Give Yourself the Work

I ended up in technology based on my identical twin sister's skills. Hold on, explain that. They looked at me and said, "You're hired." I could not type. There's something that you never publicly spoke about. Back in 2007, I almost lost my house to pre-foreclosure. And I'm a real estate agent. Tell us about that. Well, I called my mortgage servicer and I said, "Hey, I am not going to be able to pay my mortgage next month."

How do you keep them going when, like, deals aren't happening yet? The hardest part about being an entrepreneur is I have to give myself the work. I'm going to manifest this business, but not working at all. Now, I do believe in positive confessions. I do believe, but you can confess every day, but you still got to work.

Welcome to Outside the Corporate Box. I'm JMan, alongside Jeffrey Scott Stanton. And this episode is brought to you by our founding partners, WiseAgent, Subi, and The CE Shop. These are the companies that believe in what we're doing here. We're grateful to have them in our corner.

The playbook is changing. The question is, are you changing with it? This is Outside the Corporate Box. Real conversations with real leaders who broke the mold and built something better. With your hosts, JMan and Jeffrey Scott Stanton.

She walked away from a tech career with small kids at home, no safety net, and a business plan that existed mostly in her mind. Twenty-nine years later, she's a managing broker in three markets, a national speaker, and one of the most trusted educators in real estate. This is Outside the Corporate Box, and this is one of those conversations.

So, today we're sitting down with Carrie Little. She's a managing broker in Illinois and Florida, the founder of Smart Girl Media, a national speaker, a best-selling author, and one of the most recognizable voices in real estate technology and education. But what I really want to get into, or what we want to get into today, is how she built all of that while the industry was still trying to figure out the internet. Carrie, welcome to Outside the Corporate Box. Well, thank you for having me. I'm glad to be here.

Well, let's go back to before real estate, the corporate box, right? Because it's outside of the corporate box. So, you were working in tech, not just casually — like, we're talking NEC Technologies, national training gigs, television productions. Paint the picture for us.

So, I could go way back. I ended up in technology based on my identical twin sister's skills. She worked — Wait, wait, hold on. Explain that.

So, you know, right out of high school, I was a young mom, and I worked for a company called Sears Roebuck and Company — if you haven't heard of them, they're gone. Yep. But then there was the Sears Tower. So, I worked for Sears Roebuck and Company, and my last job at Sears was in custom decorating. But a fun fact is, I used to actually — I don't know how to make clothes now — I was a clothing designer all the way through high school, and that's what I went to college for.

But when everything shifted and I became a young mom, when I was in the custom decorating department at Sears, I wanted to do something different. Now, my twin sister worked for a company here in Illinois, and she was a temp agent. Now, when the temp job ends — she left, and usually these temp companies don't want to hire you because they have to buy out the contract. So, she already had a new job. They called her and said, "Hey, we'd like to hire you now." And she said, "I'm sorry, I already have a job, but I have a twin."

I literally went to the interview, sat down, and they looked at me and said, "You're hired." I could not type. I had to go and take a typing class at the local college, and I'm kind of glad I didn't do it in high school, because they used to do it on typewriters and IBM Selectrics. I learned on a computer. So, that is how I ended up in tech.

So, what was that job for? What was it for? It was Kasian Business Systems. They used to actually put together the computers for a company called Boston Chicken — Boston Market now — and McDonald's Corporation. Very cool.

So, I became an admin to the vice president of the company, and I couldn't type. And I was doing their billing. I was working with their — I want to say the department that actually went in and repaired the typewriters, the computers. And so, again, I couldn't — I didn't even — I knew how to write a letter, but not type one. The vice president literally coached me through my entire job. And that's how I ended up in tech. And then from there, I went to NEC Technologies.

And then from NEC Technologies — because I was a volunteer at the church. I always say I used to edit for a nonprofit, but the truth is, churches today, you see big mega churches. It was a large church. I used to volunteer and actually edit television and work big cameras.

Where did you get that skill set from? Church. They trained us. And here's the thing — Joel Osteen actually came to our church to put our systems together better, before he became the pastor in the church that he pastors now. Very cool. So, I used to edit on an Avid. You know, we could talk for hours on tech, but that is literally how I ended up in tech.

I'm just saying, you, like, little Joel Osteen — like, Joel Osteen came in and they just, like, throw that out. It's like name dropping without name dropping, right? But that nonprofit show that ran on, like, Channel 9, TBN — like, that was kind of a big deal, right? Yes, it was.

It was, because I actually used the cameras first. I had been to the NAB, or whatever the broadcasting conference was, in Las Vegas. I literally learned hands-on how to edit television, and it was broadcast to the Total Living Network, to Central America, and through WGN. Very cool. Things you learn that you didn't know.

