Financial Freedom with Rentals After 3 Years of Pure Hustle

Summary

BiggerPockets Real Estate Podcast: Episode Summary

Episode: Financial Freedom with Rentals After 3 Years of Pure Hustle
Release Date: July 14, 2025
Host: Dave Meyer
Guest: Taylor Wing, Real Estate Investor

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Introduction

In this compelling episode of the BiggerPockets Real Estate Podcast, host Dave Meyer welcomes back Taylor Wing, an investor who transitioned from a demanding military career to building a robust real estate portfolio. Over three years, Taylor scaled from a single house hack to owning over 30 rental properties across three different markets. This transformation allowed him to prioritize his family's lifestyle and pursue a fulfilling new career in real estate.

Guest Background

Taylor Wing's journey into real estate began during his tenure as an active-duty army officer. Introduced to real estate through influential resources like "Rich Dad, Poor Dad" and mentorship platforms such as BiggerPockets, Taylor harnessed his military discipline to aggressively pursue property investments.

[02:26] Taylor Wing: "I read 'Rich Dad, Poor Dad,' got super heavy into real estate... I found some real estate mentors and started flipping houses, doing BRRRR, creative financing, wholesaling... [it] changed my life."

Early Investment Strategies

While still serving in the military, Taylor employed a variety of acquisition strategies to build his portfolio. Leveraging VA and FHA loans, he focused on low down payment options to maximize his investments without overextending financially.

[04:52] Taylor Wing: "I was probably buying maybe one a month at that point... using hard money loans, trying to cash out, refinance on the back end... I still have my very first VA loan locked in at like 2.7% interest and never given."

Taylor's approach was hands-on, involving direct marketing efforts such as door knocking and cold calling, given the limited funds for a marketing budget. He strategically targeted single-family homes suitable for military families, ensuring a steady tenant base.

Transition from Military to Civilian Life and Real Estate

In the summer of 2023, Taylor transitioned out of the military, coinciding with the birth of his son. This pivotal moment led him to fully commit to real estate, relocating to South Florida to embrace a lifestyle more aligned with his family's needs. This move marked a strategic shift from aggressive acquisition to optimizing his existing portfolio for better cash flow and lifestyle balance.

[07:08] Taylor Wing: "Half a year after my service obligation, I hit that number... those years of sacrifice did end up paying off for us."

Portfolio Management and Optimization

With a portfolio of approximately 35 units, Taylor shifted his focus from merely increasing the number of properties to enhancing cash flow and optimizing his lifestyle. This entailed a thorough analysis of his existing assets to identify high-performing properties and eliminate those that were underperforming or causing undue stress.

[14:30] Taylor Wing: "We had roughly around 35 units. We're still around that number now. But what we really focused on now is life optimization and cash flow."

Taylor emphasized the importance of financial metrics over sheer door count, advocating for a data-driven approach to portfolio management. This strategic realignment allowed him to maintain a stable number of properties while maximizing income and minimizing effort.

Rebalancing and 1031 Exchanges

A significant aspect of Taylor's portfolio optimization involved rebalancing his assets through the use of 1031 exchanges. This strategy enabled him to sell underperforming properties without incurring immediate capital gains taxes, allowing the reinvestment of equity into more lucrative opportunities.

[28:21] Taylor Wing: "Once I figured out how to do a 1031 exchange, that's what really made the most sense because I was able to get that kind of maybe headache property off my plate and move that money into properties that will actually get us towards that financial freedom number."

By utilizing 1031 exchanges, Taylor efficiently managed his portfolio, rechanneling funds from problematic properties to those with better cash flow potential, thereby enhancing overall portfolio performance.

Specific Deal Examples

Taylor provided insights into his recent acquisitions, particularly in Fayetteville, where he employed the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) strategy. He detailed how he sourced properties at competitive prices, conducted cosmetic renovations, and achieved impressive cash-on-cash returns.

[34:07] Taylor Wing: "I bought two deals in Fayetteville last year. They're both BRRRR deals... buying them in the 130s, getting them appraised for like the 220 to 240 range... cash flow is probably like 300 bucks maybe if you're lucky."

This approach not only maximized his investment returns but also ensured a scalable and sustainable growth of his rental portfolio.

Lessons Learned and Advice

Throughout the conversation, Taylor shared invaluable lessons from his real estate journey. He highlighted the importance of:

1. Professional Support: Engaging a competent CPA and property management company to streamline operations and financial management.

   [19:18] Taylor Wing: "We hired a great CPA and accountant. They helped us clean up our books and pull reports per property to see which ones are working."

2. Data-Driven Decision Making: Regularly analyzing financial metrics to assess property performance and make informed investment decisions.

3. Flexibility and Adaptability: Being willing to sell underperforming assets and reinvest in more profitable opportunities to maintain a healthy portfolio.

