From Introvert to Investor: Byron Pillow’s Real Estate Journey Revealed

Dylan Silver (00:01.181)
Hey folks, welcome back to the show. I’m your host, Dylan Silver. Today on the show, have real estate investor, agent, entrepreneur, proud Chicagoan, doing real estate in the southeastern region of the U.S., out of Alabama currently, Byron Pillow. Byron, welcome to the show.

Byron Pillow aka The Smooth Realtor (00:20.557)
Thank you Dylan, pleasure to be here man.

Dylan Silver (00:22.855)
It’s a pleasure to have you on the show here. I always like to start off at the top by asking folks how they got into the real estate space.

Byron Pillow aka The Smooth Realtor (00:31.565)
So when I was in college, I was a freshman slash sophomore when the market crashed. And I was just interested in real estate. I have a degree in the chem, so I was like a numbers guy organized by trade. And I just looked into it then I started looking at how, you know, a lot of people became millionaires and such. I saw real estate was like number one. So my interest was peaked there and I decided I need to make that leap.

Dylan Silver (00:57.695)
And so you were in school at the time. Did you put real estate on the back burner or were you actively looking at deals while you were in school or were you getting a license? How did it come about?

Byron Pillow aka The Smooth Realtor (01:07.853)
Yeah, I did attain my license my senior year of college, but I always was looking at different avenues and such like that. I first heard of wholesaling like my junior year and I actually did my first deal in wholesaling my junior year of college, which was, you know, 2011. And, you know, it wasn’t much, it was a $2,500 assignment fee, but I figured, you know, I did literally maybe 30 minutes worth of work and I made $2,500. I was like, that’s great.

Dylan Silver (01:38.749)
So the 2011 timeframe, we’re right around there, wholesaling wasn’t what it is today. There’s probably a lot less about it, but I’m imagining you heard about it and were listening to maybe multiple sources and trying to figure it out. What was the information that you were taking in to learn about wholesale?

Byron Pillow aka The Smooth Realtor (01:57.772)
So what I did was, I actually, it was two things. One, I met a guy here in Huntsville who had told me he had been doing it for almost 10 years. And I was like, I had never heard of it. know, he had, before he called it wholesaling, he was just saying assignment of contract. So I actually looked into that. I met an attorney, I talked to him. I learned about the structure of doing deals. I learned about double closing. And then I also invested in some training. I don’t know if you’re familiar with Sean Terry.

but I took a Sean Terry course and I got a little bit more deeper information into it so I can learn how to do it more properly and more effectively. And then after that, you know, it was just my people skills which helped me to actually, you know, get there. And then when I would call sellers and I come to appointments, they’ll be like, you look so young, why are you owning real estate and stuff like that? I’m like, well, you know, you gotta start out somewhere, you know, and it kind of just took off from there.

Dylan Silver (02:52.307)
You know, I tell people this. If you’re an effective communicator, if you like to talk to people, real estate’s your game. And if you don’t like to talk to people, you might also still be looking at real estate, but you’re going to have to get out there. Because the thing that I didn’t do initially, which I wish I had done, which hearing your story, you talk about meeting with attorneys, calling people, they’re saying, you look so young, is I was trying to learn everything, the logistics, the X’s and N’s, and try to be the most knowledgeable.

But then my business didn’t scale at all until I started just fanatically networking, just like every opportunity that I could get talking to someone within the real estate space, going to meetups, even when…

I might have felt like, do I have to provide? Before I was a licensed agent, before I had done a bunch of wholesale deals. But it totally changes you when you’re on the other side of it, and you’re like, no, I wanna help, and you probably feel the same way, Byron, I wanna help young people, hungry people get into the real estate space.

Byron Pillow aka The Smooth Realtor (03:53.214)
Mm-hmm.

most definitely, It’s a way to change the outcome for your family in the future, build this generational wealth, all different kinds of things and processes that I honestly hate to say this, that I wasn’t really taught growing up, that actually I had to learn on my own. And I definitely am very charitable by sharing this information with others and letting people know, know, it’s not really what you know, it’s more so about who you know. Like that really, I mean, that’s an old saying, but it’s so much true.

Dylan Silver (04:03.624)
Yeah.

Dylan Silver (04:22.833)
It is. It’s true.

