How to House Hack Your Way Out of $200K in Student Loan Debt!

22 Jun 2026 · 39 min · 17 chapters

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In short

How James and his wife Ida used “house hacking” (an ADU/garage conversion) to eliminate about $200K in student loan debt, then scaled conservatively into a small portfolio and later used a tenant-driven rent-to-own strategy.

Guest backgrounds

James (31) was a healthcare director; Ida (24) was a data scientist. They moved to Pennsylvania, were renting, earned about $300K household income, but had $200K student loans, two car payments, and saved under 10%.

Key claims

Weekly “money dates” kept them aligned and math-driven. Their first real estate step was calling an investor-friendly realtor. They financed a $57K ADU with a $50K private lender loan, refinanced after completion, and used rental income to “live for free.” They later consolidated to four properties, avoiding over-leverage.

Notable examples

Main house rent $2,750 vs mortgage about $2,650 (roughly $100 net). ADU project took ~6 months; purchase ~$445K, ~$60K rehab, ~ $515K holding cost, appraised ~$675K. They later structured a tenant rent-to-own: bought condo $185K, rented for two years, option fee 20% of purchase price, sell back at $205K.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Kitchen Table Revelation

0:29 to 2:59

James discusses the pivotal moment at his kitchen table that led to a financial reevaluation.

“And with that, let's give a big warm welcome to James.”

Taking the First Step

2:59 to 4:30

James describes the initial steps taken toward homeownership and real estate investing.

“where they sit down and they're like, man, the path that we're on is not going to actually get us to the end result that we want.”

Navigating Real Estate Opportunities

4:30 to 7:21

The couple explores different properties and learns about the real estate market.

“Yeah, I think it was a blessing in disguise that he actually wasn't the right agent for us.”

Balancing Risk in Real Estate

7:21 to 9:39

James shares insights on aligning financial goals and risk attitudes with his wife.

“I removed the emotion from the decision.”

Balancing Risk in Real Estate

12:42 to 13:12

James shares insights on aligning financial goals and risk attitudes with his wife.

“estate, it feels like every dollar has a job, down payment, reserves, repairs.”

Balancing Risk in Real Estate

13:15 to 14:45

James shares insights on aligning financial goals and risk attitudes with his wife.

“The first time I used it, I realized my savings rate had quietly dropped while my day-to-day spending crept up a little bit.”

Balancing Risk in Real Estate

14:49 to 14:59

James shares insights on aligning financial goals and risk attitudes with his wife.

Analyzing the ADU Investment

14:59 to 20:41

James shares insights on financing and renovating an ADU to maximize property value.

“So before the break, we heard about James and Ida doing a nightly deal analysis around the kitchen table.”

House Hacking Success

20:41 to 23:07

Discover how James and Ida turned their property into a profitable rental.

“What was the amount of the rent that you were able to charge?”

Future Real Estate Strategies

23:07 to 28:04

James discusses strategies for scaling a real estate portfolio and transitioning to larger deals.

“Now, James, what about the next deal and your deals going forward?”
Show all 17 chapters

Transitioning to Multifamily Real Estate

28:04 to 30:58

Learn about the steps needed to move from a smaller portfolio to multifamily investments.

“James, what would be a good first step if somebody is in the same position for you where they've maybe have a built a smaller portfolio, but they want to make that transition into larger multifamily complex?”

Transitioning to Multifamily Real Estate

32:09 to 32:45

Learn about the steps needed to move from a smaller portfolio to multifamily investments.

“Find a co-host at airbnb.com slash host.”

Creative Solutions in Real Estate Deals

33:51 to 40:40

Hear about a unique tenant-driven opportunity and how to structure rent-to-own agreements.

“So we're here with James and he built a system that brings them deal flow.”

Actionable Steps for New Investors

40:40 to 42:05

Discover key actions rookies should take to progress toward their first real estate deal.

“But for the rookies that are listening who, you know, they have some money saved.”

Identifying Your Concerns in Real Estate

42:05 to 42:50

Learn how to recognize and address your uncertainties in real estate investing.

“So like, are you concerned about where you're going to get the money from?”

