Semi-Retired with a Small $6,000/Month Rental Portfolio

Dave:
Just a few rental properties can change your entire life. Today’s guest rolled his former primary home into three rentals, and five years later he has 13 units and he has cut his taxing work schedule in half, and this isn’t some secret path that you need millions of dollars to follow. His first property was a condo for $240,000. This just shows that anyone could do it. So let’s find out how. Hey everyone. I’m Dave Meyer. I’ve been investing in rental properties for 15 years, and on this podcast I bring you the stories of fellow real estate investors who have also changed their lives through real estate. Today’s guest is Bill Price. He started with a two bedroom condo in Milwaukee and actually went more than 10 years between buying properties, but eventually he grew his portfolio to 13 units. Over the course of six years, nearly all of his properties have cost under 300,000, but even that modest, manageable real estate investing has allowed him to take more time off from his very travel intensive day job and would allow him to retire early in the future if he chooses to. This is a great conversation about the power of even basic real estate investing strategies. Bill isn’t doing anything crazy or difficult or time intensive. He’s just taking advantage of compounding his wealth over time. Let’s bring on Bill. Bill, welcome to the podcast. Thanks for being here.

Bill:
Yeah, thanks for having me. Looking forward to this.

Dave:
Yeah, me too. So tell us a little bit about yourself. How did you get involved in real estate in the first place?

Bill:
Yeah, so I moved to Milwaukee in 2004 right after college, and I got involved in the entertainment production side of things, went to school for music and sound production and got hooked up with a company doing all the big festivals, concerts in Milwaukee, Chicago, all that.

Dave:
That sounds fun.

Bill:
Yeah. Yeah, that’s great. And then with that, I bought my first condo. Buddy of mine said, Hey, I need a place to live. About four months after I was living there, and I said, well, I got a second bedroom that I’m not really using, and I’m never here because I was always traveling with concerts and all that. So he moved in and didn’t know anything about real estate, just thought, Hey, this way this guy can pay all my utilities. I’ll pay the mortgage and I’ll move on. So yeah, so that kind of started the career and that was like I said, 2006, and then it just kind of springboarded. And then I got interested in real estate and he moved out, but someone else moved in. I charged them more so they’d actually pay the mortgage versus paying the utilities, and it just kind of grew from there and really sparked my interest.

Dave:
Huh, that’s very cool. I think it’s a pretty relatable story. You’re kind of like an accidental house hacker. I think 2006, you might’ve predated the term house hacking. I think Brandon Turner came up with that in the early 2010. So fast forward us a little bit because it sounds like you did this for a while, but then something changed for you more than a decade later. So how did you shift from just being this accidental house hacker into a real or more intentional, I guess you would say, rental property investor?

Bill:
So I guess first off, leading up to getting to all that, I was really aggressive on paying off my condo kind of once the market came back about, and everyone’s telling me, don’t pay off your condo, just take the mortgage, ride it out. And I was actually on tour with Justin Bieber at the time, and it was the most money I’d ever made, and we’re traveling the world and I was told, Hey, you’re not going to be home for a year and a half. And so I’m just like, I’m throwing money at this place. So in 2014, I actually paid off my condo.

Dave:
Whoa, that’s awesome.

Bill:
That was a huge accomplishment. So then in 2016, my wife and I, we decided to move in together. And at that point I was like, I kind of want to keep renting this place out. It’s working. So I figured, let’s give it a shot. Let’s see what happens. It’s paid off, why not, kind of thing. So we wound up putting it up on, I think Craigslist back then. Yes, that’s what we were doing back background and rented it out immediately and had a great couple that lived there for four years. And so that was kind of the springboard of, okay, this works. And at that point, it was so easy because the condo wasn’t even 10 years old,

Speaker 3:
So

Bill:
Nothing’s going on with it. We had just gotten through a lawsuit, so we had a bunch of stuff replaced. It’s a condo, so there’s no real maintenance. So it was just literally free money at that point.

Dave:
This is such a relatable story. I think a lot of people feel like becoming a landlord or becoming a real estate investor is this huge decision, but for some people it just happens, right? You just start doing it and you notice that there are all these incredible benefits to it, especially when you have a paid off. That’s a pretty cool story and maybe unique to your personal situation, but it just goes to show how everyone’s come into real estate from all these different angles. It doesn’t necessarily mean you have to be full time or spending all this time on it as bill’s telling us, you can kind of just fall into it at one point.

