In short
Real Estate Rookie Podcast Episode Notes
Episode Title
Buying 4 Small Multifamily Rentals in Just 2 Years (While Working a W2)
Hosts
Ashley Kehr and Tony J Robinson
Guest
Derek Brickley
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Overview In this episode, Derek Brickley shares his journey from a traditional nine-to-five job to becoming a successful real estate investor who has acquired four small multifamily properties in just two years. Derek discusses the fears and uncertainties that held him back initially, his first deal, and how he leveraged his W2 income to support his real estate ventures.
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Key Themes and Discussions
- Overcoming Analysis Paralysis
- Initial Hesitations: Derek's journey began with the fear of taking the first step in real estate investing, which is a common barrier for many rookies.
- Realization: He recognized that his “safe” nine-to-five job also had its uncertainties, prompting him to act.
- The Importance of Networking
- Building a Support System: Derek emphasizes leveraging an investing network to bridge knowledge gaps and gain confidence.
- Community Involvement: Joining platforms like BiggerPockets and attending local real estate meetups helped him connect with other investors.
- The House Hacking Strategy
- Defining House Hacking: Derek utilized house hacking, where he lived in one unit of a multifamily property while renting out the others, effectively reducing his living expenses.
- Selecting the Right Property: He set clear criteria for what he wanted to purchase, focusing on cash flow and market fundamentals.
- Learning Through Action
- First Deal Lessons: Derek's first deal taught him crucial skills, such as making offers, planning renovations, and tenant management.
- Critical Mistakes: He cautioned against common pitfalls in DIY renovations and highlighted the importance of understanding what to expect during property management.
- Transitioning from Employee to Investor
- W2 as a Support: Rather than quitting his job, Derek used his W2 income to finance his investments, creating a safety net.
- Impact of the First Deal: His initial investment provided not just cash flow, but also the confidence to pursue further investments.
- Managing Expectations and Reality
- Challenges During Renovations: Derek faced unexpected complications during renovations, which extended the timeline significantly.
- Importance of Clear Planning: He stresses the need for clarity in renovation plans and knowing who to rely on for help.
- Future Growth and Exit Strategy
- Continuous Learning: Derek's first deal opened the door to further investments, emphasizing that growth comes from learning and applying new lessons.
- Exit Timeline: He views his job as a tool rather than a limitation, allowing him to enjoy the process of real estate investing without the pressure to quit.
- Building Systems for Success
- Systematization and Delegation: Derek discusses the significance of creating systems and delegating tasks to manage multiple properties effectively.
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Key Takeaways
- Start Small: Don’t wait for complete confidence or clarity; take the first step with a manageable deal.
- Leverage Your Network: Surround yourself with knowledgeable people and resources to boost your confidence.
- Expect the Unexpected: Be prepared for challenges, especially during renovations, and have a plan for managing them.
- Use Your W2 Income Wisely: Your job can support your investing journey rather than hinder it.
- Confidence is Key: The first deal is about building confidence and experience that can propel future investments.
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Resources Mentioned
- BiggerPockets: A community and resource hub for real estate investors.
- Books: Suggested reading includes "The Book on Flipping Houses" by Jay Scott for further insight on renovations and deal management.
- Networking Events: Local meetups and larger investor conferences to connect with like-minded individuals.
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Conclusion Derek Brickley's story illustrates that real estate investing is accessible even while maintaining a full-time job. His journey emphasizes the importance of taking action, building a network, and continuously learning from experiences to achieve financial freedom through real estate.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VODerek's Journey to Real Estate
0:48 to 2:12
Derek Brickley shares his initial struggles and the turning point to real estate investing.
“Derek, thanks so much for joining us today.”
Shifting Mindsets from Security to Opportunity
2:12 to 3:20
Discussion on the perceived security of a W-2 job vs. the potential of real estate.
“stuck in this day-to-day and that it wasn't closely achievable to be able to leave your nine-to-five?”
The Confidence to Take Action
3:20 to 5:00
Derek emphasizes the importance of taking the first step in real estate investing.
“And one of the things that we highlighted was what you just said is that a lot of people have this concept that a day job is the most secure thing that you can have in your life.”
Building a Supportive Network
5:00 to 7:20
The value of having a network of support and resources for new investors.
“you from getting where you're actually trying to go in the first place.”
Setting Clear Investment Criteria
7:20 to 9:20
Derek explains how defining criteria helped him find suitable deals.
“I don't have rich uncles or all these people that are doing this.”
Analyzing Market Risk vs. Reward
9:20 to 13:24
Derek discusses evaluating risk and market conditions before investing.
“You started educating yourself and you finally decided to act.”
Challenges of a First Property Rehab
15:39 to 18:08
Hear Derek discuss the unexpected hurdles he faced during his first property rehab.
“The deal was done, but this is where confidence gets tested.”
The Reality of DIY Renovations
18:08 to 20:00
Explore Derek’s journey through DIY renovations and the lessons learned.