Guest Insights and Closing Thoughts

42:51 to 43:31

Hear final insights from guest James and the hosts' reflections on his journey.

“No, you made some great points there as well.”

Invitation for New Guests

43:32 to 44:08

Learn how to apply to be a guest on the podcast and share your story.

“I'm Ashley and he's Tony, and we'll see you on the next one.”
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Transcript

Automatic transcript. May contain errors.

0:00Ashley Kehr:Today's guest was climbing the corporate ladder, had a stable job and good income. But when he sat down with his partner at their kitchen table and they actually ran the math on what their next 30 years looked like, they didn't really like the answer. He was 31, she was 24, and quietly running the numbers on a retirement plan they didn't believe in. Then she looked up at the empty space above their garage and designed the deal that broke the house.

0:29Ashley Kehr:This is the Real Estate Rookie Podcast. I'm Ashley Kerr. And I'm Tony J. Robinson. And with that, let's give a big warm welcome to James. James, thank you for joining us on the Real Estate Rookie Podcast today. Thanks for having me, Ashley and Tony. Appreciate it. So James, let's start with that moment at your kitchen table. So is this something you guys would usually do is sit down and kind of put together a financial game plan, look at the future plan? Or was this the first time that you had done that? No, yeah, that's something we pretty regularly did. We'd sit down and have money dates and talk about our finances and our future and how to get set up and get to where we want to be.

1:06Jim, let me ask just really quickly, because I love the idea of the money dates. For rookies that are listening that want to replicate that, just give us the quick agenda. Like how often and what were you guys talking about in those meetings? Clearly, it had a big impact on your financial future. Yeah, we've actually kept it up for years now at this point. Once a week, an hour out of the week, usually before we start our actual date night. That way we're not too tired. We got all the stuff that we had sitting on our shelves brewing and our minds off our plate and we're able to enjoy our time together.

1:39But we sit down, we review what we spent, what we plan on spending, where we are compared to the budget that we set, any adjustments that need to be made. And since we're doing it so frequently, week to week, there's not really any room for things to get too off the rails.

1:56Ashley Kehr:Now, James, when this point in your life, when you're looking down and not liking what you see for the future, where were your financials at at this point? Did you own a home? Did you have any debt? Things like that. So I just accepted a new job that moved us out to Pennsylvania. We didn't know the area at all. So we were renting a house while we figured out exactly where we wanted to live. We were making pretty good money on paper. I was a director for a health care company. She was a data scientist for an insurance company. Household income about$300K. The reality of that was we also had$200K in student loans, two car payments.

2:36we're saving less than 10 % of our income. So that's kind of where we were. I was 31. She was 24 at the time. And we realized, you know, sitting down at that money date at the kitchen table, hey, this is going to be 30 or 40 years of this grind. And neither of us were really willing to wait that long to dedicate more time together. I think there are a lot of people, James, who maybe have that same realization, though, where they sit down and they're like, man, the path that we're on is not going to actually get us to the end result that we want. And they wait months, sometimes years before they actually take action.

3:15What was the first thing that you guys did that wasn't reading another book or listening to another podcast? What was the first thing you did in the real world that gave you some forward momentum towards changing that trajectory? Sure. Yeah. I liked how you mentioned not reading another book, not listening to other podcasts because we've done all of that at that point i think we had spreadsheets coming out of our ears so um the first thing that we did was call a local real estate office um we called to connect with an agent we said hey look we're throwing all this money away renting we know that we should own a home we want to treat it like an investment not just a nice place for us to live it's something that will aid our financial goals um and i had the idea of house hacking so we said all right let me call local office get the the best investor-friendly agent that they have to hook us up and teach us, to show us all the exciting things.

4:06So that was the very first step that we took and started going on some tours with him to look at things that we thought fit our model. What did that conversation with the realtor maybe teach you that not listening to another podcast or another book could have taught you? That first real-world taste of being a real estate investor, what was different than the books and the podcast. Yeah, I think it was a blessing in disguise that he actually wasn't the right agent for us. He kept talking us out of every opportunity that we looked at, everything that we came across. And the thing that gave us the confidence that we weren't going to get from books or podcasts or anything was realizing that independently, even though this expert was telling us that it didn't fit our vision or it wasn't a good deal or it wasn't a good idea, we independently felt differently and we saw the opportunity in it.

