Making $10,000/Month Cash Flow from 5 Rental Properties in Just 5 Years

20:34Jamie Trickett:Well, I also don't want anyone to think that I did it perfectly because I did not. I fall into that category of analysis paralysis. I think with the first deal, it's because there was a goal and unintentionally the goal was a place for retirement in 20 years and so I still have that happen to me my properties I have short term I have long term I definitely do get shiny object it's hard because once you get the real estate bug you just want to learn about everything and understand how everything works but in I did feel like I was drinking from a hose. I just didn't even know which direction to go in first, whether it was legal structure, operations, properties, markets.

21:19Jamie Trickett:Like I said, I didn't even know what an MTR was, but I couldn't agree more. And so the evolution that I have is that, you know, just like everything up and down, I now am focused on STRs. I truly enjoy them. I really, it might not be what I do forever. But that is the area or that what I would call asset class that I enjoy, even though I have a few other asset classes as well in the long term space.

21:45Real Estate Rookie:Jamie, let's talk about that, right? Because you said you've added a property every year since you started and you've got two STRs, two LTRs, another short term rental that you're closing on. What was the idea behind that diversification and why not go all in on just one strategy?

22:00Jamie Trickett:Yeah. Again, I am risk averse. mostly. So I wanted to have a bit of balance. I wanted some cashflow. I also didn't understand the tax benefits of, if I'm being a hundred percent honest at the beginning of this real estate journey, I had asked our CPA recently, it was a couple of years ago, actually, maybe a year ago, if I should do a cost segregation because I had acquired a few properties. And he told me, know that they're not worth it. They're a waste of your money. And so I thought, wow, I've heard about it on BiggerPockets. I kept listening. I went to go look it up and research. And of course, it was incredible.

22:42I did execute the cost segregation study.

22:45Jamie Trickett:It was a huge tax savings. It actually allowed me to purchase one of my other properties, giving me the down payment for that. Jamie, I want to stop you right there because cost segregation, I think, is just not talked about enough. I think it's slowly becoming more and more. But I invested for probably seven or eight years before I even knew what a cost segregation study was. So maybe just to break it down, you hire a third party to go through your property and to basically turn it into a line item where you can write off, depreciate things as a different bucket, I like to call it. So like the actual property itself, it's, you know, depreciated over, you know, what is that?

23:30Jamie Trickett:39 years, 37 and a half years. Then you have your, your other bucket of like fixtures and, you know, furnishings, things like that. So like they go in and like count the windows, you know, count the trim pieces, things like that. And you're able to depreciate those more quickly. So that increases the amount of money that you are allowed to expense every single year. So Jamie, do you remember offhand, like if you could give us an example, what was the cost of one of your cost segregation studies? And then how much did you be able to write off that year? So again, I didn't know about cost segregations until the last couple of years.

24:10Jamie Trickett:So what I ended up doing was bundling three of my properties and doing a cost segregation on all three of them. So I think the average cost was$2 ,200 each. My CPA had thought it was$20 ,000 each, and that would be my savings. So he didn't understand, and it wasn't his fault. He didn't focus on real estate, right? So it was$2 ,200 each. And I think when all was said and done, and I used all three properties, And I'll just take a side note because the properties that I had purchased, there wasn't 100 % bonus depreciation at the time because I had a 2022, 23, and a 24 purchase. They were all different percentages.

24:59Jamie Trickett:I was able to recoup$150 ,000. And so that was able to, like I said, I could reinvest it. Other people would do different things, but I am in the growth phase. So I just reinvested it into other properties.

25:15Real Estate Rookie:Jim, I just want to clarify for the listeners, when you say you got back over six figures, like logistically, what does that actually look like? Like, is it, you know, once you do the cost seg, you just immediately get this check back for 100K or like, how are you actually getting that money back?

