Podcast Details

Episode 22

Andrew and Camala Winter

What if resilience and strategy are the true keys to success in the world of real estate investment? Andrew and Camala Winter, a dynamic duo in both marriage and real estate investing, certainly believe so. They join us on Hacking Real Estate to share their compelling journey from overcoming obstacles like a disastrous Airbnb experience and a car wreck, to thriving in the competitive property investment arena. Their determination and grit are truly inspiring and underscore the importance of resilience in real estate investment.

Andrew opens up about his portfolio, detailing his shift from Airbnb to long-term rentals and the unique strategies he used along the way. He shares his knack for turning houses needing a little TLC into prime properties and the advantages of pet-friendly spaces. Camala, on the other hand, tells us how she got into the game, her unique strategies, and the importance of happiness in their journey. Their experiences provide a wealth of insights, whether you are an experienced investor or a beginner.

Topping off the episode, Andrew reveals his latest venture, TrueRealio. This innovative platform aims to assist first-time home buyers and non-corporate investors in navigating the real estate market. They both highlight the vital role of providing quality homes for tenants and their future plans in the sector. Don’t miss out on Andrew and Camala's real estate journey; it's a thrilling ride filled with challenges, lessons, and triumphs, guaranteed to inspire you and equip you with practical insights for your own journey.

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Key Takeaways

1. Real Estate Resilience: The podcast episode tells the story of Andrew and Kamala Winter, a couple who faced several adversities, including Airbnb issues and personal mishaps, while investing in real estate. However, their resilience and innovative strategies helped them not only survive but thrive in the volatile market.

2. The Power of Adaptability: The couple transitioned smoothly from Airbnb to long-term rentals and successfully navigated the fluctuating market. They shared insights on their investment strategies, such as buying properties that need minor refurbishment and assessing the current and future market, proving that adaptability is key in real estate.

3. Launching TrueRealio: Andrew's latest venture, TrueRealio, is a platform designed to help first-time homebuyers and non-corporate investors. The platform aims to bring fairness, transparency, and equality into the real estate market, indicating a commitment to helping others navigate the industry successfully.


0:00:00 - Vikas Gupta

This is the Hacking Real Estate podcast, episode 22. 

0:00:04 - Andrew Winter

Just because it seems difficult, don't give up on it. And I'm saying that because right now you're seeing a lot of uncertainty in the housing market and I feel like the perception is don't even investigate because it's not worth it, and there's this sentiment that home ownership isn't for the next generation. And there are programs that exist if you look for it and if you work with a real estate agent. 

0:00:27 - Camala Winter

You know, if there's a will, there's always a way, and don't let fear be the reason that you don't do it. When I was in a tough situation, the way that I thought about it to get over my fear was what's the worst that can happen? And if you truly ask yourself what's the worst that can happen, you'll find that you have to take seven or eight worst case scenarios before you even get to that absolute worst case scenario, and in order to get there, so many things have to go wrong, and so purchasing a home is not likely the thing that's gonna derail your life. So that would be. My best advice is to really consider what is that worst case scenario and how many steps is it really going to take for you to get there? 

0:01:20 - Brandon Hall

Welcome to the Hacking Real Estate Podcast, where we dive into the stories of seasoned, hands-on and tech savvy real estate investors. We'll learn the strategies and tools they use to maximize returns and minimize hassle, all while navigating the rapidly changing real estate market. I'm your co-host, Brandon Hall, and managing partner of Hall CPA, and I'm sitting alongside my co-host, Vikas Gupta, CEO of Azibo. With our combined 15 years of experience in real estate investing and entrepreneurship, we're here to help you up your real estate game. Let's get hacking. 

0:01:52 - Vikas Gupta

Welcome everyone to today's episode of the Hacking Real Estate Podcast. Today, our guests are Andrew Winter and Camala Winter, and they are a husband and wife real estate investing to O'Base in Ohio and Florida Properties near Cleveland and St Petersburg. In addition to his full-time job, andrew was also working on launching TrueRealio, a platform to help first-time home buyers and non-corporate investors explore the realm of real estate, home ownership and investments. Welcome to the show. Thanks for being here. 

0:02:25 - Camala Winter

Thanks for having us. 

0:02:27 - Vikas Gupta

In your own words. Can you tell us your real estate journey? 

0:02:30 - Andrew Winter

Me first. So I started. I bought my first home in 2016. I was switching jobs and decided it was the time to lay down some roots and, unfortunately, that job no longer existed. So in 2017, I took the opportunity to go down to St Petersburg, florida, where I happened to. As a part of the deal I made, I got a bachelor pad $500 a month, top level apartment studio where I had a waterfront property like a pool, a workout facility and it was 500 bucks a month, but it was a part of it. I had to put my house up on Airbnb and offer a percentage of those proceeds to the person I was renting from. 

So that was my first foray in 2017 into Airbnb, where it went absolutely terrible. I mean, it was the worst experience I think I've ever had. I had people smoking marijuana in my house, I had parties thrown in my backyard, I made enemies with both my neighbors and I promised myself I'd never do it again. But I really liked snowboarding. So the second year I tried it. 

I'd made some tweaks and some changes. I found some good people to help me through and ultimately, that's what started my real estate journey, especially through Airbnb, and I also had the opportunity to purchase an investment property, my first one, where I learned everything there is to know about what can go wrong in a house. We purchased from a hoarder so, and then we also did a month lease back where she decided she wanted to not move and as a part of that journey there was the police were called. We had to renovate the entire home from plumbing to electric. So I really got my hands kind of really dirty really quickly into real estate, and that's kind of what propelled me into just continuing to replicate this. 