“And it's a great way to get started because the cost to acquire the property is a lot lower typically than what it would be for a standalone investment property.”
Planning for Success in Investments
20:00 to 22:21
Understand the importance of planning and having systems in place for real estate success.
“I thought initially that again, it was just going to be cosmetic.”
Lessons from First Deals
22:21 to 24:28
Derek shares valuable insights on what he learned from his first investment deal.
“And Derek, I think that's a common challenge that a lot of rookie investors face.”
Show all 19 chapters
Initial Deal Insights
28:13 to 28:38
Derek shares experiences from his first real estate deals.
“I think my first deal, it cash flowed like$150 a month.”
The Importance of Tenant Evaluation
28:38 to 30:24
Discussion on the critical importance of tenant evaluation when buying properties.
“So Derek, what did this deal permanently change about how you evaluated future opportunities that came your way?”
Managing Tenant Relationships
30:24 to 31:56
Tips on maintaining healthy relationships with tenants and the challenges involved.
“Well, I was going to say, how much time do we got?”
Handling Conflicts in Property Management
31:56 to 36:26
Strategies for enforcing lease agreements without conflict.
“Ashley, I want to ask you, because you always talk about how you don't like conflict.”
Shifting Mindset Towards Real Estate
36:26 to 40:02
Derek discusses the mindset changes that come with successful real estate investing.
“So once Derek realized that real estate investing wasn't a fluke, the question stopped being, can I do this?”
Balancing Day Job and Real Estate
40:02 to 41:53
Exploring the benefits of keeping a W-2 job while investing in real estate.
“do that, which is insane to me, but I'm very fortunate to do that.”
Building Your Support Network for Real Estate Success
42:00 to 43:34
Learn the importance of building a network and collaborative mindset for real estate ventures.
“What's the first thing that they should actually build out before their first deal?”
The Confidence Gained from Your First Deal
43:34 to 44:36
Discover how the first real estate deal can transform your confidence and approach.
“Well, Derek, I appreciate so much of what you've shared on this podcast, obviously the tactical side, but more so just the mindset around getting started and the importance of that first deal.”
Connecting with Derek: Insights and Contact Info
44:36 to 45:08
Get to know Derek and how to reach out for more insights on real estate.
“Well, Derek, thank you so much for joining us today.”
Transcript
Automatic transcript. May contain errors.0:00Ashley Kehr:Think you need total confidence or a quit your job moment to break free from the nine to five? Today's guest proves that one intentional deal can turn vague hope into a clear plan. Not long ago, Derek Brickley was still working his W-2, unsure when or how he'd ever exit until one carefully chosen deal changed everything.
0:21Derek Brickley:Now, Derek has a repeatable investing model that gives him certainty around his timeline out of the nine to five without the chaos of burnout. So in this episode, you'll learn how to choose a first deal that fits a full-time job, how to limit downside as a rookie investor, and how one smart move can make your exit from your day job feel inevitable.
0:47Ashley Kehr:This is the Real Estate Rookie Podcast. I'm Ashley Kerr.
0:51Derek Brickley:And I'm Tony J. Robinson. Let's give a big warm welcome to Derek. Derek, thanks so much for joining us today.
0:55Tony J. Robinson:Yeah, I appreciate it, guys. Shoot, really happy to be here. It's been a long time coming, long time listener, first time podcast.
1:02Ashley Kehr:Well, we're happy to have you. But before this deal that you had, what did escaping the nine to five actually mean to you? And why did it feel so far away still?
1:14Tony J. Robinson:It was a drastic shift because I had no idea. And I feel like a lot of people don't, especially when you're just starting out in anything. And that doesn't have to be real estate, it's hard to get the vision in place and put the steps there of where you want to go. Sometimes you might have the vision, the end goal, but it's where do you start? And so for me, I knew ahead of time, thankfully, that when I was in college, I was just like a lot of people who, again, you don't know what you're doing. I went to school to get an idea of what might spark my interest. And I ended up finding, fortunately, the math, the numbers, the finance side of it.
1:53Tony J. Robinson:And that just sort of started this spiral into what needs to happen in order for me to get where I want to go. And so it was always starting with the basics, starting at the first steps and just educating myself on those principles to get to a point where you have more flexibility.
2:11Ashley Kehr:What uncertainties, you know, did you come upon that just made you feel like, you know, you were stuck in this day-to-day and that it wasn't closely achievable to be able to leave your nine-to-five?
2:25Tony J. Robinson:Well, the main thing was the risk of it is the nine-to-five inherently is very structured. You have a fixed schedule. You know exactly what to expect. And once you're able to sort of be that freedom, I should say the limitations is what happens. It's the what ifs. It's the concern about what happens when there's not a steady paycheck coming in. And so that was the biggest mental shift that you need to have, at least initially, is to get out of that way of thinking, the nine to five, the limitations that that provides. And even though there's benefits to it, you still need to reshift your focus as to the positive of what you can actually accomplish.