25:28Jamie Trickett:Yeah. So I did the cost segregation on all three properties and then that was included in my tax return. It was actually the 2024 tax return. So when I thought maybe we would owe some money, I decided to make this pivot in my career, actually April of 2024. So I'm just about my two year mark right now in a couple of weeks, actually. So when we got our taxes back in 2024, it was a refund and my husband and I couldn't actually process it. We thought, wait, let us just go back and make sure they did this right. So we sat down with the accountant. we had changed to an accountant who's a bit more focused on real estate who understood cost segregations.

26:13Jamie Trickett:They walked us through the tax savings and we're like, this is great. What property am I going to buy now?

26:20Real Estate Rookie:And I just wanted to highlight that for the listeners that like, when we talk about, you know, the, the cost segregation studies, um, and, and bonus depreciation and, and kind of getting that tax benefit back or getting that, you know, getting that pile of money. It's not like someone's cutting you a check as soon as you do the cost segregation study. It's once you actually file your taxes, and usually it comes in the form of the tax refund for whatever tax year it's associated with. But what you laid out though, Jamie, of buying a property, doing the cost segregation study, leveraging bonus appreciation, qualifying for material participation, once you check all of those boxes, that next year's tax return is usually big enough to then hopefully fund the next acquisition.

26:58Real Estate Rookie:And it just becomes a cycle where every purchase then creates this big tax benefit, which then funds the next deal and the next deal and the next deal. So you're getting all of the tax benefits and you're getting the cashflow and you're getting the appreciation, which is why for high income earning W-2 professionals, short-term rentals are sometimes the best asset class to go after.

27:16Jamie Trickett:And Jamie, did you file 2025 yet as to how much you're still from that first cost seg? Because you didn't have 100 % bonus depreciation. So this year, will you have another huge cost savings? We believe so. So we're still doing that. So it's a great point. So our purchase in 2025 was a higher purchase price. And so bonus depreciation we purchased in March of 2025 and 100 % bonus depreciation came back in January. So since then, we did do some land improvements like at a pool and an outdoor kitchen because we knew that that would be captured with 100 % bonus depreciation. And Tony, I did want to mention something you said is that I was able to material participate or qualify for rep status because I decided to leave my job in April of 2024.

28:12Jamie Trickett:It's definitely something you have to do. When I was making my decision, I weighed out because exactly to your point, it's not just cash flow, it's tax savings, it's appreciation. And then it's the equity for, you know, renters, whether it's long term or short term guests paying down the principal. Now, Jamie, I want to compare like, you know, a lot of investors are focused on cash flow. Now, I just think the tax savings and even just appreciation are often left out when you're analyzing a deal, you're looking at cash flow. So what are your properties cash flowing? Because, you know, is it a ton of money where you're getting both or is it kind of evening up?

28:52Jamie Trickett:Yeah, it's a great question. So I am very fortunate. I mean, I would like to say that I did this perfectly. I do think it was a bit of luck. I'm going to get better and better and I'm growing every day and learning more again, thanks to BiggerPockets. But so from a gross perspective on the four properties, I did just close on a new property the other day.

29:12Real Estate Rookie:Oh, congrats. There we go, Jamie. me.

29:16Jamie Trickett:But if I focus on the four properties gross, I am grossing$20 ,000 a month. So net after all expenses. And again, I've learned from the BiggerPockets, you guys, and the other BiggerPockets team. When I say net, I mean everything. HOA, CapEx, mortgage, cleaning fees, supplies, you name it. my goal was to net approximately$10 ,000 a month. And I'm almost there with the four properties. But based on my forecast with the fifth property, I'm going to far exceed that number. That is amazing to be able to get that cash flow. And you're having this huge tax savings. I think we need to transition now into how this actually made it possible for you to leave your W-2 job and how this all kind of, all the pieces fit together for you to be able to leave and feel comfortable with that.

30:11Jamie Trickett:Exactly. So, I mean, it definitely gave me confidence that, you know, I have the cashflow coming in. We talked about the tax savings. The other thing was appreciation. Obviously in 2021, 2022, the markets were crazy. So the property that we purchased in Florida, I just looked. And even though Florida has definitely decreased in terms of the demand for price, I've actually had appreciation of about 22 % on that property already. And that's now, not at the peak, which is actually funny because I thought when it was skyrocketing, like just to give you an example, I purchased it for$475 ,000. Again, 4.5 % interest straight, which is almost funny now to think about.