4. Focus on Lifestyle: Prioritizing cash flow and lifestyle over the number of properties, ensuring that real estate investments align with personal and family goals.

[38:01] Taylor Wing: "A lot of those other metrics don't matter as much. It's all about lifestyle. Real estate is a powerful tool to create the lifestyle you want... enjoy the money, spend time with family."

Taylor emphasized that real estate should serve as a means to achieve financial freedom and personal well-being, rather than an end in itself.

Conclusion

Taylor Wing's story is a testament to the transformative power of disciplined real estate investing. From managing properties while serving in the military to optimizing a diverse portfolio for maximum cash flow and lifestyle balance, Taylor exemplifies the BiggerPockets ethos of achieving financial freedom through strategic real estate investments. His journey underscores the importance of adaptability, professional support, and a focus on meaningful financial metrics, offering valuable lessons for both novice and seasoned investors alike.

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Notable Quotes:

• Taylor Wing [02:26]: "Real estate changed my life. So grateful I found BiggerPockets and my mentors."

• Taylor Wing [14:59]: "We hit that level where we have a foundational level of financial freedom where we feel comfortable paying our base level expenses."

• Taylor Wing [22:01]: "Those guys [CPA and accountant] are really important to help you go get to that next level."

• Taylor Wing [37:22]: "Even one a year, you're making that forward momentum still. It's still awesome."

• Taylor Wing [38:01]: "Real estate is a powerful tool to help you get there [create the lifestyle]."

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This episode provides a comprehensive look into the strategic evolution of a real estate investor balancing aggressive growth with sustainable lifestyle choices. Taylor Wing's experiences offer actionable insights and inspiration for listeners aiming to achieve financial independence through real estate.

Transcript

[Dave Meyer]

This investor started with a single house hack. Three years later, he had more than 30 rental properties and was able to transition out of his demanding military career and into the life he always envisioned for his family. Now he's acquiring multiple new properties per year, but he spends most of his time leaning into what he calls the Florida lifestyle. This isn't some secret formula that you can't execute. It's the result of following a reliable, sustainable path to investing. Let's hear how it works. Foreign what's up, everyone? I'm Dave Meyer. I've been buying rental properties for 15 years, and on this podcast we teach you how to achieve financial freedom through real estate investing. Today's guest is investor Taylor Wing. Taylor started his investing career when he was an active duty army officer, looking for the financial security that would allow him to leave the military when his service commitment was up. He started with just a single house hack and was able to grow his portfolio to more than 30 units across three different markets in just three years. That real estate investing has allowed him now to prioritize his family's lifestyle, live where he wanted, and to find a new career that's fulfilling for him at this stage of life. Taylor shared some of his story a few years back on this podcast on episode six. 77. But I wanted to have him back on the show because a lot has changed in his investing since then. He still has around 30 units, but many of those properties have turned over as he's looked to simplify his investing so he can spend more time with his growing family. He's still trading out and finding and acquiring great new properties every year, but he's found ways to do it with much less pavement pounding than before. These are really important skills that every investor needs to learn, whether you're just starting your real estate journey or you're in the harvesting phase like Taylor is. Let's bring them on. Taylor, welcome Back to the BiggerPockets podcast. Thanks for being here.

[Taylor Wing]

Good morning, Dave, and thanks for having me back.

[Dave Meyer]

Yeah, this is going to be a lot of fun. I hope that a lot of you have heard Taylor's first episode. It was 677 back in October of 2022. But for those who haven't yet listened to that one, Taylor, maybe give us a little bit background about yourself, how you got into real estate in the first place.

[Taylor Wing]

Yeah. So just a quick Cliff Notes on me again. Born and raised in California, pretty much straight out of high school. Went to the academy up at West Point, was an army guy, commissioned, graduated in 2018, decided to be an artilleryman, went to airborne school, did the paratrooper thing, and then after about five and a half years, exited service. So last time I was on this podcast, I was still in the army actually, and real estate was my side hustle. And. And we are like in a heavy acquisitions mode. Didn't have any kids back then either, so I devoted all my spare time to real estate. And now where we are today is a complete 180. So lifestyle has changed a ton. Of course, we transitioned out of the military, started our family, and doing real estate full time.

[Dave Meyer]

That's great, man. Well, congrats. It sounds like you've made a lot of progress. I'm curious, going to West Point, were you like originally thinking of having a career in the military, like long term?

[Taylor Wing]

Yeah, that was of course the, you know, original game plan going into the academy, you know, trying to make it up the ranks as far as I could. But while I was in the service, you know, I read of course, like everyone, rich dad, poor dad, got super heavy into real estate. I found some real estate mentors too, and started flipping houses, doing burrs, doing creative financing, some wholesaling, and just kind of fell in love with real estate and real estate. Changed my life. So super grateful I found bigger pockets and I found my mentors. It changed the trajectory of my life. So instead of doing a career in the military, of course we've. We did a. We did a big pivot.

