Tony J. Robinson (2:19)

Ran, I guess I'm curious, I mean, it Sounds like a. Like a pretty solid deal. But how did you find it? Was it. Was it listed on the mls? Were you walking around the neighborhood? What was your secret to finding this. This first house hack?

Ryan Allsop (2:29)

Yeah, I knew nothing. I. I knew nothing about real estate, 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, 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. 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 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.

Ashley Kerr (3:14)

I was not expecting you to say that at all.

Ryan Allsop (3:16)

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.

Tony J. Robinson (3:26)

Brian, you. 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?

Ryan Allsop (3:34)

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. And that one wasn't a dump. It was. It was distressed and it was definitely needed some TLC and some love, but it was within my price range. And. And so I ended up buying that second one I toured.

Tony J. Robinson (3:53)

Did you. Going into it, your. Your goal was to house hack, but did you. Did you run any analysis to. 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. What was your. How did you analyze that deal to know whether or not it was worth pursuing?

Ryan Allsop (4:09)

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. I didn't. All I knew is, okay, 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 paid 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.

Ashley Kerr (4:40)

So.

Ryan Allsop (4:41)

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. 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.

Tony J. Robinson (4:55)

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. 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?

Ryan Allsop (5:24)

I'm a frugal guy, and. 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 W2, and I was also server. I. I saved up that money for years. That was my entire life savings. So it was a massive decision and it was so scary to put that down. And. And it, you know, I knew I had to do something and I. 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. I'm a big. I'm a big person for self, you know, you know, being able to do something for myself in the future. And. And so I knew my future self was going to appreciate this move that I took now. And. And I know there's a saying that, you know, it's a fear of mile wide, but only an inch thick, you know, and it's. It's all about taking that first step. And I just knew. I just had a feeling that this was going to pay off in the long run.

Ashley Kerr (6:24)

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.

Ryan Allsop (6:33)

Yeah, this property honestly will be the 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. We were like very friendly with each other. They ended up living there for like four years. It was the best situation.

Ashley Kerr (6:54)

No turnover in four years. That is like a landlord's dream, you're telling me.

Ryan Allsop (6:59)

And it was, it was the best case situation, which I know often on many podcasts you don't hear from the very first, you know, interaction to step into real estate. But those tenants were amazing. We would even split like the cable and Internet bill. So even other aspects of my life got even more affordable. It was so great. And you know, they would, you know, 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. 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.

Ashley Kerr (7:52)

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. And 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 the, 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. Could do the heloc, I could do a cash out refinance or I could sell the property. And we see in the Bigger Pockets forums all the time that dilemmas but the thing with these dilemmas is that these are opportunities. No matter which one of those options you picked, it's going to have some kind of benefit to you. Like 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.

Tony J. Robinson (9:29)

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. But 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 and the same way that people, you know, put into their retirement accounts. Like, like real estate is a long term vehicle for wealth, not just a, hey, let's try and get rich overnight. Because most times that doesn't work. So Ryan, thank you for, for illustrating that point so, so strongly.

Ryan Allsop (10:10)

Yeah, I, I, I see it as, and, 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, it's living below your means so you could build up some, some equity. And you know, it's not a sacrifice. I think it's more of a strategy.

Tony J. Robinson (10:27)

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.

D (10:37)

I used to think I could booby trap my house like some scene from Home Alone, but it turns out setting up swinging paint cans can be pretty messy. And so I personally turn to a much better solution. Simplisave. I use it because it doesn't just react after something happens. It helps stop bad stuff before it even starts. And that's what makes it different and way easier than installing a zip line to my treehouse. Simplisafe's new active Guard Outdoor protection uses smart cameras and live agents who watch over your property in real time. So if someone's creeping around, they can talk to them, shine lights on them, and they can even call the cops if needed. It's like having a professional bouncer for your house minus the velvet rope. There are no contracts, no hidden fees, and setup is super simple. Plus CNET just named it the best home security system of 2025 and I get why. It gives me real peace of mind every single night. Right now you can get 50% off your new SimpliSafe system with professional monitoring and your first month free@simplisafe.com pockets. That's SimpliSafe.com pockets. There's no safe like SimpliSafe. What if I told you you could forget everything you know about investment property loans? Because Host Financial is rewriting the rulebook, tossing out those pesky DTI restrictions. They focus on your property's income potential. No tax returns or personal income statements needed. Simple, efficient and tailored for investors like you. Imagine a lender that sees the gold mine in your property, not just the numbers on your paycheck. That's the Host Financial difference and they're approved in 47 different states, so your next big deal could be just around the corner. Ready to unlock your property's true potential? Visit hostfinancial.com don't let old school lending hold you back another day. That's Host Financial. There's something surprising a lot of investors don't realize. Landlords actually file more insurance claims than homeowners. But most of the big traditional insurance companies, they're just not set up to handle those claims quickly or easily. That's why so many real estate investors are switching to steadily they focus exclusively on landlords. So whether you got a single family rental, need a builder's risk policy for a brrrr or focusing on growing your portfolio, you get fast quotes, flexible coverage and protection for property damage, liability and loss of rental income. It's a good idea to review your rates and coverages every year on your rentals. So go get a quote in minutes@biggerpockets.com landlord insurance today steadily Landlord Insurance for.

