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BiggerPockets Real Estate Podcast
Snowballing $20K into 10 Rentals by Doing What You (Probably) Won’t w/Gary Striewski
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- [00:00]
Dave Meyer
How much are you willing to sacrifice to build your real estate portfolio?
- [00:04]
Gary Striesky
You might have seen today's guest at.
- [00:06]
Dave Meyer
His day job hosting SportsCenter on ESPN, but he still sold his car and lived for months without indoor plumbing just to make a deal work. Keep watching to find out how the man who calls himself the Kimchi Papi has built an incredible New England portfolio, including a four season mountain vacation home that's about to be paying for itself. Hey, everyone, I'm Dave Meyer and this is SportsCenter. Just kidding. I really always wanted to say that into a microphone. This is actually the BiggerPockets podcast where we teach you how to achieve financial freedom through real estate investing. But today's guest is Gary Striesky, who hosts SportsCenter on ESPN. When he's not busy building a real estate portfolio in Connecticut and New Hampshire, Gary is here and going to tell us how he went from owning just a single condo to 10 units in less than two years, why he suddenly got the urge to start doing home renovation projects in his mid-30s, and which star athletes are also secret real estate investors. Let's bring on Gary. Gary, welcome to the BiggerPockets podcast. Thanks for being here, Dave.
- [01:18]
Gary Striesky
I gotta tell you, man, I've done a lot of cool stuff in my career and I'm not just saying this because we are in present company. This is like the most excited I've been to hop on a show or a podcast like in a very, very long time.
- [01:30]
Dave Meyer
Awesome. I'm excited to have you here and I think a lot of our audience probably recognizes you. But for those who don't, can you just tell us a little bit about yourself and what you've been up to in addition to being a real estate investor, of course.
- [01:43]
Gary Striesky
I mean, obviously you're referring to the people who recognize me as being the Polish sportscaster on. On. On any given network, depending on where regionally you're listening from. From, From. From Denver. I spent a good handful of years in Boston embedded with the Boston Red Sox, and now I continue to live out my dream of hosting SportsCenter on ESPN. So I am joining you from West Hartford, Connecticut, which is about 20 minutes away from the worldwide leader here in Bristol, Connecticut.
- [02:20]
Dave Meyer
All right, so you have a very cool job full time working at SportsCenter. You do a lot of other stuff as well, but that's one of your main gigs. How are you a real estate investor? How are our spheres crossing right now?
- [02:30]
Gary Striesky
You know, you mentioned having the dream job. I think everybody sort of came to a halt in Covid. You know, summer of 2020, I was fortunate enough to still be going into the studio hosting my programs, which was predominantly SportsCenter Snapchat at the time, but everything was parsed down, there was skeleton crews working on every show. So I found myself having a lot more extra time than I previously had. And I was looking at a small chunk of savings that I had built my way up to. And I just knew I had to do something with it because the 13 cents of monthly interest just wasn't going to cut it. If ESPN unfortunately had to, you know, cut some of their on air people, fortunately that didn't have to happen yet. Still, it definitely piqued my interest in finding something else to do. And real estate was an immediate option because about two years prior I purchased my first house. When I got the job at espn, one thing led to another, got my real estate license, found a condo, deployed the 20,000 bucks I had saved up up to that point and the rest is history. I scaled up to nine doors in about two years and I have a pretty, pretty good, pretty healthy portfolio five years later.
- [03:42]
Dave Meyer
Awesome. Good for you. Super cool story and super relatable, I think. I imagine a lot of people look at working at ESPN dream job, but at the end of the day it's still a corporate job. I'm sure it's a good corporate job, but people, regardless of where you're working, want that sense of security that, you know, ownership and able to sort of control your own destiny. I think that that motivation seems to be true for almost everyone. So Gary, tell us a little bit about your, your first deal. Was it a rental property?
