BiggerPockets Real Estate Podcast - Snowballing $20K into 10 Rentals by Doing What You (Probably) Won’t w/Gary Striewski
Episode Date: February 24, 2025Would you sell your car, live without plumbing and electricity, and shower at the gym daily to build a rental portfolio? Now, would you do it while having one of the most prestigious jobs on the plane...t? If you said yes to both, you might as well be Gary Striewski, rental property investor, DIY home renovator, and, yes, host of SportsCenter. Wait… the host of SportsCenter used a bucket as a bathroom while renovating? Yep, but he’s got a good reason for going through the struggle. Working at SportsCenter has always been Gary’s dream job, but when 2020 hit, he knew he needed an alternative income stream. Real estate seemed like the obvious answer, but without much savings and only a car to his name he didn’t have many options to invest. So what did he do? Sold his car, downgraded significantly, and picked up a condo for $20,000 down. Fast forward a few years—Gary has turned that first condo into a full real estate portfolio, including a private ski house that’s soon to be a short-term rental. He’s had evictions, DIY renovations where he lived without plumbing for months, and closings that didn’t go as planned, but with persistence and grit, he’s become an expert investor. Follow Gary’s tenacity, and you can, too! In This Episode We Cover: How Gary turned a $20,000 down payment into ten rental units and a real estate portfolio Gary’s “value-add” renovation that 99% of people would never do themselves A huge tenant mistake Gary made that will cost you if you repeat it Why you should constantly evaluate selling your rentals, even if they’re performing well Whether or not condos are worth it as starter real estate investments Sports stars who (unsurprisingly) love real estate investing And So Much More! Links from the Show Join BiggerPockets for FREE Let Us Know What You Thought of the Show! Ask Your Question on the BiggerPockets Forums BiggerPockets YouTube Apply to Be a Podcast Guest Try REsimpli, The Only All-In-One Real Estate Investor CRM Software That Helps You Manage Data, Marketing, Sales, and Operations Grab Dave’s Book, “Start with Strategy” Sign Up for the BiggerPocket Real Estate Newsletter Find an Investor-Friendly Agent in Your Area 10 Hidden Ways to Buy Properties with Huge “Upside” Connect with Gary Connect with Dave (00:00) Intro (02:19) 1 Condo to 9 Rentals! (04:06) Base Hit First Deal (08:56) A Big Tenant Mistake (12:48) $60K Profit in 1 Year! (19:17) Living Without a Toilet for a Deal? (25:24) First Short-Term Rental (30:04) ANYONE Can Do This! (32:33) They Invest in Real Estate, Too!? Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1087 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
Transcript
Discussion (0)
How much are you willing to sacrifice to build your real estate portfolio?
You might have seen today's guests at 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 poppy 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.
this is SportsCenter. Just kidding, I really always wanted to say that into a microphone.
This is actually the Bigger Pockets podcast where we teach you how to achieve financial freedom
through real estate investing. But today's guest is Gary Streiske, 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, but 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 Bigger Pockets podcast. Thanks for being here. Dave, I got to 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 in a very,
very long time. Awesome. I'm excited to have you here.
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.
I mean, obviously, you're referring to the people who recognize me as being the Polish sportscaster on any given network, depending on where regionally you're listening from, from Denver, spent that good handful of years in Boston, in,
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. 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? 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 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 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 good, pretty healthy portfolio five years later.
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, you know, 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 first deal. Was it a rental property? It was. Yeah,
it was a, just a small, too bad, one bath condo in Hartford, about 15 minutes away from where I'm at.
And 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 2020, 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.
That's great. Tell me a little bit about why you picked a condo. So I was looking at anything that was
turnkey. Again, I only had $20,000 saved 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
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 1%. It checked that. You know, there was no CAPX. 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. 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 a 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.
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.
Um,
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 the time.
I pulled into my driveway at midnight.
And she texted me.
It was like 1155.
Hi,
Gary.
Oh my God.
I'm so sorry.
I was moving on my stuff in today.
I lost my key.
The very first,
Reality check, immediate.
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.
It just shows even your first, like, even when 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.
I learned more in the life lessons of that first deal and continue to learn more than any
monthly check, honestly.
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.
Yeah.
Maybe it was a bit more of a challenge.
But first, we have to take a quick break.
We'll be right back.
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Welcome back to the Bigger Pockets podcast.
We're here with Gary Streiske talking about his blooming rental property portfolio.
We talked about the first one went pretty well,
but you hinted at this before, Gary, that the second one was sort of the opposite and more
of a challenge.
