From Tech to Airbnb: A Real Estate Investing Success Story

Dylan Silver (01:31)
Hey folks, welcome back to the show. Today’s guest is a realtor based near Yosemite National Park who specializes in serving vacation rental investors with a background in high tech before moving into real estate in 2021. He now owns three Airbnb’s, two locally and one in San Antonio, Texas, and shares his expertise on the YouTube channel, Yosemite Area STR Investors. Please welcome Lenny Sharp. Lenny, welcome to the show.

Lenny Sharp (01:31)
Thanks Dylan.

Dylan Silver (02:02)
It’s a pleasure to have you on here, Lenny. I always like to start off at the top by asking folks, know, how did you get into the real estate space?

Lenny Sharp (02:04)
Well, maybe like a lot of people, my wife suggested I get my real estate license and I’m not quite sure what her motivation was, but she thought that I would be good at it. And, you know, I think I’ve done pretty well, but I’ve done much better now that I’ve kind of found my niche because.

As I tell you know, agents, new agents all the time, it’s like you really have to think about, you know, what is it that you can do better than anybody else in your market, right? There’s tons of agents, lots of experience, but you have to set yourself apart. And I mean, basically that’s what’s happened. The combination of experiences in my life, being an Airbnb host, you know, getting into real estate, immediately helping.

friends and you know that wanted to invest up here like this just quickly became my thing and so Here I am Yeah, I was an investor first so we we moved up here near Yosemite in 2016 after four years living in Japan and we

Dylan Silver (03:00)
What came first, the chicken or the egg, right? Were you an Airbnb investor first or were you the realtor first?

Lenny Sharp (03:16)
We literally found a house and paid $100,000 more than we planned on spending because it already had an Airbnb in the ground floor apartment. There were many months during that first year that the Airbnb income basically paid our mortgage. So, you know, for us, it was like, yeah, this works. And anytime we want to have family in, we just block it and everybody can show up. It’s only my wife and I in a 32-hundred-square-foot home.

So we’ve got plenty of space. We even experimented for a while with a second space in our home. But now my wife is taking that over as her full-time art studio. So lost that income, but happy wife, happy life. But yeah, so we got into it that way. We had a good experience. Then we bought a second home while it still had a W-2 job and could qualify for a mortgage. Bought a second home in Mariposa, which is also in our market.

Dylan Silver (03:55)
Right?

Lenny Sharp (04:09)
That’s done quite well. Then I ended up buying another home in San Antonio, Texas. like somewhere along that line, as we were going through our investing journey, I got my license and began helping other investors.

Dylan Silver (05:10)
You know, it’s funny because my mother is half Japanese. Both my parents speak Japanese. My dad, I feel like, spent half of my childhood in Japan. And I

just came up to Dallas from San Antonio. I lived in San Antonio for five years before moving up to Dallas. So look at this connection, right?

Lenny Sharp (05:22)
meant to be. I’m so glad we met through this. And by the way, have you been to Japan? I have not. you gotta go. I mean, it’s so good. I unless you don’t like…

Dylan Silver (05:34)
I have not, can you believe that?

Lenny Sharp (05:42)
Clean streets, know, safe to walk at night, beautiful views, wonderful food. If you don’t like any of that stuff, then don’t go. I mean, it’s awesome. You really need to go. So you must speak some decent Japanese. mean, you have to, right? 少しわかたます? That means just a little bit. And no, I don’t. was a very poor student. They supplied me with a language teacher. But because the office I worked in, everybody spoke English. I was a little bit lazy, but my wife…

Dylan Silver (05:53)
So you must speak some decent Japanese, I mean you have to, right?

English.

Lenny Sharp (06:10)
She worked harder at it and speaks better Japanese than I do. the urban areas, definitely you’re going to find enough people that speak English. Sometimes you get out in the rural areas and you might have difficulty, but generally speaking, you know, they all have to take English in school. So you can definitely get around.

Dylan Silver (06:14)
Does the population there speak English or is it really hit and miss?

I’m curious about this is maybe off the beaten path conversation here, but what

is real estate like in Japan? Does it have kind of the same market pressures that we have here? Do properties appreciate over there?

Lenny Sharp (06:38)
It’s a little weird. mean, I don’t know that much about it, honestly, but the one thing that is odd is that they will, you’ll see perfectly good buildings being demolished and they build a new one. like, real estate effectively depreciates in Japan, like any, like

other assets and then they, guess to keep their construction industry going, they tear down the building and build a new one. So like I said, when we were there, we saw lots of, you know, commercial buildings, residences, you know, like unless they were historically important, like they have no problem tearing down a perfectly good building and building another

Dylan Silver (07:25)
I also have another granular Japan question. If I wanted to eat like sashimi don, right, which here would cost like $28, $32. Is it the same over there in US dollars or is it maybe a little bit more cost effective?

