Technology Enables Hospitality: Building Direct Booking Success Without Losing the Human Touch with Jessica Gillingham

Summary and Highlights

👤 Meet Jessica

Jessica Gillingham is the CEO of Abode Worldwide, a strategic public relations agency specializing in elevating the profile of transformative technology solutions across the global hospitality, lodging, and living sectors. Abode sits at the heart of the developing intersection between work, life, and play in real estate and hospitality, partnering with brands playing a lead role in this transformation. A regular industry speaker, author, and adviser, Jessica is also the host of the Pillow Talk Sessions podcast and author of “Tech-Enabled Hospitality” (Kogan Page, August 2024). Drawing on interviews with over 30 industry leaders, her book examines how technology is transforming every aspect of hospitality operations and the guest experience. She’s also the creator of the Abode Worldwide Short-Term Rental Index, now in its third edition, which catalogs over 200 tech companies and trends shaping the STR industry.

🎯 Why This Episode Matters

Most property managers are sitting on goldmines of untapped potential. Jessica reveals a startling reality: operators typically use only 30-40% of their existing technology’s capabilities. This isn’t just about underutilization—it’s about missing the fundamental shift happening in hospitality. While other industries, such as e-commerce, have seamlessly integrated digital experiences into every touchpoint, vacation rentals remain “clunky” and fragmented.

This episode cuts through the noise of endless tech solutions to address the real question: How do you leverage technology without sacrificing the warmth and personalization that defines true hospitality? Jessica’s perspective, informed by years working with both hotel and vacation rental technology companies, offers a rare bird’s-eye view of where the industry is heading and what operators need to do now to stay competitive.

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💡 The Mindset Shift: Investment vs. Cost

One of the most powerful insights Jessica shares is the divide she observed while researching her book: successful operators view their tech stack as an investment that enhances their business, while struggling operators view it as a necessary expense.

This mindset difference determines everything—from which tools you adopt to how you implement them. Operators who treat technology as an investment actively seek to understand its full capabilities, integrate systems to create seamless experiences, and continuously optimize their digital guest journey. Those who see it as a cost often implement the bare minimum, leaving powerful features dormant.

The gap isn’t just philosophical. As Jessica points out, guests now expect the same frictionless digital experiences they get from booking doctor appointments, ordering food, or shopping online. Everything in our lives has been digitalized—except, often, the hospitality booking journey. <a href=”https://craftedstays.co/blog/”>Property managers who fail to bridge this gap</a> risk being left behind as the industry consolidates and guest expectations continue rising.

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🔍 The Education Gap: Why Hosts Aren’t Using Their Tools

Jessica identifies a critical problem plaguing the industry: operators often lack awareness of their own knowledge gaps. Most hosts and property managers can’t identify where automation could help them because they haven’t clearly defined their operational gaps. Even more challenging, they don’t fully understand what their existing software can do.

This creates a vicious cycle. Without understanding your problems, you can’t evaluate solutions effectively. Without understanding your solutions, you can’t leverage them to solve problems. Jessica compares this to any software we use—”We’re on Riverside right now,” she tells Gil, “I bet you don’t use the whole caboodle of what Riverside can do for you.”

The solution? Strategic education. Before adding another tool to your stack, invest time in understanding what you already have. Map your operational pain points. Then systematically explore whether your current PMS, guest communication platform, or pricing tool already addresses those challenges. As Jessica emphasizes throughout the conversation, <a href=”https://craftedstays.co/blog/”>the most successful direct booking strategies</a> start with understanding your foundation before building upward.

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🏨 The Accidental Entrepreneur Problem

Jessica makes a crucial distinction that many hosts overlook: “Most hosts are accidental hosts. You don’t go to university thinking I’m going to be a professional property manager.” This creates unique challenges because running a short-term rental business requires three distinct skill sets that rarely come naturally together:

Hospitality expertise – Understanding guest needs, creating memorable experiences, and maintaining service standards

Business acumen – Managing finances, hiring teams, scaling operations, and strategic planning

Real estate knowledge – Property selection, market analysis, and investment strategy

Unlike long-term rentals or commercial real estate, which have established frameworks and educational pathways, vacation rental operators often stumble into the business without realizing they’ve started a 24/7 hospitality operation. As Jessica notes, “It’s always on. Property managers tend to be extremely hardworking, putting in a lot of hours into their businesses.”

The path forward involves recognizing these gaps and actively seeking education. Whether through podcasts like Booked Solid, industry conferences, or peer mastermind groups, successful operators treat learning as a core business function rather than an occasional activity.

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🤝 Technology + Hospitality: Not an Either/Or

Perhaps the most important theme Jessica emphasizes is captured in a single quote from Ryan Killeen, CEO of The Annex in Toronto: “The future of hospitality is hospitality.”

Despite all the discussions about AI, automation, and efficiency, the winners in this space will be those who use technology to enable hospitality, not replace it. “Hospitality doesn’t always have to be in person,” Jessica explains. “It can be delivered through digital methods. It’s just about understanding who’s on the receiving end and seeing your guests as individuals, not as a mass audience.”

This distinction matters enormously when evaluating which technologies to adopt. Tools that automate repetitive tasks—such as dynamic pricing, automated messaging for check-in instructions, or smart home controls—free up operators to focus on the moments that require human judgment, empathy, and creativity. The warm cup of tea that a guest didn’t know they needed. The personalized recommendation makes their trip memorable. The thoughtful follow-up that turns a one-time guest into a loyal repeat customer.

Gil shares his own experience with this balance, noting that <a href=”https://craftedstays.co/blog/”>guests who book direct</a> through his branded website develop stronger loyalty and generate more referrals than those who discover him through OTAs. Why? Because the direct booking journey allows him to control the entire experience, from first impression through post-stay follow-up, creating a cohesive brand relationship that platform bookings simply can’t replicate.

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📊 The Consolidation Wave and What It Means for You

Jessica predicts significant consolidation in the hospitality technology space over the next five years. “It’s not sustainable to keep running… There are so many, too many different tools out there,” she observes. Larger companies will acquire smaller ones, clear leaders will emerge in each category, and many point solutions will either disappear or get absorbed into platform offerings.

For operators, this consolidation presents both opportunity and risk. The opportunity: as platforms mature and integrate more deeply, the seamless data flow between systems that’s currently lacking will improve dramatically. The risk: betting on the wrong platform or tool could leave you stranded with legacy systems that no longer receive updates or support.

Jessica’s advice is to focus on established players with clear market leadership in their categories while remaining flexible enough to migrate if better options emerge. More importantly, ensure your <a href=”https://craftedstays.co/blog/”>direct booking infrastructure</a> isn’t dependent on any single vendor, so you maintain control over your guest relationships regardless of which backend tools you use.

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🎯 The Netflix Moment: Personalization at Scale

One of the most compelling opportunities Jessica identifies is bringing Netflix-style personalization to vacation rentals. “Amazon and Netflix are pretty good at being able to think about what we might want next,” she points out. “We look at our Netflix accounts and it’ll say, these are the documentaries you might be interested in next… We don’t even really do that in hospitality yet.”

