Why This Investor Gave Up Residential Real Estate
(And What He Did Instead)
What does it take to go from knocking on doors… to owning a $50 million commercial real estate portfolio?
In this episode, I sit down with Jess Read—an agent-turned-investor who walked away from chasing commissions to build true financial freedom through commercial real estate. We talk about:
✅ How he house-hacked his way into investing
✅ The moment he realized financial freedom wasn’t that far off
✅ The worst real estate partnership of his life (his partner moved to AFRICA)
✅ Why most residential agents never build wealth—and how you can
✅ How Jess and his partner underwrite cash flow deals across the Southeast
✅ Advice for any agent thinking about making the leap into investing
Whether you're a high-producing agent or just getting started in real estate, this conversation will show you what’s possible—and what mistakes to avoid—when you stop selling and start owning.
Learn more about Jess: https://cashflowtofreedomacademy.com/
Get commercial real estate coaching, courses, and community to jumpstart your investment journey over at CRE Central: www.crecentral.com
Key Takeaways:
Start Investing Early: Residential agents should begin investing in real estate to build cash flow and financial freedom, rather than spending money on luxury items.
Cash Flow is King: Focus on creating passive income that can cover your expenses and provide options in life.
Partnership Matters: Choose partners carefully and do thorough due diligence. A bad partnership can disrupt your peace of mind and potentially cost you money.
Commercial Real Estate Advantages: Commercial properties often have less drama, more stable tenants, and require less day-to-day management compared to residential properties.
Patience in Investing: Don't rush to do deals just to do them. Wait for opportunities that truly make financial sense, especially in challenging market conditions.
Time Freedom is Valuable: Prioritize controlling your time over simply chasing money. Investments should provide you with more life options and flexibility.
Continuous Learning: Enjoy the process of investing, keep showing up, and understand that building wealth is a journey, not an overnight success
About Your Host:
Tyler Cauble, Founder & President of The Cauble Group, is a commercial real estate broker and investor based in East Nashville. He’s the best selling author of Open for Business: The Insider’s Guide to Leasing Commercial Real Estate and has focused his career on serving commercial real estate investors.
Episode Transcript:
Tyler Cauble 0:01
How do you go from knocking on doors in 2009 to building a nationwide commercial real estate portfolio and helping others achieve financial freedom along the way? In today's episode, I'm sitting down with Jess Reed, a former residential agent turned full time investor who's overseen over $50 million in real estate deals. We talk about the early hustle, the shift from residential to commercial, the power of cash flow and the painful lessons he's learned from the wrong partnership. If you're a residential agent thinking about investing or you're looking for real world insight into scaling the portfolio the right way, this one's for you. Let's get to it.
Tyler Cauble 0:42
So Jess you. You came to Nashville in 2009 you got started in door to door sales. Yup, that's not easy to do. What made you stick with it for so long? When, when so many others that get into door to door sales quit?
Speaker 1 0:56
I think, I mean, within my first couple of days out, knocking on doors, I got a couple of sales, and, you know, I think I was making 300 350 bucks per per deal. And so I just kind of quickly did the math in my head. I was like, wow, I made 350 bucks today, or I made 900 bucks today, and I worked for four hours. Like I recognize that some days I may do one, some days I may do zero, some days, I may do three, but I think I just realized, like, for me, it was worth again, sort of controlling my time and knowing, like, I would rather do that and take the gamble of having a day where I didn't make any but also having the potential of making 900 1200 bucks, versus going into an office where I knew I was only gonna make $20 an hour, and it was something I didn't want
Tyler Cauble 1:41
to do anyway, yeah, I got my started in Cutco, yeah, knives, man, yeah, it wasn't quite door to door, but it's the same principle, if you're having a cold call, yeah? And find, you know potential buyers every single day, right? You're only as good as your last sale, which I think is incredible training for investing in real estate, totally, because it's the exact same process, right? Yeah, absolutely. So, I mean, you've said that you loved sales because it gave you control over your time and your income, and how has that mindset really served you on the real estate
Speaker 1 2:10
side of things? I mean, I think moving from door to door sales into real estate. So in 2012 I got my real estate license. I was a residential broker, and it was just a higher ticket when I first got started, I just kind of saw it as a higher ticket item. It was like, Wow, if I can go find eight people that are looking to buy houses, and they're all going to spend $300,000 on a house. That's that's a great that's a great month or a week or whatever, right? And so again, I think I just saw it as a stepping stone into a new opportunity where I was essentially doing the same thing, which is sitting down, listening to people, listening to their concerns, listening to their needs, and then taking that information and helping them solve the problem as as quickly as I could. And I think, I think for me, in real estate when I was first getting started, that was something that I was pretty good at because I didn't have to go out and show sure there were some outliers. But I wasn't showing 20 houses to a buyer. I was very good at getting clear on what they were looking for. So most times I could, I could show them four or five houses, and one of them fit the bill, and it was a Quicker, quicker process with those, with those clients, and that just made me have more space to have more clients, but also have more more free time at the same time. So when did
Tyler Cauble 3:27
you make the switch from real estate agent to real estate investor and talk us through that first deal?
