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

Ashley:
She ran product 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 going to make me cry.

Tony:
Today’s guest, Jamie Trickett, walked away from the financial service 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 minded portfolio can help you walk away from your day job, this is yours.

Ashley:
This is The Real Estate Roofie Podcast. I’m Ashley Kerr.

Tony:
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.

Jamie:
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.

Tony:
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.

Ashley:
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. Let’s say on a Tuesday morning, what did the daily grind feel like from the inside?

Jamie:
Absolutely. So typically I would be running around like crazy in the morning out the door before my kids would 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 I really enjoyed my career, but I was missing my boys. So I wouldn’t see them really during the week. I’d be out before they were up and get home 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.

Ashley:
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?

Jamie:
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.

Tony:
For a lot of people, Jamie, this is what they work up toward, is exactly what you had. And I had a similar experience in my last WT job as well. I think I was 26 years old when I started working at Tesla. And it was just this life-changing experience, had all this responsibility. Then I got promoted, got these fancy titles and all these bonuses. But much like you, it’s like, man, the majority of my day was dedicated toward this thing. And then even when I wasn’t there, there was still just this mental drag of transitioning out of senior manager Tony into Tony at home and dad and all those things. So it was hard to feel fully present. Was there a moment when you realized, “Man, I think something has to shift?”

Jamie:
Yeah. 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 three o’clock I was back in work mode. 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 am 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, 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 hunts 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? Where are my priorities? So there’s just a culmination of things that were happening that made me just pause to figure out what was the point of all of it.

Ashley:
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 kind of walk us through what became the plan? How did you formulate a plan to actually get out of working your job?

Jamie:
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 purchased 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 2022. And so that 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.

Tony:
Jimi, 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 were listening is the first thing you said was your son saying, “Hey, I wish there were two of you. ” Going to the school and you being questioned about who you are because you hadn’t been there and getting a glimpse of what life might look like when you have that opportunity to stay home. I think for a lot of folks that are listening, 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.
It’s like, “Hey, this is the trade off for the success that I’ve been able to accumulate is that it does come at maybe the cost of time at home.” A lot of people just accept that. What was it for you that made you turn that notion on its head and say there actually is a better path? Because I think for a lot of people, they can resonate with the feeling of like, “Man, 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?

Jamie:
Yeah, I guess a couple of things I felt like I had a deadline, 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 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 my real estate portfolio 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.

Tony:
Jamie, for a lot of people, I think it’s the fear of what happens afterward that holds them back. And even though you weren’t jumping 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?

Jamie:
” It’s funny that you say that. That’s actually the saying that we have in our houses, 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. So I had been fortunate enough to put some money aside to make some investments, 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.

Tony:
And Jeremy, there’s a lot of parallels between your transition and mind where it’s like saying we had saved up a lot of cash and 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 can still go out and kind of rebuild my career if I need to. I’m pretty good as an employee in this workspace and I know that if I’m back in that position that I’ll probably do a good job and be able to climb another corporate ladder. So 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 had at least tried and there’s no regret around not having tried and that’s what would really gave us the motivation to double down and bet on ourselves is like, we can live with that worst case scenario.

Jamie:
Exactly.

Ashley:
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 five properties into a full W2 replacement. We’ll be right back. 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?

Jamie:
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. 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.

Ashley:
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 to buy information. Here you are, you went, your first ever investment bought 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 BiggerPockets yet and they’re not overwhelmed with consumption of all of this data that is available.
So not saying to not do your research and everyone still listen to this podcast, but you have to find a way to work over that hurdle and to navigate yourself to stay focused on what you’re doing. 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 strategy and you have to really stay focused.

Tony:
But Asher, 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 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 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 strategy that makes the most sense for you. Don’t worry about how you’re going to analyze and do all this other … Just, “Hey, what strategy actually aligns best with what it is that I want to do? ” And just focus only, you skip over all the podcast episodes that aren’t talking about the strategy. 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 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 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? 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, 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?

Jamie:
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 just like everything up and down, I now am focused on STRs.
I truly enjoy them. It might not be what I do forever, but that is the area or 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.

Tony:
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? Yeah.

Jamie:
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 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 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, that 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 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.

Ashley:
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 depreciated over, what is it, 39 years, 37 and a half years?

Jamie:
Or 27 and 39, yeah, depending.

