$6,800/Month Cash Flow with 4 Small Multifamily Rentals

14 Jul 2025 · 39 min · 21 chapters

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In short

Ryan Allsop’s path from house hacking to a small Milwaukee multifamily portfolio producing about $6,800/month cash flow, plus how he used Airbnb and HELOCs to scale.

Guest background

Full-time filmmaker; started investing at 26 with no real estate experience. Grew up in a large family; hated paying rent.

Key claims

Buy a duplex to stop paying rent; take action despite “rookie” uncertainty; use long-term refinancing and equity to fund more deals; negotiate off-market deals directly; qualify financing based on rental income (DSCR concept mentioned); Airbnb can fund travel and savings.

Notable examples

April 2017 duplex house hack (10% down, 30-year fixed, no PMI) where upstairs rent covered mortgage/taxes; tenant stability for ~4 years. Second duplex in 2019 negotiated over ~100 emails off-market; verified leases/rents with property manager. Airbnb used in 2017–2020 to earn ~$1,000 for three days during film festivals. Biggest mistake: hired a Craigslist contractor for a bathroom reno, paid in portions, and had to rip out tile.

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

Ryan's Journey into Real Estate

0:29 to 1:38

Discover Ryan's background and what motivated him to start investing in real estate.

“Thank you so much for joining us today, Ryan.”

The First Property Purchase

1:38 to 2:24

Ryan shares the details of his first duplex purchase and how he found it.

“And I just could see, okay, I did the numbers and I could figure it out the rent that I could get for the upstairs.”

Overcoming Initial Challenges

2:24 to 3:52

Ryan discusses the initial challenges and analysis behind his first investment decision.

“Were you walking around the neighborhood?”

Leap of Faith in Real Estate

3:52 to 4:54

Explore how Ryan's leap of faith led him to his first investment property.

“Going into it, your goal was to house hack, but did you run any analysis to say like, okay, the numbers make sense on this?”

Success with the First Duplex

4:54 to 7:56

Ryan recounts his experience living in the duplex and the benefits he enjoyed.

“I love that you used the phrase leap of faith, because I think where a lot of rookies get stuck, Ryan, is in the dreaded analysis paralysis, where they listen to the Real Estate Rookie podcast.”

Long-Term Value of Real Estate

7:56 to 9:39

Discover how Ryan realized the long-term benefits of holding real estate investments.

“was a great deal to start with, the real power of this property is the long-term play.”

The Importance of Long-Term Thinking

9:39 to 11:28

Learn about the significance of viewing real estate as a long-term investment.

“they're, you know, attention grabbing and the hook has to hit and social media paints a certain picture of why we invest in real estate.”

The Importance of Long-Term Thinking

11:33 to 12:34

Learn about the significance of viewing real estate as a long-term investment.

“That's VFINANCIAL.COM and see what you qualify for.”

Ryan's First Duplex Purchase

14:11 to 15:40

Ryan discusses how he bought his first duplex and the lessons learned.

“All right, guys, we are back with Ryan and he just told us about the deal that changed everything for him.”

Negotiating Without an Agent

15:40 to 17:19

Ryan shares his experience negotiating a property deal via email.

“A lot of people wouldn't know what to do because a real estate agent does really hold your hand and walk you through those steps.”
Show all 21 chapters

The Importance of Due Diligence

17:19 to 19:26

Ryan emphasizes the need for due diligence when buying property.

“It was like a birthday party and we were just talking and my wife talked to her friend and she's like, I know this person.”

Understanding Seller Motivation

19:26 to 20:55

Discussion on the various motivations sellers might have to sell a property.

“And Ashley, I just want to add to the point too of why this person sold to Ryan without listing.”

Ryan's Financing Journey

20:55 to 23:12

Ryan explains how he financed his second property with a HELOC.

“I like to do a renovation project every year per property now.”

Investing in Relationships

23:12 to 24:01

Exploring the idea of viewing relationships as investments.

“But that was such a nerve wracking day there to the jewelry store and not knowing how I'm getting any of this money paid back, hoping that it all works out, but it did.”

Staying Local in Real Estate Investing

24:01 to 24:58

Ryan talks about the advantages of investing in his local market.

“I feel like there's going to be very mixed opinions on me saying that if people agree or disagree.”

Assessing Market Risks

24:58 to 27:09

Ryan discusses the potential risks of investing deeply in one market.

“You know, like if you think about cities across the United States where maybe, you know, a manufacturing plant closes and people, you know, a good percentage of the population loses their income.”

Assessing Market Risks

29:15 to 29:25

Ryan discusses the potential risks of investing deeply in one market.

“Almost every move that can still lower your 2026 tax bill expires on December 31st.”

Ryan's Journey with Airbnb

32:17 to 40:44

Ryan shares his experience with Airbnb as a side hustle and how it helped grow his real estate portfolio.

“And so I had to convince my girlfriend at the time, but not wife.”

Lessons Learned from Mistakes

40:45 to 42:00

Ryan discusses his biggest rookie mistake in real estate investing and the valuable lessons learned.