Lenny Sharp (07:28)
Well, last time we went was a little over a year ago and the exchange rate was really good. So that helped. But I would say, yeah, I mean, it’s again, get out of the tourist areas.

You can find, I mean it’s very reasonable. you go to the right places, it’s very reasonable. Everything. Food, lodging, everything. And they have Airbnb’s in Japan. They work out pretty well.

Dylan Silver (07:55)
Okay.

It’s big over there, right? One of the things that I, this is a funny conversation. So I’m going to be doing some geo arbitrage

of my life here in a, in a bid. I don’t know if this podcast will air by the time that I would have left, but I’m actually moving to Santa Domingo, which is capital of DR Dominican Republic. And, uh, one of the big reasons is just the geo arbitrage element of it. So us dollar goes so much further out there. And then you can get like the place I’m going to be staying in is

Lenny Sharp (08:09)
⁓

Dylan Silver (08:27)
a two bedroom, two bathroom condo, mile and a half from the ocean with a balcony, right? And for the full year, it’s like $3,400 for the full year.

Lenny Sharp (08:36)
That’s crazy

Dylan Silver (08:38)
Crazy, crazy, crazy. You absolutely can’t. Honestly, Lenny, so one of the things that they have over there, which we don’t have over here, I’ve actually asked some guests of the show who are involved in commercial residential new construction builds. So over in the Dominican Republic, they’ll have new build high-rise apartments or condos, or they even just call them penthouses, where you can…

Lenny Sharp (08:38)
It’s two-bedroom so I can come join you let me know

Dylan Silver (09:04)
put a down payment on it and then finance

it over time. And maybe it’s not built yet, but maybe it takes two years to build. And that’s how they’re financing the build, but then also how they’re finding tenants. So I don’t even know how much credit even comes into play there. It may be, and I don’t know, I need to do more due diligence on it. But I spoke with a realtor who told me, yeah, if you’ve got 15 to 20 % down and then you make monthly payments, you can end up buying, you know, $100,000 US dollar.

Lenny Sharp (09:06)
it over time and maybe it’s not built yet but maybe it takes two years to build and that’s how they’re financing the bill but then also how they’re finding tenants so I don’t even know how much credit even comes into play there it may be and I don’t know I need to do more due diligence on it but I spoke with a realtor who told me yeah if you’ve got 15 to 20 percent down and then you make monthly payments you can end up buying you know a hundred thousand dollar US dollar

Dylan Silver (09:33)
condo, you know,

Lenny Sharp (09:33)
condo you know

Dylan Silver (09:34)
two miles from the ocean now.

Lenny Sharp (09:35)
miles from the ocean

that way. Well, I’m having a good real estate year so after you get down there and figure out all the numbers let me know maybe I’m gonna buy a condo down there.

Dylan Silver (10:19)
I wanna ask you about traveling, because you know, you’ve been, mean, Yosemite is an amazing, amazing destination. I’ve been there once when I was a young kid. I don’t really have a lot of recollection of it. I’m 31 years old now, and I’ve traveled Australia, Latin America, some areas, but I, and I really need to do more of that. I really need to do more of that. But I think travel is one of the things that has really expanded my perspective. ⁓

Dylan Silver (10:46)
so much and actually one of the reasons

Dylan Silver (10:48)
probably why I’m so passionate about real estate. Has it had any kind of a similar impact on you?

Lenny Sharp (10:51)
you? Well, I mean, I think so. In fact, living in Japan, we basically had lots of friends and family come out of the woodwork that wanted to come visit us, right? So we effectively became, you know, hosts in Japan, met new people. mean, literally met somebody on a cruise from Australia that we let stay in our apartment one night. So

You know, like I would say that that kind of scratched that itch for us and got us thinking about hosting. And it was all related to travel and meeting fellow travelers. So, yeah, I, you know, I believe that’s true. And I believe that. And again, one of the things I tell my investors is. You know, investment dollars and cents return on investment, all that. That’s great. But if if you don’t.

feel like you have some element of like the gift of hospitality and like that, then then don’t buy a vacation rental because at the end of the day, the problems will outweigh, you know, the return on investment and you literally have to be able to either meet the people or read their reviews or communicate with them and feel like, hey, I’m making the world a little better place because I’m creating this great spot for people to come.

Dylan Silver (11:44)
Yes.