The challenge? Unlike Netflix or Amazon, most individual operators lack the historical data and algorithmic sophistication to make personalized recommendations. Currently, only the large OTAs have enough user data—search history, booking patterns, travel preferences—to deliver this experience. They know which properties you’ve viewed, how many people you typically travel with, and what amenities matter most to you.

But as Gil notes, this gap is solvable. When your PMS talks to your CRM, which connects to your guest messaging platform, which integrates with your <a href=”https://craftedstays.co/blog/”>direct booking website</a>, suddenly that data ecosystem exists. You can see that a guest mentioned their anniversary in their first message and ensure every touchpoint acknowledges this. You can recognize repeat guests and automatically offer them their preferred unit or amenity upgrades.

The operators who build this connected infrastructure now will have a massive competitive advantage as AI tools become more sophisticated and accessible. Jessica sees this as the next major frontier: “That’s where it’ll get very interesting.”

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🔄 The Direct Booking Evolution: From Escape to Strategy

The conversation reveals a significant shift in how operators view direct bookings. Jessica explains that early direct booking messaging focused on avoidance: “Avoid OTA fees. Build your own site. No marketplace commissions.” This framing positioned direct bookings as an escape from Airbnb rather than a strategic business move.

The new approach emphasizes ownership and growth: “You’re not just hosting. You’re building a business.” This reframing is important because it alters how operators assess success. Instead of measuring success by what you’re avoiding (OTA commissions), you measure it by what you’re building (brand equity, guest loyalty, sustainable revenue).

Gil shares his experience seeing this firsthand: “The type of guests that I get from an OTA is a very different type of guests than those who have booked direct with me.” Direct bookers arrive already familiar with his brand, tend to become repeat guests more frequently, and generate more referrals. This isn’t just about saving commission—it’s about fundamentally different guest relationships.

Jessica reinforces this by acknowledging the OTAs’ positive contributions: “They’ve introduced vacation rental, short-term rentals to a much wider audience than ever before.” But she’s clear that as operators mature, having “all your eggs in somebody else’s basket” creates vulnerability. The relationship with your guest begins the moment they start researching their trip, not when they check in. <a href=”https://craftedstays.co/blog/”>Operators who control that entire journey</a> build loyalty that transcends any single platform.

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📚 Book Recommendation

The Power of Positive Thinking by Norman Vincent Peale

Jessica recommends this classic work on mindset, which she recently re-read. “It’s much deeper than the title makes it sound,” she explains. “It’s really about mind shifts.” For entrepreneurs and business leaders navigating the challenges of building a direct booking business, Jessica emphasizes that this book goes beyond simple optimism to explore fundamental shifts in how you approach problems, setbacks, and opportunities. It’s the kind of book you can dip into repeatedly, finding new insights each time.

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🎯 Rapid Fire Highlights

On resilience and starting something new:
“Failure is gonna happen, and resilience is really the name of the game. You are going to make mistakes and fail, and it will all go wrong for a period of time. But the important thing is to get up, dust yourself off, carry on, take risks, build resilience, and be consistent.”

On getting started with direct bookings:
“Educate yourself on what you need to do to get direct bookings. Think about the strategy you might want to put in place, what tools you might need, and how you would go about it. You can’t just wish for more direct bookings—it takes quite a lot of work, planning, and strategy to really get a very successful direct booking strategy within your business.”

On the service mindset:
“If you’ve got that hospitality mindset, you’ve got a service mindset. You’re always thinking about ensuring that the needs of those you’re serving are met. I think that is really hard to train—you kind of have to have it inherently in your culture, in your DNA.”

🔗 Connect with Jessica

• Book: Tech-Enabled Hospitality
• LinkedIn: Jessica Gillingham
• Company: Abode Worldwide
• Podcast: Pillow Talk Sessions
• Free Resource: Abode Worldwide Short-Term Rental Index 2026 (available at abodeworldwide.com)

🎧 Ready to Transform Your Approach to Technology?

This conversation with Jessica Gillingham challenges every assumption about how technology and hospitality interact in short-term rentals. Whether you’re just starting to explore direct bookings or a seasoned operator looking to elevate your tech stack, Jessica’s insights provide a framework for making informed decisions about where to invest your time, money, and energy.

Listen to the full episode to hear more about the specific tools Jessica recommends, her predictions for AI in hospitality, and the counterintuitive reasons why guest expectations in vacation rentals lag behind other industries.

Ready to build a direct booking website that converts? Visit CraftedStays.co to create a fast, mobile-optimized, SEO-friendly website that puts you in control of your guest relationships. Join hundreds of operators who’ve discovered that owning your digital presence isn’t just about avoiding commissions—it’s about building a sustainable, independent hospitality business.

Transcription

Jessica: That’s where hospitality doesn’t always have to be in person. You know, I believe quite strongly that hospitality can be delivered through digital methods. It’s just more about making sure you understand who’s on the receiving end of it, and, and seeing your guests as a, as an individual, not seeing them as a, you know, mass.

Jessica: Mass audience or whatever. It’s really understanding the individuals that might be staying with you.

Gil: Before we bring on my guest, I want to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on hearing the same. I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it. Here’s the thing, you’re letting all these marketing strategies, you’re driving traffic and you’re putting it all to work.

Gil: But if your site isn’t really built to convert, you’re basically lighting your energy and money on fire. And even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can’t iterate, you can’t test, and you really can improve on things.

Gil: You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I build craft estates. It’s purpose built for short term rentals and design from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings and you can keep on testing and improving as you learn, you can make changes all on the platform.

Gil: You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to Craft to stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing.

Gil: Hey folks. Welcome back to the book, solid Show, the podcast we’re bringing top operators to discuss marketing, revenue management, and direct bookings. On today’s show, I have Jessica Gillingham, she’s the founder and CEO of Abode Worldwide, which is a PR agency that helps companies and organizations find their positioning and marketing.

Gil: She’s helped many organizations in our space and is. Really, really well connected. She’s also a published author. She wrote a book recently published really around. Tech enabled hospitality. Uh, definitely check that one out. It’ll be in the show notes. She’s also really well connected and really has a deep ed understanding of how technology has changed over the last five to 10 years and some of the trends that she’s seeing now and really what some companies are doing really, really well, to really help bring hospitality.

Gil: To the forefront, leveraging technology. So I can’t wait to bring her onto the show and have her really just help us understand what’s happening behind the scenes at all these companies. Where are the investments happening? What are some of the experiences that are being built, and how do we as hosts and property managers take advantage of the shifting landscape there?

Gil: So, without further ado, let’s bring her in.

Gil: Hi, Jessica. Welcome to the show.

Jessica: Thank you Gil. Really good to be here and thank you very much for having me.

Gil: yeah. It’s really good to have you on. I saw you on LinkedIn because you had recently written a book that caught my interest. I, I do a lot of reading already, so, um, I’m always looking for new books and, but yours in particular. Kind of struck me because it had won my technology side, but also my short-term rental side.

Gil: My, maybe to kind of kick us off, do you mind giving yourself, uh, an introduction on who you are and what you do?