So every house I've purchased I've lived in and we've ultimately tried to make it a home for those that do call our homes home. And then my wife's story is a little bit different than mine. 

0:04:27 - Camala Winter

Yeah, I guess I got started in 2018 more out of necessity than anything else. 2018, I bought my first house using an FHA loan. So I put 3.5% down, which at the time was somewhere around like $3,000 or $4,000, which is really attainable. And I bought my first home because the next day I quit my job and in my mind I was trying to figure out how am I going to survive renting, because I was renting for $1,100 a month, every month, with no change in that. So how am I gonna survive without stable income? So logically, I thought you know, if I get this three bedroom, two bath house, I can rent it out. I can rent out one bedroom, I can rent out two bedrooms or I can rent out the whole place, but at least I can guarantee that I can have extra income every month. So it was really more for me to just ensure my livelihood, that house. 

Eventually I started doing my own coaching and consulting business and I really just had a really bad string of luck. I just was not going in my favor. I got down to what I call my $11 moment, where I had $11 to my name and had this breakdown where I was like all right, I guess we're putting the whole house up to rent because I can't afford it and that just kind of propelled and made my housing, I guess, my situation I don't know how to say that. I ended up having to just come up to Ohio with him and put my house up on Airbnb to survive. So that's how I got started. 

0:06:19 - Vikas Gupta

Was that string of bad luck real estate bad luck or non real estate bad luck? 

0:06:24 - Camala Winter

It was a little bit of both. I had a string of bad luck where I had someone sue me in my home. That wasn't necessarily my fault, which was just a really bad situation to start off with. And then, on top of that, I was down in Miami doing a coaching presentation and I was staying in an Airbnb and someone a drunk driver came in and totaled my car in the middle of the night while he was parked in a driveway, and so my car at the time was worse. What the insurance company told me was worth $8,000 and I owed $12,000. And so they really weren't gonna give me any money to get a new vehicle, and with $11 to my name, that math was just really not working out for me. So I took the insurance from my car, they gave me a rental for two weeks and drove up to Ohio and expedited putting my house on the market. 

0:07:27 - Andrew Winter

Where we lived in that second investment proper, or the first investment property that I ever purchased, we lived on the third floor, without air conditioning, with the dog that has separation anxiety disorder. So our beginning was a little bit rough but ultimately, looking back, it's really kind of was propelled us to be successful in this space, as we didn't start off with the greatest footing. We didn't have a lot of people come out and offer us a big lump sum of cash to get started in this. We really kind of clawed our way to where we are today. 

0:07:53 - Vikas Gupta

What compelled you to keep going? Cause I always find it really impressive when you know people have a few less than stellar experiences with an asset class or investment strategy and decided to keep going with it. 

0:08:08 - Andrew Winter

Yeah, I mean, it's funny. When I was 23 and I bought my first house like I had no support at all my friends all said you know why are you buying? It's terrible, like you know what homeownership is like. It's going to be a lot of work. You're going to have to mow the grass, you're going to have to like what happens if the plumbing goes out, what happens? The age back goes out. And I was like, oh well, I'll figure it out. I said you know it's an investment. You can invest in stocks or you can invest in real estate. 

And I said, ultimately I don't want to pay rent, cause to me I feel like it's throwaway. It's less of a hassle because you have somebody else dealing with it. Things go wrong. But taking that and moving through the chain, I saw a vision of myself kind of potentially starting up like a winter destinations, which we have a whole ton of puns on our last name for LLCs. It's really easy to do, but I wanted to get to the point where, if somebody from the North wanted to come down to the South, there was the ability for them to do so in a space that was friendly and was welcoming for them and that's all it's me where. 

When we talk about potentially the Kokina Keer Kingfish house, it was that space, and so I wanted to be a snowbird. I accomplished that at 26. And the only way to do that was to have environments that I knew I could do my professional day job and have a space that was conducive for me, being successful with that but then also potentially using it as an investment strategy. And so we have our primary residences in Largo, florida, but we're currently living in my first house that I ever purchased, which is Mind Over Center house up here in West Lake Ohio. 

0:09:32 - Camala Winter

I think Mind Over Center is a lot more simple than that. The reason I kept going was one, out of necessity, but two you have to look at financially what's working and what's not and when you consistently are seeing income from individual rooms or from a whole house where those numbers are quickly starting to exceed your mortgage and you start to see that passive income, I think it's a very logical explanation to keep going because those numbers make sense. 

0:10:07 - Andrew Winter

So if you're seeing this, it's analytical mindset, which I'm actually a pretty analytical person, but it comes to real estate, I'm much more emotional. 

0:10:14 - Brandon Hall

So I'm curious what drives the snowbird mentality Like? Why do that? 

0:10:21 - Camala Winter


0:10:22 - Andrew Winter

Definitely a little bit of compromise. So when we met, she lived in Florida and my stipulation was that I would want to spend summers at least in Cleveland. And so as we're driving up here, there's actually a story. I don't know if your mom even knows this one yet, but I was in the car when she told her mom the first time she was coming to Cleveland and her mom freaked out and it was the greatest like sound bite ever. It was like Cleveland, and so I was a little hurt because I think that Cleveland is this wonderful, like unknown, that people, just based on the national media, don't have an affinity to go there. But I mean, it's beautiful, the weather is consistent, the people are super friendly, and then when you think of Florida you think of beautiful beaches and anger. 

So you kind of marry those two together and if you do it at the right time of season, it's pretty enjoyable. 