Speaker 1 3:35
So the first real deal was actually I bought a house for myself, and I had two roommates, and they were paying to live with me. They were friends of mine. We were having a good time. This was in 2014 and I was like, Wait a second, I've got this amazing house. It's in Wedgwood, Houston, and I'm not paying a dime. I went from renting a place that was, you know, 1200 1300 bucks a month, to now I have my own house, and I'm not even paying any of the bills. The mortgage is paid. The water's paid. Everything is paid. I was like, this is pretty cool. And so then I kind of started thinking about, how can I go get more properties that are that are cash flowing. So this whole idea of of building cash flow started to kind of seep into my thought process. And you know, originally, it was just, okay, cool. I've got my my primary home. It's paying my mortgage. How can I go out and get all my bills, my cell phone bills, 200 bucks, my insurance, 200 bucks. How can I go get another asset that's paying me for 600 bucks a month to take care of those expenses? So then it just becomes, it became sort of a process of just checking off those boxes of, how do I get all of my fixed expenses paid for with with real estate? So,
Tyler Cauble 4:46
so what did that look like? Did you go out and start buying more single family homes? Yeah. I mean, how
Speaker 1 4:51
did Yeah? So my, my first true investment property was down in Alabama. So I bought a property in. In near Muscle Shoals, and I think I paid like 60,000 bucks for it, and got a tenant in there. I think my mortgage was like 400 bucks a month, and tenant was paying 1200 bucks a month, you know. And I had a property manager, because I wasn't going to be going down there to keep tabs on the place. And so they got, you know, 10% of of the rent. And I was still left over with, you know, by the time taxes and everything were paid, I was making like, 400 bucks a month on that property. So, and, you know, you do the math on that, I think I put down maybe $10,000 so I'm making 4000 5000 bucks a year on $10,000 that's pretty good return, you know. So I bought a couple more properties in Alabama. I bought a few properties around here, but then I sort of started, I was, I was it was becoming a good bit of
Tyler Cauble 5:53
work. Is that what made you shift your focus into commercial like, how did you discover commercial real estate and what, what did you think was the opportunity
Speaker 1 6:00
so Ryan Stackhouse, my partner with cash flow to freedom, you know, he was a mortgage broker for almost 20 years, and we actually did deals together. So when I was an agent, he was a broker. We were doing deals. So occasionally we would get together have lunch and kind of talk shop, you know, we were, we were both buying investment properties, and he, he started getting into the commercial space a year or two before I did. And one of our last conversations, he was kind of painting the picture of how things were going for him in the commercial space. And it seemed from talking to him like it was a little less drama, a little less headache, you know, some of the variables that I was starting to feel he was removing from his plate. And I was like, that sounds pretty good. And so, you know, we ended up partnering together on a couple of commercial deals, just he and I, and we were sort of off and running from from there, you've
Tyler Cauble 6:51
built a personal portfolio and launched a coaching platform. I mean, you, you have gone and done so many different types of commercial deals. I mean, what were, what were some inflection points or bottlenecks that started to get in your way as you guys were scaling the portfolio you have today?