5:02Okay, we can make this work. And when we coordinated together after doing that showing, we realized, you know what, we don't necessarily need everybody to align with our vision. We believe in this. So we're going to go for it.

5:16Ashley Kehr:So take us through some of those deals that you looked at. Did you make offers on any before you ended up on the one that you actually purchased? We didn't actually, no. We only offered on the first one that we uh purchased we did walk through a lot of different houses though he was taking us all over town there was a lot of traditional duplexes that were built for for the purpose of you know two two families um uh three family homes even there was a lot of homes that were in a multi-family zoning but were single family homes so um they were listed at a little bit of a cheaper price, needed a little bit more work, had the opportunity there, but not the actual structure.

5:59So it really required some imagination and thinking outside of the box, I think, to see those come to life. So eventually we landed on one that was in that latter group of being zoned properly, but was really just a single family house. And we saw the opportunity to do what we did there.

6:18Ashley Kehr:And now with this property, that opportunity was this garage space then? Yes, exactly. So there was a main house, about a 2 ,500 square foot, four bed, three bath house. There was a detached garage, two car garage, oversized, really, really quite large and a empty but somewhat built out livable area above the garage there. so that that's how we we saw that that vision and Ida was on it right away she's like we can live in that little apartment we can make it nice we'll rent out the main house I was a little bit more well I've been working my butt off I'm you know over 30 years old I'd like to live in the nice part of the house and maybe we rent out the smaller one and you know we'll we'll collect less profit.

7:10But she wrote the math down on paper, showed it to me, and was like, this gets us to our goal. This doesn't. Which one do we want to do? So we removed the emotion from the decision. I removed the emotion from the decision. We went with what made sense on paper.

7:27Ashley Kehr:But James, in a way, that is still taking your own personal preference into consideration. Just because you're giving up what you want now, you're giving that up so you can get what you want in the future. And so it's not really, you know, sacrificing something or it's not like giving up. Like you are actually just changing something now so that you can have what you want later. and part of the motivation of real estate investing if you want it really bad sometimes that motivation to get to what you want is going to make you do things like this where okay i'm going to live in you know the adu and not live in the main house i 100 would do that i would see that vision too i'm with ida is to like let's make as much as we can as fast as we can renting out the bigger house and we'll just live in this you know smaller apartment but i i think that can get lost with people.

8:28Ashley Kehr:And I love that she sat down with you and kind of wrote it out. I think so many people are visual learners and need to actually like see it rather than been told it. And I think that was just a great example right there. Yeah, absolutely. I mean, she has an amazing story and background, and I think it's allowed her to really be comfortable with this concept of delayed gratification and me having a very different background. I had to learn that some some hurt over time and it's been it's been a wonderful day and just for rick is in case we didn't clarify ida is james's wife uh who's been his partner throughout all these deals i know we thrown that name around a bit but uh james most rookies i think stall on real estate not because they don't see the path not because they don't have the the vision but they saw because they can't necessarily agree on the risk associated with investing in real estate and you kind of talked to us a little bit about like the mathematical approach that you guys took But in those early days between you and your wife, who was maybe like the brakes and who was the gas pedal?

9:32And how did the two of you actually align on what you were willing to put at stake in order to actually get things started? Yeah, that's a great question. I mean, especially when it's not just a business partnership, it's a marriage. There's a delicate balance to be held up, to be upheld there. I was probably more of the gas and Ida was the brake. she was rooted heavily in math I think just from a background and a you know natural personality type of thing and I was I was a little bit more of the the one willing to execute so you know we have an idea together and it's like all right let's go I see all the steps to get there so I'd get excited I started running scenarios where it could work and she just you know kind of pull the spreadsheet towards her and make us look at the math again, make sure that nothing was optimistic, make sure that we didn't need best case scenario for several components of the deal for anything to work, to really rein the whole operation in and kind of force everything to be based on math and not emotions, like I said before, that very first deal.