“But since then, we invested in a duplex in 2024 and we just bought a triplex in 2025.”

Building Wealth through Basics

42:00 to 42:35

Learn about the fundamentals of building cash flow and wealth through real estate.

“every single person who's listening to this can probably follow as well.”

Connecting with Ryan Allsop

42:36 to 42:59

Discover how to reach out to Ryan Allsop for insights on real estate and film.

“Can you let everyone know where they can reach out to you and find out more information?”
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Transcript

Automatic transcript. May contain errors.

0:00Today's guest is a full-time filmmaker, but has a side hustle. It's bringing in$6 ,800 a month in pure cash flow from four rentals, all within walking distance of his house. Ryan Allsop didn't start with a trust fund or real estate experience. He bought a duplex to stop paying rent. Then he used HELOCs, local lenders, and even email-only deals to grow a full portfolio.

0:28This is the Real Estate Rookie Podcast. I'm Ashley Kerr. And I'm Tony J. Robinson. Okay. Well, let's give a big welcome to Ryan. Thank you so much for joining us today, Ryan.

0:40Real Estate Rookie:Happy to be here. Thanks for having me. So you're a filmmaker by day, but what made you start investing in real estate? Yeah. It's a long story. Going back, I grew up in a large family. I'm one of seven and kids. So, you know, we had a very nice, modest home. I remember growing up with three of us in one room. And so it was tight. And I remember in high school and middle school, my dad actually started to read. I remember rich dad, poor dad. And then he bought a fourplex. And I just saw, you know, we got a boat and we were able to do, you know, I think more things than I remember growing up. And that always stuck in my mind.

1:16Real Estate Rookie:And so when I finally got to the age of 26, I hated paying rent. And I said, I want to buy a duplex and have someone else pay for it. And so that's kind of how it all started. So you had this big realization that rent money could actually go towards ownership. So what year was this that you ended up buying this property and tell us a little bit about it? Yeah, this was April of 2017. And it was a duplex. And I just could see, okay, I did the numbers and I could figure it out the rent that I could get for the upstairs. It was a duplex. I was going to live on the first floor, had renters up above and that rent would pay for the mortgage insurance and it would pay for the taxes.

1:56Real Estate Rookie:So I knew I'd break even, but in my head, I was already paying$600 for rent at the other place. So I was like making 600. And it worked out really well. I got a 30 year fixed loan and it was a first time home buyer. So I only had to put 10 % down and it had no PMI. So it was a very affordable loan to get into my first rental. And Ryan, I guess I'm curious. I mean, it sounds like a pretty solid deal, but how did you find it? Was it listed on the MLS? Were you walking around the neighborhood? What was your secret to finding this first house hack? Yeah, I knew nothing. I knew nothing about real estate.

2:33Real Estate Rookie:So I just went on Zillow and I found the first duplex and I typed in my information and they paired me with a local lender totally out of the blue. And I went and toured it and it was a dump. It was terrible. Even the realtor was like, you don't want this house. And it's funny because that short interaction of happenstance now led to, she actually paired me up with her daughter who was just starting to be a realtor, amazing realtor here in the local Milwaukee market. And I've now used her to buy five separate homes since then. She is my go-to and it just all happened. And so for the first home she showed me after that dump, that was the one.

3:07Real Estate Rookie:It just happened to be, we had showed other ones after that. And I was like, no, no, no, no. That very first one that you showed me, that was the one. I was not expecting you to say that at all. I still can't believe it. The very first house that Paris is her name that she showed me was the one that I ended up buying. And that was the one that I lived in for many, many, many years. Brian, you say that your realtor said it was a dump and that you shouldn't buy it, but yet you bought it anyway. Why? What did you see? I apologize. I'm sorry. That very, very first place was a dump. And then the second one, which was the first one with Paris, that was the one I ended up buying.

3:43Real Estate Rookie:And that one wasn't a dump. It was distressed and it was definitely needed some TLC and some love, but it was within my price range. And so I ended up buying that second one I toured. Going into it, your goal was to house hack, but did you run any analysis to say like, okay, the numbers make sense on this? Or was it more just emotional? Like I like the way that it looks and I see the potential. How did you analyze that deal to know whether or not it was worth pursuing? Going into that, I knew nothing about real estate. I really didn't know numbers. I didn't know. I didn't even know house hacking.

4:14Real Estate Rookie:I did. All I knew is, OK, the mortgage is going to be about this much. And I think I can get about this much in rent because I'm paying this much for rent a couple blocks away. And so, you know, I was I was a rookie. I didn't I didn't do much calculations, to be honest, besides that. I had a good feeling about it. But a big thing for me was I just hated paying rent. I hated I'm a very frugal guy and I just hated paying rent and losing all this money every month and having nothing to show for it. So that was a driving factor for me. And it was kind of one of those things of this. I got to take I got to take the first step and I'm going to figure this out along the way.

