How Tasha DeRegis Went From Flipping Houses to Building an $80K Airbnb Rental

Tasha (00:00)
I built a property for $268,000 was like my all in cost of new construction. It’s a 2300 square foot

10 minutes from downtown Nashville, adding that $85,000 land acquisition cost. And now it’s in Airbnb and it’s generating me about 80K a year. And I actually house hacked it at first. So while living in the property, I had a mother-in-law suite in the back and just rent out the mother-in-law suite on Airbnb and I don’t have to pay a mortgage.

Quentin (02:04)
Hello, everyone. Welcome to the Real Estate Pros podcast. I am your host, Q Edmonds, and I’m excited to be here today. Have another fantastic guest. And I am so thrilled that we get to look at business through her eyes, through her lens, look at real estate through her experience. And she definitely has some experience, y’all. She’s definitely not a novice. And I cannot wait for you to learn just her journey.

She’s done multiple things very well. And so I know we’re going to get some really, really good information. We’re going to to clean some very, very good experience. And so I want to introduce you all to Miss Tasha DeRegis. Miss Tasha, you doing today,

Tasha (02:45)
I’m doing great, how about yourself?

Quentin (02:47)
I’m doing great, doing great. I’m glad to be here. Glad you’re here. And listen, I am the type. I like to dive right in, right? So I would love for you to tell the people what’s your main focus these days. If you don’t mind, give us a little bit of an origin story, kind of how you got into the space that you’re in. And then let them know what part of the world you’re in. People love to know geographically. So what you’re up to, your origin story, and where you are. Tasha, you got the floor.

Tasha (03:13)
Yeah, sure. So I am based in Nashville, Tennessee, and I started about 10 years ago in Flipping Houses. That’s how I got my foot in the door.

and after about a year or two of flipping houses, decided to go full time into real estate. So quit all my jobs and got my real estate license to kind of supplement my income, on the, the sell side. And then from there, I found a bottleneck of finding deals. think everybody can kind of relate to that. And so I decided to get into wholesaling to kind of satiate my own pipeline. and when I got into wholesaling.

I realized I loved it and it was almost better than flipping houses really at the time. So I got more so into buy and holds and a new construction at that point. So that brings me to where I am today where I am mainly just sourcing off market deals and doing new construction.

Quentin (04:09)
Love it.

I love it. Well, thank you, ma’am. Thank you for taking me through the journey, how you got started, kind of where you are now. And as you was talking, I was actively listening, writing some things now. So I’m going regurgitate some things back to you, reiterate some things you said, because I want to make a statement that asks you a question. All right? And so I started flipping houses about 10 years ago. After one or two years, you quit your jobs and went all in. It was like, I’m out. I’m all in now. ⁓

Tasha (05:18)
and

Quentin (05:28)
Got into the bottleneck of finding more deals that led you to wholesaling. I’m wholesaling you to some buy and hold that kind of went into the new construction. And this is kind of like how you’re in the space that you’re in now. Was that a pretty good summarization? All right. Love it. Love it. And so I do that because one, I’m kind of flared for the dramatics, right? So I’m trying to build up to this statement I’m about to say. And so I often say on each podcast,

Tasha (05:43)
Yeah, exactly.

Quentin (05:56)
that destiny has no wasted moments, right? Meaning like, no matter what we go through in life, we’re building moments and we’re borrowing from the moments, whether they’re failures, whether it’s their success, it’s reinforcing our mindset, it’s giving us our drive and our purpose. And so all the moments has kind of led to where we are now. So Tasha, would love to know, throughout the journey, throughout your moments, what have they taught you about yourself?

Tasha (05:59)
Yeah.

Quentin (06:22)
Have they taught you discipline, resilience? Like, what is the moments taught you about you?

Tasha (06:26)
Oh, that’s a really good question. So I think all the moments I’ve been through in the last 10 years have really shown me that no matter what it is that I want to do, I can do it.

So that’s been kind of what I’ve taken away from it. There’s been a lot of ups, a lot of downs. There’s been market shifts, there’s been market booms, and through it all, I’ve been able to always pivot and maintain. So yeah, I can basically handle anything and I fully trust myself to get to the next level.

Quentin (07:01)
I love that. Great. Thank you for answering that the way you did. mean, of course, people answer it in different ways. But the way you answered it triggered me because you talked about trusting yourself. And I think that’s one of the reasons why I asked that question is because I want people to be able to reflect back on how they got to where they are.

Tasha (07:13)
Yeah.