10:40Ashley Kehr:Well, we're going to take a short break, but when we come back, we're going to get into what actually made this deal work. So we'll be right back. When you buy your first rental property, there's usually a moment right before you pull the trigger where your brain starts spiraling a little. What if I'm making a mistake? What if I can't figure this out? What if this whole thing becomes way more complicated than I expected? Honestly, building any business feels like that at first. And for a lot of investors, that next step is creating a brand, a website, or even a business around what they're building.

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14:26Ashley Kehr:And speaking of results, in the minute I've been talking to you, 23 people just got hired through Indeed Worldwide. There's no need to wait any longer. Speed up your hiring right now with Indeed. And listeners of the show will get a$75 sponsored job credit to get your jobs more visibility at indeed.com slash rookie. Just go to indeed.com slash rookie right now and support our show by saying you heard about Indeed on this podcast. That's indeed.com slash rookie. Terms and conditions apply. Hiring Indeed is all you need. Okay, welcome back. So before the break, we heard about James and Ida doing a nightly deal analysis around the kitchen table.

15:06Ashley Kehr:The thing they were missing was the actual deal itself until they find that this property with the empty space above their garage, and they actually started doing math very differently. Okay. So James, let's break down the numbers on this actual property. So walk us through what did the ADU actually cost you and how much did you put into the renovation on this property and how long did it take? Yeah. So it took about six months and to end all in the ADU came out at about$57 ,000. So six months from when we started to when we actually moved into the ADU was that timeline. We financed it with a 50K loan from a private lender that we built a relationship with.

16:01We put the rest of our own cash and we were able to refinance at a much higher value after that AD was built and completed. Two things, James, that stand out to me from your story are the timeframe, but then also the money that you borrowed from a private money lender. So let's talk about the private money piece first. I feel like that's probably the part that a lot of rookie investors want to know more about is like, how did you do that? So who was this individual and how did you approach them with the opportunity to invest in the ADU with you? Yeah, great question. I mean, I think pretty similar to a lot of investors early on that the story is the same.

16:47It was a family friend, essentially, that had the money, wanted to do something with it, wanted to help us out, understood that we were reliable and trustworthy because they had known us for a while. So that's how that came about initially. Yeah. But James, how did you actually broach that conversation with them? Did they know that you guys had already been searching and were interested in real estate? Was it just a cold outreach because maybe you knew they had some capital sitting around? What did that conversation actually look like to get you to the point where they actually ended up funding a good portion of that deal for you?

17:28Gotcha. Yeah. We're both pretty direct people. So they were aware that we were looking for a house. We were very close and spoke regularly in our lives. So it wasn't a surprise that we were looking for a house. It was a surprise when we had this idea of a house hack and burr and we threw all these terms around and kind of pitched them the deal. They were honestly very skeptical at first. A lot of questions around, well, how do you know how much it's going to be worth afterwards? How do you know what you're going to be able to get a loan for? And how can you guarantee that I'm going to get the money back, let alone, you know, additional interest?

18:06And so we we anticipate a lot of those questions. We showed the math. We really broke it down step by step of what we did to arrive at those numbers. Here's how here's how it works. Here's why this works. Here's other examples of people doing that. I have a close friend that's also in the LSD and I had him kind of explain and be a case study for how he's done that several times. So all of those things helped and were part of that initial conversation with them.

18:36Ashley Kehr:During the rehab process, did you hire out all of the work or did you guys do any of the work yourself? We made the mistake of doing a lot of the work ourselves. And I say the mistake because it took much longer and probably cost us more in holding costs, which we weren't super, I guess, aware of on our very first deal than it would have to just pay a contractor to do it. It was a great experience. We learned a lot about construction in general. But, yeah, we had a mix. So a lot of the large foundational components, say, along with plumbing and electric. we had contractors for. My father was a carpenter for many years, so he helped us install the kitchen and do a bunch of other things.

19:26Kind of a mix.

19:28Ashley Kehr:Okay. So James, once you've finished the rehab, you guys move in to the ADU property. And did you refinance this right away and kind of give us like wrap it all together here yeah we did it was um end of 2021 when we um went under contract early 2022 when we closed on the deal or yeah early 2022 when we started the the construction we refinanced right away um and uh rented out we actually lived in the we lived in the living room of the main house while the adu was being built um slept on an air mattress on the floor we're getting dressed out of our clothes being in in garbage bags and it was a nightmare we did that for a couple of months until the adu was livable but not finished and then we um moved kind of into there um and finished building it and then refinanced right way.

