“Your website is everything. It’s your marketing. It’s your digital front door.”
Frank Bosi from Hostfully knows what separates hosts who struggle with direct bookings from those who thrive. In this episode of Booked Solid, Frank shares the small, intentional steps that build sustainable direct booking revenue—without burning out. From his luxury hotel background at Ritz Carlton and Four Seasons to leading partnerships at one of the industry’s most customer-obsessed property management platforms, Frank breaks down exactly how to build trust, create seamless guest experiences, and finally take control of your booking channels. If you’re tired of feeling stuck on OTAs or wondering why your website isn’t converting, this conversation will change how you think about your direct booking strategy.
Summary and Highlights
🎯 Meet Frank Bosi: From Luxury Hotels to Short-Term Rental Innovation
Frank Bosi serves as Senior Director of Partner Development at Hostfully, where he’s spent over five years building meaningful integrations and helping vacation rental operators scale their businesses. But his journey into the short-term rental space wasn’t conventional.
Frank’s career began in luxury hospitality, working in leisure and corporate sales at prestigious properties like the Ritz Carlton and Four Seasons in New York City. When he relocated to Charlotte, North Carolina to open and rebrand a luxury hotel, he brought with him a deep understanding of what makes guests book direct: trust, consistency, and exceptional experience at every touchpoint.
COVID changed everything. Six months into his new role, Frank was laid off—but that setback became the catalyst for discovering Hostfully in September 2020. The skills he’d honed in hospitality sales transferred seamlessly to the vacation rental world, and he quickly recognized that the principles driving direct bookings in hotels applied perfectly to short-term rentals.
Now, Frank champions a philosophy that resonates throughout Hostfully’s culture: partnership over transactions, responsiveness over automation alone, and co-building solutions with the very hosts they serve. His approach reflects his Type A personality—hands-on, detail-oriented, and deeply invested in customer success.
💡 Key Takeaways: What You’ll Learn
Frank’s conversation with Gil reveals practical wisdom for hosts at every stage. Here’s what this episode covers:
Your website determines everything. It’s not just a booking tool—it’s your brand’s first impression and your most powerful marketing asset. If guests can’t book in two to three clicks on mobile, you’re sending them straight back to Airbnb.
Direct bookings aren’t one dramatic shift. They’re built through small, intentional actions stacked over time. Start with a trustworthy website, layer in email marketing strategies, add strategic discounts, then introduce upsells and automation.
Culture drives customer experience. The most successful property management platforms don’t just build features—they listen relentlessly to users and protect team culture even through rapid growth.
Luxury hotel principles translate perfectly. Whether you’re managing a five-star Manhattan property or a three-bedroom rental in Houston, the fundamentals remain: clean design, transparent policies, professional photos, and ownership of the guest relationship.
Digital guidebooks aren’t just nice-to-haves. One Hostfully customer reduced support calls from 12,000 to 10,000 monthly while increasing revenue by 6%—simply by deploying comprehensive guidebooks across their portfolio.
🏡 Why Your Website Is Your Digital Front Door
Frank doesn’t mince words when it comes to website performance. Having worked with some of the world’s most recognized hotel brands, he understands that booking experience directly impacts conversion rates.
“The first thing is your website is everything,” Frank explains. “It’s your marketing. It’s your digital front door, and it has to be simple, clean, mobile friendly. And guests should be able to book it in about like one, two, max, three clicks.”
This principle matters more than ever as mobile optimization becomes non-negotiable. If your booking flow feels clunky or confusing on a smartphone, guests will default to the familiar simplicity of OTA platforms.
Frank emphasizes that your website represents your brand’s first guest interaction. That experience sets expectations for everything that follows—from check-in communication to the stay itself. Hosts who invest in polished, conversion-optimized sites see immediate results because they’re finally capturing the traffic they’re already generating.
The integration between Hostfully and CraftedStays exemplifies this philosophy. Rather than settling for embedded widgets that feel disconnected, both teams invested significant development time creating a seamless booking flow. Dates selected during property search carry through to the booking engine. The experience feels native, not bolted-on.
“We don’t want to just be another logo on Hostfully’s marketplace,” Gil notes. “We want folks to have a really good experience.”
Understanding how to write a direct booking website that converts requires more than technical prowess—it demands guest-first thinking at every touchpoint.
📈 Small Steps, Big Impact: The Direct Booking Roadmap
One of Frank’s most valuable insights challenges the all-or-nothing mentality many hosts bring to direct bookings. Instead of viewing it as one massive project, he breaks it down into manageable phases.
Start with your direct booking website. Make it clear and trustworthy. Ensure mobile optimization and fast load times. Then layer in email marketing to nurture past guests and inquiries. Build in strategic discounts that reward loyalty without training guests to expect constant deals.
Finally, introduce upsells and automation that free you from inbox management while generating additional revenue. This progression allows you to learn and adjust at each stage rather than overwhelming yourself trying to implement everything simultaneously.
“Direct bookings aren’t one big push. It’s not one big move,” Frank explains. “They’re small intentional steps that build on one another.”
This approach proves especially crucial for hosts managing their first few properties. Frank consistently praises new operators who invest in proper systems early. Learning property management software and building direct booking infrastructure with one listing creates scalability that becomes invaluable at ten or twenty properties.
The alternative—waiting until you’re managing dozens of units before implementing these systems—creates unnecessary stress and often leads to costly mistakes. Hosts who leverage niche strategies early set themselves apart from competitors who chase volume without strategy.
🤝 What Makes Hostfully Different: Culture as Competitive Advantage
When Gil asks what sets Hostfully apart in a crowded property management software market, Frank doesn’t start with features. He starts with culture.
Every Hostfully customer receives a dedicated customer success manager. The company maintains 24/7 support staffed entirely by Hostfully team members—no outsourcing. Their customer satisfaction score sits at 97%, a number Frank attributes to genuinely listening to users and building features based on actual feedback.
Hostfully uses a tool called User Voice where customers can submit feature requests. The more votes a request receives, the higher it climbs in the development queue. Rather than keeping this tool hidden until problems arise, Hostfully proactively shares it with all customers during onboarding.
“It’s not something we keep hidden and bring up when you have an issue,” Frank notes. “We tell all of our clients about User Voice so they can ultimately help us grow our software.”
This transparency extends to the development team itself. Unlike many software companies where engineers remain siloed from customers, Hostfully’s developers actively participate in customer conversations. Frank jokes about occasionally needing to redirect their CTO during demos: “He’ll just talk and he’ll schmooze, and I’m like, all right, Steph, let’s talk about Hostfully now.”
The culture of responsiveness and partnership traces back to founders David and Margot, who personally handled demos and onboarding in Hostfully’s early years. As the company scaled to over 150 team members, they protected that culture fiercely.
Frank’s five-year tenure reflects this environment. He describes an old-school mentality of sticking with a company and continuously improving rather than jumping between roles. The entire sales team shares this longevity, with no resignations from that department—remarkable stability in the tech industry.
📱 Digital Guidebooks: The Underrated Revenue Engine
One of the most compelling case studies Frank shares involves Cabins For You, a hospitality company managing over 350 properties. Before implementing Hostfully’s digital guidebooks, their guest relations team fielded approximately 12,000 inbound calls monthly—many addressing repetitive questions about WiFi codes, check-in procedures, and local recommendations.
Within one week, the team created 345 individual guidebooks using Hostfully’s template system. Each property received customized cards covering arrival instructions, local attractions, restaurant recommendations, and house manuals.
The results? Inbound support calls dropped from 12,000 to 10,000 monthly—a 15% reduction. More impressively, revenue increased by 6% as the team shifted focus from answering repetitive questions to solving complex problems and pursuing growth initiatives.
Frank emphasizes that guidebooks serve multiple functions beyond reducing support burden. Hostfully’s partnership with Viator enables hosts to earn 8% commission on any attractions guests book through the guidebook. The Marketplace feature allows direct upselling of wine packages, pet amenities, and other add-ons.
Perhaps most strategically, guidebooks can include splash screens requiring guests to agree to property terms while simultaneously collecting email addresses—creating a crucial loophole around OTA contact restrictions and building your marketing database for future direct booking campaigns.
“That’s a direct line to market audience for direct bookings,” Frank explains, noting that Cabins For You saw significant increases in repeat reservations after implementing this feature.
Operators who combine guidebook strategies with community-based marketing create powerful flywheels for sustainable growth.
🎓 Lessons from Luxury Hospitality
Frank’s background at Ritz Carlton and Four Seasons deeply influences his approach to vacation rental success. In luxury hospitality, every touchpoint matters—the tone of emails, room presentation, check-in flow, and mid-stay experiences all contribute to guest loyalty and repeat bookings.
“In luxury hospitality, every touchpoint matters,” Frank notes. “That’s exactly what hosts need to think about too.”
This philosophy stands in stark contrast to what Frank calls the “heads in beds” approach—viewing guests as transactions rather than relationships. Hotels like Ritz Carlton don’t just want bookings; they want guest loyalty and brand advocacy. That requires owning the relationship from the very beginning.
Gil builds on this point, distinguishing between hosts who chase five-star reviews and those who genuinely care about hospitality. Both might achieve similar ratings, but the latter group sees dramatically better direct booking performance and repeat reservation rates.