0:11:09 - Camala Winter

Again, I'm going to go on the analytical side of that and, first of all, very timely. It's really good to diversify your portfolio, because there's these things that happen in Florida that are just unavoidable, such as hurricanes, and one comes through and wipes them all out. I'm really happy that we have other homes here in Ohio. Outside of that, I think the market in St P will never go away. It's a tourist destination. You're always going to be able to increase your rents, you're always going to have that income, and Ohio is not necessarily the tourist capital of the world. 

However, there's with the mass exodus out of New York and out of Chicago. People are really looking for a nicer area to live long term with their families, where they can live in the remote environment and get a little bit more bang for their buck. And in addition to that, the Cleveland Clinic, specifically, is really well known in this area, and so we do get a lot of people coming in for longer periods of time. That really serve that mid-market or sorry, that mid-length, mid-stay market where you're able to capture people who want to come in for their family, relatives or for surgeries or things like that. 

0:12:28 - Andrew Winter

Yeah, your father being an example of that. 

0:12:31 - Vikas Gupta

Yeah, I actually. I have three very good friends, all from California, all who went to grad school in Cleveland and if asked you know, if you couldn't live in California, where would you live? They actually are like, yeah, cleveland would be like a top two on my list. So it's there, like, if I guess for people who experience it, it definitely, it definitely has a draw. 

0:12:54 - Andrew Winter

It does. I mean it's really weird because I tell people in Florida I'm like I'm so excited to go back to Cleveland this summer and their first response is why, what do you possibly want to do up there? I'm like it's crazy, with the amenities that we have and the distance to drive places, like I mean people hear complain about traffic all the time but it takes you 30 minutes to go anywhere in the city at any time of day really. So I have no complaints. 

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0:13:55 - Vikas Gupta

H-R-E. So what does your fast forwarding to today? What does your portfolio look like? 

0:14:01 - Andrew Winter

So our portfolio today consists of I have purchased two homes here in Westlake, ohio. One was supposed to be our summer home but, due to, again, life situations that we've been conditioned for, we ended up moving back into my first home. And then we're under contract potentially to look at a second home that will be our forever summer home, so that we're not moving because it kills one of us every year to be type A and to have to organize and move and the other one of us just picks up a carry on and leaves. Yeah, so ultimately that's where the Cleveland portfolio has kind of been. Ultimately, these houses are homes that I've lived in. I have enjoyed my time in each one of them and it's exciting to get to share it. 

And then the Kingfish house I actually purchased specifically to do that model of I want people from the North to come down and be able to do vacationing and to feel comfortable doing it. Most of the people that go down to Florida they try to get an Airbnb and they're like, oh, the neighbors are on something, or, you know, I don't feel comfortable with the area that I ended up renting, or there's no buses here. How am I supposed to get around? And for us the intent was for 15 minutes from the beach you can have guests come in. You know we're all from the North, so we we know kind of the struggle of trying to get out. But it was really more kind of focused on the communal aspect. And actually now I currently have a group of Clevelanders renting the property from me too. 

0:15:23 - Camala Winter

So that's my portfolio and then I guess all in all we have a total of, I'm going to say, six and a half properties across Florida and Ohio. All of those properties initially started out as Airbnb's in short terms, whether it was rooms or for weekends, and then they slowly moved into that fully furnished model where they were that midterm solution and one of the things that really helped us propel our properties forward is being pet friendly. So we were able to find a really nice niche. So all of those properties kind of became that midterm solution and so recently we've converted five of the seven properties into long term annual contracts. So we've. But what's unique about those long term contracts is they're still fully furnished. So it serves a lot of that customer base where they're coming here for, you know, one to two years and they don't want to move across country, they don't want the firm, the property already there. 

So he has most of the properties. I only have two. So I'm like the small player in this dynamic duo. But I have two properties in Florida. That one is our primary residence and the other is a full time long term. 

0:16:48 - Brandon Hall

So I have a couple of follow up questions. One you mentioned that you, your properties, are more competitive when you Allow pets. Any nightmare stories from that, of course, oh. 

0:17:00 - Andrew Winter

I mean we have so many different nightmare stories, but I mean, what is nice, though, too, about our properties that kind of dissociates as well is that we Really kind of a focused on being a home right, and I know that that's difficult to do, but these were our homes, so we put that kind of effort in to do the small touches that really matter, whereas, like when I go to an Airbnb, usually the walls are white and there's like one or two photos that you can tell they grab from Walmart. It's even more funny when you go into some houses and you can see all the sheets are the exact same, because I feel like there's like a bulk Airbnb store somewhere that somebody buys the same sheets. So our homes are really unique in the fact that we do kind of put in those custom touches that you can tell we did put some energy into it. 

0:17:45 - Camala Winter

Yeah, as far as being pet friendly, some of the challenges that we've had is People don't think to change air filters, for example, so those can get really backed up with pet hair we have you know forgot about the husky. 

We've had a lot of fun situations where we've had a dog completely Scratch down all of the paint off of a door and like you just have to get a completely new door. And I've had I think I've had a lizard and people have asked me if they can bring their bunnies, and I've had a couple canaries and I'm like it wouldn't be my sort of pet. But you know, power to you and ultimately, how I think we were able to Combat that is, we have a really high price point Just to filter out some of those people who may not take care of your home. But another way that we structured our Payments was that we didn't necessarily charge a high pet fee and we really reduced that and that was really attractive to a lot of people have not seen that massive like $500 pet fee, but rather that that fee was really just bundled into the, the total fee, and the pet fee was like 50 bucks or something. So I think that really helped weed out some of the, the lesser quality tenants that you want to avoid. 