Jessica: Absolutely Gil, and I’ll start with the book. And the book is called Tech Enabled Hospitality, and it was published in the summer in in August, and it’s a. Book about hospitality and technology. So, so it’s really about giving us sort of an overview and I guess a guide to how technology is enabling hospitality across every function of operations and guest experience.

Jessica: And the book covers rentals, vacation rentals, but it also covers hotels. So it’s really looking at the, kind of the broad lodging hospitality, um. Spectrum and we look at everything in the book from. Property management software to marketing and personalization, to pricing, FinTech, sustainability, IOT, access all of it, as well as give guidance on the future of hospitality and technology and the book.

Jessica: In the book, I sort of interviewed over 30 leaders across technology and operations to get their kind of insights and their, their thoughts, basically around how technology has changed, how hospitality is now delivered and experienced.

Gil: So what led you down the path of wanting to, to write a book? That’s a big commitment for, for you to want to dedicate your time and energy into. Publishing a book. What was that, that gap or that itch that you, that you wanted to scratch?

Jessica: So firstly I was actually approached by the publishers. So the publishers are called Go Ga page and they’re business publishers and they wanted to basically sort of build a hospitality section of their, they, they do business books and they wanted to do hospitality books ’cause they felt there was a real gap, like there wasn’t many books about hospitality out there on the market.

Jessica: So they approached me and asked me if I would. Come up with an idea of what they felt was a book that I could write that that would also be of interest to, to the audience and to the market. And because of my work that, that I do, and, and alongside being a, a writer, I also run and own, uh, a public relations agency, a strategic communications agency.

Jessica: So I’ve, and we work for technology companies across hotels and short term rentals. So I’ve got a really kind of broad. Knowledge base, experience base of how technology has changed hospitality over the last, you know, few years. So, and I really felt that I wanted to kind of own that narrative around tech enabled hospitality.

Jessica: So rather than sort of seeing. The discrepancy. Like you either have, you know, you are either providing hospitality or you are tech enabled, but actually both, you know, really kind of, really sort of communicating that narrative around how technology is en enabling today hospitality. So it sort of started from that and.

Jessica: Of the research for the book and as I did all the interviews from it, it really kind of developed into this really kind of scope of how technology is changing the delivery of technology and how it’s being used in different ways and how the guests are experiencing, you know, experiencing hospitality as well.

Jessica: Now.

Gil: Yeah. So what’s, what’s one of the big premises of the, the book, we’re not spoiling too much because we, we definitely want our listeners to, to pick up a copy, but what would you say are some of the, the big premises or the big foundational pieces that you kind of wanted to build the book around?

Jessica: So what I wanted to build was really around a few things, but the, the main one really is around how the delivery. Of the offering of the hospitality offering is changing. So even though obviously it’s, it’s such a physical experience, you know, this is, this is an analog experience in, in the flesh. You go and stay in a place and you experience a place, but actually everything around it, from the customer experience, from search.

Jessica: To booking, to check in, even within the property to kind of post is all digitalized or, or, or potentially can be digitalized. So that’s one of them. So the fact that the delivery, even though it’s very much a physical product, is changing because of hospitality. The other area that I was very interested in looking at is that we, as consumers are so used to.

Jessica: Having digitalized experiences in everything we do. And you and I have been talking about, you know, before the recording about e-commerce and how, you know, all that kind of side of it. Like as consumers, everything that we do from. Booking the doctor pharmacy stuff, banking, train tickets, plane tickets.

Jessica: Everything is on our phone. You know, we are used to having very much digitalized journeys within hospitality. It’s still kind of clunky, you know, it’s still not as smooth and frictionless. As it is in other parts of our lives. So that was another area that I really wanted to explore. And then the final one was around the mindset.

Jessica: And it was really looking at technology as an enabler, as an investment in a business rather than as a cost. And that’s one of the, kind of the key takeaways is there is a real divide between operators that see. Tech, their tech stacks and technology as an investment, as something that improves their business, makes it better, makes it easier, improves that guest experience, whereas there are others that saw it as a needs must.

Jessica: You know, oh yeah, I’ve gotta have a PMS. It’s a cost rather than seeing as an investment.

Gil: Yeah, you mentioned something very interesting where, um, in one side we feel like hospitality is behind the world in comparison to other industries that have kind of kept up, if not pioneered certain advances, like we talked about e-commerce and how even nowadays it’s changing how social media platforms are.

Gil: Uh, marketing or delivering services. Now, um, my wife the other day, she mentioned like, oh, now Instagram has different types of ads specifically for e-commerce so that you can discover new products. And I feel like e-commerce is one of those that are kind of advanced or kind of further along in terms of technology where hospitality is still catching up.

Gil: But on the flip side, we also have this kind of new wave or where. New digital experiences are now occurring, um, or things can be automated. So we’re doing a bit of catch up, but there’s also a lot of advances. What have you seen you, you’ve been in this, you’ve been covering this space for a close to a decade now, if not more.

Gil: What have you seen in terms of the trajectory of growth and kind of where we are on that trajectory?

Jessica: I would say pretty huge. Pretty huge. So if we talk about, like you talked about your own property management, your own hosting business, and, and I asked you what tech tools you use, and you’ve told me like at least six. Tech tools that you use. You know, perhaps five years ago, 10 years ago, if I’d asked you that, you would’ve said, I’m using a pen and paper, you know, I’m using, or I’m using a spreadsheet.

Jessica: Probably you might have said spreadsheet. Somebody else might have said pen and paper. So the fact that even. Uh, like hosts that might have under five properties are using technology to run their businesses is pretty, kind of phenomenal, to be honest. So, so that kind of growth in the, in the penetration I guess of technology across the industry has changed.

Jessica: There’s still huge amounts. ’cause there’s still, of course, so many kind of operators that are still not using technology to run their businesses or not using it in ways that that make, you know, efficiencies really, you know, significant. But that’s been a big change. Then also, if you go, you know, you just go to any trade show and you’ll see like literally, you know, so many dozens, dozens, dozens and dozens of vendors.

Jessica: That are, um, you know, have tools and solutions for property managers and that, you know, that explosion in the types of technology, you know, is, is, is, is still really relatively recent. You know, it is only in the last five years or so that that’s kind of really come. And I do think that COVID and the pandemic really kind of.

Jessica: Accelerated a lot of the technology kind of adoption if you like as well. You know, that, that we saw a lot more coming. We, in that period of time as well, we saw a lot of investment in tech companies. So I think that, that the fact that there’s so much choice and there is more penetration is probably the two diff, you know, biggest ones.

Jessica: There are of course things like, there’s so much more, you know, there’s AI tools now, which we didn’t have. Two or three years ago, there’s way more on the guest relationship and the guest management and the guest experience than, than we would’ve had before. So there’s, you know, there’s been a lot of change.

Gil: Yeah, I, I, I’ve noticed that myself too, and I think that you, you, you mentioned this, that. We have over the last few years, you’re now suing seeing hosts that have smaller portfolios, have a much heavier tech, tech stack. And I think in the past, it’s not like the technology didn’t exist. PMSs have been around for a long, long while now, but it feels like.

Gil: In some industries where folks are going up market, this industry is actually going down market where we’re starting to see a lot more tools for the more independent operators or the smaller portfolios. I don’t know if you’re seeing the same trend where there’s a pretty big concentration of innovation happening for the smaller host now.