How long did you do that for? So, let me think. It had to be — it was before — so, around maybe '97. Okay. Let me think. Let me go back, cuz Lauren — '99. Yeah, around '97-ish. And that's kind of how I ended up a little bit in real estate around that time, because I was working for the local church, and then I decided to buy real estate, and that's how I ended up working on the weekend for a builder. And that's what pushed me into real estate.

So, tell us about that. So, you go from, yeah, pretty much as we said, inside the corporate box, to having, you know, a 9-to-5 or a paid job where you get a paycheck, and then decide to buy a house and get into — it's weird, cuz a lot of people do that. They decide, "I'm going to buy a house." They have either a bad experience buying that house, or they realize, "Hey, I can do this better." Or realize, "Hey, maybe I can save some money." Why start doing real estate on the weekends? Yeah, small kids at home.

So, first of all — now, cuz I'm still involved in the church — one of my friends that worked at the church, she was a real estate agent, and we started talking about it, and I'm like, "I want to buy a house." And so, she started talking me through the process. And, you know, first of all, I decided I wanted to buy a house because I was sick and tired of paying rent. And at that time, I only had one kid at home, who was getting close to the age of nine. So, a little easier to kind of volunteer to work full-time at the church and work part-time with a builder. I ended up buying the house, and then I was still working on the weekends for the builder.

And, you know, I know every state is different with their license law. You can get a referral fee when you refer people to buy. But it was only, at the time, up to about $1,500, and I probably sold more new construction, and I wasn't getting paid, because I was the host. I was the person that would say, here, fill this out, and then you would work with a sales rep. I was the one driving in my car to open up doors, and that was what drove me to get to the point where I wanted to get into real estate.

Now, back up — the person that ended up helping me buy was also a very prominent real estate agent, and she was an educator. So, she's the one that helped me get into the real estate space, and of course, now she's an attorney.

So, you went from the production space to production, to a builder, and being the door opener, or, you know, registering people, and almost like an unlicensed assistant at that point. Yeah, I would say, but really, all I was doing is welcoming you in, you know, saying if you had any questions about the models, I would tell you where the models were. I could show you the lots, but I couldn't sell it to you. But I was the one that was selling it, because I had bought in the subdivision. I knew more about the subdivision than the people that were working there, because I was vested. Yeah, and most states, they actually let you — if you're directly employed by a builder, you can do all that stuff without being licensed.

So, were you still doing the production, everything for the church, at the same time? Yeah, that was during the week, and so yes, I was still, you know, editing television. And then there was a pivot, because in '99, during all of this, I was about to finish my undergrad. So, in '99, I graduated from college. I was still kind of working part-time with the builder, and then I stopped working at my local church full-time because I wanted to be more available for the kids.

So, I was working for another church, where I learned more about finances, more about creating their brochures, and then I had an opportunity to get licensed. So, I was working part-time at a different church, got my real estate license, and I started selling real estate. So, I had one goal, and it was only to make $60,000 a year and take my kids to the swimming pool every summer — cuz this is 2001 — and be available for them when they went to school for sports. That was why I got into real estate.

So, what was it like leaving, like, Black Diamond Road, guaranteed paycheck, versus going into real estate? So, first of all — and I might be a little more driven than others — I had in the past hosted trade shows for creatives and things like that. So, I was used to trying to figure out how to make extra income. So, that wasn't a fear for me. And I did have a dual household income, so that helped a little bit. But I knew I wasn't going to have the same income.

What I do have the gift of, which all of us do as instructors, is the gift of — I like to talk. And back then, we didn't have — we had email, but — and if we think about our phones, I had, like, a BlackBerry. We weren't calling people. But what I did do good at was having homebuyer workshops and telling everyone I was about to get my real estate license: don't do anything. And lucky enough for me, they weren't smart enough to say no, so I had closed three transactions before 9/11. And I thought, this is the best hustle ever.

And I had a goal, and I don't know, you know, how people think today — well, I kind of have an idea — but if you have a goal — and I had a goal of, I wanted to pay off some debt. I literally knew if I made 60,000 — and back then, and I know there are all different kinds of models, but you know what those models were like when you started selling real estate. So, you know, if it was 16,000, how much I was probably making. That was my goal, so I could get out of debt fast, and so I could be available for my kids. So, I was really motivated. I was walking my neighborhood. I was doing homebuyer workshops at least once a quarter.

So, in your first 90 days, then, you knew you were in the right business, right? Like you said, like, the people business — you're good at talking, you're driven, you have a very specific goal. Like, what specifically happened in those first 90 days? Cuz a lot of people are like, "Oh, I did it for a year and I struggled, and I didn't do—" Yeah, "I dabbled," or, you know.