0:19:04 - Andrew Winter

Yeah, and I guess, touching on the dog friendliness piece, there is a weird weird like addendum to this with Florida specifically, and that they actually have. And it's weird I think there's actually something on the ballot for for Policy that they have discriminatory breed specific Restrictions so you can have you can't even have a German shepherd, but you can't have it. I think you get a lot of a chihuahua and I think that they're more aggressive but obviously the damage will be less. And I've had, like I've been around three different pit bulls that I Would have no problem hanging out with, but they're on the restricted list. So you have to be very careful about your selection process for dogs and you have to like kind of ask in pride for information Because if something does happen, you as the homeowner which unfortunately is a part of cams bad story are responsible ultimately for Damages that could ensue from it. 

So we've looked at like rider policies, even. But even rider policies on top of our homeowners insurance don't necessarily cover specific breeds. So how do you account for that? And there really isn't a good answer yet Other than, like I've had friends that have to go the route of doing a service animal because they're not a lot to have A specific dog and apartment complex, unless you get it certified as a service. 

That's very interesting. 

0:20:17 - Brandon Hall

And I have a short-term rental and I'm somewhat familiar with all the federal policies related to that type of stuff, where you know if they just show up with the dog, there's not a lot that you can do. 

0:20:28 - Andrew Winter

Yeah, it's, it's because I'm like I have to ask questions. I'm like, okay, just because insurance is asking like I'm not sure what it's going to be like. It's asking like I have to make sure that I'm in compliance with them because if something happens, then I'm ultimately liable, and I've had positive outcomes with working through Airbnb and their claims process. 

0:20:47 - Brandon Hall

So what made you transition to long-term rental? So I mean, it sounds like you guys really got your start with the midterm stuff, so why switch to long-term yeah? 

0:20:55 - Andrew Winter

when we started with short-term Well, mostly me and then I think we both for her she lived in her short term, so it was renting out specifically a bedroom. And then when we did short-term in Kingfish, it was also renting out bedrooms. We had three bedrooms in the front and then we lived in the back half. So for us to monitor the situation and make sure the engagement between tenants was up to Status that everyone was comfortable living in. That was pretty easy for us to do. And then the short term. I didn't Cleveland. I had a really good Maintenance process and I'd also just lived here, so I didn't necessarily need like maintenance person on standby because I knew that the house would survive for at least a year or two. 

But once that threshold broke and then you start to see things falling in disrepair, I mean heck. The some of the horror stories we've had With some of our tenants have caused a little bit of damage in the homes that it just continues to build. So when we looked at it it was just. And then you had the labor shortages and then prices increased crazy. So I moved more to midterm, just so that I didn't have the day-in, day-out maintenance and monitoring of the home and Then from midterm even we moved into longer term because it was nice to get that consistency in the paystubs, especially as our jobs continue to change and we had some difficult situations approach. 

We wanted to know that there was gonna be money flowing in in case there was a negative event that occurred, so we could be more Consistent. But also dealing with short-term. We found that people didn't care as much about the home they were living in because they were there for a specific event and it wasn't to take care of their, their domicile. When you moved to midterm they're like oh, I have to come back tomorrow, like I want to make sure that there's not like crap on the table or that I, you know, not cleaned the premises, because then that's something that they have to live in and pay for. So we found that just the quality of tenant we were getting in midterm was better and then now we've kind of migrated more into the long-term area. 

0:22:49 - Camala Winter

It's also important to note that our midterm strategy is kind of almost like our selection process for our long-term rentals. So it's almost like a way to vet somebody and see if they are somebody that we would like to work with on a long-term basis and ultimately day into your question of why we moved to long-term. It's it's a question of bandwidth. We're two people, we have seven houses. It's just not in our bandwidth, along with our full-time jobs, to be able to Service all of those short to midterm rentals Up to standards. So we had to sacrifice a little bit of the extra income to maintain that level of service and quality but still have the long-term value. And I think what's really helpful to note for the long-term revenue is that we were lucky enough to Purchase some of some of our homes before there was a spike in prices, and so the difference in what the net income we're making is still pretty substantial, even though we're Lowering our prices and we also focused this on the lens from the the tenant side. 

0:24:04 - Andrew Winter

So if you're looking to move across country, is it economical for you to look at taking your favorite sofa long, or is that something you sell on Craigslist? So when you're going to rent a house, you're like, okay, well, what's my cheapest option to possibly get started? And it's hey. 

Let's look at an Airbnb and let's just sell everything we have. 

And for us We've gotten me personally, I've gotten into a minimalistic view because she makes me. 

But now that I'm in this, it's like we pack up a single Jeep worth of Stuff and then we go down to Florida and then we're able to start living again and we're seeing that trend where people are just hey, I'm selling my sofa, I'm selling my table. Let me just take the person of the longies along with me and start over, and with that in mind, they're not paying these $8,000, you know moving fees or 10,000 fit, whatever it is. They're able to just come in use what exists and for the most part, you know, the upsell for us is hey, we want to be a long-term tenant, okay, here's a discount. You now take care of some of the maintenance activities that fall below a specific threshold and we've already vetted you. And that's even better than getting to the you know Application process where you get 200 unknown people and you have to filter out a list of those individuals where we've already worked with this individual and have a history so it sounds like you're managing your properties yourself. 

0:25:18 - Vikas Gupta

So I have a bunch of questions about how you're doing that, like how are you finding tenants? Where are you finding tenants? How are you managing the day-to-day? How are you managing the finances? Like, what are you? How do you make all that work, since you said you have full-time jobs and you now have seven properties to deal with? 