Speaker 3:
Yeah.

Dave:
Cool. So fast forward in 2016, you started leasing it out, but from what I understand, a couple years later, right before the pandemic, you did start actually have a turning point. Can you tell us about that?

Bill:
Yeah, so in 2018, my wife and I were talking about what’s next and all that. And we were in our condo, our new condo, not the original one. And then I’m thinking, okay, do I buy a duplex and live on one side and rent out the other? What’s the next step here? So we just started going to a few open houses, found a realtor that was a listing agent that we really liked, and so started working with him and then realized maybe we just stay where we’re at, but still buy place.

Speaker 3:
So

Bill:
2019, we bought our first actual investment property, if you will, intentional investment property. I guess

Dave:
It

Bill:
Was a duplex. And from there I was hooked immediately. It was just like, okay, this is all working. It’s the way it should, and I have no clue if I’m doing it right or not. I was getting leases just off of Googling leases. They weren’t anything legit, I’m sure, but it was like, let’s go with this. Since then, it’s everything I’ve expected it to be.

Dave:
Before that purchase, had you done any self-education or thought much about it, or was it just kind of like, I can afford this? Did you run the numbers and figure out if it was going to cashflow?

Bill:
Nope. I didn’t know what running numbers were. I just figured, okay, I think maybe this sounds like enough rent for this area. This is what the mortgage will be. If I didn’t like it, we had some extra money, I’ll just put more money down. There wasn’t any thought of, do you put less or more down? There wasn’t any education to it, it was just let’s give it a shot and see what happens.

Dave:
Okay, good for you. And you’re in Wisconsin, right?

Bill:
Correct. Milwaukee? Yep.

Dave:
Okay. And so what kind of price points are we looking at?

Bill:
So the first duplex that we bought was 185,000.

Speaker 3:
It

Bill:
Was a three bed, one bath, upper lower duplex. It’s in kind of the southern part of Milwaukee, Milwaukee County, city of Milwaukee. It’s actually three blocks of identical duplexes.

Dave:
Well, something must have worked about this here talking to us today. So what was the experience? I mean, you’d already had some rental experience. Was it much different when you did this new duplex?

Bill:
Yeah, for sure. When I had my condo, we had the most amazing people. They stayed four years. The only reason they left is actually they bought the unit above the one that they were renting. They didn’t want to buy on the first floor, but they were retired couple empty nesters, most amazing thing. Then when I buy this property, we actually found it on Craigslist as well. It was for sale by owner, and the landlord said, oh yeah, the bottom unit is occupied. It’s been a tenant. He’s great. It’s the upper unit. The person’s moving out shortly, their lease is ending, all that. And of course, I know nothing. So I buy it. And the person upstairs, she moved out, but she left me some parting gifts. She pretty much didn’t trash the place, but for someone that bought the place and a month later you’re just like, what just happened? And then the lower level tenant, he about three months after I bought it, decided he didn’t want to pay rent anymore.

Speaker 3:
Oh, no.

Bill:
So here I am buying my first actual place, and I still had the other place with the great tenants, and now I’ve got these other tenants that are just total opposite experience. And so that was kind of the wake up call of, oh my God, should I be doing this? That kind of thing.

Dave:
I do want to ask you and sort of understand why you kept going after that given that hardship, but we do need to take a quick break, so we’ll be right back. Welcome back to the BiggerPockets podcast. I’m here with Bill Price. He was just telling us about a very challenging first full-time investment. You bought a duplex in Milwaukee, had a very difficult tenant situation. A lot of people might walk away. These are kind of the things I think that as investors, when you’re thinking about making your first investment, you sort of have nightmares about this is the stuff where you’re like, I’m just going to keep investing in the stock market. I don’t want to deal with this. So how did you both mentally and financially navigate that challenge and keep going?