“The ones that are most successful in direct bookings are the ones that really care about the guest experience,” Gil observes. “Those are the folks that are successful.”
This mindset shift—from optimizing for reviews to optimizing for relationships—separates hosts building sustainable businesses from those perpetually stressed about their next booking. Building trust on your direct booking site requires authentic hospitality, not just technical optimization.
🔧 The Technology Foundation: Why PMS Matters First
One surprising revelation from this conversation involves how many vacation rental operators still run properties without any property management software. They rely exclusively on OTA platforms, manually syncing calendars through iCal links and connecting pricing tools directly to Airbnb and Vrbo.
Both Frank and Gil express genuine confusion about this approach. Without centralized management, hosts face constant risk of double bookings, pricing inconsistencies, and overwhelming manual work that prevents scaling.
“I find out that they have 20 short-term rentals and they’re only on Airbnb,” Frank shares about hosts he meets while traveling. “They don’t want it. I don’t get it.”
Gil reinforces this point from CraftedStays’ perspective. When prospective customers want to build direct booking websites but lack PMS systems, he actively discourages moving forward without that foundation first.
“We don’t recommend getting into direct bookings if you don’t already have a PMS in place,” Gil explains. “You want to make sure that you don’t get a double booking on Airbnb, Vrbo, Booking.com.”
The conversation reveals an important truth: successful direct booking operations require proper infrastructure. Your website, email marketing, and guest communication all depend on having one centralized system managing availability, pricing, and reservations across all channels.
Frank particularly praises hosts who implement property management software from their very first listing rather than waiting until they’re managing ten or twenty properties. Learning systems while still small creates sustainable foundations for growth.
Operators considering how to simplify their direct booking experience discover that the right PMS eliminates friction at every stage of the guest journey.
🌱 The Partnership Philosophy
The integration between Hostfully and CraftedStays exemplifies how thoughtful partnerships benefit users. Rather than rushing to market with a basic connection, both teams invested months developing truly seamless experiences.
Frank appreciates that Gil continues personally onboarding new CraftedStays customers despite company growth. That hands-on approach mirrors Hostfully’s own values and creates alignment between the two platforms.
“The partnerships specifically—we kind of have the same mindset to customer approach and success,” Frank notes. “That’s what they see and that’s what they enjoy.”
This alignment extends beyond surface-level integration. Both companies prioritize ease of use, customer success, and building tools that scale with operators as they grow. Neither wants to be just another logo in a marketplace directory—they’re committed to delivering exceptional experiences that reflect well on both brands.
Frank emphasizes that Hostfully’s strong API enables these deep partnerships. Rather than forcing partners to work around limitations, Hostfully’s technical foundation supports sophisticated integrations that feel native to users.
The result? Hosts using both platforms experience the streamlined operations they need to focus on hospitality rather than technical management. Success stories like Mark Mancini’s niche-focused approach demonstrate how integrated systems amplify results.
📚 Book Recommendations from Frank
Frank admits that as a father of two young children, reading time proves scarce. He’s accumulated an impressive library of unread books purchased with the hope of eventually enjoying them with a martini in hand.
His all-time favorite book remains Frankenstein by Mary Shelley—particularly fitting as an October recommendation with Netflix releasing a new adaptation in November.
Currently, Frank is working through A Prayer for Owen Meany by John Irving, published in 1989. He likes alternating between contemporary releases and classic literature, creating variety in his reading journey.
💭 Mindset Advice: Keep It Simple
When Gil asks for mindset advice for someone starting something completely new, Frank’s response applies equally to new hosts and seasoned property managers.
“Just baby steps. Keep it simple,” Frank emphasizes. “There’s no need to put the cart before the horse.”
For new hosts, this means starting with one small action that makes a difference—launching your direct booking site or sending your first follow-up email. Don’t try implementing everything simultaneously.
For established managers, the principle remains relevant: shift focus toward scaling smarter rather than harder. Automate repetitive tasks. Nurture repeat guests. Lean on data to refine pricing and marketing.
“Stress does not mean success,” Frank reminds listeners. “It’s more efficiency, more sustainability, and ultimately just more control over your business.”
This philosophy challenges the hustle culture prevalent in entrepreneurship. Building a successful vacation rental operation doesn’t require burning out. It requires thoughtful systems, incremental improvements, and consistency over complexity.
Frank’s own journey at Hostfully demonstrates this principle. The company grew from a tiny team to over 150 employees while maintaining the culture and customer focus that defined their early days. That growth happened through daily commitments to customer success, not massive overnight transformations.
Hosts who adopt Sarah Pell’s systematic approach discover that simple, consistent actions compound into remarkable results.
🎯 Frank’s Tactical Takeaway: Master Your Digital Front Door
Frank’s final tactical advice synthesizes everything discussed in this episode. Your website represents your most important marketing asset—your digital front door.
“The first thing is your website is everything,” Frank reiterates. “It has to be simple, clean, mobile friendly. And guests should be able to book it in about one, two, max, three clicks.”
If the booking experience feels clunky or confusing on any device, guests default to the familiar simplicity of OTA platforms. Your direct booking website isn’t just a booking tool—it’s your brand’s first impression and the foundation for every other marketing effort.
From that strong foundation, build incrementally. Layer in email marketing. Introduce strategic discounts. Add upsells and automation. Each step compounds the previous one, creating sustainable growth without overwhelming yourself.
Frank also emphasizes trust-building with guests and strategic partnerships. In hotels, branding and consistency did the heavy lifting. For vacation rentals, professional photos, transparent policies, authentic reviews, and social proof convince guests to share their credit card information on your site rather than defaulting to Airbnb.
“It’s not about a magic trick,” Frank concludes. “It’s about using the right tools and building trust with your guests.”
🔥 Rapid-Fire Questions
Book Recommendation: Frankenstein by Mary Shelley (all-time favorite), currently reading A Prayer for Owen Meany by John Irving
Mindset Advice: Baby steps and keep it simple—consistency beats complexity. One action can make a big difference. Stress does not mean success.
Tactical Takeaway: Your website is everything—make it simple, clean, and mobile-friendly. Book in 2-3 clicks max. Direct bookings aren’t one big push but small intentional steps: start with your website, add email marketing, introduce discounts, then layer in upsells and automation.
🤝 Connect with Frank Bosi
Want to learn more about how Hostfully can transform your vacation rental operations? Frank and his team are ready to help you build sustainable direct booking revenue.
Book a Demo: Schedule time with Frank
LinkedIn: Connect with Frank Bosi
Hostfully Profile: Learn more about Frank’s work
Special Offer for Booked Solid Listeners: Use code SOLID to receive $500 off your Hostfully onboarding fee.
🎧 Ready to Transform Your Direct Booking Strategy?
This conversation with Frank Bosi reveals exactly why some hosts struggle with direct bookings while others thrive. The difference isn’t luck or budget—it’s systems, mindset, and the right technology foundation.
Listen to the complete episode for Frank’s full insights on digital guidebooks, partnership strategies, and the cultural elements that separate successful platforms from the rest.
Listen to the Full Episode on Booked Solid →
🏠 Start Building Your Direct Booking Website Today
Ready to create your digital front door? CraftedStays makes it simple to launch a fast, mobile-optimized, conversion-focused website that integrates seamlessly with Hostfully and other leading property management systems.
Stop sending guests back to OTAs because your website doesn’t convert. Build a professional direct booking presence that reflects your hospitality standards and captures the traffic you’re already generating.
Start Your Free Trial at CraftedStays.co →
Transcription
Frank: The first thing is your website is everything. It’s your marketing. It’s your digital front door, and it has to be simple, clean, mobile friendly. And guests should be able to book it in about like one, two, max, three clicks. ’cause if the experience feels clunky or confusing, they’re gonna go book on Airbnb.
Frank: Or vrbo, and that’s like the main thing. ’cause it’s also your brand and that’s the first experience that guest has with you. But then going back to keeping it simple is direct bookings aren’t one big push. It’s not one big move. They’re small intentional steps that build on one another. You know, start with your website, make it clear, make it trustworthy.
Frank: Then layer in the email marketing. Mm-hmm. Then build in the discounts. Just keep that relationship going. And then finally. You know, you can add the upsells and you can automate, you’re not stuck in the inbox, and that’s really, you know, where tools like crafted stays, but Hostly also shines.
Gil: Before we bring on my guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on hearing the same thing. 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 is purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings.
Gil: And you can keep on testing and improving. As you learn, you can make changes all on the platform. 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 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 Books Solid show, the show where we bring in top operations to discuss hospitality, operations and direct bookings. On today’s show, I have the hostfully Senior Director of Partner Development, Frank Bosi on the line. He is a phenomenal person. He’s been in the industry for quite a while now.
Gil: First from luxury hotels now to really servicing the industry through technology. I’ve met him a few months back when we were doing our partnership together between crafted. Days and hopefully, and He’s just so knowledgeable, so well connected. Really what I also like is just how in tune he is with really where the market’s going, where the customers are at, what products and features are they looking for.
Gil: We have a really good discussion about really what makes Hostly different some than some of the other PMSs out there. I learned. Really a lot about what’s driving their growth and really how they’re able to be so successful as a PMS. There’s lots of PMSs out there and there’s many to choose from. Um, but there’s this different flavor that I get from, hopefully that I wanted to kind of pick apart on the show, and it’s really good to kind of hear from him.