Byron Pillow aka The Smooth Realtor (04:25.671)
It carries so much weight from now, even from when I first heard it, probably in the 90s, I don’t know. It’s still the same thing. just hope that, well, when I do talk with people, hope they listen, because that’s another thing. We fully don’t listen sometimes. It goes in one ear and out the other. That’s another one of those phrases. And people sometimes don’t trust you from what you do. You can tell them what it is, but you got to build that thing. Luckily for me,

Dylan Silver (04:32.307)
Yeah.

Dylan Silver (04:46.985)
It is.

Byron Pillow aka The Smooth Realtor (04:55.997)
I have always been scared of laws. So, you know, that’s the reason why I went to talk to attorneys first and so to make sure whatever I was doing was legal, that I wouldn’t have any repercussions to me from doing what I was doing. When I found that all out, I just took off.

Dylan Silver (05:04.019)
Me too.

Dylan Silver (05:11.583)
You know, one of the interesting things about real estate in general is you have people who come from generational real estate. Their grandparents were…

real estate brokers, know, or their grandparents, great grandparents were builders and contractors. And so then they became involved in the trades and the service providers to the real estate space are just as integral as, everybody else. Right. You don’t have the home without the builders. But then you have other people like me who had no body in the real estate space where I when I would even go tell people that I wanted to go do real estate, they would just laugh and they would be like, OK, you know, you know, yeah, OK, yeah, the whole cash for keys, whatever. Sure. Good luck with that. And so

Byron Pillow aka The Smooth Realtor (05:46.481)
I’m sorry.

Dylan Silver (05:53.751)
You mentioned that you, was it a Google search that got you into, you know, how to make money in real estate?

Byron Pillow aka The Smooth Realtor (05:59.934)
Yeah, I went in, I was searching just different ways of making money in real estate after I found out about the market crash. And then I start to look at public information like auctions at the courthouse and I was looking at people buying houses for two to $25,000. And then when I go look at the house that they paid $20,000 for, and this is a house that’s technically worth, you know.

$300,000 in 2007 2008, you know, and I was like wow They were getting good deals on in this because of so many foreclosures at this present time if you had cash readily available to purchase them, know, and then I like I said I looked into how I can wholesale those deals I looked at you know a little bit later on into it I looked into finding like private money lenders hard money lenders and stuff like this so I can do fix and flips I did my first fix and flip in

Even though I was on real estate for a while, did my first fix and flip in 2015 and I actually found a private money lender who I didn’t have to pay anything monthly. Like they literally got paid once I sold the property. You know, of course it cuts down on your profits, but I mean, I literally put no money down. All I did was sit, have a conversation, presented the numbers, which I’m very good at. Like that’s my niche is the whole numbers thing. I tell everybody it’s cause I’m smooth and stuff like that. Cause I dress nice.

Dylan Silver (07:09.129)
Turn.

Byron Pillow aka The Smooth Realtor (07:23.101)
But it’s really, it’s like I’m very good with those numbers. I’m precise with it as far as ARVs and such like that. And, you know, I presented him, he funded it, everything, you know.

Dylan Silver (07:33.073)
Accounting background probably helps there.

Byron Pillow aka The Smooth Realtor (07:35.786)
Just a tad bit, just a tad bit. Yeah.

Dylan Silver (07:37.651)
Just a tad. You know, when I think about the path that you went on, it’s different from my own, but my path was I was tired of working a W-2 job and knew that the threat that other people perceived from commission only, know, real estate, you know, there’s uncertainty. I actually felt that level of threat working a W-2 job.

because I felt like I’m missing out on so much of my life, like I’m living here, you know? And also, there’s people that are 20, 30 years my senior, and I didn’t exactly like how it was looking out, like am I gonna end up feeling and looking the way that they do? I hate to be so blunt about it, but I just said, there’s gotta be a better way. And so, I got licensed in Dallas, and you were in college when you got

Byron Pillow aka The Smooth Realtor (08:03.335)
Mm-hmm

Dylan Silver (08:30.941)
when you got licensed. Walk me through that process of getting the real estate license, of going to take the test, and while also being a college student.

Byron Pillow aka The Smooth Realtor (08:43.113)
So it was actually very easy for me. I’m very studious Literally, I did an online class 250 bucks, you know, go at your own pace Once I was I mean my senior year. I literally had on like four classes that I had to take So I have a lot of time so I didn’t want to have just idle time being wasted Literally 35 days. It took me to actually pass the course

I took the test probably like a week later, passed it on the first time. And in Alabama, that’s great because Alabama has averaged about four times before that somebody actually passes it. I, at this present time, like I said, I was a broke college student, know, $75 back then to me to take a test was a lot of money. So I was like, I’m not wasting that opportunity, especially after spending $250 on the course. Went in there, knocked it out, passed, and I’ve really got my license.

and I didn’t actually have it active for a while, but I had it obtained. Yeah, because once I got that license and they told me, yeah, you gotta join the MLS and you gotta join the brokerage and then, yeah, so then everything was like, I need $2,500 just to be a realtor. I was like, oh man.