20:29And as soon as we moved into the ADU, we also rented out the main house. So that one was ready to go. We started collecting some income even before the ADU was built. That helped a lot. And we finished it while we were living through the renovations there.

20:44Ashley Kehr:What was the amount of the rent that you were able to charge? So we charged$2 ,750 for the main house. The mortgage was about$2 ,650. So we're netting about a hundred and, uh, you know, living, living for free. I mean, that is the goal. You know, that was like a, that's like a perfect house hack is someone's paying you, uh, to live in the place that you already want to live in. And then what about the refinance on the, on the backend? So what, what was the, the total all in cost of your, your purchase price and your, your, uh, rehab of the ADU? And then what was the, the, the final appraised value?

21:17you yeah so uh we were the the house was 445 uh we put about 60k i think 57k into the adu as i said so um took us a little bit over 500k all in um plus the holding cost took us to about 515 um and it appraised for way more than than we anticipated about 675 so um here's a it was a home run right off the bat. We had a bunch of equity in there. Rates were great at that time, so we had a pretty good deal going.

21:51Ashley Kehr:You got to tell us what was the rate. It was 3.4. Wow. Yeah. James, but did you guys do anything to the main house or was all of the renovation budget just on the ADU? The main house was in almost trachy condition. We hardly done anything. There There was a few minor cosmetic things. We had to paint one of the rooms. We had to fix part of the ceiling and clean. That's about it. I mean, so you said you bought it for$445 ,000 and then it appraised for$675 ,000. So we're talking over$200 ,000 in equity gain just because of the 60 some odd grand you spent on the ADU. Yeah, adding a whole other family to be able to live in that place.

22:33And now we rent that out for$2 ,000 a month. So that's$2 ,000 additional on top of the main house covering the mortgage. So now that you've moved out, you're collecting, what, almost$5 ,000 a month in rents, and your mortgage is still$26 ,000. I mean, what are you clearing after all expenses? Like$2 ,000 a month, basically, on this deal? Almost, yeah. That's a great first deal. You got to thank Ida a little bit more, James, for having that vision, man. Every day I do because I really started to snowball and we never would have gotten there without her.

23:07Ashley Kehr:Now, James, what about the next deal and your deals going forward? So you've got this great first deal. And I know that you've said that you would rather miss out on 10 deals than force one deal. So what does the future look like after you got this home run deal and now you've moved out of the property? What's next? Yeah, so we actually stayed there for as long as we could to keep saving money, living for free. We used that opportunity to pay down all of our debt. We eliminated 200K of student loans in a year and a half. Congratulations. Yeah, thanks. We reduced our car, paid off our cars. We just focused on getting rid of our debt and not really doing another deal right away.

23:55We wanted to be in a better financial position and be able to approach the future deals from a position of power. So that was our number one goal. Our number two goal after that was, hey, we learned a lot about construction, about managing contractors, about holding costs, for example. So we felt like we had the experience and the education to keep moving forward. So we looked through. So our next deals came from a mix of areas. Not the same agent, but a different investor-friendly agent who passed us a couple of off-market deals. Zillow, we pulled our last two deals just straight off of Zillow.

24:40They were on the MLS. And one of them came from one of our tenants. So kind of a weird mix of sources. Yeah, James. So for the agents who are sending you off-market deals, I mean, that's the goal for a lot of rookies. They just have agents sending them deals that no one else has access to, right? That's like the holy grail of deal finding. How did you build those relationships? Or maybe better yet, why did those agents come to you as one of the people on their short list of properties to show these off-market opportunities? Yeah, that's a great question. I think the biggest thing is communication.

Read the full transcript

25:15Whether I was interested in a deal or not, we always got back to them with a reason. I took the time to write out a paragraph or more of, here's why this would work. Here's what we like about it. Here's why it doesn't work. Here's our thinking of what we're not going through. and I think that showed that we're serious about our next deal. So they're going to keep sending us things, but also it made us easier to work with and made them understand exactly what we want to do and what we're looking for. And we're able to refine their search a little bit. And it let them know we were there. We're live bodies looking to interact and make deals.