- [04:11]
Gary Striesky
It was, yeah, it was a. Just a small two bed, one bath condo in Hartford, about 15 minutes away from where I'm at. And it's, it's funny because I distinctly remember my real estate agent, Cynthia at the time telling me when I closed, she said, hey, remember this process because this is the easiest it will ever be for you. This is going to be the easiest seller that you dealt with. Because he was selling it, it was in the family, they were getting rid of it. It was turnkey, it was beautiful, it was immaculate. They negotiated the price, they worked with me on it, they pushed back the closing, they reduced the price when something came up a little bit later. So for my first real estate transaction, I was like, oh, if they're all like this, why didn't I get into this sooner? And I'm so glad that Cynthia put that perspective on me because my second property was the complete opposite as it relates to that first condo, you know, I bought it in Hartford, which by the way is like a top five busy market as of like the last two years. I bought this in June of 2020, I think it was $73,000. And I immediately got it in circulation in a program here locally that helps families get back on their feet. Not quite section 8. It's a little bit more hyper intensive, hyper focused program. And I had that tenant and I believe by the time I sold it in late 2022, she was still there. So that brought me a little bit of peace knowing, hey, we were able to stabilize this person's life and then go on to the next one, which was a second condo that I purchased in Bristol about four months later. I bought my first deal in June of 2020 and I closed my second deal by October of the same year.
- [05:50]
Dave Meyer
That's great. Tell me a little bit about why you picked a condo.
- [05:55]
Gary Striesky
So I was looking at anything that was turnkey. Again. I only had $20,000 saved up up to this point. So it wasn't anything, you know, that I was going to be able to bite off a big chunk. You know, I was single at the time, no kids, so I was able to sort of deploy all of the money that I had in a sense, and sort of take this risk. But I didn't want to be taking too big of a risk, a single family or a multifamily. Again, this was my first sort of dive into the real estate investing world. So I kind of just wanted to take a couple nibbles at it, make sure I liked it first of all, I could handle it, and then sort of expand to more single family, more multifamily, which I now have a couple of each in my portfolio. It checked all the boxes too. You know, the, the 1%, it checked that, you know, there was no Cap X, I was doing all the, the condo riders and all of that stuff had been taken care of. So this was very, very much low risk, low maintenance, so to speak, and just an easy first deal for me.
- [06:56]
Dave Meyer
I think that's such an important key for people to think about here because everyone wants to hit a home run or grand slam on their first deal. And for me, as long as you learn something and you are not taking on excessive risk, that's the main goal. Because, yeah, at a certain point in your career, you can take on more risk. And if you have a solid portfolio like you have now, nine deals, and one of them isn't performing up to, up to par, that's okay. But you need to live to see that second deal, the third deal. And so having that first deal, even if it's condo, that's going to be a modest deal, sounds like for Gary and for a lot of people, this just sort of is the first building block that you can use to get to your second deal, your third deal.
- [07:40]
Gary Striesky
I think, to your point, like buying that first condo, I think what was more value for me than anything I got monetarily, you know, obviously it was performing in the black. It checked all of the boxes. Was stuff that I learned, you know, that you don't learn until you're in it. My very first night, Dave, my very first night renting to this tenant, she called me and I was working nights at a time. I pulled into my driveway at midnight and she texted me. It was like, 11:55. Hi, Gary. Oh, my God, I'm so sorry. I was moving all my stuff in today. I lost my key.
- [08:12]
Dave Meyer
The very first reality check.
- [08:15]
Gary Striesky
Immediately, she texted me at midnight and I was like, all right, I've come too far. I got to go give her a key. Dude, it was nuts.
- [08:23]
Dave Meyer
It just shows. Even your first, like, even with the closing, goes as well as possible. No plan stands up to operating a rental portfolio. You can't plan for it. You just have to be flexible.
- [08:33]
Gary Striesky
I learned more in the life lessons of that first deal and continue to learn more than any monthly check, honestly.
- [08:40]
Dave Meyer
Yeah. All right. So glad to hear that that first property went well. I want to hear more about how the second one sort of reversed itself. Maybe was a bit more of a challenge. But first, we have to take a quick break.
- [08:50]
Gary Striesky
We'll be right back.
- [08:52]
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- [09:23]
Gary Striesky
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- [09:52]
Dave Meyer
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- [09:52]
Gary Striesky
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- [10:04]
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- [10:49]
Gary Striesky
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- [10:51]
Dave Meyer
To leave the house and you pause.
- [10:53]
Gary Striesky
To double check the locks?
- [10:54]
Dave Meyer
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- [10:58]
Gary Striesky
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- [11:15]
Dave Meyer
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- [11:17]
Gary Striesky
I've had peace of mind since day one.
- [11:19]
Dave Meyer
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- [11:24]
Gary Striesky
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- [11:27]
Dave Meyer
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- [11:29]
Gary Striesky
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- [11:41]
Dave Meyer
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- [11:43]
Gary Striesky
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- [12:00]
Dave Meyer
Welcome back to the Bigger Pockets podcast. We're here with Gary Striesky talking about his blooming rental property portfolio. We talked about. First one went pretty well. But you, you hinted at this before, Gary, that the second one was sort of the opposite and more of a challenge. Tell us about it.