4:48Real Estate Rookie:I don't know how to be a landlord. I don't know how to manage all this. I think the numbers are going to work, but I just took a leap of faith. I love that you used the phrase leap of faith, because I think where a lot of rookies get stuck, Ryan, is in the dreaded analysis paralysis, where they listen to the Real Estate Rookie podcast. They watch the YouTube videos, they read the books, but they never actually get to a point where they're able to take action. What fears or limiting beliefs did you have, Ryan, before you got started? Because we all have them. And how did you actually overcome those to secure that first deal?

5:24Real Estate Rookie:I'm a frugal guy. And that down payment was$27 ,000. And nowadays, maybe that doesn't sound like much, but I was 26. I was scrapping and I was working a W-2 and I was also So a server, I saved up that money for years. That was my entire life saving. So it was a massive decision. And it was so scary to put that down. And, you know, I knew I had to do something. And this felt like the most calculated way to take a risk, but still be confident that the outcome will be very beneficial for me and for the future. And I'm a big person for being able to do something for myself in the future. And so I knew my future self was going to appreciate this move that I took now.

6:13Real Estate Rookie:And I know they're just saying that, it appears a mile wide, but only an inch thick. And it's all about taking that first step. And I just knew, I just had a feeling this was going to pay off in the long run. Where did this property end up? So did it actually pay off? Were there struggles? Did you have to sell it? Tell us what ended up happening with this property. Yeah, this property honestly will be the one that I will remember forever as being the best decision of my life. It was great. Everything was great. The first year I got a great group of girls that lived above. My girlfriend at the time moved in with me below.

6:48We were like very friendly with each other.

6:51Real Estate Rookie:They ended up living there for like four years. It was the best situation. No turnover in four years. That is like a landlord's dream. You're telling me. And it was the best case situation, which I know often on many podcasts, you don't hear from the very first interaction to step into real estate. But those tenants were amazing. We would even split the cable and internet bill. So even other aspects of my life got even more affordable. It was so great. And we'd leave for the weekend and they'd make sure the house was good. And it was a great, great decision because now since then, I've used that house as collateral to get a HELOC, which then I pull out more money and I get another property.

7:29Real Estate Rookie:And now, you know, I've since left that property. But before leaving, I refinanced it as a owner occupied 30 year fixed rate at 3%. And that was in 2021. And so now and then I moved a couple months later. So, you know, I locked that in for 30 years with a super low payment. And so that one is, you know, kind of the cash cow. That one's doing really good and set up long term. I think it seems like one of the things you may have realized is that even though this was a great deal to start with, the real power of this property is the long-term play. You just explained exactly what you have been able to do with it besides just having cash flow.

8:11And I think that is something I definitely learned over the years that it's not just cash flow. As you hold these properties longer, there is so much more value to them that you can tap into and that the equity, the appreciation, the mortgage pay down, all of that can give you longer term benefits of the property. Like I look at some properties that I've owned and, you know, I've had them for 10 years now and it's like, wow, that is a lot of money that is in these properties that I have access to. I could do the HELOC, I could do a cash out refinance, or I could sell the property. and we see in the BiggerPockets forums all the time that dilemmas, but the thing with these dilemmas is that these are opportunities.

9:00No matter which one of those options you picked, it's going to have some kind of benefit to you. These are good choices. These are good options to have. And so I think that's just such a great, wonderful realization of real estate is that at the buy can be great, the buy can be okay. But like what the real power of these properties is, is that long-term play of what you realize what else you can do and what other opportunities become available to you. And actually, I think it's, it's harder for rookies to understand that because we live in an age where everything is sensationalized and things only get traction if they're, you know, attention grabbing and the hook has to hit and social media paints a certain picture of why we invest in real estate.

9:47But what it really comes down to is exactly what you just said. It's a long game in the same way that people invest in the stock market, in the same way that people put into their retirement accounts. Real estate is a long-term vehicle for wealth, not just a, hey, let's try and get rich overnight, because most of the time that doesn't work. So Ryan, thank you for illustrating that point so strongly.

10:10Real Estate Rookie:Yeah, I see it as, and I don't know if others will, but I think real estate is just the most simplest form of self-love. You know, it's embracing, you know, delayed gratification. And it's living below your means so you could build up some equity. And, you know, it's not a sacrifice. I think it's more of a strategy. All right, coming up, Ryan's going to share how he negotiated an entire duplex over email and how he used very little of his own cash to get his next two deals. Most deals don't fall apart because of the numbers. They fall apart because of the financing. You find a property that cash flows.

10:45Real Estate Rookie:The deal makes sense. But then the lender looks at your personal income, your tax returns, your debt to income ratio, and suddenly the deal doesn't qualify. That's the disconnect. Because as investors, we're not buying based on our W-2. We're buying based on the asset. That's why Host Financial offers DSCR loans designed for real estate investors, where qualification is based primarily on the property's income, not your personal finances. So no W-2s, no tax returns, and no DTI requirements. And with loan-to-value options up to 80 or even 85 % on eligible deals, you can keep more capital available as you grow.