[Dave Meyer]

Well, that's amazing. Well, thank you for your service, but I totally understand, whatever, whether it's military, corporate life, whatever. A lot of people read that book, rich dad, poor dad. Oh yeah, get the bug and move into it. But it sounds like you found something you really like. We're going to get to what Taylor's been doing now, but I just want to catch everyone up to what he was doing in the beginning. So what was it like investing while you were still in the military? What kind of deals were you looking for at that point?

[Taylor Wing]

Yeah, so in the military, we did pretty much any acquisition strategy you can think of. I did house hacking with VA loans, FHA loans, a lot of low down payment options. You know, as a government employee, didn't make a ton of money back then. I was brand new Butter Bar, second lieutenant. We made decent money, but not enough to just start buying houses like I was, I was probably buying maybe one a month at that point.

[Dave Meyer]

You were buying one a month how?

[Taylor Wing]

A lot of low down payment options like sub 2 seller finance, brrrr. Strategy using hard Money loans with trying to cash out, refinance on the back end. And of course, VA loans are a super powerful tool for all my veterans out there where you can buy a property, zero down, live in it for a while, and then you can either flip it on the back end and pull that equity back out and get it into your next VA loan, or you can hold onto it and keep renting it. I still have my very first VA loan locked in at like 2.7% interest and never given. Now I have so much, so much equities built up after Covid. But the, but the interest rate is so great. I don't know if I ever want to sell that. So.

[Dave Meyer]

So when you were doing this, were you just buying where you were stationed at the time or did you pick like one hub that you wanted to be investing in?

[Taylor Wing]

So I actually invested where I was stationed. So I was stationed in Fort Bragg, Fayetteville, North Carolina. So it was a great rental market and I love military markets. Um, so I started investing exactly where I was. And I was real grassroots with it. I was door knocking, you know, I was cold calling. I was boots on the ground. I didn't have much money for a marketing budget, so I was really hustling My, my 5 to 9 was, was really out there getting after it, I bet.

[Dave Meyer]

Yeah. And so were you renting mostly to other folks in the military?

[Taylor Wing]

A combination? Pretty much. Right off the bat. I hired a professional management company because it was just too much for me to keep on, you know, fronting the acquisitions, doing the management, and still being in the army. So I pretty much hired a professional property management right at the gate. But definitely a lot of military families for sure. And my kind of niche in that market has always been single family homes, three bedroom, two bath typically, or if not more bedrooms. So it's, you know, perfect for your typical family is kind of what I always like to cater to over there.

[Dave Meyer]

How long were you doing that when you were actually still in the military? Building up this portfolio pretty aggressively?

[Taylor Wing]

Yeah, very aggressive. Really hustling for probably like a good four years.

[Dave Meyer]

Oh, wow.

[Taylor Wing]

While I was in the service. Yeah. And I had a service obligation, so I kind of set a self goal that was like, you know, can I make enough cash flow from this portfolio to match my government paycheck to give me that flexibility to transition out if I wanted to once my commitment was up? So that was kind of like my challenge I had set for myself back then.

[Dave Meyer]

And how close were you able to get while you were still in the.

[Taylor Wing]

Service, she made a little bit more from the passive than I was making from my paycheck. So luckily, it timed out perfectly to where maybe like a half year after my service obligation, I hit that number. And that kind of gave us that green light to look at our options outside of military service, because at that point, my wife and I were looking to settle down, start a family and everything too. So the timing really worked out perfectly. And those years of sacrifice did end up paying off for us.

[Dave Meyer]

Okay, so that was sort of like just some background. You were on the show back in October 2022. What year time did you actually transition out of the military?

[Taylor Wing]

I transitioned out summer of 2023.

[Dave Meyer]

Okay, so a little bit later. And did you just keep doing the same kind of real estate approach at that point?

[Taylor Wing]

No, at that point, I did shift, and it was partially just because of our lifestyle and also because the market. If you remember around that time, o remember, interest rates more than doubled. It got crazy. You know, we got burned a little bit on some flips that were kind of sitting out there. Had a lot of money out there. And so really after, once I transitioned out, I was still doing real estate, but I didn't really quite have a game plan. I got out in, like, the same month I had my son.

[Dave Meyer]

Oh, wow.

[Taylor Wing]

So I moved to Florida, got out of the army all the same month down here in South Florida. So I pretty much went straight into dad mode. And the real estate kind of gave us more flexibility to give me that time to spend my wife and the newborn.

[Dave Meyer]

Well, congratulations on your. On your family. That must have been very exciting. How did you pick another market?

