Caleb has built a thriving business over the last few years using discipline, grit, and a great working culture for his team. From day one in a new town with zero connections to coordinating the number one real estate team in Mount Pleasant, SC, Caleb has come a long way from when he first arrived in Charleston.
Join me, Caleb, and his inside sales associate Brandon Bott, to discover what kind of character it takes to build a real estate business (or any business) that is always making money and moving forward. Caleb and Brandon have so many tips that you can employ to develop the mindset that it takes to be successful.
Welcome to Love Your Living, a podcast for ambitious women who choose to have it all. Learn how to achieve the massive success you’ve been dreaming of in your business and your personal life. Here’s your host, multiple six-figure business owner and a life stylist, Brooke Keeling.
Hello, everyone, and welcome to the Love Your Living podcast, where we get real in business and ambition and growth and the reality of it. Today, I am so excited. I have a friend and mentor here with me today talking all things real estate and entrepreneurship and how he got started in creating an incredibly strong real estate business.
Brooke: So Caleb Pearson, welcome to the show. Thank you so much for being here with us today.
Caleb: Thank you, thank you, I’ve got Brandon right here with me as well.
Brooke: Awesome, so Brandon and Caleb have been mentors to my team, my real estate team, for a few years now and they are both just rockstars in the real estate industry. Caleb has been in the Charleston, South Carolina market for how many years now?
Caleb: About six.
Brooke: Okay, six years. You started right out of college, right?
Brooke: And in a market that you didn’t know many people, if any people at all, correct?
Caleb: Correct, yeah, I mean, I knew like three people in Charleston when I moved down here.
Brooke: Right, but you didn’t grow up there, you didn’t go to school there, you didn’t have a big sphere that you started working off of diving into your real estate business?
Caleb: Yeah, exactly.
Brooke: Okay, and Brandon is one of Caleb’s team members that has been with you almost since the beginning, or a few years at least?
Brandon: Yeah, going on three and a half years now, so pretty much half the time.
Brooke: Cool, and Brandon is in an inside sales position, so he is always supporting the agents and their team, reaching out to clients, following up, prospecting. That’s kind of his role within their business, Caleb being the owner and the team lead. So, Caleb, can you tell me – you found so much success early on in your career. I mean, I was reading some of your history yesterday and just realized how much success you created so quickly. You were literally in the business for three years and already getting accolades within your market. Can you tell me, what was the beginning like? What allowed you to really create that massive success in your business so quick?
Caleb: Well one – I got into the business and I had a good mentor, or a couple of good mentors. I had a lady named Betty Gales, who had been in the business for about 25 years, and she was basically my coach. So she coached me, taught me where to call, who to call, what to say to people, and I mean, I was just a sponge. So I did exactly what she said and it worked and I’ve done the same thing every day for six years in this business and we haven’t changed and it’s just compounded and compounded and now we’ve got a pretty big business.
Brooke: So what are some of those things that you’re doing every single day? So it’s not rocket science. It’s not the newest greatest tool. It’s not the newest shiny object. It sounds like you were mentored by someone that has probably some old school ways.
Caleb: Yeah, I mean, I wouldn’t consider myself real innovative or I’m not a big techy person, so I’m generating my own leads and building my own websites and lead click-funnels or anything like that. I’ve just done the same thing every single day, and that’s wake up at 4am, read from four to five, go to the gym from five to six, get ready, come to the office and then hit the phones early in the morning and start. We call every day. All my team members call starting the same time every morning and we call the same type of leads and it works.
Brooke: It’s the repetition, it’s the habits you’ve created for yourself.
Brooke: Now, in the beginning, was it hard to take on some of those? Like, did you ever have fears? Did you ever have, like, man, I really don’t want to do this, or I really messed up that appointment, or, you know, a lot of times I think too, like, you started in this business right out of college and there’s always something in our head that we make up stories around. Whether it’s, I’m too young, who’s going to buy from me? I’m a 23-year-old kid and I’ve never even bought a house, or when you didn’t know what you know today, how did you overcome some of that? Or did you not face those types of fears in your business?
Caleb: I would say I definitely had some of those fears. One nice thing that I had was Betty or her boyfriend Robert would go on a lot of my first appointments with me, and I gave up half of the commission on everything but – actually, I gave up more than half on some of the stuff, but sometimes it’s not about the money when you’re first starting. It’s about getting the experience. And once I’d gotten my first, like, 25 homes under my belt, I was pretty confident and ready to go on my own.
Brooke: So you got yourself a coach and a mentor right away and you remained coachable through today, likely. I mean, I know you’re still doing a lot of things.
Caleb: Yeah, I mean, she’s actually – she’s a coach for Tom Ferry now, but I went and I got another coach, Kinder Reese. John Kitchens coached me for a while after that. So I got some higher-level coaching after I was working with Betty and they just keep you ahead of the curve.