For me, it was, I had to make it work. And so, first of all, I remember going to the local college to take the real estate licensing class, and once I passed the exam — right, even before that — I had called everyone I knew. Cuz we weren't texting anybody. We weren't emailing anybody. Saw you at church, and I'm like, "I'm getting my license." They're like, "Okay, I'm thinking about it." So, within my first 15 days, I had a listing. And then it closed 30 days later. And then everywhere I went, when I talked — Like, "Yo, this is easy."

I think it can be like that for everyone. It's just, people are afraid of making mistakes, and I wasn't afraid to make a mistake. You know, we have people that come to class, they show up, and they're the smartest, brokest agent, because they won't, for lack of a better statement, pull the trigger. And I asked. And when someone was like, "Well, you're new," I'm like, "I'm new, but I got this broker over here who's helping me. And if I don't know, I'm going to go ask." And just like, you know, they trained us to say, "You want me cuz I'm more motivated, cuz I don't have any clients."

And it's weird now — you said that — it's weird now, because if you told an agent to go out there and tell someone, "Hey, I'm motivated. You should use me cuz I don't have anybody else," that agent would be like, "No, I can't say that. I can't say that." But to me, that's the truth. Like, I always want my salesperson hungry. Like, people always say, "Oh, I want the top producer." To me, a lot of top producers aren't hungry anymore. It's that scrappiness, for lack of a better word. It's that hustle that I think, "Hey, this is my goal. I need to do that. $60,000. I need to pay off these debts." Me, I want somebody that's hungry, not somebody with a—

And, you know, what's interesting about that is, there are a lot of people that only want the top producer. Just like you said, and I'm good with that. And, you know, there's always a story, and I have permission to share this one. My identical twin, when she was in Illinois, her husband at the time didn't want to hire me because I was too new. And I was like, "Fine. I'll get the top producer to come list your house." Because I knew I could make an income by referring.

And so, they had an open house to interview people. And so, of course, they hired the person I sent — and she's still a top producer today — they hired her. But guess who brought in the buyer? You.

So, in my mind, sometimes you do have to prove yourself, especially with family. But for me, when it comes to family, I'm like, "You don't have to hire me. But this is how I make a living. So, if you don't want me in your business, allow me to refer you to a producing agent, because you're going to call me to complain about them anyway. So, you might as well allow me to get paid from it."

I like that. You're going to call me anyway to complain about whoever you pick, so you might as well at least let me have you. I like that. I really do. Cuz it's real and authentic, right?

And even — cuz now she has purchased in California, and I referred her to an agent that volunteers. And when she received three offers on her property, she was like, I got an FHA, and I got a home sale and a home close contingency. I don't think I should take this FHA. I'm like, what? I said, tell me about the FHA. And she was like, well, it says they're fully underwritten. I was like, you're taking the FHA, because they're fully underwritten and they can close, and you don't have to worry about contingencies. So, that's why you want me to refer — because I'm a backup to helping, coaching you through the process, because I'm family.

So, you said coaching through the process — where does that come from? Because a lot of agents and a lot of brokers aren't into the, hey, I'll coach you through the process. Just, this is what the process is, do what I say, and now walk away. What do you think that ability to educate — and I know you're an educator, like we are — so, where does that come from?

I think it comes from — I'm the person that things didn't come easy to in school. You know, I could say, unless I was using my hands. I was really good at — loved PE, loved wood shop in high school, and I love sewing. So, when someone would take their time with me and make me not feel uncomfortable, it made the process so much easier. So, you know, I can tell you what to do, but I've learned, if I coach you through the process and give you what you want, not what I want, you are more likely to refer me later.

And I'll say this — I just had a transaction, and, you know, my husband gets mad at me when I say this: I typically don't sell, because I manage. I manage agents. But there are times when I come back outside to sell, because it puts me in the business so I can see what's happening. And I had a transaction where we were the largest house in the city. I knew we were testing the market, but I had done all of my research. And the owners — they could have picked someone else with the company, but they picked me.

And so, I knew I had to provide more value — but you want me because I'm an instructor, because I'm in the tools every single day. And so, when we got an offer, I think they wrote the offer based on what we negotiated, hoping that it wasn't going to appraise. But I'm like, you got me. I train the appraisers in my state. So, when it came in a little bit lower, who went in and did an appeal? And who won the appeal?

So, it's weird. I'm going to back up. This is totally off script. So, you said, like, going through school, you liked to do the hands-on stuff. And you also said you like to educate people and walk people through the process. And you explained about learning how to type, and that the boss, the executive, helped walk you through that process and learn how to do it. And then you talked about the studio, and, you know, Joel Osteen's team coming and setting you guys up and walking you through the process.