Bill:
So fortunately, the upstairs person was paying all the time. Once he did get evicted, I did actually file the Milwaukee County, had some relief funds and all that. So I actually did get most of the money in the end and just kind of figured to myself, okay, I got the money. This was a terrible experience for almost a year, but in the end, it worked out. And so rather than the negative and being scared in the end, I was made to fix up what I needed to fix up, which wasn’t much. And I went ahead and re-rented it again immediately. It was in a great area, great clientele and all that. So I was just like, okay, that wasn’t so bad. So then that brings us to 2021, and at that point I’ve figured I’ve got a place that’s totally paid off, and I could sell this and springboard it into other places, and I’m kind of at the cap of where that place can be. I can’t really charge more rents. I can’t do more value adds. It’s where it’s, so I went ahead and sold it in 21. So did the 10 31. Didn’t have anything in mind right away. We were actually also refinancing our primary home because we were on an arm when we bought it in 2016. So we’re going through that, and that was a whole struggle because as a sound engineer,

Bill:
And so I’m not working at that point. My wife and I weren’t married yet, so everything was just me. So we’re sitting there and I’m freaking out about this five-year arm that’s coming due, and finally I get a bank that will deal with me when that happens. I was like, well, let’s see what I can get for a mortgage, right? And so she’s like, well, how much do you have to put down? And I’m like, well, I have this whole amount from the previous condo. And she was like, did you ever think of splitting that up?

Dave:
The mortgage lender was the one who suggested to you.

Bill:
She brought it up again a second time,

Dave:
Just she wanted to just kindness of her hard advice.

Bill:
It was like four months of me trying to get a mortgage with her from all the self-employment stuff. So there was that. She knew that I’d bought a place, and she’s like, you’ve got $300,000 sitting there. Don’t just go buy one place, split this up.

Dave:
That is some very good advice at a very good time in the housing

Bill:
Market, right?

Dave:
Yeah. And was she willing to lend to you on that, just out of curiosity, or did you have to go through hoops to get multiple mortgages, or how’d that work out?

Bill:
Well, once we got the primary figured out, that was the hoop. Like I said, that was four months to get that going with my whole situation and my industry, and some of my jobs are 10 99, some were W2. And so she was like, we’ve gotten through this hurdle. Let’s run with it while we can.

Dave:
Yeah, that’s smart.

Bill:
So then I’m talking to that agent that I’ve been working with for a few years now. We’re still going to open houses, we’re seeing what we can. And then he said, Hey, something came across my desk with two properties that are four houses apart, two duplexes in an amazing area of Milwaukee, Bayview,

Dave:
And

Bill:
Do you want to go look at ’em?

Dave:
Two different duplexes.

Bill:
Two different duplexes.

Dave:
Okay, so four total units,

Bill:
Four doors, correct. So we go look at ’em, and I’m like, funny you said this because the bank just told me, let’s go ahead and do that. So we went and looked at ’em at that point. Now I’ve done some research of how do you make numbers work? I’ve made a little spreadsheet of myself. I think BiggerPockets was releasing spreadsheets at that point. I would hope so. So now I’m like, okay, now I know if I’m going to make money or not.

Dave:
Imagine that,

Bill:
Right? Everything cash flows cool, let’s move forward. At this point, I’m just buying two places. Put the offer in. We’re 45 days out from closing. We do all the things very traditional. It’s my first time really going through the whole process because it wasn’t NMLS, but it was still through an agent versus for sale by owner. So while we’re doing all that, coincidentally, the landscaper of my condo complex knows that I’m buying properties now just chatting with him and he says, Hey, my dad’s got a four family less than a mile from you that he’s looking to offload. Are you interested in

Dave:
It? Did your mortgage broker just go out and tell everyone that? She was like, I’m going to orchestrate Bill’s entire rental property portfolio. We’re going to make this happen for him six months. Well, we’re going to get it all done in six months. That’s amazing. Okay, so is that a good deal also?

Bill:
So I go look at that place, and this guy hadn’t raised the rents in nine years. All of the tenants have lived there for 15 plus years. And he says, give me a, so we looked on Zillow and probably should have offered him somewhere around 3 80, 3 90, and we offered him three 20. And he was like,

Dave:
Great. Yeah, this story you started. So it was a bad luck story, but now

Bill:
This is turning into a very good look

Dave:
Story. Okay, keep going.

Bill:
So I call my banker and I say to her, Hey, I know we’re full steam ahead with these two mortgages. Any way we could pull some money out of both of those and we can move it into a third. So rather than doing 150 on each of ’em, we did a hundred on all three of ’em,

Dave:
And that was still more than 20% down on each of them,

Bill:
Still more than 20% down. We’re still well within the numbers. It’s great. So she’s like, this is amazing. She’s just like, how did we go from four months of barely getting you one mortgage to now getting you four mortgages? And I’m like, that’s a great question. How did we do that?

Dave:
I hope you bought her some sort of very nice gift after

Bill:
All, right? Yes, we have stayed connected and all that. So at that point, I buy this other property that on paper doesn’t make a dime. The rents were so low.