Brooke: Sure, so while we’re on this subject of your habits, your routines, your team is in the office every single day at 7am. That’s just who you guys are, what your culture is. You have an incredible culture. I’ve had the pleasure to come down and visit a couple of times now and all of your team members are absolutely phenomenal. So how do you create that drive with your team members? And I think Brandon can probably speak to this a little bit as well, but Brandon, you’re in a tough role. You’re in a role that most people hate even that one hour of what your job is all day every single day. So tell me a little bit about your role and how you’ve found, I don’t know, I guess reward and pleasure into that too, because you’re getting told no a lot. You’re on the phones a lot. You’re getting told no a lot. How do you keep your mind right around that and have been in this position for five years as an inside sales agent?
Brandon: I think it comes down to, you know, when it really gets to the nitty-gritty, I’m super competitive and there’s just something about getting told no a hundred times that just makes me want to hear yes pretty much. But to be sustainable in this role, it just takes a lot of persistence. There’s people I’ve talked to, probably 30 times, before they ever decide to actually meet with us. Yeah, I mean, there’s so many things that go into being a good ISA.
Brooke: So being told no a lot. So if you’re getting told no a lot and you’re having a conversation with the same person telling you no 30 times, how do you overcome that just a bit and not think, like, you know, because I feel like I get the objection – I’ve even had these thoughts before – I don’t want to bother them or I’m going to lose their business if I call them again or whatever. Like, not very many people call someone 30 times to get a yes.
Caleb: He feeds off of that.
Brandon: Yeah, there’s something about it, like a mentor of mine, or an older guy that was in the office when I first started, told me one time that complacency kills. And when I say that, I pretty much mean that if you have that drunk monkey in your head saying I’m going to call these people and it’s going to annoy them, you just have to change that and realize every no is going to get closer to that yes, and pretty much, no means not yet. Especially in this business, somebody’s always going to be interested in selling a few years down the road. Now, it’s important to not call those people and waste time on them every couple of months, but yeah, it’s just – I just enjoy it weirdly enough.
Brooke: It’s just a mindset. It’s a total mindset shift. It’s how you look at it.
Caleb: He makes just such good friends with the people though, Brooke. I mean, I’ll go on these appointments and they’ll be disappointed that it’s me coming instead.
Brooke: You know everything about them, which is how you build a rapport and how you get people in the door in the first place.
Brandon: And to build on that, when I’m calling these people all the time, I’m not asking for business. I know there are some people that say you should ask for business every time you call, and I don’t agree with that, but I just want to find out as much about these people and connect with them on a deeper level than real estate. You know, at the end of the transaction, I want them to be friends or they’re going to call us or refer us to other people. It’s more about – you can start building relationships in this job and sustaining those relationships, then you’re going to do great.
Brooke: So that’s also, I mean, you have to have patience in this industry, especially with what you guys are doing and the approach that you’re taking, I agree with you. It’s finding that balance too of, like, building connection and rapport with people and then also asking for the sale, but not doing that too quick, which I think, in our industry, it’s so easy to get caught up in, like, I want. Like for example, Caleb, when I first met you, I was in awe. It was probably two or three years ago, maybe even four years ago. I was like, how the hell are you so successful with such a short time in the business and so young? But it was just doing the work, being consistent. I mean, you always have big goals too, right, so you’re just not getting caught up in that end result of, like, I need it now, or this sale needs to be mine now, and then you get kind of lost in that mindset as well.
Caleb: Yeah, I mean, I’ll tell you, I learned that lesson the hard way early on in my business, to where if people didn’t list with me, I’d get all pissed off and, I mean, I was almost rude to them when they’d call and break the news to me or if they’d ignore me. And I’ve just learned to let it go and wish them the best of luck. And a lot of times, people circle back to you. I mean, that mistake alone has made me probably over $100,000 since I fixed it and it lost me over $100,000 before when I would just pretty much tell the people to screw off when they told me that they weren’t hiring me and they were hiring somebody else.
Brooke: It’s that all or nothing approach, when you have it in your head, of like, “If you’re not going to list with me then fuck you.” So what do you think sets you guys apart, because there’s a lot of agents? In my market alone, in Madison, Wisconsin, there’s over 3000 agents in my market and when people ask you what makes you different from your competition, what is that? Or even within your team when you guys are having conversations or if you have a really tough competitor going up against, what is your hot sauce? What makes you different from the rest of the people in your industry?
Caleb: I mean, there’s a bunch of big teams in our market and Charleston is super, super competitive. But the big teams are just a lot of bodies, as far as they have a lot of team members. But we’re four licensed agents that are doing 225 to 250 transactions. We have real estate warriors on our team, basically. We’ve got really highly trained people that are doing – I mean, our top agent will do almost 60 transactions. So you’re getting a lot more high skill than just – how do you put it?
