$6,000/Month Cash Flow from 4 Rentals in 2 Years (Without a Ton of Money)

Making $6,000 in monthly cash flowHey, rookies, mortgage rates are falling, but the uncertainty of the economy is slowing. Real estate sales opportunity is still here, but getting specific with your strategy is key to finding a good deal.Our guest today built a major cash flowing real estate business in just two years with more growth opportunities on the horizon. Using her superpower of networking, she assembled the right financial partners, informed a specific roadmap to reach financial freedom. Get ready to take notes. There’s a lot to learn in today’s episode.This is the Real Estate Rookie podcast. And I’m Ashley Kehr.And I’m Tony j Robinson and welcome to the show. Jamie, thank you for joining us today.Thanks so much for having me,Jamie. You have so many amazing stories that we’re going to get into, but first could you walk us through on a high level your journey from that first property in Philadelphia to your current portfolio of four properties in just two years?Sure. So I bought my first investment property in January, 2023, closed on it and a few days later actually got my first arbitrage a few doors down, so became hooked a little and then from there realized that I had a primary residence that I wasn’t house hacking and so I needed to do that as well. So I got kind of a few rentals fairly quickly. I ended up giving up my arbitrage, but after that bought another property in New Orleans, which I think we’ll kind of touch on later as an MTR. And then late last year bought a property in a new market in Indiana, which I did a lot of research on and really found which market in the US works best for my strategy. And so that one’s been a lot of fun as well. So really went from Philly to a few different other markets, but I’m currently utilizing the MTR strategy for all four.Well, Jamie, I can already tell we’re going to learn a lot of different things from you, from market selection, deal analysis, strategy choice, but you used the word arbitrage. Can you explain what arbitrage is and how you implemented that into your real estate investing journey?Sure. So arbitrage is essentially renting an apartment or house and then subleasing it or renting it out at a higher rate to another party. And so essentially I worked at the time in commercial real estate and did a lot of research in the multifamily industry. And so my first property was in Philadelphia and I knew and brought it in January I think, which I mentioned and I knew in January and Philadelphia properties have a lot of vacancy because it’s cold and because no one wants to move to Philadelphia in January. And so I kind of essentially door knocked, but they were large apartment buildings. So I apartment knocked and just went building to building, told them I plan to rent to tribal medical professionals, corporate professionals, and basically just went around to different buildings. And so one told me yes, and so from there I had quick numbers on what I thought I could rent it out for because at this time I’m still furnishing the one I just bought, so I don’t really know my right yet. And got a small studio apartment but was in a great area in Philly, which I’ll just say area and location in Philly is very important and so it’s garage parking. And so having those amenities really just kind of helped me really be able to make the most out of that arbitrage.So Jamie, I mean first just super impressive on your end I think to go door knocking to all these different apartments. Did you have a background in door to door sales or what gave you the confidence to just kind go out there and start hitting the pavement in that way?No, not at all. I think my confidence was more so of understanding the numbers and I will say I did some kind of insider research and had access to CoStar, which for those who don’t know is a huge commercial real estate marketplace. You can pull vacancy rates, occupancy rates, rental rates for all types of commercial real estate assets. And so I could basically pull the numbers for the vacancy rate for different apartment buildings and was able to see the one I ended up or the few that I ended up kind of targeting first were fairly new build and had under 40% occupancy. And so coming to them saying, Hey, I’m willing to sign a 12 month lease or a 14 month lease or I’m willing to move in tomorrow, and just using different negotiation tactics helped me get in. Actually when I first went, I asked for six months of free rent and they came back at four, so I didn’t know I was going to get any, but I was like six months and they kind of talked among themselves and I was like, well, four works. And so it’s just once having the four months obviously really helped my numbers. And so once it was time to kind of renew the rate, the numbers no longer worked, but it was definitely great while it lasted,I’m starting to rethink my life choices. Maybe I need to go and find new development and negotiate free months of rent and just every year move to a new development and only pay for it for half the year.I had kind of insider information and I knew from we would do originate commercial loans. We did a lot of preferred equity, which was kind of second position, senior debt to large multifamily. And I knew developers, they’re just trying to get basically people in there so they can refinance and develop something else. So I cannot use that to my advantage.I’m so impressed by how you were taking all this information to use it to your advantage to