversation. And it just began a process of trying to discern is this the right move for us. So yeah, we could get into that later. But basically, we ultimately decided to get in to move forward with it. Get into real estate, at least to get our licenses and
join the business, we didn't know a lot of what that was going to look like at the time. But yeah, it felt like the right first move. And so we went all in, which was going from two salaried jobs, mine was salary and commission, to 100% commission. So that was a scary thing to get over. But so far so good. About five years in. That's awesome. There's so much
there to unpack. So to start, you mentioned, you know, I had thought about getting into real estate, but not in the way that we eventually ended up getting into real estate. So there was something on your mind about that world, which is a big world. So I guess tell us a little bit about what you thought earlier when you were dreaming about, you know, potential real estate. Where were you at in that mindset? Well, I always wanted to...
not maybe not always, but probably starting sometime in college, I was really excited about real estate investing and started listening to Bigger Pockets a ton and talking to a few friends that had older friends that had real estate investments. And I was like, I like that. I like this idea of passive income. And so it just, you know, started reading more books on that. And so real estate was intriguing in that way. Also growing up, my house was under construction my entire life. So I felt like just, you know,
I had a decent understanding of construction and renovation and loved looking at homes since I was like a little kid, which I think a lot of people can relate to that excitement around homes. Yeah, so that was there. You go to your friend's house and you're like, wow, this is beautiful. Look at this, or they've got this, you know, movie theater in the basement or whatever it may be. Yeah. Okay. Exactly. So you are growing up, you're kind of around it. You have this idea of, you know,
leland (04:44.15)
bigger pockets, real estate investing. And then this apparently poor friend came to you and said, I would love to work with your grandmother. You go to grandmother and then grandmother says, well, actually, why don't you do it? Well, the friend just wanted some advice. He was just seeking it. He wasn't saying I wanna come work for her. Okay, like that poor soul. Yeah, but it did open the door to the conversation. I think they spoke and he ended up doing something different. But.
it opened, you know, it was meant to be that kind of opened that door for Kaylee and I. Yeah, so we jumped in. Yeah, and you also mentioned this, just how unique it is to go in into business in general with your wife. We have examples of it. We've got Chip and Joe and, you know, all these ideal scenarios of working with your spouse, but I'm sure in reality that poses
so many layers and complications to the relationship, probably in a good way and in a challenging way. And so you guys both take this leap together, not I'm doing this and then later you come along with me, but we're both just quitting our jobs, leaving all safety behind, and jumping into a full commission world. So tell us a little bit about what it's been like working with Kaylee as your wife, kind of being in business together.
Um, and I guess a little bit about, you know, that transition. Did you have a ton of money saved? Was it, you know, I guess what were you doing to make yourself feel like, okay, we can do this? Um, a couple of things were going on there. Yeah. I guess the, there was a period of trying to figure out, should we do this at all and should we do this together? And in hindsight, it totally made sense to do, but we were, you know,
especially going to the 100% commission was a scary thing from having kind of a base income together. And we were married like six months or something. I got that timeline right. So it was early in our marriage. So it was a lot at once. And so we did this book called Draw the Circle, which is the general idea of it is there's a 30 days.
leland (07:07.126)
where you're led through prayer every day around making a decision or around... I think it's a decision or asking God for a direction on something or healing on something in a lot of different ways. But in this case, we were just trying to decide, should we move forward with this? And at the end of that, it felt really clear to us to take the next step. And so...
that looked like to us to take the night classes for real estate while we were still working full time. So we'd come home from work and throw pizza in the oven and then we did it virtually like a live class but those were those were funny days and so we knocked that out together and at that point I was uh I had just started hitting the stride in my sales job where I was starting to close a fair amount of business and I had my largest check coming in
think if the time like roughly you know this might be June we're decided we're gonna move forward with this and did our classes and then I knew that this check was gonna come in August and from a from a big sale and so that was a little bit of like okay well this is gonna give us some runway to get going and that made that gave us a little piece to jump in but yeah like that's where we were at money-wise that helped a lot we had
I was doing okay at that job, doing pretty well at that job and had kind of just started hitting that six figure mark where it was like, okay, it was kind of getting very comfortable, so to go back to zero was scary. Yeah, I mean, even with the clients I serve, even if you have a surplus and you make a change and you still have a surplus, but it's just less, it's like you still have the same quality of life, but it feels so much more uncomfortable because you're like, I'm used to having this.
number coming in every month. This number in my bank account and whether it's right or wrong, we all kind of find some peace or solace in that. And so then when things are coming, when things are not coming in, especially in real estate as you're getting started, or things are coming in that are a little bit less as you make a transition, it's yeah, it provides a lot of anxiety and tension. It did. But well, yeah, I guess I jumped to that. But it ultimately that runway helped.