Gil: What’s on the inside that we don’t get exposed to when we’re shopping for new technologies out there. So definitely if you’re looking for PMS, you don’t have one already, or if you’re looking to explore different PMSs this, it’s a good conversation. If anything, just to learn kind of what goes into operating a pmms and the use cases there and what makes different PMSs different.
Gil: And definitely also really just seeing how some of the things that. The company has been, uh, really focused on what some of the features that they have, some of the successes that they have, and really also like what it, what it took and what it meant to integrate into craft estate. So, without further ado, let’s bring Frank in.
Gil : Hey Frank, welcome to the show.
Frank: Hey,
Frank : Gil. How you doing? Thanks so much for having me.
Gil : Yeah, it’s about time we scheduled this, this showing so, so many months ago. It was so hard to get on your calendar. You’re
Frank : I don’t know. You’re the one that’s high in demand.
Gil : I think we both live pretty busy lives and I feel like the rest of the year is probably not gonna slow down.
Frank : Here’s the hope in my calendar. Does not look that way,
Gil : Uh,
Frank : with VRMA coming up. A lot of preparedness going into it, so we’re, we’re
Gil : yeah. Luckily we’re not, we’re not showcasing at VRMA this year, at least.
Frank : But you’ll be there. Yeah.
Gil : but I, I’ll be there. I’ll be
Frank : Don’t scare me
Gil : I’ll, I’ll be there on the Monday. Um, so any of our listeners, uh, I’ll be there Monday. I won’t be there Tuesday. Um, but I’m flying in. I mainly to kind of meet with our partners.
Gil : Um, so I definitely wanna spend some time with you when we’re out there, so, but yeah, I, I bet you, you’re, you’re, you’re busy. You guys have a big booth when you’re out at VRA.
Frank : Yeah, it’s growing year over year. It just keeps getting bigger and bigger. Uh, I remember when I joined, like five years ago, we had like the table with the cloth and like a tiny little booth, and now we’re trying, I think we have a corner this year. Um, so I’m pretty stoked for
Gil : you guys had like a double or triple booth last
Frank : We did, we, we, Pedro my boss, CRO, uh, he went, he went all out with the, with the booth last year.
Frank : He bought like the stands and the laptop holders and a whole bunch of stuff. Um, so yeah, we’ve been, we’ve been using it. We’ve been around too. We’ve been to a ton of conferences this year, uh, and anticipating more next year. Uh, so
Gil : No, you gotta tell me which ones, uh, you’re gonna be at. Uh, I’ll, I’ll, I’ll try to, I’ll try to, I’ll try to fly around, around the globe and,
Frank : Deal. Yeah. When we, when we confirm our 2026, I’ll just send you the file.
Gil : Yeah. We have a couple. Um, I. There’s no PMSs at this one, but one of my favorite ones earlier this year was level Up.
Frank : Mm-hmm.
Gil : I, I don’t know if you’ve ever been to one of those, and if you
Frank : We went two years ago.
Gil : yeah. Um, as an attendee, I, I, I didn’t experience it as a vendor, but from a, as an attendee perspective, that one’s a really fun one because it’s just so different than any other, any other conference out
Frank : yeah, yeah. And I have, I mean, my guilty pleasure and all of my colleagues can tell you is their conferences. Um, I love conferences. Um, VRMA is the biggest in the industry, obviously, but I think a lot of the ones that I’m really enjoying lately are like the small ones, you know, like level up your listing.
Frank : Um, STR Wealth, like smaller, like Summit style. Where, you know, you can, you know, have like more intimate conversation. Um, because at VRMA if, if you don’t purposely have intimate conversation, and you and I are good at that, um, sometimes it’s a little overwhelming for people. But, um, again, I’m, I always look forward to VRMA, but it’s the smaller conferences that I’ve been really enjoying lately.
Gil : Yeah, yeah, yeah. The one thing you have your, your, your team backing you on this slide, like when we go into like conference prep, like my schedule, it is packed because like I’m working with the team pretty intimately to figure out like, how do we wanna set up our booth and how do we wanna, like, like how do we wanna showcase ourselves?
Gil : And yeah. I wish I had the team that you guys have to help me relieve some of that stress. It’s, it’s stressful.
Frank : yeah. But yes and no, but sometimes like I’m more hands-on and make my, like I said, I’m, I’m I told you beforehand, type A, so when like. I have a plan, I’ll do it, I’ll execute it. When there’s like more people, there’s a lot more follow up and a lot, like everyone executes perfectly on our team when it comes to conferences, but there’s so many moving parts that you have to remember that moving part where I, I am kind of like, I, I kind of like just going and doing it.
Frank : Um, but yeah, I could, I, I could see that for sure.
Gil : Yeah. Yeah. Well, we, we, we got into it pretty, pretty deep. I think we went, we went on a slight
Frank : Yeah. Yes. This, this podcast is not on conferences, it’s on direct bookings.
Gil : um, but I want you to kind of give folks that introduction to, to yourself before we go any deeper.
Frank : Yeah. Um, I’m Frank Boce. I am the Senior Director of partner development here at hostly. Um, I’ve been with Hostly for a little over five years now. Um, and prior to that I was doing, um, leisure sales, corporate sales. Wholesale, um, at, uh, luxury hotels, uh, specifically in New York City. Uh, and then found an opportunity to move down south.
Frank : And now we’re based in Charlotte, North Carolina. Uh, opened up and remarketed and rebranded a luxury hotel down here, uh, which brought me down here and brought my family down here. And then ironically, uh, like six months in to this new job, uh, got laid off because of COVID. Um, but blessing in disguise. If it wasn’t for COVID, I would’ve never found Hostly.
Frank : Uh, so started with Hostly in September of 2020. Uh, so it’s, it’s been a ride for those five years. Like I said, our booths are growing year over year, but so is the company. Uh, so it’s been five years of just significant growth and just recently we, um, uh, we celebrated our 10 year anniversary.
Gil : I saw that. I saw that.
Frank : So it’s, it’s cool with the hospitality industry because.
Frank : And, and hospitality. But doing sales, ’cause sales is transferable, but what I learned in the hospitality industry was very transferable to the short term rental space. Um, especially with direct bookings specifically.
Gil : Yeah. Yeah. Well, congrats on, I think, one your five year anniversary. So as we’re speaking, you probably just hit that five year
Frank : Yeah. Few weeks ago,
Frank: Uhhuh.
Gil : Yeah. So congrats on that. And, and also the 10 year anniversary of, of the company or tenured birthday. I don’t know how, how you guys call it
Frank : Big anniversary. Yeah. And your anniversary. Yeah. We have a lot of, um, we have like a lot of content out there on our social media. If you don’t follow Hostfully, definitely follow us. You get all the news that way. Um, but yeah, it’s 10 year anniversary. We’re, we’re growing.
Gil : You’ve been, and you’ve been with it for half the journey. That’s, that’s, that’s pretty big. That’s pretty big, especially in the, that the tech space, like I’ve been at. A handful. I’ve been at six other startups before building this one, and five years is a long time to be at a tech company. So, and, and I think the folks I do meet that are in it for that long at one company, they really believe in the product.
Gil : But more so I find that the culture is probably what pulls them and sticks ’em in there. I, I, I, I would love to hear a little bit about you of like, kind of like how the company has grown and like what keeps you really like motivated to continue on that mission? I.
Frank : Yeah, I mean, I’ve always, I kind of have like the old school mentality where you get a job, you stick to it, and you just get better and better within the job. Um, but that’s just me. I’m one sales person on the team, but our entire sales team, I think we. I don’t think anyone ever resigned from sales on the team.
Frank : And that, you know, it’s, the culture is great. And like I said, I’ve been here for five years and absolutely love it. Uh, we are a fully remote team and we’re spread around the world. Um, but culture is something that we protect and is, and David are huge on our culture. So we put a lot of emphasis obviously, on partnership and responsiveness, um, and not, not necessarily just like dealing with clients and customers, but with each other specifically.
Frank : So our Slack channel, as much as I love it, um, it’s always blowing up with just catching up and side chats and conversations and, you know, there’s, there’s this mindset that we are just co building with, we’re co building with our hosts and our clients, um, but we’re also growing and scaling with them. And honestly, that energy just shows up in our product.
Gil : Yeah. And, and I, I work with a lot of PMSs and I have a great affinity to, to some
Frank: a lot of us.
Gil : yeah. There, there is a lot of you guys. And I think what I find is that, that everybody approaches how they run their company very, very differently. And I, I actually learn to appreciate kinda like how the different teams do it.
Gil : And I I, I do feel like from a hostly standpoint, you folks are very hands on and from the product it shows that there’s a craft to it. Um, maybe and you speak a little bit about a co co building it this together with hosts. I would love to hear, kinda hear from you, like what are some of the, kind of the anecdotes that you’ve kind of seen where that really comes through in the product development or even customer service, how you handle customers and how you just really make sure that your customers are successful.
Frank : And that’s like, that’s the biggest thing with Hostly. Uh, and that’s what really sets us apart from the other property management softwares that are out there. Uh, we always get that question like, why choose hostly over this property management software? And I mean, again, as stated, this industry is very saturated with property management softwares.
