How Richard Ostertag Built a 15-Property Short-Term Rental Portfolio in Miami

Richard Ostertag (00:00)
there’s a lot of people that they want to buy a property is their dream. I was like that as well at some point. I think it’s important for them to work with somebody that actually knows the market knows the game. So I am an open book because as I mentioned, you know, like from the moment that that that Mauricio guy basically like helped me. I basically made the commitment that I am also going to be an open book and whoever comes to me to

to ask, I’m happy to help everybody. So if anybody is considering to buy a property in Miami, reach out and I’ll be happy to talk with you and give you all the insights that I have.

Quentin Edmonds (02:07)
Hello, everyone. Welcome to the Real Estate Pros podcast. I am your host Q Edmonds, and I am here today. get another fantastic guest that we have coming on that you will be able to look through their lens, see how they do business, and again, gain some very good insight and maybe find some things that we can actually do differently. And so I am so excited today to introduce you all to Mr. Richard.

Ostertag Mr. Richard, how you doing today, Good, good. I’m doing good, man. Doing good. Hey, listen, man, I’m the type I like to dive right in. So I would love for you to tell the people what’s your main focus these days. If you can, give us a little bit of an origin story, kind of how you got into the real estate space. I got to got doing what you do. And then also let them know what part of the world you’re in, man. People love to know where people are geographically. So what you’re up to, your origin story and where you are.

Richard Ostertag (02:37)
Good. Thank you so much. are you?

Quentin Edmonds (03:01)
Mr. Richard, sir, you have the floor,

Richard Ostertag (03:03)
Yeah, thank you so much and thanks for having me. So I am currently in Miami. It’s a very nice and sunny day here. I specialize in short-term rentals. I currently have a portfolio of 15 properties that I manage. Roughly half of them is my own and then the other half is properties I manage for the other people.

Quentin Edmonds (03:04)
Yeah, yeah.

Richard Ostertag (03:22)
So how I got to this, I’m originally from ⁓ Slovakia, which is in central Europe. I spent most of my life in the, or most of my career in the corporate. I had different roles, usually within the finance department. I was, thanks to my job, I was able to live and work in all around the world. So I started in Europe, then I moved to Asia for a,

for four years, I lived in Malaysia and then I moved to the US. I landed in the Bay Area. And so, you know, my job was, I had a good job, but it was not exactly, I was not really excited like in the morning when I woke up. And so then during COVID, when it was the lockdown, I decided to go to Miami for a few days. I never been to Miami before, just to escape the lockdown. And…

And basically the three days resulted in four months that I extended several times my stay because I just loved it here. I think Miami is a place really kind of like checks the boxes for me, all the boxes. And so then I purchased my first property. ⁓ It was a one bedroom condo in Brickle.

And it was initially, I never actually planned to do Airbnb or anything like that. The idea was I want to buy a property for myself because in the Bay Area, the price of the real estate was, you know, like significantly higher and I really couldn’t like afford or wouldn’t make sense. So I bought the first property and it put it on the market and actually it was doing really well and it was doing like better than I initially expected. So then I was like, hmm.

maybe I can buy another one. then I bought another one. And then by that time, within less than 12 months, basically the first property I bought for like 350,000 was worth 500 over 500,000. So I basically refinanced, I pulled a hundred thousand cash and I put another.

I bought another property. at that point, basically, my addiction was kind of fully developed. So I was really kind of on the mission, like, okay, how can I buy as many properties as I can? Because I could see the income stream that was coming from those properties and it was pretty good. And then you start to compare what is the effort I have to put in my…

Quentin Edmonds (05:20)
Yeah. Yeah.

Richard Ostertag (05:37)
you know, like my regular job and what is how much money I’m getting versus what is the effort I have to put here and how much money I’m getting. it was very interesting on that side.