Dylan Silver (09:45.279)
because it costs so much money.

Dylan Silver (09:52.479)
another thousand dollars a year. I’m like, oh my gosh.

Dylan Silver (09:59.775)
It’s exactly right. was going to say it’s like three grand to be a realtor. It might have been a little bit less back then, but still.

Byron Pillow aka The Smooth Realtor (10:04.584)
I said, well, I was like, how much is it to be an inactive realtor? They was like, uh, $200. I was like, so once I give me somebody, get it. I get myself going. And like I said, literally, uh, well, it was a year and a half late because I graduated December 2012 and I started January of 2014. I had the money then and I went active. I started with a mom in prop brokerage out of Birmingham that a friend of mine.

Dylan Silver (10:09.759)
Yes.

That’ll be me.

Byron Pillow aka The Smooth Realtor (10:32.888)
family owned in Birmingham and you know his family they had embraced me anyway and you know they took me in they provided a lot of lessons for me and stuff as far as networking and also learning southern business because there’s a difference in way business is conducted up north as they say here and then it is down south you know there’s still this element of being you know relatable and

Dylan Silver (10:53.983)
I don’t know.

Byron Pillow aka The Smooth Realtor (10:58.381)
and outgoing, fun, and like a family-orientated thing that transients on both sides, but it’s more heavily down here. In the South, if I sell you a house, usually they gonna invite you over for dinner, some sort of holiday cookout consistently. Whereas when I work back home in Chicago, it’s just about the numbers. If your numbers is perfect, they think you do good business. It’s not about telling somebody, happy Hanukkah.

Dylan Silver (11:07.647)
That’s her.

Byron Pillow aka The Smooth Realtor (11:26.767)
Rosh Hashanah, know, know nothing like that. Happy Kwanzaa, know, know, E Mubarak, none of that, you know, they don’t care about that. They numbers, numbers are tight. We’re good. Vibra’s a great guy here. You gotta know everything. Yeah, you gotta know A day.

Dylan Silver (11:34.291)
Yeah, it’s a different, it’s a different, different ballgame.

out again at a school where where you focused on trying to make real estate full time what was it like to get a job immediately get out of school was a transition like as a you know recent graduate

Byron Pillow aka The Smooth Realtor (11:51.911)
So when I got out of college, I did little odd jobs, but like not traditional jobs. like first thing I did was I started selling gym shoes, sneakers. That was my first thing. I I sold probably.

for a year, maybe about a thousand pairs of shoes. I just was selling them consistently. I actually was also a party promoter as well. So I, you know, I used the little bit of, you know, notoriety I had from college still left over for a few years to throw parties. And then as that was going, I was also building, you know, my network. You know, I was meeting people and I was explaining to them, I was getting in real estate and I literally every day for almost two years.

I wore a bow tie every day and I would go to lawyers offices, title companies, other real estate brokerages. I would meet with HVAC guys, contractors, builders, anybody that was around the sphere of real estate somehow. I would just go and meet them and I would tell them my name is Byron. You know, I’m interested in getting real estate. I just want to meet you for future purposes. I never know when I might need whatever it is. HVAC, Pest Guide, you know.

Dylan Silver (13:08.404)
Man.

Byron Pillow aka The Smooth Realtor (13:08.871)
a bus driver, you I was just going to meet these people. know, like I said, I learned those skills in Chicago to just meet everybody, you know. My uncle always said, if you go in a room with a thousand people, all thousand people should know you by the time it’s done. So, you know, I’ve always been like, I have never had an issue with going in a room with people I don’t know, you know, and just, hey, I’m bi-er. You know, my uncle told me this other thing. He always said, ask the person, how much does an elephant weigh? You know, and people would be like, you know, what?

enough to break the ice how I’m by right now. You see like real talk it always brings a smile out of person’s face you get to talking to them and then you explain to them what you’re trying to do what you’re interested in and then you you provide whatever is necessary for that person and then like I said I jumped full fledged in in 2014 I had enough money saved where I could pay my rent for some months which I wouldn’t have had and did you know I had I owned my car so I had to worry about paying the car note

Dylan Silver (13:38.599)
Enough of you guys.

