How Health Challenges Led to Boutique Vacation Rental Ownership

0:00I was having health problems basically health challenges and I went I would spend a lot of time out of New York because of the weather and so I would rent airbnbs all over all over the world and all over the country and so I stayed in I think over 35 different airbnbs over the years and so I was actually a guest first and I'm sure as anyone who else has stayed in in airbnbs there isn't really a level of standardization it isn't like you go to a Marriott and you're going to get Marriott level it's like you may meet a dog who wants to eat your hat true

0:49Story you may walk in and the place smells like mold and you get sick for two weeks or you may walk in and there's a plugin and I'm very I'm a extremely sensitive traveler I'm completely allergic to like fragrance alcohol including rubbing alcohol so I'm kind of that you know princess in the PE type type traveler that I needed k a kitchen so I was like of course not well enough and had never really thought oh would I be a host it was just like I was sort of taking notes like okay I would do this differently this was really good this was not so good and then you know fast forward

1:37To like I was what 19 18 years into my my stint in New York and I just was like okay I was kind of burned out I was honestly burned out from trading hours for dollars because that's what you're doing as a stylist you only get paid when you show up and you have to be like sparkly and you have to be like a and you have to be like funny personality which I have but it was just like because of the health stuff I was getting burned out and my grandfather was in 2018 it you know I got back from Europe and it was like super clear that he was you know going to transition yeah and he was like a dad to

2:26Me and so I was like I just had this huge calling I just wanted to be by his side even though I was a granddaughter I was just like wanted to be with him and hold his hand so I came down to Florida to to Jupiter and it took about eight months for him to transition it was he was super super healthy was 102 wow and during that time of you know holding his hand and buying flowers and kind of being the the you know more moral support I had a lot of downtime at night and so cuz I was alone in the house and with nurses there's not much to do so I was like looking online at real estate because I was super curious I was like I

3:14Wonder what it cost to buy a house around here and I realized that if I sold my New York place that what I could buy down in Florida was monumentally better and I so I basically you know quickly very quickly within like two months sold because I was like I had tried to sell my New York place before sold New York bought a three-bedroom two bath house that was walking distance from this little local Beach that wasn't really advertised as a beach it was a park and then it had a beach but no one was really like touting how great it was and I was like scratching I was like this is so strange and my plan was to

4:03Rent it out but like rent out rooms and live there but event you know originally you know my grandfather was still you know transitioning so I basically moved my stuff in and I pre-sold it on Airbnb with the real estate listing photos and I got a family they booked it for six weeks so I moved in two weeks got it set and then rented it went back to my grandfather's he was like beyond beyond happy it was like he he he couldn't have been happier he was like you're a Floridian now and the good news is you're going to have to buy a car and I you buy a car I mean he was like so it was like he was so content that

4:52I was now living in the state and then 3 weeks later he passed and you know my house is rented I was supposed to live in and my aunt she thought I was insane and she's like I don't understand why why did you buy a house you not going to live in can't afford to live I you know you're like you know what what you know she just was like confused and I was like I think it's going to be okay and I went traveling I was like grieving I stayed on with a lot of f family and friends for the first six months and I really kind of like I tested the market I I want wanted to see okay in the beginning it wasn't like there was this master plan it was more like I just put one foot in front of the next and I tested renting out rooms and

5:40That like did not fly and then I tested renting out the whole house and it was like that was what everyone wanted so I was like oh I guess I can't live in the house and rent out the room I guess this house just really rents well as a whole house because you know three bedrooms two baths private pool beautiful walk to the beach it's like every check mark that every Floridian wants yeah and so I accidentally stumbled upon a gold mine that you know that house just performed so well with me just kind of trying it winging it and then I was such a natural host because of my customer service skills from styling and you know my ability to

6:29Like just really be human for the guests really you know ask them what do you want not just here's a bottle of wine you know what I mean so I've really the whole time I feel like my whole I'm driven by the guest experience I'm driven by like how can I make it the perfect stay for them m and not oh well statistics say that you know snicker bars are the bestselling candy bar so you should stick Snickers in your short-term rental house yeah it's like well what if you I mean and here's the odd thing is that in the beginning I