31:02Jamie Trickett:And at the peak, it was$650,$675. And people were saying to me, oh, just sell it, just drop it. And at the time when I was working, I didn't have the headspace to think about what I would do with those proceeds. And so I didn't. So now it's come down a little bit, but it's okay because the numbers still work, it's cash flowing and I have the appreciation. So based on my portfolio, I have some properties that the long-term are more stable. Some are more appreciation plays. The short-term rentals are more cashflow plays. So I'm balancing out a bit and I have different markets. So I have some in Florida, I have some in New Hampshire and my new property is in Maine.

31:45Jamie Trickett:And tomorrow morning, I'm flying down to North Carolina to look at more properties.

31:51Real Estate Rookie:You're doing all the things, Jamin, I love that. But I wanna talk a little bit more, right? Because you have this role as a product manager. And I know my role as a W2 employee working in supply chain distribution, people leadership. That's actually helped me a lot as an entrepreneur. So I'm curious, you come from a world of financial models, product roadmaps. How has that corporate experience and toolkit specifically helped you run your real estate business differently than maybe most usual rookie investors might have?

32:18Jamie Trickett:Yeah, no, it's a great point. So I think a couple of things. I'm always thinking about the user experience. So when you design a product, for example, someone might tell you, I want a red button or a green button. That's not actually what they mean. They might mean, I want a warning if my trade is actually exceeding 2 % or two basis points or something. So same thing with the properties is trying to determine who are the avatar, who are the guests that am I creating this for? If it's a long-term rental, that's different than the short-term rental. I'm so fortunate. I have paired up with an incredible designer who is helping me like execute on that plan.

32:59Jamie Trickett:But the other thing is making sure I have the systems in place. And so because that was my background, that's actually what I did from the beginning. And this is definitely, it's an individual decision. So for example, legal structure. Do you want to keep properties in your name? Do you want to have an LLC structure? and that's all just dependent on the person, but also bank accounts, bookkeeping systems. You know, the first property, I just kept an Excel spreadsheet and hopefully I would make sure that I accounted all my expenses, but who knows, right? I was trying to do the best. Now I've taught myself bookkeeping.

33:38Jamie Trickett:So I do bookkeeping. I use a bookkeeping system, separate bank accounts, separate cards. So it's really helped me do that. Also in terms of looking at the data, you know, which are the markets that make sense? What are the projections? It definitely can feel overwhelming. But I think even unknowing to me, when I first found that first property, I picked a location where the population was growing and job growth was growing. And I must have done it unconsciously. I was just trying to find places where, you know, people I would want to go and other people would want to go. So all of that, taking the data into account, just like you do from product design and making decisions on how you prioritize certain things has definitely helped when I look at these properties.

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38:43Real Estate Rookie:That's n-r-e-i-g dot com slash bppod. All right, so we've seen how Jamie built the portfolio, but what most people don't talk about is what happens emotionally when you leave a very structured career and suddenly you're figuring everything out on your own. So let's talk about what that transition actually looked like and what she brought with her that made the difference. So Jim, you came from a big corporate team, then suddenly it's just you, you know, your laptop and a bunch of properties to kind of figure out. What did that, maybe isolation might be too strong for her, but what did that feeling of being on your own feel like?

39:17Real Estate Rookie:And how did you work through that when you first made the transition?

39:20Jamie Trickett:Isolation is not too strong of a word. It was lonely. You know, you don't know what you're doing. You're not sure which direction to go in. I am at this point consuming podcasts nonstop. I am on BiggerPockets website looking at every single market data that you offer or on the forums, right? The BiggerPockets forums and asking questions and seeing what people are talking about. But it was still lonely because with a team, we would get in the office and have a whiteboard session and start figuring it out. And everybody would come up with ideas. And you felt so proud to be part of a team. I think some people are wired like that.