Frank : It’s a very incestuous, um, industry when it comes to different software, specifically property management softwares. Um, but really just two reasons always come up is first it’s hostfully ease of use. Um, like our platform. Approachable, uh, whether you’re managing like two units or 200 units, um, it’s, it’s aesthetically pleasing.
Frank : It’s easy to use. Uh, and even with our tech stack and with our partners, it just integrates seamlessly because we do have one of the strongest APIs in the market. Um, but then the second one is partnership, not just with our, not just with our integrations, but with our clients. So every customer, um, gets a designated customer success manager.
Frank : We have 24 hours, seven day a week customer support. Um, our csat, uh, csat, uh, I think it’s customer satisfaction. It’s our customer satisfaction score. Um, right now it’s 97%. Uh, and I think that number just organically comes from actually listening to customers and just building on software. Based on their feedback.
Frank : So if somebody says, Hey, I could really use this feature, we have something called user voice. They log it into user voice, and the more requests that it gets, that feature makes its way to the top. And our dev team, which you would think like that, usually, you know, dev teams are like separate and quiet and just stick to themselves, not at hostfully.
Frank : Our dev team is phenomenal and they have sale sales personalities. Um, so, you know, like the dev team, just, they, they want to perfect the software. They want the clients to be happy, so they listen to everything. And I mean, hostfully is not just, you know, a scheduling tool or just a digital guidebook. Like we’re an all in one platform, like you said, that grows with you.
Frank : So the property management software, the digital guidebooks, even our new, uh, Hostly devices, um, and unlike a lot of property management, softwares provide like software providers in the market. We’re really focused on just helping you own the guest relationship, um, the, the building of your portfolio, the building of your brand, and not just manage reservations.
Frank : You know, it’s not a heads in beds approach anymore. It’s really important to build on those relationships with your guests. So we, we make sure that our software can accommodate that.
Gil : Yeah, I, I definitely wanna like. Pull on that just a, just a little bit. Um, but before I, like, I, I, I want to understand a little bit more about like building your brand and owning the rest relationship. ’cause I think that has a lot to do with kind of the next segment when we start talking about direct bookings a bit more.
Gil : But I, I, I’ve definitely kind of to, to your point of like the user voice stuff, I’ve actually, I’ve posted things on the user voice before and I’m like, oh, this is actually a really good tool. And I looked into getting it for us and I was like, oh my gosh, this is a, this is a pretty steep tool that I, I, at, at least in our stage of the company, we can float the budget for it.
Gil : But it’s a really impressive tool and I, I love how you guys are using it to really make sure that at the very end of the day, the user has a voice to make sure that they can give you small feedbacks along the way. And then on the flip side, that the end kind of creator, the developer, the engineers designing the product teams have access to that as they’re building it.
Gil : Because I’ve been at many organizations before. Where there’s almost a wall between what the go to market teams say and give feedback on and what the product team, product engineering, design teams are working on. And it’s really hard for that continuity to come through. So it’s actually really nice that you guys have a tool where you’re not hearing it from your CSMs or the account managers or the sales team giving feedback of like what the customers want to wanna build or what they need help on.
Gil : You’re actually giving that direct access from the user to the product development team. So that’s, that’s really, that’s, that’s different. It’s very, very
Frank : it is. And even on our, uh, like customer success calls, I do, I always do like a three month follow up after I sign an account. Um, and I always ask ’em like, Hey, have you looked into user voice? And they’re like, oh yeah, we know user voice. So we even, it’s not like something that we keep hidden and bring up.
Frank : Like when you know, Hey, I have an issue. Here’s user voice. We tell all of our clients. About user voice so they can ultimately help us grow our software. Um, and that’s what it really comes down to in this industry again, is, is the innovation. Um, and you can’t be innovative unless you’re open to getting feedback and criticism from your who better than your own clients, you know?
Gil : I think that that’s probably gonna be the biggest difference. Like, yes, you’re right. There are a lot of PMSs out there, and there are, there’s a lot of them. Um, and I think that over time that may not be
Frank: Mm-hmm.
Gil : Um, but I do think that the ones that. Are really gonna thrive and continue to grow are the ones that are continually keeping a pulse on the users.
Gil : That’s, I’m, I’m starting to see over time that there’s gonna be, there’s a stark difference between people that market themselves really well, and there’s a pretty big discrepancy between, like, when you’re on the Facebook groups, are people saying, this is the PMS to go with, and the, there’s a discrepancy there.
Gil : And I, I, I find that more and more folks are leaning towards the ones that listen to the customers because we’re not in the same world that we were maybe five years ago. Um, things are changing faster. There’s more solutions out there. The guest expectations are, are changing, the technologies are changing and, and the folks, the pmms is, and actually every technology partner in the space, the ones that are connected to the customers the most, the ones that are taking feedback and really turning that into products that are out the market in a very short timeframe.
Gil : Those are the ones that are thriving right
Frank : yeah, yeah. Absolutely.
Gil : a hundred percent hear you on the, on the, on the CSAT side of things like that, that, that to me, and you probably hear this already, but like for me, product quality and customer service is very, very important to me as the founder of craft estate, is like I still onboard every single one of our customers.
Gil : I know it’s not sustainable. I know at some point I’m gonna have to give it away and I won’t be able to do it for everyone. But for me, it doesn’t matter if you’re a host with one property or a couple hundred doors. Like I want to get the feedback. I want to help folks be successful on our platform. And yes, I can have one of one of our account managers take that on, but that’s an opportunity for me
Frank : Mm-hmm. Oh, yeah. And I’m sure that they recognize that.
Gil: Yeah.
Gil : Yeah, and it, it’s, it’s amazing because people know, like every single one of our customers know me by name and they know how to communicate with me. They know how to reach out to me. And yes, like I kind of push ’em towards like, like customer service tools that if I’m in a podcast like this, I’m still having our team respond to things.
Gil : But it’s still nice to have that direct relationship. And again, it’s not sustainable indefinitely. And, and I’m still in the phase of the company where you do things that don’t scale. But to me, it’s, it feels like the right way to operate the company and we’ll figure out new ways of doing it
Frank : Yeah, yeah. And I mean, that’s exactly what ho like what Hostfully did, David and Margo, they were doing demos, they were onboarding people, um, and they had that one-on-one and that high touch. But yes, we scaled and they had to kind of get away from that day to day. Um, but they kept the culture and they made sure that that was a priority.
Frank : That whether you have one listing or you have a thousand listings, you’re still gonna get the attention that you deserve. Uh, because to be honest, it’s. It’s those property managers that have 1, 2, 3, 4 handful of listings that need probably more TLC than those that have hundreds of listings. You know? So regardless, no matter what the focus or what the priority is for that property manager or that property management company, they’re still priorities and there’s still needs.
Frank : So it’s kind of just tailoring those needs to what they, you know, what’s going to help them scale or, or just to, you know, make their day to day more sustainable and just less stressful overall.
Gil : Yeah, in the very beginning we, when we did this partnership and we were trying to, I was working on like marketing materials. I was like, I went to your team, and I was like, what is that sweet spot of customers that you really help? And it was hard to get an answer, uh, because I got, we went from, if you’re a small operator doing yourself up to a couple hundred doors and it’s a pretty wide range.
Gil : I was like, how’s that, how’s that possible? Like, how do you create a product that is so, I don’t know what, what the right word is, but it can kind of mold to so many different persona types.
Gil : And I think like it wasn’t until I started working with you and I were starting to bring on clients, hostly clients and we’re building out their direct booking websites.
Gil : I’m like, actually, it’s true. Like unlike some of the PMSs where they may be either on the more high, like dozens and dozens of properties and that’s what their, their niche is, or other property manager, property management systems that are like the one to six and one to twelves. Like you guys actually have a really wide, wide range where when I see a Hostly customer sign up and we, and we find out how many property accounts, it’s a really big range there.
Gil : It’s really impressive that you’re able to create a product that can graduate with a host or a property manager.
Frank : Yeah. And I think that that stems from the importance of listening to our customers. ’cause when we first started, we obviously couldn’t accommodate a 200 listing, uh, property management company.
Gil : Mm-hmm.
Frank : that 200 property management company was, wasn’t always 200 listings. They had five listings, and Hostly was their property management software with five listings.
Frank : And they grew and their needs grew, and we listened to them and our features grew with them. So I think that that kind of really stems from these small property management companies that grew to be huge and we grew with them, um, which I think helps us accommodate and, you know, service the, the one property management, uh, but also the 200, 300, 400, um, even, we even have a few accounts that are a thousand listings.
Frank : Um, and it is our response time. That helps us a lot as well. I mean, our customer success team is phenomenal. Our support team is awesome. Um, and they’re, they’re hostfully uh, associates. We don’t outsource. They’re all Hostfully associates, so they have Hostfully, top of mind, top of heart. And that’s their, that’s their main focus is we all share the same focus to just be the best property management software for that individual.
Frank : Yes. We’re not the best property management software for everyone. Not, there’s not one property management software in the industry that is, so it’s, again, it’s that conversation and, and finding out, especially on the sales side, is what we do different as well, is we sell our software. Uh, and if, you know, there’s no lying, there’s, it’s full transparency of what we offer.
Frank : And if we’re not a good fit, we’re not a good fit, but let’s keep the conversation going. Um, so kind of all in all, it’s all those like little things that kind of make us who we are, which it, you know, makes us successful.
