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- [00:01]
A
She ran products for a Wall street trading platform. Six figures, corner office career, the kind of job your parents brag about. But every day she spent three hours in a car, and by the time she walked through the door, her boys were already in bed. Then she did the math on something that had nothing to do with finance. She only gets 18 summers with her kids before they leave. She'd already burned through several of them. This is gonna make me cry.
- [00:27]
B
Today's guest, Jamie Trickett, walked away from the financial services industry and replaced her income with just five rental properties. Five. And today she's breaking down exactly how she structured that portfolio, why she mixes both short term and long term rentals, and what her product management brain taught her about running a real estate portfolio like a business. So if you've ever wondered how a small but mighty portfolio can help you walk away from your day job, this is yours.
- [00:57]
A
This is the real Estate Rookie Pot podcast. I'm Ashley Kerr.
- [01:00]
B
And I'm Tony J. Robinson. Let's give a big warm welcome to Jamie. Jamie, thank you for joining us on the podcast today.
- [01:05]
C
Thank you guys so much for having me. It is a huge honor to be here with you both. Huge fan and I've probably listened to every single podcast you've put up, maybe some multiple times.
- [01:16]
B
And. And now you get to give back to the rookie audience, which is like our favorite type of guest is the people who come back and make it full circle.
- [01:22]
A
Well, Jamie, we are so excited to have you also. So let's start kind of at the beginning here. You were head of product management for a trading platform. You had a senior title, strong income, and a career most people would never walk away from, but paint the picture of what life was actually like. Like, let's say on a Tuesday morning. What did the daily grind feel like from the inside?
- [01:46]
C
Absolutely. So typically I would be running around like crazy in the morning out the door before my kids were probably even up. Once I got to work, I enjoyed my career so much. I was in foreign exchange trading, designing platforms for 18 years, but financial services for 25. I still don't know how that math actually works out, but so. But I really enjoyed my career, but I was missing my boy, so I wouldn't see them really during the week. I'd be out before they were up and get home. And at the end of the day, rushing around, get ready for dinner, homework, and just felt like I was literally Gumby, just running and rushing constantly.
- [02:32]
A
And during that time, did you ever think that you would find something else or retire early or transition or did you just think this is how life is and I have to get through it?
- [02:44]
C
Yeah, honestly, a great question. It was actually one of my sons who had said years before, mom, I wish there were two of you. He said, I wish there was one that went to work and one that stayed home. And I just thought, wow, okay. And we're very fortunate. We had an incredible nanny who was with us for 10 years and she's still a dear friend, their aunt. But I just thought this was the normal, that this is what I had to do to sacrifice for my family. And again, I enjoyed what I did, but I just thought that was it, this is how it had to be.
- [03:18]
B
Was, you know, for, for a lot of people, Jamie, like this, this is what they work up toward. Right? Is, is, is exactly what you had. And I had a similar experience my last WT job as well. I was, I think I was 26 years old when I started working at Tesla. And like, it was just this like life changing experience. Had all this responsibility. Then I got promoted, got these fancy titles, all these bonuses. But much like you, it's like, man, the majority of my, my day was dedicated toward this thing. And then even when I wasn't there, there was still just like this mental drag of like transitioning out of, you know, senior manager Tony into Tony at home and dad and all those things. So it was, it was, it was hard to feel fully present. Was, was there a moment when you realized, like, man, I. I think something has to shift?
- [04:01]
C
Yeah. You know, you mentioned about being present and I definitely struggled with that. I think my priorities were work, unfortunately, and then my children, my family, which is hard to admit, but it was always in the back of my mind. So even when they were trying to tell me something, I was thinking about what presentation did I have, what meeting, what deliverable. And I wasn't focused on what was happening or being able to enjoy the moment. Everybody knew Sunday at 3 o' clock, I was back in work mode. There was just. Weekend was over for me and I was refocused. But my turning point actually was Covid and partly. I know it was really difficult for so many people, but I was fortunate to actually be able to work from home. Our nanny became part of our unit and so she was here taking care of the boys, which was incredible. But I got the little moments. I got the boys coming in to tell me that they saw something outside or they learned something new or just to give me a hug if I wasn't on the phone. And I Thought, wow, what am I doing all this for? Because I almost, I'm embarrassed to say, but I didn't even realize the moments that I was missing. I would get updates and just think, okay, that's great, and onto the next, right? Because I was rushing constantly. But being able to go for a walk with them or go ride the bike in the afternoon was just. Those little hats were actually pretty awesome, too, during the day. So the other piece was, there's a saying that with your kids, you only have 18 summers. And even for myself, I sometimes think 16. My son is now 15. And once they start driving, they say, it's just difficult. You don't get that time in the car. You don't get caught up. So for me, actually, the time was ticking, and I had a couple of funny episodes that would happen. I did bring my kids to school one day, and the administrator at the school actually stopped me and asked me who I was because they had never seen me. So I thought, wow, okay, what's happening? Like, where are my priorities? Right? So there's just a combination of things that were happening that made me just pause to figure out what was the point of all of it.