Dave:
This is the third one, the four unit, right?

Bill:
So the two that were four doors apart from each other, those, like I say, it’s Bayview, it’s an amazing area. Rents were great. They all had tenants. The tenants didn’t want to leave. Perfect situation, super easy, low key, all that. So then I buy this third one and I’m like, okay, well now here’s the struggle. The question of how much do you raise rent before they walk out and this and that and everything. At the time, all of their rents were $600 or less, and market value is a thousand.

Dave:
Yeah, that’s a dramatic change.

Bill:
The first year I owned it in 2021, I only raised the rent $50 because I’m like, we’ll test the water, right?

Dave:
Yeah.

Bill:
Well then 2022, I raised it, $200 we’re going to keep going here. Right?

Dave:
And rents were going up crazy at that point too. So probably even more than a thousand was market

Bill:
Rent. Yeah,

Dave:
Market rent probably went up 10% of that year alone.

Bill:
So yeah, so that’s 21 and 22. And at 22, I paid off that original duplex that I bought just because I was on another tour. And once again, when I’m on tour, I don’t really spend any money, so I’m just throwing money at it and it’s great. And so now everything’s making money. So now the dollar signs are there. I’m definitely not retiring anytime soon from this, but okay, this is the plan and the plan’s starting to work,

Speaker 3:
That

Bill:
Kind of thing. And I will say that those three mortgages that I got, we’re all at 2.7%. Hold on

Dave:
To those for dear

Bill:
Though. Those I will not be paying off anytime soon.

Dave:
Yeah,

Bill:
No reason to do that for sure.

Dave:
Yeah. And so this whole time you’re working, and I don’t know how you get paid, but it sounds like you go through these spurts where you’re just living super cheap because I assume they’re paying for your hotel rooms and you get a per diem on your food, or there’s, I imagine in my head, there’s an amazing catering truck at all of these different events that you’re going to.

Bill:
There’s catering, some are great, some are not, but yes, there is. Yeah, I mean, it’s hard to spend money when you’re on the road. We live in tour buses, so we have a bus list of whatever we want when days off. We’re in hotels that are paid for. So yeah, so it’s a great life for saving

Dave:
Money for sure. Certain jobs have these perks, and I think that’s just a lesson for the audience. Not everyone’s going to have Bills job, obviously, but some jobs are flexible, and that means you can self-manage. Some jobs mean you can save money like bills, and you can pay off your mortgage a little bit. Really, you don’t have to go into real estate full time. You can find ways to leverage your existing job, and not everyone, but there are a lot of jobs that you wouldn’t think, oh, that supports a great real estate portfolio. I don’t think audio engineer would’ve been on the top of anyone’s obvious list of things. But the way you tell it, it does have some perks that really enable you to be a real estate investor. So even for people who aren’t pursuing full-time investment or you want to be a full-time investor and just haven’t gotten there yet, just look for these kinds of things that you can do that can really just help accelerate you. I think Bill’s providing us a perfect example. I want to hear more about where you’ve gone here. Bill, is it good luck Bill or bad luck Bill coming for us next, but we got to take a quick break. We’ll be right back.

Dave:
Welcome back to the BiggerPockets podcast here with Investor Bill Price. We learned about how Bill somehow magically just got 10 units in seven months, which was super cool, that got us to 2022, but you made a shift in 2023 with your strategy, it sounds like. So what did you do?

Bill:
So 2023 comes out at this point. I’m working for the band Weezer.

Dave:
Oh, cool. I’m a millennial. I love it.

Bill:
Yeah. So in 2023, I knew that I had four or five months off that I was going to be at home for. So someone approached me in the Milwaukee area and he said, Hey, I’m looking to offload my portfolio. I’m looking to go more commercial. Are any of these units any interest to you? I look at his portfolio and there’s one that’s great. And so I say to him, Hey, this one I’m interested in, can we go look at it? And he’s like, well, I’d really like to just sell it to you. And I was like, well, I need to look at it here, kind

Dave:
Of want to look at it.

Bill:
So he tells me, he goes, we’re going to go in. You literally can’t say anything. Don’t talk to the tenants, none of that. Let’s just walk through. So we walk through it and it’s in terrible shape. So he wanted 1 95 for it. And at this point, I’ve never negotiated a deal because all the other ones have come to me as we talked about earlier. And so I negotiate with him and I said, well, I’d go probably 1 40, 1 45. And he says, well, thanks. I’ll let you know. So a few weeks go by and then he calls me back and he’s like, all right, let’s chat about it and everything. And so we get to meet in the middle and we bought it for one 60.