Speaker 1 7:09
I think inflection points, I mean, just realizing that financial freedom wasn't as far off as I thought it was. I think growing up and you hear about, you know, financial freedom, most people, they hear they're like, yeah, right, that's for that's for rich people. You know, you know, you gotta have millions and millions of dollars. But I mean, for me, you know, when I was getting started, I mean, my expenses were like four grand a month, so I was able to quickly, kind of knock that out. And you know, by definition, my cash flow was greater than my expenses. I was free right now. I wasn't gonna be going and buying Gulf streams and yachts and things like that. But I had control of my time at that point, because my income wasn't dictated by me going and showing up and selling another house to make another paycheck, right? And so I think that process of just recognizing that financial freedom wasn't that far off was a huge inflection point. And then I think for me, bottlenecks were just, you know, some of the day to day operations of owning commercial properties, right? I mean, we've got stuff in Texas, Florida, Indiana, all over the southeast, a couple outliers. And, you know, when some of those issues pop up, you know, we're we're not there. And so I think for us, it was finding really good, you know, partners, in a sense, that can go out and handle some of those variables in those different locations so that we weren't having to scramble trying to figure out, well, who's who's going to get on a plane and go to Odessa, Texas, and Figure Figure out what needs to be solved here. Yeah, Ryan's not too far. Ryan's not too hard to vote, though. Yeah. And back in the day, when he was traveling all over the country and his his RV, he would kind of pop in on all the properties and kind of check in. And he still does that some, but, but, but again, for us, you know, the triple net, absolute net lease space, you know. And again, that was a mindset shift, right? Coming from residential where, you know, I'm thinking, are these, are these renters going to trash my place completely? Like, what am I getting into? I started Airbnb in one of my properties, and I didn't know what I was going to, you know, come Monday morning, when they checked out, I didn't know what I was going to see when I walked in, right? And so that idea of, like, are these people going to take care of my place? You transition into commercial, and it's like, these are businesses. They have customers coming in here on a daily basis. They have their own capital invested in these properties. In most cases, they have no interest in trashing the place, right? So it was, it was kind of a mental shift. There it was. It was definitely the right, the right play for us. I think just having, you know, more more time, freedom and just less stress, I think, is the big, the big kicker,
Tyler Cauble 9:32
yeah, finding the right partners is incredibly important. I mean, that's a critical step. So commercial real estate is very much a team sport. No man is an island, yeah, when it when it comes to this industry, and y'all are investing all over the country, you know, maybe not California, maybe not New York, but they're spread out. What does the day to day Asset Management look like on your side, it's
Speaker 1 9:53
pretty low key, honestly. I mean, you know, again, because all of our stuff is long term tension these. Are 1015, year leases. You know, majority of these tenants, I mean, they've been in these properties for 1020, 30, even 40 years. Some of, some of these properties. So again, like, there's no worry about, well, what are they doing? Are they? They taking care of the place? Are they? Are they taking care of deferred maintenance, all these things, like, they have taken phenomenal care of these properties. And so, you know, there is check ins, right? I mean, there's, there's yearly, maybe semi annual, check ins on the properties. But we don't have property management at these properties, because, again, for all the reasons that that that I just explained, but you know, we have kind of quarterly updates on the properties, and we check in with the owners here. And there's anything that you need, you know, every now and again, we'll have, you know, a leaky metal roof or something that we have to get taken care of. But it's, it's minor stuff, you know, we, we, fortunately, don't have any massive headaches that we have to deal with very often. Obviously, stuff happens, for sure, but it's, it's few and far between. So
Tyler Cauble 10:54
when you all started bringing in investors, I mean, what was the biggest challenge on that front like, how are you handling the pitch? How are you gaining trust? Because having investors on board is crucial if you want to scale this Sure, and syndication makes that significantly
Speaker 1 11:10
easier. Yeah, I think when we started again, Ryan and I were doing deals, he and I together, and we got to a place where all of our funds were exhausted, and so we said to ourselves, well, our options are we can either go make more money, save more money to invest, and that timeline wasn't fast enough, and so we said, we have to start using other people's money. And so when we started having those conversations, honestly, it was, it was not as difficult of a swing as I thought, because I think we were talking to people that were doing all the things that we've been told our whole lives, right? Go, go, max out the 401, K go. Do all these things so that when you get to this golden age and you retire, like you'll have something there to do. And I think most people are kind of starting to wake up to this idea of, like, how do I build cash flow that I can utilize now? Like, I don't want to wait until I'm 70 years old. I want to build cash flow that can fund life now. And that was just that was sort of the pitch, so to speak. It was really more obviously, the deal points, what they could expect from a yearly rate of return. How long is their capital going to be tied up all that stuff, of course, but more importantly, like, what's the cash flow going to do to hey, you're going to be making $650 a month on this deal. How does that help provide some breathing room for you in your in your life? Yeah, yeah. I mean,
Tyler Cauble 12:25
with that being said, your your approach is heavier on the cash flow side, not so heavy on the appreciation side. That doesn't mean that you're not going to get the appreciation. That's not your focus when you're buying these assets. Interest rates are higher today, yep. How do you How are you all approaching deals and making them work?