25:57And they weren't just sending stuff to an empty inbox. So I'm sure we're not the only ones getting you know, exclusive access to these deals, but we're always up in mind for them. Yeah, that's great, man. And then what does the portfolio look like today? So we intentionally consolidated very recently. We have four active properties right now, four doors down from over 10. And yeah, we've intentionally consolidated. We're looking to do a little bit larger deals, apartment buildings going forward. Talk us through that. Because I think for a lot of rookies, they fixate on the numbers, like the number of doors.

26:33So what was the math for you to say, hey, let's actually going from 10 to four is the right move for us? Yeah. I mean, more doors is more management, more risk. We're extremely conservative in our risk profile. We really don't want to be over leveraged in any case, I believe. And I guess what has been coined as a small but mighty portfolio. You have high equity, low debt across your portfolio, and you're able to pay those off and snowball that. And your overall net income increases from paying down your debt, not so much from adding more and more and more. So our thinking there was along those same lines.

27:24We never really had the goal of having 50 single-family homes or something like that or more, which many people do, and that works also. But that was a little too risky for us, and we didn't want to be over-leverage. So we consolidated. We have four really solid properties. That first one we ever bought is still staying strong. So that one hasn't left our portfolio. And yeah, we're looking to get into apartment buildings, 10 to 20 unit buildings to kind of diversify and help reduce that risk further in economic downturns. Well, you guys continue to scale.

28:05Ashley Kehr:James, what would be a good first step if somebody is in the same position for you where they've maybe have a built a smaller portfolio, but they want to make that transition into larger multifamily complex? What are some of the things that you're actively doing now to not only prepare yourself to kind of shift asset classes, but to, you know, know how to analyze the deal, you know, the manage these properties are totally different. What's something that someone else could replicate and getting themselves ready to take on multifamily? Yeah, that's a great question because it's a whole different set of underwriting.

28:45It's a whole different way of looking at the deals. It's a whole different set of financing tools that are available. So learning all of that kind of similar to before taking that first step, we were in the stage of learning all of that. We took a couple of courses and, you know, the same route of books and podcasts and became as educated as possible. And then, you know, remembering our initial experience of, OK, time to take the first step. I made a call to somebody that we've become very close with and now in the industry that has several large part buildings under their in their portfolio. and got a lot of advice from them and just kind of picked their brain and it became kind of a formal mentorship.

29:32I think that was key. That was really helpful. We put a business plan together to formalize it and make sure we knew what are the steps we need to take to accomplish the goals that we need to. So that was helpful also seeing it on paper. We're going to need financing. We're going to need property management. We need relationships for realtors and lenders and all these different contractors and people in each of the places that we're looking to invest. Yeah, well, James, you guys have continued to scale the portfolio with a very disciplined approach, but then a tenant of yours walked up with a request that completely changed how you thought about what real estate investing was even meant to do.

30:09So we'll cover what that pivot was in your portfolio after a quick word from today's show sponsors.

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32:50Tony Robinson: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 12-31-2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the Income Fund's prospectus at fundrise.com slash income. This is a paid advertisement. 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.

33:24Tony Robinson:It's an IRS-compliant 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 slash BP to get a free proposal and see your potential tax savings. All right, guys, welcome back. So we're here with James and he built a system that brings them deal flow. But the deal we wanna talk about next didn't come from any of those channels.

34:00It came from a tenant who walked up with a question. So James, kind of give us the backstory here. You got a tenant. And I guess how long had he been renting from you? And what was the conversation that kind of started this new strategy that you really hadn't considered before? And what did he tell you who actually wanted that the bank told him he couldn't have? Yeah, this was a really cool one and kind of an eye-opening moment for us because it was a reminder of why we even started this company and why we're doing what we're doing. It was an opportunity to help somebody else while still having a successful deal.