Jessica: And there is a really good commercial reason for that. And it’s the fact that, you know, something like, what is it, 90% of the market is smaller hosts. So for the tech companies, it makes sense to be able to provide solutions and for, for that market because it’s, it is the majority of the market.

Gil: Yeah, we, we often forget that it feels like from the outside that you have these really big property managers that. Dominate certain, certain markets out there, but it’s actually quite the, quite the opposite. Um, that where a majority of you you can think of, like specifically Airbnb for instance, you majority of them have sub five properties there.

Jessica: Yeah.

Gil: Yeah.

Jessica: it’s, you know, there’s huge opportunity if you are able to really capture and, and find that that part of the market, you know, it’s huge opportunity.

Gil: Yeah, and I’ve had a chance over the years to really meet a lot of the founders kind of in our space, and I find that. I don’t know if that there’s an inherent bias in this because I, I am one of them, but I find that the folks that build the technology from within, they’re solving their own problems, are the ones that are getting really creative about how to, how to approach things.

Gil: I don’t know if you’ve seen something similar in your side. Um, if you’ve seen a difference in folks that invested in the technology because they saw an opportunity from the outside versus folks that were building a tool for themselves and they’re like, oh, actually this is. Quite useful. I’m gonna, I’m gonna allow other people to use it and starting to build a, build a business around it.

Jessica: Yeah, it’s a really good question and I would actually say both. So, and I’ve had the pleasure of working with and quite closely sometimes with some really, really. Amazing founders in this space and some of them that have gone on to really build, you know, incredible tech businesses that by any standard of any kind of qualifying would be considered extremely successful companies.

Jessica: And I, what I find with the ones that are, that, that have become really successful is that they are, they are really driven to. Succeed at something. And also the ones that I think are the ones that really kind of succeed are the ones that have really put the customer first. So they’re obsessed. With their customers getting what they need and their, and, and really meeting that need of their customers.

Jessica: So yes, if they’ve got experience of managing, you know, having their own Airbnb or having their own property management company, of course inherently they understand the challenges that running, you know, either being a host or a, you know, a larger property manager has. Absolutely. But I, I’ve also seen some incredible sort of success stories when.

Jessica: You know, people have seen the opportunity in this space, but haven’t necessarily been operators themselves initially. Yeah.

Gil: Yeah, I think that’s a really, really good point. Um, I do know a lot of founders that come from outside of the industry or just was doing something completely different before. Um, but I think you’re a hundred percent right that the folks that are. On the top, and they’re doing quite well, are the ones that are very, very customer obsessed.

Gil: Um, craft estates, we are very, very customer obsessed. Um, I still, as a CEO, I still onboard every single one of our clients. I don’t care if you’re a property manager with one property or you have a hundred properties, it, to me, it doesn’t matter because. I use each one of those onboarding calls as a way for me to understand how people are using our product, what they’ve used, how they’re using it, and how we can ultimately improve the product.

Gil: Um, so we are very, very customer obsessed, but I’ve also seen folks outside the industry, um, here in the United States. We have not necessarily technology companies, but service providers like. Uh, John Wicks, uh, from Good and well, and he comes from outside the industry, um, but he’s ingrained himself so much.

Gil: He’s on advocacy groups as well too. Um, the folks from Canon, like they come from outside the industry as well too, and they’ve created something way, like way different, but they are super obsessed with the whole entire journey there.

Jessica: I think with vacation rentals, short term rentals, it attracts very passionate people who are, who really see it as a. You know, get, I don’t know whether it is because it’s got that hospitality kind of aspect of it, or whether it is, because there’s a lot of SMEs, small kind of medium enterprises. It’s not corporate at all.

Jessica: So it really, the enthusiasm, the kind of the passion that you see across it, whether it’s property managers, the hosts and operators, or it is the tech side, you know, is, is really quite amazing.

Gil: It. That’s, I think you’ve picked up on 2, 2, 2 things is the SME side of things, like a lot of them are like small businesses helping other small businesses. So there’s this like inherent community within, within the space. Um. But at least for the folks that come from the industry, the folks that are doing really well as property managers and hosts, they care about hospitality.

Gil: Like for me, if I get a message or an email from a client that that has a question or has trouble with anything. My hosting side takes over where I feel like I need to answer that question right away, and it could be at nine, 10 o’clock at night. And I don’t necessarily, like, I shouldn’t be at the computer and answering things when I should be with the family, but it’s the hospitality side.

Gil: It’s hard to break through. It’s really, really hard to break that.

Jessica: Yeah, it’s, it’s, I think about this a lot actually, and it’s service. So, so if you, if you’ve got that kind of hospitality mindset, you’ve got a service mindset. So you are always thinking about making sure that the needs of whoever you are serving are met, you know, the guests that are staying with you, or if as your tech company, it’s your, your customers you know of, of that.

Jessica: So I think, and I think that is really hard to train. That, that kind of service hospitality kind of real sort of, um, I guess it’s a mindset as well. It sort of is. You can kind of learn the basics, but you kind of have to have it inherently in your culture, in your day, DNA to do that. And it’s interesting, I’ll often, like if I’m hiring for team in our team. I will often, if they’ve had experience working in hospitality and by hospitality, by that I mean the broader, you know, whether they worked in restaurants, they know how to put the customer at the center of the experience in a way that you maybe don’t get if you kind of work in other places. Even retail doesn’t really have that.

Jessica: Not in the way that, um, hospitality does.

Gil: Yeah, you’re, you’re absolutely right. I think for retail, it’s very transactional. It’s, it’s about serving and then getting that sale there. Where in hospitality, like you mentioned, it’s a services business there where. Mm, after they made, after the sale, after the booking, after the stay, the service doesn’t stop there with us.

Gil: We still try to make sure that they continue to think about us, and we think of it more as like, we wanna make sure that they remember us. They, that it’s a brand, they have a good feeling when they leave our properties there. So it’s a very different thing and I, I a hundred percent agree with you that. Maybe it’s training, maybe it’s inherent, but like I a hundred percent agree that it’s, it’s culture there. Like we do the same thing. When I hire folks on our team. We have a really high bar in terms of just what we wanna deliver to our customers. Even down to the engineering team. The engineering teams.

Gil: When, when we see bugs and we report bugs that, that, that may occur, the engineering team almost feels. Someone guilty that they let things slip through. Um, and hopefully these are like small little things that doesn’t impact a wide user base, but we try to address things very, very quickly because what we don’t want is for someone to have a bad experience and.

Gil: One, they could leave us for something else or they talk bad about us. To, to someone else like that, to us is like the complete opposite of what we want from our experiences. We want folks to talk great things about us. They, they, we want them to feel like we’re taking care of them and we’re being proactive on things.

Gil: So I, I a hundred percent agree that it’s a culture thing. Yeah. Where do you, so you see kind of the market expand and all these new technologies come into play. Are there any gaps in the market that you’re seeing right now as, as you maybe even compare it to other industries, um, or maybe even use cases that you feel like hasn’t been addressed yet?

