Curating Memories: Large Group Stays Perfected with Kim Herrlein

On this episode of the Booked Solid Show, Gil is joined by Kim Herrlein, the Chief Leisure Officer of Purveyors of Leisure. Kim is a short-term rental operator who has mastered the art of large group travel through beautifully designed estate properties in California’s Coachella Valley. She recently expanded her hospitality vision by launching The Fainting Couch, a boutique hotel in Northern California’s wine country. In this episode, Kim shares her journey from real estate investor to STR operator, and now a boutique hotelier, with a focus on curating seamless, luxurious experiences for her guests.

Whether it’s hosting multi-family gatherings at her spacious estates or redefining boutique hospitality with a contactless model, Kim’s approach is rooted in understanding her ideal guest avatar and crafting an unforgettable stay. She also dives into her strategies for direct bookings, guest nurturing, and her belief in elevating hospitality through thoughtful design and personalized service.

Looking for an exceptional stay that goes beyond the ordinary? Discover the luxury and thoughtful service at Purveyors of Leisure and The Fainting Couch. From estate properties designed for large groups to exclusive boutique experiences, Kim and her team elevate every stay with personalized hospitality and seamless service.

Visit Purveyors of Leisure | Visit The Fainting Couch

Connect with Kim here:

• 🌐 Facebook – Purveyors of Leisure
• 📸 Instagram – Purveyors of Leisure
• 📸 Instagram – The Fainting Couch
• 🌐 Facebook – The Fainting Couch Hotel

Transcription

Gil: Hey folks. Welcome back to the Booked Solid Show, the podcast where we’re bringing top operators to discuss marketing, revenue management, and guest experiences to drive towards being booked solid.

On today’s show, I have Kim. She is an STR operator with properties in Coachella Valley, or the Palm Springs region. She has really large estates, which sleep anywhere from 16 plus to 20-something guests, and she’s really dialed in and figured out how and what her guests are looking for, specifically the person that’s booking.

Some of the conversations that we go through are really around the service of really how do you think about that guest, what they’re going through, and the service that you want to provide. We go into a pretty deep conversation, specifically about this and specifically about her avatar as a reference point.

Some of the things that we’ll kind of get into is really knowing that a guest that is coordinating between 16 different people, how do you actually craft the services for that? So she has, for instance, onsite staffing to make sure that the guest that is booking is really hosting for the rest of the family and has everything that they need.

She also talks really about what it is, the feeling that that person has, how she really messages that person both before and after the stay, really understanding that guest avatar. So she is a person that really has dived deep into really understanding the ideal guest avatar at a different level.
At the very end, we also talk a little bit about AI and how it’s being used in both our industry and AI in general. So this is a really fun show. I’m really happy, happy to have her on here. So without further ado, let’s bring her in.

Gil: Kim, welcome to the show.

Kim: Thanks, Gil, for having me.

Gil: Yeah. I’m so excited to see you at the summit in a little bit. I don’t know when this show is gonna air, so this may air before or after that. But I’m excited to just meet a lot of the hospitable hosts over there.

Kim: I know! It’ll be nice to finally connect in person with a number of people.

Gil: Yeah. Yeah. I’m excited for that. It’s amazing. It’s amazing how much of the industry that you just meet remote. And I don’t know if this would’ve happened if the pandemic didn’t happen, but like, I felt like the pandemic has really opened up everybody’s ease to meet someone and get personable with someone even though they don’t get to see them.

Kim: Absolutely. And it’s amazing. There are a lot of horrific things that came out of the pandemic, but there’s also a lot of great relationships that were built along the way too.

Gil: Yes. The way I got involved with Hospitable Hosts was completely through Julie George from Clubhouse Days with Jody. It’s amazing what it’s grown to, and having been an author in the first volume and now seeing where it’s gone, it’s exciting.

Kim: Yeah, I think that’s probably a good segue into just kind of giving folks an introduction on who you are. So Kim, do you mind giving folks a glimpse of who you are?

Kim: Sure. I started Purveyors of Leisure about 10 years ago. We just celebrated our 10-year anniversary, and I wound up in this industry accidentally. I think that some of you may resonate with that. I said yes to a friend, a dear friend of mine who was a real estate investor. I also was a real estate investor and had my, you know, what handed to me in ’08 and was a little bit nervous about investing again.
But I was certainly a hell yes when it came to looking at properties and designing them. And so it started off with literally my good friend asking me to look at some properties with him. And it was in the Coachella Valley, and the first property that he purchased was across the street from Coachella Music Festival.
And soon we learned what an incredible opportunity and incredible margins we were dealing with in this, in this particular valley, Palm Springs. As some of you may know, it might be easy to pinpoint where we are. So I said yes, and soon before you knew it, we were up to 14 properties, and things were ramping up pretty quickly.
I started with a, um, I brought on a VA team. I had an operations director, I had boots on the ground in five regions, and ultimately built what I thought was, you know, a very strong foundation for a property management company.
Simultaneously, I started to realize that the market was at its top, and both myself and my business partner made a decision to start exiting. And so we started selling off properties probably at the height when most people were getting in, which was very profitable for us and also gave us the energy and excitement to pivot to boutique hotels.

Gil: So currently we just launched out our first boutique hotel last September of ’24 called The Fainting Couch, and that’s located in Northern California, about 45 minutes north of Napa County. And yeah, so that’s, I mean, it’s been a ride, it’s been a decade.

Gil: And so you still manage your short-term rentals. You still have a few in the Coachella Valley, is that right?

Kim: That’s correct. Yeah. So we held onto five estates. They range in size from six bedrooms to 11 bedrooms. We have pretty much always hosted. The group size is typically around 16 and goes up to about 26 in two of the areas that allow for that.
And we have just embraced large group travel. We’ve really connected with the essence of large group travel, and that’s primarily ’cause that’s how we used to travel.
We would travel as a group, friend group to Mexico and the Dominican Republic, and we would travel 14, 16 deep, and we’d have concierge services, and most times we didn’t even leave the house. We’d be on a beach somewhere and we’d have a chef and we would live it up and realize this is what other people want to do.
And that’s really that. It was a combination of my interest in real estate and John’s investment interest in real estate as well as my interior design interest, coupled with the fact that we love to travel and we love to travel in large groups.

Gil: Wow. So were your first few properties also estates, or did they evolve into that as you kind of like niched down into what you really want to focus on? Because right now, most of all your properties are now estates, but I’m not sure if the few that you offloaded were also as well.

Kim: There were like, I’d say two that wouldn’t be considered estates. However, one thing that we were really early on was understanding the importance of heads and beds.
We would take a property, for instance, the one right now that’s still our premier property. The Coachella Estate is a 5,000-square-foot home on two and a half acres with a pool and a pond. It’s absolutely gorgeous, a park-like setting.
When we first purchased it, it was only four bedrooms because people don’t design 10-bedroom homes. Like, that’s unless—and if you think about it, a 10-bedroom home would be typically 20,000 square feet and some luxurious sprawling 20 acres estate or, you know, something really kind of grand.
So what we were doing was taking things that obviously spatially, like if you—we all know for vacation, especially where most of the activity is outside and having fun and in a pool, people are not in their bedrooms.
They’re not coming, they’re not gathering with 16 people so they could go be isolated and read a book in their bedroom.
And so we realized the bedrooms did not have to be that large. They just had to be obviously well outfitted. Every—as many bathrooms as we could put in, we did.
So we took a place that was a four, three and a half, and now it’s a ten seven.

Gil: Ten seven.