- [06:21]
A
So while all this is happening, in these realizations and these aha moments, did you ever think that real estate was going to be the tool, the vessel, to actually get you out of your job? Or were you thinking it was something else? Or, you know, kind of walk us through what became the plan. How did you formulate a plan to actually get out of working your job?
- [06:44]
C
Yeah, no, great question. So it's accidental, actually. So during COVID and when I had that extra time, I had started researching and daydreaming. What would I do when I retired in 20 years, or my husband and I when we would retire? And so we thought, oh, let's buy a property now. We'll have 20 years. We'll rent it out. It will help pay down the mortgage. And so when we're ready to retire, we'll have that equity built up, and this will be great. So I dove in and did a bunch of research on a property down in southern Florida near Sarasota, and purchase sight unseen. I had never even been to Sarasota, put an offer on the first property in this development, and we were off by $10,000. And I was being stubborn at the time, thinking, it's $10,000 in the grand scheme of things. I've learned that is not a big deal. So then what happened from there? There was new construction happening. And so in 2021, we were under contract and it closed in 2020. Started my whole thought process of, oh, how is this going to work at this point? I'm still thinking 20 years in the future, this is our retirement and this is great and we're starting to build. But it slowly started percolating in my head about all the properties and what it could do.
- [08:09]
B
Jimmy, I want to circle back to the first deal that you bought, but before that, just like you said, a few things that were so I think just like struck a chord with me and probably with so many other people who are listening is the first thing you said was, you know, your son saying, hey, I wish there were two of you, you know, going to the school and, you know, you being questioned about who you are because you hadn't been there and, and getting a glimpse of what life might look like, you know, when you have that opportunity to stay home. I think for a lot of folks that are listening, we, you know, especially those who have maybe climbed the corporate ladder and they have a certain level of responsibility at their job and there's a certain level of income that comes with that. We just kind of accept that that is what it is. You know, it's like, hey, this is the, the trade off for the success that I've been able to accumulate is that, that it does come at the, the, maybe the, the cost of time at home. A lot of people just accept that. What, like, what was it for you that made you kind of turn that notion on its head and say, there, there actually is a better path? Because I, I think for a lot of people, they can resonate with the feeling of like, man, it's, it sucks, but it's just like, man, this is how it has to be. What actually gave you the belief that that wasn't how it had to be?
- [09:20]
C
Yeah, I guess a couple of things. I felt like I had a deadline. So time, right? It is not a renewable resource and there's only so much time. The other thing is that when I did purchase this first property, I was fortunate enough. It was in 2021, 2022. The interest rates were quite low, so I had locked in a low rate I didn't even know at the time to negotiate, you know, an even lower rate buy down. I have learned that since. And so I was starting to cash flow a little bit of money there and thought, okay, I need to make a decision. I either need to bet on myself and continue to learn and build and grow what I would call, you know, my real estate portfolio or or continue down the path that I was on and just accept it. But after Covid and when work, like many corporations, they wanted everybody back in the office four to five days. And I couldn't imagine going back. I had a three hour commute every day, an hour to an hour and a half each way. It just wasn't something I was willing to give up time with my kids.
- [10:34]
B
Jamie, for a lot of people, they, I think it's the fear of what happens afterward that, that holds them back. And even though you weren't jumping, you know, off the deep end on day one, it was still kind of like in the back of your mind. How did you reconcile that fear of like, well, what if this doesn't work out?
