Real Estate Investing Success Story: Escaping the 9–5 Grind

Chelsea Westover (00:00)
I don’t like using the term TC because we don’t coordinate, we manage. That’s how we specifically run transactions is I want to be able to manage everything from whenever you bring me onto the deal up until closing. And then we can get involved after closing, depending on the type of transaction, especially with, uh, creative financing. So I don’t know how familiar you are with that. We don’t actually work with lenders that often.

I’m going to be brutally honest, we primarily work in the creative space where there’s not lenders involved most of the time. So it becomes that much more tricky because of the types of deals that we are closing. And so the level of expertise, it’s not, hey, give everything to a lender, just give the lender what they need and then close. These are subject to transactions, right? These are seller financing where you really need to make sure that you’re setting yourself up for success and not just the buyer, but also the seller. Because if the buyer is not set up for success,

Dylan Silver (00:30)
Yeah.

Hey folks, welcome back to the show. Today’s guest is based in West Virginia and is a consultant for real estate investors through the TC Collective. Please welcome Chelsea Westover. Chelsea, welcome to the show.

Chelsea Westover (02:34)
Thanks so much for having me, Dylan. I’m excited to be on.

Dylan Silver (02:37)
It’s great to have you. I always like to start off at the top, Chelsea, by asking folks how they got into real estate.

Chelsea Westover (02:44)
It is not a very good story when I say that. ⁓ I was working for the government and I was driving to work one day and I just kept thinking to myself, this can’t be it. I can’t continue to go to work nine to five, the same route, wearing the same type of clothing all the above. And so I started to just Google and figure out how do I get out of this grind? And…

One of my coworkers actually was investing in real estate. And so ironically, I asked him, you know, hey, how did you get into this? It seems like it’s a really good opportunity to be able to make some more money. And he said, I just read a book. Have you tried it? So that pretty much just like set me off when I was like, well, that’s, you know, that’s very intuitive of you to say to me. So I just grabbed a book and it ended up being one of Brandon Turner’s books and just kind of went from there. And that was back in 2021.

and been involved ever since.

Dylan Silver (03:42)
So did you dive in? you do it simultaneously with the government job that you had? Was it a slower process? you saying, hey, is my new passion, new career? Was it more of a progressive?

Chelsea Westover (03:55)
It was progressive. am not, I was not as much of a risk taker as I am now. I’ll say I’ve kind of slowly became that as I’ve met more amazing people who are very much risk takers. So it started off as a side hustle. I actually started out in a BRRR mentoring program. This was in the middle of COVID, started doing that. And through that met a business partner, she and I hooked up and we purchased our first duplex through a wholesaler, had no idea what we were doing, learned so much. Now looking back,

Dylan Silver (04:07)
Yeah.

Chelsea Westover (04:25)
we made so many freaking mistakes, but that’s okay. It ended up cash flowing. It’s all good. We learned a lot through that first one. And it really taught me for my second, third, fourth, you know, as I continued to grow and want to pursue other things, it just taught me, doesn’t matter, you’re make a ton of mistakes, but just keep putting one foot in front of the other and you’ll, yeah, you’ll figure it out. And then from there, worked for a wholesaler, got into creative financing and…

Dylan Silver (04:43)
Keep going.

Chelsea Westover (04:50)
Kind of the rest is history. just actually went full time into real estate last year, ⁓ June of last year. Went full time in, so that’s what I’m saying.

Dylan Silver (04:59)
So 2021,

2024, what was the balancing act like of having a job and then also doing real estate and trying to see, hey, how do I go full time with this? How did you manage it?

Chelsea Westover (05:58)
I wouldn’t say balance was a good word. There was not a lot of balance there. It was wake up, work from six to two at my government job. I was very privileged to have the opportunity to only have to work six to two and be able to get my job done. And then after that, it was driving home, making phone calls. Then it was, I’d be at the gym taking phone calls, sending emails. I’d come home, I’d be writing up different things, with dendums and stuff like that for the side gig that I had at the time. And it pretty much was weekend.

Dylan Silver (06:11)
Yeah.

Chelsea Westover (06:28)
I would try to catch up with anything that I was doing on the side. So it was really a little bit of work and a lot of extra extra time spent trying to continue to grow this because I just enjoyed it so much.