3:10Derek Brickley:And Derek, it's a great point. And Ashley and I just recorded an episode where we highlighted the three key reasons we feel most people won't actually buy a deal in 2026. And one of the things that we highlighted was what you just said is that a lot of people have this concept that a day job is the most secure thing that you can have in your life. But we also know that that's not true because most adults at some point in their life will be let go. They'll be downsized. They'll have to go find a new job. Even people who work in secure industries like the government. When I was a senior in high school, this was right during the great financial crisis.
3:51Derek Brickley:And my mom worked for the government. She was a government employee, super stable job, great benefits, great retirement, all those things. But during the 2008 financial crisis, they furloughed all of the government employees. And my mom saw her income get reduced by I think it was 30%. And that's a lot for like a working class family, right? So even if you think that you have a quote unquote, secure job, there's still a benefit in going out and building something for yourself. So I love the mindset that you have there. But what actually made you realize that waiting for more time, more clarity, more confidence, which is what most people do when they have the idea of investing in real estate, what actually made you realize that waiting for those things wasn't the smart move or wasn't actually making things safer for you?
4:39Tony J. Robinson:Because you're never ready. You're never going to be fully ready. And that's the thing, you guys know it too. From every deal you do, there's always something that scares you. There's something that you've never done before. And so if you just go into it thinking that you have to have full confidence, you're never going to have it. And in reality, that's going to keep you from getting where you're actually trying to go in the first place. You're going to be detrimental to yourself just because you didn't make that jump. And sometimes it doesn't have to be a big jump. It's just the first step, but having confidence in yourself that you'll figure it out.
5:15Tony J. Robinson:Because in reality, that's what you need to do is surround yourself too. And I think this is another important point, right? Is if you're around people and surrounding yourself with the people who have experience, who know what they're doing, that can supplement where you are and get you to a point where you don't need to know everything. You just need to know who can actually help you with it. So knowing those couple of things, that's the biggest shift because it's just trying to figure out, okay, who's going to make a difference in my life? But in reality, we all know this, right? You have to be the one that makes the change.
5:55Tony J. Robinson:No one's going to do the work for you. So at the end of the day, you got to do what you got to do.
6:00Ashley Kehr:I think that's a great point there is to like, look at your network and your resources around you. And it may not even be a friend or somebody that can, you know, come and help you or whatever, but it could be somebody that you could hire, that you know, that you could trust that would do a good job, you know, such as a contractor, you could feel more confident as, you know, going out and talking to contractors, asking them what they do, finding out what their process is, looking at other jobs that they've done. And that can give you the confidence and know like, okay, I have a contractor that I want to hire.
6:33Ashley Kehr:I have a handyman that can take care of repairs and maintenance. So like your network doesn't need to be people who are more successful than you. So you can leech off them. It's, you know, your network can be people who are more successful that you learn from. It can be people who are in the same stage as you. And it can also be people who are trying to get where you're going and just like the having that kind of like-mindedness where you're both have, you know, you're trying to achieve the same thing and helping each other and, you know, kind of sharing your resources there too. So your network and having those resources available isn't available, isn't just people who are way farther ahead that have already done it that can help you.
7:19Ashley Kehr:There's tons of other ways to have people around you in your network.
7:24Derek Brickley:Yeah, Ash, I just want to add to that because I think a lot of the rookies that are listening agree with the notion that your network is so important, just like you said, Derek, but I think where a lot of rookies struggle, and I'm saying this because this is where I struggle when I first started, is how do I build this network, right? I don't have rich uncles or all these people that are doing this. How do I actually go out there and meet those people and and build those connections. And I think some of the best ways to do that are one digitally, you can join a community like BiggerPockets, you can get active in the forums and the Facebook groups and, and network and meet people there.
7:58Derek Brickley:Then you can do it in person, you can go to local real estate meetups and just be the person that shows up month after month after month after month, and eventually we'll start to meet more people. You can go to bigger events like BP Con or whatever other event kind of piques your interest and spend three days with, you know, a group of folks in, you know, Vegas or Orlando or Denver or wherever and build relationships that way. So it's not going to just fall into your lap. You've got to be intentional about it, but just know, even if you have no one in your personal life today who is going on the same journey as you, it doesn't mean that it has to stay that way.
8:33Derek Brickley:You can go out there and build those connections.
8:35Tony J. Robinson:It's not going to be easy, right? Like that, that's the biggest thing too, just to sort of jump in on that is if it was easy, everybody would do it. And that's such a cliche, but there's a reason that most people don't buy their first deal this year because it's not easy. And buying your first deal is not going to be, again, it's going to be a little scary because you might not have done it before, but there's plenty of resources out there to help with that. And that's what got me into bigger pockets in the first place when I was trying to figure it out It's because I had no clue. I didn't have any connections regarding contractors or even lenders or whatever it was.