create a strategy for yourself.ThankYou. And I love the idea of different leverage points in negotiation like, hey, I’ll move in tomorrow. I think that’s a really, really unique strategy to get them to play nice with you. You start to build your portfolio and just walk through the 30,000 view again. So you buy a property, you get the arbitrage, you exit the arbitrage. What exactly does the current portfolio look like today and what all markets are you currently in?Yes, so I am currently in four different markets, Phil, Pennsylvania, which is where my first property that I bought was. Also the arbitrage that I’ve since exited is I have a property right outside of DC in Northern Virginia that was a house hack, but I recently moved out of, turned into a whole home MTR, also have a MTR in New Orleans, Louisiana. And then my newest one is right outside of Indianapolis, Indiana.Now something you mentioned, because I’m just curious how this plays into the story, but you said that you worked in preferred equity or private equity. Was that your day job working in that or what was that line of work exactly?Yeah, so it was my day job and so essentially when I would say interest rates started to increase even I would say the end of 2022, before I would say residential investors started kind of seeing the pain points in commercial real estate, 1% increase on a $40 million property is a lot. And so then there was a deal that I worked on where the bank about a week before closing said instead of lending at 75% LTV or loan to loan to value, which meant basically it was 25% of equity that had to be raised in the deal, they would only lend at 50% and I think that deal was maybe 50 million. And so they’re asking us to come up what’s an additional 25 million or what is that like over 10 million in a week? And so basically the company I was working for at the time really started doing preferred equity, which essentially was coming in as equity, but it was a second kind of a secondary lien. So I think the same way people might use private money and a residential deal, we would come in and offer for a really high rate. The last deal that I originated in 2023 before I left my W2 was at 15%. And obviously interest rates kept going up from there. And so it was more flexible because we weren’t a bank I think definitely helped me catapult into where I am today and how I look at different investments.And when you transitioned out of your W2 job, you took on co-hosting, is that correct?Yes.Yeah. So tell us why you started that business and how that’s going.I started the co-hosting business when I finished, when I quit my job because to be honest, I didn’t think of how am I going to earn active income. And so as all investors know, you might have amazing cashflow. I would tell you I do have great steady cashflow, but one hot water heater or one month of vacancy can take that away. And so I started co-hosting as a way to see which markets and kind of test out different markets that I would want to invest in because while arbitrage is a generally low cost way to get into a midterm rental, it’s not free. You still have to pay security deposits first, sometimes last month’s rent, and there’s still an initial investment required where I actually got paid to set up in different markets. And so that was a way how I grew my active income.
Another thing I was able to qualify for real estate professional status, which is definitely a key and I only a game changer to me and my husband’s wealth building strategy. Also, I was able to see that I don’t love managing midterm rentals in a lot of different markets. I did that for about a year. I had a team of VAs who was pretty much doing most of it, but I like to do, and I learned this from my W2 days, an annual review of just how is the business doing, how is my time best spent? How is each investment doing? And my co-hosting properties were netting me a few hundred where I have, and we’ll talk about a little later in my portfolio net’s me a few thousand on average per property. And so I saw that for me it was best use for my time to stop co-hosting and focus on raising private money, which is something I already started doing to grow my portfolio because then from there I was able to cashflow more and it’s also less stress because I’m answering to myself versus someone else. And then also I’m able to benefit from the tax strategies as well. So pivoted from that. I think for me, it’s funny, I kind of consider it an internship even though it was my full business, but I think for me, in order to see if I want to do something, I have to do it at scale and test it out. And so it was definitely great to show me markets that are good and markets that are bad for MTR and then also help me identify what makes the best midterm rental market.Yeah. Well Jamie, you seem like just a complete hustler to go from, Hey, I’m going to do this deal, I’m going to do this arbitrage, I’m knocking on the doors. Now you’re setting up the CO and business. And I think far and above and beyond just the skills and the strategies we’ll talk about today, I hope one of the things that the rookies take away is that you just have a very strong bias for action. And I’m sure that’s helped lead to a lot of your success. So we want to hear more Jamie about your investment strategy and how it’s evolved. And I hear you’ve got a little bit of a superpower when it comes to networking, so we want to break that down as well. But first we’re going to take a quick break to hear a word from today’s show sponsors.