Dylan Silver (06:41)
I have yet to get a property in my name or an LLC that I own, but I was a and still am a wholesaler. And when people would ask me, you know, what it is that you’re doing, I would explain to them wholesale and they would kind of look at me blankly like, what do you mean you’re selling contracts? Like, are you a realtor? At that time, I was not. And so I just kind of figured like, well, I guess I’m doing this niche thing.

Chelsea Westover (06:49)
Nice.

Dylan Silver (07:04)
But I really, really, really, really loved what I was doing. And that’s how I knew, OK, this is something that’s going to be potentially a long term thing for me because no other quote unquote job, which I really wouldn’t call it a job. Honestly, it was fun for me. ⁓ And it made money. So I was like, this is great. And it was honestly solving a problem. You can relate to this as someone who’s done wholesale. People who are in distressed situations honestly need someone to come in and intervene. Otherwise, they’re going to lose their house, right?

Chelsea Westover (07:32)
Yeah, no, a hundred percent. So I’d worked for a wholesale company, started off in acquisitions, quickly found out that I have a background in project management. did project management for the government, grew up doing something like that through my career in the corporate world. And then when I was working for that wholesaler, did acquisitions, then quickly slid into their…

which at the time that wasn’t really a thing as much back then. I mean, they were there, but a lot of investors didn’t really know about creative finance transaction coordinators. And so it really was just like the glove fit exactly like you’re saying. It didn’t feel like work. was a lot of people thought it looked stressful and you’re running around with, looks like you’re a chicken with your head cut off, running around trying to get these transactions closed and you’re a wholesaler. So you can completely understand that.

Dylan Silver (08:01)
Yeah?

Chelsea Westover (08:18)
But yes, I’ve worked with so many wholesalers and I can’t tell you how many times it’s that heartwarming story of we just saved somebody from a really bad situation. And so you’re 100 % correct. When I try to even explain wholesaling, let alone creative financing to people, my mom is like, you’re doing something illegal. And I’m like, no, no, no, no, no, just because you don’t know what it is doesn’t mean that it’s illegal. It is very much legal. You just have to do it the right way. And it helps.

Dylan Silver (08:29)
Yeah.

Chelsea Westover (08:45)
So many people have so many examples of how it can really get people out of bad situations. It’s definitely something that needs to be out there.

Dylan Silver (08:52)
is a family from Maryland area or mom and dad from Maryland area.

Chelsea Westover (08:56)
Both from both from Maryland

Dylan Silver (08:58)
I have family in East Coast, in New Jersey, in New York, and I mean just the price of homes out there. I couldn’t qualify for a home out there. would be $220,000 a year, probably on the low end, honestly, to qualify for the type of home, very middle class neighborhood that I grew up in. And so to find out that there’s people out there wrangling wholesale deals for like $5,000, getting them under contract, assigning them.

you making a spread. It’s like, what is going on out here? I tell this to my mother and she’s like, what are you doing? So I said, okay, well, I guess no, I’m not gonna explain exactly everything down to the last detail, but it is interesting because there’s some other markets in the country, Texas, which is where I’m licensed as a realtor, where there’s so much, I would say, ⁓ enthusiasm around real estate investing that a lot of these strategies are kind of more well known, maybe not.

in the vernacular of everybody, but people know about it. People have received mailers and so on and so forth. What’s it like out there in West Virginia? know, I’m unfortunately know very, very little Chelsea about West Virginia. What’s the West Virginia market like?

Chelsea Westover (10:10)
Well, first off, you do know that I don’t appear to be the stereotype because I get a lot when people hear, you live in West Virginia, you have a lot of teeth, those types of things. Say, hey, do you shop at Walmart? Or whatever. You must use toothpaste. You’re the only person in the toothpaste aisle. So there’s ⁓ definitely a lot of stereotypes. ⁓ So to be quite frank with you, I

Dylan Silver (10:17)
Hahaha

Chelsea Westover (11:07)
I don’t actually do a lot in West Virginia. live here, but I’m on the border of West Virginia and Virginia, so kind of the DMV area.

Dylan Silver (11:14)
Hmm.