leland (09:32.298)
runway helps for sure. And so what was the agreement with your grandmother? Was she kind of actively, or I guess Kaylee's grandmother, was she actively leading the team and you guys were underneath her kind of doing a commission split? Or was she more kind of on her way towards retirement and you guys were running the team? How did that play out? Were there other teammates on the team at the time? Yeah. Yes, all the above there was
bunch of different things going. We got we're getting into something we didn't really you know understand how it what was typical and so we knew that she her desire was to move towards retirement but at the same time she was also thinking like you know I want to sell real estate until for the rest of my life but I want to also hand over the reins it was a trying to figure all that out was interesting but we you know stayed united through it wasn't like that you know thankfully
probably like one or two somewhat hard conversations, never really that hard. It was a lot of grace from her grandmother and a lot of give, like she wanted to bless us with that, which was pretty wild. She wanted us to succeed, I guess, in it. And she wasn't trying to say like, oh, you need to do this, or this for me. But at the beginning, there was a, we, any of our sales, a split of it went to her. And that was just part of how we had set it up, made sense, and that's typically in the team model of real estate.
the team leader who's taking on a lot of different expenses. If you're under that team, there's a split that you have within the team that part of that, part of your sales going to the team as a whole, the team business. To cover everyone's kind of getting the same marketing, everyone's kind of having a support staff help them write up agreements, things like that. All that. Okay. So yeah, it could be, it depends on the team, but there could be, yeah, tons of overhead or it could be very straight, very simple. But at the time ours, there was this
somebody on staff helping with all the transactions, all the marketing, all that stuff. And since then it's changed what we provide, but we have a heavy on the marketing. Yeah. And so it sounds like based on what you said now, you've got five agents to support staff, but it sounds like Kaylee's grandmother's no longer on the team. She's probably, I'm assuming, retired or.
leland (11:54.654)
move forward along with that other support staff. So how quickly did it happen where, okay, we're coming in, we're learning the ropes, we're splitting with Brenda and kind of have the benefits of her team to, okay, now we are running the team and we're kind of taking over what we provide, we're calling the shots on what the team provides and things like that. It was a, that was an interesting dynamic because we were.
pretty young and we came in and there was a few other folks on the team that had been with her for different periods of time, some 30 plus years though. And it was hard to, it was, you know, unique to step into as a 20, mid 20s and kind of like, am I, I'm kind of running the show now because I'm starting to pay the bills, but I also am figuring this out. So trying to be humble and navigated and it, it all worked out in the end, but it was.
That was interesting. One of the dynamics was Brenda was, had been doing this for so long, she kind of had her systems down. And so Kaylee and I, you know, they had their systems, but it wasn't her style, couldn't be necessarily our style as being new in the business. So we kind of had to figure out what's our style, what, you know, where do we need help? Where do we, because we learned a ton from her just as far as communicate. How do we communicate with people?
questions to ask, all that stuff. But we also had to kind of make it our own because coming from just a seasoned vet who had been doing this for a long time and had a different personality type than us too, she could command the room in a different way than I could, just from experience. And so there was that. And then another dynamic in all this was that.
in the first year of working together, we started realizing her health, her memory was, something was up. And so that began, you know, we started having more and more conversations about that and realized, she kind of realized with conversation with the family, like, she probably shouldn't be, she wanted to step out of the real estate role because she could tell that there was issues with her memory that weren't, that were
leland (14:19.246)
affecting how she could do business. That was a really hard time of us all navigating that together. My wife, being her grandmother, trying to figure out how to, just more, you know, being sad that was happening for her. And it, you know, developed into dementia. And so she stepped out of the business and we've had to kind of go forward with how do we.
keep her legacy alive honor her as she's handed this business to is probably faster than she was expecting at the beginning or any of us were expecting and
Yeah, how do we also take care of these relationships that she had formed over all these years? And some of them we never got to meet before she had stepped out of the business. So we've got to have, you know, come in and be like, hey, yeah, so I'm, Brenda had chosen Kaylee and I had to join in her business and we worked alongside her for a few years and now we're working together. Yeah. So it's been a good challenge and a good, well, good elements from the business standpoint, but it's been hard.
course, just to walk through that together as a family. Yeah. Again, there's so much to your story of, you know, really successful grandmother with a with a well known name brings you into the business in your first year of marriage, leaving safety behind, and then quickly being in a place where we're learning the ropes, we're learning the ropes. Oh, she's now
understanding she needs to step out of the business, which is normal. Like we all know grandparents who over time, their mind begins to go. And I think it's wonderful and wise that she kind of came to that understanding and said, Hey, I need to step back from this. And, but now you guys are left as the heirs with the family name, the family. Like you are the family, you are the legacy. People would call the Brenda Rawls team and they'd get me on the phone and be like, who are you? Yeah.