Alright, so let’s get back to the show with Jamie. So Jamie, I hear that one of your superpowers is your ability to network. So can you share with us how you networked your way into finding some of these money partners, some of these financial partners to help you fuel your growth? I think for a lot of rookies that are listening, the biggest challenge is, well, where am I going to get the funds maybe after my first deal or my second deal to keep scaling. And it sounds like you solved that problem. So what is the secret? How can I network define all these folks that have the capital?Yeah, I would say one, it really goes from knowing your investment strategy. And so for me, knowing that for my investment strategy, I need private money for three to five years, which isn’t typical, but knowing this, I’m able to back into, okay, now who is my ideal lender? The same way you have an ideal tenant, you might have an ideal property, a buy box. I like having my ideal lender and for me that’s personally someone who worked a W2 job that they left and they still might be W2 now, but really they have money but not time. And I like to work with people who have, I say left there a prior W2 job because generally they have funds in a 401k or IRA or another investment vehicle that can be transferred to a self-directed IRA and self-directed IRAs allow, basically it allows you to self direct the investment to anything.
So you can self direct it to Tony because he needs 10 bucks or you can self direct it to me or you can self direct it for different things. And so I’ve seen that those lenders or more flexible with a three to five year term because it’s retirement money that they can’t touch anyway. And so with that, I would go to real estate investment meetups conferences and I’m really looking for that specific person. And then also too, just sharing my journey on social media. One of my repeat lenders has actually been from social media and we’ve never met in person, but we’ve talked, she was actually a client of mine with some services I offer. She came to me to learn more about midterm rentals, realized that she doesn’t have time for it, and then decided to invest with me.Jim, you said that one of the other places that you’ve gone is to local meetups and I think that’s just so accessible for most rookies because not everyone’s going to want to hop in front of the camera and make content for social, which I get, but the meetup is something or the local events or the big conferences, those are things that are accessible to everyone. So you said that you had an idea of who you wanted to go after or who, I shouldn’t say go after who you wanted to connect with, but once you found those folks, what were you actually saying to open up that dialogue? How do you go from, Hey, we’re strangers meeting at this meetup to hey, you’re now potentially funding a deal that I’ve got?Yeah, I think there’s key words that now that I’ve raised a lot of money that I hear, and usually it’s like, oh, I’ve always wanted to invest in real estate. And usually the but is time, right? Or it could be, oh, but I only have $25,000 and I’m in California, which is not going to go really far. And so hearing those things that they’re interested in real estate, I always just let them know that there’s ways to invest in real estate without actually being the landlord. And I was like, and doing all the hard work like I do. And so then if they engage in the conversation, then I’ll just start to let them know that was my last investment. I worked with someone who lended the money and who was the bank who got a fixed return. And then I’m able to operate the property and I take on the risk where the lender gets a fixed return.
And I explain to them a lot of times, obviously it depends, it’s different if we’re at a meetup where we might only have a few minutes versus a conference where we can kind of step aside. But my goal is always to have a separate conversation because I like to have at least three different contact methods before working with someone and starting to negotiate rates because even though this person isn’t a debt partner, not an equity partner who you’re, but maybe talking to continuously, you still are a partnering, you’re still partnering and you don’t want someone and you want to understand it’s like are they going to ask for the money back? Is this their last 50,000? Because you definitely don’t want that. And so I think just kind of asking questions but also just times I’ll even bring up, oh, I worked with someone who was kind of like you and lend this money and just kind of giving the example.
And when someone starts asking questions, I think that’s when you can really just say, Hey, well let’s schedule a call. No pressure to talk about it. And I’ve also started doing webinars where I call ’em how to passively invest in real estate and I don’t just talk about investing with me. I’ll talk about how to invest in res, how to invest in reefs and different investment avenues. Then obviously I want them to invest with me. But I think just even having those webinars that are low pressure and just telling someone, Hey, if you want to learn more, just come to my webinar. No pressure. Think people sometimes like that better than hopping on a one-to-one call where they’re kind of nervous to be sold to. That’s kind of a low pressure way to get the information without having to talk one-on-one.Now Jamie, it seems like you’ve pretty much stuck to your niche of medium term rentals. What about your locations? You mentioned a couple different cities. What is kind of your geographical niche of where you actually want to invest in?That’s a great question. All over the US right now, don’t recommend that by the way, Indiana. So I will say that I’m the one, I think Tony said before I take a quick action, and I think part of that is deciding when it’s time to pivot. And so with Philadelphia bought in Philly two weeks later, the market started regulating short-term rentals. And essentially if the property wasn’t owner occupied, it couldn’t be a short-term rental. And so overnight, I’m kind of a data nerd, so I track different data points because for midterm rentals there aren’t the same, it’s not the same data out there that it is for short term rentals. There’s no air DNA and things like that. And so overnight, I track the percentage of properties on the OTAs, the online travel agencies, which are Airbnb, vrbo that are MTRs or that have a 30 plus day minimum. And so that number overnight went from 12% to 30%, which if you look at 30%, that’s one in every three properties on Airbnb is a midterm rental.