0:25:34 - Andrew Winter

Yeah, I mean it's funny. You know, we talked about just barely escaping these last two years of hurricanes in Florida, and it's been a challenge. I mean, last week we had both of our basements in Westlake flooded. I got three inches in one house, a foot of water in the other and we had a 75 year old tree fall. We also then had another tree fall during this latest storm in St Pete, and so what we did was we tried to start focusing around building good relationships with individuals that are going to help move us to that next stage, and that's honestly the initiative that's behind TrueReal is starting to vet people and understanding who you're ultimately working with. But in this particular instance, we've started working with handy people that we trust. That kind of give us, you know, at least a 48 hour turnaround in some of these pieces. And when it comes to the bigger task, we've kind of built a network of trusted vendors that we work with For the day to day. 

I've sourced all of our tenants, usually using Zillow, and then there's I mean I've been lucky. I'm not going to lie to you when I put up a Zillow post for the house in Coquina Quay, I got linked up with five people from Cleveland, ohio, and so instantly my heart was just filled. I was like cool, they're in right. We also got linked up with a great tenant that existed in our 57th Avenue house and you know we've been fortunate timing, especially timing and luck and so we've used Airbnb also, especially in Ohio, and VRBO had more success on VRBO personally to bring in tenants for the midterm and then, for most of the situations like I had, one person was building a house. It was supposed to take three months, it took two and a half years, so they ended up being a decently long tenant. And then we had another family that just moved here and they were looking for a longer term solution and we just signed them to a two year lease. So we've been fortunate to do the conversion and the upsell. 

0:27:24 - Camala Winter

I guess is what you would consider it with our current portfolio, I think another really strong channel for us finding tenants has been I don't think we've said anything that we're volleyball players and so there's a huge volleyball community, especially between Ohio and Florida, because there's a lot of Ohioans wanting to come down and train for beach volleyball and so there's he's a big fish up here in volleyball and so everybody knows his name when we come down, like he's the place that everybody would just that was our filter or filler. 

So definitely reference and those different community groups is a really good referral process for us and we've also had a lot of referrals through different agents, through different word of mouth. And I think what's really important about our strategy is when we talk about managing the day to day. We really have built those individual, locally sourced, individual like companies or people, as opposed to going to a chain and sometimes that isn't the most economical, but what it does is it builds a relationship and it builds credibility and so even through that referral network, we have people who refer us because they're our plumber or and they're like, oh I know somebody who has this house or sale, and we just get referrals all the time. So that's never really been an issue of filling a house because we have so many feelers out there. 

0:28:54 - Andrew Winter

Yeah, especially in Cleveland. I mean, I've been here for like 15 to 20 years and in that time I've developed a large network of people that I can reach out to and they're more than happy to help. And up here especially, we definitely try to keep it local. So I've been shop at our local convenience store for all the cleaning products that I need, ultimately because I know that I'm supporting local jobs and so that that is a huge piece that I try to do. And we also work with some local real estate agents who might say, like hey, you know, there's couples coming in from Arizona and they're looking at purchasing a house in the next three months. They need a place to stay. Is your house available? And so it's those type of connections that have helped us be successful, especially as it relates up here to the north, and we're working on developing that further in St Pete. I think we've got a great handyman now and some other key contractors that we work with. That have definitely kept us successful. 

0:29:42 - Vikas Gupta

So one thing that I read about what you shared with me is that you two have different investing styles. Can you tell us a little bit more about your each individual investing style, and then how how you make it work together? You first definitely because mine's embarrassing. 

0:29:59 - Andrew Winter

Well, mine's really not that complicated. 

0:30:02 - Camala Winter

I don't think it's a very logical and very data driven approach of simply looking at a house that's more or less move in ready. I like to invest in homes that are in a good area. They're competitive, they may need a little TLC, which makes it less than ideal. On like on the MLS, people kind of shy away from it because I don't know it needs new countertops or it needs new floors, but the plumbing is good, so it has good bones. But I'm not knocking out walls, I'm not completely redoing things. It's mostly move in ready. 

My general gut feeling on those is if I've unaggressively type A like, I'll just admit that, and if it's up to my standards where I could live in it, then most likely someone else will. And then from there I do in a competitive analysis of how much I would be paying and what that comps in the area could potentially make from a short term, mid term and long term standpoint. I also look at longevity. So is this a market that is a right now property or is it a in the future property? And I'm much more of a right now kind of approach and so that's where I make a lot of my decisions and I'm a person who is the qualities and the details. I can take a very simple home and make it really attractive with just tiny details, and I would much rather do that than buy something that needs a lot of work. 

0:31:38 - Andrew Winter

Yeah, and I guess I'll give her a cue to us where it's due, one she does. Her investment was different in that there's the cash out refinance option to then fund your next home, and that's something that I personally don't have the risk tolerance for. There's no risk, it's so much logic, and so I proposed it to her and I said listen, this isn't something that I personally would do, but this is an option that a lot of investors do use and if this is a tool you want to dive into, she can. 

And so the 57th Avenue house. She, like myself, faced a lot of criticism for purchasing that home but ran the numbers and saw that it was going to make enough to maintain a lifestyle for herself. So she took that with the FHA and then when she did a cash out refinance, she used the money from the cash out refinance to then purchase our now primary home. And when I looked at that house I was like this is not following in anything that I want, and also there were some repairs that needed done that I couldn't necessarily see past. And now, with the primary home that we have, I'm truly impressed with kind of where it's been. So I've been pleasantly surprised in both of her purchases. 