To me, that's what I said — you know, this is all outside the corporate box. There's a theme there. And I think a lot of times we realize it, or don't realize it, that that step from that corporate box gives us our foundation to actually do what we do. And I told them the same thing — into real estate, you can do what you want in real estate. So, what do you think that skill set actually is, from what you did previously? Like, you were tech. Like, how does that come into it? How does all the things you've done in the past bring into making you successful now?

Everything you've done in the past helps you today. Cuz, I mean, I am very tech-savvy by mistake. You know, I just kind of got lucky because of how they hired me. But, you know, the things we didn't talk about were — you know, I used to work in retail. I used to work in custom decorating. And when you hear the word custom decorating, what does that mean? I was the person that sat behind the desk that looked at the measurements for shades and blinds and draperies.

And then I was the person, even in my high school, that actually worked with the teachers, because I worked in the tailor department. So, I understood processes, and I understand how to finish. And so, you know, when you bring back and tie in all of the corporate and those processes, it does help in the world of real estate, because I learned how to write a letter. I learned how to use Microsoft Excel. I learned, you know, even in my master's degree program, how to use SPSS Modeler or SAS — things that we can use in our businesses today. So, being able to go back and look at all of the processes I learned, I'm sure, has definitely shaped the way I run a business and a company today.

You know, it's funny, cuz we talk a lot, when we do trainings, about, like, take your background from what you did prior to getting into real estate and put that real estate spin on it. And I know a lot of people listen to this maybe thinking, hey, I'm listening to this cuz I'm in the corporate box, and I want to start real estate, or I want to start my own thing. I think you need to understand what your skill set is, as you explained it, prior to getting into real estate, and that's why you're good at what you do. And I think that's almost like an epiphany, eye-opening, to a lot of people, to realize, like, "Hey, you know, I was a tennis instructor. What does that have to do with anything?" You can find what that has to do with it.

Yeah. And, or even just, you know, I've had people say, "I don't know anything about real estate." And I'm like, "Have you walked in a house? Have you lived in a house? Have you walked past a house?" You know, my grandmother used to work for a builder as an administrative assistant. So, because she worked for a builder in the city I grew up in, it helps me have better conversations. My mother is a history buff and knows everything about the suburban marketplace — I wouldn't say marketplace — of the suburbs outside of Chicago. And so, when we have conversations, I can remember who built what, what used to be a swamp.

So, family — everything you've learned from your parents, everything you've learned, you know, playing with friends, how you played, to, you know, just working. Listen, if you worked at McDonald's and somebody threw a hamburger at you, and you didn't react, you got a special set of skills. I don't want to say that one — hamburger — You have patience, and you can overcome challenging situations. Right. Because I've worked at McDonald's, but never in the store. I worked in corporate, in the East Coast real estate division. So, I've been — I catch that burger. You name it.

And JMan had a story about a slippery chicken that's similar to that. So, I'm going to — JMan, tell me about — one of the questions. What point did it all start making sense, and, like, "Hey, this is me. This is my calling. This is what I'm going to do as far as real estate." And, honestly, to me more importantly, when did you start — like, do you consider yourself an entrepreneur?

I probably consider myself an entrepreneur as young as being a kid, cuz, you know, my twin sister and I would always talk about teaching. We would always try to sell things, you know, from the lemonade stand to — again, when I was in high school, I was a cheerleader, and because I knew how to sew, I was the person that made all of the uniforms for our cheerleading team, so we could go and compete every summer in summer camp. So, I can't say I knew that I would be an entrepreneur, but I was always trying to do something different.

Are there days when I wish I was born, you know, like, 15 years ago? Because this next generation has so much opportunity, because they have access to social media. Everything is so much faster. Now, I'm not complaining about when I was born, but I truly believe that if you get into real estate today, and you just tie in what you've learned in the past, you have so much more opportunity, and you can do it a whole lot faster than we did. Cool. So, yeah, I think easily I could say that I was probably an entrepreneur, you know, as a kid. I was selling something to somebody.

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Well, and when you say identical — I ran into her sister at a conference, and I thought it was Carrie. I was like, "Girl, what's up?" She's like, "Hey." I'm like, "Hey, who are you?" I was like, "Why are you being weird?" She had no idea. It was identical. It was funny.

Yeah, and I'll say, there are some positives about having a twin. So, over a year ago, I was supposed to speak in California, and I got the flu during our state business meetings. And she lives in California, and my twin teaches tech, and she, you know, she knows how to code. And because the talk was going to be on AI, I was like, "Hey, I am not getting on a plane. I am so sick, but my twin is, like, 20 minutes from you. Can she come speak?" And she went and did my talk.

Did they change the name on the billboard of who was presenting, or did they keep the same? They did. And she even went to the installation for the incoming California president — not for Women's Council — and people were coming up to her, hugging her, like, "Hi, Carrie." And she was just like, "Yeah, whatever. We're just going with this."