One in every three travelers is not a midterm traveler to Philly. There’s definitely going to be more short-term demand. Things like that have showed me, okay, it is time to pivot. I shouldn’t keep buying in this market even though if my property is doing great, it’s definitely time to look at a new market. For me, I’m looking at Indiana right now mostly for, I’ve done a lot of research on different markets, especially since I think I’m, I’m not scared to go to different markets, but it’s been one having solid, I like having medical demand. So that’s from hospitals, that’s from travel. Medical professionals can be a MTR tenant, not my usually ideal MTR tenant because my properties are up to four bedrooms, so they typically needed something smaller. But even if there’s hospitals that have surgery centers and things like that, you’ll have travelers who need to come in the area for long periods of time for let’s say medical reasons.
Also, I like to have education, so this is schools, universities I’ve housed everything from, I housed a couple who were professors at UPenn and Pennsylvania and Philly, and they were from the UK who you never think that teachers and professors come from different countries. So I like having that education demand because no matter what, you’re always going to have your midterm traveler from students. And then third, I like to have a strong corporate demand. Corporate is usually where the most money is. And so I chose Indiana, basically. I chose Indiana because I went to Indianapolis to a meetup and told everyone I wanted to do, and they just started shouting markets and like, oh, go to this place. And someplace was like, no, that’s all corn fields. And so I heard all these markets and I was there for a week by myself, rented a car, and I drove to all these markets.
If I drove to the market, I remember one market I got there and I’m like, there’s no way. I just passed it. It was one or two houses, I don’t think they’ll need to get out, but some markets. I went and went to the chamber of commerce, went to the city planning and zoning to learn what does the city have. And so the city that I invested in, it’s in Boone County, Indiana. Basically I learned that Eli Lilly is investing 4.5 billion in this small town. Meta just committed 800 million to this small town. But another thing is, which I think is key for MTR operators and even STR operators is it’s near Indianapolis, so it’s 30 minutes outside of Indianapolis, which means I can still hire Indianapolis Labor because when I was co-hosting, there was times I was in markets that were small but so small that the labor pool was so small.
So if that one cleaner decide she’s not working today, well, you can’t get your property cleaned. And so for me, it checked all the boxes and then I just started making offers and then ended up getting something a few months later. But I think for me, kind of all those aspects of demand, and especially when there’s one huge demand, like the market I invested in, there’s construction workers who, the construction project that’s going on now where Eli Lilly invested is going on through beginning of 2028, which means there’s going to be construction crews needing housing through 2028, and it took me about three weeks to get a construction crew and they just keep extending and extending and extending because they’re finding work, they have housing, and so it’s a win-win. So I’m trying to buy more there.Jamie, I just want, you’re saying it’s so common and collected, but you’re describing a massive amount of effort. You just said, I went and I spent a week in this market that I was thinking about investing into. I went to this meetup, I drove around, I did all of this research beforehand, and I think it’s so easy to sensationalize the end result of, Hey, you’re at X dollars in cashflow per month with these many properties, but then we overlook everything that you just said about the work that you put into it. So I know I keep harping on the same fact, but I think it’s so important for Ricks to understand that the work that you put into it directly indicates the kind of results you’re going to get. And I’m just super impressed by how much work you put into it. But I do have one follow-up question. How the heck did you know about meta and about Eli Lilly coming into this small town? You said Bloomfield, Indiana, never heard of it before. So how did you get that inside scoop?Her name is Jennifer. I don’t think she listens to this, but she is my contact with the city and planning department. So the first time I’m driving through, I stop in, and this is before I even knew I was going to invest here, and I just go in and just tell her, Hey, I’m an investor. I like working with businesses who need housing. And she was like, whoa, did you know that? At the time, I think Eli Lilly was only but investing 2 billion, and she’s like investing 2 billion and there’s construction workers sleeping in their car. And I was like, really? Tell me more. And so she’s telling me all about it and then we exchange emails and I will say I do email Jennifer at least once a month, sometimes once a week just to kind of keep that contact. I go usually once every three months.