Kim: Mm-hmm. And we didn’t—mean, we added some, we enclosed some patios that were in the front that no one’s gonna sit in the front when there’s two acres behind you.
And yeah, we were able to make it into a ten seven. And that property, you know, is amazing. We just actually added, we did do some upgrades recently.
We added a pickleball court, we added a barrel sauna, we created a beach volleyball. We always had the volleyball net there, but then we brought in the beach sand and just kind of elevated the experience of being in a resort.
And I think that has always been our message. Like, you come here, like we don’t want you to leave.

Gil: And it’s easier if you think about it. I don’t know about you. I know you said you have children. What’s it like to go out with three families with a couple of children each for dinner?

Kim: It’s rather hard.

Gil: So like, I think even like spring break and summer, we tend to travel in groups if we do travel, and it’s only three families. But a lot of times—and we actually did this during spring break—we went to Tahoe and we rented a place, and we had four bedrooms. It was enough for three families of us, but like, we spent a majority of the time on the property itself.
We still had snow there, so we built a snowman in the back, and we just packed the backyard. It was just a really big backyard, and we actually spent a lot of time there.
And given that our kids are young, it’s actually a lot easier to say, “Oh, put on your snow boots, go outside and play.” And we didn’t have to drive outside.

Kim: Yeah, it worked out really well. Like what better way to spend the day than to play in snow?

Gil: Absolutely. And here it’s playing in the sand and in the pool. And I think one of the other things is for the person booking the trip. This is something that, you know, really comes up often for us, is really us understanding the pressure that the booker is under.
Because if your task is, “Hey Gil, we wanna get together 20 people, and it has to be able to outfit it for grandma and your children,” you’re under a lot of pressure to like make everyone happy, right? To really find the perfect place.
So I think we really understood that early on, and that’s why I say like, the only two homes I would consider were not estates, but we averaged—our average home was eight bedrooms for a very long time.

Gil: Got it. Got it. Well, that’s amazing. So talk to me, and we talked a little bit about this during—before the call, and we both joked that we should have probably rolled earlier because we went into a deep conversation.
But to kind of catch folks up, you talked a little bit about kind of like how you think about your guest stays.
And I want you to kind of lead the listeners into kind of our conversation here about like, what do you think about are the kind of like the challenges and actually probably more stepping back. How do you think about your ideal guest avatar and what they need to have a great stay and how you take that into consideration when you’re crafting that entire journey?

Kim: Sure. First off, we have an incredible team of VAs that are ready to answer any and every question available and stay on top of the guest as they’re inquiring.
I think something that people forget is if you’re tasked with “Go find this place,” now we are in a very smaller niche. There’s a lot less competition, but the competition has grown, which is also the reason we’ve upped our ante on the amenities.
But despite that, you may send six messages, eight messages, right? And whoever’s handling you professionally and is welcoming to answer your questions like, “How far is the bathroom from bedroom seven? So Aunt So-and-So is comfortable,” right? And we have that answer.
And so we’ve learned over time that that was such an incredible edge over other hosts.

Kim: And then secondly, once they do book, you know, we offer concierge services. Everything from bringing in massages, yoga teachers, fitness instructors, and obviously chefs.
And that’s also a bonus for people who don’t want to leave a property, right? If you can bring activity to them, especially eating, which is nice to not have to leave.
That was also a really positive… I’d say it brought a lot more positive impact on people’s decisions.

Kim: And then lastly, we host the guest. So albeit everyone’s contactless and all the ways that we have brought on tech to make it so less, I guess, in-person, we have actually always held onto the belief that the person who’s booked this is going to need as much help as they can get.
And the properties are pretty elaborate. There’s definitely a lot of systems, there’s a number of apps. There are things that need to be known, but most of all, it’s knowing you have someone that if you’re like, “Ah, I don’t remember how to put on that spa,” I know I could look it in the book, but like, “Can you just tell me?”
I mean, we send little videos. I mean, we are very, we’re very responsive and I think that has kept, you know, and what that does is it prevents you even from when you’re having an issue. Let’s face it, things happen.
I think another piece that we’re really strong in as far as that is, is really mitigating problems. When an issue arises, it’s like, we’ve got you. We will make sure that this inconvenience lasts as short a time as possible.
And you know that because you are basically being handled right away.

Gil: Yeah. Yeah. Yeah. So I think some of the things I picked up there is like, you’ve kind of staffed up your team to understand how to serve your ideal guest avatar.
And that’s both on kind of the VA front, where you’re making sure that from a responsiveness standpoint, if someone’s reaching out to you, either on platform or off platform, they can reach you and they can get those questions answered.
That also translates into the booking and making sure that your VAs are there to help answer any questions.
But it also sounds like you’re hinting that you have boots on the ground that are there to make sure that the stay is to the quality standard that your customers expect and that they want to deliver.

Kim: Absolutely. I think, I mean, you know, to stay at these properties, it’s not inexpensive.
And I think there’s an aspect of, again, really giving the confidence—it’s kind of the way I like to think about it is that when a guest books with us, they become the host.

Gil: That makes sense.

Kim: Because they really are—they are hosting two or three families, or five families, or 20 friends on a bachelorette party. You know, it’s this concept that there’s an itinerary, and they typically are drawing up spreadsheets, and someone’s maybe more organized and helps out this person who booked.
But for the most part, the person who books or the person nearest to them who’s helping with the itinerary has a lot of questions, and they want to create this kind of—as much as it can be—an inclusive experience for their guests.

Gil: That’s interesting. That’s interesting. You mentioned the itinerary. Do you get involved in any way, or are you there really to support to make sure that they have all the answers to draft that itinerary for their stays?

Kim: We are as available. I mean, we offer them about three weeks out. We let them know at booking that we offer these concierge services, and then like most of us, once we make a decision, we don’t think about it for three months. Like, “Don’t bother me with any more information.” Right?
So we’ll wait till about three weeks to a month. It depends if the season’s really busy, like if it’s in-season where it’s harder to get vendors, it’s a month, but typically three weeks.
And we reach out and just, you know, we send a form for them to fill out if they want anything from restaurant recommendations to babysitting to chef, you know, fitness—all types of different services.
We’ve had a lot of… and sometimes we just celebrated our 10th Coachella weekend, first weekends, and our chef basically catered for five days, a group of 18 people.

Gil: Wow.

Kim: Yeah. And we talked a little bit about your website before, but one of the things that I’ve noticed is that you’re trying to also weave in some of that information kind of in your website.
It may also be in your listing descriptions, on-platform as well too.
But how do you think about creating that—even that experience, even outside of just the messaging that you have there?

Kim: Well, I mean, the host does reiterate it when they check in that they’re there for any kind of recommendations and such.
Unfortunately, it’s a little too late sometimes. Some people are like, “Oh, can you get me six massages tomorrow morning at 8:00 AM and we’d like all males,” or whatever, you know. Like, sometimes, no, I can’t.
You know, so there’s definitely some of that.
But I think for the most part, I think because—and we see it in our reviews—they feel supported. People feel extremely supported when they work with us and that, you know, we are available to answer questions and more so find out information.
So in other words, you’re coming and you’re celebrating your daughter’s eighth birthday and you would like a balloon display, right? And they’re not from the area and they’re driving three, four hours.
We do have, most of our—I’d say a majority are from LA or San Diego that come to the Palm Springs area. So it’s, you know, a drive market.
But for the most part, yeah. Could they Google stuff? Of course. But isn’t it nice that I can offer my favorite balloon display artist and get her to do the work and they get, you know, to choose, and we know it’s going to be on time and it’s going to be professionally handled?
So that’s the kind of thing that I like working with.