I was with JMan — I was with you, and you didn't jump in this question over here. Well — Okay, I lost track of where we were along the book we were covering, cuz I just randomly ask questions. Yeah, let's talk about money then. Specifically in those early years, you said your biggest stress was not having the money to start. So, what was the actual financial picture? What were you working with?

To get started in real estate — first of all, most agents don't realize how much it costs to start, although it is one of the lowest barriers to entry. So, I did what a lot of people do. You know, first of all, I decided I was going to take the course. So, I called my mother. And I was like, "Can you pay for me?" She's like, "Sure." And then I passed the exam, and I found out I had to pay the brokerage, I had to pay the association, and I had to pay for my license. So, what did I do? I called my mother.

So, I can say that there was that benefit, but I didn't really have money to do marketing. So, I really did get creative, and that's why I did the homebuyer workshops. And I'm pretty savvy. I already knew how to use PowerPoint, things like that. So, what I would do is, whenever I would do a homebuyer's workshop, I would have a loan officer — and in our state, we use attorneys — I would have an inspector, and back then we had Partners in Charity and the Nehemiah program. Yep, I remember that. So, I would make sure they all did the talking first, and then I would sum it up, and that's how I would at least have two or three transactions.

And not having money — at the brokerage I was with, they allowed us to print, and it didn't cost us anything extra. So, man, I was killing a tree. Forgive me. And let's be clear, I am sure I was violating rules. So, I'll give you an example. Now, all my marketing was in compliance, cuz I did show that information. But, like, I was going into apartment complexes, putting flyers out. But when I learned, okay, you can't do that, I would go to the laundromat, and I would put out flyers. I still have this flyer: warning, renting is hazardous to your wealth. And I would have the little tabs at the bottom. That's good. And I had closed deals from the laundromat.

And then, in my townhouse subdivision, I walked my subdivision every single month until it got really cold, and I was the go-to agent in my subdivision. And again, in my mind, I just wanted to make about $60,000 a year. To me, being a top producer didn't matter. I just cared about, you know, making sure I was available for my kids, and we were making a living. Some people have to be number one. I don't ever have to be number one.

Well, and I think there's a gap that a lot of entrepreneurs know, like, especially coming from that corporate box, where you got your license, nobody said, hey, save money, create a business plan, have six months — like, if you went to business school, you would know that, but if it was the corporate box, it's like, oh, I'm going to get my license and get this. So, that gap between looking successful on the outside — which, so many, we see these agents, like, I'm rich, but really they're like — like you said, if they're successful in the beginning, you got to pay for signs. You got to pay for your advertising. You got to get stuff. And you had a mother that would help you, but, like, tell us a little bit more about that.

I mean, luckily for me, you know, I worked for a brokerage where the signs — you just ordered the sign, and it was a standard sign. And I would say, for me, not having to pay for signs — what I did have to pay for was direct mail, and, if I had a listing, to put it in the newspaper, cuz we didn't have social media. So, what I did pay for was marketing. But I learned that if I went to Uline, uline.com — now you can go to Amazon — I would buy the doorknob bags. I stuffed the bags, and I walked, and I talked to the neighbors.

And I went to Bible study with the moms in the area. I went to Mothers of Preschoolers. I was a co-chair of the DuPage chapter of Mothers and More. I did the things that put me in groups. And by the way, I didn't get into those groups because I wanted to sell them real estate. I got into those groups because I had kids. Being able to tell them about real estate was a bonus.

So, even today, just, you know, going to the swimming pool, going biking with your neighbors, working out with your neighbors, walking the neighborhood — you know, even today, we don't do doorknob bags, but I do mail to the neighborhood. People know that we're real estate agents in our community. So, I would say, if anybody didn't have money, I would pause and say, either what can you stop spending money on, or how can you make sure the people in your community know who you are? Cuz you could easily have people over for coffee.

Yeah, find a way. I like that. Because it's like, you can't afford direct mail? You know what I can do? Take some bags and put them on the doorknobs. Now I'm saving money. It's the sweat equity.

So, I was going to jump us ahead a little bit. So, when did you decide to become a broker? Well, I always said, I'm going to get my broker license. In Illinois, we call it managing broker now, cuz we like to do all things different. But I decided to do it for — in the event I needed to.

And I remember — so, I was licensed in 2001. Around 2007, I passed a broker license. And then, around 2016 — and Mark can tell his story, but he didn't think he could get a license. And so, one day he said, "I will get my license if you hold the license." He said, "You're not really selling as much anymore. You're teaching more. And why are you paying the fees?" So, I literally opened the brokerage for my husband, because when there were times I needed help, he couldn't help me. So, that was around 2016. And I had a strategy. I had a 12-month exit plan.