Byron Pillow aka The Smooth Realtor (14:05.7)
I just took off and I did whatever it was ever. My first sale was actually four hours and 25 minutes away from where I lived. I would travel all up and down Alabama. I’ve been to places in Alabama that people who are originally from Alabama have never heard of. And then I wanted to expand to Georgia because there’s so many people I went to college with that they moved to Atlanta and surrounding areas. I just went there, got Georgia’s license, saw how easy it was, started doing the same thing I did in Alabama, repeating.

Dylan Silver (14:26.26)
Yeah.

Byron Pillow aka The Smooth Realtor (14:35.462)
You know, meeting everybody, lawyers, attorneys, garbage men, whatever it was. I just kept repeating that and that was a part of my system was to meet everybody to the point where everybody remembered me. And because I have a very interesting last name with it being a device you lay your head on at night, people always remember me. So it was like, you yeah, that’s the pillow guy. Yeah, I remember him real good. You know, and I start making different, you know, slangs and such like that. tell people, you know, my name’s Byron Pillow, but don’t sleep on me. You know.

Dylan Silver (14:54.975)
I

Byron Pillow aka The Smooth Realtor (15:04.994)
You can sleep comfortable if you lay your head on a Byron pillow as your realtor. Stuff like that. know, just little different things that help people remember. And then they just like, yeah, he’s got a bubbly personality. He really loves Chicago. He always talks about it. know, so those things help me out a lot.

Dylan Silver (15:19.615)
When did investing come into play and when did you start working heavily with investors?

Byron Pillow aka The Smooth Realtor (15:25.68)
So that’s how I actually started my career, was working with them. I looked at the numbers. looked at people traditionally buying, like I want my forever home, or my starter home, or whatever the case was, was a lower number in comparison to that of investors. It was like literally eight to one. An investor would buy eight houses, and you would buy one traditional buy, they just buy one house.

I looked at the fact that I can just do it in volume and then I would connect these people and then, like I say, I have a good CRM. just I have an issue with sometimes with reaching back out to people about certain stuff like that, which I’m gonna work on. It’s definitely always something you continuously work on with building yourself and your brand within real estate. I just start talking to these people and finding what they want.

You know, hey, I want something well, you know, I need a three-barrel, one and a half bathroom at Section 8 to pay me $15.87 for it. Give me a second, I’ll find it for you. I’ll find it by Tuesday. It’s under contract Thursday, so next Wednesday.

Dylan Silver (16:30.559)
Thank you.

Dylan Silver (16:35.423)
So let’s pivot a bit here and talk about when you started getting into fix and flipping on your own and some of the rentals that you’ve got on your own. When you were getting into real estate, it was with the intention of owning the real estate or being involved in it yourself.

it’s probably similar to me in some way. look at all the work that I’m doing with investors as well. How do I become the investor? So walk us through that first deal where the first fix and flip on your own or the first rental property that you had.

Byron Pillow aka The Smooth Realtor (17:01.796)
you

Byron Pillow aka The Smooth Realtor (17:07.236)
So my first fix and flip, it was actually in Birmingham. It was on the east side of Birmingham. And it was a property that was a three bedroom, one and a half bathroom. It was 1,300 square feet, a little bit, well it was a little bit over there, like 1,350 something. But I looked at the neighborhood, the comps, I also looked at people who buy in with that Section 8 path program, know, the way you go from Section 8 to actually a homeowner. And I just looked at…

those type of things and then the connection that I made before they were actually a private money lender. They allowed me to, you know, borrow funds to actually acquire the property and to fix the property up. I didn’t have to pay anything back until we closed on a property, which was great because I didn’t have to, you know, most of the time with hard money lenders and private money lenders, they want like an interest only payment monthly until, you you sell. I didn’t have to pay anything out of property. I just got the work done.

and everything was done quickly. made everything go up to FHA regulations. That’s what the contractors I connected with, they knew how to do those things. And then it took me almost two months to get the property ready. I listed it and I had it under contract in 22 days.

Dylan Silver (18:23.103)
Wow, wow, that’s quite the W for your first fix and flip. I wanna ask you, because we are coming up on time here, for folks who are thinking about getting into real estate, would you recommend that they get a real estate license, I got my real estate license, or would you say in some ways it can impede you if you’re looking at doing some of these more creative things like wholesale?