9:15Tony J. Robinson:And so the resources are there. You just got to take advantage of them.
9:19Derek Brickley:So Derek, when you finally decided to take action, right, you move past the idea like, hey, real estate is what I want to do. You started educating yourself and you finally decided to act. What did you intentionally say no to in that first deal?
9:33Tony J. Robinson:I set my buy box and I needed to know and I needed to have clarity with that first step, which the first step for me was, what do I actually want to buy? Because there's a lot of ways to invest in real estate, whether, right, you can do whatever you want to do. You can do short-term rentals, long-term, mid-term, you can wholesale, you can fix and flip, but you can't do them all, at least at first. So I had to set the criteria and say, you know what? I have to say no to every other opportunity that is not, in my case, small multifamily. That was what I wanted to do was I knew that for me, the least risky way to get into it, which I learned from BiggerPockets was to go about it with a house hack, buy a two to four unit multifamily property that fit the criteria.
10:27Tony J. Robinson:And that's all of a sudden, once I had my criteria clear, it was so easy because then I'm just looking for that specific deal. And it takes some time, but once you have crystal clear criteria on that, looking for the deal, that's where, again, you can rely on your real estate agent. You can rely on the people in your network. But you can't go to the network and say, hey, I'm looking to get started in real estate investing. I'm trying to find a property because what are they going to say? Right? They're going to go, well, what are you looking for? And if you don't know, they can't help you.
11:03Ashley Kehr:So what specific criteria were you actually looking at and made you feel safe that, you know what, you don't have as much risk and you're ready to move forward, even without total certainty? For me, that needed to be that there is cashflow, right?
11:22Tony J. Robinson:And with a house hack, you're not going to have the same cashflow. You're not going to all of a sudden make a couple hundred bucks living for free. I mean, you might in certain markets, but for me, where I invest, what I was looking for specifically, I wanted to make sure that if the worst happened, if this thing didn't work out, I could rent that second unit because I bought a duplex or at least whatever other rental income was coming in would cover the expenses. And again, it's just meant to reduce your living expense where you live there. But in order for me to conceptualize and accept that risk at the time, I needed to know that I was buying in a strong market.
12:06I looked at the market fundamentals, making sure that there was enough, what would I say?
12:13Tony J. Robinson:I guess just to make sure that in, again, the worst case scenario, that I looked at that and gone, well, if the worst happens, what if? And as long as I'm okay accepting that risk with whatever likelihood it is to happen, it's kind of a mathematic equation for me because, well, again, I get to be the numbers guy, but I always look at it as what are the chances that that actually happens? And that's also something I had to look at is, great, the best thing could happen, but what's the chances that the worst thing happens? And the chances that the worst thing happened were pretty slim. So fortunately, just going through and looking at all the different factors for the market, the cash flow, the rent amounts, any upside in regards to appreciation, forced equity, they were there.
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15:38Ashley Kehr:Okay, welcome back. The deal was done, but this is where confidence gets tested. So Derek, what surprised you the most in the first few months after closing, especially while you're still working your full-time job?
15:51Tony J. Robinson:Initially, I planned to do a cosmetic rehab. I didn't want to go walls in. It was a newer structure, but it was very outdated. And because of that, if that was going to be a place that I was going to live in or someday rent out, the marketability wasn't there. I wasn't going to get above market rent. I wasn't going to get possibly even the best tenant, which I knew was important criteria even at that time. So when I did that rehab, this was right off the bat. We go ahead and start breaking into the flooring, let alone to know that there is pounds of industrial glue that they've just poured on the bottom with staples, stapling three to four layers of flooring in.
16:36Tony J. Robinson:and so it it was it was one of those things you start breaking into it and it's not something you can't overcome but what turns into what you thought was going to be a week-long job when you're doing it yourself turns into months because you're just hammering away at this floor with a chisel every three inches trying to pick up these little industrial staples and it was like okay this is something i did not plan for at all and you break up the bottom layer of flooring and then there's cat pee smell, right? And smoke smell, and there's the tarnish of the smoke on the walls and everything as well.
17:13Tony J. Robinson:And so it was one of those things where it was like, I didn't really know what to expect. But that's when I needed to rely on people who did. I couldn't do it alone. And I didn't want to, because of how much time it was taking away. I I mean, I'm trying to do a full-time job and build a book of business for myself at that time, especially. So it was like, how much time is this taking away from me? But that was the thing that I had no clue was going to happen, at least right off the bat, within the first month of what I got myself into.
17:49Derek Brickley:So Derek, you chose to purchase a duplex as a house hack. and for our Ricky listeners that aren't familiar with the house hacking phrase, I think most of you are, but for those that aren't, house hack basically means that you're buying an investment property, but you're also living in it as well. So you live in one area of the property, you rent out the other area, and that's what you opted to do. And it's a great way to get started because the cost to acquire the property is a lot lower typically than what it would be for a standalone investment property. But you also opted, Derek, it sounds like, to at least do some of the renovations yourself, right?