11:27Real Estate Rookie:If you're buying rentals, refinancing, or scaling your portfolio, go to hostfinancial.com. That's H-O-S-T That's VFINANCIAL.COM and see what you qualify for. We talk a lot on the show about financial freedom. And for some of you, that means eventually having the choice to walk away from your W-2. But there's one expense I think a lot of investors underestimate when they're calculating their financial freedom number. Health care. Because once you're paying for health insurance yourself, you might suddenly be looking at hundreds or even thousands of dollars every month. That's a lot more cash flow your portfolio needs to produce before you can comfortably leave your job.

12:03But here's something you may not know. Health insurance isn't your only option. WeShare Health is a non-profit alternative to health insurance, and their members pay up to 60 % less than they would for traditional health insurance. You still get access to a nationwide PPO network with over a million physicians plus unlimited telehealth. So if healthcare costs are making your financial freedom number feel a little further away, run the numbers on another option. Call 1-888-WESHARE for a free quote. That's 1-888-WESHARE. Or visit WeShareHealth.org.

12:37Real Estate Rookie:Do you ever notice how every passive investment somehow turns into a very active lifestyle? Active spreadsheets, active phone calls, active stress. Here's a better question. What if you could buy brand new construction homes, 10 % below market value in the best markets across the country without making real estate your second job? That's exactly what Rent to Retirement does. They're a full service turnkey investment company handling everything for you. In some cases, investors get 50 to 75 % of their down payment back at closing, plus interest rates as low as 3.75%. They've partnered with BiggerPockets for over a decade, helping thousands invest smarter.

13:14Real Estate Rookie:If you want to do the same, visit biggerpockets.com slash retirement to learn more. I do want to talk about my first rental. I thought collecting rent would be the hardest part, and I was actually wrong. The admin never stops the expenses, the receipts, tax forms, tenant issues. I didn't expect the behind-the-scenes work to take up so much of my time and headspace. Every night was another round of paperwork, and I started thinking, If it's like this one, how do people handle five or 10? Baselain helped me get out of the weeds. It's the official banking platform of BiggerPockets that handles the whole backend for me.

13:50Expense tracking, financial reporting, rent collection, even tenant screening. It's the first time I've felt in control and now that I'm not drowning in admin, I finally see how my real estate business can scale. So do yourself a favor, sign up at baselain.com slash VP today and get a$100 bonus. All right, guys, we are back with Ryan and he just told us about the deal that changed everything for him. The best deal, the best decision that he's ever made was buying that first duplex. But Ryan, you don't stop there. You keep going. And I hear that you bought a second duplex by negotiating entirely over email, which is every introvert's dream.

14:29So what's the story? How did you do that?

14:31Real Estate Rookie:Yeah, this was two years after that first duplex and I was itching to get another. I still at this point was still a rookie. I didn't know much. So I was touring new ones, trying to find a new one. This was in 2019. I was asking around and it just so happened that my now wife's friend's friend from college had a friend whose dad had a property on the campus who went to Marquette University and put me into contact through email. And one thing just led to another to another to about a hundred emails later. You know, I probably wouldn't have done this nowadays, now that I know what I know, it sounds like a scam, but it worked out that we just kept going back and forth.

15:08Real Estate Rookie:And he said, I want this price. And I would email back, I'm more on this price. He would email back this, this, this. And we got to a work, kind of a middle ground. And he had an attorney and I had to figure out, I needed to hire an attorney too, to represent me and do all the paperwork. And it worked out. I tell that story to people nowadays and I just thought I was thinking, but it worked out. I just took the leap of faith and I went for it. Ryan, what was a big difference from buying a property on the MLS, having a real estate agent to now negotiating a deal without an agent? A lot of people wouldn't know what to do because a real estate agent does really hold your hand and walk you through those steps.

15:47So if a rookie is in a similar situation where they have a deal that's off market, what are some of the things they should do right away to actually move this deal forward without a real estate agent?

15:57Real Estate Rookie:Yeah, it was definitely nerve wracking because I was still new to this. I didn't quite know everything, the ins and the outs. And I'd only gone through one and it was property and that was two years ago. So I toured it right away. I just wanted to make sure, okay, I'm talking to this guy via email. Is this legit? Is this real? I go there and he has a property management company. So I meet with the manager, ask her a bunch of questions. I came prepared with a bunch of questions, verified the leases, verified the rents, verified everything that he was telling me, saw it for myself in my own eyes, toured the property and everything checked out.

16:27Real Estate Rookie:All the boxes were checked. you know, you have that feeling in your stomach. Is this real? Is this, you know, am I getting scammed? But no, everything checked out. So it's just about doing your due diligence, making sure the numbers check out, you know, the leases are accurate, talking with the property manager, and really just going through everything to make sure it's real. I think we've all heard the story of like the Nigerian prince who, you know, they need you to wire X number of dollars and they'll change your life. So I'm glad that didn't happen to you. But I wanna go back to you just getting connected to this person in the first place.

17:01So you said it was your wife's friend of a friend of a friend whose dad did this thing. Like how did, you know, this is someone who's, you know, maybe five, six degrees of separation from Ryan. How did they know that you were a real estate investor and how did it make it all the way back to you?