Jessica: I pretty sure there’s quite a lot of gaps. Can’t think of any right off the top of my head that are sort of glaring ones, but I, you know, there. And one of the other things actually from the book that came out is that no operator is a hundred percent happy with their technology. So that’s kind of a gap there.

Jessica: Like, it, it doesn’t all seamlessly flow and it doesn’t all work together. The data’s not all, you know, all in one place. It’s, it’s still siloed. So I think that that, I guess if I was gonna say there’s a gap, there’s still work to be done on that, on that kind of really seamless. You know, seamless, um, experience of using technology.

Jessica: The other gap that, that isn’t necessarily so much of a gap, but it is. Another also theme that, that came through the book is that a lot of people aren’t necessarily knowing how to use the technology that they already pay for. So, so they’re only using it using elements of it to a certain extent, not the full extent.

Jessica: So they may have a PMS. That is a really good PMS, but they’re only using maybe 30, 40% of the actual capability of that PMS. Like they’re not really seeing or understanding the rest of it, that that can be used for them.

Gil: Why? Why do you think that’s the case?

Jessica: I think it’s education, so it’s perhaps, and I mean it’s, and it, it’s not really understanding and knowing.

Jessica: That. So I, so I guess it’s actually two things. It’s not really always knowing what your problems are, so you know, not knowing where, let’s say if it was automation where automation can help you. So not understanding where your own gaps are, but then also not really understanding the software that you are buying.

Jessica: You know, not really understanding what it’s capable of. And you know what? If you think about it, it’s like that with any kind of software we buy for anything, you know, we only use an, you know, we don’t use the whole capacity, you know, we are on Riverside right now. You know? I bet you don’t use the, well, maybe you do, but the whole caboodle of what Riverside can do for you.

Gil: Yeah, I don’t, I, well, I think also like I end up kind of to your seamless experience, like I augment it with other tools to help me. Slice and dice the, the, the podcast into smaller reels that we can post onto our short form in, uh, social media. So I use other, and I, I, I use other tools to kind of augment that, but now I think Riverside has advanced quite a bit more recently where it does some of that stuff natively.

Gil: And uh, she has a layer of AI involved into it as well too. Um, and I guess that’s kind of analogous to our industry where I think because some of these things are so new. We don’t know what to expect when we’re onboarding something like, so say for instance if you are using Airbnb’s pricing for a long while or you set a standard rate and you start going into dynamic pricing and maybe you use a price lab or a wheelhouse, it’s a whole new world out there you that you’re now having to learn.

Gil: And you’re not just learning about how to operationalize things, but the reports that I might have in there to help you understand kind of where you fall in your percentile or what your lead times are. These are all new things that hosts have to learn. They’re not just learning technology, but they’re learning new frameworks, new methods of things.

Gil: And for a lot of us, I think the big discrepancy is that. Unlike other industries, I feel like hospitality is one, especially for hosts, are ones that we aren’t necessarily trained on. We come into it because maybe we bought that first property or we’re looking to get out of our W2 or normal income and we’re trying to do investments or arbitrage or different ways of getting into leveraging real estate.

Gil: We never thought that we’re gonna grow a business. And there’s there, yes, there’s guru, like there’s um. Of courses out there, but there’s many ways of attacking it. And we’re not necessarily bred to, uh, or trained to do hospitality, so we’re having to do it little by little. And we get like, oh, people are saying I should have a PMS.

Gil: Oh, I should have dynamic pricing. And so you start to dabble in those different things. But there is not a linear path that you do all these things in successions.

Jessica: Yeah, and it’s, you know, most hosts are accidental hosts. As you say, it’s, it’s not, it’s not always a sort of a game plan. You don’t go to university or grow up thinking I’m gonna be a professional host or a professional property manager. The other thing I’d say to that is it’s not necessarily inherent to know about hospitality.

Jessica: The other thing is it’s not inherent to know how to run a business. So there is a sort of a, a, a, a big difference between being employed. To do a task or even a management function compared to what it is to actually run a business. So, and there’s also a difference between being an entrepreneur, starting a business, to then actually running a functioning business that, that, you know, has all the elements that a business requires.

Jessica: So it’s a very different mindset and skillset required for running a business. Compared to, let’s say, having an investment portfolio or, or any of those things that that might be the reason that you’ve become that accidental host.

Gil: Yeah, you’re absolutely right because if you think about like the long-term rental space or the commercial space, there’s almost like there’s a path of how to scale your portfolio. There’s a way to underwrite, there’s a way to vet properties, there’s a way to pick different markets out there, how to choose your property management team.

Gil: There’s a very linear path and frameworks to kind of guide you through that. Uh, but you’re absolutely right that folks that get into hosting, they don’t realize that, oh, I didn’t just buy a property. I just started a business, and now I have to keep my books in order. I have to hire a team. I have to like operationalize all my, all my revenues and do tax reporting.

Gil: Like there’s a lot of stuff that goes into it. Designing your space, figuring out how to do a lot of the automations to, to make sure like you’re not bearing yourself. But I think folks, oftentimes they underestimate kind of the, the lift it takes when you’re going into short term rentals or, uh, vacation rentals in general.

Jessica: Mm-hmm. It’s also, there’s no, um, it, it’s kind of on, it’s always on. You know, property managers tend to be extremely hardworking, putting in a lot of hours into their businesses.

Gil: Yeah. Given, um, kind of similar to my last question about the, the gaps in the market. Where do you see things growing now, or how do you see things evolving over the next five years? Do you see consolidation of, of certain products coming together? Do you see more of this kind of shotgun where people are closing certain gaps here and there?

Gil: Like what do you, what have you seen of them and absorbed.

Jessica: I think that it is inevitable that there will be consolidation. Because it’s not sustainable to keep running. And what, I mean, I guess I’m looking at it from the tech side. Is that what you

Gil: Yeah. Yeah. From the tech enablement side of things.

Jessica: Yeah, the tech enablement side of things. So I think that from the tech solution side, that it’s inevitable that there will be consolidation.

Jessica: There are, there are so many too many different tools out there, and it’s not. It’s just not sustainable to keep running them. You know, we’ll see quite a lot, probably just sort of go away in the background. The bigger tech companies will buy up smaller ones. There’ll be mergers. You know, it’s just not sustainable to have, you know, X amount of guest communication tools and X amount of AI tools like. There will become clear leaders and winners in all the areas. You know, we already see that to a certain extent in kind of the PMS market. You know, there are clear leaders and some of the smaller ones are sort of, you know, they’re, they’re struggling. They’re either being bought or they’re. Kind of, you know, disappearing.

Jessica: So I think that is inevitable over the next five years that we’ll see, you know, that consolidation of technology from property manager perspective and, and that sort of side of it. I think we’ll see, we’ll see much more tech adoption over the next five years. You know, especially ai, just that, you know, it’s a normal part of life.

Jessica: Increasingly that we are using AI tools for, for whatever it is in our lives. It’ll be the same for hosting and property management. So I think that that is, is a kind of an inev inevitable that there’ll be more and more of that. The other kind of thing that we haven’t yet talked about is what the guests are actually expecting.