Ashley Kerr (12:56)

The modern investor 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 5 or 10 Baselane helped me get out of the weeds. It's the official banking platform of BiggerPockets that handles the whole backend for me. Expense 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@baselane.com BPtoday and get a $100 bonus.

Tony J. Robinson (13:49)

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. So what's the story? How did you do that?

Ryan Allsop (14:08)

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. It kind of who went to Marquette University and put me into contact through email. And one thing just led to another, to another, to about 100 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 and he said, I want this price. And I would email back, I'm more in 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. You know, I tell that story to people nowadays and I just thought, I was thinking, but it worked out. You know, I just took the leap of faith and I went for it.

Ashley Kerr (15:10)

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? You know, 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. So 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?

Ryan Allsop (15:35)

Yeah, it was definitely nerve wracking because, you know, I was still new to this. I didn't quite know everything the Ins and the outs. And I 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 rent, verified everything that he was telling me. Saw it for myself in my own eyes. Toured the property, and everything checked out. 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. Just going through everything to make sure it's. It's real.

Tony J. Robinson (16:25)

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, you know, they'll change your life. So I'm glad that didn't happen to you, but I want to go back to you just getting connected to this person in the first place. So you said it was your. 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?

Ryan Allsop (16:54)

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 it 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. They don't want it anymore. But it was a beautifully fully gutted and renovated home only three years past renovation. 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.

Ashley Kerr (17:37)

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 changes because the house is going to sell better. You need to do these things, set up showings on your property like it is, 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 have 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. I 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, 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.

Tony J. Robinson (19:07)

And Ash, I just want to add to the point too of, 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. But 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 you know, we've had actually have 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. She 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 have to do is pay a moving company, you know, a couple of 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, have you matured or I guess progressed maybe is a better word, onto taking on projects that, that did need some renovation and if so, how many, how many of those like renovation type projects have you done so far?

Ryan Allsop (20:33)

Yeah, you know, I like to do a renovation project every year per property now. And, and that one is definitely turnkey and, and they're kind of smaller. But at each one of my properties I like to at least invest 1 to 3,000, you know, and when I first acquire a property, I like to put at least around 5,000 into it. And I just, 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 just, you know, a little esthetics around the house to really help improve the quality of life for the tenants and then set that property up. Long term I'm, 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, you know, it's nice and it can kind of coast for a couple of years.

Ashley Kerr (21:16)

Now, Ryan, how are you financing these properties? You did, you know, the first one as a primary residence to house Hackett, what about these other properties that you have acquired?

Ryan Allsop (21:28)

Yeah, so for that second proper 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 more or anything less than a 25% down. So I needed to come up with around $80,000 and I didn't have it, 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 another 30, 35,000. And so I was taking a massive gamble and I knew I was going into massive debt and put 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. 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 and more. It was so nerve wracking. I did the math. I was like, I spent over a hundred thousand dollars today and I don't even make half that in a year. And 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 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.

Ashley Kerr (23:13)

All I could think about is, I don't know if you guys ever watch Parks and Recreation, but few of them are like treat yourself and they have the treat yourself day and they just go 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 a property.

Tony J. Robinson (23:30)

So I guess a wife is in a way, a spouse is in a way an investment. So I've never, I've never framed it that way. Hopefully, hopefully you're getting a good return on that investment, Ryan. Fingers crossed.

Ashley Kerr (23:39)

I feel like there's going to be very mixed opinions on me saying if people agree or disagree. Okay, so everything that you have, have bought has been in the same Milwaukee area. Correct. Have you bought anything anywhere else?

Ryan Allsop (23:55)

No, I've doubled down on the market. I, I, I've thought about elsewhere, but I, 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. You know, I just have to relearn that market and I just, 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, 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. So I, I tend to just buy them in these areas and I'll just continue to kind of buy in this, in this neighborhood.

Tony J. Robinson (24:35)

Ryan, I think to your point, there is a tremendous benefit to going deep into one market because you, you pick up an expertise that, 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, 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 if, if 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, with those benefits specifically?

Ryan Allsop (25:35)

Pick in area. It's on the east side of Milwaukee that has always been a trend, 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 lived in this area for 15 plus plus years. And all throughout that time I've seen the rents go up and, and it's been steady and it's the most desirable area because it's, you know, 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, you know, and I think focusing on an area that has the least risk like that has definitely helped meet strategically kind of 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.

Ashley Kerr (26:46)

Up next, we're going to find out how Ryan made 10k Airbnb being 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.