Kim: And this is also another huge part of, from the other side, having good business relationships with vendors around the area. I think that’s critical, you know, when you’re really trying to deliver. It’s not just a recommendation.
Like, I’m putting my name on the line if I say this person will do a good job. But we will do it.
And I mean, we’ve had some interesting ones where like, you know, finding something that is not available nearby or what, you know, just—we are, we’re just creative.
And I think actually my VAs enjoy it because it’s kind of like a little bit of a treasure hunt. It’s a little scavenger hunt trying to find the best.
Like, I mean, this one person wanted a specific cake. I mean, just all kinds of requests.

Gil: Yeah. And I think that’s very special because I think the essence I’m getting is really—it’s really way beyond just the stay itself.
It’s not just the property that you’re living in. And a lot of times we think about amenities and how do we pack this place with amenities that people like, but what I’m gathering here is that that’s not just it.
And it’s not just answering questions, but there’s this service layer that goes above it.
And a lot of times we call that hospitality, but it is a service that you are providing to your guests.
And it may or may not be something that they’ve necessarily paid for, but knowing that you are there to support them during the trip makes a huge difference on their impression and the more likelihood that they’re going to actually book again or even refer you to others.

Kim: Correct. Absolutely. I’d say the majority of our reviews state something to that nature.
“We’ll be back. We’ll definitely be back.” You know, “Don’t hesitate.” Like they’re telling other people, “If you read this review, don’t hesitate. You have to stay here.”
So we have, you know, very positive, positive reviews. And I think, like I said, it does, it also has this extra layer of protection because they know that you really care about their stay.

Kim: I mean, I think that’s… we’re all frustrated, and I won’t name names on OTAs that drive us crazy, but there are certain ones that if you have a problem, it’s like good luck.
And I think this is really trying to create, you know, provide the absolute polar opposite.
Like you may come in, you may run into a problem, there may be an issue—that’s just the way life is.
And that’s how, you know, I mean these properties are not… same goes with a hotel stay.
And I think that’s really early on what we realized is that because people would not be leaving the property—because it’s too hard to mobilize 20 people—that we wanted to create a resort stay so that you felt you just rented your own private resort.
And that became kind of, that was in… that’s in all of the way that we approach, whether it’s marketing, you know, in communication, and in operations, you know, with how we lead.

Gil: Yeah, yeah, yeah. It’s almost like you have that vision in mind.
You’re not just thinking about the property itself, but all the things that have to go around it.
That’s amazing.

Kim: We joke, we say we take leisure seriously, so you don’t have to.
I mean, that’s our tagline, right? It’s like we really… yeah. It’s like this, this is what we’re here for.
We’re here to provide.
So that you… and I think that’s another interesting piece when you are the booker there, because you’re primarily tasked with, you know, choosing this spot.
You may also be handling the groceries, handling the itinerary, like I mentioned.
And I just think there’s an aspect of relief when they realize they have partners that know the property really well.
We can suggest, like, we will ask, they’ll say, “We have two people. They don’t really know each other. Could they possibly share the bunk room?”
And we can answer, “We would suggest they sleep on the two lower bunks. We have this divider that goes…”
And so they have valuable responses.

Gil: How does this translate to you now really spending a lot of your focused time on your boutique hotel?
How does this translate to operating a boutique hotel? Is it different in many ways? Is it the same?

Kim: Well, I joke because our booking window for these estates is like somewhere between three to six months depending on the time of year.
Sometimes closer to a year, nine months or a year around the holidays and around festivals and so on and so forth.
With a hotel, someone’s probably booking right now as we’re talking, and it’s just happening.
And I think the fact that we have been so systems-focused for so long and tech-focused for so long that the transition was a… or I should say like, I wouldn’t say it was seamless, but it was a lot easier than I think had I just started from scratch.
And I think because we already have this mindset of how we want the traveler to feel… I mean, the reviews are, you know, that this is so well thought out, that the design is so playful. It’s moody.
And people will say, now this is the irony… so our hotel is a contactless hotel and we don’t have a front desk and you don’t get hosted, right?
So it’s a complete opposite of what people pretty much are doing in the sense of that most people are not hosting vacation rentals. And we are.
And I think the interesting part about it is people are writing, you know… people, this is still a newer concept.
The contactless, no front desk—you know, I mean, people in our industry are very accustomed to it, but it’s still new to the general public.
And you’ll be surprised how many reviews, like, “We didn’t even miss the front desk,” or “It was so seamless. It was this… it was flawless. People answered questions. They even sent us back what we, you know, left at the room.”
And so they’re starting to equate, just because you don’t have a front desk doesn’t mean you have no customer service.
They’re getting incredible customer service.
They have people answering them.
You know, we have… I mean, basically, we are… we’re dark from 3:00 AM to 8:00 AM.
That’s our only timeframe. And they’d better not be calling us because that sounds like an emergency. No, just joking.

Gil: Yeah. I’m guessing you have in-house staff on your boutique hotel, for both on the housekeeping and maintenance side. Is that right?

Kim: So we have housekeeping and also maintenance, you know, groundskeeper-type person. But I mean, they’re fluid. They work with our schedule.
They kind of make their own hours. They’re contractors and it’s been awesome.
We have been able to really deliver.

Kim: Again, it’s systems, right? It’s like having been in this industry for a while, how do you assure quality? With a system, a checklist, and proof, right?
And pictures and people understanding. I mean, one of the nicest things is that I’m able to convey how much this means to me—that this room is set up exactly as I designed it and that this light is on when that guest comes in.
There’s just certain things that we can control the tech so that if… like, in other words, how many times have you gone into a hotel—you know, and this is more motel world, let’s face it, than hotel—where you’ve gone in though and it’s so hot, or it’s so cold because you haven’t turned on the split or the unit.
So we do that ahead of time with tech.

Kim: It’s really… it’s just so… we’re so attuned to people’s needs, and what I love is that I’ve been able to convey that to people on the team.
And they feel the same thing, and they’re getting those reviews, like the housekeepers are being praised for how clean it is, how perfect it looks better than the pictures—just really great, great reviews.

Kim: And our intent with the hotel, as I mentioned before we were talking, was based on all of the people that we’re hosting on a regular basis, we thought, how hard… you know, this has to be easier to streamline operations and centralize all of the different systems.
And it is. And it is really picking up. And we are now, we have, I think, six buyouts on our calendar.
We just, we had our first one this last weekend, it was really incredible.
We had our 10th anniversary Coachella weekend at the Coachella Estate—an incredible time. And then we had, all the estates were booked and we also had a buyout at The Fainting Couch.
So I had a really… it felt really good this weekend. Well, it felt good on Tuesday. And yeah, it felt like great success and it just was kind of a nod to, you know, doing it, doing it well, which is important.

Gil: I think some of the things that I noticed is that it’s a combination of like several different ingredients or aspects that you’ve been investing into.
One is the vision of the overall stay experience that you want to deliver and really translating that to your team.
And then the systems that you have in place—both in the… it could be SOPs, it could be the technical side of it.
And also then the team structure to make sure that they’re there to actually execute.
Because it’s not just about the SOPs, but actually finding the right staff and leveraging their capabilities both remotely and in-person to make sure that you can actually deliver that service.
I don’t know if there’s anything beyond that, but that’s what I picked up as like, what is the perfect recipe that you’ve definitely been… I’ve spent a lot of time working on and modifying.
And you know, we’ve ramped up tech, we’ve taken down tech, we’ve added more people, we’ve taken down people. I mean, it’s literally just trying to find that balance based on really the portfolio.
And I mean, at this point, I have numbers of ideas of where to go next, but I think for right now, being Wednesday after the 10-year reunion, I feel very much like, I’ll sit in this moment and be… and be proud.