leland (16:29.47)
And you're not even, hey, Brenda's my grandmother. Brenda's my wife's grandmother. And so to try and honor her and you're still learning and to try and assume those relationships kind of throws you, I'm assuming, throws you both just deep into the fire quickly. Yes. Hey, we had a little bit of time, probably six months to a year of figuring this out. And then, boom, now we're running.
the show, now we're assuming these relationships, now we're in charge of what this team is gonna do. And like you said, we're younger and the way that we're gonna do things is gonna be different than Brenda, who could rely on her relationships that she's built for probably 30, 40 years and has her style, has her marketing down. And you guys are now assuming that and forging a path for yourself at the same time. Yes. I mean, that is just.
Entrepreneurship at its core in many ways and I'm sure is a story for so many other self-employed families who if they're not forging it on their own, they're Succeeding someone else or taking over a family business or purchasing another business where? Hey, it's though. It's the legacy of this but with a new face and flavor and There's so much delicacy to balancing that can you?
speak to that, like as you're that dynamic of, hey, I'm reaching out to a faithful old client of Brenda's who doesn't know me. What was that like trying to assume that relationship, trying to honor her and, you know, also continue to grow and build the business? It was, it's getting easier and easier. It was hard at the beginning because it felt like it was a lot to assume and we wanted to.
honor Brenda not, you know, at the same time, I want to put myself in the shoes of this other person and be like, Okay, you've never met me, you don't know who I am. But we do, you know, genuinely want to be able to serve your real estate needs and anything we can help you with in the same way that you've come to expect. So just trying to continue that relationship and stay humble and that was our dynamic. But also it was, you know,
leland (18:54.486)
feel like it, we had, one thing that made it easier was we'd had Brenda's blessing very clearly. She was like, these are my, these are my, you know, I've given, I've handed over my business to my granddaughter and her husband and they're very capable. They're really, you know, she really, that was super, super helpful just in how she communicated to us about it and to others and that helped a ton.
So you did have a season of being able to either just in the community talking about it or through whatever marketing funnels to say like these are her to say like this is my granddaughter I mean to those listening I've met Brenda and Kaylee and Kaylee is just the spitting image of Brenda so having them next to each other. You're like you are clearly a member of this family. But you did have a season of her kind of publicly being like this is my
passing this down and this is my blessing. And it's still our neighborhood. It's still our family. We're still serving. We did that through personal letters, Christmas cards. We did it through a magazine, articles, different things that just kind of got the word out in the community so that people kind of understood it. And then about two years ago, we rebranded the business from the Brenda Rawls team to Powers and Rawls. And
we wanted to again kind of continue that legacy of what Brenda had built and also kind of reflect the new that we were in this together and kind of carrying it forward. But just because it had become a trustworthy name in that world, in the real estate world in Virginia Beach and in the surrounding areas, we wanted to keep that name recognition. Keep that name recognition and yeah.
but also we felt like a shift in the name made sense since people were expecting to, you know, if they wanted to talk to Brenda, Brenda wasn't there. That was a hard, you know, it was like, well, you're talking, we can talk. Yeah, well, and as new relationships are coming in who don't know Brenda, it's like, okay, well, I'm working with John Powers, not Brenda Rawls team, who's Brenda. And so I'm sure there's a place of saying, we're honoring
leland (21:21.09)
keeping the name, we are the legacy that it's the same quality as it has been. But the powers family are now the ones running it. And with the last name like powers, it's a strong name to put on marketing. Thank you. Brenda Rawls powers team. So going back to working with your spouse, I've worked with a handful of couples who are in business together. Honestly, some of them are in business together. Some of them just.
both own their own businesses. And sometimes dividing the line between business and personal gets hard. You are at the dinner table talking about work. You're on a date talking about work. Or you're in the office talking about personal life. And I find that some people that navigation's pretty easy and natural and for others it's really difficult and trying to find when does our business partnership end and our marriage begin.
And so what was that like for you and Kaylee, both early on and today, and have you had kind of a journey there, or has it always been pretty seamless? Definitely been a journey. Starting at the beginning, it was a definite fear going in. We were like, or we were a little nervous about what that dynamic would be like, but we, very, yeah.
