Social Media Marketing: The Power of Influencers in Vacation Rentals with Ben Wolff

Summary & Highlights

In the fast-changing world of vacation rentals, it’s important to stand out in a crowded market. We recently spoke with Ben Wolf, who has a fresh approach to using social media influencers and content creators to help unique, upscale vacation properties attract guests. Here are some key takeaways from our conversation that can benefit property owners and marketers.

The Power of Influencer Partnerships

One of the standout strategies Ben and his team employ is identifying the right influencers—not just those with the largest followings. By focusing on local micro-influencers who have engaged audiences, they create more authentic connections with potential guests. This targeted approach allows them to achieve remarkable returns, with top-tier influencer collaborations yielding 7-10x ROI on direct bookings, even with investment levels ranging from $1,500 to $3,500 per collaboration.

Quality Over Quantity

Ben emphasized the importance of influencer authenticity. The most valuable influencers are those who maintain a discerning selection process, promoting only properties they genuinely believe in. This builds trust and drives more meaningful engagement with their audiences, leading to higher booking rates.

Building a Robust In-House Team

To support their content-driven marketing strategy, Ben has developed a dedicated in-house team of 8-9 professionals, including videographers, editors, copywriters, and social media managers. This cohesive unit ensures that their messaging is consistent, engaging, and tailored to showcase the unique aspects of their vacation rentals.

Unlocking Direct Bookings

By implementing these influencer strategies, Ben’s team has successfully driven about 80% of their bookings directly, offering competitive pricing to OTAs like Airbnb. Interestingly, guests acquired through social media tend to be less price-sensitive, often opting for higher-value stays. This not only boosts profitability but also allows them to capture fees typically allocated to third-party platforms.

Content Creation Strategies

Standout Features

• Emphasize distinctive features (e.g., tree decks, hot tubs) to attract attention on social media.
• Use storytelling to share the journey of property renovation or development, building anticipation and engagement.

Engaging Narratives

• Incorporate storytelling elements in short-form content to create compelling narratives.
• Build tension and resolution in posts, such as revealing stunning views, to engage audiences more deeply.
• Mix high-production content with raw, user-generated content to make marketing feel more like an experience than an advertisement.

The Importance of Shareability

• Properties should have something Instagrammable, like unique architectural features or breathtaking views.
• Authentic, organic content resonates better with potential guests than overly polished ads, leading to higher engagement and shares.

Leveraging Email Marketing

• Capture emails through pop-ups on booking sites to maintain relationships with past and potential guests.
• Send regular newsletters to keep the audience informed and engaged, driving future bookings.

Navigating Advertising Challenges

• Ben’s team uses minimal paid ads but has seen success with boosted posts.
• Tracking and attribution in the vacation rental industry are challenging, highlighting the need for better integration and cross-domain tracking to assess marketing effectiveness.

Technology Solutions for Direct Bookings

• Importance of developing robust direct booking platforms that manage the entire booking process without relying on external widgets.
• Ensure seamless integration with payment providers and property management systems (PMS).

Mindset and Continuous Learning

• Embrace failure as a stepping stone to success and consider investing in expertise through agencies or consultants to accelerate growth.

• Newcomers to the industry should adopt a mindset of curiosity and learning.

Transcription

Gil: Hey folks. Welcome back to direct booking simplified, where we break down the strategies and tactics on how to win in direct bookings. On today’s show, I have Ben Wolff. Ben, welcome to the show.

Ben: Thanks Gil.

Gil: Yeah. Do you mind giving folks a kind of a brief introduction on who Ben is?

Ben: Sure. Yeah. I’m, I’m the co founder and creator of Onera, which is an upscale tree house hotel or tree house vacation rental community. Um, we have one location in Fredericksburg, uh, which is Texas wine country. And then we’re opening our second in Wimberley, which is, uh, also Texas Hill country with some incredible views.

Ben: Our new location has 28 units. Our first one had 11 and we’re expanding that actually to 35. So that’s opening up. Next year in May of 25. Um, and separately, I have a, another company called Awasi, which is a services company for unique stays, landscape hotels, um, very unique vacation rentals, and our whole shtick is helping people to drive a massive amount of bookings direct at very high rates.