[Taylor Wing]

For me? I always invested where I lived because I like to touch and like to feel like to be involved. And, you know, that might not be the best option for everybody out there, especially in, like, high cost of living areas. But I went from Fort Bragg. I moved to Sioux Falls, South Dakota. So I bought, you know, a good handful of property out there, and then now we moved down here to Florida, and I've been buying stuff around here as well. So I've always invested where I lived.

[Dave Meyer]

When you went from North Carolina to Sioux Falls, what was different about that market and how do you adapt?

[Taylor Wing]

So interesting enough, the property values in South Dakota were actually higher than they were in North Carolina. So the numbers for long terms back then were not super sexy. And we found an interesting niche because my wife was travel nursing back then. And Sioux Falls has two large hospitals, which kind of service almost the whole state right there in the central region of the city. So we kind of focused on that because there's a lot of travel nurse contracts and that my wife was also being a part of. So we started buying small mom pop multifamily within a certain radius around these hospitals. And then we kind of really tailored to that travel nurse midterm rentals strategy. So Fort Bragg, we catered to military family, single family homes. Sioux Falls, really kind of more smaller apartment mom and pop catering to more of the travel nurses over there.

[Dave Meyer]

Was that a big change operationally for you going from, you know, doing more of the midterm rental style thing?

[Taylor Wing]

It was. That's when I got my wife more involved in real estate. Whether she liked it or not. She, I finally got her on board, you know, before it was just me kind of doing it all and, you know, she kind of let me do my thing. But really that once I got her involved in the travel nurse side, kind of more hospitality based a little bit. And she was a travel nurse, so she knows what travel nurses want, what they need. So she really helped me and I brought her into the business on that way.

[Dave Meyer]

Cool. Thank you for setting the stage for us, Taylor, and giving us a little bit of background. I want to shift the conversation. Talk about when you move to South Florida, what did your portfolio look like and what you've been up to in the last couple of years. But we do need to take one quick break. We'll be right back everyone. Just a reminder, if you are listening to this in the next couple of days, Henry Washington and I are doing our cash flow roadshow. So definitely follow along for all the content that we're going to be making. But if you are in the Chicago area, we have a free meetup on July 15th. And if you're in the Indianapolis area, we have a free meetup on July 16th. Make sure to RSVP because you got to do that before you come. You can go to biggerpockets.com roadshow to do just that.

[C]

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[Dave Meyer]

Welcome back to the Bigger Pockets podcast. I'm here with investor Taylor Wing. Before the break, he was catching us up on his portfolio. How he got started buying while he was still in the military in North Carolina and then in South Dakota. Taylor, you said then, you know, it was sort of a shift in your life where you were going from being in the military to starting a family, being out of the service. You moved to South Florida at that point. What did your portfolio look like back then?

[Taylor Wing]

It was very similar to how it is now, actually. We had roughly around 35 units. We're still around that number now. But what we really focused on now is life optimization and cash flow. A little bit before, I would have been more focused on number of doors, all these other arbitrary numbers that I was tracking. But really it came down to just cash flow and lifestyle. Once we had a family because we wanted to make as much money as possible with the least amount of effort possible.

[Dave Meyer]

I love that. Yes, don't we all?

[Taylor Wing]

I don't care about doors anymore. Really. The other metrics, even equity, I know, I appreciate, and it helped in appreciation. But cash flow is king right now. So what we did was we kind of strategized, we looked at our portfolio, we really dove into the numbers, which I didn't really do before. And we were trying to see, all right, which ones are really working, which ones are not, which ones are our performers and not. And we just started moving money around, did some 1031 exchanges, got some, some better properties. And so we're at the same unit count. But I think we've implemented systems to make it run a lot better so we can maximize that passive cash flow that's ultimately helping us pay our bills and helping us live our lifestyle.

[Dave Meyer]

Everything you just said we need to dive into. Because I think this is a really big topic for investors right now. A lot of people have fortunately, you know, built up some equity, built up a portfolio during, you know, the run up in all these prices. They have a lot of equity. And I get this question all the time, like, how are you rebalancing? How are you thinking about curating? So let's, let's talk about that. But first, you just mentioned that cash flow is your goal. You had previously said, though, that you had already replaced your income from the military, which is awesome. What was your new goal and how did you set it? Like, do you have a specific cash flow number you're trying to get to, or is it just, you know, maximize it indefinitely?

[Taylor Wing]

For me, it's honestly just maximizing it indefinitely. And I did suffer from lifestyle creep because once I got down here, I wanted to live the Florida lifestyle.

[Dave Meyer]

Do you buy a boat?