17:16Real Estate Rookie:Yeah, and so I got the email, it was actually at a party. It was like a birthday party and we were just talking and my wife talked to her friend and she's like, I know this person. And I got his email. So I reached out to him directly. And I said, this is who I am. I'm a real estate investor in Milwaukee. And the story was he had wanted to sell it because he bought for his daughter. But he lived in Seattle and the house was here in Milwaukee and he had had it just under management and now just didn't want it anymore. But it was a beautifully fully gutted and renovated home only three years past renovation.

17:44Real Estate Rookie:So it was flawless, didn't need anything. And he said, yeah, you know, I thought about putting on the market, but I've just been so busy. What would you give me for it? And that's how the conversation started. And we just snowballed from there and finally got to a price that was mutually agreeable. I think about that as far as like, I was going to put it on the market, but then I just got too busy. And I can see a lot of investors or even just homeowners in that same situation. It is a lot of work to list a property, to have the agent come out, schedule photos of the property for the agent to tell you, you need to change this, change this, change this because the house is going to sell better.

18:25You need to do these things, uh, set up showings on your property. Like it isn't sign the paperwork, get all of the information to the agent, fill out all the disclosure forms of what's wrong with the property, what's not wrong, all these things. So like, I can totally get that. And I think another thing to point out too, is that, you know, your wife must've been talking about what you're doing for somebody to know about this and word of mouth referrals of just saying what you're doing, not even saying like, Hey, I'm looking to buy a deal if you know someone, but just talking about what you're looking for.

19:02I have gotten, when I first started, probably 50 % of my deals were from word of mouth, like a friend's sister whose brother-in-law was, you know, sick of tired of being a landlord, you know, I bought their property. So I think that is such a good lead generation. It shouldn't be your only way that you're getting deals, but it's definitely, it can be a really big beneficial one. So tell people what you want to do or what you're currently doing. And Ashley, I just want to add to the point too of why this person sold to Ryan without listing. And I think the takeaway from Ricky should be, you should never assume the motivation of a seller because there are a million, an infinite number of reasons as to why someone should sell.

19:48But I think what you should do is try and understand what that motivation is. And in this seller's instance, it was the convenience of being able to talk to one person and to be able to get the deal done. And I think the more you know about their motivation, the better you can position your offer to solve whatever problem they have. I've shared this story on the podcast before, but we've actually had multiple guests who have had similar situations, but someone that we knew or that we interviewed got a really great deal on a home from this lady because she had been in that house for like 40 years and she didn't know how to move.

20:24She had never moved before. And she was like, look, I'll give you the price if you can just help me move. And all they had to do was pay a moving company, you know, a couple thousand bucks to help this lady move and they got a killer deal. So anyway, understanding the motivation of the seller, I think is super important. But Ryan, going back to your story, you find this amazing deal. You said it was turnkey, but have you matured or I guess progressed, maybe is a better word, onto taking on projects that did need some renovation? And if so, how many of those renovation type projects have you done so far?

20:55Real Estate Rookie:Yeah. I like to do a renovation project every year per property now. And that one is definitely turnkey and they're kind of smaller. But at each one of my properties, I like to at least invest one to 3 ,000. When I first acquire a property, I like to put at least around$5 ,000 into it. And I just think it's going to increase the rent. It's going to show the current tenants, I'm here. I care about this property. I want a great home for you to call home. And it's just a little aesthetics around the house to really help improve the quality of life for the tenants and then set that property up long term.

21:30Real Estate Rookie:I'm all about setting the property up. If something's broken, I'm going to fix it right away, get it going. And then hopefully it's nice and it can kind of coast for a couple of years. Now, Ryan, how are you financing these properties? You did the first one as a primary residence to house hack it. What about these other properties that you have acquired? Yeah, so for that second property, that was the scariest moment of my life. And so for that one, the purchase price was around$337. And I looked around for rates and low down payments. I couldn't find anything less than a 25 % down. So I needed to come up with around$80 ,000, and I didn't have it.

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22:08Real Estate Rookie:but I knew that I wanted this property. And so I got a home equity line of credit on that current very first duplex that I had. And I had all my life savings from that two-year window from that first one to the second one was around maybe 50 ,000. And then I used the HELOC for the 30, 35 ,000. And so I was taking a massive gamble and I knew I was going into massive debt and putting it all on this one property. And I had done the numbers. I knew it was going to work. And so the day we closed, I handed over this check for$85 ,000. And then immediately after there, I drove to a jewelry store and I bought my wife's engagement ring, which was thousands and thousands and thousands of more dollars.

22:48Real Estate Rookie:And we were leaving in two days to go for a two week trip in Spain where I was proposing. So that trip again was thousands and thousands of more. It was so nerve wracking. I did the math. I was like, I spent over$100 ,000 today. And I don't even make half that in a year. I was so, you know, I had done the math. I mean, it was, that was one of the most scary moments, but it was, it paid off great since then. And it just, I think it's taught me to bet on myself, do the numbers, do the research, you know, make sure everything, no stone is unturned and then be confident with the decision and move forward.