Gil: Yeah, actually, that… that actually is a question that I had in the back of my mind. You—and it might not be immediately that you’re gonna be focusing on—but you have done quite well in making sure that you can deliver a really good experience for large stays.
And now you’re doing this, you’re scaling that with boutique hotels.
How do you see your evolution evolving with time?
What’s like your grand vision of things? And I know you wanna take in the moment and you want to live in the moment, but I’m also curious of like, what are your ambitions of conquering?

Kim: I think as far as within this industry, I would absolutely be interested in another hotel renovation and design.
I have been working on a front desk alternative concept with my partner John called Always Receptive.
And I think we’re gonna do… it started as kind of a consulting basis where we, in essence, take the playbook that we just created and keep, you know, kind of fine-tuning as we learn more about hotel operations.
And this is a small, you know, this is 18 units with a house, so it’s 20 bedrooms and it has, you know, a communal space and pool and lovely chandelier park for events.
And now we’re getting, you know, a little bit more into upselling and really creating breakfast in bed. And we have the hiking picnic to go and the welcome platter.
So we’re starting to add kind of more and more things. I will have various workshops going on in the house, like just trying to create activities.
We’ll have wine tastings, all types of different things. So we’re kind of still working on that, curating that.
I think that’s the word. I think that’s what I am. I’m a curator and I feel really comfortable stating that.

Kim: And I think if I could help others that are like, I’m in the boutique hotel space, I have these ideas…
And I have to admit, like, because of these podcasts, I really have been able to connect with a number of people who are speaking with me about design concepts and/or how did you do it and what made you do it.
And I’m taking a lot of calls because there’s a lot of inquiries around, you know, the boutique hotel space.
And I just think this front desk alternative, it’d be kind of neat to kind of… I guess white-label it, right?
Like where it’s like, I can take your brand, Gil, like you wanna work with this type of avatar and you know, this in this area.
And we would do the research, we would help you kind of build what that should feel like, and also train people to speak to those guests and really fine-tune that.
So these are just… that’s kind of what’s one thing.

Kim: I’d say the other part that I’m working on right now is marrying the two sides of me.
I have spent many years as a transformational coach.
I am trained to teach creativity and business, which is a course that’s taught at Stanford for 30 years now.
And a few other types of courses around that, which basically fine-tunes the concept of creativity and what that looks like in your business.
And I just feel so strongly that in our industry, as we are evolving and becoming more professional in some ways, we don’t want to get too far ahead of removing the human in the loop, as they say in AI.
And I think that certain aspect of it is your creativity. It’s your essence. What makes you… why do you want this?
What is your purpose? Like, what’s the meaning behind why you’ve gotten into this industry?
And I think the more you understand yourself and what makes you feel good, the better you’re gonna perform in that area.
And then also learning what you don’t like to do and learning that you may need to delegate that or, you know, rework it in some way.

Kim: So that’s kind of, you know, where I am. I am gonna be starting a hospitality mastermind named “Connect for Success,” and I’m looking for what I consider dream team cohorts, where it’ll be up to 12 women.
And that would consist of like a realtor, an interior designer, anyone that’s really an entrepreneur within the hospitality industry that’s interested in growing their business and working with other entrepreneurs that are, you know, that are touched by this industry.
Because there’s mortgage lenders and obviously realtors and trade designers and marketers and I mean, there’s so many people that this industry touches.

Gil: You said there’s a few things right now that, that strike me.
One is kinda like on your mindset stuff and bringing kind of that back into play and everything else you do there.
But even before that, you said that you’re a curator and that you’re really comfortable stating that it almost felt like you have evolved and you started to introspect on the things that are important to you and the things that you feel good about.
And the reason why I bring this up is because I also have, over the years, evolved in figuring out like, what is my… not, not brand, but what is like my definition?
Like what do people… what do I want people to know me as?
And for me, it’s always been a builder. I always love building things. I love seeing things come to life.
And that’s kind of why I started the company because I wanted… I had this idea and I can’t just let the idea sit in my head. I had to build it out.
And my kids know this. During the pandemic, I was deep into woodworking and I would build them mud kitchens, the Pickler Triangle, like a bunch of stuff.
I’ve made a lot of like handmade toys and they’re like really well-crafted toys, like extremely well. Like I probably over-engineered, but I’ve always…

Kim: Yeah, yeah, yeah.

Gil: But I always found myself as a builder.
And I just… when you said that you feel really comfortable stating that you’re a curator, that brought me a lot of joy because I felt like… I feel like a lot of folks nowadays, well, not nowadays, but many folks, they’re still discovering themselves and they’re still trying to figure out like, what do I want to be known for?

Kim: Mm-hmm.

Gil: And when you…

Kim: It is.

Gil: But when you do find that, it’s very, very invigorating because then you start to really understand what are the things that bring you a lot of joy, and the projects that you really want to dive into.
And you mentioned also like the projects that you may not want to do or you might want to delegate as well too.
I don’t know if you… also being a transformational coach… like, if you have any resources for folks that really are trying to seek their identity in this space around that.

Kim: Absolutely. I have a lot of information around that and would be happy to talk to anyone about it.
I will also be starting in the fall—I will be offering courses. They’re called “Clarity Catalyst Journey.”
It’s an eight-week course and a “Creative Action Journey,” which is for those that… the first one is really to identify, to bring clarity into what it is you want to focus on.
And then the “Creative Action” is… I know what I want to do, I know what I want to build, now I need like to get all this stuff out of my way so I can.

Kim: It’s so interesting. Last year I went to this… I went to a women’s retreat in Sedona and had this incredible experience.
And I went there with this concept that I had to choose between these two parts of me.
And I was feeling the pull, like really about this transformational coaching.
And I also like… you know, you get to a certain point in your life and I feel like legacy is coming up a lot.
And what I want to show my daughters—I have two daughters, beautiful young women—and legacy keeps coming up.
And I just went there with this kind of… I have this burning question, like, do I go to this other… you know, is there a crossroad?
Do I take left? Do I go right?
And the message was so loud and clear. I mean, this is like through Sound Bowl healing and great meditations and incredible moments.
The resounding, “You don’t have to choose, you are who you are. You’re both,” was very clear.

Kim: And so I have been really spending time with that… with those thoughts.
And so I have, I do have a… I have a lot of tools. One that I’ll share that’s really, really simple…
You know, you talk about a lot of times like how long a task takes, the opportunity, right, of a task.
And there’s plenty of places… I know we use them a lot of times when we’re looking at systems.
And you say to yourself, “Okay, I love doing podcasts,” right?
So I get really great… what? I get great energy from it. I’m really excited about it, and I do it with ease.
I feel really comfortable talking to you, Gil, like I’m fine.
Now, get me on a Facebook Live and I will run to the other side of the room. Like I… there’s… I don’t know why.
I am working on it, but it’s getting to know yourself about what brings you… what do you… what do you operate with ease?
What is… where’s your energy and how excited are you?

Kim: Because if you’re not and you see a list of tasks on your to-do and a number of them are decreasing your energy, weighing you down, getting put off to the next day, the next day, the next day… it’s not for you.
And that’s okay. There’s really someone that can handle it.
It’s letting go, right? It’s letting go of recognizing what is my essence?
Where am I in my… I guess some people would say in my flow, zone of genius… I mean, all types of…
But I look at it as like, where am I the most creative? When am I the most me?
And that’s what I continue to find that I am doing.
I’m getting rid of the things that are less me and not getting rid of understanding the implications, but understanding that I don’t have to do it.
And I think that’s a really… I think that’s critical for anyone in any industry, in any part of their life can use this filter.
And I think you’d be surprised how many things you’re like, “Well, no kidding, I don’t like that. This makes me feel like…” whatever, you know?

