From Stripper to Success: 5 Key Lessons in Real Estate Investing

Dylan Silver (00:01.058)
Hey folks, welcome back to the show. Today on the show, we have a real estate investor, entrepreneur, financial educator, founder of the Millionaire’s Lounge and creator of Legacy Bundle out of Richmond, Virginia, Stephanie Nicole Stephanie. Welcome to the show.Stephanie Nicole (00:20.98)
Thank you for having me.

Dylan Silver (00:23.222)
It’s a pleasure to have you. I always like to start off at the top, Stephanie, by asking folks how they got into the real estate space.

Stephanie Nicole (00:32.208)
Well, I got into the real estate space. It is a crazy, crazy story. And before I start, I don’t want people to judge me. This is just my story. I’m putting it out there and it should.

inspire people to take the next step because I’m a regular person. So right before I was in real estate, while I am somebody who’s college educated, I was in the military, I found myself working at the strip club just to make ends meet. So I had a regular job, but at night,

just to live the lifestyle that it was a regular lifestyle. So I don’t want to act like I had like this big lifestyle, but I used to work in a strip club. So one night I’m just dancing. It was a dry night. There wasn’t a lot of money in the club. And so I will say, you know, transparently I did have a small attitude, but as I’m on a stage, you know, I’m dancing, getting into the groove. There’s this guy that comes and he’s, you know, putting one dollar bills, like one

$1 every five minutes and then eventually and it’s gonna get a little vulgar But he’s like, I have a $20 bill if you pull your panties to the side I’ll give you this 20 so I get an attitude walk out the club put my clothes on go to my car and I actually start crying because I Started praying to God like why is it that me? What is it about me that you don’t love or don’t value that I have to spend my time taking

my clothes off for $1 bills just to be able to make the light bill, just to be able to have gas in my car. I have to degrade myself every single day and just being transparent again, like I was going through a season of depression right before that. And I did try to, you know, commit suicide and I didn’t die. So it’s like, you want me here.

Dylan Silver (02:12.291)
Yeah.

Stephanie Nicole (02:33.616)
So why is it that you want me here to suffer? So I prayed. was like, if I’m your child, if you love me, if I’m valued, if I have a purpose, please tell me what my purpose is because I can’t keep doing this. So something like at that moment told me just to Google, get on Google and Google how to become a millionaire. And real estate came up. So I’m like, I don’t know anything about real estate at this point. And at this point, I’m in my 20s.

I came from a background where people are on Section 8. We rent for our whole lives. I didn’t know about home ownership. So when I just saw real estate, I thought just to get my real estate license, was a blank slate, didn’t know anything about anything, and just got my license and came in.

Dylan Silver (03:25.07)
That was the entry point. I want to highlight something that you said, which was college education, military, still wasn’t enough money. And I think a lot of young people can relate to this. A lot of young people. I’m 31 years old and I know so many people who are my age, older and younger, kind of in that millennial, Gen Z and then the next generation.

age bracket and growing up on the East Coast, I grew up in a town in northern New Jersey, 27 miles from Manhattan, very Italian American town. I figured, you know, I’ll be able to live here one day. Well, now I don’t know what the average home price is in that area, but you basically need two incomes at like $110,000 a year, plus decent credit in order to qualify for a home where you’re going to be still, you know,

Stephanie Nicole (04:15.88)
Absolutely.

Dylan Silver (04:18.562)
with student debt, with potentially starting a family, it’s very, very, very, very, very difficult. And so, you know, I’m out here in Dallas, Texas, and one of the reasons why I’ve stayed in Texas, I’m new to Dallas, but I’ve been in Texas since about 2019, 2020 timeframe, one of the reasons that I’ve stayed out here is just because I know how difficult it is to survive where I grew up. I mean, it’s very, very difficult. So, similar,

to you, Stephanie, when I was working for Nissan and when I was thinking that I had made it in effect, I remember I had a nice car, had this apartment, two gyms and two pools in San Antonio, Texas, you know, mentioned in military, that’s a military town, right? And every year they would raise the rent and I would see that my income wasn’t going up that much. And I would see people who were 15, 20, 25 years older than me

Stephanie Nicole (04:55.358)
Yeah.