I think especially it’s a small town where showing my face is really important and it really building trust in everything with vendors has helped by being there. So just keeping that connection. She tells me everything. When it went from 2 billion to 4.5 billion, she just sent me an email. She was like, Hey Jamie, I know you’re interested in this, so I wanted to send you this article. So now she just feeds me all the information, but it really was laying the groundwork and letting her know. And I think not a lot of people go in anymore. A lot of people call. And so I think just me going and I went basically three times in a six month span. And I would say not a lot of people who look like me who are going in to a small cornfield town in Indiana to ask about real estate.
And so that helps me in my favor where I stick out. And so that’s helped people remember me. Even I go to the same bakery, they’re like, Hey, you love the blueberry muffin last time, try this one. And so now that I really know I want to invest in this town, I see the opportunities in this town. I’m trying to find off market leads in this town. So I drove for dollars one time I was there. And so just talking to people, getting out, walking downtown, I have to use air quotes because I’m from a large city where I can’t really call it a downtown, but it’s about a block each side, but just really planting roots in that area. I’ve had even my neighbors would do my shoveling and stuff for snow and won’t let me pay them, I think because I’ve came out and brought them blueberry muffins. So just I realized stuff like that goes a long way where in markets like New Orleans made the mistake of not making those connections beforehand. And so it’s much harder to operate. So just trying to do it better this time.One other great way to find out about what’s going on in the city is going to the city website and reading the planning board meeting minutes. It’s so boring, but it’s actually so interesting. You will see so many things in there as to what’s upcoming on the agenda for the next meeting that maybe you actually want to attend because it’s something that could affect your business or whatever. But that’s another good way. If for some reason you can’t actually physically get to the town to walk into the town hall there to meet the clerk.That’s another great tip.Okay, we’re going to take a short ad break real quick, but when we come back, I definitely want to hear about this New Orleans property and how it’s not as easy to manage as the one you have in Indiana. We’ll be right back. Okay. Welcome back from our break. So tell us about the New Orleans property and it has not gone as you had hoped. Can you tell us that story and maybe some key things you learned from that deal? Specifically?My New Orleans property is definitely my hardest to manage and breaks even barely sometimes. Most months, no, this property I will say I bought creatively and being completely honest, I looked at, oh, I’m buying my first creative deal with not a lockdown. And the terms were great, and I looked at that and how I was acquiring it favorably more than the MTR rates and the area and just some of the things that I’ve done in other markets. And so definitely paying the price for that. It was vacant for nine months last year, so felt the pain a lot, but learned a lot as well. I think just about one, making sure that you’re doing research in the market. And so in Philly, Philadelphia is a, I think Philadelphia has a connotation that most people know, but New Orleans doesn’t always have that same connotation, but can be a much harder market to operate in.
And so the property where I bought is about seven minutes from the French Quarter and Bourbon Street where the party is, but it’s a few minutes in the wrong direction. And so definitely should have sent someone out to do a sweep of the area and walk behind the property, walk a few blocks and go to the grocery store and just see of what is the neighborhood like. Also, I have done a great job with other markets of building business to business relationships and renting outside of Airbnb and other direct platforms and building my own relationships where frankly, this property isn’t in an area where businesses will want their employees or clients to live. I’ve had great success now that I’ve listed mostly on Airbnb and lowered my rate a ton, but it took some hard lessons on going for a lower rate just to break even. And then also we’ve got hit with, our insurance went up about 150% since buying taxes doubled. And so the numbers are just squeezed. I definitely learned more about even if you’re able to acquire the property at $0 down, you still want to do the same analysis you would if you were putting a million dollars down because at the end of the day, the property management, the reserves and all of the continuous asset management of the deal can really make or break you.So Jamie, why haven’t you sold the property? Can you kind of break down what your plan is with the property and why you didn’t just offload it?Great question. So we definitely did try. We basically had a list for sale and rent as an MTR essentially at the same time just to see whatever one kind of bit. First we found an MTR tenant first, and that person has been there a long period of time, and now that I know the pricing, which was just a lot lower, again, new Orleans is another market that’s experienced short-term rental regulations. And so it’s just been really squeezed me, and I have a partner on this one, and we actually did do kind of an analysis on should we sell it, and right now we would lose a good amount because the seller financed a part of it at 0% interest, but we would have to pay the seller back upon sale. And so right now, even if it stays at the same price that we bought it at, just where we at in the loan cycle, the seller owned it for 10 years, we’re getting a lot of principal pay down.