40:00Jamie Trickett:And I realized that I was. So I have tried to join communities and it's really helped, you know, being in rooms with like minded people or people who have executed on what you already want. they've already done it and you could learn from them has been incredibly helpful. It does give you, you know, that's this kind of sad part in the beginning. But the good part is that it does make you realize that there's so many good people out there, again, just to make help you learn. And people are willing to offer to share their experiences. Now, Jamie, you joked that when you first left the finance, you were told by people that you were retired.

40:43Jamie Trickett:but really the reality was you started working another job, building a business. And how did you learn to protect your time and stop letting the business consume you? Because even earlier in the episode, when you're talking about it, you know, being present with your kids and having it in the back of your mind, even as an entrepreneur, that is still really hard to do to, you know, not think about your business too. Exactly. And another mistake I learned was I did not time block. I did not hold a schedule. I just let anybody's whim that they needed, I would help them or I would be constantly, you know, paying a bill when it came in.

41:22Jamie Trickett:I had no structure. So I very quickly determined, okay, there's certain times I'm going to do like thought work and just try and block out three hours and, you know, undistracted hours to focus on what I needed to do. There's times to, you know, file your taxes monthly or make sure you're paying your bills. But then that gave me time that I could focus on when worked best for me, whether it be once I got the kids off to school and, you know, got a quick workout in and just sat and locked in and got the work done while they were at school versus sometimes, you know, I would be working late at night and just really had no control.

42:02Jamie Trickett:I really just was able to take control of my schedule. So it was incredibly helpful.

42:07Real Estate Rookie:Jamie, talk to me really quickly about time blocking. Like, like, what is that concept? And why have you found that as a valuable tool for you now that you're a solopreneur running this business?

42:15Jamie Trickett:Yeah. So again, I would joke that I was retired and my husband would say, stop saying that you're working harder now than you did before, or maybe at least the same, you know, maybe not harder. But, you know, somebody would ask me something and I would drop whatever and, you know, do a carpool or do this or do that. And so what I do now is I have dedicated days. So whether it be, you know, Monday mornings, I get myself organized for the week or Fridays to get myself organized really for the following week. But I have time that I'm running all my numbers. I'm reviewing my properties. It's, you know, are the tasks daily, weekly, or monthly, some are quarterly.

42:54Jamie Trickett:And I have those all in my calendar, just like I did when I was working. If there was a meeting, there was a meeting. So now, unfortunately, most of those meetings are just with myself. But I do honor that. And so, but it also gives me time that if something comes up, I can look at my calendar. For example, if my kids have an activity that I can just adjust and determine, okay, can I move this, you know, financial review till tomorrow or next week and make those decisions. And you joke that, you know, even if it's just a meeting of one, but like sitting down and making time for that stuff is so important.

43:32Jamie Trickett:You know, going through the financials, seeing where you're at, even if it's you doing everything, it's still hard to have that financial clarity of like, okay, I know I paid the bills, so I know what's going out. I collect the rental income, so I know what's coming in. But actually sitting down and going through every single line item, looking at your financial reports, seeing, you know, your bank statements, things like that is still so important, even if you are the person of one, like setting aside that time to review different things, because I know there's things that I've missed or things that I don't think added up the way that I thought they ended up, you know.

44:09Real Estate Rookie:But Jimmy, you did all this because you wanted some semblance of time freedom and that presence back with your family. So what does an average week look like for you now? Kind of paint the picture for the Rickies who you're listening, they got that return to office notification. So they're maybe listening to this at their cubicle right now. What, what does an average week kind of look like for you? And do you feel like you've actually been able to accomplish what that, that original goal was?

44:33Jamie Trickett:Absolutely. You know, my focus is my kids in the morning. So make sure that they're all set for school. If I'm driving carpool, I joke, but I love it. I love hearing what's happening on their day. because I didn't actually have that opportunity before. So I definitely cherish those moments. So get them off to school. We got a puppy because I'm home now or a little bit flexible. So we have a puppy, take care of the puppy. And then I'll come back and spend a couple of hours definitely on the properties, whether it's just making sure I'm reviewing things or things that I'm learning or hearing, right?