34:35ourselves. And so he was a tenant in one of our properties. He lived there for a little, almost a year. And he was a great tenant during that year. We kind of took a little bit of a chance on him because he recently quit his W-2 job and opened up a food truck. So he didn't exactly have verifiable income. Yeah. So that was another problem with the banks, which is why he was renting in the first place but um but he looked great on paper his business was great it was uh it was a food truck and food was delicious so i believed in that the product as well um so it just overall great guy took care of the place was really you know really respectful and polite and and he came to us on day he said hey um i know i found this this condo that that i really like, would love to be able to move into it.

35:33I would love to rent it from you. I can't exactly get a bank loan at the moment because they need, especially for self-employed, I think they told them they needed two years worth of income history and he only owned his business for a little under a year at that point. So me and I looked at each other and we're like, I think I think we could figure out how to do this, right? We have all the knowledge to get creative and the expertise to get creative and figure out how to structure this and how to make a deal work. So he really loved the place. That's where he saw himself long term. He was set on that being the place that he wanted to live.

36:12we were able to work out a deal with the seller to get a reasonable price who was also a great guy and and you know looking to get rid of the place and and help people out as well so that helped it click um and we put a rent to own um agreement together for for our tenant we bought the place for 185k um we're going to rent it for him he gave us a option fee and we're going to rent it to him for two years and sell it back to him at 205k.

36:45Ashley Kehr:So he moves out of your current rental into this condo that you buy and you set up this agreement, which kind of is giving you multiple exit strategies for this property. You have an end buyer in two years or you retain the property as a rental if he doesn't execute on the rent to own, or you could list it onto the market and sell it to someone else or continue to rent it. So this is interesting. I don't think that we've ever heard of this situation before where a tenant has actually came to a landlord and said, I want you to buy a different property and not the one I'm living in. And I want to move to that one.

37:26Ashley Kehr:But any tenants listening, this feels like a dream for a landlord. So bring deals to us. yeah no it was it was exciting i mean definitely unique uh we had to we had to put our heads together to figure out how to make it work but like you said it had multiple exit options i mean that's something that we're huge on if a deal only works one or two ways it's not really a deal because things go wrong all the time so it was nice having that option that optionality that flexibility and um and yeah he's a great guy so we he was able to get the house he wanted we were able to make a little bit of a profit and put the deal together and maintain him as a tenant, which we know we already trusted him.

38:11James, you mentioned an option fee. What is that? What was the amount? And then what happens to that option fee if for whatever reason he's unable to actually move forward with the purchase of the sale and the two-year timeframe? Sure. Yeah. So for a rent-to-own agreement, the option fee is the amount collected up front that gets taken off of the sale price at the end. So it's kind of like his down payment early on. We actually collected, which is rather unusual, but it was because it was a relationship that we had already built with our tenant, but we collected 20 % of the purchase price as the option fee.

38:52So that kind of removed all of our risk from from the equation and at the what happens if he doesn't purchase the place is that we keep that option fee so um it's technically earned income at the time that we received it we keep that option fee um if he defaults on rent or if he doesn't want to buy the place at the end um and basically we got that 20 down payment for for the condo um if he does decide to buy it um that option fee comes off of the 205 ,000 purchase press.

39:27Ashley Kehr:So did you, who came up, I guess, with this structure? Is this something you just proposed off the bat or did it take some kind of negotiating to do? I mean, first, somebody who's never done this before, I mean, it's, how did you figure out where to start, I guess, with structuring this deal? Google, Google is a great, but yeah, no, we had. Yeah, I guess ChatGPT could probably tell you what to do. Yeah, you're right. Yeah. No, it's a fairly standard arrangement for rent to own. We saw a few standard templates. We consulted a lawyer to make sure that we were doing it right. We didn't want to be putting him in a position that wasn't good.

40:06We didn't want to put ourselves in a position that exposed us to a lot of risk. So we did consult a real estate lawyer to help us put the contract together. But it really was just independent research and trying to figure out, hey, how can we make this work? Rent to own is a thing. It's not super common nowadays, I would say. But it is a viable strategy that's out there. Yeah. Well, James, I mean, you've had, again, some incredible success with the portfolio that you guys have built. But for the rookies that are listening who, you know, they have some money saved. Maybe they're in a W2 that they're not super thrilled about saying and for the next 30 years either.