What do you mean, 12-month exit plan? When I decided I was going to open a brokerage, I started preparing the website, the social media. I opened the company. I knew when I was going to exit. And I'll just say, when you are with a big brokerage — I needed to have new emails set up. So, I was forwarding emails to the new email and replying with that email, because many brokerages — and I know it's different now — when you use their client relationship management tool, CRM, they own your data.

And so, I knew when I did exit, they were going to still be marketing to my network. So, I wanted to start the offline networking with my own database and a new email address. So, I had planned for 12 months to leave. And that's when I started the brokerage, and then Mark got his license probably four months later.

Okay. I think that's really smart. I think a lot of agents, like, right away jump ship without putting much thought into it. They just said, "Hey, I'm doing my own thing," just cuz a deal blew up, and they fight with their brokerage, or whatever it is. And all of a sudden, it's like, "Oh, now what do I do now?" So, having a system in place, I think, is really—

And what's interesting, that you say that — when I opened the brokerage, it wasn't to have agents. But when I opened, all these people are like, "Carrie, I want to come to you." I'm like, "Wait a minute. Wait. Hold on. Hold on." I wasn't ready. And I did take on a super producer and an admin at the time. And I'm glad I did, because it made me go and build all of my standards of practice.

But to step back a little bit, that's why I'm involved in real estate. And when I say involved — that's why I show up in person to the local, state, and national events, because it helps me learn what I didn't know. Now, Zoom is fine, or being in an online space is fine, but it made me network differently, and it helped me learn what was happening in the world of real estate faster, so I could come back and educate those in my office. And it made it easier for me to open a brokerage, because you couldn't terrify me anymore, cuz the Department of Regulations had already done it all, and I saw it so much that I knew how to train agents.

So, now you're the broker owner. You start getting agents underneath you. How does it — that's a big shift between, hey, I'm doing this for myself, and I'm doing it with me and my husband, and now I'm responsible for other people.

You know, when you're responsible for other people, that's what makes you continue to show up, to make sure you understand license law changes. And I'll say, I get involved at a level not a lot of people get involved in. But when you are involved, and you're asked to — like, I chaired a committee for our license law rewrite, and that really made it easier for me to educate the agents in the office and help when I'm sponsoring them. So, going from just two people to as many as 50 made me have better standards of practice, made me, you know, redefine what real estate looks like, cuz I am looking at social media even differently.

You know, my agents — I had one agent call me, and he was like, Carrie, you didn't call this other agent, and they're violating license law. I'm like, man, it's Sunday, and I'm in the store. I haven't even had a chance to look at social media. What it did was, it helped my agents police each other, because, you know, I was the social media police with my agents. And I would tell them, hey, I do this to protect you, and I tell you once, I tell you twice, but if you get a violation, it's on you — because no one, if you work for me, should have a violation, because I know too much. At least it should make you pause.

So, sponsoring agents is different. And again, I'm a little bit different of a broker owner, meaning I interview differently. I always say, listen, if you come to me, it's going to feel different, because I am involved at a level that, if you work for me, they think you know what I know. So, you got to show up to learn. And, yeah, you know, I could keep going, but I think that's good.

Well, how do you run your day now versus how you ran it when you first started? When I first started, my goal was, I needed a lead. And what I can say is, I lead generate probably the same. That was always first, because I knew that that's where my income would come from. Now, today, it's a little different — and don't judge me. No judgment. But I do have a sheet of paper. A checklist. Only because I need to see it in front of me, although I do have it in digital format. So, once a week, I print out, old school, a checklist of what needs to happen as a real estate agent, and as a brokerage, and because I'm an instructor.

So, the difference is, I'm more focused and more intentional. And I'm undiagnosed ADHD, and we — I think we all are. I know, JMan. Squirrel. Right? We do not like to be told what to do, and we don't like to follow rules. But I realized, if I gave myself the work, and I kept myself accountable, I was more likely to do it.

So, differently today is, I am not just getting up to do whatever. I am getting up every day on purpose, so I could be done working at a certain time on specific things. Now, is it exactly the same every single day? No. Because if I'm teaching, that day might not, you know, flow that way. But I do know that, typically, on a Monday or a Friday — Friday is my business development day, and Monday is the just-in-case-I-got-to-go-to-the-dentist-or-the-doctor day.

Well, you just said, give yourself the work, and I've heard you say that before. So, when you're teaching agents, do you kind of give them, you know, your wisdom that you've acquired over the years as a broker owner? Like, do you then pass that on to them? Like you said, they're a version of you. They're expecting them to know as much as you do. So, how do you give them the work? Like, how do you keep them going when, like, deals aren't happening yet? Like, I don't know if this is the right career.