[Taylor Wing]

Not a boat yet, but that's in the works. But Got the biggest house I possibly could. I'm on the water down here on the intercoastal. You know, we built a pool and everything and did a bunch of upgrades. So we know we're really living the Florida lifestyle, but really just trying to maximize that number as much as we can. But I would say that we hit that level where I feel like we have a foundational level of financial freedom where we feel comfortable paying our, like, base level expenses. And so whenever we go out to work, we're just basically helping build that portfolio and saving towards, you know, whatever we want to do next with our lives, whether it's vacations or college funds, really anything. It's just helping us get to that next level because eventually we want to be at a level we're past that. Just we're paying all of our base expenses to. We're growing and we're really thriving.

[Dave Meyer]

That's awesome. A very noble goal. I'm sure a lot of people relate to this, that, yeah, real estate, great way to make money, but it is a means to an end. It's like, you know, money in itself doesn't buy happiness, but it can buy you flexibility, which is a great way to get happier, in my opinion. So I love that. But let's dig into this. This idea here of rebalancing your portfolio, because this is super important stuff right now. You have this great portfolio. You said you, like, hadn't been really looking at the numbers. What were you doing? Just kind of like acquiring great assets and not really thinking about efficiency or, like, what did you need to change?

[Taylor Wing]

I was so focused on acquisitions, I would never pass up on a deal. So I was buying properties as fast as I could, get as many houses under my belt as I possibly could. I mean, I would do it like a general cash flow, but once you've been operating a property for at least a year, you can really look back at your expenses and how much you've been spending on the property versus how much income is generating and kind of just really look down your pro formas and make those decisions. So it's just something I didn't slow down before and really look at to optimize. And then once I slowed everything down and I was able to just look at the numbers and go, okay, it makes more sense. We have a ton of equity here. Why not move it into maybe some properties that'll perform a little better for us and help us make more cash flow?

[Dave Meyer]

Can I ask how you logistically did that? Do you have spreadsheets or what was the actual process like for doing this? Because I think a lot of investors find themselves in a similar situation that you were in, where it's like, you buy the deal, you see the cash on cash return that you're projecting, but then they don't actually go back and say, like, am I actually hitting that return? Or like, even if I'm hitting that return, is it as good as all the other deals that I'm buying or all the other deals I could go get on the open market today? Like, what were the actual tools you used to pull this off?

[Taylor Wing]

For one, we always had QuickBooks, but I'd never really looked at it. But what we did was we actually took some classes in QuickBooks to really learn how to use the programming. And we also hired a great CPA and a great accountant. That changed the game for me because before I was just paying tax bills and I had no idea why it was that number or how we got there. But now I found somebody that we have strategy calls and we try to project what our tax liability is going to be and we get ahead of it. So then we start game planning. So when it comes tax season, we're ready for it. So CPA changed my life. You know, a good accountant that sat with us and helped us clean up our books and helped us be able to pull the reports we need per property to really look at and see, okay, which ones are working for us, which ones are not performing as well. So I think those guys are really important to help you go get to that next level. I don't think you need to invest a ton of money maybe up front because you're just getting your first couple properties. But once you have a sizable portfolio, those guys are going to save you so much money and they're going to help you make those executive decisions.

[Dave Meyer]

Absolutely. That's a great way to do it. I think this is probably one of the most underrated things that investors should be doing. I try and do this personally quarterly. I just take, you know, not sometimes I'm not that good about it, but at least annually, I should say I try to do it quarterly, but just update what's going on in your portfolio. And I built this spreadsheet. It's actually part of my book. If anyone has read Start with Strategy, you will be a to download this, or maybe you've seen this, but I created a spreadsheet that after you get that information, either from your accountant or if you do it yourself, a way to just sort of side by side look at Every property that you have, and I personally like to look at it as a bunch of different levels, you know, your equity that you got in it, cash on cash return is of course, important cash flow. I like to do two things that I think are super important that a lot of people miss is one is risk. Like, how risky is this property? Because I want to see. Are all my properties super risky? That's a problem. Are all my properties super low risk? That's also a problem because I probably missing out on some upside. And the last one I do is how much time each property takes me because there's always a pain in the butt property. And when you look at these things side by side, you're like, oh, that pain in the butt property is actually making me the least amount of money. Like, why don't I sell this thing? This thing sucks. Or you're like, oh, this one is just amazing. I'm always going to hold on to that. So I really, whatever tool you use, recommend people do this for yourself. So, Taylor, when you started doing this, what jumped out to you? What did you learn?

[Taylor Wing]

Yeah, what I learned. Like you said, those. There's some properties that are just a thorn in your side that are just, like, taking way too much time and attention away from you and costing away too much money. I had a property, it was a cheaper one, one of the ones I first bought. The problem with it was just not a good neighborhood. And just problem after problem, it was just like, get somebody in there, they destroy it, turning it over. That's 15 grand again. Oh, we got squatters, kept breaking in. I gave the property plenty of chances to like, because it was one of the first ones I bought to make it work. But after like two or three iterations of this and going through maybe two or three different management companies, I love.