Jessica: So the guests really are expecting and want a more digitalized, intuitive. Experience when they’re purchasing something and staying in something. So I think that is where we’ll see also more and more tech enablement for that digital customer journey.

Gil: what do you say are some of the opportunities there? Um, in terms of kind of the gaps or in terms of the guest expectations where maybe they’re not being met or they’re met in some convoluted ways now, and maybe in contrast how some companies are kind of approaching and addressing those, those areas.

Jessica: So I think it feels like it’s a really obvious answer to this, but I actually saw a post on LinkedIn that that expressed it in a really good way and. Uh, and actually before I sort of get to that, what I will talk about is in the book, the last sentence is from Ryan Killeen, who is the CEO of the Annex, the co-founder of The Annex, which is, uh, an in an independent hotel in Toronto. And his last, the la, I used it in the last line of the book because he basically summed up what pretty much all of the leaders that I interviewed said is that the future of hospitality is hospitality. So despite everything that we are talking about about technology, and we can talk about ai, we can talk about automation, we can talk about all of this stuff.

Jessica: At the end of the day, it is about hospitality. So I think what we’ll see is that more, um. We will, what we’ll see is technology being an enabler for hospitality. So. That the, the bits where the human side is really needed, and that is around context and empathy and just, you know, being able to kind of make sure that somebody’s got a warm cup of tea, if they want that warm cup of tea, or making sure that things are as they, as they want it and, and, you know, providing experiences that don’t feel automated and like everybody else is having them.

Jessica: That’s where the real kind of. Winners will be is those that understand and are able to deliver, that they’re able to use technology to automate all, all for efficient processes and all the things that, you know, that really good personalization kind of piece that can happen, but actually not forgetting that this is a human experience business as well.

Gil: Yeah, I think that’s a good point where I feel like maybe in the last few years a lot of the technology has really been around automation and efficiency of of, of things. And every so often we will see folks that really put. The hospitality experience first and or they’ll sprinkle it kind of within their, within their product.

Gil: And I, I do think that there’s a, a pretty big gap if you think about kinda like your scenario scenario there of like. Anticipating what guests will need when they’re staying at our property, making sure that they have access to those things, making sure that you’re proactively telling them how to take advantage of the property that they, that they rented from us.

Gil: There’s still a lot of gaps in there and I, I know that there’s folks that are doing upsells and, um, doing kind of, uh, ad hoc delivery ad properties, um, things of that sort. It’s still very hard to execute on some of those things. Um. Hotels can do it because they have staff on site that they’ve trained and they’ve automated and they have SOPs on those things.

Gil: But when you’re talking about a portfolio of homes that are scattered across that, that is really hard to execute on, that hospitality is really hard to execute on.

Jessica: It is, absolutely. But that’s where hospitality doesn’t always have to be in person. You know, I believe quite strongly that hospitality can be delivered through digital methods. It’s just more about making sure you understand who’s on the, on the receiving end of it, and, and seeing your guests as a, as an individual, not seeing them as a, you know, mass, mass.

Jessica: Audience or whatever. It’s really understanding the individuals that might be staying with you.

Gil: Yeah, we’re thinking about this a lot on the craft estate side, about like personalization. I’m starting to see. More and more of this, and I think this is enabled by kind of this influx of AI where now computers can understand intent and can parse through different things that wasn’t possible before, without heavy loads of humans.

Gil: Kind of met in the middle there, where now AI agents. Can help you respond back to guests. They’re able to read why they visited your place or the kind that first message that they left you and making sure that you’re sprinkling that throughout your, your, your messaging. I think that’s super clever. Um, and it gives that kind of that warm touch to the guests that’s staying at your property.

Gil: If you mentioned that. I can’t wait to host you for your anniversary because they may have mentioned it in when they’re messaging. That’s a very magical experience there. Um, and it’s only possible now because we have technology that’s reinforced there. Um, and I think about like oftentimes. Folks are starting their journey kind of in the discovery PA phase.

Gil: They’re doing research, they’re finding the right property for them. Um, and so there’s a lot of information that’s upstream. How do we think about personalization at that level, but also passing it through to when someone books with you, so like we’re thinking about new digital experiences that kind of, kind of blends all that stuff.

Jessica: Absolutely. And, and the thing that I often think about, and it, it, it’s kind of, again, of quite an obvious example, but if you think about, most of us have Netflix, you know, or Amazon, right? We have Amazon accounts, we have Netflix accounts, Amazon and Netflix. You know, generally speaking are pretty good at being able to think about what we might want next.

Jessica: You know, we, we look at our Netflix accounts, it’ll say, these are the documentaries that you might be interested in ne next, or here’s the TV shows that match your, your previous viewing habits. And that, you know, that’s a way of understanding your customer and personalizing to your customer. And they’ve been doing it for a long time now.

Jessica: Same with Amazon. You know, it knows our shopping habits and it delivers up things we might want next. So to be able to kind of provide that kind of, and you know, that’s not even deep personalization, that’s just based on algorithms of what you bought or watched before, but we don’t even really do that, you know?

Jessica: Right. In hospitality yet.

Gil: Yeah, and I think that’s somewhat hard, right? At least right now with the technology that’s in place, because we don’t have. The data behind it, like Netflix and Amazon is able to know kind of which recommendations are because they have historical information about the shows that you watched, um, and how long you’ve watched them, or the genres that you, you tend to kind of gravitate towards or the things you shop for.

Gil: But if you’re thinking about our hospitality space right now, the only one that really can execute on something like that. Are the big OTAs because they know your search history, they know your travel history. They know how many pop people that stayed at your, that you’re searching for. They have that information, so they have the data to do so.

Gil: But I think that there’s still a pretty big gap in terms of how individual hosts are able to do that. Um, and I’m interested in kind of seeing how that evolve. I, I think that that is a very solvable problem there, especially when technology start to work together. When your PMS is able to talk to your CRM that’s able to talk to your messaging service, like those, those, if those connections are there, it can allow for that seamless experience.

Jessica: Mm-hmm. Absolutely. And that’s where it’ll get very interesting.

Gil: Yeah, I, I think a lot of times I feel like there’s this big explosion of technology and there there’s still like things that we’re trying to get to, but I feel like there’s almost a generational step that we haven’t even approached yet. And when we do, it would almost feel like more recently how AI is coming into our space and disrupting things and having us think about things very, very differently.

Gil: Hospitality, I think, will come to a, some very similar shift there.

Jessica: I agree.

Gil: Um, talk to me a little bit about kind of how technology is enabling or may make it challenging for folks to kind of get into kind of owning their own experience and kind of why maybe like hosts are now trying to become independent and spending more efforts into direct bookings.

Jessica: Mm-hmm. Because we, we are seeing a huge, and we’ve seen it for a few years now, that shift towards direct bookings and that certain desire to have more control. And I think there’s actually quite a few reasons behind it. And one of them is about having more ownership over your own business. Like if you put all your eggs in somebody else’s basket to get your customers.

Jessica: Then you make yourself very vulnerable. You know, it’s great when it’s working, you know, and it’s a win-win, but it’s, you know, it’s not always a win-win. And it also makes you very vulnerable. Like they just turn some, something changes and then you’ve lost, you know, you customers. So that’s obviously one, one thing.