So, I learned this the hard way. I like to tell you what to do, but that doesn't work. So, back to kind of what Jeffrey said — I need to know what you've done in your past. I need to know where you've lived. Like, I'm a lifelong resident of Illinois. I might own in Florida and Mexico, but this is where I am. So, I want to know where you've worked. I want to know what you've done. And tell me how you work.

And then, when they're like, "What do you mean?" I'm like, "Do you make your bed every day?" "No." Okay, cuz that tells me a lot about your systems. Do you read? Like, tell me about yourself. And then, when you tell me your day, and it's every day is different, then I ask, "Are you willing to cold call?" "Oh, no, that doesn't sound fun." Okay, do you like social media? "Yes." I ask you a lot of questions, and then I make you tell me what you're willing to do, because once you tell me what you're willing to do, I can structure a plan for you, or help you structure the plan. Because I can tell you what to do all day, but you're not going to do it. But if you give yourself the work, you are more likely to be successful.

My youngest, who's going to be 24, he's an entrepreneur. He's got 300,000 followers on TikTok, makes money online. And I said to him, "So, what's it like being an entrepreneur?" And he was like, "Yeah, a lot of my friends, they quit. They went to college." He didn't. He was like, "The hardest part about being an entrepreneur is I have to give myself the work." And so, you know, he's an entrepreneur. And if a young person can tell me that, they have figured it out.

So, whether you've come from corporate or not, if you know you have to give yourself the work, you will be more successful. It's when you hope for the work that you're wondering, like you said, JMan, why isn't that working? Yeah. Yeah, I'm going to manifest this business, but I'm not working at all. Now, I do believe in positive confessions. I do believe. But you can confess every day, but you still got to work. Got to do the work. It's like, I'm getting into real estate cuz I love houses, I love people, I want to make lots of money, and I want lots of free time. Find a different career. That's what happens.

So, okay, I want to go somewhere I think anyone listening and watching this can benefit from, especially someone who's maybe having a little difficulties right now. And you mentioned — cuz we send an intake out — that there's something that you never publicly spoke about, in this experience of, from the way you were to the way you are now. Spoke about? Oh, I got it. Back in 2007, I almost lost my house to pre-foreclosure. And I'm a real estate agent. Tell us about that.

I was going through a divorce, and I knew that I was not going to be able to pay my mortgage. And I'm in the real estate space. Now, this is right when you were starting to see pre-foreclosures and short sales. So, I knew to pick up the phone. And so, I called my mortgage servicer, and I said, "Hey, I am not going to be able to pay my mortgage next month. I know I have options, you know?"

Cuz I'm a real estate agent, and I have taught any of my clients that are in pre-foreclosure: get a 70-page spiral notebook, get a pen, pick up the phone every time someone calls, and don't be afraid to call your servicer. So, I had my pen in hand, and everybody I talked to, I wrote down the date, the time, who I talked to, what we talked about. And the first call I made, she said, "We can't help you until you don't pay your mortgage." And so, I had to take a deep breath, and I said, "Okay." So, I didn't pay the mortgage, and then I called, and she said, "This is what we can do for you. We can give you a six-month plan where you don't have to pay your mortgage."

Six months came up, and I missed the first payment. I called back, and I said, "I didn't know — I missed the payment." They said, "Okay. We're going to give you another six-month plan." So, for a year, I didn't pay my mortgage. And what many people don't know — cuz I've said to you, I worked for McDonald's East Coast real estate division — that's when I actually went back to work, and that's when I got my broker's license, for the just in case. So, I was doing two things at the same time.

I worked at McDonald's as a legal assistant. I learned so much about commercial and franchises. I was the assistant to about three attorneys, and then, because I was so good at it, I became the assistant to the attorney over that entire department, and then they paid for me to get my paralegal certification through Boston University. So, in all of that, I had to go back to work because I needed to pay the bills. And, for people that don't know, 2008 was the downturn of the market, and so I had to figure it out.

And what people might not know is, when I went to McDonald's, they said, you have to hang your license. I was a temp. And I said, "I'm not hanging my license." I said, "I won't come." And they said, "No, we really like how you work." They said, "Will you sign an agreement that you won't try to sell real estate to anyone here?" And I said, "Sure." And that's what I did.

Do I still have friends from McDonald's? Yes. Did I learn a lot? Yes. Did they pay for me to get my paralegal certification? Yes. Did it keep me afloat during the change of the market? Did I still sell real estate part-time, or some of the time? Yes.

And it was a blessing in disguise, because I was the kid that was closest to my grandmother. And she ended up having to go on dialysis, so I became more available. So, you know, sometimes all things work out for the greater good. Going through the pre-foreclosure, you know, gives me the ability, when I talk to people one-on-one, to help them understand that no one is perfect, and sometimes you go through, you know, those hard times.