7:17Was shocked at how many fellow Travelers showed up and stayed in my house who were dairyfree gluten-free paleo you know allergic to Sugar allergic to something thing having health challenges going through a surgery I was attracting like-minded people which was like whoa interesting yeah so how do you how do you customize it you mentioned not just leaving a standard bottle of wine but how so do you have conversations with them in advance before they show up and sort of offer con I like super communicative with the guest in advance of their arrival in the beginning I was having conversations with every single guest

8:06But I found that some people don't really want to have that conversation you know some people really want to lean into like learning about you and then some people are just like let me do my thing and so I've learned to kind of follow their lead and then any opportunity I get to kind of ask them oh like for your starter I mean we we provide for stays over a week we provide starter breakfast groceries and so the the average person would just be like oh yeah let's just throw some eggs in there and I like go further I just say you know your stay qualifies for complimentary groceries give me your list and I'll shop for you and then I at the end I say you know

8:55Special diets you know catered to there's like a line about you know you're not weird because you drink almond milk or rice milk because Normal travel is completely skewed in the you know Mass Middle America you know normal grocery store slant you know Coke Pepsi sugar candy coffee I mean although I will say most of my guests love coffee I don't personally drink it but everyone loves coffee that stays in my house so what did I do I provide three different ways to make coffee espresso drip and French Press wow I mean I'm I'm about to like even go pourover because I'm like oh maybe we should add pourover it's like coffee is the

9:44Is one of the things that is very important to my guest yeah which like I don't drink it and then I'm a tea person so we put tea and we put you know all the coutal but I I don't assume that everyone drinks milk MH yeah so so how do you manage that process because I think that's awesome that you do that and I I think you're right everyone's got different unique tastes and different unique dietary requirements you mentioned you traveled quite a bit while in the beginning while you were kind of getting started with this how do you manage this process are you actually driving to the store to to to purchase these products for them and what's what's your system look like so when I first started yes I

10:32Was out of state so I was managing everything remotely I was using apps like Amazon Prime from Whole Foods I was having things delivered and I was relying on cleaners but then I ended up living here full-time during the pandemic and there was a point where I made a decision and I was like look you can like go traveling go somewhere else or you could like settle here and completely lean into this business and get super involved and that's what I did so yeah I am driving to the store I cleaned the house the other day and I have to say I did a really great job like I was kind of like in a hard place because the cleaner's daughter got sick and I was like well you know I I can do this yeah I

11:21Can do this so yeah I'm a little too involved for as a realtor but I feel like as I'm growing my real estate business it's nice to have to get your hands dirty to roll up your sleeve to to know like how much work is involved and what needs to be done I'm usually the last person who has eyes on the property before the new before the guests come in so like I take video I do quality control I make sure the gifts are right I make sure there's no like stray hairs but is that something that I think I like when you go to scale like you can't do that I'm I'm two properties but I'm actually thinking about standardizing because I use the scheduled messages a lot and

12:09I have a lot of pre canned messages and that keep that makes my business run really well but I'm actually about to add in a new one where it's like a a questionnaire like what's your favorite can't you know guilty pleasure what's your favorite you know what are you looking forward to do doing in the area you know and then I can potentially upsell them like a boat ride or upsell them in a local experience so I think I'm always thinking about okay how can I improve how can I go faster easier but then also how can I make the experience better for the guest yeah that's great it might be a little scary what you learn when you start asking people about their guilty pleasures but I love that I

12:57Might have to like do a cab yeah you know food and beverage wise I mean my demographic is families multigenerational families Grandma you know the kids and then the grandkids that's who usually although I've been experimenting we're in slow season here in Florida and it's extra slow so I've been experimenting with closing off two of the bedrooms and just selling the master suite and the house with a pool and actually we just had our first guest come and there was just like a couple they came to see the turtles and that was like a new guest Avatar and that was kind of that was kind of exciting and I've always real I've like the whole way I've realized because people will book my whole house and

13:46Then there'll be like two people that happens a lot and so I've in the back of my mind always like where can I find a one bedroom house with a massive pool massive backyard because that's what the Florida guest really wants they wants the indoor outdoor living they want to be near a beach they want to pool want privacy you know romantic but not shared yeah they don't want to share anything