23:21Real Estate Rookie:and everything's worked out. But that was such a nerve wracking day there to the jewelry store and not knowing how I'm getting any of this money paid back, hoping that it all works out, but it did. All I can think about is, I don't know if you guys ever watched Parks and Recreation, but two of them are like, treat yourself and they have the treat yourself day and they just go and buy everything. And that's what I think of, except you made investments, investments in a wife, investments in yourself and personal care and vacation and property. So I guess a wife is in a way, a spouse is in a way an investment.

23:56So I've never, I've never framed it that way. Hopefully, hopefully you're getting a good return on that investment, Ryan. Fingers crossed. I feel like there's going to be very mixed opinions on me saying that if people agree or disagree. Okay. So everything that you have bought has been in the same Milwaukee area, correct? Have you bought anything anywhere else?

24:17Real Estate Rookie:No, I've doubled down on the market. I've thought about elsewhere, but I know the rents. I know the market. I know the housing. I just feel like I'm so knowledgeable in that area that, you know, leaving to go to another market or Madison, Wisconsin or Chicago, you know, somewhere still kind of within the Midwest. And I just have to relearn that market. And I'm all about doubling down on tried and proven strategies. So that's why I continue to buy the next duplex in the market. And now I bought a house that's three houses down from the other one. And I just bought another one that's across the street from that other duplex.

24:51Real Estate Rookie:So I tend to just buy them in these areas. And I'll just continue to kind of buy in this neighborhood. Ryan, I think to your point, there is a tremendous benefit to going deep into one market because you pick up an expertise that's hard to do otherwise. But I think if I were to play devil's advocate, and I'm curious what your take is on this or how you've kind of reconciled with this, the downside to going so deep in one market is that you are more exposed to maybe different shifts within that market economically. You know, like if you think about cities across the United States where maybe, you know, a manufacturing plant closes and people, you know, a good percentage of the population loses their income.

25:38If maybe there's oversupply, say that the city of Milwaukee starts overbuilding multifamily housing and now rents are coming down. Like there are different economic factors that could impact a city. How do you reconcile with maybe the risk that comes along with investing so deeply in one market with those benefits?

25:56Real Estate Rookie:specifically pick an area it's on the east side of milwaukee that has always been a trendy spot it's close to the lake there's a lot of restaurants bars and a lot of the tenants i do are young professionals to 30 year old people and they want to be downtown they want the lively you know being able to walk to the restaurants and the bars and walk to the lake and that's the area that i really have focused on and because i've been in milwaukee for now i think close to 15 years i went to college here. And so I lived in these neighborhoods through college. I lived in these areas. I've lived in this area for 15 plus years.

26:30Real Estate Rookie:And all throughout that time, I've seen the rents go up and it's been steady and it's the most desirable area because it's fun and a lot of stuff to do. And so I back up my decisions with that, knowing I've seen it for 15 years. I know the growth is there. I know that even if it comes down, this is where people want. This is the area that the crime is low. And I think focusing on an area that has the least risk like that has definitely helped me strategically position where I want to buy. I feel very confident going forward that they're set up long-term in this neighborhood and area will always be great.

27:08Up next, we're going to find out how Ryan made 10K Airbnb-ing his own unit, but also got burned by a Craigslist contractor and what he's planning for his next big leap into 12 plus units. We'll be right back. An Airbnb deal can look great on paper and still become an expensive mistake. B &B Calc makes the numbers prove the deal. Use B &B Calc's market map to browse over 10 million Airbnb and VRBO listings, compare cities by revenue and gross yield, spy on top operators, and build comp sets. See how adding amenities like hot tubs or EV charges can boost your revenue. Enter any address to generate a complete property report.

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31:33Real Estate Rookie:Do you ever notice how every passive investment somehow turns into a very active lifestyle? Active spreadsheets, active phone calls, active stress. Here's a better question. What if you could buy brand new construction homes, 10 % below market value, in the best markets across the country without making real estate your second job. That's exactly what Rent to Retirement does. They're a full-service, turnkey investment company handling everything for you. In some cases, investors get 50 % to 75 % of their down payment back at closing, plus interest rates as low as 3.75%. They've partnered with BiggerPockets for over a decade, helping thousands invest smarter.

32:10Real Estate Rookie:If you want to do the same, visit biggerpockets.com slash retirement to learn more. okay welcome back we are here with ryan so ryan you decided to pivot a little bit and you used airbnb as a side hustle how did that actually help you grow your portfolio that helped me immensely this was back in 2017 when i first bought that duplex and airbnb i still feel like it wasn't what it was now and it wasn't what it was in 2020 uh and i had heard about it and i I said, let's do it. And so I had to convince my girlfriend at the time, but not wife. And so we rented it out for a weekend. And it went great and made some good money.

32:50Real Estate Rookie:And then we doubled. It was$100 that first weekend and said, OK, maybe we can get more. And we did$200 the next weekend, booked it right away. $300 the next weekend, booked it right away. And we're like, OK, we can make some serious money as we kind of tested out the pricing and had great experiences. And as a filmmaker myself, I had a film that was playing across festivals across the country. And so we got into this habit of, all right, we're going to this film festival in Houston. We're going over here to L.A. We're going to New York. And we would rent out our house on Airbnb and make about a thousand dollars for three days.