Gil : Yeah,
Frank: Yeah.
Gil : it it, I think behind really successful companies are kind of the people and the teams behind it. And we talked a little bit about this, but the one theme that I’m picking up in this conversation. Is that there’s not a strong barrier in terms of this is my role, I’m only doing this, and there is this really like hard stance of like, okay, this is how I’m treating my role, this is what I’m doing, and I’ll pass it over to someone else if, if, if it kind of falls out of it.
Gil : You mention how the developers have a very kind of sales driven or kind of sales mindset as well too. And the thing that I am starting to piece together, and please correct me if I’m wrong, is that the team is really more in service of the mission and they all have unique skill sets that allows them to be successful at their job, but they don’t, there’s not this culture of this is my role, this is my job description and I’m only doing this.
Gil : It feels like as if the conversations are pretty open-ended, where you have this place where people can give inputs on very different direction, and it’s not bounded by the role itself. And again, I’m, I’m only picking up cues and I’m extrapolating that be between my experiences working in corporate. Um, but that’s what I’m getting from the Hostly culture.
Gil : So please correct me if, if I’m
Frank : Yeah, no, that’s, that’s exactly it. And every time like people ask like, what makes Hostfully different, I always start with our mission. And our mission is simple. It’s to help hosts take back control, but ultimately it’s to help host. Streamline and operate their day to day. Um, and really we just, that’s a huge focus.
Frank : And it’s great that we find people that have different specialties. Like, you don’t want me in Dev. Absolutely. you may want some people in dev in sales, to be completely honest, there’s a few that are popping in my head right now. Some of my colleagues are just like, how are you not in sales right now?
Frank : Um, but we, we, that’s our one mission is just, you know, just help hosts simple.
Gil : Yeah. I love it when, uh, you pull a dev into a sales call and you see that
Frank : but they do it. Yeah. Yeah, yeah. Even, um, there’s, there’s a few, uh, demos that I had, like I said, you don’t want me in Dev. Um, there, there were some technical answers, and that’s another thing with Hostly, if we don’t know the answer, we’re not gonna give you an answer. That’s not true. We take it back, we find the answer, and then we get back to you.
Frank : Whether it’s a yes or a no, it could be the answer you’re not looking for. We’re gonna, we’re gonna be full transparent with it. Um, but sometimes if it’s a big, big account, I’ll have, um, our CTO, our chief Technology officer, um, and one of the founders of Hostfully, he’ll join and he’ll, he’ll, he’s a natural, he’ll just talk and he’ll schmooze.
Frank : And I’m like, all right, Steph, let’s, now let’s talk about hostfully. It’s enough chitchat. Um, but yeah, it’s, it’s so nice to bring them in sometimes, um, especially when needed because they are a wealth of information in, in of, of
Gil : Yeah. Yeah. Uh, let’s, let’s switch gears a little bit. Um, over the last few months, maybe a little, maybe further back than that, I have seen this huge rise in direct bookings and more and more folks like really sinking their teeth into it. I’m, I didn’t plan for this. I, I find it like very lucky in serendipitous that like we started the company when there’s this like, surge in demand.
Gil : But I, I’m interested in hearing whether or not that that’s the same on your side as, as kind of the, the PMS powering a lot of the back end of
Frank : Mm-hmm. Yeah, I mean, we’re seeing it as well. Definitely. Um, what we’re seeing is, um, more hosts are shifting their energy into getting more direct bookings. And a few years ago, um, it, it, it felt like a luxury really to get direct bookings, but now, in my opinion, I’m sure in yours as well, and a lot of property managers out there, it’s almost a necessity.
Frank : Um, and even like across our, our customer base, our direct bookings have been trending up. I would say year over year. And it’s usually the same formula of, you know, having a clean website. They, and we, you know, we partner with great, uh, people that provide that. Um, having the consistent branding and the automation and, you know, once those managers see it working, they’re gonna double down on direct bookings.
Frank : So we’ve, we’ve seen a huge uptick, especially, you know, with, you know, the OTAs, they, yes, sometimes they get a bad rep, but their, their visibility, you know, um, Airbnb, vrbo, they bring in the bookings. But if you want long-term success, uh, and higher margins at that direct bookings are the game changer in my opinion.
Frank : And you get those guests email, uh, you can remarket, you can upsell, you can build those relationships and you could actually create this sense of loyalty, which just kind of, you know, a nice little domino effect. Um, so I could see why. Direct bookings have been up year over year, and even back when I worked in, uh, the luxury hotel industry, one of the biggest takeaways for me personally coming into the short term rental field was how critical direct bookings were or now are.
Frank : Um, and the great thing is, my experience with hotels is that we just don’t want this, like heads in beds, approach, hotels want to own that guest relationship right from the very beginning that’s, it was ingrained in us. And I, again, I worked for the Ritz Carlton, the Four Seasons. Like that’s what they want.
Frank : You want that guest loyalty and that branding. And, and I mean that’s, that’s, that meant investing in our own, in our own website, um, our own strategies for optimizing, uh, booking flow. Just overall, just to make sure that the brand message stood out from the OTAs like Expedia Hotel tonight, like all of those.
Frank : Um, and now in the short term rental industry, it’s, it’s really not that different. It’s really similar, and like I said, Airbnb and vrbo, they bring in the bookings, but if you want to build long-term success, direct bookings definitely is key. Um, since we are talking about hotels though, like something I did learn, uh, about hotels and that just translates, um, perfectly, is the idea of experience over the transaction.
Frank : And I think a lot of property managers now, um, with all the webinars, the podcast, the, the help articles, the coaching, the thought leaders, um, it’s a huge focus on guest experience, uh, which helps me because in luxury hospitality, every touchpoint matters. So the tone of your email is huge, the way the room is presented, the check-in flow.
Frank : Uh, the experiences during the stay, that’s exactly what hosts need to think about too. It’s what sets them apart as much as the, um, as much as the short-term rental industry is saturated with property management softwares, the short-term rental market is saturated with short-term rentals. And you really have to set yourself apart from those and direct bookings only work if you’re offering that experience to guests that they want to come back to or even like, tell their friends and families about, you know, and
Gil : Absolutely. I, I think like, sorry to cut you off there, but like, I, I think like it’s, it’s a point worth doubling down on from all the property managers that we work with. The ones that are most successful in direct bookings are the ones that really care about the guest experience. And we’re not talking about just folks that have Superhost status or have five stars.
Gil : Like I think the, there’s a different. Mindset of folks that really care about hospitality. Those are the folks that are successful. Um, I know plenty of hosts that care about the five stars, and they’re really good at crafting out, uh, the, the guest message messaging to, to them to make sure that they get the five stars.
Gil : But then there’s almost also this like other caliber of hosts that really think through what do I want the guest to experience as they’re booking with us? What do I want them to hear from us when, right after the booking, x days prior to the booking, checking in, mid stay, checking on with them afterwards.
Gil : Like, there’s this, I don’t know if warmth is the right way to say it, or hospitality that goes into it. And when you put yourself in that mindset of being the host and you’re trying to service that guest as much as possible, they remember that they, and I think like. No matter how good your marketing is, if you aren’t delivering, and this is same, goes for software products as well too.
Gil : If you’re not delivering on what the expectation is and going above and beyond, there’s no way that you can get that guest to come back to you or that per that, that user to come back to you. And they’re not gonna speak to you. They’re not gonna waste their time and speak to you, to their friends and families.
Gil : But the hosts and property managers that really care about hospitality and can anticipate what the user’s thinking and really trying to figure out like, how do I give this person the best experience? They’re spending their, their dollars and staying with us. They’re spending their time. They can stay anywhere else, but how do we make sure that they enjoy their stay and possibly will wanna stay with us again?
Gil : Those are the ones that are really successful direct bookings.
Frank : Yeah. Yeah. And, and having your own story and your own brand and your own, um, just level of experience and how that translates to the guest is what gets you more direct bookings too. Um, and even like with software, you could do it with hostfully, but there’s also a lot of AI powered, um, messaging, uh, software that are out there, um, that, that kind of just execute that for you.
Frank : And if you have the right property management software and that integration with that specific, uh, messaging platform. It’s seamless, um, and you know, it, it, and it alleviates so much more time for you. So you can now focus on growth and how to market and all that stuff because all of that day-to-day conversations really just kind of take a back seat because you have a powered software that are doing it.
Gil : Yeah. Yeah, I’m, I’m a user of one of those AI tools that I believe the founders are a user of Hostfully
Frank : We’re thinking about the same ones. Yeah.
Gil : I think we’re saying think it, same one. And they actually, they use craft estates for their direct booking. So
Frank : Oh, sweet.
Gil : it’s, it’s quite interesting to see this kinda loop there. Um, and we’re, we’re always talking about like, how do we kind of work together?
Gil : And then I think that’s the powerful thing is like, not many folks realize this, but there’s a lot of conversations that are kind of behind the scenes of not just doing an API integration where two companies can now work together where this team is onboarding, but like work, having conversations with them and with you folks of like, actually, how do we upload all this?
Gil : Like, what are the new experiences that we wanna light up? And those, those to me, really excite me because I’m imagining like, how can we make it so that for instance, like we don’t, we don’t, we don’t do anything with your guidebooks right now. Like, I would love to figure out like, how do we elevate and take information that you have in your guidebooks to deliver.