100 %

Lenny Sharp (12:08)
And so that has to be part of the equation. And just one other aside that ties together vacation rental and travel. So we had a couple from Germany literally stay at our Airbnb at our house for their honeymoon. We hung out on the deck with them. We drank wine. We ended up traveling to Germany and hanging out with them. They didn’t have a place we could stay, but like we made these like lifetime friends through vacation rental. And then

We literally found out that they were pregnant before their family did. I mean, we got the ultrasound. I mean, so my point is, is something that can seem like a transaction or like a very casual kind of interaction can actually become something. I mean, we stayed at another Airbnb in France and, you know, go, we went and watched him play live at the bar. And then when he came to the States, he came and we let him stay at our place for free because we built a relationship. So

Yeah, think, I think, unlike other investments, know, short-term rental, investing can create something within you that actually will make your life much richer. And, and that’s why I recommend it. one of the interesting things you hit it, you hit the nail on the head. had a guest who told me, you know, you would think that it’d be obvious that if you’re going to do Airbnb hosting that you have to like,

Dylan Silver (13:16)
huge. One of the interesting things you hit it, you hit the nail on the head. I had a guest who told me, ⁓ know, you would think that it’d be obvious that if you’re going to do Airbnb hosting that you have to like

Airbnb hosting. But there’s a lot of people he said who get into Airbnb hosting and don’t like it and then they might not make money doing it. And it’s because you actually have to like being a host. You know, you have to go in liking hosting if you don’t like

Dylan Silver (13:43)
being an Airbnb host or a VRBO host or whichever platform you’re using, it’s gonna be grading on you and then it’s gonna wear you out, right? So you actually have to like being a host.

Lenny Sharp (13:44)
even know what it’s like to host on that platform, but there has to be something in you that likes to provide a place for people to stay. And then that can kind of go from there and then you get into the specifics of the platform or Airbnb or whatever.

yeah, I definitely, I see that a lot. And quite frankly, some of that are, up being buyer investors that turn into listings because they decide it’s not for them.

and you know and that happens and everybody’s got to kind of find their own way, but I I I really like I said I encourage them to look deep within themselves and ask them if if they really like the idea of doing that even if they haven’t done that before and The other thing and I’ll just kind of touch on this one of my sort of taglines advertising kind of positioning is this concept of free mountain getaway So it’s like okay. I’m not

focused on necessarily the maximum cash on cash returns, what I want is a home near Yosemite that I can use anytime I want with my family and it will pay for itself, making it free to me. And I’m telling you, those are my absolute favorite clients because number one, maybe their investment expectations are maybe a tempered and maybe a little more realistic.

They love the idea of staying themselves and they’re going to use it themselves, right? And then they also choose a home they want to stay in. And then because they use it themselves, all those little annoying things, like they don’t see it as, I just have to spend this money for these guests that I don’t care about. They’re like, ⁓ we buy that new barbecue and we’re going to love it when we’re at the house. And guess what? All the guests get to enjoy that new barbecue as well or the hot tub.

Dylan Silver (16:17)
That is exactly

right.

Lenny Sharp (16:19)
or the game room or whatever.

I mean, that’s really like, that’s how I would like to see my, lot of my clients see this opportunity is you can get a home that you can use any time and it will pay for itself. I mean, that’s awesome. And by the way, it’s going to appreciate and you’re going to have, you know, wealth building for the future.

Dylan Silver (16:40)
I feel that I’m sure you must feel super passionate about Yosemite and I feel the same level of passion about like Dominican Republic Airbnb’s, which by the way, Latin America Airbnb’s short-term rentals in general are huge. Huge. Probably you saw a similar thing happening in Japan as well. Like as big as it is here, it felt even bigger over there and I couldn’t believe it. Right. I was like, man, this feels like there’s a ton of Airbnb’s here and sure enough it is. I want to want to pivot a bit here though Lenny and ask you about

Lenny Sharp (16:43)
super passionate about Yosemite and I feel the same level.

republican republic every week by the way Latin America every week for tomorrow’s here it up bigger over there and i couldn’t believe it right now this feels like a whole and sure enough it is i wanna i want to be here the line yeah about that

Dylan Silver (17:10)
Folks who may be looking at areas of the country and they’re thinking about maybe a Yosemite, but they may be thinking about something on the complete

Lenny Sharp (17:10)
complete opposite side. may be looking at the Carolinas or like, you know, Vermont and other areas and they’re thinking, where do I go? What makes someone drawn to Yosemite? And then who’s kind of the person who goes and buys in Yosemite?

Dylan Silver (17:17)
opposite side. They may be looking at the Carolinas or like, you know, Vermont and other areas and they’re thinking, where do I go? What makes someone drawn to Yosemite? And then who’s kind of the person who goes and buys in Yosemite?