Gil: It’s interesting that you had mentioned that you at one point struggled to find, not your identity, but like which area of your life that you want to hold true to and later coming to realize that it’s actually both parts that you wanted to hold onto.
And I think that I constantly think about the dynamics of our industry and short-term rentals and how we just have some amazing people that enter the industry not knowing that they’re becoming entrepreneurs themselves.
And it’s a double-edged sword where you come into it not knowing, “Oh, I don’t know marketing,” or “I don’t know operations,” and you’re learning these new skill sets that one, you didn’t expect to learn nor maybe you wanted to learn, but it kind of forces you to do so.
But as you scale, you start to lean on, “Okay, maybe I don’t have to do everything all now anymore.”
We’ve grown our portfolio, and now I can start to delegate things to other people that may enjoy it more than I can.

Gil: But also, like, as I think about your two worlds where you are really, really professionalizing short-term rentals and really how to operate them really well, but also your mindset coaching side of things as well.
And I can see that being very applicable because what I’ve seen in the industry is that we have… and you probably notice this quite a bit… where you have a lot of influencers or just people that are just trying different things out in the industry.
They started off as hosts and they just found this one problem and they just can’t get rid of it.
That’s happened to me. Like I went into this industry with my tech background. I was a host and those are two separate worlds, and I ended up starting a company around really serving direct bookings and that entrepreneurship there.

Gil: And I’m not the only one in the industry that has done something like this.
I’ve seen this over and over again where it’s almost like hosting is a launchpad into another endeavor that you want to go down.
And I can see your coaching business also really opening up people’s eyes and figuring out, “Okay, you’re doing this right now. You could scale your portfolio, but you could also apply your skills in many different areas that really bring you a lot of joy.”

Kim: I think it’s critical.
And we hear it a lot. I mean, I know there was definitely a race to the finish at some point where people are like, “I need 50 doors. I need a hundred doors.”
It’s like, whoa, wait.
Saying yes to every door and also every owner… I mean, I don’t know about you, but how much you’ve worked with other owners.
It’s… it’s difficult.
You’re basically signing up to a lot of people’s opinions and don’t feel so much that you’re running your own business at times.
And so I think there’s a certain aspect too of some realistic, um, aspects that happen as we scale if we’re not really kind of clear on what we want.

Kim: Like, what is it? Like, what is the… at the end of the day?
Because some people do want that.
Some people want to scale and have this powerhouse property management company that slays—and all power to ’em.
Whereas I’m like, okay, like I have these incredibly profitable investments that are doing so well, and I definitely want to continue to pivot into anything that makes more sense, right?
Like, I’m not gonna take on, at this point, a three-bedroom house in Coachella Valley.
That just is… there’s too many, right?
Like, I can’t promise the owner good returns.
I can’t probably make any money myself in the way that I want to do it.

Kim: And I think that’s what’s the critical piece. I want to host the people here in the estates, right?
I want to have that experience for people because they’re not getting it elsewhere all of the time.
They are getting it, but not as frequently.
And so I think that that’s… that comes from who I am.
And so I… I do feel that just having, you know, been around obviously hospitable hosts and reading all three volumes and obviously our amazing supportive community that really are looking to elevate the standards and educate everyone that, you know, that is interested.
Like, this is… how can I be better at this?
How can I not stress out every time there’s a toilet that clogs?
I mean, when you have 10 toilets in, like, you know, one house, it’s a little nerve-wracking.
It happens regularly.

Kim: So how do you handle… how are you composed? How do you handle it like a pro?
And I think also getting to know your communication style.
What triggers you?
I mean, there’s so much psychology in what we’re doing because it is an experience.
It’s not like when you… I mean, it’s an experience too when you buy something.
If I buy a piece of jewelry and I look at it every day and it’s an experience, I’m happy I bought it. It makes me happy.
But this is like with people.
And the experience, or the… at least when my, you know, I don’t really cater to the solo traveler, so this won’t make sense for those that do.
But I am constantly hearing about these beautiful occasions and those incredible memories that were made.
And to me, I’m like, “I… we did that.”
You know, our team, we… we all did this together and that family has this memory.
You know, numbers of times people come in internationally to come to the States and visit with their family from LA and they’ll all come out here.
And all of a sudden it’s like just this incredible, you know, probably never to happen again, stay.

Kim: So it’s… I think it’s really important to understand why you get into this business.
And especially if you’re really looking to fine-tune the hospitality piece, really understanding that we are in hospitality and it’s the wild, wild west in a lot of places.
And you know, I think that’s changed.
I think more and more people expect, you know, a more professional product, professional service from beginning to end.
But it’s also really fun.
And I think that’s something we can’t forget—that people are mostly coming to have fun.
And so I think to give them the ability… and as we said, you know, “Taking leisure seriously so you don’t have to,” as a tagline is really our essence.

Gil: Yeah, yeah, yeah. You mentioned a little while back that there’s actually a lot of folks that, because you’re delivering such a great experience, they do tend to come back.
And you also mentioned on the other side, like, these are one-time, one-lifetime experiences where the families don’t get together.
I’m interested in hearing from you and maybe kind of like pivoting to the second leg of our show for a bit.
It was really around, like, how do you transfer that person that had a great stay with you one time to being someone that really wants to find this place as an annual stay or a biannual stay?

Kim: So we do nurture our guests.
One of the… you know, back to fun. One of the things we do is, as you know, when the booker… I think a day after they check out, we send them this video.
It’s them being presented a trophy and there’s confetti and it says, “You’re officially a Purveyor of Leisure.”
And they have a certificate they could print out.
And it’s just this fun way of saying like, “You did it.”
And like I said, because of all the work and, you know, that they put into making this day so special for their group, they deserve a little extra special.

Kim: So what I find is, you know, we definitely have great open rates.
I will say we’re still fine-tuning kind of the rebooking part because it is hard to say, “When’s the next time I’m gonna travel with 16 people?”
I mean, you’re not gonna rent our… our houses… our smallest one is six bedrooms.
Like, so that’s like 12, 14 people.
You’re… it’s… think about how many times you have, right?
Maybe once a year.
And so, and then the question becomes, maybe they wanna try another area, another region.

Kim: But what we are finding, because we’ve been in the business now for 10 years, is people coming back a second or third time.
I mean, we have some people that come back every year at Thanksgiving and it’s their house.
It’s like what I was saying, I pass the baton.
They become the host. It’s their house.
We are starting to see people… “I stayed there four years ago. I stayed there three years ago. Five years ago.”
Like this concept of coming back.
We do nurture them.
We give them all sorts of opportunities to book with us directly.
And, you know, we give them promotional codes.
They do also receive a loyalty discount—10% on any stay in the future. No other restrictions.
So that’s the… that’s the loyalty discount.
They get a 20% discount if they book within six months.
So that’s like our first part of our, I’d say, nurture sequence.
And then we just highlight, you know, things that are going on when we have a new property or like the hotel was a big launch.

Kim: Actually, one of our buyouts came from a Purveyor of Leisure, a guest… just a guest that was… and we had received her email through StayFi.
So we were able to market to the Purveyor’s contacts because of StayFi.
And this woman was not the booker, she was a guest, so she logged in.
And that… StayFi has ultimately exponentially increased our contacts because when you have 16 people staying and they’re all logging in… or the majority are… all of a sudden, we don’t just have that one or maybe a second email of someone else helping organize.
Now we have, you know, typically around 10 emails.
So that’s been incredible to be able to be in front of that many more people.