33:21Real Estate Rookie:And we'd go to these towns and we'd book a hotel and it'd be for the whole weekend. We'd spend 800 bucks. And so we would make money leaving, being able to go to these festivals while our place is being rented. And it was a magic time, I guess, because I don't know about nowadays we'd have the same demand or price that we could. But it was a great habit and lifestyle that we had at that moment that we could then use that money to supplement fun experiences, but also build up our life savings. And a lot of that then went to the next property. Ryan, what are some of the things that maybe you did do or didn't do?

33:53But if a rookie investor wants to do the same thing, just rent out their primary residence on Airbnb, what are some of the things you have to do or maybe like some hacks to make it easier? Like, I'm just looking around right now. Like, okay, I got a kid's toys there. I got books here. I got this right here. Like, what are some hacks to make it easier to rent out your property and it still be your own home?

34:20Real Estate Rookie:Yeah. I think number one was, I mean, they took us a little bit ago, but they're sleeping in our bed. And so, you know, we bought brand new sheets off Amazon for every bed in the house. So there was the Airbnb sheets and the bedding for the Airbnb. And then there was our stuff. keeping that separate was nice keeping the amenities there and then you know we would take away and we'd you know take away the photos or take away certain stuff and stuff like that which took a few minutes every time we had a booking but we just kept it clean kept it organized and and just I think it comes down to communication I think it's just treating people helpful you know give them suggestions of where to go into town and this a lot of people coming to Milwaukee wanted to you know go to festivals or concerts and you know giving them suggestions on where to park, where to eat, where to drink.

35:05Real Estate Rookie:But prepping the house, you know, we would put out blankets, we put out extra pillows, extra towels, having those extra amenities like that, I think helped in with a lot of the groups that we had. I really have wanted to like test this out to see like, okay, with kids, how can I just experiment? I listed on there for one week or whatever, and to see what happens because like, I want to prove that anybody could do this. But I'm also very much like germaphobic where I 100 % would have to do. They have their own towels. They have their own linens, like things like that. But I think it would be super easy, like, especially if you have more than one bedroom to take one of those bedrooms and to lock it off and you put your personal things in there.

35:51And, you know, I did see this family on Instagram that every summer they leave their house and they're like, I don't know, had like five kids or something and they put everything in one room. Like they showed videos of them, like packing up everyone's clothes, everyone's toys from the rooms. And they just do like big bags and big bins. They're all labeled and they go into that room that's going to be the storage. And then they rent out and they said, that's how they pay for their two month vacation is renting out their house and they get to experience all these things and travel. So I'm like really tempted, tempted to do it, but also in the middle of renovating my live and flip.

36:27So maybe once it's done then, because like, I don't think so. An Airbnb guest is going to be happy to walk in and see there's no trim in the hallway right now. But yeah, I've seen folks do it that exact same way where they just pick one room in the house and that's where they stuff everything. And then when they come back, they unload. So that, that could be the strategy for folks who are, who are looking to replicate that. But like me and Ash, you got multiple kids and other folks flying around as well. Um, so it sounds like the Airbnb was successful for you. The, the, the small multifamily properties you've been buying have been successful for you.

36:59But what about the mistake, Ryan, what would you say is your biggest rookie mistake?

37:04Real Estate Rookie:On that first duplex, you know, and when I was starting out, I didn't know everything about everything. And I ended up hiring a contractor off Craigslist, which I've never done since. And, uh, he burned me. He acted all nice, friendly, demoed part of the bathroom, started to do some tile and ended up paying him in portions and ended up paying him the ending too soon. And he left, never saw him and ended up having to hire someone to come back. And they said he did this terrible and they had to rip off the tile, rip off. And it ended up costing more money than it would have just been to go with a reliable company.

37:44Real Estate Rookie:And, you know, like I said, I'm a frugal person. And so I was trying to cut corners, trying to get the cheap, you know, bathroom reno. And and I learned a valuable lesson of. In my in my opinion, don't trust anyone on Craigslist, you know, and make sure you go through the vetted people, you know, you know, and don't pay people the entire amount until the work is done. You know, I paid him most and he said he was almost done and that if you could get the final amount, it'd be great. And he was all nice and said, all right. And he gave me some sad story about how he needed the money. And, you know, you want to trust people, you know, you want to.

38:21Give him the benefit of the doubt. But there's that saying, though, that you have to choose between speed, cost and quality. And you can only choose two of those. So you can have someone who's fast and cheap, but then you're probably giving up the quality. You can have someone who's fast and great quality, but then you're probably giving up the cheap cost. But to get someone who satisfies all three equally is probably non-existent. So for all the rookies that are out there, sometimes it pays to wait for the contractor who's booked out because there's a reason they're booked out. It's because everyone wants them.

38:58And the contractor who's like, yeah, I can be there tomorrow. maybe there's also a reason why they can be there tomorrow and they're not working. So I, I appreciate you sharing that because I've been burned by contractors in that same way. We're like, do you have a pulse? Can you be here tomorrow? Yes. Okay, great. You know, and then you end up having to pay someone else to fix their work.