- [10:50]
C
It's funny that you say that. That's actually the saying that we have in our house is what is the worst that could happen? And there's always a solution to every problem. It might not be the best solution unless it has to do with your health, really. There's always a way to solve the problem. So I thought I would go back to work. If I needed to go back to work, I would get multiple jobs. If I needed to get multiple jobs, we could cut back on so many things. And truthfully, because I'm data driven, we had a budget, and so we listed out all the things that we could cut out if need be. And if this didn't work, my husband's still working a W2. We had lived well below our means for a while. It's just how we have always operated. I had been fortunate enough to put some money aside to make some investments, so that was always there too. So I guess I was preparing unconsciously for a little bit. So it gave me a little bit of comfort because I also don't like risk. I don't want to take big risks. I didn't want to put my family in jeopardy. So it was very much a calculated risk.
- [12:00]
B
And Jamie, there's a lot of parallels between your transition and mine where it's like saying we had saved up a lot of cash and, you know, when I had this opportunity of either going back into the workforce or building our portfolio and betting on ourselves, we bet on ourselves. But it was the same conversation of like, okay, well, what is the worst case scenario? I'm young enough to where I, you know, I can still go out and kind of rebuild my career if I need to. I'm pretty good as, as a, as an employee in this workspace. And I know that if I'm back in that position that I'll, I'll probably do a good job and be able to climb another corporate ladder. It's like the worst case scenario is that I spend maybe a year or two trying this thing out. It doesn't work and I just go back to living some version of the life that I was living before. But at least at that point I would have the knowledge that I, I had at least tried. And there's no regret around not having tried. And, and that's what, what really gave us the motivation to double down and bet on ourselves. It's like we can live with that worst case scenario.
- [12:49]
C
Exactly.
- [12:50]
A
Now Jamie made the decision to bet on herself, but she didn't quit and wing it. She did what any good product manager would do. She built an exit plan. After the break, she'll walk us through how she turned just one five properties into a full W2 replacement. We'll be right back. When you first start something, whether it's a business, a side hustle, or even investing, it feels like you're doing 10 jobs at once. You're figuring out branding, setting things up, trying to get customers, and somehow keeping everything organized behind the scenes. That's where having the right platform actually changes the game for millions of businesses. That platform is Shopify. Shopify powers millions of businesses worldwide and handles about 10% of all E commerce in the U.S. it's built to help you manage everything in one place, from inventory and payments to analytics and growth. You can launch a store that actually looks professional using their ready to go templates and even use built in AI tools to write product descriptions or improve your listings. And when it comes to growth, Shopify helps you market like you've got a full team behind you with easy email and social campaigns to reach your customers wherever they are. Plus, if you ever get stuck, they've got 24. 7 support to help you figure it out. So so instead of juggling a bunch of disconnected tools, you can run your entire business from one platform and actually focus on growing it. It's time to turn those what ifs into with Shopify today. Sign up for your $1 per month trial today at shopify.com Rookie Go to shopify.com Rookie that's shopify.com Rookie Most investors
- [14:23]
D
spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy, and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims and traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning to steadily. They focus exclusively on landlords. Whether it's a single family rental, a Spur builders risk policy or midterm holiday guests, you get fast quotes, flexible coverage and protection for property damage, liability and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in minutes@biggerpockets.com landlordinsurance steadily landlord insurance designed for the modern investor. Most deals don't fall apart because of the numbers. They fall apart because of the financing. You find a property that cash flows, the deal makes sense. But then the lender looks at your personal income, your tax returns, your debt to income ratio, and suddenly the deal doesn't qualify. That's the disconnect. Because as investors, we're not buying based on our W2, we're buying based on the asset. That's why Host Financial offers DSCR loans designed for real estate investors where qualification is based prior to primarily on the property's income, not your personal finances. So no W2s, no tax returns and no DTI requirements. And with loan to value options up to 80 or even 85% on eligible deals, you can keep more capital available as you grow. If you're buying rentals, refinancing or scaling your portfolio, go to hostfinancial.com that's h o s t financial.com and see what you qualify for.
- [16:13]
A
Okay, welcome back. So Jamie knew she couldn't keep trading her time for a paycheck. But conviction doesn't pay the mortgage. Let's talk about how she actually built a portfolio that could replace a six figure finance salary with just five doors. Maybe take us back to your first deal in 2022. You're still working full time in financial services. This property that you bought down in Florida, had you started doing any research about real estate investing at that point? Or was it just you were kind of in your own little bubble and just going for it?