Jessica: The other, um, one is that. You know, we talk, you talked about the OTAs really understand the customers, or, or, or certainly they can do their version of what we see with Amazon and Netflix because they understand the purchasing history, they’ve got the algorithms, they have a certain level of knowledge about individual, you know, um, customers.

Jessica: The problem is, of course, that that information doesn’t then get to the property manager or the host, so they are blind when they get the booking. They have no knowledge of the previous. They don’t even have like email addresses or, or whatever it is. Maybe don’t even know what other guests are staying in a property.

Jessica: So not only are you giving sort of control over your um. Um, where your customer comes from, your, you know, and, and having all your eggs, eggs in one basket. You then, of course, don’t have all the information that you need to a, build the relationship with your guests. And if you are providing hospitality, of course, you want to be hospitable right from the minute that they book.

Jessica: It becomes a very clunky experience for guests as well, because what inevitably happens is operators ask for email addresses. They ask for information that, you know, as a guest we feel that they should already have because of course, booking or Airbnb have it. So, um. And, and what you, you, what you are really not having is a relationship.

Jessica: You know, the relationship only starts when they get into your property rather than all that stuff before, which is so important. That kind of stuff before, from the, from, from searching actually to actually staying is a huge part of the customer journey. That, that if you are not. Doing direct, you’re not part of, and so you don’t have that ability to kind of build that loyalty.

Jessica: I mean, I’m telling you something, you know, full fully well, but this is what, you know, this is the way I kind of see it as well. And, and actually in the book there was quite a lot of frustration about that, you know, about that relate, you know, that the OTAs are kind of owning. All of that, which means that loyalty is, is kind of, you know, you can’t really build any loyalty if you don’t have that relationship with the customer in the way that you need it.

Gil: I, I think that’s a really good point that just the, the double down on just the loyalty side of things. I’ve noticed that the type of guests that I get from an OTA probably more, more predominantly Airbnb is a very different type of guest than I would have staying that has booked direct with me. I’ve noticed that the folks that booked direct with me.

Gil: They one, they kind of, they, they found me through the front door. They, they found us through the website or our social media, but they ended up booking with us where the brand is easily recognizable from the very, very beginning. And I find that our repeats and our referrals are much, much higher with those that have booked direct versus those that have found us on an OTA.

Gil: When you’re on an OT. I feel like oftentimes you’re having to then introduce them. Introduce them, like a new brand that they should be associated with, and kind of formulating that, that experience where oftentimes we sometimes have guests that will go back to Airbnb and book a second, stay with us on there, and.

Gil: Usually, we’ll, we leave them enough queues that they’ll, oh, they’ll, they’ll know the third time they book, they’ll book directly with us. But it does take a little bit of, kind of swaying them to think about, we’re not just another Airbnb, we’re a property management company that allows you to have a direct relationship with us.

Gil: And it’s, it’s, it’s oftentimes retraining. Luckily, I have noticed that over the last two or three years. Guests have been much, much more comfortable having a direct relationship with the property managers themselves. It’s almost as if, if you remember 15 years back before Airbnb, around Airbnb around, people still booked direct, but people predominantly booked direct because the OTAs didn’t exist, and now

Jessica: On the phone

Gil: On the phone. Yeah, on the phone. In the directories. Um, in, in the classifieds, like there were really core marketing back then, and these OTAs came around and they made it much more fluid for folks to be able to discover new properties. And it’s almost as if we forgot about the marketing side of things and, and also the consumer side.

Gil: They’ve forgotten. Other ways of discovering new properties. And we’re now almost going back to the olden days and there’s this big, I don’t know if revolts is the right word, but there’s a big push for folks to wanna be independent again.

Jessica: And maybe that’s also the, the wanting to have, you know, agency over their business as well. But I do think that. The OTAs have done. Have done a huge service to the industry. Like they really have introduced vacation rental, short term rentals to a much wider audience than, than there was ever before. And they’ve, they’ve, they’ve, so they’ve introduced this type of asset class, if you like, this type of saying to, to people that have not, you know, who had ne would never have thought to stay in a rental property.

Jessica: So they’ve done that. They’ve also helped create. Many, many entrepreneurs as well, and small businesses that have really been able to kind of grow up and deliver services within that ecosystem. So even though, yes, absolutely the move towards more control over a business, towards more control over having that customer relationship is very important.

Jessica: But I think it’s not forgetting what they have actually done for the industry.

Gil: Yeah, you’re, you’re absolutely right. There’s, I make this example quite a bit, but there’s very little assets that you can buy. And put into service and me immediately be able to get, generate significant amount of revenues. You can’t do that with a lot of other asset classes. Um, so it’s amazing that you’re able to put it on some sort of marketplace and be able to cover your mortgage plus cash flow on top of that.

Gil: Um, on top of that, the, the OTAs, because of their size, they’re able to deploy massive. Resources towards regulations and making sure that we build it in a very sustainable way where without that it’s hard. And I think the industry is still struggling in terms of getting these hosts to come together, these property managers to come together and go to their local communities, their county, and really advocate for sustainable.

Gil: Short term rental practices and, and regulations there. Um, and you’re absolutely right, like they’ve done a massive amount. Um, I think kind of the, what we’re starting to see now is more so kind of the demeanor of what I think specifically Airbnb, um, booking.com VRBO. They’ve always been very balanced in terms of how they think about that two-sided marketplace.

Gil: How the guests and the hosts or property manager is, it’s almost on equal terms. Um, where Airbnb, they demonstrated maybe over the last two years that it’s. Very, very favorable on the guest side where a lot of hosts feel like, wait a minute, like they left me a bad review. That’s an unfair review. And now AI is now automating whether or not that review is gonna get removed or not, or the policy changes that they’ve made.

Gil: Um, and it’s in favor of the guest experience. It’s in favor of hospitality in many ways, but it comes at a cost as well too.

Jessica: Mm-hmm. Yeah, and I, you know, I’m not a property manager or a host, so I, you know, I don’t have the experience of what it’s like to be. You know, working with Airbnb and, and working, but I’m definitely a guest and in, in, in a way, Airbnb is doing exactly what you kind of hope it would be, which is put the guest at the center of the transaction, which is kind of what we’ve just been talking about.

Jessica: It’s like putting the customer at the, sort of the center of the transaction. Now, of course, Airbnb wouldn’t have its business model without all the hosts and the property managers and the owners. But you know, it is putting, putting the guest kind of, I guess, front and center.

Gil: Yeah, absolutely. Um, you’re working on, kind of before we kind of wrap up, you’re working on something that’s just about to be released in in the next couple, couple of days. Can you talk to a little bit us about that?

Jessica: So we are releasing our Abode Worldwide short-term rental index for 2026, which will be coming out in the next couple of days. And it’s our third edition and it’s where we highlight, and I think we’ve got around 200 or so tech companies within. The index around all their different areas, whether it’s property management software, whether it’s guest communications, whether it’s direct booking, pricing, other kinds of ancillary services.

Jessica: So there so, so past, the index is a directory of all the different kinds of technology that is available for hosts and property managers. The index also covers. Broader themes. So it’s really great for people who want to just understand the short term rental sector a little bit more. So it’s on everything from trends that are currently happening to AI and all of that.