Dylan Silver (05:17.378)
doing the same job or maybe one level up from me with not a whole lot of savings. And I was like, man, I don’t know. I don’t know if this is going to be what I start doing forever. So similar to you, I googled something along the lines of, you know, other ways to make money as an entrepreneur. I don’t even remember what I searched for. It could have been how to be a millionaire. And I got to think more about that. But I discovered real estate. And fast forward two years later, it’s now

2025, we’re talking in June timeframe, I got my real estate license two months ago, but I’ve been wholesaling for the last couple of months. And so, know, Google has probably, and now chat GPT, but Google has probably changed both of our lives in pretty substantial ways.

Stephanie Nicole (05:53.633)
Wow!

Stephanie Nicole (05:59.712)
Yeah.

Stephanie Nicole (06:03.772)
Yes, and I love Chagy BT. That’s my best friend now.

Dylan Silver (06:08.014)
I can’t tell you how many things that I’ve learned from chat GBT, not just about real estate, but about software engineering, about other languages. But I want to pivot Stephanie and talk about what were those first steps like because you mentioned the real estate license. It took me a while to get to the real estate license for me because I honestly didn’t want to go that route. I went into wholesale, but you immediately dove in and went with the real estate license. So

How did you get the real estate license? Was it a lot of in-person classes? I know my test in Texas was pretty difficult. What was that process like for you?

Stephanie Nicole (06:47.776)
I ended up getting a real estate license because I didn’t know anything about real estate. So when I saw that 90 % of millionaires were in real estate, I was like, well, what do I do now? And Google said, you get your real estate license. So then I looked up, how do you get your real estate license? And it’s all these classes that popped up. So I didn’t even take an in-person class. I went online. I didn’t have any books. I don’t.

I will say that I am naturally smart. do, I did very well in school. I was like one of the top students. Like I had a perfect, I had perfect SOL scores. So I will say I’m naturally smarter. Well, smarter than, I don’t want to say smarter than people, but I’m a naturally smart person. So I didn’t, I will say I didn’t do a lot of studying. So I do think that if,

there was somebody that was watching right now that wanted to go get a real estate license. I would say it is an easy process. You can literally take the class online. The only thing that surprised me because I’m learning all this stuff on Google is the fees. Y’all, gotta have thousands of dollars. Yeah, they gave me a $3.50 bill. I was like, hold on. To get the license, like, just the license.

Dylan Silver (07:58.147)
Sure.

Lot of fees. Thousands.

one in the world. Let’s talk about the piece. This was in Virginia. Were you in Virginia at the time?

Stephanie Nicole (08:13.364)
Yes, so the actual class to get your real estate license is probably a hundred dollars But once you at you go to the state and get your license the state wants money MLS wants money the real estate association wants money your broker wants money So it ends up being thousands of dollars But I went back to the strip club got that money It came back in

Dylan Silver (08:24.632)
And now.

Dylan Silver (08:31.178)
It’s that I had the same thing.

Dylan Silver (08:37.25)
That’s one of the benefits of being in a cash heavy business. guess, you know, there’s there’s some level of rose colored glasses there. So when you’re going and you’re becoming a real estate agent, you know, I had this experience and maybe you can relate to this. It’s not like every real estate agent is talking about being a real estate investor or even working with investors. And honestly, it’s I would say it’s more on the uncommon side than it is on the common side and talking with real estate agents about

what I’ve done in wholesale and working with investors, oftentimes they’re like, yeah, I don’t wanna work with investors. They’re always making low offers. They’re hard to work with. And it’s a lot of that. So how did you get into the investment side when you started out as a real estate agent?

Stephanie Nicole (09:22.536)
Well, I was delusional. So when I first got into real estate, I thought I would just automatically be successful. then I had never really outside of the strip club. Every job that I had was a W-2 job. So I didn’t even understand entrepreneurship. So my first year in real estate was really hard. I sold one house to my mom.