Brandon: We’re lean.
Caleb: Yeah, we’re lean and we’ve got a bunch of warriors versus these big armies of just bodies. Does that make sense?
Brooke: It makes total sense and it makes – I mean, the next question I was going to ask was basically based on team building and how you’ve been able to create a culture and build a team and get people in the right places so that you have systems and strategies and you’re able to do more production. And one of the biggest lessons that I’ve learned recently is that bigger isn’t always better, for one. And then, I have a lot of conversations with agents in the marketplace that ask me about my team or the structure or, you know, they’re wanting to build a team themselves. And what I see so much in my market is you have these massive teams that literally have, you know, four people coming and four people going every single month. It’s just a constant turn them in, let them go. And then you also have the teams where it’s like, we’re a team but everybody’s doing the same job. Everybody’s, basically, an independent agent but calling themselves a team, they’re all doing transaction management. They’re all doing the entire process. So when you set up your team, and you do have warriors on your team, what has helped you build that culture and get the right people in the right places and keep people, retain people, retain the good people?
Caleb: Yeah, so I mean, I think that’s what makes us who we are. As you know, you’ve been here a couple times, we just got a really close-knit group, but it’s been work to get there. We’ve let some people go. We’ve had a couple people quit, but I think it was – you build your team on the frontend and hire. We hire for our culture now, versus just hiring people because we like them or versus if they’ve got good experience. We’ve made some mistakes and thought we hired some rockstars that just didn’t fit our culture and they’re almost like a turd in the punchbowl.
Brooke: Yeah, it’s like you get everybody rolling on the bus and then the wheels start falling off because of the one person that’s not a good fit.
Caleb: One cancerous person in the office. Now, we bring people in and they have to go through an interview process where they interview with three different people on the team, and if they get three yeses then I’ll sit down with them and highly consider them, and if not, if they get two out of three, that’s a no.
Brooke: Now, what about profiling? Do you profile the agents that you bring on in terms of strengths and weaknesses and all of that, or do you really look outside of just what they score on a WizeHire app or whatever you’re using? I mean, I profile people out, like multiple different platforms I’ve used and I’ve realized too that there more to just a profile.
Caleb: Yeah, we use DiSC, but what I’ve found is if they go through three people and don’t get three yeses – I like to have them interview with the rest of the team first, if possible, versus me wasting my time with interviewing someone that’s just not a fit. You know when you sit in front of someone and you talk to them for about 30 seconds and you know that’s a bad fit, but you also don’t want to be rude and kick them out after about a minute and a half. So that weeds them out and it only gives you the best people to interview at the end of the day.
Brooke: And it’s a process. For anybody out there that’s starting to do hiring, it for sure is a process. And it’s also a process that I think you have to figure out for your own too, because you’re the one building the culture. So your culture isn’t the same as my culture and understanding that and what you really want and what you’re building, I think, is key as well.
Caleb: yeah, what do you think?
Brandon: Well we’re lucky. I mean, everybody that’s on our team, we – like, I moved down here from North Carolina. I knew Caleb’s cousin. Me and Justin, we grew up together and, obviously, him and Claire are brothers and so they were cousins. I mean, when we first started, there was six or seven of us. I mean, we all knew each other and as we’ve grown, most of the people that are on our team now are people that we actually, like, know. I think Caleb can agree that, like he said, we don’t necessarily hire – what we do is we hire people that we like and we know and then teach them real estate. It’s all about figuring out, do you have drive, are you disciplined, and are you dedicated, and then after that, it’s just giving them the opportunity.
Caleb: Teaching them the skill set is the easy part, but they have to want it.
Brooke: Right, well you guys have a good leader as well, I do have to say.
Caleb: Yeah, and I’ll brag on Brandon a little bit. It’s funny, he actually started on our team as a closing coordinator, an assistant closing coordinator, and he fucked up everything. I mean, he would put things in the MLS wrong, he’d send things, he’d send things to the wrong attorney, and he drove our closing coordinator at the time just off the wall. So did we let you go? Or what did we do?
Brandon: Yeah, so they let me go for like a month or two and then I found out that another kid got an ISA job over me – well not over me, I never really interviewed. But I moved down here for that purpose, within the first year, I wanted to be in real estate somehow. So another buddy from back home called me like, yo, I’m moving to Charleston. I got a job. I was like, what? I was pissed. I was talking to Justin, like, this is bullshit, blah, blah, blah. Anyway, I’m still here. That guy’s been gone for like two years now, but I honestly wanted to prove Caleb wrong so bad, that’s what started it.
Brooke: And you’re a rockstar. You’re amazing in the role that you’re doing.