And so, ⁓ so yeah, so then after that I bought a bunch of other properties and then at some point I realized that I really enjoy, this whole real estate. I joined the whole process from like, from the beginning from, know, like looking for the property, like crunching the numbers.

you know, picking really like the best, the best option, then going through the purchase process, negotiating. I really love that. And then after once you buy the property, designing the property, putting all the furniture and all that, and then basically putting it on the market and operating it and really like making, you know, like, like making our guests happy and giving them some kind of ⁓ some kind of experience. And so I felt like, okay,

Quentin Edmonds (07:15)
Yeah.

Richard Ostertag (07:17)
I really enjoyed it. So why not for me to do it full time? So I quit my job in 2024. It was ending March. And I did my license, my registered license and I became a full-time realtor. And right now I work with other investors or people that want to buy an investment property and I advise them, I guide them through the process. In some cases, I also end up managing their property afterwards.

And yeah, that’s where I am. I’m super happy. I never once regretted the decision to quit my job. I’m not saying it’s easy. It’s a totally different, you know, when you are, when you have a commission based job, which really state agents, you know, are basically, it’s a totally different game than when you are, you know, sitting in the office and you get your paycheck, whether you work or not really, you know, so, so yeah, that’s, that’s where I am.

Quentin Edmonds (08:11)
Oh man, Richard sir, thank you man. Thank you for telling us where you are. Thank you for taking us through the journey. Man, greatly appreciated. And as you was talking, I was writing things down, man. I was actively listening. And I’m going to reiterate some things that you just said, kind of regurgitate some of the things you just said, because I’m going to make a statement. I’m going to ask a question. All right? And so from Slovakia, you was in corporate most of your life, specifically in finance.

And that afforded you to work, go around the world and be in different places, right? But you kept waking up and it was like, hey, I’m not that excited about the day to day. And so you extended to stay in Miami after COVID or while we was in COVID, purchased your first condo, quit your job in 2024. I’m going to take these things back to you, right? Because I have a saying where I say destiny has no wasted moments. Destiny has no wasted moments.

Richard Ostertag (09:01)
Hehehe

Quentin Edmonds (09:02)
meaning no matter what you go through in life, momentum is building. And we borrow from different parts of our journey to get to the place where we are now. And now you got 15 properties in three years, you own half of them yourself. So my question to you, Richard, is what has destiny, what has these moments taught you about yourself? Throughout the journey, what has it taught you? Has it taught you resilience, discipline? Has it given you a new look on innovation? Like what has these moments taught you about you?

Richard Ostertag (09:30)
Well, I think that’s a good question. A lot of things, think. One thing is like, really everything is possible. know, like if you ask, if you are here like four years ago, before I bought my first property, I, or when I was trying to decide whether it’s a good idea to buy the first one, I felt scared.

kind of like, you know, like unsure, scared. I was like, I don’t know if I can do this. I don’t know if I’m good in this, you know, like until then I was like, you know, behind a computer crunching the numbers. I don’t know if I can do this thing. And, you know, funny enough what I did, because I wanted to talk with somebody that actually was doing that. So I sent a message through Airbnb to just like random, I just pulled up like some properties which are in Miami to like random hosts. And I asked, I told them, hey, like,

I’m thinking to buy a property, but I would love to talk with somebody like would you be willing to, you know, to meet and to talk or to have a call and obviously nine out of 10 people will send you to hell or will never, it will even not reply because it’s like, no, like, like, no, just go away. But there was this one guy who was like, his name is Mauricio. It’s a young guy and he’s like, yeah, let’s, sure. Let’s meet. we meet, we met up with, with, with him and with his girlfriend and they were like very young, like

probably around 22, 23, 24. And really he gave me so much confidence because we were just discussing, how do you do this and how do you do that? And so he basically had an answer to everything and he made it sound like it’s not so difficult. And that really gave me a kick. And until now, I believe me meeting with him was really like a big part of why I decided to go with that. So, you know, so…

Right now, looking back and basically realizing that I’m managing 15 properties in Miami. I think I am managing them. When I say I, it’s me and my team. We are managing them pretty well. We have really good reviews. We are booked all the time. And we have all kinds of properties from the smallest to right now we are adding some little bit more on the luxury side.

Quentin Edmonds (11:21)
Yeah.