Speaker 1 12:39
It's been tough. I mean, you know this this past year has been slow. We're just, we're honestly just now getting to a place where we're starting to see some deals that pencil out. We've got a deal locked up now. We've got another loi out now as well that we're waiting to hear back for. But last year, I think, we closed the deal in January of 24 we didn't do another deal because it just didn't make any sense. I mean, the interest rates were, and still are, you know, high, and we've got to be, you know, nine at a minimum, really, nine and a quarter cap for for it to make sense again, when you're when you're syndicating, you've got investors to pay preferred rate of returns. To pay, you've got to have even more meat on the bone. And obviously, you know, Ron and I want to make something on the back end. And you know, we would be looking at deals, and it's like, cool, like, it's, it's going to be a $1.8 million raise, and we're going to make $620 a month. We're like, pass. And we'd rather, we would rather just wait and, you know, kind of stockpile cash. And when I say that, I just mean, you know, we've got investors that have verbally said, Hey, I'm ready to go when you guys have something. So we've got, in the process of waiting, really, over 12 months for a new deal. We've got tons of investors that are kind of sitting there ready to rock and roll, but it's been, it's been a challenge to make deals work with the rates where they are. I
Tyler Cauble 14:00
think that's a prudent investment decision, though, right? I mean, I didn't buy. I mean, the last deal that we bought was peerless mail, yes, you're a partner with me on right? And then I bought a self storage facility in December, yeah, up in Madison. And there, that's two years, yeah, between deals. But just like you, you look at it, you're like, I'm not going to get out of bed and take the risk for $620 a month. I mean, today, right, right? Just 15 years ago,
Speaker 1 14:25
whatever, totally, but it's just not worth it. I mean, again, for Ron and I, both, we are very much aligned a lot in the way that we think and and peace of mind and just peace of mind in our day to day lives and how we how we live, is is huge, and it's just not worth it to do a deal, just to do a deal, right? If it's not gonna, if it doesn't really make sense, or if there's some some some variables that we just aren't comfortable with, we're not going to do the deal. We would rather just wait for a better deal to come along than to make a deal happen.
Tyler Cauble 14:57
Well, you don't get to the point in real. State investing, right where you have a portfolio like this, you have the passive income, you get the lifestyle that you want, without getting a couple battle scars along the way. 100% what was the biggest mistake that you made in growing to this point? And what did you take away
Speaker 1 15:13
from that? I think my biggest mistake has been I had a bad partner on a deal, not obviously Ryan, my partner on syndications and with cash flow to freedom, but I had a partner on a mobile home park in Texas who, once we closed on, I funded the deal, and the deal was going to be that he was going to manage the place. And obviously, with a mobile home park there's lots of variables that somebody needs to be on the ground, taking care of stuff, right? And that was going to be the deal. And we closed on the deal. And less than two months later, he moves to Africa, which he knew about, but didn't tell me about, like in in the process, obviously, I would never have done the deal had I known you were going to move continents, right? Because you can't manage any property, much less a mobile home park in Texas from Africa, and so that just opened the doors to two years, I think of just a nightmare. And when I say that, you know, I didn't, I didn't lose a ton of money on that deal, but it totally disrupted my peace of mind, and which I've already said is incredibly important to me, and it just totally hijacked my, my peace of mind for, like, for like, two years, and we have been able to sell that property I've got, I got almost all of my principal back, not quite all of it, you know. And, oh, by the way, wasn't making money on my money for that whole time. So that was a loss, right? But I was able to recoup a hefty chunk of the principal, which, which was great, but again, more importantly, that two years was just, it was terrible. Dude just dealing with that. So your
Tyler Cauble 16:52
operating partner moves to Africa, thinking he's gonna operate from I mean, what was, what was going through his mind? What was his like? What was his thought process on this?