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18:22Derek Brickley:You talked about chiseling away at the floor every three inches or so. Did you have experience in like renovation already? Like were you handy to begin with or was this more of a YouTube university route? And if so, what made you feel that DIY was the best approach for you specifically?
18:41Tony J. Robinson:It was mainly focused on cost at the time as the reason for why I did a lot of it. Now that's not to say there was certain things that I could not and would not do because I'm not handy. I am not that guy. So for me, I knew right away that there was going to be things if they came up plumbing, electrical, I needed somebody who's experienced and wouldn't burn the house down. So yes, there was those certain things, but otherwise anything I could do myself was basically one of those things of, well, it seems to make sense because it's going to save me the money of hiring somebody else, but then you quickly learn how much time that actually takes away from you.
19:24Tony J. Robinson:And that's when I immediately started to realize, okay, I got to figure out what my time is worth too, because at the end of the day, right, you only have so much of it. And it's not scalable to do all of the rehabs and everything yourself. It can be fun, a little frustrating at times, especially as you're trying to learn it all, but you take away those lessons.
19:44Derek Brickley:And I want to get into the systems and the scale, piece because I think that's important for the rookie listeners. But just one last question on the renovations. How much time did you initially plan for the renovations and how much time did it actually take to get through it all?
20:00Tony J. Robinson:Wow. So it was a pretty big jump. I thought initially that again, it was just going to be cosmetic. What can go wrong, right? You're just going to lay down some new floor, maybe put in some new cabinets. What was expected to be maybe four to six weeks turned into about six months of just trying to go through it all. And the other thing too is timing it because, wait, okay, great. I got the floor done. Oh, wait, did we ever call that guy that's supposed to come next? It's like, no, we didn't actually think that far ahead. So it took a lot longer than we initially thought it would. Thankfully, again, as a house hack, right, I had that flexibility where I was able to take a little bit of time to do that.
20:50Tony J. Robinson:I wasn't in a huge rush. I know some people that we help with house acts on our side, right? They do more of like a fix-in or sorry, a live-in flip where they might go in and actually do the construction while they live there. But with what we were doing, that wasn't in my cards.
21:06Ashley Kehr:So where did the plan like start to break down and you have to really systematize faster than expected? What were some of the first systems you put in place that maybe you wish you would have done even before buying the first deal?
21:21Tony J. Robinson:I should have known right away before buying the first deal, what work was going to be done and who was going to do it. And that's the part that I missed. The second part specifically is I just knew a general idea. You look at it when you buy the, you know, you buy your first deal, you're going to get a home inspection most likely to get an idea. and when you go through it, they'll tell you a few things that probably need to be fixed, which is what their job is, that's expected. So you should have an idea even before you buy the property, who's going to do at least those basic things. And if you're going to do a cosmetic rehab, knowing who's going to put the flooring, knowing who's going to do the plumbing.
22:01Tony J. Robinson:Because when you don't know, when you haven't reached out to a contractor or some handyman who can help with some of the little things, you don't know what your time frame is going to be. And so that was the biggest thing that got away from us is just knowing ahead of time and planning that process out.
22:21Derek Brickley:And Derek, I think that's a common challenge that a lot of rookie investors face. And there's a book from Bigger Pockets written by Jay Scott. It's the book on flipping houses. You guys can pick it up at biggerpockets.com slash bookstore. But I remember when I did my very first rehab, I read that book like front to back multiple times to try and figure out, okay, like what am I actually getting myself into? And maybe what are some of those common pitfalls that most rookie investors make that kind of sets them back? and it's a really great book. And Jay Scott's like one of the smartest guys that I know.
22:52Derek Brickley:So again, if you guys want support on that, it's the book on flipping houses. But as you were going through this, Derek, there were obviously a lot of unplanned challenges. And I think that is part of doing your first deal. Like that's the purpose of that first deal is to educate you, to teach you the lessons, to lay the foundation so you can then scale on and up to your next deal and your next deal and your next deal. And I guess I'm just curious, you didn't stop. How many deals have you done in total now?
23:22Tony J. Robinson:I'd say since then. So just to give the listeners context, I bought that first duplex in December of 2023. So now here we are two years later, and there's been three additional deals.
23:36Derek Brickley:Right. So you've continued to transact as a real estate investor. So obviously you continued. So I would assume though that there was a moment when you questioned on that first deal, is this even worth it? Like, like, you know, are Tony and Ashley just like spewing lies in this real estate rookie podcast about what it means to be a real estate investor? What, what pulled you through that moment to allow you to continue on to do number deal or do deal number two and three and four?
24:05Ashley Kehr:And just to be clear, the only time I lie on this podcast is when I tell Tony He looks great in his black shirt. I have every single recording.