I still was struggling and I kinda just got to the point where I was going around begging everybody for help. Like I would pull up the top producing agents on MLS, take them out to lunch. Anybody who had a name in real estate in my local area, I would try to connect with them. I’ll go to their meetups. eventually I came across somebody who saw…

like how I was putting myself out there constantly and he’s like, you know, I want to give you an opportunity. I’m looking for somebody to help me, you know, just make phone calls on acquisitions. And he was a real estate investor. He’s still my mentor to this day. He had, he runs a short term rental business, but in order to get those properties, he is quote, he’s something similar to a wholesaler. wouldn’t consider him a wholesaler, but he comes across investor leads. So my job at that time,

Dylan Silver (10:42.626)
Yeah.

Stephanie Nicole (10:43.138)
was just to call all of these people who may want to sell their house and that and watching him, you know, purchase, you know, go through the leads, purchase houses that deals anything that wasn’t a deal. He would have me listed a property on the market as a real estate agent. And then I see him close on these deals. And then he was doing short term rentals. So now I’m like, you’re making like five, $6,000 a month. I want to do that, too.

And I asked him for his help and he helped me so that’s how I got into investing.

Dylan Silver (11:15.808)
So I want to get a good picture of the timeline here and get a little granular here, Stephanie. So from the time that you started real estate, meaning you started thinking about I got to get my license to the time you met this mentor. How long was that? Was it a year? Was it a year and a half? How long was that that time period? So it was it was a struggle. It was it was a struggle.

Stephanie Nicole (11:32.576)
two years. I may have been moving into my second year. Yeah, like my first year was my first year. I got to the point where I was so desperate that I was going on indeed looking for people who are looking for people with real estate license. And I almost took a job with Redfin for $30,000 a year.

Dylan Silver (11:58.414)
And so I think a lot of real estate agents can relate to this. don’t think by any stretch of the imagination, you’re the only one. think, I hate to say this, but I think most new real estate agents will go through this. What was it that kept you, Stephanie, I mean, you talk a two year period that kept you saying, I’m going to make this work. Why were you so determined to make real estate work?

Stephanie Nicole (12:21.332)
I didn’t have a backup plan. had tried everything else. went to the military, which I have nothing bad to say about the military. think that everybody coming out of high school or college should go to the military because it gives you a different type of discipline. But it also is a real thing. I went to Afghanistan. I was in combat twice. I could have died. So that’s the reason I got out of the military because it was just, I didn’t think that it was worth risking my life. But just moving back to

subject is I’m sorry what was the question I’m sorry

Dylan Silver (12:55.512)
I just, it’s a lot of, you mentioned, I do want to point that out though, which is that there’s so many benefits to military on the flip side. I don’t know, did you go in knowing you would be deployed? Did you know that you would be deployed to Afghanistan? You did not know.

Stephanie Nicole (13:09.226)
They got me at 17 years old. I was living on the street. I had moved out of my mom’s house. A lot of this is just because I don’t have a backup plan. I went to the military because I was already on the streets. I didn’t have a place to stay, so I signed up just to have a place to stay and to get off the streets. And then once I had a ball in the military, I loved it until I got deployed and it was just…

Dylan Silver (13:22.275)
Ciao.

Dylan Silver (13:27.458)
Yeah.

Stephanie Nicole (13:37.513)
It was bombs out there. Y’all don’t understand. I was on a convoy that got hit and I saw somebody burn.

Dylan Silver (13:38.188)
Now it’s like… Yeah.

Stephanie Nicole (13:46.645)
He’s alive to this day, but just watching him burn is still is in my soul. So that’s why I got out. And then from there, it’s like, was like, how do you even get ahead? Because I did everything that people told me to do. I have a college degree. I’m trying to find my way in this world and find an avenue where I don’t have to work every single moment of my waking life just to

Dylan Silver (14:02.946)
do.

Stephanie Nicole (14:15.838)
get by and I at the time it was like I knew that if I didn’t make it in real estate I was going back to my old life where it was and I don’t want to make it seem like I wasn’t like I was struggling struggling I did have money enough money to pay my bills but it let’s just say my tire went out or you know my

Dylan Silver (14:38.424)
it’s an emergency.

Stephanie Nicole (14:39.548)
yeah any emergency that would throw me behind because I didn’t have enough money for emergencies and then yeah.