Speaker 1 17:01
I wish I could, I wish I could tell you I really don't know, because and these that was, like, my response, right? Like, what are you thinking? Like, how do you think this is going to play out, right? And multiple, you know, I'm sorry. I'm gonna fix it so you get it right. There were so many, so many, like, checkpoints where I kind of started thinking, okay, cool, we're gonna get this back on track, because it had the potential to make great money. I mean, the first maybe four or five months, even after he left, the current tenants were still there. Everything was okay. I mean, I was making like, 22% on my money, right? So cool. But that, again, that quickly went away. And, yeah, it was just kind of broken promise after broken promise. And I just, you know, I can't, I don't handle that well with dealing with adults, right? That, that say they're going to do something, they just don't do it. I don't know that's, that's, it was rough. That's fucking nuts. Yeah, it was crazy. When you get
Tyler Cauble 17:57
into a partnership, delegating roles, yeah, incredibly important, right? It sounds like it was pretty clear, I'm funding it, you're operating it, yep, but that's every real estate investors worst nightmare when it comes to a partnership is my partner is not going to uphold their end of the bargain. They're not going to carry their weight, yeah. How? How have you approached that? Since Do you Do you have clauses in your operating agreements? Are you just stricter on who you actually jump into a deal with. How does that process look now,
Speaker 1 18:24
that partnership came about from from word of mouth, from somebody that that I trusted, and it just wasn't enough due diligence. That person is still, you know, somebody that I trust very much, and quite frankly, it was something that he didn't even see, and that same partner of mine had some shady dealings with, with the person that referred him to me. So we were, but we were both kind of, at one point comparing notes. My situation was a bit more severe. So I don't, you know, there was no, there was no blame to him for making the introduction, but you know, that was really all that I went on and so, you know, I think I learned, hey, even when it's somebody that you know, like and trust that's referring you to somebody do your own due diligence and really make sure. Because you know, people can hide stuff, right? I mean, people can put on a game face and say all the right things, but then turn it off and become a totally different person, or just not uphold what they said they were going to do. And so, to answer your question, I mean, I'm super careful, and I really don't, you know, Ryan, I've been partners for a handful of years. You know, there's very few things that that I'm really like, looking to partner on with, with other people at this point. Honestly,
Tyler Cauble 19:35
yeah, I realized, like, when I was first getting started in my career, I was, like, willing to partner with just about anybody that I felt like was a good person and like you. Now my circle is so tight, people reach out to me about wanting to partner on deals or, Oh, I'll go bird dog a deal for you. And it's really tough,
Speaker 1 19:53
yeah. I mean, you do the risk reward on it. It's like, Yeah, I think I'm good, you know? I mean, and early on to your point, like you're trying to make those. Connections, because there's, there's gaps in your own levels of experience, and so it makes sense to have those partnerships sometimes. But when you get to a place where you've got something to lose, maybe even, like, when you're just getting started, you got nothing to lose, like, Let's go make something happen. But listen, I've got a wife, I've got kids, like, I've I've got things of incredible value to me that I'm just not willing to take on certain things, and I'm totally fine with that.