Ashley:
Then you have your other bucket of like fixtures and furnishings, things like that. So they go in and like count the windows, 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, 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?

Jamie:
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. 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 a hundred percent bonus depreciation at the time because I had a 2022, 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.
Other people would do different things, but I am in the growth phase, so I just reinvested it into other properties.

Tony:
Jamie, I just want to clarify for the listeners, when you say you got back over six figures, logistically, what does that actually look like? Is it once you do the cost seg, you just immediately get this check back for 100K or how are you actually getting that money back?

Jamie:
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?”

Tony:
And I just wanted to highlight that for the listeners that when we talk about the cost segregation studies and bonus depreciation and kind of getting that tax benefit back or 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. But what you laid out though, Jamie, of buying a property, doing the cost segregation study, leveraging bonus depreciation, 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 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.

Ashley:
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?

Jamie:
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 cashflow, it’s tax savings, it’s appreciation. And then it’s the equity for renters, whether it’s long-term or short-term guests paying down the principle.

Ashley:
Now, Jamie, I want to compare a lot of investors are focused on cashflow. 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 cashflow. So what are your properties cash flowing? Because is it a ton of money where you’re getting both or is it kind of evening out?

Jamie:
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. But so from a gross perspective on the four properties, I did just close on a new property the other day.

Tony:
Oh, congrats. There we go, Jamie.

Jamie:
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.

Ashley:
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.

Jamie:
Exactly. So I mean, it definitely gave me confidence that 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 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 the long term are more stable, some are more appreciation place, the short term rentals are more cashflow place. 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.

Tony:
You’re doing all the things, Jamie. I love that. But I want to talk a litle bit more 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’ve?

Jamie:
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 That 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 with 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 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. The first property, I just kept an Excel spreadsheet and hopefully I would make sure that I accounted all my expenses, but who knows? 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, 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 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.

Tony:
Well, Jamie, you made the numbers work, but building a real estate business from scratch alone after years in 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. All right. 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 Jamie, you came from a big corporate team, then suddenly it’s just you, 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 and how did you work through that when you first made the transition?

Jamie:
Isolation is not too strong of a word. It was lonely. 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 BiggerPocket 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 realized that I was. So I have tried to join communities and it’s really helped 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.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 help you learn and people are willing to offer to share their experiences.

Ashley:
Now, Jamie, you joke 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, 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 not think about your business too.

Jamie:
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 paying a bill when it came in. I had no structure. So I very quickly determined, okay, there’s certain times that I’m going to do thought work and just try and block out three hours and undistracted hours to focus on what I needed to do. There’s times to 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 got a quick workout in and just sat and locked in and got the work done while they were at school versus sometimes 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.

Tony:
Jamie, talk to me really quickly about time blocking. 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?

Jamie:
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, maybe not harder. But somebody would ask me something and I would drop whatever and do a carpool or do this or do that. And so what I do now is I have dedicated days. So whether it be 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, are the tasks daily, weekly, or monthly, somewhere quarterly. 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.
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 financial review till tomorrow or next week and make those decisions?

Ashley:
And you joke that even if it’s just a meeting of one, but sitting down and making time for that stuff is so important. 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 it’s coming in. ” But actually sitting down and going through every single line item, looking at your financial reports, seeing your bank statements, things like that is still so important even if you are the person of one 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 added up.

Tony:
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 are listening. They got that return to office notification, so they’re maybe listening to this at their cubicle right now. What does an average week look like for you and do you feel like you’ve actually been able to accomplish what that original goal was?

Jamie:
Absolutely. My focus is my kids in the morning, 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? The importance of what kind of insurance do you have or 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 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 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, have time with my husband and my friends.
So I definitely feel very fortunate and grateful that I took this leap.

Ashley:
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 during COVID, my kids attended private school and they had to be driven and I had that mindset of, “Ugh, 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 have to drive and I feel like it’s an inconvenience.” And he’s like, “How many parents get that time in the morning with their kid? We talk about this, we sing songs and stuff.” And ever since then it just reframed my 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 interesting how just you reframe your mindset can really change how you perceive things in life.

Jamie:
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 afterschool 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’s your day? How’s your day? What happens 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. 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. 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.

Ashley:
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?

Jamie:
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 jamietricittwsattheend.com or info@jamietric and I’m on Instagram. So thank you so much. This has been fabulous.

Ashley:
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 Brookie.