40:50What roadmap should they be following? Like what's one move you want them to make in the next 30 days to actually make progress toward their goal of getting that first deal? That's a good one. I mean, don't take a course. Don't read another book. Don't analyze 50 different markets. pick one that works that is nearby or that you're familiar with. Run honest numbers on different properties every day. You know, not just the numbers from Zillow, not just the numbers that the listing agent sends you that are almost always inflated and incorrect. You know, go deep on what you're doing and what you know and what's there.

41:39you know i don't think you need the expertise of of anybody of anybody else really that you can you can just start taking action there i think like one thing i would add on to that james and

41:51Ashley Kehr:i think that's great is like asking questions and like not even like finding a mentor and asking them but like figure out what's like holding you back from maybe getting the next deal done and like ask yourself, what are the things you're concerned about? So like, are you concerned about where you're going to get the money from? And like figure out all of these things that you don't know. Like for the longest time, I didn't know what skip tracing was. And I would just like, I don't know what that is. And I would just let it go. And it's like a simple Google search would have told you what skip tracing was.

42:26Ashley Kehr:And it's like, as you, you'll become more confident and comfortable if these questions that are these things that you don't know, if you actually identify what these questions are that you have and you do the work to actually answer those questions, you will feel much more confident moving into a deal, analyzing your numbers, underwriting, all of that. So I think that was great advice, James. Yeah. No, you made some great points there as well. Makes a lot of sense. Well, James, thank you so much for joining us today on Real Estate Rookie. Where can people reach out to you and find out more information about your journey.

43:03Yeah, thanks for having me. It's been a pleasure. The best place is our website, www.riseup.capital. We're on Instagram too, at investwithriseup.

43:13Ashley Kehr:Well, thank you so much. We really enjoyed having you on to share your experience. We really did miss not having Aidan, but we'll have to have her on for a separate episode to get her insight into your real estate journey. Yeah, that sounds great. Thank you guys for having me. It's been a pleasure talking with you. Thank you, rookies, for listening to today's episode. I'm Ashley and he's Tony, and we'll see you on the next one. Hey, rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie Podcast.

43:48Now, 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.

43:55Ashley Kehr:As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal. So head over to biggerpockets.com slash guest if you want to be a part of our show. Again, that's biggerpockets.com slash guest. And we'd love to have you on. You can't reason with a son. Trust us. We've tried. This summer, it's time to put that angry ball of fire on mute. Colombia's OmniShade technology is engineered to protect you from the sun's harsh rays that can burn and damage your skin.

44:31The sun is relentless, but so is our gear. Level up your summer at Colombia.com to spend more time outside and less time slathering on aloe lotion. You're welcome. Colombia. Engineered for whatever.

From the publisher

At 31, James sat down at a kitchen table with his wife Aida, ran the numbers on the next 30 years, and didn't like what he saw—$200,000 in student loans and a retirement plan neither of them believed in. So they stopped waiting for a change, and built something instead.

Welcome back to the Real Estate Rookie podcast! Our guest, James Doren, and wife, Aida, didn't have a trust fund or an obvious path forward. They had a spreadsheet, a private money lender, and an empty space above their garage. This accessory dwelling unit (ADU) solution added 50% value on their equity, wiped out their student loans, and set them on a path that most investors never consider: intentionally shrinking their portfolio from 10 doors to 4. But the deal that surprised them most didn't come from an agent or Zillow. It came from a tenant who knocked on their door with a problem the bank couldn't solve!

James breaks down the house hack that started it all, how he convinced a private money lender to fund the build, and the rent-to-own agreement he structured for his tenant that gave both sides exactly what they needed. If you've ever sat at your own kitchen table and wondered if there's a better way…James's story is your proof that there is!

In This Episode We Cover

How James and Aida used weekly money dates to align on their financial goals and take their first step into real estate

The ADU build that created $160K in equity

How to approach a private money lender and handle the tough questions

Why James intentionally sold 6 properties and why owning fewer doors actually made him more money! 

The rent-to-own agreement a tenant brought to them: how it works, what an option fee is, and why it removed all their risk

And So Much More!

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Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 
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