Lenny Sharp (17:30)
Well, I mean, like I said, I think it starts with like, where do you like to go? So, you know, we tend to get hikers. I mean, like a lot of our guests, they’re literally up and out six in the morning. We don’t see them till night. I mean, so I think that

There’s gotta be that sort of love of the nature and outdoors. So I think that’s a big part of it. And again, I think the concept of like, buy where you like to go and that’s probably gonna work out. But I’d say also, and I get this question a lot, like, you know, what about saturation? Is the market too saturated? Are there too many Airbnb’s? But, you know, I think that, you start with like the market.

I mean, four million people come to Yosemite every year. So, and by the way, there’s not that many places to stay inside Yosemite and it’s crazy expensive. So they immediately start looking outside the park, where can we stay? That’s a nice house, reasonably priced and get to the park. So we have a sort of a baseline of a ton of people. And then we have these communities that are quite affordable. I mean, our, you know,

⁓ median home price here is probably about $450,000. And I’d say the average Airbnb does probably, you know, $60,000 or $70,000 a year, an extra $15,000 if you add a hot tub. mean, so like the numbers work out. So there’s a baseline that makes sense. The numbers work out. And then you just make sure that you’re tweaking your particular property in such a way.

Dylan Silver (18:48)
Yeah.

Lenny Sharp (18:59)
you know, with the photos, with the amenities that you just rise to the top. And if you’re in the top 20 % of this market, you’re going to be successful. And we could take, you know, we could bring on another thousand or 2000 Airbnb’s and just, just don’t be in the bottom half and you’ll do fine.

Dylan Silver (19:16)
I tell people that I’m ⁓ moving to Dominican Republic, I’m in Dallas right now, or DFW area. I really like it over here, I like Texas in general, but I’ve had so many investors on the show from Florida, from South Florida, and then the West Coast of Florida. People from all over, people from Wisconsin that relocated to Florida, and Idaho who are snowboarding in Florida, and New York and Northern New Jersey where I’m originally from in Florida.

And I said, man, there’s something in the water in Florida, because all these real estate investors go down there. What is it? And I’ve been through Fort Lauderdale now like five times in the last 10 months. And I’m like, I get it now. Like, this is amazing. It’s like this year round. Just have to dodge a hurricane every now and then. But

Dylan Silver (20:00)
then I I speak to, you know, ⁓ folks like yourself. I get to Lenny Sharp in the Yosemite area. Now I’m thinking, now I got to go look at Yosemite. I got another place that’s on the map now. It’s so hard to decide at this point.

Lenny Sharp (20:13)
I mean, it’s beautiful. And I tell you, go back to Yosemite as an adult now and you’re just gonna be blown away. Because as a kid, you probably didn’t appreciate it. I mean, it’s breathtaking. I just want to hike this Sunday.

And the one thing that still amazes me, like Yosemite is a place you can walk around and literally walk off a cliff and fall 3000 feet, right? There’s no safety rails. And so there’s something attractive about that. It’s like, I think it taps something deep within us that like, I’m going to go to this place that’s gorgeous and it’s still wild, right? I got to be careful, you I got to pay attention. But I think there’s something about that that attracts people, right? This isn’t

you know, prescribed, controlled, you know, you’re in a crowd with railing and safe, you know, that’s like you, can go it’s thousands and thousands of acres and you can just explore and see amazing sites. And we were on a hike that literally it’s, it’s like not on any of the hiking trail apps. Like we were blazing our own trail and we got to a point where we were seeing stuff that most people don’t see. And that’s, know, that’s remarkable. It adds to the experience.

Dylan Silver (21:22)
That is attractive to me. I definitely understand that. It’s like, well, worst thing that happens is we fall off a cliff, but the best case scenario is we have to see the cliff, we walk straight through it, we get life without guardrails, and it’s so much incredible, incredible immersion into the other, mean, frankly, otherwise digital world, right?

Lenny Sharp (21:22)
Yeah, so the best place to go is just go to sharpmountainhomes.com I’ve got links to kind of all my content. I’ve got a link to my free mountain getaway website as well and then Links to my YouTube channel. So my YouTube channel, it’s long form the YouTube

videos that I post are sometimes 20, 30, 40 minutes long, but they’re really designed to be educational. it’s Yosemite Area STR Investors channel at YouTube. I talk about the different areas. I talk about the revenue expectations, the amenities that will work. I tour homes. I present potential properties for investment.

I talk about regulations, which are obviously something you have to pay attention to. So yeah, those are the spots. If you just start with sharpmountainhomes.com, you can find me, but yeah, reach out. I just love what I do. I love helping people and it’s working out. Lenny, thank you so much for coming on the show here today. Okay, thanks Dylan. Great to meet you.

Dylan Silver (22:46)
Lenny, thank you so much for coming on the show here today.