45:14Jamie Trickett:the importance of what kind of insurance do you have or, you know, all the tax rules. I have to say in the beginning, I didn't know any of it. I just hired a CPA when I worked at W-2, hand over my forms and never thought about it. I never thought about all the different facets of it, but now I feel like I am running my own business. And so I run it just like a business. I check in every day. I check on, I do the bookkeeping still. Once I grow bigger, I'm not sure I will, but it's super helpful for me to understand where are the expenses, where are the income and outputs going. So I definitely do that.

45:55Jamie Trickett:I am always looking at properties and opportunities, but I'm also trying to network as well. Again, being in the communities, being with like people, I will talk to anybody about real estate at any time of day. And then in the afternoon, I will go and get the kids or make sure we have dinner and drive them. I joke that I'm mom Uber in the afternoon, but again, I wouldn't trade it for the world. I have time with my husband and my friends. So I definitely feel very fortunate and grateful that I took this leap. And I think it does kind of change your mindset instead of around, oh, I got to drive the kids here.

46:31Jamie Trickett:They have so many sporting vans. I have to drive them to school because during COVID, my kids attended private school and they had to be driven. And I had that mindset of, oh, now I have to drive them to school. They can't take the bus. And somebody else, I hadn't told them any of this that I was thinking. And they had said, oh, I'm so lucky with this new job that I got. I get to drive my daughter to school. And I was like, that's funny you say that because I I have to drive and like, I feel like it's an inconvenience. And he's like, how many parents get that time in the morning with their kid?

47:03Jamie Trickett:Like we talk about this, you know, we sing songs and stuff. And hours since then, it just reframed my like thinking of that. And even now they could take the bus, but I still drive them and pick them up most days. So it is like interesting how you're, how just you reframe your mindset can really change how you perceive things in life. Exactly. Exactly. And I think so my boys don't even have an option for a bus and their carpool. It's 25 minutes one way, but I never did it before. And exactly what you said. So I would miss the after school pickup when I was working. And so now I realize they get in the car.

47:45Jamie Trickett:Oh, mom, so and so said this or something happened funny or something they were proud of that they did that day. Because when I would get home from work, they were so tired and I was constantly rushing. I would say, so how was your day? How was your day? What happened today? And they're just like, it's good. Got one word answers. And now I know their friends. I know their teachers. I know what's happening. I know how they're feeling. One other thing that actually really resonated with me when I was working, I was having a hard time when I first had kids working in technology. It's long hours and grueling.

48:19Jamie Trickett:Like I had slept in a server room before. It's just, you had to do what you had to do. And I remember there are two women that I work with who are engineers. And they said to me, when they're little, they're not going to remember. But when they get older, they'll remember that you're not there. So put in the time now to give yourself flexibility later. And I think about that all the time. Because again, I'm so grateful for the career that I had. But I'm also so grateful that I get this opportunity with them now. And I just keep thinking my son will have his license in a year, which is crazy. But then he'll start driving and I'm just going to cherish the moments now.

48:59Jamie Trickett:Well, Jamie, thank you so much for taking the time to come on Real Estate Rookie today. We had a wonderful time with you. And thank you so much for sharing your journey, the lessons you've learned and your experience so far. Where can people reach out to you and find out more information about your journey? Absolutely. Well, first, thank you guys so much for all you do. I truly mean it from the bottom of my heart. The content is awesome. You guys are just great. I can be found at jamietrickett, two Ts at the end, dot com or info at jamietrickett. And I'm on Instagram. So thank you so much. This has been fabulous.

49:37Jamie Trickett:Yes. Thank you so much for coming on. I'm Ashley. He's Tony. And we'll see you guys on the next episode of Real Estate Rookie.

49:45Real Estate Rookie: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 need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener.

50:04Jamie Trickett: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.

50:16Real Estate Rookie: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.