- [12:16]
Gary Striesky
And it's funny, Dave, because I still have this one in Bristol. But after I closed on my first in June, I was hooked. I had the bug. I was like, how do I get another one? So I sold my car because I, I got rid of my savings. So I sold the Jeep that I had, my 2012 Wrangler. I sold it outright. I sold it for 19,000 bucks and I used that money to spend $1500 on a 2007 Toyota Prius in the middle of summer that didn't have ac because I was like, I am all in, dude. I'm a grinder. So I bought a condo in Bristol, legitimate stone's throw from the ESPN studios because I thought to myself, okay, cool, I'm going to like give back to this company that hired me. So I'm going to rent this out to somebody moving in and starting a job. I'll keep the rents low. It's a lower priced zip code. So I listed this thing in October of 2020. And Dave, this is. You hear the horror stories about listening to and falling for as I'm using my quotes, some of the sob stories that you get in the real estate field. So it was a, it was a young man who was relocating his family. He had a young son and his girlfriend was pregnant. He was like, hey, I'm just trying to give my family a better life. We're relocating from the Bronx to Bristol because we have family here. I don't have a job, but here we go, Dave. Here we go. First red flag. First red flag. I don't have a job. Okay, whatever you locate and you'll get one second red flag. I'll give you 10 months prepaid rent in cash. And listen, man, I'm four months removed from my first deal. So I'm like, wait, you're going to give me $11,000? When can you move in?
- [13:53]
Dave Meyer
So, right.
- [13:54]
Gary Striesky
So thinking to myself, you know, I'm a guy who's worked since I was 14. I'm like, certainly especially with two kids, you'll find a job between now and the 10 months before your next rental payments due. So anyway, I did use that chunk of cash to buy my first multifamily. We'll get into in a second.
- [14:11]
Dave Meyer
Okay.
- [14:11]
Gary Striesky
But certainly 10 months came and went. Hey, got a job yet? Oh, no, just this and that. This reason? That reason. So, Dave, I think I gave him October. It was 10 months, so we got to October the next year. I had the. I ended up evicting him of. In August of 2022. But it was just one of those, again, situations where I probably learned more in the experiences that I dealt with with this particular renter than any money that he initially would have prepaid me, you know?
- [14:43]
Dave Meyer
Right. Yeah. I imagine it's disappointing because it sounds like your first deal, you were able to provide housing to someone who needed to get back on their feet. That's, to me, I think, one of the more valuable rewarding parts of being a real estate investor. And you want to continue that and offer that to people, but it's a fine line, and it's hard to figure out how to be generous and give people a chance, but also to protect yourself.
- [15:07]
Gary Striesky
Exactly.
- [15:07]
Dave Meyer
As a business, you know, you can't take on other people's financial problems as your own.
- [15:12]
Gary Striesky
Yeah. And I'm. I'm one of those guys who wear my heart on my sleeve and I'll listen, you know, every. Everybody is innocent until proven guilty. And I will trust anybody. I always give everybody the benefit of the doubt, whether it's in this field or my professional field or just personally. But I am. I definitely get it from my dad. As soon as the trust is betrayed or you give me a reason, a solid reason to know that this is your character, then it's like, okay, cool, I got my lawyer, I got the sheriffs. What else do we got? What. What else do we need to do? So I eventually got him out, and I'm happy with my guests that I have in there now. She's been with me for four years now because she started at that multifamily I bought. Yeah.
- [15:52]
Dave Meyer
So I'm glad that you. You figured that out and were able to get. Get a better situation for yourself and we're able to find a new tenant there. You said that you bought a multi family. Was that one also in Bristol?
- [16:05]
Gary Striesky
It was, yeah, it was.
- [16:06]
Dave Meyer
Okay.
- [16:07]
Gary Striesky
June of 2021 is when I purchased this traditional two family and I legitimately used the funds that I got from that second condo. That chunk of cash. Could I have bought a car that had ac. Of course I could have done that, Dave. But that, but that would not have tested the true grit of somebody who wanted to make it in this real estate journey.
- [16:27]
Dave Meyer
Yeah, you need, you need some of these stories to like hang out with real estate investors. You need some like gravitas to explain like this, the, all the sacrifices that you went through, all the luxuries you gave up.