[Dave Meyer]

The idea of, like, giving the property a chance. Like, it's the property, but it is kind of true. It's like some. Some properties just, they. They struggle and you just got to get rid of them. And that's okay.

[Taylor Wing]

Yeah, it takes someone with maybe a more peculiar set of skills than I had or maybe that was able to deal with a lot more stress than I was able to deal with. So, yeah, to me, it wasn't worth it. That's one of the ones I liquidated and just move that money somewhere else. Is. Wasn't worth the headache for me because I, you know, I have a whole, you know, thing I got going on with my life, and I didn't want to just be a property Manager.

[Dave Meyer]

So was that hard? Because there is this narrative in the real estate investing community. It's like, never sell, you know, like, I just buy and just never sell. Was it hard to sort of shift your mindset?

[Taylor Wing]

I used to be like that. Maybe like, you're taking a step back, right? Like, oh, like I, you know, worked so hard to get this property and now, you know, I'm selling it and you're paying, you know, an agent probably you're paying closing costs. It kind of sucks. But after you see how much heartache you went through and you look over, like, your statements and you see, like, how much money that you've sunk into this thing, just rip the band aid off, man. Yeah, I totally agree.

[Dave Meyer]

I think it's. Yeah, it's. It's a hard thing because it's a new skill set to learn, you know, like you were mentioning you were sort of just in acquisition mode. That's a skill that usually, and I think rightfully people learn first. That's kind of what you need to do. But portfolio management, totally different skill. And learning how to optimize your resources, optimize your time. That's where I think most investors get to. You get to that point, but you do. It is a little daunting to learn how to manage that. I would love to hear how you have gone about managing that and how you've transformed your portfolio. We have to take one more quick break, though. We'll be right back. Managing rentals shouldn't be stressful. That's why landlords love rent ready. You can get rent in your account in just two days, which means faster cash flow and less waiting. Do you need to message a tenant? Chat instantly in app with no more lost emails or texts. Plus you can schedule maintenance repairs with just a few taps, which means no more phone tag. Are you ready to simplify Your Rentals? Get 6 months of rent ready for just $1 using promo code BP2025. Sign up using the link in the bio because the best landlords are using Rent ready.

[C]

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[Dave Meyer]

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[Dave Meyer]

Does it ever feel like you're a marketing professional just speaking into the void? Well, with LinkedIn ads, you can know you're reaching the right decision makers. You can even target buyers by job title, industry, company seniority skills. Wait, did I say job title yet? Get started today and see how you can avoid the void and reach the right buyers with LinkedIn ads. We'll even give you a $100 credit on your next campaign. Get started at LinkedIn.com results, terms and conditions apply. Welcome back to the BiggerPockets podcast here with investor Taylor Wang. Before the break, we were talking about how Taylor had started to transform his portfolio portfolio. So, Taylor, you did this analysis. Great work figuring out properties that were working for you, weren't working for you. How did you go about repositioning your resources and assets into new properties?

[Taylor Wing]

First of all, it took a lot of retooling for me. Like you said, it's completely different skill set for me and my personality. I much would much rather be on the acquisition side or on the sales side. Chit chatting with people out in the field, talking to contractors, making things happen. That's just. That's the kind of guy I am. So sitting behind a computer and having to crunch numbers and look at reports and it's just not as fun for me.

[Dave Meyer]

What? I love that stuff.

[Taylor Wing]

Yeah, yeah, I'M not a very analytical person. So it took a little bit of retooling. But what really forced me to do that is because we were looking at how much rents we're pulling in versus the debt service. And you know, we're like, why aren't our numbers better than we should be making a lot more money than what we are? Like, where, where's this money actually going? That's what forced us to really look into this and make those decisions.

[Dave Meyer]

And when you did that, so like, let's just say you pick a property not performing, did you automatically sell all of them? Did you consider refinancing any of them? Or how do you think about that?

[Taylor Wing]

Yeah, we had a couple options like you said. You know, maybe it's like, oh, should we switch, maybe try a short term or a midterm or should we do a cash out refinance, roll that equity and some other properties. But really, for me, once I figured out how to do a 1031 exchange, that's what really made the most sense because I was able to get that kind of maybe headache property off of my plate and I was able to move that money into properties that will actually kind of get us towards that financial freedom number that we're chasing. So for me, a 1031 made total sense. I was able to defer the capital gains on that. So it's a powerful tool. I love the 1031. If anyone hasn't done one yet, definitely look into it. It's not super expensive. I can't remember how much it cost me. Maybe like a thousand or two thousand, something like that. And was able to save maybe close to six figures in taxes alone.

[Dave Meyer]

Yeah, it's 20% of the equity that you built up.