Is there a version of Carrie — not now — but is there a version of you that was like, "Hey, screw this. I'm done." In real estate? Just in general, while you're going through the process of, hey, you know, I'm going through pre-foreclosure, this is what's going on. Was there a version of you — cuz I know you well enough that it's like, you're a worker. You find the work, and you just grind it out if you have to. But was there a version that was just like — cuz, yeah, I think we've all been there one time or another, where you're sitting back and you're just like, "Screw this."

I would say, there are times when I get discouraged, and, you know, I have a meltdown. Yes. But I can't say that I have ever wanted to just, like, screw this and, you know, go back to work. There are days when I'm like, "Man, I should just go get a real job." Cuz then you don't have to deal with — you know, real estate is a hard business. Are there days, even today, where I'm like, "Ooh, this is a lot. I'm done." Yes.

But at the end of the day, I know that real estate is where I thrive. Do I have to do real estate for the rest of my life? I would say no. But as someone that's in the space, I think educating and bringing the next generation up, that is something that I could do. But, you know, even in the pre-foreclosure, I didn't give up, because I had kids. And maybe because I'm a mother, it is hard to just say, I give up, because you always have someone that you are taking care of. So, having meltdowns? Absolutely. Freaking out? Yes. But the give up? No.

Is there anything along your journey, relationship, or something that you had to sacrifice, that you go back and think, like, maybe should have done something differently, maybe something different? I would say yes. And now, this is something that I've never even talked about publicly, but my kids know. Because I went through a divorce, I would have done that differently. I'm not saying that I wouldn't have gotten a divorce, but I think I would have taken more time to date differently, and not bring people around, because my kids — we've talked about it. They were like, "Mom, you just move way too fast."

Are they okay today? Yes. Does everybody get along today? Yes. But, if I could go back, I would say, you know, when you're going through, everybody's going through, and sometimes you don't know that you're taking them through the ride with you. So, I would say I would have definitely done that differently, and listened to people when they were telling me. Cuz the hardest part is to hear it from someone else when you don't want to hear it.

You've been a voice for real estate for a long time. '97. Almost 30 years at this point. Is there something you'd go back, in the real estate aspect, that you wish you told the newer, younger version of you? Not something you tell your students, but, like, something you would go back — like, knowing everything I know now — to yourself 25 years ago. What would be the bit of advice?

My advice would be, if you're in the world of real estate, figure out how you can buy property every few years. Do I still own my first house? I have never sold my own properties. Never. I still have them. So, I would say to, you know, my younger version of me, it would have been: when you close a deal, don't just put money aside for your taxes and living and marketing — put money aside to reinvest. So, you know, we probably own more land in Mexico than the United States, and we have three properties in the United States. Oh, wait, no — one, two, three — four properties in the United States. But my younger version would be, buy. Because if I could go back to 2008, 9, 10, 11, 12, and 13, I should at least have 30 properties.

Last question. Same kind of question, but we sit with it at the end of every episode. What is one piece of advice that you would give someone who's about to quit their job and bet on themselves? They're at that corporate job. Maybe they're doing what you did, a little bit on the weekends, and they're like, I don't know. I need this insurance. I need this guarantee. What piece of advice would you give them?

I would say, before you quit your job, ask yourself, where is your business going to come from? Because if you don't know that, you are going into an arena where it'll feel uncertain. And, you know, how hard are you willing to work? You're not going to get extra time. Can you get to the point where you have a team and have extra time? Yes. But it would be, where is your business going to come from? And don't expect your brokerage to give it to you. You have to go build the business.

So, have a plan. I love that. Well, Carrie, before we let you go, where can people find you, learn from you, and get into your world? So, to learn from me, you can find me on YouTube. And if you literally Google Carrie Jo Little, I come up everywhere. And I have pivoted a little bit, because I learned that my friends and family thought all I did was teach. So, if you Google me and you end up on social media, I am now speaking to the public and the consumer about real estate. So, if you want to learn from me, it is smartgirl.media on Instagram. But I would say you can learn from me if you follow me everywhere, and I'm literally Carrie Jo Little — c-a-r-r-i-e, j-o, l-i-t-t-l-e — everywhere.

Carrie, I want to say thank you very much. Always a pleasure. And I'm going to leave it to JMan to close this out. If that conversation hit you the way it hit us, share it. Send it to somebody who's in the middle of their own moment right now. Subscribe if you haven't already, and next Monday, we will see you back here on Outside the Corporate Box.

But before we let you go, we want to say thank you to our founding partners, WiseAgent, Subi, and The CE Shop. They make this show possible, and they are building tools that actually help people in this industry. Check them out — all the links are in the show notes. And thank you, Carrie, for spending some time with us, and thank you to everyone listening and watching. That is not something we take lightly. Now, go out there and make it happen.