24:15Tony J. Robinson:Well, yeah. So the thing that really made it stand out for me is seeing that it was possible and knowing what was on the other end of it. No, that deal wasn't. I still own that property. And it is not a home run. It doesn't cash flow a ton. It basically breaks even at this point. But the lessons that I took away from it, I knew would set me up so that the next one was just even better. And that's what I had fortunately started to see with a lot of the investors that we work with. That's what I started to see with the personal network I started to grow is that we all have our first deal. And everybody does.
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28:13Ashley Kehr:I think my first deal, it cash flowed like$150 a month. And then I had even forgotten to include snow plowing. So it ended up being even less than that. But it still got me started. I bought the second deal within three months after that. And that's such a great lesson. It's like it doesn't have to be a home run. It doesn't have to be the most perfect deal. So Derek, what did this deal permanently change about how you evaluated future opportunities that came your way?
28:46Tony J. Robinson:The biggest thing that that shifted for me was qualifying your tenants. and you guys probably have some horror stories about these, but starting to realize, right, when you buy an investment property, chances are you're going to inherit one or more tenants that are already in the property. Maybe they've been there for a long time and that's great. Good for them, but you got to make sure you're doing your due diligence. And so going forward, making sure that you know exactly who's in your rental property, right? And I say that for a reason, but whoever is in the property, who's on the lease, what does that look like?
29:31Tony J. Robinson:And what are their terms and understanding what your responsibility is to them as well. Because as a real estate investor, right? Our job as a, I should say a long-term real estate investor is to provide housing for these people. It's to make sure that they have a safe place to live, a good place to live. And so sometimes things have to change in order for that to actually happen. And not everybody might be on board with that, but in the end, that was the biggest change that I had to have then and going forward is making sure that, again, you know who's in the property, you know your tenants, and you're actually serving them in the way that you should.
30:16Derek Brickley:Derek, I feel that maybe that lesson is based on an experience that you've had with some tenants. So do you self-manage all of your properties?
30:26Tony J. Robinson:Yes. Well, I was going to say, how much time do we got? Because with that, and to summarize it, I came across this where the tenant that was in that original duplex is still there, but she's a great tenant, always pays on time. She's been on the lease for seven years with the prior owner. And what happened is over time that I had purchased the property and started to own it and operate it, we got a little flexible. and you know i'm trying to think with that specifically because when you are flexible on one thing maybe you know oh okay you have a new cat i didn't know about that that's okay though right a cat can't be a problem until again long story short next thing i know there's three people and nine cats in a two bed one bath duplex and like okay well this is not the best for anybody.
31:31Tony J. Robinson:So staying on top of it, making sure you know what's actually happening in your properties as well. And not just, we all want things to be as passive as possible. We don't want problems. We don't want maintenance, but the routine maintenance, the checkups, the things that you'll do in the middle are what are going to protect you, your asset. And again, make sure that the tenants actually have a great place to live. And it's something that is good for their situation.
32:00Derek Brickley:Ashley, I want to ask you, because you always talk about how you don't like conflict. And there's probably a lot of folks listening who feel the same way. And I think it's even harder, especially as a first-time landlord, to enforce rules on other people. So what have you found to be the best way to make sure that tenants are respecting the lease, respecting the property without all of that like internal dialogue or, you know, internal turmoil over creating conflict with your tenants. And don't say that you may dare, I will do it.
32:38Ashley Kehr:That was definitely going to be one option. You will let somebody else be the person that communicates. And it either goes that he can be the bad guy or he's saying, I'm so sorry. She said that no, whatever. So I don't even have to, you know, save face. But really, one of the best ways is lease enforcement is so like having as much as you can in your lease and just saying like, this is in the lease. We both signed it. We both agreed to it and making the lease the bad guy. So that I think really should be the number one thing. And then the second thing is to have somebody else that's maybe the communicator, the middle person or whatever.
33:27Ashley Kehr:There was a time period where people just thought that I was the property manager and that I was not the owner of the property. So I always blamed stuff on the owner, even though it was me, and they just thought I was the property manager. Um, but over time I just, I, I felt like that was almost like deceitful in a way, but it really did help diffuse situations by not letting people know that I actually own the property. And, um, but yeah, there, there's a couple of different ways, but I think really the best way, uh, is to, you know, enforce the lease and then have that communication and writing emails.
34:07Ashley Kehr:If you have a property management software. Like I use TurboTenant. You can message right through there and have the conversation in writing. Having things in writing has saved me so much. I had a tenant sue me for their security deposit. The judge dismissed it. One of the reasons right away was because I told my VA, I told my contractors, anybody, I said, do not take this person's phone call only in writing. So emails only, text messages only. And because we did that, we had everything in writing, which helped our case and it got dismissed. And so I think that would be another big thing too. And it gives you time to think.