39:14Real Estate Rookie:Yeah. And I think this in the end, it ends up costing more money and it's more stress and it's more headache and more heartache when it goes awry. And I just, it's, it's halo more for that, that, that peace of mind that you, this is reliable. It's going to get done good. And, uh, you don't have to stress about it or worry that they're going to run off. Well, I've got to say, I have had one Craigslist experience in my life. I actually bought goats off Craigslist and they are the most wonderful things ever. So my experience is very different than finding a bad contractor on Craigslist. But Ryan, what is next for you?

39:53I guess, first of all, what are you, what does your portfolio look like today? And then what's next? Yeah.

39:59Real Estate Rookie:And so I bought those first two duplexes and then me and my wife got married and now wanted to start a family. So we needed to move out of that first level of that duplex, sadly. And so we bought a single family home just outside of Milwaukee, where we currently live. And, you know, real estate, I see funded that. And now I see it as a way of I do the numbers of what the real estate business is. But then I also love seeing it. Okay, it covers all the costs of this home where we live in our dream home. And we still cash flow. And, you know, me and my wife, you know, we live for free technically here, you know, because real estate is paying for us to live here.

40:32Real Estate Rookie:And that's been one of the, I think, you know, joyous moments of realizing the hard work and those risks and those first few duplexes I bought are like paying off because here we are in our dream home and we love it here. But since then, we invested in a duplex in 2024 and we just bought a triplex in 2025. And with those, I used the home that we live in now, got a home like we line of credit on this property now and pulled out a bunch of money to help fund the down payment on those other investment properties that we've bought since. So I love using HELOCs, especially in the climate that we're in now where I have 3 % rates on my properties and I don't want to, you know, touch that at all.

41:13Real Estate Rookie:But being able to get the home equity line of credit and using this as leverage to acquire more properties and really try to scale up the portfolio faster. Ryan, you know, your story reminds me a little bit of Chad Carson, who we've had on the Ricky podcast a few times where Chad doesn't necessarily do anything super outrageous or quote unquote sexy. He doesn't have like any super secret strategies where, Hey, this is the, you know, this is the hot new thing. He just makes very simple strategic decisions. And it just compounds that over and over and over and over again. And what you did was a very simple path.

41:51it wasn't complex. Now I'm not saying that it was easy because obviously there were challenges along the way, but in terms of complexity, the path that you've laid out is a path that virtually every single person who's listening to this can probably follow as well. Save money, work hard, be frugal, house hack, refinance, HELOCs, do it again, and just repeat that process until you have enough cash flow to go out there and buy your dream home. So again, we live in an age where everything has to be new and sexy. And, and, you know, here's the greatest thing you've ever heard of since sliced bread.

42:24But if you just go back to the basics and you focus on that compounding over time, great things tend to happen. So kudos to you, man. It's amazing that what you've been able to accomplish in a relatively short period of time. Yeah. Ryan, thank you so much for joining us. Can you let everyone know where they can reach out to you and find out more information?

42:41Real Estate Rookie:Definitely. Yeah. I'm on Instagram and I do have a website there for my filmmaker profile and then kind of for a lot of the work that I've done with that. But it's a great way that people can still contact me. So it's Ryan all stop. Film. And that's my tag on Instagram. And then also Ryan all stop. Film is the website that I have. And if you message me through there or DM me on Instagram, I do a lot of real estate stuff and also film and videos as well. Well, this has been another episode of real estate rookie. I'm Ashley. He's Tony. And thank you guys so much for joining us. We'll see you on the next episode.

From the publisher

You can still get rich buying “boring” rental properties. Today’s guest pockets $6,800 in pure cash flow every month and is building an enormous amount of equity in four small multifamily rentals, and he’s not doing anything YOU can’t do. You don’t need a ton of money or even the flashiest investing strategy—you just need to get started and play the long game!

Welcome back to the Real Estate Rookie podcast! Ryan Allsop hated paying rent—so much so that he bought his first rental property without really knowing what he was doing. But with some rookie-level analysis and savvy networking, Ryan found that first duplex, which has been his “cash cow” ever since. Then, Ryan used home equity lines of credit (HELOCs) to scale a real estate portfolio that delivers nearly $7,000 in combined monthly cash flow!

Want to copy Ryan’s success? In this episode, he’ll show you the steps he took to go from complete beginner to confident investor in no time. You’ll learn about the real power behind buy and hold investing, a lucrative Airbnb side hustle you can use to fund deals faster, and a surprisingly effective way to negotiate with sellers—without ever picking up the phone!

In This Episode We Cover

How Ryan makes $6,800 in monthly cash flow with just four rental properties

Using the buy and hold strategy and “delayed gratification” to pay your future self

Scaling your real estate portfolio through home equity lines of credit (HELOCs)

Critical mistakes to avoid when hiring a contractor for your renovation projects

The easiest (and cheapest!) way to find off-market properties for sale

Living for free by having someone else pay down your mortgage for you

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-587

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