Byron Pillow aka The Smooth Realtor (18:28.899)
Hmm.

Dylan Silver (18:49.279)
subject to deals and so on and so forth.

Byron Pillow aka The Smooth Realtor (18:53.812)
So yes, I would actually, and I tell people this now, if I learned all the different tactics as far as real estate investing first, except for just learning whole selling, I probably wouldn’t have my real estate license, to be honest with you. I would probably just put a heavy focus in that. If you got good credit, that’s pretty much all you really need. You can get with a realtor and they can send you everything that you want. Trust me, us realtor, we are happy to…

You know, send whatever we can to anybody to make whatever form of commission that we can make. Trust me, I’m pretty sure I’ve made all my investors millions of dollars. Well, I made myself hundreds of thousands of dollars, you know. So I’m pretty sure that, you know, if you were to connect with the right people, because that’s my main thing is you have to network correctly. You know, you have to meet everybody. That’s the one thing you do that. You really won’t need no license. know, don’t be scared to see a person because you.

Dylan Silver (19:36.68)
Right.

Dylan Silver (19:50.087)
Yeah, I agree.

Byron Pillow aka The Smooth Realtor (19:52.598)
You know, there’s a lot of people that are introverts, but you gotta come about that share. If you don’t come about that share, you’ll never meet the people that you need to meet to achieve the things you need to achieve.

Dylan Silver (20:05.565)
Byron, know, would consider myself an introvert and it was just so hard. I remember, I’m not going to say the guy’s name, there was a social media personality, big investor at an auction in San Antonio, Texas, where I was living at the time. And I saw him at the auction and I just didn’t go up and say hi. And I knew who he was. I don’t think he knew who I was, but I knew who he was. And I was just like petrified there. And I was like, that was terrible. I can’t believe I just kind of flaked out and saying hello to somebody.

Since I came up to Dallas, I made it just an absolute focus, like, hey, I’m gonna figure out how to get good at networking. And I was like, well, how do I do it? How do I do it? How do I do it? And it really is a muscle. Like, that’s honestly something that I can say. If you’re introverted and you’re not great at going out and you feel like you have a low social battery, it’s literally like going to the gym. Like, the more you go to the gym,

the better you are at lifting weights. The more you focus on not just being social, because it’s being social with new people, like making connections with strangers type of thing. That is a difficult skill, I think, for me and some other people. But now with the podcast and then just going to events all the time, now it’s like old hat. Now to your point, now it’s like, hey, what’s your name? What do you do? How can I make you money? Like, let’s network together. You know what I mean?

Byron Pillow aka The Smooth Realtor (21:22.85)
Well, I will say this much I learned a lot of stuff just in life from my uncle and from music and one of my favorite artists is Jay-Z and And one of his songs he has said amazed scholars the way we coin phrases for dollars so I took that and of course put my own twist on it to learn about it and I’ve always had that as a thing of mine that I was like, okay, I’m going to

make sure that everybody that I meet understands what I want to do and what my goals are in life. And I want to amaze them by what I’m saying and what I’m actually going to do. And if you do those things and have those certain tactics and beliefs in yourself, you will find success. Like you said, it is very hard to get up out of that shell, but if you’re able to break it, you will find all the success you need.

Dylan Silver (22:16.767)
Byron, we are coming up on time here. Where can folks go if they’d like to learn more about your business or reach out to you, get in touch with you?

Byron Pillow aka The Smooth Realtor (22:25.374)
I’m very big on Instagram. My Instagram is Onesmoothrealtor and that’s the number one and then S-M-O-O-T-H-R-E-A-L-T-O-R Realtor and that’s pretty much for all the social medias. It’s the same name. My LinkedIn is ByronPillow, of course. My Facebook is ByronPillow Realtor with EXPRealti and yeah, reach out to me and plus my number’s public. If you just want to talk to me,

I’m one of those type of people, I’m happy to talk to you about anything. It doesn’t matter if it’s real estate, sports, music, cars, food, real Chicago pizza, not the deep dish stuff, because we don’t eat that, that’s like more so like celebration tourist pizza, whatever, we can talk about whatever you need.

Dylan Silver (23:12.645)
and thank you so much for coming on the show here today.

Byron Pillow aka The Smooth Realtor (23:16.294)
You’re welcome man, like I said it a pleasure man. I want you to prosper within your podcast of course man and definitely, definitely keep continuously doing this.