[Taylor Wing]

So crazy a lot. So it's, it's, it's a powerful tool and definitely need to use it.

[Dave Meyer]

Yeah, absolutely. And if you're not familiar what a 1031 is, it's a part of the tax code that allows specifically real estate investors. This is a really unique part about being a real estate investor. If you buy a property, it builds up all this equity. That's great. But when you go to sell, if you wanted to trade out like Taylor's talking about, without this rule, you pay 20% capital gains on your profit. So if you bought it for, I'll use very simple numbers. You bought it for 200, sell it for 300, you have $100,000 in profit there, you'd pay 20 grand in taxes, which again, you know, that's. You made 100 grand. So that's good. But ideally you want to take that 100 grand and reinvest it into another proper allows you to keep scaling and the 1031 exchange allows you to make a tax free exchange into a, what they call a like for like property. So you take an investment property, you buy another one. There are some time limitations that make it a little bit stressful, at least in my experience, doing it a few times, but it could be very, very worth it. So if you are in this portfolio management stage of your investing career, checking out a 1031 and using it can be a really, really powerful option. So Taylor, when you went about selling these properties, were you going to reinvest in the markets they were in? Because you're now across three markets, right? You're in North Carolina, in South Dakota, you're in South Florida. Did you just reinvest in the same market or did you want to bring everything to Florida to sort of consolidate?

[Taylor Wing]

I actually the opposite. I had properties in Florida and I moved that money out of the state back to Sioux Falls and, and Fayetteville. And the reason being is what was really prices that were creeping up was my insurance costs. My properties were cash flowing initially and then within the rise of insurance costs, which is a problem in our state. And it needs to be addressed. It just basically breaking even or even at a slight loss. So it didn't really make sense for me to hold them anymore.

[Dave Meyer]

Okay. And that's kind of what I was curious about because you bought a lot of your properties in the early 2000 and 20s and it was easier frankly to find a lot of deals.

[Taylor Wing]

It was.

[Dave Meyer]

So I'm curious, was it how relatively hard or easy was it to find cash flowing deals in the other two markets you operate in?

[Taylor Wing]

Much easier. I mean, because, you know, the Midwest and the Southeast, it's a lot easier to find cash flow. Just prices of real estate are just not as high as you would see down here in South Florida. Florida's been appreciating like crazy, especially after Covid. It's, our market's cooled down quite a bit, but we're probably going to be competitive with California soon. I don't know, we'll see.

[Dave Meyer]

But I, I, I actually made a whole episode of on the Market, our sister podcast about Florida and what's happened there the last couple of years. From like 2020 to 2023, I think prices went up 50%, which is just absolutely insane. Like normally that would probably take two decades in a normal situation. And nationally it went up like 40%, but it was 53%. So yeah, Florida has been, I think up until 2024 the fastest growing state for those three years since then. It's now largely in a correction, but you know, it's been a roller coaster ride but a lot of amazing appreciation. So when you went to these other markets though, is it like on market kind of, you know, stabilized deals that you could buy cash flow or were you fixing them up? Finding off market, how do you go about it?

[Taylor Wing]

I've purchased most of our portfolio off market, either direct to seller or utilizing Connections wholesalers to acquire deals. There's been a couple deals I've bought on market, but it's pretty rare. There's just so much more competition. Our primary house though is a really creative deal. How I bought the house I'm living in now. And that was actually an on market deal. And that's the same, that's a cool seller finance deal that we negotiated. But for the most part, most of our deals that are in our rental portfolio have been off market.

[Dave Meyer]

Okay, cool. And was it hard to build up that deal flow or did you have it already from operating there?

[Taylor Wing]

Yeah, basically by the time we moved down here, we already had our teams, our systems, connections, all set up in the markets that we were previously operating in. So it's easier for me to plug back in. Even to this day, that's where I'm still hunting for deals primarily is in those two markets. And so when I find something, when somebody sends me a deal, I'm able to execute on it.

[Dave Meyer]

How would you describe the profile of your deal today? Maybe just walk us through a recent one. What are you buying it for, how much work are you doing for it and what does the cash flow come out to be?

[Taylor Wing]

I bought two deals in Fable last year. They're very similar deals and prices have increased in that market as well. So these two deals I did, they're both brrrr deals. They were both sourced from connections and wholesalers. And basically I've been buying them probably like in the 140s range.

[Dave Meyer]

Okay.

[Taylor Wing]

Maybe in the 130s if I'm lucky. And on the back end, I'm probably getting them appraised for like the 220 to 240 range.

[Dave Meyer]

Nice.

[Taylor Wing]

So I don't, I don't really do huge rehabs. I like to do cosmetic in and out within a couple months. That's kind of how I've done with those last two that I bought. And cash flow is probably like 300 bucks maybe if you're lucky.