D (27:09)

Tired of traditional lenders holding you back? Host Financial is here to change the game. They've ditched the DTI restrictions and they zero in on what really matters your property's income potential. So no more chasing papers for tax returns or personal income statements. Think about it. A lender that values your property's worth over your paycheck? That's the Host Financial difference approved in 47 states. They are ready to help you make your next big move. Curious if you qualify? Just head over to HostFinancial.com and find out. Stop letting outdated lending practices hold you back. That's HostFinancial.com where your property's potential meets Unlimited Financing if you want a short term rental, here's something worth knowing. Not all landlord insurance policies are built for your kind of property, but that's where Steadily comes in. Steadily offers insurance designed specifically for short term rentals. They cover things like property damage, liability, loss of rental income, and even unexpected issues like bed bugs. Steadily only works with real estate investors so they understand the details that make short term rentals unique. And they've built coverages specifically for short term rentals. One investor pro tip I always like to give out is to review your rates and coverages every single year. So go get a quote in minutes@biggerpockets.com landlordinsurance today steadily rental property insurance for the modern Investor Attention landlords. Are you prepared for this year's peak rental season? If not, Avail is here to help you succeed. With Avail's comprehensive Rental analysis reports, you can set a competitive price informed by detailed market insights including pricing trends and local demand. Find great renters quickly through easy to create online listings that are syndicated to 20 top rental websites. Review prospective tenants applications online and screen instantly with transunion credit reports, background checks and evictions and history all at your fingertips. Need a lease? Avail offers lawyer reviewed templates specific to your state, ready to be signed online. Plus streamline your rent collection by accepting payments through your tenant's preferred methods, ensuring everyone stays on track. Make 2025 your best rental year ever. Visit Avail co Biggerpockets today to unlock your rental property's full potential. That's a V A I L CO BiggerPockets.

Ashley Kerr (29:24)

You just realized your business needed to hire someone yesterday. How can you find amazing candidates fast, easy. Just use Indeed. When it comes to hiring, Indeed is all you need. That means you can stop struggling to get your job notice on other job sites. Indeed's sponsored job posts help you stand out and hire the right people quickly. Your job post jumps straight to the top of the page where your ideal candidates are looking. And it works. Sponsored jobs on indeed get 45% more applications than non sponsored posts. The best part, no monthly subscriptions or long term contracts. You only pay for results. 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@inneed.com rookie, just go to indeed.com rookie right now and support our show by saying you heard about Indeed on this podcast. That's indeed.com rookie terms and conditions apply. Hiring Indeed is all you need. 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?

Ryan Allsop (30:46)

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. And I had heard about it and I said, let's do it. And so I had to convince my, 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. And then we doubled. It was a hundred dollars that first weekend and said, okay, 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, okay, 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 la, we're going to New York. And we would rent out our house on Airbnb and make about $1,000 for three days. 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.

Ashley Kerr (32:06)

Ryan, what are some of the things that maybe you did do or didn't do, but 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 kids 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?

Ryan Allsop (32:37)

Yeah, I think number one was. I mean, they were. Took us a little bit to go over this, but they're sleeping in our bed. And. 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. 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. But prepping the house, you know, we would put out blankets, you 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.

Ashley Kerr (33:31)

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 germaphobia, 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. And 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, the room that's going to be the storage. And then they rent out. And they said this is 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. So maybe once it's done then, because, like, I don't think so, an Airbnb guest is gonna be happy to walk in and see there's no trim in the hallway right now.

Tony J. Robinson (34:52)

But yeah, Ash, 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, 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. 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. But what about the, the mistake, Ryan? What would you say is your biggest rookie mistake on that first duplex?

Ryan Allsop (35:22)

You know, when I was starting out, I, I didn't know everything about everything. And I ended up hiring a contractor off Craigslist, which I've never done since. And he burned me. He acted all nice, friendly, demoed part of the bathroom, started to do some tile and ended up paying them in portions and ended up paying him. The ending too soon. And he left, never saw him, and ended up having to hire someone 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. 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, 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 he 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, I.

Ashley Kerr (36:35)

You want to trust people, you know, you want to and give them the.

Tony J. Robinson (36:39)

Benefit of the doubt. But there's that saying though, that, 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 rickies 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 is because everyone wants them. And 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 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. And then you end up having to pay someone else to fix their work.

Ryan Allsop (37:31)

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 comes to. Goes awry. And I just, it's, it's halo more for that, that, that peace of mind that this is reliable, it's going to get done good and you don't have to stress about it or worry that they're going to run off.

Ashley Kerr (37:49)

Well, I, 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 was very different than finding a bad contractor on Craigslist. But Ryan, what is next for you? I guess first of all, what are you, what does your portfolio look like today? And then what's next?

Ryan Allsop (38:15)

Yeah, and so I bought those first two duplexes and then me and my wife got married and, 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 cost 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. And, 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. 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, live in now, got a home equity 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 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. 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.

Tony J. Robinson (39:37)

Ryan, you know, your story reminds me a little bit of Chad Carson, who we've had on the Rookie 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. It 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 I, I, you know, again, we, 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. But 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 what you've been able to accomplish in a relatively short period of time.

Ashley Kerr (40:52)

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?

Ryan Allsop (40:58)

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 Alsop Film, and that's my tag on Instagram. And then also Rhinosup Film is the website that I have. And feel free, you can message me through there or DM me on Instagram. I do a lot of real estate stuff and also film and videos as well.

Ashley Kerr (41:21)

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.