- [16:38]
Gary Striesky
Oh, that's, yeah, that's the easy one. Wait till, wait till we get to the story about my second multifamily flip. A live in renovation where I was using a five gallon Home Depot bucket to. Okay, you can finish the rest. So I, I did. Dude, I'm built different, man. So I purchased this two family in Bristol. I got a great deal on it. And one of your most recent episodes, it was, it's really good. It's 10 ways to find hidden value in properties.
- [17:05]
Dave Meyer
Oh yeah.
- [17:06]
Gary Striesky
And this sort of checked all of the boxes. The, the owner was relocating states. They had the U Haul packed up ready to go during the showing basically. And then the bottom unit had been there for a while in severely under market rent. So I saw a couple of different avenues to really bring this thing sort of up to market. Yeah, in, in, in my standards. I gave them the option when I eventually took the property over, said, hey, you're you know, 50% of market rent. And I took out the fair market rent figures at the time. And I said, you sit on it for a week, I would love to have you guys stay. Let me know what you think is a fair increase.
- [17:43]
Dave Meyer
I love that.
- [17:43]
Gary Striesky
Yeah, so I sort of, I sort of took my hands out of the equation just to, you know, give them the decency. They've been there for three, four years. I didn't want to come over here and just start ruling with an iron fist. So I'm glad that they actually gave me a figure that was actually higher than the figure I was going to propose. And then the, the day of closing on this particular unit again, they were out of state, South Carolina. They had moved. And during my walkthrough inspection we went to the basement, my real estate agent and I. And the basement was wall to wall junk. I mean, you name it, it was there. Pallets of dirty laundry and bags, paint thinner, liquid old bikes. I mean, you name it, Dave, and they left it in the basement. So I've a little bit more seasoned now. I'm like, okay, this is my fourth or fifth deal. I know how to handle these things. At closing. I'm not going to close. Yeah, they're out of state. They got to do something about this. So we reached out to them day of closing, said, hey, this is, this is unacceptable. You know, this is not an acceptable way to hand over the keys essentially. And they're like, well what do you want us to do? We're out of state. And I was like, I don't know. But you're going to pay to get this. Sure, get this cleaned up. So eventually I walked away with 3, 500 at closing. Oh, nice to pay to have somebody come out there and clean it. With the extra money I actually had enough to replace all of the appliances in both units. So a way to add value kind of off the bat.
- [19:05]
Dave Meyer
Total win. Yeah, that's great.
- [19:07]
Gary Striesky
Yeah. And then so I bought that in June of 2021 and I actually sold it a year later because that's when Dave, I started to see the real market start to explode. God, I sold it for like 80,000 more than what I purchased it for.
- [19:20]
Dave Meyer
Wow. Yeah. Net after commissions, you're still walking with that or that was before commission.
- [19:24]
Gary Striesky
I think I walk with mid-60s. But after a new roof, new appliances, I put a French drain in the entirety of the bottom. Because this house is built in like the late 1800s.
- [19:33]
Dave Meyer
Yeah.
- [19:33]
Gary Striesky
As you know, everything in New England is like if you found a house that was built in the 50s, you have a new build.
- [19:39]
Dave Meyer
Yeah, that's, that's basically new construction for sure.
- [19:42]
Gary Striesky
So again, certainly some good learning situations in that two family. But again, I wanted to exit at the top of the market and I think we did a good job at doing that.
- [19:52]
Dave Meyer
Yeah, I'm curious about that because a lot of the orthodoxy in real estate investing is just buy rentals, hold onto them forever, never sell them. So you mentioned selling your first condo. Now you sold only after a year. It's a pretty short hold period. Why was there just better opportunities elsewhere?
- [20:09]
Gary Striesky
Yeah, I bought that for 160. I think I got two high two forties a year later.
- [20:14]
Dave Meyer
Pretty compelling. Yeah.
- [20:15]
Gary Striesky
And this was after I brought it to market rent and I modernized it in a way where the next buyer, whether it was going to be owner occupied or you know, a rental investor like myself, they weren't going to have to worry about the capex on it with the major systems having been replaced. And that's still my mindset as an investor right now is I, I'm definitely a buy and hold. I would not label myself as a flipper at all. I do look at myself as, as a long term hold. Long term Portfolio building investor. So those are the only two instances I actually sold properties because I got in so low and I saw the market doing what it was doing in these particular markets, the Hartford condo and then the Bristol 2 family, that it would have been silly to kind of hold on to that and take X amount of years to actually see those gains.