[Dave Meyer]

400, that's pretty good though. Like, so what does that come out to on a cash on cash return? So 400 bucks a month, that's 4ish grand a year in cash flow per property.

[Taylor Wing]

Yeah. And you know, maybe 300 bucks isn't life changing, but you know, you stack those dominoes up and once you build up a portfolio and you set those units on autopilot with a property management company, I feel like your lifestyle and your, your flexibility really starts to change. And you can feel that.

[Dave Meyer]

Oh absolutely. And the other thing that I think a lot of people miss out on is that $300 a month is usually tax free if you're doing it right tax wise. So like that's the equivalent of making $400 a month or even 450 depending on your tax bracket. So it's just another thing to remember is that a lot of times rental income can almost be treated as post tax income, which is incredible. So you gotta make sure you think of it that way.

[Taylor Wing]

Yeah, rental income is the best income. So yeah.

[Dave Meyer]

So if you're buying at 140, how much, how much cash are you putting into each of these deals? Total?

[Taylor Wing]

Usually on the back end I'll do a cash out refi and on these ones I'm not able to pull all of my money back out. But usually my goal is if I can leave like ten grand or less in there, I'm happy from the front end because usually I'll do 100% financing on the front end. So on the back end I might have to bring maybe 10k to close.

[Dave Meyer]

Okay, so you have a total of 10k into this deal and you're making 4k a year off of that?

[Taylor Wing]

Yes sir.

[Dave Meyer]

So that's just a casual 40% cash on cash. That's insane.

[Taylor Wing]

That's why I like to do the brrr method and buy low and put in that sweat equity. Fixing up the property because you're just cash on cash return is going to be so much greater.

[Dave Meyer]

I think this goes to say one, a lot of people say our cash flow are dead. Clearly not a lot of people right now say the BRRRR doesn't work anymore. So what is your message to those folks?

[Taylor Wing]

I think it's a lot harder nowadays, which is why I don't buy one a month anymore. But they're out there. You just have to be patient and you got to wait for those deals. But there's those diamonds in the rough out there still. You just, you gotta find them.

[Dave Meyer]

So how Are you finding them now? Still off market, but like, it slowed down from one a month. What is your cadence right now?

[Taylor Wing]

Yeah, so last year I only did two in Fayetteville.

[Dave Meyer]

Okay.

[Taylor Wing]

If you're able to even buy, in my opinion, even one a year, you're making that forward momentum still. It's. It's still awesome. So, you know, again, I don't even care about doors or anything like that. And I don't compare my portfolio to anybody else's. It's not a competition. It's just all about cash flow and the lifestyle that it's going to create for you.

[Dave Meyer]

100%. I couldn't agree more with the philosophy. Door count is very silly. You know, there are people I know with amazing door counts and terrible cash on cash. And then there's the opposite, right? There's people with six, five, six paid off properties that are crushing.

[Taylor Wing]

That's all you need.

[Dave Meyer]

It's. Right. Yeah. It's like totally different. I been thinking a lot more about just starting to pay off properties at this point, in my opinion, not just being in total acquisition mode. It's great. It's like really comforting for some reason.

[Taylor Wing]

It is.

[Dave Meyer]

This has been great, Taylor. Thank you so much for sharing all this with us. Do you have any, you know, last advice for. For folks listening to this before we go again?

[Taylor Wing]

You know, a lot of those other metrics don't matter as much. It's all about lifestyle. And real estate is a powerful tool. Use it to create the lifestyle that you want, hand it off to a property management company and enjoy the money. You know, it just, it's meant. Life's meant to be enjoyed. Spend it with your family, spend it with your loved ones. And think of real estate as just a powerful tool to help you get there.

[Dave Meyer]

Well, thank you so much for joining us, Taylor. Really appreciate you joining us again on the BiggerPockets podcast.

[Taylor Wing]

Thank you, Dave. Thanks for having me. Everyone out there, thank you for listening.

[Dave Meyer]

Yeah, we'll have to have you back again a third time, Taylor. Keep it up. It'll be fun to track your progress.

[Taylor Wing]

Let me know.

[Dave Meyer]

Thank you so much for listening to this episode of the BiggerPockets podcast. I'm Dave Meyer. See you in a couple of days. Thank you all for listening to the BiggerPockets Real Estate Podcast. Make sure you get all our new episodes by subscribing on YouTube, Apple, Spotify, or any other podcast platform. Our new episodes come out Monday, Wednesday and Friday. I'm the host and executive producer of the show, Dave Meyer. The show is produced by Ian K. Copywriting is by Calico, Content and editing is by Exodus Media. If you'd like to learn more about real estate investing or to sign up for our free newsletter, please visit WWW dot. The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose, and remember, past performance is not indicative of future results. BiggerPockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising from a reliance on information presented in this podcast.