- [16:47]
C
I was definitely starting, not nearly like I have been the last couple of years. I don't think I had found bigger pockets yet. So that obviously changed my trajectory. But I had found this property. Like I said, I had locked in a low interest rate and I was pretty much outsourcing it. So I had a real estate agent who was renting it. Um, it's a 30 day rental, so it was an MTR or a midterm rental. I didn't even know what the term meant when we started, he would rent it to snowbirds four to six months a year, which was great. I would sit empty for a couple of months. I would pay someone to check it. And then I thought, wow, why don't I take this over and learn how to do this? So basically I took that property over and my thought was to grow the portfolio slowly. So every year since then I have purchased a new property because I was working just until two years ago. So this was two years before I even decided to leave work.
- [17:49]
A
So you said the research thing, I wanted to touch on that you hadn't done a ton of research. And I'm noticing this more and more, that the more information and knowledge you consume, the more people take longer to actually invest in real estate, that you're just so overwhelmed by information. Here you are, you went, your first ever impre your investment, bought it sight unseen in Florida. You get this idea, you implement it, you take action. Where so many people get stuck in this analysis paralysis because they are so over consumed with having so much access to different tools, strategies, research on real estate investing. So I'm not saying jump into real estate without doing your research and everything like that, but it is so interesting to me how the people who tend to just take action is because part of it is they haven't found bigger pockets yet and they're just, they're not overwhelmed with consumption of all of this data that is available. So not saying to not do your research and everyone's still listening to this podcast, but you have to find a way to work over that hurdle and to navigate yourself to like stay focused on what you're doing. Um, Tony and I just interviewed somebody who was talking about assisted living. We're like shiny object syndrome. How do we do this? Let's start on this. You know, and you have to, to, to really stay focused.
- [19:14]
B
But Ash, I think one concept that I learned early on that I felt like has really stuck with me and I've shared this in the podcast before. I actually learned this from a marketing podcast. There was this guy who was, you know, really successful business person in the marketing space and he talked about the idea of just in time learning. And it actually comes from like the production facility background where there's like just in time production, where you kind of move things through the warehouse at a pace where it's as soon as you finish, that's when it's needed at the next station. You don't have this big pile up of stuff from one station to the next. And it's the same Concept when you learn something is that sometimes we get overwhelmed because we have all of this information piled up that we can't actually execute on yet. But if we instead focus our attention on learning the things that allow us to take the immediate next step, that's how we can sometimes overcome that, that overwhelm that comes from all the information. So for the rookies that are listening, really focus the majority of your attention maybe first on the. The strategy that makes the most sense for you. Like, don't worry about how you're going to, you know, analyze and do all this other. Like, just focus. Hey, what strategy actually aligns best with what it is that I want to do? And just focus all. Like, only you skip over all the podcast episodes that aren't talking about the strategy. Right. And then once you've got the strategy dialed in, then focus on, okay, well, what is the first step of that strategy? A lot of times it's the market. Where am I actually going to do this, this strategy? So then all of your attention shifts from overall strategy to how do I pick a market? Whether it's long term, midterm flipping, apartment complexes, whatever it is, find content specifically around how to find the right market. And then, then it's the, how do you find the deal? How do you analyze? And it's how do you due diligence and underwriting and all those different things. Right. So, but if we can break down our education instead of it being this one big amorphous blob of information, how can we break it down into just in time, information that allows us to take that next step? So I know that's a lot, but, Jamie, like, coming back to you and your story, how did you personally overcome, I think, that information overload that gets so many rookies stuck from actually moving forward?
- [21:09]
C
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 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. 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 class that I enjoy. Even though I have a few other asset classes as well in the long term space.
- [22:20]
B
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?
- [22:35]
C
Yeah, again, I am risk averse mostly, so I wanted to have a bit of balance. I wanted some cash flow. I also didn't understand the tax benefits, if I'm being 100% honest at the beginning of this real estate journey. I had asked our CPA recently, a couple 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, no, they're not worth it, they're a waste of your money. And so I thought, wow, I've heard about it on bigger pockets. I kept listening. I went to go look it up and research and. And of course it was incredible. I did execute the cost segregation study. It was a huge tax savings. It actually allowed me to purchase one of my other properties, giving me the down payment for that.
- [23:28]
A
Jamie, I want to, 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 like, I invested for probably seven or eight years before I even knew what a cost segregation study was.
- [23:46]
C
So.