- [21:02]
Dave Meyer
Listen, I'm a buy and hold investor also and I think it makes a lot of sense to hold on to these things, but especially early in your investing career. A good strategy is to try and just build up your equity as quickly as possible because then you just have more capital where you can place bets. Because I made this mistake early in my investing career. I bought a four unit was my first deal. I held onto that for four years before doing anything and had built up a ton of equity that I was super proud of. But I could have been buying more deals and if I had traded it out or refinanced, it probably could have scaled a lot quicker. And so I get the sentiment and I think people should think about holding onto properties when, especially if, you know, appreciation slows down, you're not building equity as quickly. But I appreciate, Gary, that you're sort of looking at each property that you buy individually and not sort of sticking to some dogma like, oh, I buy and I hold on to forever, but doing that work that every investor should be doing of continuously reevaluating. Is this the best use of my money or is there somewhere that I could take my money and put it to a higher and better use? I want to hear what you did with that money. But first we got to take a quick break, listeners.
- [22:17]
Gary Striesky
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- [22:54]
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- [23:37]
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- [23:45]
Gary Striesky
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- [23:45]
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- [24:20]
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- [25:10]
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- [26:05]
Dave Meyer
All right, we're back talking about Gary's portfolio here. And Gary, I, I need to ask you, you got a property on House Hunters, right?
- [26:13]
Gary Striesky
Yeah, I have. My gosh, my second multifamily, which ended up being a side by side duplex, which I still have in my portfolio. It's one of my better performing properties. Yeah, it's my baby. This is the one day where I felt like, okay, I've earned the badge of property investor of real estate investor.
- [26:33]
Dave Meyer
Is this also in Bristol?
- [26:34]
Gary Striesky
This one's in West Hartford. Okay, so this one was in West Hartford. It was a probate property. So unfortunately the owner had passed away. He didn't live there, he was renting it out, out of state. One side was updated about a decade ago. The other side hadn't been touched. They were both rented out. One obviously a little bit higher than the other given its condition. So when I took it over, one side stayed for a couple of months. Two brothers, cool dudes, follow each other on Instagram, talk about golf all the time. The other side was the side where I saw, again to your, to your point, the added value proposition, which was, let me modernize this. It's in West Hartford. It is in one of the most desirable zip codes here in Connecticut. This is my first official house hack too. So I completely demoed one side. And because it was me, just by myself and my dog, homie, who's my absolute road dog, she lived with me through all of this. Dave, I'm telling you, dude, I didn't have running water for two months. I didn't have electricity.
- [27:33]
Dave Meyer
You're on tv. What do you do? You shower at work?
- [27:36]
Gary Striesky
Dave, I got to tell you, man, I. Not to get TMI or anything, but I Had everything down to a T. All right. I had my. To go bag my gym bag with me at all times. And I would go to the gym at night. Yeah, okay, so do my thing. Shower at the gym, go home. I did have my utility sink in the basement that was working, so I would brush my teeth at home. But when I would wake up, you know, hey, nature calls. Got a little bucket, fill it up, dump it in the utility sink in the basement. And then I would get ready for my day at work. I would sometimes go to the gym at work. And, you know, fortunately, ESPN's campus is adorned with some, you know, some of the nice creature comforts.
- [28:14]
Dave Meyer
I would hope so.
- [28:15]
Gary Striesky
Had a nice little private shower. But yeah, for about two months I was living out of my gym bag.
- [28:20]
Dave Meyer
And what were you doing to the property?
- [28:22]
Gary Striesky
Everything. And this was the property that was on House Hunters that I eventually settled on. So new windows, new kitchen, new bathroom, demoed a wall. It was just short of, I guess, a complete, A complete tear down.
- [28:34]
Dave Meyer
Wow.
- [28:34]
Gary Striesky
Once I got that up and running, you know, I lived in that property until about June of 2023 when I bought this single family that I'm in right now. And I sort of did the same thing.
- [28:45]
Dave Meyer
Did you bring the same bucket to the, the buck?
- [28:48]
Gary Striesky
The bucket?
- [28:49]
Dave Meyer
Yeah, but it's the famous bucket, Dave.
- [28:52]
Gary Striesky
It's very clearly marked as to not be confused with like my vacuum attachment bucket or. Yeah, any. Any other kind of bucket.
- [29:01]
Dave Meyer
Yeah, like a biohazard sticker. Like you see it? That was a funnel all over.
- [29:05]
Gary Striesky
Yeah, yeah, that was a funnel.