Tell us about it.
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 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. And I used that money to spend $1,500 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 stones 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 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'll be locating.
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?
Right.
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 do.
So anyway, I did use that chunk of cash to buy my first multifamily we'll get into in a second.
Okay.
But certainly 10 months came and went, hey, got a job yet.
Oh, no, just this and that.
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 ended up evicting him 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?
Right. Yeah. I imagine it's disappointing because it sounds like your first deal, you
we're 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 as a business.
You know, you can't take on other people's financial problems as your own.
Yeah.
And I'm one of those guys who wear my heart on my sleeve.
and I'll listen. You know, 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 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. That's great. Yeah. So I'm glad
that you figured that out and were able to get a better situation for yourself and we're able to
find a new tenant there. You said that you bought a multifamily. Was that one also in Bristol?
It was. Yeah. It was 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 day, but that would not have tested the true grit of somebody
who wanted to make it in this real estate journey. Yeah, you need some of these stories to,
like, hang out with real estate investors. You need some, like, bravitas to explain, like,
all the sacrifices that you went through, all the luxuries you gave up. Oh, that's the, yeah,
that's the easy one. Wait till we get to the story about my second multifamily.
A live-in renovation where I was using a five-gallon Home Depot bucket to, you can finish the rest.
So 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's really good.
It's 10 ways to find hidden value in properties.
Oh, yeah.
And this sort of checked all of the boxes.
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. In my standards,
I gave them the option when I eventually took the property over, said, hey, you're 50% of market
rent. And I took out the fair market rent figures at the time. And I said, sit on it for a week.
I would love to have you guys stay. Let me know what you think is a fair increase. I love that.
Yeah. So 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 hired than the figure I was going to propose. And then 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 him,
Dave, closed and said, hey, this is unacceptable. This is not an acceptable way to, uh,
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 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. Total win. Yeah, that's great. 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. Wow. Yeah. Net. After commissions, you're still walking with that or that was before commission?
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. Yeah. 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. Yeah, that's that's basically new construction. For sure. 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. Yeah, I'm curious about that because a lot
of the orthodoxy in real estate investing is just buy rentals, hold on to 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 it just a just
better opportunities elsewhere. Yeah, I bought that for 160. I think I got two high two 40s a year later.
Pretty compelling. Yeah, 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'm definitely a buy and
hold, I would not label myself as a flipper at all. I do look at myself 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 two 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. 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.
Yeah. 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. It 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 on
to 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 continuing.
continuously re-evaluating, 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. Did you know, your house gets bored when you
leave? I can't actually prove that, but it probably misses out on the action, the footsteps, the late
night fridge raids. Yeah, when you're gone, your place is basically on unpaid leave. It's
sitting there in the dark thinking, I could be contributing right now. Your side room wants a side hustle.
Even your Wi-Fi is like, we could be networking. You're on vacation, spending money like it's a
sport while your staircase at home is fully capable of sending your income upwards. Here's the twist.
You can go on a trip and actually earn money. Airbnb makes that possible with the co-host network.
If you're away for a while or have a secondary property, you can hire a vetted local
co-host with real hosting experience to handle it all. A co-host can handle guest communications.
It can manage reservations and keep things running smoothly so you don't have to check your phone
between beach days. That means less stress and more time enjoying your trip. You can relax,
knowing guests are taking care of and your place is in good hands. You travel, your house works.
Everyone wins. If you're ready to host but could use some help, find a co-host at Airbnb.com
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But it's also historically been sort of complex, time-consuming, and expensive.
But imagine if real estate investing was suddenly easy, all the benefits of owning real,
tangible assets without the complexity and expense.
That's the power of the Fundrise flagship fund.
Now you can invest in a $1.1 billion portfolio of real estate, starting with as little as $10.
The portfolio features 4,700 a single-family rental homes spread across the booming sunbelt.
They also have 3.3 million square feet of highly sought-after industrial facilities, thanks to the e-commerce wave.
The flagship fund is one of the largest of its kind.
It's well diversified, and it's managed by a team of professionals.
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All right, we're back talking about Gary's portfolio here.
And Gary, I need to ask you, you got a property on house hunters, right?
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.
Is this also in Bristol?
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 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. You're on TV. What do you do? You just shower at work?
Dave, I got to tell you, man, not to get TMI or anything, but I had, 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.
Okay.
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 into 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 comfort.
So it helped so.
Had a nice little private shower.
But yeah, for about two months, I was living out of my gym bag.
And what were you doing to the property?
Everything.
And this was the property that was on house hunters that I eventually settled on.