Quentin (07:23)
I want people to be able to pull from the experiences that they’ve been through in their life. They got them to where they are because as you mentioned, things, sometimes things is not smooth sailing. And so when you hit bumps in the road, road, where are you going to pull from? You got to be able to pull from yourself. And so one of my mentors told me, when you know who you are, you know what to do. And I think you just summed that up perfectly. You can trust yourself. So when you know who you are, you trust yourself. Throw me in any situation.

Tasha (07:38)
Mm-hmm.

Quentin (07:53)
I may cry, I may cry for an hour, I may cry for a day, but eventually, you know what? I trust myself to get over it. You know what I mean? And so I appreciate your answer. I really do. Yes, ma’am. Absolutely. So so you’re no stranger to tough times, no stranger to adversity. So how does adversity look in your world and what’s your mindset once adversity hit? Like, how do you normally overcome it? Like, what are your next steps to to attack adversity?

Tasha (08:21)
Yeah, so when you say adversity, you just mean like, like in what frame?

Quentin (08:28)
That’s a great question. as you talked about, you got to pivot sometimes so things doesn’t go the way we expect. Sometimes deals don’t go the way we think. know, sometimes, you know, like you said, the market shifts. So everybody faces adversity, right? And I’m just trying to get from your perspective. Maybe somebody can borrow from your experience of how you faced adversity and overcame it.

Tasha (08:48)
yeah. So I think my first experience with adversity in this business was finding my bottleneck of deals. And so my next step is, well, if that’s my bottleneck, then how do I solve that problem? And so I sought out ways that other people were using. Like obviously agents are bringing in deals off market and wholesalers had, you know, these nice big checks at the end of our transaction. And so I was like, what are other people doing to get what I want?

And so just through talking to people, learning from other people who were doing what I wanted to be doing, I was then able to learn how to find off market properties. From there, you know, I was realizing that in flipping houses, I was leaving a lot of money on the table because people’s properties were appreciating. mean, I don’t know if it was the same in every market in the U.S., but in Nashville, we saw, I mean, up to like 20 % increases in just a couple of years on our property.

Like for example, in 2016, my first flip I sold for $198,000. Today it’s worth $365,000.

So in seeing that during the rise of real estate in Nashville, I was like, okay, well, now my next pain point is I feel like I’m leaving money on the table because if I was holding these properties, then I would have appreciating assets. So that it was, how do I figure out how to hold onto a property, how to choose a rental property, how to get the loan for the rental property, all of that. through that, I just talked to a bunch of other

investors who were already doing rental properties as like their main gig, learned numbers and learned what kind of lenders to work with. And then I was able to get six awesome rental properties during the height of the market at like pre-hype prices. So they all had six figures of equity in them and a minimum of $800 a month in cashflow.

And I learned how to do short-term rentals as well. And then the next thing in this business that I noticed in terms of adversity was COVID hit. People weren’t pulling back fully, but they’re pulling back a little bit. And I had this awesome lot for $85,000, literally 10 minutes from downtown Nashville, which is like crazy and prime, you know, short-term rental opportunity. So I couldn’t wholesale it and I’d never built a property before.

So I decided to just go for it and ask people, know, hey, you build properties. Like, how do you do it? Like, hey, you build properties. What’s the due diligence look like? Or, you know, what kind of lender can I use? And so through that, I was able to get my first buy and hold. And it’s probably my best buy and hold of all of them.

I built a property for $268,000 was like my all in cost of new construction. It’s a 2300 square foot

10 minutes from downtown Nashville, adding that $85,000 land acquisition cost. And now it’s in Airbnb and it’s generating me about 80K a year. And I actually house hacked it at first. So while living in the property, I had a mother-in-law suite in the back and just rent out the mother-in-law suite on Airbnb and I don’t have to pay a mortgage.

So yeah.

Quentin (12:45)
Well,

well, well, strategies, strategies, strategies. Absolutely. No, I love you. Thank you. Thank you for sharing that. And listen, y’all, that’s how you pivot in adversity. That’s how you pivot in adversity. I thank you. I appreciate you taking us through the journey of that, answering the question with that reflective answer. What’s next for you? Like, what is your next real goal? What is next for, what are you looking to solve for scale next?