34:51Ashley Kehr:Definitely when I was very early on being a property manager, like I can think back to sometimes where I was immature. I was not professional. I was reacting with a hot head and frustrated and just like, how can they even be asking this? Like, this is ridiculous. And, you know, thinking those things. And I think also having it in writing, it gives you a second to, you know, think about what's the appropriate way to respond to this. And like, I, like for my, a PMS system for short-term rentals is hospitable and they have their AI chat, you know, respond for you. And it's just like, that is the best.
35:33Ashley Kehr:If you can put, throw your response into AI and like have it approved, like, okay, yep. This is how we can make it sound nicer. And you're more customer service. Like that's also a great way to handle conflict too, is to have AI actually write your responses.
35:50Derek Brickley:There you go. Well, there is a masterclass on enforcing the rules of the lease without creating a bunch of conflicts. I appreciate you walking through that, Ash.
35:58Ashley Kehr:I have a book recommendation too. It's by Jay Baer and it's called Hug Your Haters. And it goes through like basically how to kill people with kindness and customer service. And I think that is super great for handling tenants.
36:13Derek Brickley:One additional book recommendation, it's called Crucial Conversations. And there's like a few folks who wrote that book, but if you just Google crucial conversations. It's another book that does an incredible job of giving you frameworks to use when you have to have somewhat difficult conversations. So once Derek realized that real estate investing wasn't a fluke, the question stopped being, can I do this? And became, how fast do I want to? So up next, we're going to talk about how that clarity created a real timeline to get Derek potentially out of his nine to five. All right. So now that the model works, everything else starts to look different.
36:47Derek Brickley:So Derek, how did your decision making change once you knew that this path of real estate investing actually worked?
36:54Tony J. Robinson:So once I started to see the bigger picture, that's when I was able to go ahead and say, what do I need to do to get there? And again, that's the way that my mind thinks. I know I've said that a couple of times already, but it's always thinking about next steps because getting to the end goal can seem like a huge jump. It's like, how do I get from buying my first property to get where you guys are? How does that even happen? It happens one deal at a time. And so just focusing on the next one and the next one and the next one and what I want to get out of it, that was the biggest shift that allowed me to go.
37:34Tony J. Robinson:Working a nine to five didn't get me that. that wasn't something that I saw being scalable, right? Because if you have all of your time tied up, you're in the office and I say that, right? But I mean, working as a lender, yes, I'm still in the real estate industry, but like I needed to not do something that wasn't going to play out that way. Something that wasn't going to help me figure out how to get exactly where I wanted to go. And so being able to actually be in the business allowed me to focus all of my effort and thoughts and energy around what I can do to better myself and allowed me to see a lot of context, too, for what other people are doing.
38:21Tony J. Robinson:And that was one of the things that helped me grow my network.
38:23Derek Brickley:Right now, you're still working your your day job, Derek, but what is your exit timeline look like now? And why does it feel more realistic given what you've accomplished so far as a real estate investor?
38:37Tony J. Robinson:For my time frame, I just look at it as a supplement. Right. This is something that I enjoy to do. And I think that's one of the biggest things a lot of people underestimate is I need to get out of my nine to five as quick as I can or my day job. I got to quit. I can't do this anymore. That's a good goal by all means. But having that there can sometimes actually be the reason that you're allowed to keep buying properties, right? You can have multiple sources of income, multiple income streams that help grow that. And so in terms of to answer the question of an exit timeline, it's like, why would I stop until I get to a point where I can't when I don't have the time to do it but as long as I put the systems and delegate the things that I need to do I'm just living life right like I'm just enjoying what I do and making the most out of it and that's kind of how I get to approach every day at this point is I can look at it as something I get to do rather than something I have to do.
39:43Tony J. Robinson:And that is the goal. That is the end goal. It's not about necessarily, well, I can't wait to leave this place. It's, do I have the flexibility that I want out of life? Can I do the things I want to do? And for a large part, I've been able to already do that, which is insane to me, but I'm very fortunate to do that. But it's taken a lot to get here.
40:10Ashley Kehr:Yeah, it definitely has. And I think that just sharing this opinion you have about quitting your job or keeping it, like maybe if you really do detest your job this much that, you know, building this real estate portfolio can offer you the opportunity to go part-time or to maybe transition to a different job that's more fulfilling, but maybe it's less pay. So I think the really important thing to think about is not only real estate as a tool to quit your job, but also how much faster and efficiently you can build wealth by doing a W-2 job or building a business while simultaneously investing in real estate investing too.
40:57Ashley Kehr:So I think oftentimes and I think back to like, you know, COVID in 2021, where like it was a lot of people I felt like quit their jobs and went full time into real estate because it was a gold mine. Like, you know, properties were appreciating like crazy. You could flip a house and make a ton of money. But how sustainable is that? And I think there's a lot of, you know, you can feel more comfortable and confident in keeping your W-2 job and investing in real estate. And it kind of gives you that balance to have even a bigger safety net. If a deal, you know, something happens with the deal, you have your W-2 income that you can help supplement that.