Richard Ostertag (12:08)
I think, so back to your question, everything is really possible as long as you give it your focus and there is some kind of motivation or drive behind that. Another thing I would say, in this business, you have a new guest every two, three, four days, right? And you realize that every person is a totally different character, which has different expectations, which has different…

everything is different. So you really have to kind of like adjust. And that’s, think that’s a really good training ground for me and for my team. Because, know, you will deal with, with unreasonable people, you will deal with, you know, like people which are maybe frustrated, maybe for a totally different reason, maybe there is something happening in their life, and then they come and they kind of like, you know, they, they put it towards you. But I think

I think that that’s good learning opportunity because everybody, are all different. We are all built differently and not just physically, but also from inside. So I think it’s a good opportunity to kind of like, you know, to see that and to have the opportunity to talk to other people than from outside of your circle that you typically talk to.

Quentin Edmonds (13:20)
Man, so well said. Thank you, man. Bridget, so well said. Thank you for the thoughtful reflection and self-aware answer, man. I really appreciate it. Let me ask you this. What’s the next real goal for you? What are you looking to solve a scale next with your business?

Richard Ostertag (13:23)
and thank

I think definitely right now for me, the goal is to stabilize the operation. It’s very different when you manage one or two properties versus when you manage in one building versus when you manage 15 properties in four or five different buildings. We just added some new properties into our portfolio. They’re all in a different brand new built building. And also like the…

the need for the resource is very different. at this point I have a, I’m basically in the process of building a team, right? I have a virtual assistant in Nigeria, which is great. She’s handling all the communication with the guests, because we probably at this point, we receive like over 100, 150 messages per day from just the guests.

Then I have my brother back in our home country in Slovakia that is also helping me with with certain things. And I also have two properties in Slovakia that he is fully managing, but he’s also helping me with the with some stuff here in the US. And then I just hired ⁓ a person kind of like to be on site here ⁓ as a as a property manager, you know, for like the on site things and.

I am also kind of like now figuring out like how to deal with the cleaning because right now we are, we have it through a third party company, but I feel like it might be the moment for us to bring it in house. So, so yeah, so basically like my goal really is to kind of like stabilize the operation, make sure that we have enough resources and we are not running, you know, running in circles for me to be involved less than I am right now. And

And also, you know, as we discussed before this, you know, with the seeing how the AI is progressing and like there is basically like a new breakthrough product that comes out at this point every week. I really want to, I really want to implement that as much as I can into the into my operations and into how, you know, ⁓ just to really make our lives easier, right. And to make it more streamlined, faster and better.

Quentin Edmonds (15:25)
Yeah.

Richard Ostertag (15:38)
So, and I’m super excited about that part.

Quentin Edmonds (15:41)
Yeah, I love it, man. I love it. I think the sky’s the limit for what you’re doing. I think you’re building at a very steady, sustainable pace. And I’m excited, man, for what you’re doing. Let me say this, Rich. I want to ask you a question, and I want to get your perspective when you hear this word. When you hear the word relationship, what comes to your mind?

Richard Ostertag (15:57)
well, a connection with another party, right? Whether it be, ⁓ you know, business related or personal or, or, or anything else. So yeah, basically. Yeah.

Quentin Edmonds (16:10)
Yeah. One thing I love when I hear, I synthesize when I hear you talk, you you talk about your brother, talk about the people that you’re hiring and you talk about stabilizing operations. To me, that’s the focal point of a good relationship is that you’re building a community, you’re building systems where people that’s attached to you can thrive and be successful and have an ecosystem that’s, that’s helpful for everybody. when I, when I, I asked you that question because when I hear what you’re doing,

how you’re building these systems, hiring the right people. It makes me think that relationships that you’re building are relationships that’s really going to help out and be key components to your success. So that’s why I asked you the question, man. So yeah, yeah.