Gil : An exceptional direct booking experience and bring that in back into it. Like, so that’s, those are the types of things that I’m thinking about. Um, and that happens beyond just reading API documentations.
Frank : Yeah. Yeah. No, and it’s, it’s, that’s, that’s the important part, especially with the short term rental, uh, space, is it’s saturated with property management software. Um, but then there is that opportunity to enhance guest experience with the digital guidebook. And there’s so much more to hostfully than just our property management software, as you know.
Frank : And you mentioned, uh, we provide the most underrated growth tool, in my opinion, in the short term rental space. And that’s the digital guidebook. And it can drastically transform operations and optimize and generate revenue. Um, we actually have one long term client. They’re, uh, I don’t know if you’ve heard of them, cabins for you.
Frank : Um, they’re a hospitality company that now manages over 350 cabins. Um. The, the, the great thing here is, and I pulled up their case study before our chat because it’s mind blowing what they’ve, what they’ve done, um, before they deployed host lys guidebook, their guest relations team was just drowning in those repetitive questions, like you said.
Frank : And they fielded about 12,000 in ball inbound calls monthly. And many of them were just simple requests that could have been answered via the guidebook. And then fortunately, they realized the strain that it was having on the staff, um, too much time was being spent answering the same things, just over and over again.
Frank : Uh, and that’s when they introduced the, the guidebooks. And in just one week, the team created 345 individual guidebooks, one for each property. Uh, and they designed these templates and these cards, that’s what we call them with arrival instructions. Your local attractions, your restaurant recommendations, like your house manual, and then roll them out across their portfolio.
Frank : Uh, and then I think their, um, inbound support calls drop dropped from like 12,000 to 10,000 per month. That’s a, that’s like a 15% reduction in like, what’s the wifi code? What’s the wifi code? You know? And then because of that, their revenues increased by 6% after implementing guidebooks because they were now able to focus on the problems that they were having in their business and not investing all their time on answering what’s the wifi code, you know?
Frank : So the step was, you know, the staff, the staff, uh, after that, I mean, they were obviously less burnt out ’cause fewer messages were coming in. Um, but ultimately it freed them up to handle the more complex tasks that you need to focus on growth. Um, so that’s kind of, it’s pretty cool to see a drop. Inquiries, but an increase in revenue simply by adding guidebooks.
Frank : Um, and then we also have, uh, talking, why not? Let’s talk about upsells. Um, with the guidebook, uh, we have a partnership with Via Tour. So if somebody books an attraction via the guidebook through, no, via via tour, through the guidebook, the property manager gets 8% of that purchase. So you could even use, um, the via tour partnership for upselling.
Frank : But then we also have something called the Marketplace in our guidebook, where you can literally sell a wine amenity, uh, you know, a pet amenity, uh, I don’t know what, whatever you upsell, you can do so via the marketplace.
Gil : Yeah, I’m very, as we’re talking, I didn’t intend this to be like a, like a product ideation session, but I would love to kind of bring some of that further up funnel into the direct booking flow because, and I’ve, I’ve talked to other upsell kind of providers there that focus solely on upsells, and that’s one of the things that we want to highlight in there is that it’s not just, you’re just booking the place to stay, but what else can we make sure that this is the right stay for you and this is the right place that you trust and, and want to want to basically have your verification with.
Gil : And I think upsell is actually part of really the conversion. Like it really helps also in selling and closing that stay as well too.
Frank : Yeah, no, it really does. And there’s, um, even with, because the, the guidebooks are a URL link, um, you can include it in all of your communication. So even in like your pre-arrival email, you want to include the guidebook, um, just so they get excited, like. Um, you can even have customized categories, like you have like restaurants and bars, like the usual, um, but you could have customized categories like beaches, wineries, lounges, hiking trails, coworking spaces.
Frank : Um, so there’s like a whole bunch that you can use specifically for your market. Um, but you are gonna really like this one is, um, with the guidebooks we have something called the splash screen feature and that asks the guest to agree to the terms to your property. Um, but once or after they agree to the terms, it prompts them to collect guest email addresses.
Frank : And that’s a critical loophole around OTA policies. Yes. You others are becoming a little bit more strict with those. Um, but it, you know, that’s, that, especially going, going back to cabins for you, that was a di direct line to market audience for direct bookings, uh, and their increase in seeing direct book.
Gil : Yeah, I think that just now, and I, I don’t know how far back some of these features goes, but I think it’s, I find it right now, it’s easier and easier to start to build your direct booking engine than it ever has before. And I, I, I think that over time it’s gonna get easier and easier for folks where they’re now able to build their own brand.
Gil : They’re able to deliver the level of service that they want, that attracts people to come back. And I think the folks that lean in on that and that really think of a hospitality the right way, those are gonna be the ones that’s gonna be really successful.
Frank : Oh yeah. Yeah, for sure.
Gil : Yeah. Um, what do you, what trends are you seeing nowadays that, and yeah. What trends are you seeing nowadays and kind of how do you see Hostly or yourself kind of evolving towards some of those trends?
Frank : Um, I mean, the trends that stick out the most. Direct bookings. Yes. Um, and just again, being on the partnership side and working, um, with influencers and partners, there’s a whole bunch of like, trends that are happening. Um, but it’s really what Hostly can do to execute what the guest ultimately needs. Um, so, you know, it’s, it’s, especially after like, um, our most recent funding, like we’re, we’re running, we’re expanding, uh, we just have, uh, so accounting comes up a lot.
Frank : Accounting’s boring, sorry, everyone loves accounting, but you know, we don’t get into this industry because we wanna run Excel sheets every day. Um, so that’s a huge focus on ours is, um, building like an accounting. We have an enhanced report feature where you can create your own enhanced report. And you can also automate those reports to run daily, weekly, or monthly.
Frank : Um, so that’s a huge focus of ours. Um, and definitely improving the accounting portion, especially here in North Carolina. Trust accounting is huge. Um, and I see a lot of that bleeding into other states, so I feel trust accounting is gonna be a huge focus, if not already. Um, but again, you know, we have one of the strongest APIs in the industry, so adding integrations that connect the tools to the host, uh, we’re already using.
Frank : Um, so we have that there. Um, AI features, yes. How can I forget? Direct booking. Above direct bookings, ai. Um, and you know, things like smarter messaging, pricing suggestions. Um, we now have hostfully devices, which is huge. Um, that’s been a really, we’ve, we’ve received so much good feedback on hostly devices, just ’cause it makes.
Frank : It’s just now centralized where the property manager can just do everything and automate everything directly within the property management software. Um, and even like pricing suggestions, uh, you know, we integrate with all of the dynamic pricing tools and we integrate with them well, where it feels as though they’re part of Hostly.
Frank : Um, our tech stack is probably one of the strongest that we offer. Um, and the goal, the goal ultimately with all the trends, with all the fads, um, it’s, it’s, it’s always the same. It’s just, it’s making more, it’s making hosting more sustainable and less stressful, just ’cause you, you know, you equate growth with stress.
Frank : It doesn’t have to be that way. Um, if you get the right software and the right features in place, you keep it sustainable and you’ll see this gradual growth.
Gil : Yeah, I, I, I, we have folks that want to build a direct booking website, and they’ll come to us and they’ll, we find out that they’re, they don’t use a PMS and they’re listed only on the OTAs directly, and maybe they’re using Icon links. And they asked me, can we build a website? And I’m like, no. Like, we don’t recommend getting into direct bookings if you don’t already have a PMS in place, because at that point, you don’t have one centralized way to make sure that you’re having the same pricing across all your different channels.
Gil : You’re not having to block off the calendars. If you get a booking on one channel over the others, or your direct bookings, like you wanna make sure that you don’t get a double booking on Airbnb, vrbo booking.com, like we wanna make sure that you can run this almost on autopilot, like we want. We want that to be very seamless.
Gil : So like we will really, like if someone is interested in having direct bookings, like we say, pretty much like, we can’t do it without a PMS, and these are the folks that we will recommend to you. And so we encourage them. But it’s also really surprising as you’re saying this, like how much folks still don’t have a PMS.
Gil : Like there’s actually a lot of folks, even outside of direct bookings, like maybe they’re not interested in direct bookings yet they’re getting started, that they’re still running everything directly on the OTAs themselves. I’m really surprised because there is a lot that goes on with the PMS and a lot of energy that puts into just really operating your entire short term rental business and how much A PMS.
Gil : Really pulls a lot of the repetitive of outta your way, where you’re really focusing on more of the exceptions than anything else. Like how do you continue to upscale and uplevel your stays, but you’re not really having to figure out like, did I message my guests? Did I block off the calendar? Did I price things correctly?
Gil : Like those, me as a host, I don’t think about any of those things at all, and I don’t know how people that are only on the OTAs are, are able to do it.
Frank : I know, and a part of me wants to say it’s like ignorance and know, and not knowing that there’s a software that can do that. Um, but I’ve met many, um, even like when we travel, uh, for conferences, we always stay at short-term rentals, and I find out that they have 20 short-term rentals and they’re only on Airbnb and all that stuff.