So new windows, new kitchen, new bathroom, demo to wall.
It was just short of, I guess, a complete, a complete tear down.
Wow.
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.
Did you bring the same bucket to the bucket?
Yeah. The famous bucket.
David, it's very clearly marked as to not be confused with like my vacuum attachment
bucket or any other kind of bucket.
Yeah, like a biohazard sticker like you see it.
That was a phone.
all over him.
Yeah.
Yeah.
That was a problem.
So wait, I didn't, I didn't know about house hunters.
So you were a buyer.
Like, you got shown three properties on house hunters and this is the one you picked.
Yeah, you know what's funny.
Every single person on the crew, including the director and the producer,
we're 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 the house, dude.
What do you mean?
Makes good TV, though.
I'm sure they love it.
It gave me a complex. I was like, whoa, whoa, whoa, should I not be buying this? Is it that big of a dump?
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.
Did they set it up, though, that you were an investor?
Or do they present it like you're just buying 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?
And they did sort of set that up with the background.
Like Gary Streisky, 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 pretty much the storyline that we kind of presented on the program.
That's awesome.
I'm always curious what it's like.
I am also a junkie of house hunters.
I just love it.
I love, you know, I don't know if you know, but I lived abroad for a while.
Oh, yeah.
love House Hunters International. That one really gets me going. So it's a lot of fun. It's awesome
that you were able to be on it. I remember you calling in on previous episodes talking about living
abroad and living in Europe. And I'm like, too, 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?
I just bought my first house in New Hampshire and I feel like it's in freaking Siberia.
But honestly, once you're far enough away that you can't drive there,
It kind of, it's all the same.
At least that's how I feel about it.
You know, once I was moved abroad and it 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?
Yeah, this is the tipsy moose.
And this is my-
Is that the name of the property?
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. I'm 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. It was strategic in not opening this thing up to outside rentals immediately because I do, Dave, 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, yeah, we're looking at second quarter of 25 having this thing up and ripping.
Oh, nice.
What's the draw?
Is it white mountain skiing?
Why do people go up there?
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.
Yeah.
So wintertime, you have the skiing, which is great.
And then summertime, you're five minutes from actual beachfront.
So it 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.
Yeah.
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 seven inches of snow here.
That's super fun.
I mean, honestly, what are the reasons pick to move to Washington from Amsterdam is 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 just 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 it 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.
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.
Are you worried about that at all?
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 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.
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.
Totally, man. Especially with that personal use, not every deal needs to be a home run. It's the same idea.
Correct. 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.
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 sports center host box. I'm definitely the real estate guy at ESPN. That's fun. 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 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 ski house.
And I'm like, yeah, anytime you want to use it, just let me know. 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 have like a ski in lakehouse
to be able to offer that to my friends and families and coworkers.
But, you know, here we are.
It's super rewarding.
I love it.
Yeah.
I just was able to do that, like one of my oldest friends have a family reunion at one of my
property.
It's awesome.
Just pay the rental place.
Yeah.
It's like.
You can't put a price tag on that.
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 really nice parts of like the second home short-term rental part of the industry for sure.
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 feel like people resonate with real estate?
Because for me, it seems like people just get it intuitively.
That it's like something people want to talk about.
They're interested in.
And so I'm just curious, like, how that sort of developed your professional life.
You mentioned a little bit, but I'm curious if you could tell us a little bit more.
All the time.
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 did. 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 Hertz 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 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 a human bridge to make that connection. Yeah. And I sort of see myself as the
same in those other facets that interest me, i.e. real estate. That's super cool. Just the friendships and
relationships that I've started and had, all through real estate has been awesome. Yeah. It really is
nice. 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 bigger pockets has always really been about. But you see it.
all over the place, just in local connections, local meetup groups. It's really, I think,
one of the most underrated parts of this business is that it can actually just be fun.
Definitely. 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? 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, hey, Arad. Hey, hey, hey, Aaron. 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, who found their way into real estate and we just sort
of have like a friendly relationship. I have one funny story. Former outfielder, Gary Matthews Jr.
Yeah. He played out West, to play 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.
That's awesome. Yeah. It's very cool. It really is amazing how many people are interested in it.
Yeah. Well, Gary, thank you so much for joining us today. This was a lot of fun. Enjoyed chatting with you
about real estate. Hopefully we'll have you back some time to hear more about how the portfolio is
developing over time. 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.
Absolutely. And thank you guys so much for listening to this episode of the Bigger Pockets
Podcast. We'll see again in a few days. 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,
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