Dylan Silver (14:45.568)
I can relate to that. And I do want to interject with this thought. I think so many people can relate to that because you talk about, you know, military college degree, right? You’re trying to make it in real estate and you’re thinking, well, when I went through school, I did all the things that I was told to do. Military college right now. I’m out here trying to make it and it’s so hard.

And I’m like, I need two, three jobs to do this. And now I have no time to myself. So now when I finally get home at the end of the day, I have like zero energy. Have you ever had this feeling, Stephanie, where you like don’t even have enough energy to sleep? You’re like, you get home at the end of the day and you’re like, I’m so tired that like, I’m just gonna like collapse here. And then you wake up and you’re more tired because you didn’t sleep well. That’s happened to me before.

And I thought like there’s got to be a better way than this because I was seeing people again, coming from working in automotive dealership where they’re working 12 14 hour days, five days a week. And then we worked on Sundays as well. So mean, you’re talking people and I don’t want to paint this industry in negative light, but a lot of people who are just at their wits end, a lot of people who never really saw their family and it was just understood and expected.

So pivoting from that to then going into real estate, I had a similar experience, Stephanie. was like, I am going to make this work. I don’t care what happens because I already know what the worst case scenario is. The worst case scenario for me, which seemed like maybe not so bad for other people. But for me, it was like and I hate to over exaggerate here, but it was like some type of spiritual crisis is if I have to say in this W2 job where I’m working 12 to 14 hours a day.

Stephanie Nicole (16:17.31)
Yeah.

Stephanie Nicole (16:21.685)
Yeah.

Dylan Silver (16:37.336)
where I’m dead exhausted, where like I’m a shell of myself, where I don’t even have enough energy to properly like sleep. I don’t know what the rest of my life is gonna look like. I don’t even know if I’m gonna make it to 50, because I might like have a stroke or something. And so that was the kind of impending doom feeling. I know that sounds like a exaggeration, but that was the feeling that I had. So I was just absolutely.

Stephanie Nicole (16:52.277)
Yeah.

Dylan Silver (17:04.086)
Determined to make it and it really sounds like you had a similar Since feeling like I have to make this work

Stephanie Nicole (17:12.454)
Yes, I didn’t have a backup plan that was the plan. There was, it was nothing else I could do.

Dylan Silver (17:19.34)
And so you meet the mentor, you’re two years in, and then he gives you, is he giving you distressed seller leads? You mentioned he’s giving you some type of leads to call.

Stephanie Nicole (17:29.476)
necessarily say there were like lead leads it was him finding deals for himself and I was just the the the person who had the time because he you know he’s running a short-term rental business he’s running a real estate team he got a full-time job he got five kids his wife like it’s a lot so I

he was looking for somebody to come take some stuff off of his plate. And at the time, I was just so thankful that somebody was willing to kind of teach me, pour into me that I was whatever he needed me to do, I was going to do it. So it started off with just phone calls to people. And now fast forward now, where I don’t want to say like we’re we have a full team where we’re like business partners, where we, you know, we do everything

together and I personally don’t even make any type of real estate investing decisions without at least talking to them. it

Dylan Silver (18:31.436)
I want to ask you Stephanie about how the real estate agent license being a realtor paired with this because I know I’ll open some doors, I’ll list some homes. I haven’t done that yet because I’m so newly licensed but really my passion is in real estate investing and I feel like yes they go hand in hand but also you do have to pick one when you’re just starting out. So when you had this experience with this mentor and you’re seeing how he’s

able to really teach you the game. you did a light bulb go off in your head and do you say, okay, I’m going to get my own short term rentals or I’m going to go build my own portfolio.

Stephanie Nicole (19:09.856)
Not at first, no. And as it relates, I think that all real estate investors or anybody who is in the

in the real estate business and is doing it on a consistent regular basis should have their real estate license. It is just another tool in your tool belt. It does not stop you from anything and for every lead that you can’t close on or that is not a good fit for you or that is not necessarily a deal but you have somebody who wants help with selling their property, you’re still there to help that person.

Dylan Silver (19:40.12)
listed.