Frank : And I try to sell them hostfully, but they’re just, they don’t want it. I’m like, I don’t get it. I
Gil : They, they, they find ways around it. They’ll, they’ll, like, they’ll, I cal, they’ll, I cal their VRBO and Airbnb and vice versa, where they’re blocking off each
Frank : Yeah. But then they’re the first ones to complain about double bookings, right.
Gil : yeah, yeah, yeah. And then they’ll like connect their price labs directly to the OTAs, and it’s just like, I don’t know. I, I think there’s, there’s just a different way of looking at it, because then you have like one centralized place where you’re managing it all and you have like, almost like a god’s eye view of everything that that’s happening.
Gil : You know, what’s triggering what, if you have an inquiry and you wanna price it out, it’s very easy for you to do all that stuff. I, I, I, I came from a world where we launch our first property and luckily I had buddies around me that were already property managers, and so they taught me, and they’re like, Gil, you have to have a property management system in place.
Gil : Even on our first one, I was like, really? That seems really overkill. And no. They’re like, no, you need to have it in place. And I’m so glad that I did to the point where now I don’t know how other people do it.
Frank : Yeah. And I always say like, when we have the demos, um, with like a property manager that has one listing, I’m always. I, I praise them for looking into a software at that stage of their, you know, the, the beginning stages of their business. Because one of the worst things you could do is know about a property management software when you have one listing and not act on it and wait until you have like 10.
Frank : ’cause then once you have 10, you have 10 listings. You’re across the board in channels. You have a lot of history with guests. You have a lot of future guests. You have a lot of guest experience to deal with. You don’t have time to learn property management software. So if you have one, so if you have one listing, there’s no better time.
Frank : There really isn’t any better time than getting a property management software right from the get go because you can use that, that as you scale, you’re gonna learn the software better and better and better the more you use it. And then by the time you do have 10 listings. The last thing you need to do is learn a property management software and transition all that data over, you know, so I always commend and I, I I make sure that if they have 1, 2, 3 listings on demos, just to, you know, appreciate their, their insight and their want to look into a property management software.
Frank : And that’s also another thing with Hostly. Yes, it’s a daunting process to learn the software. Um, hopefully makes it easy because we have an easy UI and we’re fun to work with. But we provide onboarding sessions. We have office hours, so Monday through Friday, one hour per day, we have a real life dedicated onboarding manager there to answer any outstanding questions.
Frank : Um, then we transfer them over to our customer success manager and then our customer success manager takes them on and they have all of the stuff that they do with them. But that’s gonna be your customer success manager. Until your life ends with Hostly. Um, and the great thing is we saw such success with the onboarding office hours that the customer success team now has customer success office hours Monday through Friday, one hour a day.
Frank : Um, and it’s just an opportunity. If you, if you’re confused about the enhanced reporting, you jump on that meeting and you’re meeting with a real life person. So it’s, again, just going back to our support and our guidance with our users is key because yes, we, it’s in our business model. We want them to scale.
Frank : You know, we want you to grow, we want you to be successful. So you can talk about how awesome hostful it’s, you know, but it’s like, it’s stuff like that that, you know, it just, it makes sense to, to be there for your clients and for your customers.
Gil : Yeah, I, I think like one of the, maybe the key drivers to your success or hostly success is that you have built the system to accommodate for that gradual growth, and you built the systems kind of behind it. The customer service systems, the, the account, the, the account management systems. Also, not just the product side, but it allows people to grow because I think one of the most challenging things is you feeling like you’ve invested so much into your PMS and then.
Gil : You now have to graduate to something else and learn another new system and migrate everything. That’s a very daunting task. And I, I hear it every once in a while, actually, probably more often than ever, more recently that our folks are migrating different PMSs. I don’t honestly hear that many folks migrating off of Hostly.
Gil : I, I don’t remember even the last time I even heard of
Frank : That’s awesome. And I mean, full transparency, we are a software, people do get annoyed with us, but going back, it’s like they say that they want to cancel out of frustration because something happens, but we save them because we invest in them and we talk to them and we’re like, all right, if this is the issue, let’s talk about it because you can do this, this, and this to prevent that from happening.
Frank : And they’re like, I didn’t even know about that. And I’m like, well, that’s what we’re here for. So yes, there, there are, you know, there are issues that that transpire. And if any property management software sales person says that there, that they never encounter any issues, turn away, don’t look at them anymore.
Frank : Um, but, you know, and again, that’s what sets us apart is we have, we’ve significantly decreased our churn. After focusing heavily on customer success and support and of course our, our constant innovative approach to, to features and capabilities that Hostfully offers.
Gil : yeah, I believe it. I believe it. What, have you seen any feedback? So we, we’ve been integrated for a little while now. Um, I forgot how many months now since, since we’ve been integrated. Have you heard any feedback of folks either internally or from our customers of just like how the integration has gone or how the partnership has gone on your side?
Frank : Overall great. Um, they always talk about how fast it is, uh, and like how easy, how much easier it was than they thought, which was great. Um, and even just building, ’cause yes, you can, you can have a really robust website and there’s phenomenal website developers that are out there. Um, but the partnerships specifically, and I think if, if your listeners.
Frank : Your viewers haven’t noticed. We kind of have the same mindset to customer approach and success and just, um, just enhancing the guest experience with our software in general. That that’s what they see and that’s what they enjoy and, and it’s guiding them through it. And I think that’s the big thing with crafted stays is you are still onboarding.
Frank : You don’t have to be onboarding your new clients, but you choose to because you want to grow and you want crafted stays to grow. And what better way than actually onboarding your new users onto crafted stays? Um, so that’s, you know, that’s, that’s huge that you still do that. Um, and even I’m sure once you grow significantly, which I’m sure you will very soon too, and very faster than you, you might think.
Frank : Um, but I also think that you’re gonna keep that culture even when you stop. Having or having the privilege to onboard your new users. Um, so that’s kind of the feedback that I get is that, you know, it’s handholding guidance. You even, you even offer suggestions too, which is helpful. Um, offer like, you know, and I don’t wanna get into your pricing ’cause I’m like a sales guy on your end, but ultimately, you know, with, with what you offer is efficient and it’s sustainable and it’s, you know, you control over your business, which is great.
Frank : And that’s even like the mindset, the mindset shift.
Gil : yeah, I think like the, the, the culture, you’re, you’re absolutely right. Like, yes, I will get to a point where I, I won’t sustainably get to onboard and get to meet every single person, but you bet I will find some way to make sure that I don’t lose touch. Maybe it’s user voice or
Frank : Yeah, yeah. No surprise there. Yeah.
Gil : Um, but having been a product person for the last 15 years, I’ve learned that you cannot build product. Well, if you’re not constantly getting in front of customers, you, you just can’t. And I, I’ve learned that the hard way. I’ve learned that through my entire career of building out teams and finding out some of the product managers on my team, they hadn’t talked to a customer in three months and they’re working on a feature and they think, okay, we have to get to MVP, we have to build this out, we have to get this to market.
Gil : And over time I find that the really successful product managers, the one that builds the best products, the ones that get really good adoption, are the ones that are constantly on the calls. And I know that in corporate, when you’re building software for big Silicon Valley Tech, companie. It’s really hard to have that open channel of communication there.
Gil : But the prop, the product managers that are constantly talking to their go-to-market counterparts, their CSMs, their account reps, they’re getting feedback from them. They’re asking, can I jump on your sales calls? Customers having an issue, let me be there with you to help solve it. And those are the product managers that thrive and do really well.
Gil : So, like me as a product leader prior to building this company, that was my big thing, is building a culture where the product team was as connected to the go-to-market teams as much as possible. So you bet there will be a day that I cannot sustainably be on every single one of those customer calls, but I will not let customer service being in touch with the customers, feeling out like what the customers need that will never go away.
Frank : Yeah. And I mean, like I said, it’s completely feasible. We have over 150 associates, uh, at Hostfully now. And when it was just Margot and David and Steph and a few others, they were all doing it, but now they can anymore. But that culture is still there. That’s the feeling our clients still get is that, you know, we’re, we’re thriving and we’re growing with them.
Frank : Um, so I’m, I’m, you know, stoked that, you know, that the culture is continued to be as strong as it is even with our significant growth. Um, and that’s a huge priority for our CL like our executives. That’s, it’s keeping the culture is one of the biggest things for us. I,
Gil : Yeah,
Frank : because it translates, you know?
Gil : The customers will feel it. Customers don’t like they, they know when they’ve been sold something that may not fit them or they made a mistake. Um, or when something just feels right about the decision. Maybe it was the conversations, maybe it was the product demo. There’s a big difference between being sold something and feeling like, okay, I made the right choice.
Gil : And it’s usually embedded in culture more than anything else.
Frank : Yeah. It
Gil : And the same thing.
Frank : to be,
Gil : Same thing goes for hospitality.
Frank : I, I was just gonna say that. Yeah.
Gil : when a guest feels like you are really there to make sure that they had a really great experience and that you’re not just reaching for that five star review. There’s a difference.
Gil : It’s a very fine line in terms of like what you may see in the reviews themselves, but you’ll see it in their direct booking rates. You’ll see it in the repeat bookings. Like the ones that do really well are the ones that care about hospitality. And on the software side, the ones that care about the customers that are using the product.
Frank : Yeah. Yep. No, it tr it translates on both ends for sure.