Tasha (13:11)
Yeah, so my next real goal is just kind of like sustaining in this market. I’m doing partnerships with sellers on their land so that way, you know, I don’t have to bring money to the table. I can just partner with them and ⁓ collateralize the land for the loan. And so I can make them money. They can help me.

on my journey to building more new construction. And it’s just more so like using leverage rather than like being aggressive in this market. But I’ve also been getting into mergers and acquisitions. So I want to buy a service based business, not to go too off topic, but I’m also doing AI automations. So that’s something I’ve been super excited about. It’s helping me a lot with ⁓ making my marketing more passive, my direct to seller marketing.

more passive and it’s been really fun to learn and like see the automations come to life.

Quentin (14:11)
Absolutely.

No, I love it. love it. ⁓ this is so good. So let me ask you this. So mergers and acquisitions, you boldly walked up to somebody when you was doing this, when you was doing the buying hole. Now that’s, you said your best buying hole. So I want to ask you and get your perspective on this word, relationship. When you hear the word relationship, what comes to mind for you?

Tasha (15:20)
When I hear the word relationship, especially in terms of like business and real estate, it’s trust, steadiness, communication, knowledge, and balance.

Quentin (15:28)
Mm.

Yeah. I don’t think that’s a word I heard quite that often when it comes to relationship. And I think that’s great. That’s a great word, balance. Wow. Yeah, I’ve never quite heard that. That’s really good. Because there’s so many different components that go into a relationship, communication. I love how you said trust. And I think balance is one. Because balance leads to boundaries, right? Like, you know.

what you can hold, what you can’t. Sometimes you got to put up a strong bound and be like, hey, you know, this is how things are going to have to go in order for me to stay balanced, for me to stay, you know, on the level where I need to. And so that’s great. Now I love that. That’s, that’s a really, really great answer to that question. Is there any topic that I have not brought up that you would like to talk about? Is there any words of inspiration, education, motivation, or like maybe you came in with something on your mind.

and you want to make sure that the viewers heard this. I just kind of want to create the floor, up the, create space, open up the floor. If there’s a message that you want to land, I want to make space for it.

Tasha (16:41)
Yeah, totally. So for anybody who is considering getting into real estate or struggling in real estate right now, I just want you to know.

⁓ You’re not alone. It’s a tough market. You can still do it and you can still make money. You can still be successful in this industry, regardless of what’s going on with interest rates or, you know, sellers having really high expectations post market boom. You just have to be conservative and you have to be savvy. So it’s just all about trusting yourself to be able to know what the next move is. So just finding your bottleneck and finding a solution for it.

is what you need to do, but it’s doable. It’s just not as easy as it was, which means that the winners are going to stay in and then the people who might need to move on to something else can move on to something else. But we’re all winners here. We’re all capable of being winners. So if you just keep your head down and you talk to enough people and you learn enough knowledge and you’re always figuring out what’s the next step to pivot, you’re going to be successful and you’re going to be able to make it through. But it’s just not the time to be aggressive unless you have

have a no-brainer property that you’re working on.

Quentin (17:53)
Yeah, thank you. Thank you for your message. And one consistent message that I hear from you, even with the way you just explained that, is really having people trust themselves, like understand where they are.

and trust what they’re doing. Yeah, analyze it, look at it, look at the deal, but ultimately trust yourself, trust who you are within your space. so I love that. I love your messaging. ⁓ If someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you,

Tasha (18:23)
They could follow me on Instagram @tashar0se or add me on Facebook, TashaRose or LinkedIn. I’m most responsive on Instagram.

Quentin (18:40)
Gotcha, gotcha. Well, listen, I want to say three things to you sincerely. First, thank you for your time, right? I believe time is our most precious commodity. So thank you for giving us some of your time. You can be doing anything. I mean, you got businesses to run, you got things to do, but you gave us your time. So I appreciate that. Secondly, thank you for your story. Thank you for what I call like the gift of your transparency, the gift of your authenticity, even the gift of your vulnerability. These are things that you did not have to share.

but you share things. And I believe that stories plant seeds in people. We may never see the growth, but the seed is there. And at any given time, that seed can sprout up. So it can be a month from now, five years from now, but the seed is there. So I really believe you planted some seeds for people. And lastly, thank you for your mindset. Thank you for the way you think and bringing that mindset to this platform. I greatly appreciate you coming on now.

Tasha (19:36)
Absolutely, thanks for having me.

Quentin (19:38)
Absolutely. Listen, y’all heard Ms. Tasha looking in show notes. Please get in contact with her, but definitely make sure you are subscribed here because I promise you we’re going to continue to bring up amazing people just like Tasha. So ma’am, thank you again. And everyone else, listen, y’all have a fantastic day.