Stephanie Nicole (19:44.797)
It’s more about helping people out of the situations that they’re in. A lot of the people that we were talking to at the time, they have problems that they’re trying to solve. And we’re just there to help them solve those problems. And with having that real estate license, you are the go-to person. Whatever problem that person has, you can solve it. You have every tool in your tool belt to solve it. You don’t got to even send it to anybody else. So I’m really big on having your license as an investor.

Dylan Silver (20:11.65)
That’s % right. I feel the same way. If you don’t have the ability to have, you know, the good fortune of having some giant nest egg, you know, $100,000 to start getting hard money loans and making cash offers on properties. And if you don’t have some giant network, or maybe you don’t come from real estate, I know some people are like generational, my dad was in real estate, his dad, I didn’t have any of that. So when I went to start to go do real estate as a wholesaler, I would tell my friends and then they would just

be like laughing like this is the silliest thing that you could do you’re gonna buy homes with no money yeah and I’m gonna go to the moon like that would be their response like this is not real Dylan you can’t now I will say you know when I met these guys it wasn’t when I was in the real estate space it was a completely different circumstance we just liked being buddies and we some of them were from the car business but then when I started to network within real estate that’s when things really started to click

for me. That’s how I met my mentor. Not not exactly how you met yours, but I actually had a property under contract west of Dallas in a town called Aizle with a company that I was working for at the time that since went defunct but and I was just cold calling investors. I was cold calling investors and I said, Hey, I have this property. Are you interested in taking a look at it? The guy that I called was not interested in really

purchasing the property, he put in an initial offer and it didn’t end up getting accepted. But then I just kept staying in touch and over time we developed this relationship. And so I think this idea of fanatically networking and just constantly just like you were doing Stephanie, I have to meet this person, I have to make the connection, I don’t know where it’s going to come from, but I’m going to just kind of hit up every top producer until it works. That that’s a real thing. And that kind of, you know, sweat equity or time on the phones will will

change lives.

Stephanie Nicole (22:10.323)
Yes.

Dylan Silver (22:13.388)
I do want to ask you about pivoting to today and what the business looks like today. You mentioned that you had maybe not initially when you had started working with your mentor, seeing that real estate investing was the path that you were going to go down. At what point did you say, OK, I’m going to dive into this. then how did the business scale to where it is today?

Stephanie Nicole (22:36.136)
So I was so thankful for my mentor. I wanted to do everything in my power to just make it to where he knew that he made the best decision in his life. So I started just trying to make him so much money that I ended up making myself a lot of money. So then I have like $400,000 just saved in a bank. Mind you, I’ve never seen this type of money. I’m coming from paycheck to paycheck.

So now I just have 400,000 sitting in a bank because I just didn’t know what to do with it. So I came back to my mentor. like, I had.

Dylan Silver (23:05.976)
Yeah.

Stephanie Nicole (23:13.504)
I just have this money in my bank account. What do I do? He’s like, why would you even have all that money and you should have been investing the whole time? And he was he kind of coached me through he was like, what? What are your goals? What are you trying? Like what? Where do you see yourself at like 50? What do you see yourself at 60? Like, how are you trying to? What are you trying to do with your life? So once we got through that, he

Dylan Silver (23:36.867)
Yeah.

Stephanie Nicole (23:42.337)
he helped me start buying houses for long term rentals just to as sort of like a bank account rather than saving my money because if you save your money in a bank account by the time you get done with receiving the bank’s interest in an inflation being on top you’ve just lost money so that $400,000 would not buy the same thing then that it does now like right now with $400,000 I wouldn’t have been able to do the same things so

Dylan Silver (23:51.448)
Sure.

Dylan Silver (24:01.944)
You’ve lost mine.

Dylan Silver (24:07.822)
you know.

100%.

Stephanie Nicole (24:11.784)
ended up buying, it was either three or four properties right off top that we all found together. So my mentor helped me start a long-term rental business. And since then, because I had, I had a bad tenant, it was my fault. Cause one, I bought the house with the tenant in there and I should have just kept them. I should have kicked them out or evicted them. I was trying to be too nice and then I ended up losing money and they ended up crashing my house. So I ended up putting it as a short-term rental.