0:32:40 - Camala Winter

So I will share those numbers because I think it's so logical. So I refinanced my home in 2020, which made so much sense from an interest standpoint. I took an FHA that I had PMI on and it was that around 6%. I was able to refinance, get rid of PMI and get my interest rate to about a 3% and my mortgage increased by $1. Also, that's my payment, for I was able to take out $80,000. And I took $80,000 and reinvested it into this new home where I was able to put 20% down. I allocated 20,000 for repairs and so I was able to get a really nice home in a competitive market without PMI and put $20,000 into repairs right off the bat and make it amazing for a dollar. 

0:33:41 - Andrew Winter

Yeah, I will say our real estate agent did a wonderful job with the home we did purchase. I think we have 54 competing offers and ultimately our offer was strong enough to win our not primary home. So the same P market is different In the Cleveland area. What I've always done and this also goes into Kingfish, as I've purchased a primary home. So my primary home I bought in 2016,. Then I moved down to Kingfish officially by purchasing a primary home. I'd always been a Florida resident, but at this point I had, when I purchased the home, I was able to use an FHA loan at 3.5% down. Then I looked at getting a secondary home, which I was very fortunate. The mortgage organization that I used gave me a secondary home up in Cleveland, which again was the intent of this purchase, and I was able to get a portfolio loan. So they gave it to me at like I think it's 6.5% on a five-year arm, which is insane for an investment property. With that then I was able to get 15% down and that home was on a double lot and I've always done the model of a little bit different. I don't necessarily like to leverage. I usually will purchase with, hopefully, a low down payment and then I will live in it. I'll make the repairs to it. Usually it's a home that needs some TLC to it. I've also bought two homes of former hoarders, so there's been some clean out. That's been involved Definitely a lot of painting and a lot of details. Which I'm not very good at is a type, not a whatever the other one is. So I'm lucky that I've had again a very good handyman team. Also, cam's mom is pitched in. Our parents have helped us on some of these things. So we've had a really good support system to get these homes into a state that we're very proud of. I mean even the Kingfish home that was again occupied by a former hoarder. We were able to host our wedding rehearsal dinner there. So we had, like I think, 150 people show up in our house, which was incredible. I mean we got patio lights up. We even know there was a patio. When we bought this house. My mom started digging in our backyard and found a patio. So the amount of energy that have gone into these homes has been tremendous. But again, the support that we've had. 

And then back to my model I usually always invest with an equity. First approach my mom, I'll give, and give her more kudos where it's due is always about getting a deal. So when she goes into TJ Maxx or Marshalls or wherever she's like, oh it's on sale and she'll buy. And so I kind of do the same thing. When I'm looking at houses, I'm like nobody else wants it. I think I can make this work, I can spin it. There'll be some equity at the end. So if things do go down, I know that I still have the equity. I can ultimately back out of this opportunity and then I ultimately live for cash flow. 

0:36:23 - Camala Winter

And see, I think nobody wants it, so why would we buy that? 

0:36:27 - Andrew Winter

This is where we differ. 

0:36:29 - Vikas Gupta

So how do you navigate the differing perspectives? 

0:36:33 - Andrew Winter

It's funny because it really goes back to how we met and we both had very different views of not only the world but lifestyle and she's kind of more of getting into this home body approach where, like I'm even more of like I want to travel and I want to do things outside, and that really kind of carried over into real estate. She has a different strategy than mine and ultimately just comes down to respect, like if you show me something and it makes sense, you know I may not agree with it. There's a recent home purchase where I'm like this doesn't follow my motto at all and she goes well, it makes me happy and I'm like all right, that's enough for me, let's buy it. I think there's this mutual respect and understanding that we're both intelligent individuals and we live in a world these days it's very black or white, like it's either right or it's wrong, and we live in this world where I, hey, I made understand it, but you're an individual and I respect your decision and I think it's the right approach. 

0:37:22 - Brandon Hall

What you just said about it makes me happy, so we're going to buy. It is why I don't think there's any such thing as a mortgage rate lockdown. I know this is totally changing the topic of the conversation, but it's just a perfect example Of what I argue about anyway. The you know the whole premise of well, I got a 3% rate, I can't sell it because I'll give up my 3% rate is a fallacy, is it? When it comes to your primary residents, because it's like, hey, look, if your spouse is like we need to go being that better school district, then guess what? Your 3% rate doesn't matter anymore. All that matters is affordability. It doesn't matter about giving up my 3% rate. Anyway, sidebar, but just wanted to point that out because you just threw that example right out there that a lot of people don't don't see, they don't get the witness, that they don't understand that. 

0:38:09 - Andrew Winter

Yeah, well, I mean to add into that. I mean, that's where we've been fortunate. I, you know, I started my portfolio in 2016. We're at a 4.5% hers was what 6% you said and we were able to refinance in 2020 and even purchase. My FHA was a 3.5% or 3.25, which is still astronomically low. So for us, like, we again are locked into a great rate. 

But that doesn't mean it's not an opportunity to buy, because now that we're looking at a new primary home, you know it makes it very easy for us to look at. You know, again, low down payment. Now we get to the opportunity to look at do we want to rent the house that we declared our own? And now that we know all the ins and outs of the home, maintenance becomes much more easier, since we know where some of the pains might be. And so I've had a lot of conversations with people that have walked into getting into the rental properties and like, listen, like it looks fun, it looks great. I'm like you got to look at some of the horse stories that of course, we have, but this is your chance. You know, if you find a good home that's attractive and you think you know for the down payment jump into it. Worst case scenario you sell the house that you have a 3% rate on and you still make some money out of it. 