- [29:06]
Dave Meyer
So wait, I didn't, I didn't know about House Hunter. So you were a buyer like you, you got shown three properties on House Hunters and this is the one you picked?
- [29:15]
Gary Striesky
Yeah. You know what's funny? Every single person on the crew, including the director and the producer were like, not a single person watching this episode is going to think you're going to pick this house, Dave. And I was like, it's not that bad of a house, dude. What do you mean?
- [29:31]
Dave Meyer
Makes good TV though. I'm sure they love it.
- [29:34]
Gary Striesky
It gave me a complex. I was like, whoa, whoa, whoa. Should I not be buying this? Is it that big of a dump, dude? They're like, once they see the house you're coming from, which was my first house, my baby that I bought in 2018 and what I did to that property, compared to this house and the disrepair it's in, there's no way anybody in their right mind is going to think you're picking this house. So I was like, okay, well, it's going to be one hell of a twist when I pick this house.
- [30:00]
Dave Meyer
Did they set it up, though, that you were an investor, or do they present it like you're just buying for your. For your primary residence because it was your primary? But did you get the chance to explain that you're trying to do something bigger here than just live in it?
- [30:14]
Gary Striesky
And they. And they did sort of set that up with the background. Like, Gary Striesky, he's young. He's ready to take the next step in his life. He wants to put himself in a position. So when his parents get older. And that really is a big reason why I do do this, is. You know, my parents mean everything to me. They gave me every opportunity that they never got. You know, growing up, my dad was in the army. He joined the army when he was 17, and then became a Colorado state trooper. And then my mom moved here from Korea after meeting my dad when he was in the army. So she gave up everything to come raise a family. So I guess you could say it's sort of pressure to, like, not mess it up. You know, I don't want to screw it up for all the sacrifices they made for me. So a big part of that story was, you know, hey, he's trying to put himself in a position financially where one day he'll be able to take care of his parents in the same way they took care of him. And all of that is 100% true. So that's. That's pretty much the storyline that we. That we kind of presented on the program.
- [31:17]
Dave Meyer
That's awesome. I'm always curious what it's like. I. I am also a junkie of House Hunter.
- [31:21]
Gary Striesky
Yes.
- [31:21]
Dave Meyer
I just love it. I love. You know, I don't know if, you know, but I lived abroad for a while, so I love House Hunters International. That one really gets me going. So it's. It's a lot of fun. It's awesome that you were able to be on it.
- [31:33]
Gary Striesky
I remember you calling in on previous episodes talking about living abroad and living in Europe, and I'm like, dude, when's this guy getting back to the States? How is he managing a portfolio from not just across an ocean, but like, multiple different time zones? Yeah, I just bought my first house in New Hampshire, and I feel like it's in frickin Siberia.
- [31:52]
Dave Meyer
But honestly, once you're far enough away that you can't drive there, it kind of. It's all the same.
- [31:57]
Gary Striesky
Okay.
- [31:58]
Dave Meyer
At least that's how I feel about it. You know, once I was moved abroad and I was like, okay, I'm nine time zones away, so I have to be completely reliant on other people. That's true if you're three hours away or nine hours away, at least that's how I see it. I actually wanted to ask you about that though, because I've seen on social media you've been posting this place in New Hampshire. Is this a. It's like a short term rental though, right?
- [32:19]
Gary Striesky
Yeah, this is. This is the Tipsy Moose. And this is my.
- [32:23]
Dave Meyer
Is that the name of the property?
- [32:24]
Gary Striesky
That's the name of the property. It's my new endeavor. I fell in love with this particular area, which is about three hours north of me. So it is actually my second home up there, more than I am here in Connecticut. But because I do split my time, I'm going to make this my first foray into short term rentals. And I'm actually super excited about it. You know, it was, it was strategic in not opening this thing up to outside rentals immediately because I do, Dave, like, want to familiarize myself with the area. I don't want to be the guy who buys a house and then the next week pisses off all the neighbors because they're seeing all of these out of state license plates. So I do kind of operate, I think, with a little bit of hopefully, empathy and some decorum for my neighbors. And I've ran the figures, I've met with the property management companies. I actually just agreed to team up with one last week, so.
- [33:17]
Dave Meyer
Nice.
- [33:17]
Gary Striesky
Yeah, we're looking at second quarter of 25. Having this thing up and ripping.
- [33:22]
Dave Meyer
Oh, nice. What's the draw? Is it White Mountain skiing? Why do people go up there?