Dylan Silver (24:35.694)
Yeah.

Stephanie Nicole (24:41.33)
And then the house that I moved into that I live in, had a space that I created as like an in-law suite. And then I’m like, hmm, let me put this on Airbnb too. And then my spaces that were on Airbnb was making just so much more money than my other rentals that I’m just like, I think I should get into the short-term rental business. So that’s how we got to today.

Dylan Silver (25:04.022)
And so did you then do multiple short term rentals? you position everything as a short term rental? Did you keep some of them as long term rentals?

Stephanie Nicole (25:15.424)
So as people are like my first, I ended up evicting, well, my first Airbnb is a house that I live in. So that made me kind of like look at the pricing, like, hold on, I think I’m making three times as much in a space inside my house than I am on entire houses that I’ve bought. So then when I had the tenant that wasn’t doing the right thing,

I didn’t even actually evict him. just asked him to, I paid them to leave. And then I was like, I didn’t want to get back into that. So I ended up putting that one on short term rental and it was great. So, and then I actually sold a house before that had a bad tenant. And in the back of my head, I wish I had kept it, but this is before I really knew about Airbnb and short term rentals. So I ended up selling that house, but as people move out, I’m converting them to short term.

Dylan Silver (26:13.366)
I do want to get your thoughts on having a short-term rental business. Were you using all Airbnb? Was that the strategy that you were using the platform?

Stephanie Nicole (26:23.582)
I have my own, I’m doing my own thing because I like to remain as hands-off as possible. So I use a property management company to get my bookings and then they send my bookings to my cleaners who then go to clean it. I don’t know where they’re posting to. I’m just assuming it’s Airbnb but I’m pretty sure they’re posting across multiple platforms. just, have, you know.

Dylan Silver (26:39.394)
They’re doing everything.

Stephanie Nicole (26:50.74)
giving that to somebody else so I can focus on more.

Dylan Silver (26:52.812)
That’s a that’s a good thing. That’s a good flex, Stephanie, because honestly, most people will say they don’t want to have to deal with the property managers because if they feel like it eats away too much of their margin. But if you found a situation like the one that you have with property manager is great. It’s hands off for you. It’s passive income. And you’re able to cash flow from it like that’s a win win win the property manager is happy. You’re happy. The Airbnb guests are happy and

Stephanie Nicole (26:56.701)
I’m sorry.

Dylan Silver (27:21.228)
you know, it’s passive income. So, congrats on that. I do want to ask you, before we wrap here, we are coming up on time, if you had to talk to yourself when you were looking at getting into the real estate space, or anyone who might potentially be looking at getting into the real estate space, and give them some advice on what steps to take and how to start, what feedback would you give that person or yourself when you were starting?

Stephanie Nicole (27:51.228)
say if you’re thinking about it just come on try it out get your real estate license. I just think it’s easier to come in as a licensed realtor and you have so much access to different people who can teach you the business that’s just my my advice come in with a real estate license get with a good broker get with some good people get some mentorship.

and you will be successful and do the work. Because I feel like there’s a lot of people who come into real estate just because it was something cool that they’ve seen on Instagram or they’ve seen another realtor that they was really pretty and she was dressed nice. So now they want the image more than they want the success. If you want the image, those images are not real.

Dylan Silver (28:25.859)
Yeah.

Stephanie Nicole (28:39.068)
Now if you want this success, anybody can be successful in real estate. If I can do it, anybody else can do it. Because I’m going let you all know I was 20 something years old. I didn’t even know people owned houses. So if I can go from that to this in that amount of time, anybody can do anything.

Dylan Silver (28:55.916)
Stephanie, thank you so much for coming on the show here today. If folks wanted to reach out to you, or if they’d like to learn more about your business, how can they get a hold of you?

Stephanie Nicole (29:06.688)
All of my social medias. I’m on Instagram, TikTok, and Facebook and everything is Stephanie Nicole RVA.

Dylan Silver (29:16.686)
Stephanie, thank you for coming on the show here today. Congrats on all your success and to your continued success.

Stephanie Nicole (29:24.491)
Thank you and thank you for having me. was a great chat.