- [23:46]
A
So maybe just to like 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. A different bucket, I like to call it. So like the actual property itself, it's, you know, depreciated over, you know, what is it, 39 years? 37 and a half years or 27 and 39.
- [24:09]
C
Yeah, depending.
- [24:10]
A
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?
- [24:41]
C
So again, I didn't know about cost segregations until the last couple of years. 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 purchased, there wasn't 100% bonus depreciation at the time because I had a 20, 22, 23 and a 24 purchase. They were all different percentages. I was able to recoup $150,000. And so that was able to, like I said, I could reinvest it. You know, other people would do different things, but I am in the growth phase. So I just reinvested it into other properties.
- [25:50]
B
Jim, I just want to clarify for the listeners. When you say you got back over six figures, like, logistically, what does that, what does that actually look like? Like, is it, you know, once you do the cost egg, you just immediately get this check back for 100k or like, how do you, how are you actually getting that money back?
- [26:04]
C
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's just go back and make sure they did this right. So we sat down with accountant. We had changed to an accountant who's a bit more focused on real estate, who understood cost segregations. They walked us through the tax savings and we're like, this is great. What property am I going to buy now?
- [26:56]
B
And I just want to highlight that for the listeners that, like, when we talk about, you know, the, the cost segregation studies and bonus depreciation 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 a tax refund for whatever tax year it's associated with. So. But what you laid out though, Jamie, of, 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. And it just becomes this 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, all of the tax benefits and you're getting the cash flow and you're getting the appreciation. Which is why for high income earning W2 professionals, short term rentals are sometimes the best asset class to go after.
- [27:52]
A
And Jamie, did you file 2025 yet as to how much you're still from that first cost? You're because you didn't have 100% bonus depreciation. So this year will you have another huge cost savings?
- [28:04]
C
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. It's definitely something you have to. 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.
- [29:05]
A
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.
- [29:27]
C
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 bigger pockets.
- [29:41]
A
But.
- [29:41]
C
But. So from a gross perspective on the four properties, I did just close on a new property the other day.
- [29:47]
B
Oh, congrats. There we go, Jamie.
- [29:52]
C
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 bigger pockets, you guys, and the other bigger pockets 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.
- [30:26]
A
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 W2 job and how this all kind of all the pieces fit together for you to be able to leave and feel comfortable with that.
- [30:46]
C
Exactly. So, I mean, it definitely gave me confidence that, you know, I have the cash flow 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 rate, which is almost funny now to think about. 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, you know, the long term are more stable, some are more appreciation plays. The short term, rentals are more cash flow play. 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. And tomorrow morning I'm flying down to North Carolina to look at more properties.
- [32:25]
B
So you're, you're, you're doing all the things. Jamie, I love that. But I want to talk a little bit more. Right, because you have this, this role as, as a product manager. And I, I know my role as a W2 employee working in, you know, supply chain, distribution, people leadership, that's actually helped me a lot as an entrepreneur. So I'm curious, you know, you come from a world of financial models, you know, 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?
- [32:54]
C
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 2 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 a short term rental, I'm so fortunate. I have paired up with an incredible designer who is helping me like execute on that plan. 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 counted all my expenses. But who knows, right? I was trying to do the best. Now I've taught myself bookkeeping. 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 amount 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.
- [35:00]
B
Well, Jamie, you made the numbers work, but building a real estate business from scratch alone, after years on a corporate team, that's the part that nearly broke you. And after the break, you're going to be sharing with us what you do differently and the one career skill that turned out to be one of your biggest unfair advantages.