- [33:27]
Gary Striesky
Yeah, all of it. If you're familiar with the lakes region, this is actually on Gunstock Mountain. So I'm about 60 seconds from the entrance of the ski mountain.
- [33:35]
Dave Meyer
Yeah.
- [33:35]
Gary Striesky
So winter time you have the skiing, which is great. And then summertime, you're five minutes from actual beachfront. So quite literally is a Four Seasons rental. But for me, being from Colorado, growing up skiing, I wanted to get back to having the ability to ski.
- [33:51]
Dave Meyer
Yeah.
- [33:52]
Gary Striesky
So actually going up there after the pod today and hanging out with the girlfriend for a couple of days, we're supposed to get like 7 inches of snow here.
- [34:00]
Dave Meyer
That's super fun. I mean, honestly, one of the reasons picked to move to Washington from Amsterdam was to be able to ski again. I miss it. Once you live in Denver, Colorado, it's pretty hard to give it up. It's such a nice part of life and at least for me, like, I love being outside and having something to do outside in the winter is just such a big draw, so. Totally understand that. I'll tell you though, man, I bought a ski house in Colorado that I use part time, but it's mostly a short term rental. It definitely changes it a little bit when you're renting it out to people. I'm just. Yeah. How do you feel about it? You know, because you buy it as a second home, you want it to feel like your own home, but then people are also in it. It. Are you worried about that at all?
- [34:41]
Gary Striesky
You know, if this thing is rented out a third of the month just to help offset or offset completely the mortgage, that's a win for me because as you mentioned, it was one of my favorite episodes. That's why I keep referring to it. I mean, it's just a forced savings account for me.
- [34:54]
Dave Meyer
Yep.
- [34:54]
Gary Striesky
At this point. And that's probably a top three viewpoint. I see my entire portfolio, which each one of these properties is just forced savings.
- [35:02]
Dave Meyer
Yep.
- [35:02]
Gary Striesky
So I don't have to be, you know, net positive anything. As long as I'm chipping away at the principle, I'm okay with it.
- [35:08]
Dave Meyer
Totally, man. Especially with that personal use. Not every deal needs to be a home run. It's the same idea.
- [35:13]
Gary Striesky
Correct.
- [35:14]
Dave Meyer
The whole point of real estate investing is to better your quality of life. Right. So if your quality of life for you is being able to enjoy this property, that's what you should be doing.
- [35:25]
Gary Striesky
And I will say this, it is cool because I kind of have become three things at ESPN. I think outside of me just checking a SportsCenter host box, I'm definitely the real estate guy at ESPN.
- [35:36]
Dave Meyer
That's fun.
- [35:37]
Gary Striesky
I'm kind of the watch guy at ESPN as well as well as like the motorsport car enthusiast at espn. You're like, okay, typical dude, like, okay, oh, wow. You like sports cars and watches and real estate. But it does serve a professional purpose in when people want to have a conversation with me outside of sports. And I've. I've found myself connecting with, you know, athletes or coaches or people in our industry more and on a more fair playing field, talking about other stuff, I. E. Real estate, you know, than sometimes sports and it's, it's like the ultimate flex when they're like, oh, you have a, you have a ski house. And I'm like, yeah, anytime you want to use it, just let me know. Yeah, just pay the cleaning fee. And it's, I don't know, it's like so cool. I guess middle school Gary would have never thought that I'd have like a, a ski and lake house to be able to offer that to my friends and families and coworkers. But know, here we are.
- [36:27]
Dave Meyer
It's super rewarding. I love it. Yeah, I just was able to do like one of my oldest friends, have a family reunion at one of my properties, just pay the rental place.
- [36:35]
Gary Striesky
Yeah, it's like, you can't put a price tag on that.
- [36:38]
Dave Meyer
I was like, really proud of it. I lost money on it and I was like, this is awesome. I get to help out my friend, you know, like. But that's super cool. I think that's one of the, one of the really nice parts of like the second home, short term rental part of the industry for sure.
- [36:52]
Gary Striesky
Yeah.
- [36:52]
Dave Meyer
All right. Well, I'm actually, I was curious about that you mentioned this. Just like, you do a lot of stuff, you're interested in watches and motorsports and sports and stuff. Like when you, you know, you have a big social media personality, do you, do you feel like people resonate with real estate? Because for me, it's just, it seems like people just get it intuitively that it's like something people want to talk about, they're interested in. So I'm just curious, like how that sort of developed your professional life, you mentioned. A little bit, but curious if you could tell us a little bit more all the time.