Dave:
Okay.

Bill:
So my idea with that was it wasn’t in great shape. So I figured this is the bur method that everyone talks about. It’s cheap enough that I can use my home equity on my current primary home. We’re going to buy it, we’re going to do the bur method, and it’s going to be this huge success story. And now I’ve going to pivot that way. And so now I’m going to start my first Reno I’ve ever done. All the other places I bought, I didn’t have to do a thing too.

Dave:
Was this when you were off tour, you were willing to take this on at home a little bit more?

Bill:
Right? I have four months to get this whole thing done. I had a handyman that I’ve worked with before, but he was like, I’m a handyman. This is too big of a project for me. I’m calling contractors that I know nothing about. I get a few quotes and this one guy comes in and sounds great, and I think I gave him 500 bucks to lock him in or something. And the first day he comes and he brings three other guys and he leaves. The biggest project was we had to tear the bathroom all the way down to the joists because the subfloor was rotted out and one guy almost fell through because he didn’t know where the joists were and what he’s ripping out. So fourth or fifth day, I fire the contractor. So now I’ve got about two, two and a half months before I’m supposed to go on tour.

Bill:
So I call and beg and plead to my handyman guy. I have another buddy, he’s a carpenter for production work, so he knows how to build things. And so in about two and a half, three weeks, we did 80% of this work. I had a budget of about 20, 25 K to do at that point. Well past the 20 5K. And I’m just like, well, we’re going to keep going. I don’t know what I’m doing, right. I’m totally winging this thing. And I’m about a week and a half from being done and getting ready to put it on the market. And my realtor comes to me and he’s like, I have a buyer for you. And I was so stressed out at this point. So the buyers, they come through and they offered me two 60. So I do all my numbers and I’m like, I can get this whole thing done for 40 grand, so if I can flip this place for 200 all in and sell it for two 60, I’m running. So that’s what I did. So I call it my x and l flip.

Dave:
Did you like the process of renovating and did you like getting that big equity hit from flipping, or did you prefer rental properties at that point?

Bill:
It was overwhelming. Obviously the big equity at the end was great, but no, I didn’t really enjoy it.

Dave:
Okay. I assume you didn’t buy the rest of the portfolio from this guy after that

Bill:
Experience, correct. Right. Yeah.

Dave:
So these ups and downs though, are really just kind of this story of being a real estate investor, and I think that it scares some people away, but not every deal is going to be like this. Some of they’re going to be easy. It sounds, we’re focusing on some of the harder stories, but this is just sort of how you build a portfolio over time is just find yourself in some deals, there’s going to be some challenges, but look where you’ve come. I mean, yeah, you start in 2006, but just since you really sort of started doing this in 10 years, you’ve acquired a considerable portfolio. Have you done anything more since that flip and where does your portfolio stand today?

Bill:
So this March in 2025, we bought another duplex that was eight houses down from the first duplex I ever bought.

Dave:
And what’s the plan going forward? Are you going to just keep doing it? You’re still working, it sounds like. Is that sort of your strategy going forward?

Bill:
So I don’t think I’ll ever give up working, but the idea is to throttle it back. I used to do 36 to 40 weeks a year out on the road, and this year my goal is 16 weeks.

Dave:
And the fact that you’re able to sort of scale that down, is that because of your real estate income?

Bill:
100%.

Dave:
I mean, that’s just such a great example. I think so many people get caught up in this idea of quitting your job and that financial freedom is this destination that you have to get to, that you’re either financially free or not, but your story is a perfect example that it doesn’t have to be so black and white. There’s a lot in between, and you’re able to use real estate to continue doing what you love, but just at a pace and a scale that is more appropriate for your stage in life and that you want to be at. I think that’s such a cool goal and doesn’t get talked about enough in this industry that these types of goals where you just get to do what you want, even if that includes continuing to work. Real estate can help get you there.

Bill:
Yeah, yeah, for sure. Yeah.

Dave:
Well, thank you so much for sharing the story with us. Bill, this was a really fun episode. I really enjoyed hearing and learning from you. Thanks for joining us.

Bill:
Yeah, I’m glad to do it. It was a great experience,

Dave:
And thank you all so much for watching and listening to this episode of the BiggerPockets Podcast. We’ll see you next time.