And so right now it’s breaking even, I think last month cashflow at $115. But the month before that might’ve been negative $300, but the fact that it’s breaking even, we haven’t put any money into it in a few months, we are decided just to hold on at least for another year. But another thing too, it’s funny that there’s other benefits of real estate because one last year in 2024, I wouldn’t have been able to get my reps or real estate professional status without the property. A vacant property takes all your time, all of it. And so that’s helped because the other properties were doing great and my virtual assistants do most of the management, and so I probably wouldn’t have been able to claim rep status. Another thing is New Orleans is my favorite city in the us and so getting to go and use it as a business expense, of course everything is a business expense, but that’s another benefit. And so it’s definitely something that we’re going to offload as soon as it financially makes sense.Yeah, thank you so much for sharing that because I think it’s a great example of when somebody gets into that situation is maybe there’s more options than just like fire sale, let’s get rid of the property and move on where that sometimes may be the best option, but it’s important to compare and look at all the different options that you have when a property is not performing as expected. And in your case, you are being optimistic and looking at the other benefits that you are receiving still from this property and those outweigh taking the loss of selling the property now as is.Well, Jamie, there’s always ups and downs, and like Ashley said, I think we appreciate you sharing that, but it sounds like you’re also eyeing a transition over to commercial real estate. So I guess what is the strategy there? What’s the plan there? Maybe even before that, what’s the motivation? It seems like you’re doing pretty well with your midterm rentals. Why jump over to commercial real estate?So we didn’t talk as much about my well as we did my past and being in commercial real estate. And so that’s what I did right out of, and it’s funny, I felt like I’ve relearned a lot about single family, but with multifamily, and I’ve underwrote businesses as well, it’s a bit easier for me to analyze just because what I was taught. And then also, I definitely want to grow my midterm portfolio. My goal cashflow is 10,000 a month right now with four properties. I’m at 6,000 a month,More than halfway there.Yeah, it’s really three properties because one, again, it doesn’t really count, but I definitely want to buy more cashflow in midterms to get to that 10,000 a month. But then I see commercial real estate as more of wealth building. My goal has been cashflow with most of my properties, especially since I’m doing this. And so I see commercial as being something just fun different, I like commercial. I think there’s different strategies that you can implement in commercial. And before leaving my job, I was managing their whole commercial, their multifamily portfolio. It was about 14,000 commercial units spread throughout like 22 markets. And we would do things in different markets like installing smart EV chargers, and just I would see how it would impact NOI and our evaluation because at that role, we re underwrote properties and redid the valuation every three months. And so I’ve just seen the power of commercial real estate and how small changes to other incomes, small ways to cut expenses, can really catapult the NY, which goes to the valuation, which goes to your wealth. And so it’s definitely not something I’m going to do this year unless someone brings me a great deal. But it’s something I’m still learning multifamily, and I’ve done mixed use as well, is what I’m comfortable with. But I’m just looking into different asset classes. I’ve looked into boutique motels and hotels or self storage, and I do have a bit shiny object syndrome. So now I’m just looking at the feasibility of different commercial assets to see what might be next in the next few years.Well, Jamie, thank you so much for joining us. I really appreciated you taking the time to come onto the show and to share your journey and your learning experiences. Could you let everyone know where they can find out more information about you?Sure. And thank you so much for having me. I’m most active on Instagram. It’s Jamie Banks, so my first and last name, real estate, and yeah, you can follow along my journey there.Awesome. Thank you so much. I’m Ashley. And he’s Tony. And we’ll see you guys on the next episode of Real Estate Ricky.