- [35:19]
D
Tax Season Reminder for all the real estate investors listening, if you own rental properties, short term rentals, commercial buildings, basically anything that's not your primary residence, you need to know about Cost Segregation. It's an IRS compliance strategy that lets you accelerate depreciation on your properties, which means you're paying less in taxes this year and keeping more cash in your pocket for your next deal. Cost Segregation guys is the go to firm having done over 12,000 of these studies with 500 million in total depreciation identified. Head to costsegregationguys.com bp to get a free proposal and see your potential tax savings. You've upgraded how to buy properties, but did your insurance get the memo? When investors start scaling, insurance can't be an afterthought. Most policies were designed for a single property, not multiple rentals, LLC ownership, short term stays, or properties mid rehab. That's where blind spots can creep in. NREG works exclusively with real estate investors. They understand portfolios, how risk compounds as you grow, and why insurance should protect your upside, not just the checkbox. One uncovered claim can undo years of progress before your next acquisition, review your insurance Talk to NREG and get investor specific coverage from specialists who actually understand real estate@nreg.com BPPOD that's n r e I g.com BPPOD billion dollar investors don't typically park their cash in high yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors, private credit. Now the same passive income strategy is available to investors of all sizes thanks to the Fundrise Income Fund, which is more than $600 million invested and a 7.97% distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar average asset class in the last few years. Visit fundrise.com pockets to invest in the Fundrise Income Fund in just minutes. The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results. Current distribution rate as of 1231 2025. Carefully consider the investment material before investing, including objectives, risks, charges and expenses. This and other information can be found in the Income funds prospectus@fundrise.com income. This is a paid advertisement. People love to call real estate passive income, which is interesting because most of the investors I know are very busy. Busy finding deals, busy managing teams, busy worrying they picked the wrong market. Rent to Retirement flips that model. They help investors buy turnkey new construction homes, often 10% below market value, in top rental markets across the country. Their local teams handle the build, the property management and the details so you don't have to. In some cases, Investors even receive 50 to 75% of their down payment back at closing. And there are interest rates as low as 3.75%. They've been trusted partners with BiggerPockets for over a decade. And if you want to learn more, visit biggerpockets.com retirement all right, so we've
- [38:18]
B
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 is, might be too strong for, but what did that feeling of being on your own feel like and how did you work through that when you first made the transition?
- [38:51]
C
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 non stop. I am on biggerpocket's website looking at every single market data that you offer or on the forums, right, the Bigger Pocket 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 and I realize 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, 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.
- [40:08]
A
Now. Jimmy, you joked that when you first left to finance, you were told by people that you were retired, 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.
- [40:37]
C
Exactly. And another mistake I learned was I did not time block. I did not hold a schedule. I just let anybody whim that they needed, I would help them or I would be constantly, you know, paying a bill when it came in. 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, 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. I really just was able to take control of my schedule. So it was incredibly helpful.
- [41:37]
B
Jamie, talk. Talk to me really quickly about time blocking. Like, like, what is that concept? And, and why have you found that as a valuable tool for you now that you're. You're a solo running this business?
- [41:46]
C
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, I 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, 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?
- [42:54]
A
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. 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, yeah, I know I paid the bills, so I know what's going out. I collect the rental income, so I know it's coming in. But actually, sitting down and going through every single line item, looking at your financial report, 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,
- [43:39]
B
you know, But, Jimmy, you did all this because you wanted some semblance of. Of time, freedom and. And that presence back with your family. So what does an average week look like for you now? Kind of. Kind of paint the picture for the Rickies who are listening. They got that return to office notification, so they're maybe listening to this at their cubicle right now. What. What is an average week kind of look like for you? And do you feel like you've actually been able to accomplish with that? That original goal was absolutely.
- [44:05]
C
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. You know, 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. 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 W2, hand over my forms and never thought about it. I never thought about all the different facets of it, but. 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. I am always looking at properties and opportunities, but I'm also trying to network as well. Again, being in the communities, being with the, 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 mom Uber in the afternoon, but again, I wouldn't trade it for the world, have time with my husband and my friends. So I definitely feel very fortunate and grateful that I took this leap.
- [45:57]
A
And I think it does kind of change your mindset. Instead of around, oh, I got to drive the kids here. They have so many sporting events. I have to drive them to school because my 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, like, I have to drive and like, I feel like it's an inconvenience. And he's like, like, how many parents get that time in the morning with their kid? Like, we talk about this, you know, we sing songs and stuff. And ever 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.
- [46:57]
C
Exactly, exactly. And I think so. My boys don't even have an option for a bus and their carpool is 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, 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, like hours. 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 year, which is crazy, but then he'll start driving and I will. I'm just going to cherish the moments now.
- [48:30]
A
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?
- [48:46]
C
Absolutely. Well, first, thank you guys so much for all you do. I truly mean it from the bottom of my heart. Heart. The content is awesome. You guys are just great. My I can be found at jamie tricket2t's@the end.com or info Amy Trickett and I'm on Instagram so thank you so much. This has been fabulous.
- [49:08]
A
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.
- [49:16]
B
Hey Rickies, 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
- [49:35]
A
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.
- [49:47]
B
So head over to biggerpockets.com guest if you want to be a part of our show again. That's biggerpockets.com guest and we'd love to have you on.