41:41Ashley Kehr:Something happens with your job, you have your real estate income to supplement that. So I think there's a lot of pros and cons to all sides of it, keeping both or just doing one or the other. So definitely something to think about. But if someone listening, Derek, they want the certainty and not just the hype. What's the first thing that they should actually build out before their first deal? What should they be thinking about? who not how that's the biggest thing is you don't even need to know how you're going to do something
42:16Tony J. Robinson:because again things are going to change things are going to come up things that you didn't expect but if you know who's there to support you who's there to help get you through it who's going to do the different parts of that process that is the thing that'll set you apart as you go through it and give you that certainty of not, it's not, can I do it? It's, can we do it? My network, do I have the network to do it? Can this business and approaching it from the entrepreneurial mindset instead of the maybe DIY mindset of I'm going to do everything myself, that's great. Can you really though, are you the best person to be able to do property management?
42:58Tony J. Robinson:And I say that right as we self-manage but like there's different aspects of the real estate business that it rely on the people who know better than you do because i don't know everything and i'm not going to pretend that i do but i know people who know how to do that so it's like as long as i have that connection building that and starting to work on figuring out who can help you through it what resources you have and can take advantage of, those are the systems that will scale.
43:34Derek Brickley:Well, Derek, I appreciate so much of what you've shared on this podcast, obviously the tactical side, but more so just the mindset around getting started and the importance of that first deal. But looking back, what did that first deal actually buy you that money alone couldn't?
43:53Tony J. Robinson:It bought me the confidence that I could do it, right? Because that house hack was also my first property. So it gave me the confidence that, okay, I can buy a property and work through it. I can manage it. Like, I'll figure it out. And that was the biggest shift is from not having the certainty, being a little scared of like, what's going to happen? How does this work out? What if this doesn't work out? And that confidence shift of being able to go, oh, that worked. I can do that again. I can do that better. I can do this better. It just gave me a leg to stand on.
44:38Ashley Kehr:Well, Derek, thank you so much for joining us today. We really appreciated you taking the time to share your journey and your experience. Can you let everyone know where they can reach out to you and find out more information about your journey?
44:51Tony J. Robinson:Yeah, absolutely. So feel free to reach out to me on any socials. My tag everywhere is LoansByDB. So feel free to connect, DM me. I'm always as responsive as I can be. So if you shoot me a message, I'm sure I'll get back to you as soon as I can.
45:07Ashley Kehr:Thank you guys so much for joining us today on Real Estate Rookie. I'm Ashley and he's Tony. Thanks so much for listening. We'll see you guys on the next episode. At some point, your little real estate side hustle stops feeling little. Rent's coming in. Maybe you've got a couple properties now and suddenly the money part gets real. Your tax bills going up. You're Googling LLC versus S Corp at midnight. And you're just hoping you didn't miss something that'll cost you later. That's where Collective comes in. Collective is the first all-in-one financial solution built exclusively for solopreneurs, saving you time and money.
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46:11Ashley Kehr:Right now, Collective is giving you 50 % off your first two months when you go to collective.com slash rookie. That's 50 % off your first two months at collective.com slash rookie.
46:20Derek Brickley:Hey, rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie Podcast. Now look, you don't need to be an expert. You don't you've done one deal, your story could help inspire the next listener.
46:39Ashley Kehr:As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal.
46:51Derek Brickley:So head over to biggerpockets.com slash guest. If you want to be a part of our show again, that's biggerpockets.com slash guest. And we'd love to have you on.
From the publisher
The what-ifs of real estate investing keep many rookies on the sidelines indefinitely. But when today’s guest determined his “safe” nine-to-five was just as uncertain as buying a rental property, he took the plunge. Now, having bought four small multifamily properties in just two years while keeping his W2 job, he’s fast-tracking financial freedom!
Welcome back to the Real Estate Rookie podcast! Like many rookies, Derek Brickley dreamed of owning a sizable rental portfolio, but taking that first step was his biggest hurdle. He could have allowed his blind spots to keep him trapped in analysis paralysis, but instead, he leaned into his investing network and drummed up the courage to buy his first house hack. It wasn’t a home-run deal, but it changed everything, teaching him how to make offers on properties, plan renovations, and manage tenants.
Now, Derek has the tools to scale his real estate portfolio and an investing strategy that has set him on a clear path to financial freedom. Rather than using real estate to supplement his day job, his W2 income now supplements his investments. Stay tuned as he shares his highly “repeatable” process!
In This Episode We Cover
How Derek bought four small multifamily properties in just two years
Building your rental portfolio faster by keeping (not quitting!) your W2 job
Leveraging your investing network to bridge the knowledge “gap”
Having tenants pay for your living expenses with the house hacking strategy
How to do your due diligence before inheriting tenants with a rental property
Critical mistakes to avoid when tackling do-it-yourself (DIY) renovations
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-680
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
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