Chelsea Westover (11:14)
And

so, I mean, there’s so much. It’s like anywhere, right? There’s opportunity if you look to it. You just have to go and search for it. And for example, we have Baltimore City. mean, literally like you’re talking about, you can buy townhouses for $5,000. Now, do you want to? Depends on what your strategy is, right? And how much risk you’re willing to take and how much of what neighborhood you’re willing to invest in. But there’s definitely opportunity between Virginia.

Dylan Silver (11:32)
No.

Chelsea Westover (11:40)
between Maryland, between DC. mean, they’re just, all over. People are, we actually have a very, we’re very fortunate to have a really good community here for investing. And we do, so I do have properties in West Virginia. West Virginia market is still pretty hot. So actually from a wholesaling perspective, it is a little bit harder to lock up deals because the market is just still pretty good where I’m at.

Dylan Silver (12:04)
It’s an interesting thing because I think a lot of people gloss over some areas. West Virginia may not get as much national acclaim as some other areas. But I mean, I’ve spoken to wholesalers and investors in like Cleveland, Ohio, in Detroit, Michigan. They’re like, it’s a lot of the strategies that aren’t working elsewhere are still working out there. Like, you can find deals on the MLS for you know, 70 % of ARV minus repairs at cash flow. And it’s like, oh, this is great. And then other people would be like, I’m not buying in Detroit, and so on and so forth. But

When I think of the deals that I’ve walked into and some of the homes that I’ve walked into, I know I’m the last person to say I’m not gonna buy out there. Because some of the, honestly, crazy situations that I’ve walked into, this is where, in my opinion, investors and wholesalers really shine. Because when you’re dealing with potential, someone’s going through a medical issue, someone’s going through financial distress, divorce, death, and you know.

I don’t know very many realtors of which I am one that I gotta step in and say, hey, let’s go list this, you know, very, very distressed property and be optimistic about it. So it does require a different type of lens to view a deal through. I’m curious pivoting a bit here, Chelsea, your company TC Collective, Consulting to investors, how did this come about and what’s it like in the business? What’s a day to day like in the business?

Chelsea Westover (13:10)
Thank

Very much like wholesaling. I’m gonna be honest with you. ⁓ So it actually started off, I started off on my own. Truflow TC was my business at the time, did that.

And then ⁓ long story short, came into the TC Collective. So this was a company that was started before I came into them. Started working for them for a little bit, because I wanted to join a team. So I started doing TC stuff way before we had anyone out there that was providing guidance or community or anything. I kind of literally just learned the ropes myself and developed my own processes and systems and was introduced to this team and said,

yeah, this would be awesome to be a part of a team with rock star people. And so I had the opportunity to actually step into ownership with that and pretty much took over and ran full force with it. So I own it with two other women and it’s been super rewarding. What does my day to day look like? Well, it’s probably very similar to you chasing sellers, chasing buyers, checking in with title, ⁓ making sure that we have everything we need for closings. It’s just.

You never know when something’s going to happen. You can try to prepare as much as possible for these deals, but it’s like the Wild, Wild West. I work with it. Literally.

Dylan Silver (14:36)
enough.

It is like the wild wild west. Why do you said that? That is exactly what it’s like. I remember

seeing some deals, you’ve probably dealt with this probably hundreds of times where the investors like, yeah, we won’t need an appraisal. We won’t need an inspection. Our lenders good, everything’s good. No work, no issues, no issues. And then it gets to like the day before closing. And they’re like, we need an inspection to at which point we started saying like, Hey, we actually we understand you have

this approval letter, we understand that you’re bulletproof with your lender. We need to talk to the lender. And they’re like, no, I don’t want to talk. I don’t want you to talk to the lender. No, we need to talk to the lender. Give me the lenders. it a, who is this person? Right? And so oftentimes, cause it’s still, like you said, the wild, wild west, I like to say, and I think this is accurate. Sometimes lenders can be a very formal, like a hedge fund type of situation.

Chelsea Westover (15:25)
Yep.

Dylan Silver (15:38)
very, very much structured. Other times it’s a bunch of bros or a bunch of gals who just decided to lend some money out. And it’s like they might have some general guidelines, but basically they just kind of trust this person. Well, now they’re about to loan out $250,000. So they might now have some, some questions the day before closing, which they didn’t previously disclose. And so it is very, very challenging. think in a lot of these ways,

Chelsea Westover (15:43)
Hahaha!