We didn't know. And so we got into it and we started realizing it just was all consuming for us at the beginning. I mean, because it was like we had staked it all on this one throw. And so. And it was new. So it was there was a part of it that was really fun. We wanted to talk about it and that was OK. But then it just started to overrun. It was like you go on a date night and we're talking about work for the majority of the time where we go like one of the funny dynamics that I would joke Kaylee on is like we'd be in bed.
and like head hit the pillow, lights are out and closing my eyes and she'd be like, oh, by the way, don't forget this tomorrow. And I was like, oh no, why did you say that? Now I can't sleep, now I'm gonna be having dreams about this client meeting. So we learned, I was like, okay, we can't do this. My brain does not work that way. I'm gonna not be able to sleep tonight. I need to disconnect. So there was different dynamics like that we had to figure out, like this is not gonna work.
leland (23:44.994)
And yeah, I think that it just, it was so early on in our marriage. And then within a year of joining real estate, starting the real estate business, we had our first child and then we had our second. Gosh, that was within a year. So within a year of marriage, you start this business and then when the, in a year of business, you have a child. Y'all are just plowing through life transition. Yeah, exactly. That's what we were doing. Yeah. At the beginning, when our first.
daughter was born in Virginia, we were like, it was, we were just laughing of like, we did three things in like a year's time that people say you shouldn't do or not shouldn't do but like that any one of those things is a lot to figure out like got married, that was a lot to figure out. Got started a business together. That was a lot to figure out. Had a child and all of that at once. Yeah. I mean, all each one of those things are things that when you're looking back on your life are like momentous milestone things like and then this in this part of my life, we got married.
Right. And then we had our first child and we started this business. You guys just compiled that into one year of your life or two years of your life. That's yeah, that's intense. It was intense. We we very quickly realized we needed help and we weren't. Yeah, too prideful to say it, I don't think. I mean, we one thing that really helped is my brother. And this was part of what excited me about getting into business. There had been some entrepreneurs in our family, my both my grandparents in different ways and.
My brother had a few businesses and his wife had separate businesses, but they did a lot of it together. So we saw that because we're close, saw that up close and personal and the benefits of that, you know, getting to do things, more, spend more time together and go on trips together and things like all the dynamics of that. So we liked that. But we also, um, he introduced me to this resource of a life coach. And so we, Kaylee and I, we weren't like, you know,
I wouldn't say we weren't like a rock bottom at all or anything like that, but we just knew we're like, okay, all these dynamics at once. This is a lot to chew to bite off and chew and so we just knew that there was a lot of conversations that would help our marriage keep us healthy if we had another resource. We basically we weren't going to go there without somebody else.
leland (26:13.83)
um it's like working with a financial advisor i will tie this together like um i pay like paying the life coach was valuable in that we it forced us to come to the to have the conversations and she also had expert advice and could walk alongside it with us and yeah there was a just that was huge to staying united in our
marriage and in business. Like we both, we talked about both a ton and then having kids too. Yeah and so that was a huge resource for us relationally to stay together and I, yeah being in business together, all of those things are hard. Marriage alone is hard. Marriage by itself is hard. Then throwing kids in the mix has its challenges too and then being in business together, it's, it was a lot at once so I can't, I'm a big, big fan of having a...
help in that counselor or a life coach was huge for us. That's awesome. And it is important. I mean, I think anybody would say these things, any life coach or counselor would say these things really do impact you. I mean, they add stress and everything is a house of cards. Just like in finance, your investments affect your taxes, in fact, what insurance you need affect your estate plan. Similarly, your work affects your stress, which affects your relationships.
kids and you know which affects how you treat your kids and sleep deprivation. All of these things are tied together. We love to try and compartmentalize but you can't really compartmentalize. And so I can only imagine having someone come in asking you the hard conversations, asking you the hard questions, making you have the hard conversations. And if you're willing to go there, I think a lot of people it's uncomfortable to go there even in your marriage but it sounds like you guys something you said multiple times throughout this episode
just we were trying to stay humble. Like we wanted to stay humble in our business. We were humble enough to know we were not gonna have these conversations without help. And we were humble enough to like bring someone into that help, which I think is really admirable and important. And it sounds like you guys were aware enough to invest not only time in your business, but then time in your marriage, realizing that's gonna be the healthiest part too. Yeah.
leland (28:42.854)
our healthy marriage will make us a healthy business and make our kids healthy. And, you know, everything kind of stems from that. And so, yeah, I think that's wonderful and powerful and also complex. What a wild season of life. It is. It still is. Yeah. And so are you guys still doing marriage counseling or not marriage counseling, marriage life coaching or kind of how has that progressed to where you are now? We are not.