Gil : Yeah. Well, Frank, I think that kind of leads us to like our last leg of the show where I asked you three questions. Um, first question, what’s a good book recommendation? I am always looking for a good book. So what do you, what do you have for me?
Frank : funny story. Um, I have two kids, so I don’t have time to read, but every time I see a book that gets recommended, I buy it with hopes of eventually reading it in my library with a martini.
Gil : of books?
Frank : Yeah, so I literally have, we bought, we literally have a bookshelf, we have a built-in, and it’s all books that I have yet to read, but I am making good concerted effort to read more.
Frank : My favorite book of all time is Frankenstein by Mary Shelley. I don’t know if you’ve read it yet, have you read it yet?
Gil : no, I haven’t.
Frank : so I highly recommend it, especially now it’s almost October. It might be a good time to read it. And also, Netflix is coming out with a movie. Um, in, I think it’s in November. Uh, highly recommend Frankenstein by Mary Shelley, but right now I am making a concerted effort to read more.
Frank : Uh, so I am reading, um, gosh, I promise, hold on. Lemme see. It’s called A Prayer for Owen Meany by John Irving. It was published in 1989, so it’s like one of the old, old ones. So I kind of, when I do read, I like to read a new book and then an old book, and I kind of go back and forth a little bit.
Gil : Yeah,
Frank : I’ll tell, I’ll send you, uh, I’ll send you a text of the bookshelf and you can
Gil : yeah, yeah, yeah, yeah. Yeah. I’ll scan, I’ll scan through. I’ll, I’ll, I’ll make passive judgments on,
Frank : yeah.
Gil : choices.
Frank : Hey, book talk is real.
Gil : Yeah. Um, second question, what’s one piece of mindset advice that you would give to someone that’s starting something completely new?
Frank : Ah, just baby steps. Keep it simple. Just there’s no need to put the cart before the horse. Just keep it simple and it kind of goes, even, not even for someone with a new business. I mean, obviously for new hosts, start small one action can make a big difference. Um, you know, like launching a direct booking site, send your first follow up email.
Frank : Don’t try to do everything at once. And I always say consistency beats complexity all the time. But then that question can also kind of go back to the seasoned managers. Um, and it’s mostly just shift the focus. Um, ’cause at that point it’s all about scaling smarter and not harder. You want to automate those repetitive tasks that you have every day.
Frank : You want to nurture your repeat guests. You wanna lean on data to refine pricing and just focus heavily on your marketing. Um, and again, I think, I, I think it’s just, it kind of goes across the board for new hosts and, and season managers is, the end goal is, is the same. It’s just not to have more work.
Frank : It’s not to burn, burn yourself out. You know, stress does not mean success. And it’s more efficiency, more sustainability, and ultimately just more control over your business. Uh, and you’re just gonna kind of skyrocket from there on in.
Gil : Yeah,
Frank : Keep it simple, folks.
Gil : Yeah, I remember the first ever version of Crafted Stays. I’m sorry for the first five customers that have been with us since the very beginning. Actually all five of them are still with
Frank : Hey, you go. Hey, that’s perfect.
Gil : I would say even the first 10, 12, maybe more, are still with us. Um, we have a very low churn rate, but our product.
Gil : It’s so different now than it was like 18, 18 months to two years ago. Like we didn’t have the template editor. You couldn’t make custom changes. You, it was just very bare bones. We didn’t even have the ability to pull information from the PMS, so you use widgets all the time. That was our first version, and the customers believed in us at that point, and we continually, over time have gotten better and better and better and
Frank: Mm-hmm.
Gil : to the point where like the early folks, like they’ve seen us move mountains on in terms of what we’ve done.
Gil : They’re like, what’s, what’s next for you guys? So it’s been amazing. It’s all like, like I said, it’s, it’s baby steps. It’s embarrassing to be honest in the very beginning. But had I not taken those steps, it would not have evolved to what it is today.
Frank : Yeah. And just going back to like the mind, the mindset shift is like, just take it day by day. Manage that day-to-day chaos because you have to manage the chaos day to day in order to build a long term and resilient operation and resilient product. Um, so day by day, keep it simple guys.
Gil : I love it. I love it. All right, Frank. Last question. What’s one tactical takeaway that you would give to someone that’s either getting started in direct bookings for the first time or trying to amplify their direct bookings?
Frank : there’s so many things you can do. Um, I think when it comes to direct bookings, one of the biggest lessons I’ve carried over from my time in the luxury hotel industry is that the fundamentals are the same, whether you’re running a five star hotel in New York City or a three bedroom short-term rental in, uh, Houston, Texas.
Frank : Um, the first thing is your website is everything. It’s your marketing. It’s your digital front door, and it has to be simple, clean. Mobile friendly. Um, and guests should be able to book it in about like one, two, max, three clicks. ’cause if the experience feels clunky or confusing, they’re gonna go book on Airbnb or vrbo.
Frank : Um, and that’s, that’s like the main thing ’cause it’s also your brand and that’s the first experience that guest has with you. Um, but then going back to keeping it simple is direct bookings aren’t one big push. It’s not one big move. They’re small intentional steps, um, that build on on one another. You know, start with your website, make it clear, make it trustworthy, then layer in the email marketing, then build in the discounts.
Frank : Just keep that relationship going. And then finally, you know, you can add the upsells. You can automate, you’re not stuck in the inbox. Um, and that’s really, you know, where tools like crafted stays, but Hostly also shines. Um, ’cause ultimately you do, yes, the direct booking. But then the other one I would say this is a close second, um, is practice building trust with your guests and your partnerships and your, you know, your strategic partnerships.
Frank : Um, again, going back and lastly I’ll end here, I tend to ramble, Gil, I told you, but in hotels, uh, branding and consistency did the heavy lifting. As long as you had a good brand and you were consistent with that brand, you were golden. Um, and in short term rentals that translates to professional photos. A transparent policy, transparent rental agreement, um, but also having the reviews and social proof is what convinces a guest to hand over their credit card on your, on your website instead of, you know, over to an OTA.
Frank : So there are a few things, but get your website. Website is number one. ’cause you can just share that with everyone and, and, and there’s that sense of, um, you get that like personal. Relationship with the host when you book direct?
Gil : Yeah. It’s funny, I, I, I, whenever I give this type of answer, I, I, I still also go to the same foundations there and almost like the, the step zero for me is make sure that you have a PMS because you cannot start without a PMS in place. Um, so it’s happy to, to hear that it’s a fast follow to, to having a, a nice, polished website.
Gil : And I think you mentioned like making it simple to book. That is why it took so long for us to launch our integration because. I have a, I have a very strict standard in terms of like what I, what experience I wanna deliver. And we tried out using the widgets, we tried out different methods. We’re like, this does not feel right.
Gil : Like this does not feel as seamless as we want to be integrated with. We don’t want someone, we don’t wanna just be another logo on we Hostfully marketplace. Like we want folks to have a really good experience and I’m glad we took the extra time to build a very seamless integration now where someone on mobile or desktop, they can search for properties, they can search for different dates and we’ll actually carry that date over.
Gil : We’re, and we were only able to do this because we decided not to use the widgets and we reverse engineer and we try to figure out like how do we make it possible where we can make that seamless experience And it’s, it’s beautiful. Afterwards it took work, but it’s beautiful now.
Frank : Yeah. Yeah. It’s all, it’s where you end. That’s where it’s,
Gil : Yeah. Well, Frank, it was a huge pleasure having you on.
Gil : Again. I’ve been wanting to have this conversation for a very long time now, and I really appreciate kind of the, the partnership that we’ve been building together. Um, it feels like we’ve been working on this, or we’re working together for a lot longer than I
Frank : I know. I, what do we, I feel like we’ve only known each other for like six months or something, right? Yeah.
Gil : Um, but yeah, it’s been, it’s been a great partnership. Um, just seeing the success stories on both sides, it’s been amazing. So I appreciate you, you and your team really helping in on that. Um, yeah, and thank you today.
Frank : feelings. Mutual. Yeah.
Gil : I appreciate that, and you sharing kind of like how hostly is, is different. I love hearing all the conversations about culture and the features and everything, but I think honestly like, it, it really goes back down to like the team and the culture and that’s, that’s what feels different on, on, on, on, on the receiving end of that side.
Gil : Um, so kudos to you and your team on everything you built, and congratulations on the 10 year anniversary. Congratulations on the new, new round of funding. So it’s, it’s looking great for you folks.
Frank : Ah, thank you. Yeah. Thanks so much for having me, Gil. Like you said, long time, long time coming, but I’m glad we got a date on the calendar and now. Here we are. We thought it was so far away. But, and also just thank you to everyone tuning in. Uh, I really do hope someone or everyone leaves with at least one actionable item that you can apply or apply to your business, uh, today.
Frank : ’cause it’s just that one simple change that you need to make in order to kind just continuously strive, uh, to be the best brand, the best short-term rental out there. Um, so just keep on chugging?
Gil : And you bet behind the scenes on the technology side, you, you have dedicated companies to make sure that you can grow.
Frank : Yeah. Yep. We’re here for you.
Gil : Yep. Awesome. Take it easy, Frank. I’ll see you at Vrma.
Frank : Yeah. See you in a couple of weeks, Gil. Thanks again for having me. Thank you everyone for tuning in. We’ll see you soon.