Caleb: Oh, he crushes it, but the thing is, sometimes, if they’re a fit for the culture, that’s what you want. Because he was a fit for our culture but he wasn’t a fit for that seat on the bus. So he was just in the wrong seat. But once we put him in the inside sales role, I mean, I would put him up against just about anybody in the country.
Brooke: I love that, but you had to want it too, and that’s what makes you so great at an inside sales position too. You got pissed off because someone told you no, or that you couldn’t do it.
Brandon: Yeah, it’s funny, I used to have a sign – I still do – right above my computer on the wall. It says, “Every no is closer to a yes.” And when I first started, what I would do is – we used to have co-realty and we would just download neighborhoods and I would just call through every neighborhood in Charleston and ask them if they wanted to sell. And I got a no, and every now and then I got a maybe, so they’re in my pipeline. These are the people that I’ve been following up with for two and a half years now and that’s just what it takes, in my view.
Brooke: Yeah, you do a great job. Okay, so to finish up our chat today, what would you both say has been your biggest struggle in this business so far and how have you overcome it?
Brandon: I’ll go first. It’s just really weathering the downtimes. I mean, anybody in sales will tell you that you have a great four or five months, and then there’s two months where things are up and just being in a slump. I mean, figuring out how to get out of it and all that stuff, that’s what I would say; keeping a good attitude through that, not getting down and just knowing that things will be okay in a few months again. But it’s hard when things are going bad, that’s my biggest struggle, just bouncing back.
Brooke: it’s the roller coaster. When we’re high, we are so high. And then when we’re low, we’re at the bottom.
Brandon: Yeah, at the bottom, you think you’ll never be at the top again. It’s a horrible feeling, especially being 100% commission.
Brooke: Okay, awesome.
Caleb: I would say, I had a mentor, Jay Kinder, that did real estate coaching and still heavy in the real estate industry, but he said that – he always kept telling me that there was a two by four that was going to hit you at some point in your career. And I’ve had that two by four hit me a couple times. I can sell, and I’ve always been able to sell, and I think that’s been one of the reasons why we’ve been able to grow so fast. So I can always generate income, but it’s the things that you don’t see coming that will just beat you down and put you in one of those slumps. I mean, I’ve had employee issues with lawsuits – I won’t get into any of that. But protect yourself with good employment agreements.
Brooke: And you don’t think of that shit until it does hit you in the forehead, and then that shit is real.
Caleb: Then it hurts. I mean, luckily, I can sell well enough to where I’ve been able to dig myself out of it by just generating income. But for those of you out there that are not generating a lot of income and you get hit with a lawsuit like that, it can put you out of business. So that’s one – I mean, I’m a high-risk-taker too, so I just made a bunch of mistakes that have cost me a lot of money over these last four years. But I’ve also taken risks that have paid off.
Brooke: Yeah, I was going to say, that balances out. If you’re a high-risk-taker, you have to be willing to weather the storm when things go south. However, a lot of your success, you likely wouldn’t have if you weren’t a high-risk-taker and taking chances on some of the things that you have taken chances on.
Caleb: Yeah, but I’ve learned over time that you can protect yourself with insurances, with contracts, with employment agreements. I mean, there’s a lot that you can do to help, at least put preventatives in place to, I guess, protect yourself.
Brooke: Sure, okay, awesome. Awesome advice. Do you guys have any other advice that you would give either agents just starting out or just scaling teams or maybe people that have already seen incredible success, just within the industry, or even entrepreneurs in general? Do you guys have any closing advice that has really changed your life?
Caleb: I mean, if I could give anybody any advice, it’s to go buy the book Miracle Morning by Hal Elrod. There’s one for real estate agents too, but it just sets your day up for you. It talks about waking up early, going to the gym, reading, meditating, journaling, just setting yourself up for success before the morning even starts. I mean, I think that’s what’s gotten myself – and a lot of our team members do it now too, and if you want to be successful, it will help.
Brooke: I’m on the same boat with you on that one. It takes time also, dedication, and accountability to get your ass up at 4:30 in the morning.
Caleb: It takes discipline.
Brooke: Yeah, Brandon, what about you?
Brandon: I was just going to say, when it comes down to it, you’ve just got to do the work. Like Tom ferry says we often let the drunk monkey – which is what they call it – get in the way and we all have these thoughts of, like, they’re going to say no, they’re going to hang up on me, they’re going to – for my role at least – they’re going to kick us off the phone. And you can’t let stuff like that get to you. Just move on, do the work and you’ve got to envision what it’s going to look like six months down the road from doing the work now. We’re not going to get anywhere; I’m never going to be who I want to be if I’m not doing the work now.
Brooke: yeah, love it, cool. Well thank you, guys. I love you both so much and I really appreciate you coming on and giving advice to everybody. I always get something more out of it as well. You guys are awesome.
Caleb: Awesome, we love you.
Brooke: Alright, thank you. Have a great day and thanks for being on the show.
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