Jessica: What’s changing there? Plus what tech companies have had investment over the last year or so. All of those things as well. So it’s not just a directory, it’s a, it’s a whole overview of where technology within the STR space has been over the last year and is heading in 2026 as well. So within it, we also have interviewed some property managers from across the globe to find out kind of how they’re feeling about things and, and how technology is helping them.

Jessica: Not helping them, what they’re kind of looking, looking for within their technology as well. So this is free, you know, it’s free from the in for the industry and it can be downloaded from our website abode worldwide. And um. We hope it’s really helpful for the property managers and hosts that are really looking to find out, you know, a little more bit more in a granular way, what technology is out there.

Jessica: So this is different from my book, which is more high level looking at trend, you know, real trends of tech enabled hospitality. This is much more granular looking at the actual tools that are available.

Gil: Is this the first annual one that you’re doing, or have

Jessica: No, it’s the third actually. So it’s the third annual one.

Gil: Nice. Nice. I can’t wait to see kind of how that has changed, uh, through, through the previous years and kind of what’s, what’s popping up now? Um, even inside the industry and specifically inside the tech space, it’s hard to keep track of all the moving pieces out there. So I, I, I think that that’s gonna be a, a load of information that’s quite valuable.

Jessica: Yes, crafted stays is in there.

Gil: Awesome. Jessica. We usually end the show with three questions. So the first one, first, I’ve been doing a lot of reading. I continue to do a lot of reading. What’s a good book recommendation for me?

Jessica: So I am an avid, avid reader, so I read all the time, all kinds of books, and actually the first book that comes to my mind is actually an old book, and it’s was that.

Gil: I. I love book recommendations that are written beyond the last few decades because I find that those books that have been referred to over and over again and maybe have multiple editions, they’re built on really strong core foundational pieces. They’re usually not trendy, they’re not about the latest shifts in things, but they’re really grounded where.

Gil: Oftentimes I find myself like reading those over and over again as a kind of a reminder more than anything else.

Jessica: Yeah, absolutely. And this book, I actually read it. A number of years ago, and the reason I’m thinking of it, ’cause I picked it up again recently and it’s actually the power of Positive Thinking by Norman Vincent Peel, and it’s really around mind. You know, it’s an absolute classic of kind of. You know, new thought literature or whatever, and I, it’s just the first one that kind of came to my mind because I’ve read, reread it really recently, and I thought, wow, this is really powerful stuff for, and you know, especially for entrepreneurs and business leaders, you just wanna get to the, you know, the, the core of how to be thinking about.

Jessica: Anything in life, but particularly if you’re thinking about your business, the power of positive thinking is, is a really, and it’s, you know, it’s much deeper than the, the title sort of, you know, makes it, makes it sound, it’s really about mind shifts.

Gil: Nice. Nice. I definitely will, will pick that one up. Do you have a recommendation on is this a book to be consumed hardback, Kindle, Kindle or audio form? Do you have a preference on, on that?

Jessica: So with my copy, I have a very old tattered paperback copy and it’s the kind you can dip in and out of. So, and for me, I actually like both. I like Kindle and I like, you know, proper books. And you can see behind me, I’ve got all my kind of business books there.

Gil: Yeah. Awesome. Um, second question. What’s, and maybe related, but what’s one piece of mindset advice that you would give to someone that’s starting something completely new?

Jessica: So one I would say is that failure is gonna happen. And resilience is really the name of the game. So I think it’s knowing that you are going to make mistakes and that you are gonna fail and it will all go wrong for a period of time. But actually the important thing is to get up, dust yourself off, carry on, take risks, build resilience, and, and really it’s around being consistent is, is what you need, you know, is, is kind of the root of success and some luck.

Gil: Yeah. Yeah, definitely, definitely a little bit of both. I, I like specifically one line you just said there about that it can all go wrong, but for a period of time, because I find like that, that period of time is the actual, is the important piece because as an entrepreneur you’re always gonna have your ups and downs, ups and downs.

Gil: But it’s oftentimes. Those periods where you get downs for a longer period of time that you anticipate, that’s often the hardest ones because those are the times where you have to really pick yourself back up and try to motivate yourself. So that reminder there, that that actually might be normal. Um, that it’s not necessarily you’re doing something wrong or you have the bad, you have a bad idea that it just, it may take some time.

Gil: Um, for a period of time where you might not see some gains for a little while.

Jessica: Absolutely. It’s, it’s really cyclical, isn’t it? So even if you’ve got a successful business, you’re still gonna have down times.

Gil: Yep. Awesome. Last question, what’s one tactical advice that you would give to someone that’s either getting started in direct bookings or trying to amplify it?

Jessica: So I think it’s really educate yourself on. What you need to do to get direct bookings. So really think, think about the kind of the, the strategy that you might wanna put in place to get those direct bookings. What tools you might need, how you go about it. Like you can’t just wish for more direct bookings.

Jessica: You know, it takes quite a lot of work and quite a lot of planning and thinking in strategy to, to really get a very successful direct booking strategy within your business.

Gil: Yeah, you’re absolutely right. Um, and then that, I think that’s kind of the core of like why we end up starting this podcast in the first place. In the very beginning, we would launch these beautiful websites that converted really well, but we were finding that folks didn’t have the knowledge to really build that marketing engine and really had all the resources that they need to drive traffic to it.

Gil: And I don’t have all the answers. Um, I have a handful of tactics that I’ve tried and strategies that I’ve tried, um, to help me and my portfolio kind of get to the point where we’re at right now, but. I found that to be much more beneficial to bring in the best folks in the industry and have them share the different things that they’ve tried, the different marketing strategies.

Gil: And everybody I find has a different way of approaching it. And what’s quite unique about direct booking is that everybody’s portfolio is different. Everybody’s skill sets are different, and. You need to figure out what is that skill set, that portfolio that feels right to you, that you can do in a sustainable way for you to drive direct bookings.

Gil: Even though I may be in the Smoky Mountains with many of my peers. They have certain connections, they have the ability to tell a story better in some certain ways, or they’re able to build a social media better than I can and they’ll have a very different strategy. And I’ve seen many folks in the same market have very different strategies and it’s very interesting to see how they’re able to be successful in something that I may not be able to execute on.

Gil: So I, I love like just bringing folks into this podcast to just share kind of what worked for them.

Jessica: Mm-hmm. No, absolutely.

Gil: Awesome. Jessica, it was a huge pleasure having you on. Um, I am quite happy to see your LinkedIn post, uh, a few weeks back about your book and having the opportunity to meet you here and kind of have you share just what you’ve seen in the industry over the last decade and more recently. What some of those shifts are and kind of where the industry’s headed.

Gil: So I thank you for the time and kind of your energy that you brought to the show and kinda educating us.

Jessica: Thank you, Gil. I’ve really enjoyed the conversation and meeting you as well, and I look forward to meeting you in person.

Gil: Yeah, I think probably the next time we’ll get a chance to meet is maybe Burma.

Jessica: Absolutely. I’ll look out for you.

Gil: Awesome. See you then. Bye.

Jessica: you. See you.