- [37:23]
Gary Striesky
Again, I mentioned I turned 38 in January. And it's weird. I don't know if it was like this for you, Dave, but when I turned 30, something like a switch just flipped and I was like, I want to build a fire pit. I want to put up a fence. I want to learn how to wire up, you know, small, low voltage, electrical. And I, and I did. You know, my first home was like my first project. And I have this before and after of my backyard being in complete. It was a jungle. And I think posting pictures and videos of that, to your point, really does resonate with just the average person. Like you and I, everybody listening. We're never going to know what it's like to be Jalen Hurts and win Super Bowl MVP or be LeBron James and dunk a basketball. But we all know who operate in this space. That first feeling of a closed deal or that first time, you know, an investment really paid off or a risk you were willing to take in any sort of facet, you know, ended up paying dividends if it's literal or figurative. And I think that's just sort of, you know, the common ground. I, I, I see myself as a bridge in my professional job of what happens in sports and describing that and telling that and connecting that to the people who enjoy the sports. And I'm just sort of the human bridge to make that connection.
- [38:44]
Dave Meyer
Yeah.
- [38:44]
Gary Striesky
And I sort of see as the same in those other facets that interest me, I. E. Real estate.
- [38:51]
Dave Meyer
That's super cool.
- [38:51]
Gary Striesky
Just the friendships and relationships that I've started and had all through real estate has been awesome.
- [38:56]
Dave Meyer
Yeah, it really is nice. It, it's, I never expected that when I got into real estate that it would be like a source of social connection and personal fulfillment beyond just making money, but it really is. And I mean, that's what BiggerPockets has always really been about. But you see it all over the place, just in, in local connections, local meetups, groups. It's, it's really, I think one of the most underrated parts of this business is that it can actually just be fun.
- [39:20]
Gary Striesky
Definitely.
- [39:21]
Dave Meyer
All right, well, on this topic of personal connections, are there any interesting sports personalities or other anchors or people at ESPN you've met who are like, low key into real estate?
- [39:31]
Gary Striesky
All of them, you know, really, I mean, when Alex Rodriguez was at ESPN and he was buying, you know, these massive syndications and funding all of these massive apartment and condo developments, I just wanted to get, you know, his ear for five seconds to be like, hey, hey, a rod, A rod. If you, if you need, like, if you need some capital, like, I got, I got some money. But it is cool because I've actually connected with a lot of athletes that I grew up watching, quite frankly.
- [40:01]
Dave Meyer
That's so cool.
- [40:02]
Gary Striesky
Who found their way into real estate and we just sort of have like a friendly relationship. I have one funny story. The former outfielder, Gary Matthews Jr. Oh, yeah, he played out west, played for the Angels. We have the same name and I believe he saw me on House Hunters. And we connected via Instagram. And it's just one of those, like, goofy connections that this guy's a former professional athlete. I cover sports, but our connection was my real estate investment.
- [40:30]
That's awesome.
- [40:31]
Dave Meyer
Yeah, it's very cool. It really is amazing how many people are interested in it.
- [40:35]
Gary Striesky
Yeah.
- [40:35]
Dave Meyer
Well, Gary, thank you so much for joining us today. This is a lot of fun. Enjoyed chatting with you about real estate. Hopefully we'll have you back sometime to hear more about how the portfolio is developing over time.
- [40:46]
Gary Striesky
Dave, much appreciated. This was bucket list stuff for me. I had a really good time, man. Thank you so much for allowing me to come onto your show and chop it up a little bit.
- [40:55]
Dave Meyer
Absolutely. And thank you guys so much for listening to this episode of the Bigger Pockets Podcast. We'll see you again in a few days.
- [41:03]
Gary Striesky
Thank you all for listening to the Bigger Pockets Real Estate Podcast. Make sure you get all our new episodes by subscribing on YouTube, Apple, Spotify, or any other podcast platform. Platform. Our new episodes come out Monday, Wednesday and Friday. I'm the host and executive producer of the show, Dave Meyer. The show is produced by Ian K, copywriting is by Calico, content and editing is by Exodus Media. If you'd like to learn more about real estate investing or to sign up for our free newsletter, please visit www.biggerpockets.com. the content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. And remember, past performance is not indicative of future. BiggerPockets LLC disclaims all liability for direct, indirect, consequential or other damages arising from a reliance on information presented in this podcast.