Kim: And, uh, yeah, we just try to stay… I mean, it’s basically a nurturing strategy, but one that I think… I think we can get better at it.
We’re looking into that right now, like how to really fine-tune the ones that are going past the opens, the clicks, and really kind of what else we could offer.
What can we do to get them over the edge? Like obviously they were interested, like, what can we, you know, how can we sweeten the deal so that they would come back sooner?

Gil: Yeah, yeah.
I’m… I’m betting that you’re consistently looking at the actual metrics behind each one of those sends and figuring out which ones are the messages that get people hooked.
If you were to change this message to come earlier on in the cycle…

Gil: What we found is like a lot of folks that are like… and for us, our booking windows are usually like two months out.
So come month nine, that’s when we start to hit them with the coupon code to come back again.
Because that’s when they’re starting to think about their next trip.
So, like, we found that a lot of times we will really spend most of our energy from a nurture standpoint really like giving value back to the guest and really just staying on top of mind.
And I think for you, a lot of the content could be really around like really how do you organize these stays?
And maybe having them reminisce on all the great things that they’ve done in the area, but it’s really around like the value of them and really focusing the spotlight on them.
And then come month nine when the booking window is just around the corner, that’s when we start to sell them.
And I think that that has done really…

Kim: We may reverse it based on what you’re saying because our booking window is two to three months.
I mean, we kind of bring it back up, but I think maybe we’ll just reverse it.
People are just not ready. I mean, this is the thing, the guest may be ready, so it could be the guest journey that’s a little bit different.
Because, you know, one thing we also learned is that the people that come to the house, for the most part in this group of 16, don’t necessarily even know where they’re going.
Right? Like, you get an address, your friend tells you, “This is where we’re going.”
And I like nurturing also those guests differently than the person who booked because those guests don’t know anything about Purveyors of Leisure.
They don’t know that we have all these other properties.
They don’t know about… you know? Whereas the other guest most likely has a little bit more, more information.

Gil: That’s actually very sophisticated. I haven’t heard of a host that actually segments their list within even StayFi or somewhere else.
That’s actually very smart because a lot of times here at least… you’re not organizing large groups.
So the persona is actually not that different.
You’re not a host. You’re not taking on that persona.
But I think you’re absolutely right.
For you specifically, that persona of the person that’s actually doing the booking is different than the one that’s just staying at the booking.
Because they’re… they’re almost… they’re almost working while they’re having that trip.
They’re making sure that everybody is satisfied.
So it makes a ton of sense that you actually have different sequences based on just people staying… like the different types of people that are staying with you.

Kim: And actually, I think we’re gonna… I think we’re gonna switch over to using… we’ve been using M-M-S-T-R, I think we’re gonna switch over to using, as far as the email marketing campaigns.
We may not switch over. We may just do both and some use both.
But StayFi seems… I just was on a great webinar with, um… oh, his name is escaping me right now… Arthur?
Yeah, and he… he was explaining… I mean, their open rates and click rates… it’s like insane. So powerful.
So I’m… yeah. Yeah. So I… we’re, you know, this is the thing. It’s like we’re just constantly evolving.
We’re looking at whether it’s metrics, we’re just looking at like, what are people up to?
I mean, we got to the point where like, we were top banana for so long and to a certain degree, I wouldn’t say rest on our laurels, but I guess on certain… on some… on some of the properties that were our big champions.
And all of a sudden, you know, you get onto… you start doing your comp set and you realize, “Oh… oh… oh, okay. There’s a few more, there’s a few more eight bedrooms.
Oh wait, there’s a nine-bedroom. Oh, there’s a ten-bedroom.”
And our comp set went from, I think it was like something like 16 to 36 in the last three years.

Kim: And so obviously that’s gonna eat into your avatar group, right?
And I think the main thing with that was pivoting and saying, “Okay, what… we already have these beautiful properties.
We have a lot… a lot of things that we had that people… Jen… was space.”
We have… everything’s on like one to two acres, which is pretty large for the area.
And so we were able to add pickleball courts and all these other amenities and… and how it’s flying off the shelf.
So it’s… it’s amazing to… but that’s the reality, right?
You have to keep looking at your numbers, you keep tweaking, you keep… and then you decide.

Kim: And I think for the most part, you know, we’re… I’d say for the energy invested and the time operating, we are probably… if there’s a, you know, some sort of… some sort of value you can place on it…
We are the most profitable we’ve been because of those… all those other parts.
If that makes sense.

Gil: Yeah, yeah. I… I think the interesting part is you… you make a very good point of like…
It’s actually not just feeling like you have all these things set in stone and that your booking engine is working as it should.
It’s almost like you’re constantly thinking about tweaking that over time.
And you also mentioned really the energy that you’re putting in there.
It’s almost like every so often you step away to focus on another side of the business, and then when you get to zoom back into it, you start to realize like,
“Oh, actually I did this this way when I had this much information. Now that we’ve tried it out, I have much more information.
I know what people are opening. I know what messages are actually going through.”
You start to evaluate like, “Okay, could I be doing something different? Can I be…”

Gil: And there’s… the nice thing about us is like our industry is like… it’s constantly evolving.
And I think like if you continue to tune and continue to iterate, you’re gonna… you start to reap that benefit in the long run.

Kim: Absolutely.
I mean, when I think about where we started and like… I mean, I… I got to a point… I think I mentioned, uh, my business partner would say,
“Okay, anti-customer service,” about me because I was burnt out.
You know, I mean, I was answer… I… when you start to think…
This is the other thing, it’s… it’s mindset, right?
“I have to do it. I have to do it because I’m best at it. I have to do it because I communicate differently than other people. I have to do it, X, Y, Z,” input whatever.
That’s not true.
You need to figure out how to communicate clearly what it is that you want and be able to train people that care on what you want.
And then you measure it and tweak it and measure it and tweak it.
And then if it’s not the right fit for a person to do it, then it’s not.
If the system doesn’t work, it’s too cumbersome, get rid of it.

Kim: Like we’ve ramped up, we’ve ramped down.
I mean, there’s so many aspects of evolving and… and… and… and let’s face it, I mean, our industry because of its…
I mean, I’m sure we probably could look at some statistics.
I mean, it’s just growth… the growth is exponential.
And because of that, tech followed right in trying to service all of our needs.
And I mean, I think when we first started, there was like some, you know, snapshot of how many PMs versus…
you know, these incredible, uh, snapshots in time about the industry and obviously the intersection with tech.

Kim: And you know, and I’m… I’m curious, uh, just because I mean, I… so I’m… I’m taking an AI consulting certification class.
I’m very interested. I love tech, but I also…
I’m curious about your take because you’re techy about AI in our industry.
Like how do you see… do you see the advantages? Do you see the disadvantages?
If you don’t mind me asking… I’m not… now, now I’m interviewing you, Gil.

Gil: Yeah, no, no, no. It’s… I’m just curious.
So I… no, I think that there’s a… I have like mixed… not mixed feelings. I think generally, I… I actually am a big proponent of AI.
And I actually… in our team, I encourage folks to really use AI as a tool to help them do their job better.
Obviously, you can do things faster with AI, but can you do things better or can you do things that you couldn’t have done before?
Those are the skills and those are the things that I’m really interested in as a leader there.