Tyler Cauble 20:26
Yeah, you know, it's, it's funny how much of an advantage that is when you're younger, to not have any of that. Sure be willing to jump off that cliff, yeah, but it's also pretty nice to be at this point where you don't have to jump off the cliff totally 100% what advice would you give to another residential agent that is listening to the podcast and relating to a lot of your story that's considering jumping in and
Speaker 1 20:49
investing? Begin? I would say begin. Because I think, you know, there's, there's so many agents out there that are crushing it. They're making tons of money, but they're not investing any of it. I see it all the time. I see it all the time. I see people getting into real estate, and they're coming from from bartending jobs or jobs where they were making 30 35,000 a year. And then their first year as an agent, they make $140,000 and they go out and buy a Land Rover. I'm like, What are you doing? Go buy a rental property. Go build cash flow so that you can get to a place where, listen, if you love what you do, great, keep doing what you do, but build cash flow so that you can have some options. So that if you want to take your kids to Europe for the summer, you want to do some of these things, you have the option to do that. This isn't all about like, hey, you need to build cash flow because you hate your job and you want to get out of there as quick as possible. I know plenty of people that build a lot of cash flow that love what they do, but the cash flow just gives them options for if they want to take a break, or if one day they want to let off the gas a little bit. They haven't become so accustomed to the lifestyle that's come from the activity level of selling houses, all that, all that activity, and they can then kind of make some different decisions. And
Tyler Cauble 22:04
it never hurts to have a safety net as well that pays you absolutely something, you know happens, right? You've got the the cash flow coming in, yeah, pay for
Speaker 1 22:13
it. I mean, we saw, you know, when the market shifted here a little bit a couple years ago, right? I mean, and when rates, when rates jumped up. I mean, the market changes. Like I talked to agents and mortgage brokers that weren't having deals coming in. It's like if that was the sole source of income, and they go from 40 grand a month to almost nothing, and they've got nothing in place to safeguard that's a that's a scary situation.
Tyler Cauble 22:38
Looking back on your journey now, starting off your career, door knocking, and now you've overseen over $50 million worth of real estate deals. What's one lesson that you wish you could take back to yourself in 2009
Speaker 1 22:50
one lesson, I would say, is just enjoy the process. I think for me, when I was first starting out, I wanted everything to happen so quickly, and I wanted it all like now. And I think I was, I was, I was chasing the the money more than I was what I was actually going to do with with the money. And I realized, you know, as I got started, like the money is only one piece of it, right? It's really, for me, the time component, because I'll take the time over the money. 10 out of 10 times you're either you either have control of your time or you don't, right? There's really no gray area there. The money just dictates how you're able to spend your time. And I think, I think for me, I would have just told myself, like, listen, it's a process. It's a journey. You're going to get there. Just keep showing up every single day. You don't have to have it all right now. Just enjoy the process. Enjoy your friendships, enjoy the process of just learning what you're learning and and keep showing up, and everything's gonna work out for itself.
Tyler Cauble 23:53
What's next for Jess Reid? Well, I've
Speaker 1 23:56
got a baby coming in at the end of August, another girl, and thank you. And so listen, becoming a dad totally just changed my life. I mean, my daughter, Frankie, will be four next month, and it just totally changed the lens in which I see everything, and just how I prioritize my time and my focus and in the best way possible. And so the idea of having another girl and being able to kind of go through all those firsts again is going to be a ton of fun. So So that's next. And then obviously lots of real estate deals. You know, Ron and I are still doing our cash flow to freedom, still doing some coaching, and so still still rocking and rolling on that front too. So awesome. Just
Tyler Cauble 24:40
if anybody wants to reach out they want to learn more about cash flow to freedom, where can they find you? The
Speaker 1 24:45
Jess, read at Instagram is really the main point of contact at this point, we've got cash flow to freedom.co as well, where they can learn about courses and live events, stuff like that.
Tyler Cauble 24:55
Awesome. Thanks. Man, yeah. Man, wow.
What does it take to go from knocking on doors… to owning a $50 million commercial real estate portfolio? In this episode, I sit down with Jess Read—an agent-turned-investor who walked away from chasing commissions to build true financial freedom through commercial real estate.
Whether you're a high-producing agent or just getting started in real estate, this conversation will show you what’s possible—and what mistakes to avoid—when you stop selling and start owning.