Richard Ostertag (17:31)
Yeah, and to be honest, like, ⁓ I’m very happy that I can, I’m able to do that because for example, like the, my, virtual assistant in Nigeria, ⁓ you know, she’s, could have hired somebody here, but obviously it will be much more expensive. So, you know, from just the, the, the labor cost arbitrage point of view, you know, it makes sense for me, but, but for her, I think, you know, she’s great. I really, you know, it took some time to train, to train her, but, ⁓ but, ⁓ you know, like she,

is getting a solid salary for what is the minimum or what is happening basically in Nigeria. I am getting a very good work, a very good team member and we are all happy and I feel like she is grateful for the opportunity.

And that’s great, you know? So yeah, it’s definitely about the relationship. And it’s with everybody, right? It’s an ecosystem. Like you have your cleaners, need to make sure that you have, know, like it’s working well there. You have, sometimes you need the maintenance people to come and, you know, and fix something. And the thing is like here in Miami, almost like…

There’s a of people that don’t speak English. and usually like in this roles like the cleaners or the maintenance guys. So, but so at this point I’m basically like Google translating, you know, like every conversation. And I even bought for my, for the property manager that I hired, cause she is really good. ⁓ And I really wanted her, but she doesn’t like, she couldn’t really speak well at that point. So what we did, I bought like this, it’s like a, it’s like a

It’s like headphones. It’s like the AirPods, but it’s a different brand and it’s basically translating the translating real time. when I did the, cause like when I was thinking about like hiring her, was like, okay, I have to, I have to teach her a lot of things. And it’s like, you know, at this point we can’t really, we can’t really talk, you know, we can talk about like with the hands and whatnot, but like it’s like, I need to give her like a really like a download of a lot of things. And so with the headphones,

It works like you take one headphone, she takes one and basically I’m speaking in English and it translating in her headphone in Spanish. She’s speaking Spanish and it’s translated. And suddenly like we did like a two hours of the training and it really helps. And also it helps her like right now, if I look back just in the past, we started to work together like maybe like three, four weeks ago, she’s actually making really good progress in actually speaking English because it somehow helps you, right? So.

So yeah, the relationships are definitely very, important. And I really appreciate and value each and every person, whether it is a person that is a private lender that is lending me like half a million or whether it’s be my cleaner. think all of them are important for a business.

Quentin Edmonds (20:21)
Yeah, man, I love it, man. I love everything you said. I love everything that you’re doing. And listen, Richard, like if someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you,

Richard Ostertag (20:34)
So I have an account on Instagram, ⁓ which I basically just started. My plan is to really make an effort and post a little bit more this year. I want to do more of the educational content. That’s my focus. So on Instagram, am under so Richard underscore Ostrotag, so my name and underscore my surname.

Quentin Edmonds (20:48)
Yeah.

Richard Ostertag (20:58)
or also via,

number and also have an email.

And I also have an account on, on, on LinkedIn, also Richard Ostertag So, so those, one of those four will work.

Quentin Edmonds (21:08)
Absolutely. Well, listen, my friend, I appreciate you, man. Let me say three things to you. First, thank you for your time. Really, really appreciate your time. Secondly, thank you for your story. Thank you for your journey and sharing your journey. I believe your narrative, your story is going to impact people and possibly course correct somebody and lead them in a direction that they wasn’t looking to go into, but they heard you. And so it sparked the idea. So it’s going to course correct somebody.

Lastly, man, thank you for the way you think and your perspective and bringing that perspective to this platform. I really appreciate you coming on, sir.

Richard Ostertag (21:39)
Thank you so much. just just last thing my you know, I know there’s a lot of people that they want to buy a property is their dream. I was like that as well at some point. I think it’s important for them to work with somebody that actually knows the market knows the game. So I am an open book because as I mentioned, you know, like from the moment that that that Mauricio guy basically like helped me. I basically made the commitment that I am also going to be an open book and whoever comes to me to

to ask, I’m happy to help everybody. So if anybody is considering to buy a property in Miami, reach out and I’ll be happy to talk with you and give you all the insights that I have.

Quentin Edmonds (22:18)
Absolutely. Well, y’all heard him. Y’all heard him. You heard what he said. Look in the show notes, get connected with him. But definitely make sure you are subscribed here because we’re going to continue to bring up people just like Mr. Richard. So, sir, thank you again. And everyone else, have a fantastic day.