Gil: So I’ll give you an example.
I’ve been in tech for the last 15 years, uh, I’ve been a product manager and every two or three years I’ll relearn to code because I’ll pick up a project that I really want to do.
I’m a builder, and I’ll code something.
And I have to relearn everything because I… it’s a skill set I’m not really paying too much attention to on a regular basis.
But I had this idea of creating some sort of app and I was using AI to help me just really think through.
And it’s because I come from a product management background.
I know how to build products, I know how to envision them, I know how the tech stack works.
But now I’m using AI to really identify where my blind spots are in my architecture as I’m thinking about it, what features should I be thinking about?
And so it’s really exposing really the blind spots in it.

Gil: And then… yeah, it’s really neat.
And I’ve learned new technologies as part of it.
And then what I’ll do is it tells me you should consider these things.
And I found out that there’s a technology that I didn’t understand, so I had it explained to me in the same chat window.
So I’m just using it to just learn about it, and then I then regurgitate back what I understood of it.
And then it helps me validate, am I doing it right? Am I actually learning? Am I actually improving?

Gil: And just coming out of that project, it was very invigorating because I felt like this was actually one of the few times that I’ve interacted with AI,
where I didn’t feel like AI was an agent to me, but it felt like more of a collaborator with me.
And I ended up actually using a different AI agent to help me code.
And I started the project at seven o’clock at night, and by four-thirty the following morning…
Monday morning, four-thirty… I stayed up super late. I had a working version of my app that I had deployed, and that was just insane… mind-blown… insane.

Kim: It’s so cool.

Gil: It was insane.
It’s… it’s just so cool. And like I… I think even a… a skilled engineer would have taken much longer than that,
but just being able to distill that information down and having it translate…
It was not like I just brain dumped and said, “Hey, create me this app that does this.”
I had to actually go down and create each individual building block.
How do I want things oriented and like really crystallize my vision?

Gil: So I think like from… from a creator standpoint, I see AI as being a really good tool to help you translate what’s in your head and bring it to life.
And that’s what I’m really excited about in AI.
On the more tactical front of it, specifically in our industry, the best use case… actually the two best use cases that I’ve seen AI used is one is really around revenue management.
Because you have this large set of data and you’re trying to figure out how do I optimize my listing price based on that?
And we’ve seen almost all the pricing automation tools or pricing optimization tools really leverage AI.
And they’re kind of like the forefront of it all. Like you… you got PriceLabs, you got Wheelhouse… you got all these AI… you have all these sets,
and that’s actually a problem that’s ripe for AI to help you solve.

Gil: And, uh, the other one that I’m really interested in is really AI being used for guest messaging.
I was completely against this in the very beginning and it just felt so inauthentic. It felt like I was like cheating.
And I started to play around with it.
I put it into a mode where it’s not on answering on my behalf, but it’s actually generating the response for me.
And it’s looking at my past history and my tone and the information that I’m giving it, and it’s helping me answer guest questions better than I have.
And it wasn’t until more recently that I started to put it more on autopilot where it’s responding on my behalf if I don’t interject within five to ten minutes.

Kim: Right.

Gil: So you give yourself a chance to look at it if you want to.

Kim: Yeah.

Gil: Yeah, yeah, yeah.
And actually, that has worked out really, really well and I’m just… it actually has up-leveled my ability to get to every guest and actually also be able to step away from the business for a little bit
without having to feel like I’m compromising the guest experience there.
And… and so far it has… it has done quite well.
I… and I… I don’t recall a lot of issues. Like, darn, I wish this thing didn’t do that well… actually once or twice.
But like, it’s… but that would happen with humans, right?
Like with us communicating, “Oh, I made a mistake. That’s not that property. Like it’s over here,” or something. Whatever.

Gil: I mean… but like, like if someone’s asking me, “Oh, what’s the nightly rate for this? We’re looking to extend our stay. What’s the nightly rate?”
What I would typically have to do is go into OwnerRez or PriceLabs and figure out what my nightly rate is,
and then figure out like what the taxes are, and then go back in and then respond to it.
In this case, AI is actually able to draw all that information and then actually package it up,
and they’re able to answer that and generate a response even faster than I can even do the research on it.
So it’s… it’s just amazing.

Gil: So like, um, I am not a huge fan of just like going from like giving a prompt and just throwing whatever that… that output is into some marketing copy or whatever.
Like that to me feels like you’re not even putting the effort into it.
It’s almost like you’re treating AI as an intern.
I… that is not how I envision AI really excelling.
And some people are using it that way, but I’m also starting to see a shift that people really using AI to really professionalize what they have already done really well in.

Kim: I agree. And I feel like it does the heavy lifting.
It’s a collaborative relationship.
And I think that’s kind of what you were saying with the coding, you know, like that you… and I love that piece about using what you…
understanding what you learned and asking if you got it right.
Like, I’ve been doing that, I’ve… I’ve been taking my transcripts actually from my podcasts and putting them…
and I have like a rubric that… these are the… these are the points I want to make.
Am I doing a good job? Am I getting better at it? Am I clear?
You know, I have a certain number of variables and it’s great.
It really points out like the overall sentiment, how it was going.
Do we speak too… you know, I ask if I’m talking too much about one thing versus another.
Like really trying to get better at interviewing.

Kim: Yeah.
It’s fascinating to have it check you, not necessarily just be this output of… of ideas or whatever, you know.

Gil: That I think that… that is actually like what it is, is like really like not using AI as the output generation thing,
but using it as a copilot for you to kind of manage all the things that you have to do in life.
And I think the stronger that you can understand what you’re trying to do, what you’re trying… what the outcome is, the better that you can use AI.

Kim: And isn’t that true of everything in life?

Gil: That’s true.

Kim: That is true.
I kept saying, I’m like, all it’s doing is helping us get very clear on our communication so that we can understand exactly what it is that we are after.
You know, they joke… they… there’s a saying in coaching like, “Unspoken expectations are… what is it?
Unspoken expectations are premeditated resentment.”
So it’s… to me, AI has become this coach for me on my clarity when I’m working on something.
Because I see that… I… I understand why they… they went that direction.
I’m not clear. Right. And I fine-tune it and then like, “Remove this, do the…”
Not just with… not like an image, but in coming up with copy for emails or whatever it is that I’m… you know, launching some of the things I’m doing.
And so I’ve just… it’s… it hit me like, wait a minute, this is fine-tuning our communication with ourselves.
That’s called clarity.

Gil: Yeah. Ironically, that’s actually what I was working on.
The project that I was working on was… I was creating an AI assistant because as an entrepreneur I felt like I was juggling a whole bunch of different things, a bunch of different tasks.
And I was trying to figure out, is there a way that I can have an AI assistant understand my life much more intently?
And for me to provide a context on what’s important to me, what are my goals for the year, what’s my goals in life in general?
And use that as a filter or a barometer or a weighting system or some sort of way to help me make sure that I’m living a much more intentional life.

Kim: I love it.

Gil: And I was so surprised that I was able to stitch together the first versions of it.
Actually now, um, I’ve figured out like how I’m storing my data and how I can be doing it better.
So I’m actually reiterating that based on some of the feedback that I’ve observed myself, but also some of the early people that I’ve started to share this with.
But it’s just amazing, like what you can do and the things that you can solve.
I see AI as like really like helping us tap into a part of the brain that we just didn’t have the ability to do before.

Kim: I mean, we created it.

Gil: Yeah.

Kim: And so I feel like it’s… yeah, now… now it’s, you know, learning how to… how to work with that area that’s been exposed.

Gil: Yeah.