Dylan Silver (16:46)
transaction coordination, I think is such a big thing.

Because investors, it’s fun, but it’s also a lot of work and can be very tenuous, require a lot of expertise. When people are coming to you, what are their expectations as far as the load that you will handle? Is it like, hey, we’re gonna basically handle everything from the time you have it under contract to closing? Or is it like, hey, we’re gonna do the coordination, meaning the messages between parties, but we’re not gonna kind of work through these problems that come up, that’s your job.

Chelsea Westover (17:18)
No, that’s a great question. get this a lot actually of what does a TC actually do? And I actually, don’t, I’m going to be brutally honest with you.

don’t like using the term TC because we don’t coordinate, we manage. That’s how we specifically run transactions is I want to be able to manage everything from whenever you bring me onto the deal up until closing. And then we can get involved after closing, depending on the type of transaction, especially with, uh, creative financing. So I don’t know how familiar you are with that. We don’t actually work with lenders that often.

I’m going to be brutally honest, we primarily work in the creative space where there’s not lenders involved most of the time. So it becomes that much more tricky because of the types of deals that we are closing. And so the level of expertise, it’s not, hey, give everything to a lender, just give the lender what they need and then close. These are subject to transactions, right? These are seller financing where you really need to make sure that you’re setting yourself up for success and not just the buyer, but also the seller. Because if the buyer is not set up for success,

Dylan Silver (17:55)
Yeah.

Chelsea Westover (18:14)
is the seller and neither is the wholesaler because that’s a huge liability to them too. Everyone thinks that they can’t run to the deals done. They’re like, I’m off, I’m done. No, that’s not how it works. Like the seller can come back after everybody in that deal. I’ve seen it happen before, unfortunately. So to answer your question, kind of we manage, we don’t coordinate. We literally ask that we control everything because if you try to step in, you may be stepping on something and then blow the deal up. And so we literally will take everything, give us everything you got.

We will keep you updated. let you know what’s going on. We’ll bring you back in if there’s renegotiations or we’re having trouble. But for the most part, we want to take over and just run with it. You go do what you are good at. You go find leads, bring more leads in. You deal with all of that. Let us keep the back end and really be that strong partner to make sure that your back end is handled and organized and push the chaos forward in an organized fashion.

Dylan Silver (19:09)
Wrangle some deals and then handle the chaos, right? Are you regional based out of meaning the the deals that you take are based in that DMV area? Are you across the country? That’s the challenging thing

Chelsea Westover (19:11)
Yes, exactly.

We’re across the country. Yeah, so we do.

It’s actually not. It’s more, so it’s funny. I was actually talking to somebody about this the other day. I prefer to be regional or national because I’ve seen so many different types of transactions. I’ve worked with so many attorneys, so many different title companies, so many different investors. I’ve seen so many different types of deals and how to structure them and things that you can consider to the point where we’ve done deals where it doesn’t even have a title. I don’t even know what you would call it. It’s not subject to seller financing, morby method. ⁓

something I’d never seen before through these investors that are just, I mean, again, wild, west. You can really think of anything. And as long as you get the right people involved and everyone understands the risk and you sign off on it, there’s no reason you can’t move it forward. So it’s actually awesome to be able to have that much experience.

Dylan Silver (20:00)
Right.

It is. It makes me think I got to get a deal under contract somewhere and ⁓ reach out to you guys and handle some of the load there. ⁓ Chelsea, are coming up on time here. Where can folks go if maybe they have a deal they’d like your feedback on or if they’d like to reach out to you?

Chelsea Westover (20:24)
Yeah, absolutely. So they can find me on primarily on Facebook, try to be super active there. So Charles Westover, Chelsea Westover, and then on there you can also find I have a link, you can book an appointment with me. So love to be able to connect with other people. So I just put my calendar up there. There’s different slots and appointments that you can sign up for. So if there’s a deal or if you have a question about a deal or want to see what a TC might be able to help you with, I would love to be able to connect with you. There’s also Instagram, Chelsea Westover ⁓ on Instagram too. So you can

Those are two ⁓ of the platforms that I’m mostly active on.

Dylan Silver (20:59)
Chelsea, thank you so much for coming on the show here today.

Chelsea Westover (21:02)
I really appreciate you having me. Thanks, Dylan.