0:39:13 - Brandon Hall

So what does the future look like for you guys next couple of years? How do you, how do you plan a great portfolio? 

0:39:22 - Andrew Winter

We're currently discussing what it looks like. I mean, ultimately we've talked about kind of doing the vacation model where we try to buy a bunch of homes and cool destinations like part of beach or Phoenix where you see a lot of the snow bird population goes. But recently that's kind of changed with some of the complexities have come out of COVID. So for us, you know, we're pretty happy with the areas. We've kind of decided maybe we'll migrate to some new up and coming areas just to kind of stick stick within the preferences and risk talents as we've set out. But the question that we've actually faced the last few years is how do we scale this Right? And I think that's part of the challenge because we're husband and wife duo going up against like Wells Fargo that's buying 150 single family homes in. 

0:40:07 - Speaker 5


0:40:08 - Andrew Winter

How do you compete at their discounted rate of maintenance and upkeep on a home and still keep that like homey feel and people excited, where I'm not just paying the walls white and throwing up a cute photo? So that's kind of been the challenge of you know what's next, and that actually even breaks out into the true, real concept of how do you differentiate a good landlord from a bad landlord. And there is no Google review for something like that. You can't just look up your landlord and say, hey, are they good or are they bad? Because ultimately the reason the house is available is because the previous person is no longer there. And is that for a good reason or a bad reason? So the project of scale is a conversation we've continued to develop because even with the basement flooding, I mean my wife and I had to go to Home Depot, drop $500 at Home Depot and grab a stomp pump system and start vacuuming the basement. 

0:40:58 - Camala Winter

So never did I ever see myself standing outside of Home Depot at 545 in the morning Like it was the new Apple iPhone release to get a sub. 

0:41:09 - Andrew Winter

Yeah, like our excitement is way different than the average American at this point. We're like I need a stomp pump and you're like, oh my gosh, I found one. Like today I have to go over to Garfield Heights and we have to get a three inch donut that converts to a one and a half inch pipe for a stomp pump in line, because I was on a one and a quarter before. Like are you kidding me? Usually it was tracing, like where's the new Xbox one? 

0:41:31 - Camala Winter

at so, when it comes to like what's next, I think for me and I know that this is, you know, is a podcast designed to help people give you tips on real estate but I do think it's really important sometimes to speak to the fact that money is not everything, and so there's a really big weight given to happiness, and so you have to really think. 

For me, these houses we've put in a lot of work in our 20s and 30s to hopefully have that long term retirement fund. You know, when we're not able to bring in money, so it's creating that passive income. That is enough. We don't necessarily need to rule the world or we don't need to have a huge piece of the pie. We just need to be able to have a sliver that's going to sustain us and provide us the things that make us the happiest. And right now, I think what's making us the happiest is having time back to ourselves, being able to do the things that we've always wanted to do and having the confidence that we've selected the right team to be able to respond to emergencies, that we can feel happy that we are supporting local, to feel excited that we're able to give somebody quality over quantity. 

0:42:56 - Andrew Winter

Then ultimately to call it home. I mean, we don't just rent a house, we try to rent a home, we try to fill it with things that make it feel that way too. 

And I guess even to that point like the grand scheme of this, is that I want to have something to leave behind for my kids, and I'm kind of concerned about what the real estate future looks like, especially when you look at the data. You know, in the 1970s 1960s there were less women in the workforce, so your household income was mainly dictated by one of your partners. Now I think the percentage is like 60% of the household income is between both partners, and yet you still see people struggling with getting to home ownership, and so when I think about the future, I think, well gosh, if we bring kids into this world, what are they going to be able to purchase? Right, are they going to purchase a tiny 400 square foot micro unit in downtown Cleveland, ohio, with the hope of going into a bigger city? Or are we going to be able to have a portfolio of companies that we might be able to? 

give them a start that you know might not be attainable otherwise, and they can then learn about the ins and outs of home ownership how to change your electrical outlets, how to learn plumbing, and all of this I've had to do is. I think the best way to get into home ownership is to start when you're young, and that's something I wish I had done a little bit more paid attention to my father's lessons when I was holding the flashlight and not necessarily doing it appropriately. I wish I had focused a little bit more on some of the ins and outs of maintaining a home, and that's what I hope we can pass on to our future generations. 

0:44:20 - Vikas Gupta

Well, great, Brandon, I know I think you've said multiple times, right, Like invest with a goal, with the vision for what you want it to mean for your life, not just with like hey, I want to do more. So I think this is a great place to maybe segue into our closing questions. But actually, before we do that, I'm going to correct myself. Tell us about TrueReal. Give us a plug. What's going on there? 

0:44:43 - Andrew Winter

Yeah, the the true, real plug is that every parcel should tell a story. I mean, when you go in and you want to rent a house, you should be able to know when was the plumbing last updated, right as the landlord had a good history of Maintaining a quality of life for their tenants. And from there then you can start to make educated decisions about where you want to live and who you ultimately want to dictate what your home looks like. I mean, if you want a brand new sink and you message your landlord and they say you know, no, I'm sorry, we don't have any ROI on that like that stinks. 

Whereas if you have a landlord that really cares about your quality of life I mean I've had people before that I've messaged like, hey, how do you like your apartment? They're like I'm afraid to complain to my landlord because I'm afraid he's gonna raise rent and there needs to be some type of Rating system or metrics to really help make quality of life across the United States go up. And I think that this is the way to do it. But also you look at the increase in rents over the last you know Two years even and what are you getting Like? 

are you seeing an increase and you know the quality of homes for that premium price You're now paying, or are you still paying for the same apartment and just getting the increase in terms of the cost? And I don't necessarily think that that's fair. And so there's got to be some type of metric to either help reduce rent or to increase the quality of life. And that's the premise behind true real is to bring fairness, transparency and equality into real estate. 