actively like meeting with Julia who was our life coach for a few years and but we she has some other resources that were actually just started this year. She has like a course that you can do called marriage thrive so we were jumped back into that together and
For us, we wanted to, because we had every two weeks for a few years, we had that rhythm of speaking with Julia and learning from her. And also we would put off conversations until we were, sometimes, you know, this wasn't the healthy thing to do, but we'd be like, okay, this is gonna be a hard conversation. Maybe we'll have it with kind of a referee in the middle of it. Hey, Julia, we're in a fight. You can hop on a call. Yeah, exactly. But.
we wanted to explore like, all right, let's do this. You know, we got to, we can't, we could, but let's try this on our own and see how we can use these tools we've learned for the past few years. And so that's what we did this past year. And it was good overall, but we found, you know, it's easy to go back in your old ways of thinking and habits and patterns of conversations, the dance of the relationship. So we figured like,
We just want to have something that is keeping us in the conversation of having the tough conversations that turn into like great joy and depth and intimacy, you know? That's what we found. Yeah. So I love highlighting the fact that so often we talk about marriage being hard, kids being hard, business being hard, these conversations being hard. But what you said there was, well, we do that because it also produces...
leland (30:59.67)
connection and joy and intimacy. It's like shedding of the gunk, cleaning out the pipes and really like allowing your life to flow fluidly through them. And so I feel like that's true not only in first and foremost your marriage, but also that's why business is hard, but people also do it because it's hard, but it produces reward and
Yes. Brings you to life and provides a life for you that you want. And same with kids. Everyone would say kids are hard. No one's like, kids have been so easy. But there's so much love and joy and fruit there that is to be born. So what surprised you most about your journey through self-employment so far?
leland (31:53.482)
Well, I think some of what we were talking about here, the marital dynamics and the growth there was a surprise of just, you know, how much we'd need to press into that. And then how much we would, as a result, grow from it. Yeah. There's seasonality to it. You know, we've been doing this for about five years and there are seasons that feel great and there are seasons that are really hard. I feel like we're.
end of this past year was a slower business time in the real estate world as interest rates rose. And so that was hard in ways and we had a year of growth as far as like a number of team members, which was really fun. We loved all that. But we wanted to see the
the sales match, the growth, the overhead growth. Yeah, exactly, exactly. So we're feeling that pressure. And as we're coming into the new year, that pressure has subsided a lot. But that's just a little example of the year to year, there's all these dynamics at play. It's, yeah, I like what you said about how business is very similar in that way. There's so many different dynamics at play and to keep the health.
you have to be looking at a lot of different fronts. Yeah, we actually have, speaking of that, we have a business coach too. So we don't have a life coach anymore, but I do have a business coach now. So we're trying to get health, more health there. Yeah. That's wonderful. And what has been the low point?
leland (33:34.59)
Early on, that was when we realized that Brenda was going to have to step out of the business way earlier than any of us expected. That was really hard because we were...
leland (33:49.43)
weren't sure exactly how that was gonna look and you know there's we Kaylee and I were concerned like how do we keep these relationships of all these people we haven't met and we're gonna be able to do this and just doubt in like can we can we push through to make this successful like we had been in it long enough to start it to we were getting a little bit of a hang of it but yeah it was still
There was a lot of also just sad, you know, wishing that we could continue on as a whole unit. And had more years together and that so that was that was hard. Yeah, but in hindsight, you know, the growth from that was powerful. Because it was. It was sink or swim. Yeah.
So this is a podcast about success. And that word success means different things to different people if you ask them how to define it. So in your words, what does success look like and how will you know when you've achieved it? Hmm.
leland (35:07.486)
I think that's a great question. The success, having the freedom for me, success of would be like having freedom to choose how I'm going to spend my time. And at the same time have the resources or, you know, the income to support my family and the lifestyle that we
leland (35:36.394)
Knowing that this was about success, I was thinking about that general concept. And I was thinking about like, on one end, we're not thinking like the fire movement where it's like, I forget if that's financial independence, retire early. We, it's not, I think there's different paths to that. And I was, we also wanted to, you know, there's dynamics that we are thinking like, maybe we'll send our kids to private school and we want to go on certain vacations together as a family. And.
you know, all those dynamics of, so there is a, there's definitely a money piece to it, but bigger than that would be that we could be together and, you know, spend time as a family. And also we're big into relationships in general, outside our family, but also friendships and mentoring and caring for others is a huge part of what gets us just excited about life. And so we would love to.
um, for the business to be the fueling that, um, but success would look like having the freedom to choose to do those things in the middle of my day and, um, to be with family. And yeah, that's awesome. So that was a long answer. It was a great answer. Well, thank you for being on the self employment success podcast. Loved it. Thanks for having me.