Kim: Yeah. It’s exciting for sure.
I… I am in constant awe of it.
And I think… and I think also what it does too is…
The clear communication and, you know, having this clarity when we’re looking for any output, like whatever the outcome is of a conversation, of a meeting, of… of whatever it is that you’re doing.
I think it also… the work, you start to think through workflows because that’s how you have to communicate with it, right?
So you’re prompting… your prompt engineering is really spelling out or getting really, really, really detailed on that workflow.

Kim: And I think so many of us are operating on automatic workflows.
And so to really start to break it, right? Like it’s like throw it down on the ground, watch it break apart so that you can rebuild it.
I think that’ll be the interesting piece—like how we will continuously refine both our workflows within our work,
but our workflows within ourselves, like how we process the information.
And like you said, I think it’s amazing to be able to think about it from an intentional standpoint.
I think of Ikigai when I think about what you’re talking about.
It’s like this framework, right, of like all this balance in your life.
And you know, everywhere you go, there you are.
John Kabat-Zinn is a meditation teacher, mindfulness teacher. His saying…
and it’s true because to say that Gil is not the dad working and starting and owning Crafted Stays…
like that, it’s… how do you take those two people apart, you know?
I mean, you’re the same person.

Kim: And I think that for a long time, probably culturally, we have really honored and praised Gil the Crafted Stays guy.
And maybe the dad piece, which has a lot of depth and lots of color and lots of…
you know, I mean, building craft toys, right? Like, has this…
you’re not, you know, the one person, you know, the same person.
And so I think it’s just a really… I think I look at it as like,
this is potentially a celebration of really becoming more whole as a person because you will have some of this heavy lifting.
I mean, so many people have so many intentions, and at the same time, you know, we’re human.

Kim: But maybe we’ll have some help.

Gil: Yeah.
It’s… it’s… it’s gonna evolve over time.
I’m excited about it. We’ll talk about that on the next podcast.

Kim: Yeah, absolutely.

Gil: Awesome.
Kim, we usually end the show with three questions.
First is a book recommendation.
Any good books that you… you would recommend to me?

Kim: I’ll probably just go with my favorite: Dr. Michael Ray, Creativity and Business.
It’s… it’s the reason… so the course that I am trained in teaching at Stanford from Stanford is…
he was a professor for many years, uh, since retired at Stanford and in the MBA program.
And what he found were lots and lots of incredibly brilliant people with zero understanding of what they wanted out of life.
And so what he did was he drew upon some different philosophies and was able to weave together this book about creativity
and then therefore a course that’s still taught there today.
And I just find it’s… it’s really a great read.
It really helps you see, like, it doesn’t matter really how smart you are,
but if you don’t know what direction you’re going and why you’re doing it…
like, you can have all the intentions in the world,
but if you don’t attach meaning to it and an emotion to it, what are you going to feel like when you get there?
You’re just gonna pick another one and another one. Right?
So I feel like that… that… that’s an incredible… an incredible…

Kim: I could go on. I mean, I have so many books: Buddha and the Brain, Radical Acceptance…
I mean, I’ve been… I’ve been interested in psychology, neuroscience, and I’d say spiritual psychologies for 30 years.
So I have a lot of, um, great book options.

Gil: Yeah.
As you… as you’re mentioning that, it reminds me of, uh, a documentary that I’m…
I just started a… like a Netflix short series around Bill Gates. I don’t know if you’ve… if you’ve watched it.

Kim: Oh, yeah.

Gil: Um, but what I find interesting is that you have Bill Gates, one of the most successful entrepreneurs, tech mogul of actually our… like our generation.
Um, and he decides to leave Microsoft one day and just chase after philanthropy.
And it’s just… it’s very humbling to know that it’s not just about grind, grind, grind, build, build, build towards in some sort of massive, um…
like wealth building, but he’s now actually pivoted that towards like… he’s actually depleting the wealth that he has or reusing the wealth that he has
to actually chase a bigger dream that he has for himself. Right? Possible serving, right?
And I just find that just very, very inspiring that someone that has so much fortune is actually trying to figure out,
“Okay, how do I use this fortune in the best and most meaningful way to him?”

Kim: Right.

Gil: Possible serving.

Kim: Right.

Gil: So yeah, that… that… that reminded me much like as you’re explaining what the book was about,
it reminded me specifically of him.

Kim: You’ll love it.
It’s… you know, it’s a little bit not dated, but it’s a little older now.
It won’t have as many obviously, uh, anecdotes from now, but it’s definitely… it’s relevant.

Gil: Nice.
Second question. What’s, uh… and this is probably a very, uh…
good question for you.
What’s one piece of mindset advice that you would give to someone that’s starting something completely new?

Kim: I think the key is to know that there’s gonna be a combination of making it happen and letting it happen.
I think we get so caught up on like, “Okay, these are my action steps to have this outcome.”
And then, you know, step three winds up train-wrecking, and you’re like, “Oh, okay. I need a new step three.”
And I think so much of like when we… and this is true of in life,
we are so attached to an outcome that we don’t allow for kind of… you know, we’re just gonna… it’s more painful I guess, is the thing.
And I think that if we recognize that… well, one, I mean, any new endeavor is gonna be new to you and there’s gonna be a lot of evolving that happens throughout that,
uh, you know, from beginning to end.
But I do think it’s really a fine dance between making it happen and letting it happen.

Gil: That’s awesome. Awesome.
Last question.
What’s one piece of tactical advice that you would give to someone that’s getting started in direct bookings or looking to amplify the direct bookings?

Kim: Really get clear on your brand.
And the avatar you want to serve.
I think that goes to say, like, even whether you are a property manager looking to take on more owners,
and it may have happened haphazardly.
Like you have this property here, and then your friend’s aunt said, “Hey, maybe you could manage my property.”
And then you find something—create a theme, create some sort of brand that you can buy into because you’re selling it.
No matter how you look at it, you are selling it as a STR manager and operator and/or marketer, which we know we all are—wear all those hats.
So I think it’s important to have something that you can sink your teeth into that feels good to you.

Gil: I like that. I like that.
Kim, where can folks find out more about you? How can they keep up with you? How can they interact with you?

Kim: Well, I am… it’s probably best to go to my Linktree, Purveyors of Leisure.
Uh, that’s where kind of you can learn about all the different things that I’m up to.

Gil: Awesome. Alright.
I’ll make sure to drop the… the link in the show notes if you will.
‘Cause I mean, had I really thought about it, I would’ve not chosen Purveyors of Leisure because you know how many times I’ve had to spell it.

Kim: (laughs) Right.

Gil: It is a fun name and it really… I’ll tell a quick, quick story.
It came from my husband and my business partner were the Gentleman of Leisure when I first met them 20 plus years ago.
And they had a sign, they were roommates and they had this sign. It was, you know, the “Gentleman of Leisure.”
And I was like, now I’m hanging out with them. I’m like, “Hey guys, like what… you know, what about me?”
And so years roll on and then I get into business with John and now we’re trying to come up with a name,
and my husband’s like, “Well, I mean we had the Gentleman of Leisure, but like, you guys are like offering leisure to people.”
And that’s how it came—Purveyors of Leisure.
So anyway…

Gil: Yeah, exactly.
It’s been a pleasure.
Thank you so much for having me, and I look forward to seeing you.

Kim: Yeah, I look forward to it too.
Well, I have seen you by this time the show ends or by the show airs.

Gil: Yeah, we will.
We will have seen each other.

Kim: Yes. In person, in real life.

Gil: Yeah.
Awesome. Kim, it was great to have you on the show.

Kim: Bye.

Gil: Bye.