0:46:05 - Vikas Gupta

Cool, and that's true, real dot IO, right. So if people want to check it out, they can go there. 

0:46:09 - Andrew Winter

Correct real IO and we're working on the early stage development of it as we speak. 

0:46:15 - Vikas Gupta

Awesome. Well, that sounds really cool. I've been fortunate in my life renting from Owners who lived in buildings, but I've heard plenty of horror stories from friends, so yeah, I've had a few and that's ultimately what caused it. 

0:46:27 - Andrew Winter

I mean like cockroach infestation for four years. If you can show that history and with the current metrics you look at online, that same apartment complex has A b plus rating and I'm like there's no way it should be a b plus with the quality. But you look at the rating system. The people paying the bill for the, for the rating system to exist, are the apartment complexes, and so they're not going to go out and willingly give a apartment complex a negative review. 

0:46:54 - Vikas Gupta

Great. We have three closing questions that we like to ask all of our guests. So if you're ready, we'll dive into it. We're ready. Question number one what is your favorite book? And it doesn't have to be real estate related. 

0:47:09 - Camala Winter

I have read this book five times, and I read it when I was a fifth grader. It's called the firebrand by marins of merbradley and it's it's basically the helen of troi story, told from a different perspective of a fake or not a fake, but a, a twin sister that doesn't actually exist in greek mythology. 

0:47:32 - Andrew Winter

And mine. I can't remember the name of it, but it's about jobs to be done, and so, while you may look at something at face value, what is ultimately the reason that somebody is choosing to purchase or utilize your services over somebody else's? And it may be less than what you think it is or it may be more. 

Right, and so when we look at even our portfolio, we've seen Things that we never thought people would use our homes for being utilized. I mean, I once had a film crew in my home and never in a million years would have expected that that would be a type of clientele that I would get. And the jobs be done book was A really cool learning experience. 

0:48:07 - Vikas Gupta

Awesome. Yeah, I'm a big fan of the jobs to be done framework. We use it a lot here at his Evo. Question number two what is more important to you in investing in real estate appreciation or cash flow? 

0:48:19 - Andrew Winter


0:48:20 - Camala Winter

That is hard. 

0:48:21 - Andrew Winter

For me it would probably be appreciation of value, because I'm buying homes specifically at a discount to ultimately increase the value to something that A couple would look at this and go, oh my gosh, this home is perfect and I want to buy it. And when we purchased it. Unfortunately it's not like that, which I know that one of us isn't necessarily thrilled with always living in project houses. 

0:48:41 - Camala Winter

But um, I think mine is cash flow because I'm right now and I also know that I have that option to sell long term. But for right now, where can this get me? And tomorrow's never promised. 

0:48:58 - Vikas Gupta

Well, I like the decisiveness. We get a lot of wafflers on this one. 

0:49:02 - Andrew Winter

Yeah, well, we can see we're different again. 

0:49:04 - Brandon Hall


0:49:06 - Andrew Winter

Get in yay. 

0:49:07 - Vikas Gupta

And then our last question are there any final pieces of advice that you would like to leave our audience with? 

0:49:12 - Andrew Winter

My ultimate advice would be just because it seems difficult, don't give up on it. And I'm saying that because right now you're seeing a lot of uncertainty in the housing market and you're, I feel like the perception is don't even investigate because it's not worth it, and there's this sentiment that home ownership isn't for the next generation. And there are programs that exist if you look for it and if you work with a real estate agent. 

I know specifically in Cleveland Ohio. If you make I think I can't don't quote me on this but if it's 70k or 68 thousand dollars a year, you can qualify for a homeowners discount program where you can get a low down payment to be able to purchase your first home. And if you don't know of these programs or if you don't ask somebody about these programs, then homeownership does seem unattainable. Also, fha gives you the opportunity for three and a half percent. It's definitely going to be a little bit more difficult because there's less homes that will accept it, but it makes homeownership attainable and I've seen a lot of people that don't even and get started it and then pay rent and then it doesn't appreciate it, into something that's an asset that you can then transfer or have and leverage in another home purchase. 

So definitely get started, definitely reach out. I mean, we have conversations with friends all the time that ask about Becoming a landlord or looking at buying their first home and I hope that this is the encouragement for them to start doing it. I know that this podcast is set up on that and I appreciate it. 

0:50:35 - Camala Winter

I guess mine would be. You know, if there's a will, there's always a way, and Don't let fear be the reason that you don't do it. When I was in a tough situation, the way that I thought about it to get over my fear Was what's the worst that can happen? And if you truly ask yourself what's the worst that can happen, you'll find that you have to take seven or eight worst-case scenarios Before you even get to that absolute worst-case scenario, and in order to get there, so many things have to go wrong, and so purchasing a home Is not likely the thing that's going to derail your life. So that would be. My best advice is to really consider what is that worst-case scenario and how many steps is it really Going to take for you to get there? 

0:51:31 - Vikas Gupta

Great. Well, thank you both so much. I think this has been an amazing episode. Really appreciate your candor, especially when talking about some of your personal differences about the way you approach things, because I know that those things can sometimes get tricky. So thank you very much, I really enjoyed it. 

0:51:47 - Andrew Winter

Yeah, thank you so much for having us. We appreciate it. There's a pleasure meeting you both. 

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