Gil: Nice. Nice. Talk to me a little bit. What is a landscape hotel? What is that?

Ben: Yeah, it’s, it’s a hotel that is, is seamlessly integrated and blended into the natural environment. So typically we’re trying to find properties that have amazing views or topography or landscape, um, that, that really, you know, draw a guest in, and then we’re creating these one of a kind stays architecture and design that, you accentuates what’s already there with the natural landscape.

Gil: Nice. Nice. Do you, when you’re looking for these, are you looking at for any particular areas, any market specifically, or it’s more about like really finding the plots of land that that do well for these things? Like, how do you search for it?

Ben: two hours ideally and three hours at most from a major market or major markets ideally, right? So, um, Onero Fredericksburg and Onero Wimberly are both in the Texas Triangle. Um, we are within that radius from Dallas, Houston, Austin, and San Antonio.

Ben: So we get a lot of drive to traffic from those markets. Um, and, you know, but there’s tons of these markets across the country, right? Um, anywhere that’s, that’s kind of outside of a, a major metro that has people with disposable income and, and a sizable population is, is a good fit. And then you just need a piece of property that, Is so beautiful that when somebody goes there, they feel like autonomically compelled to whip out their phone and take a video or take a photo.

Ben: Um, just cause it’s, it’s that stunning and what we call shareable, right? If it compels you to do that, then it’s a shareable. Location or vis Vista or, um, uh, property.

Gil: Yeah. How did you get into the UniqueStays Landscape Hotel? Like, how did you transition from kind of like that being the smaller operator into what you’re doing today? What was that journey like?

Ben: Yeah. So I, I was actually, I think a mid sized operator, probably in the STR space. We had about 200 properties under management. We were in like 10 markets across the U S um, and that was all pre COVID, but most of our inventory, most of what we managed was city, you know, urban STRs. Um, and that. Really got shook up pretty hard, especially early COVID.

Ben: So that’s what really pushed me in the direction of doing something more outdoor, more experiential, more unique. There was already this trend of a lot of copycats in the STR space, you know, a lot of, um, sort of run of the mill inventory coming online with little differentiation. So, um, we saw that trend even before COVID, but when COVID hit, it really just kind of pushed me to take the leap and do something really unique and do something outdoor focused, which.

Ben: Was performing, you know, already really well in early COVID.

Gil: Yeah. You said we, did you have a team, a partner that you kind of, kind of progressed from doing your city SDRs now into this, or did you like, what was that evolution?

Ben: Yeah. So, um, with my original short term rental company, uh, my partner was John Cole. You know, we were partners since about 2015, 2016, kind of building up that company, and then I quit my job in 20. And that’s when we really kind of started taking it more seriously. And I took over as, as CEO and helped grow it from a handful of units under management to 200 in about 18 months.

Ben: So we really experienced rapid growth and, um, we also raised a small fund together that was the initial capital for Onera. Um, and I have a. In my new company, OASI, which is the services company and as well as really the marketing and social media engine behind a lot of these properties. Um, so I started that in 2021.

Ben: Um, and I started that with, uh, Jesse, um, calmly, who’s my co founder there and really runs our, our marketing and revenue management side of the business. Um, and it’s funny, I actually used to work for Jesse, um, even, even before I partnered up with John, uh, you know, he had a short term rental management company called sense day.

Ben: Back in like the early 20 teens, um, very early Airbnb days. And, and I was doing some business development for him and then what he saw, what I had done with Onera, he was interested in, you know, Hey, how can we kind of take this to the next level and create a services code that can, you know, really optimize these properties, basically.

Gil: Yeah, so when you first did an era, what was that? What was that journey like for you? Um, how did you come with the concept? How did you know this is like the right thing to do? Like, how did you kind of fall into that?

Ben: Yeah, it certainly evolved. And I’ve always been somebody who has got very high sense of urgency. And so we, we made decisions pretty quickly. We made plenty of mistakes. We tried to iterate and learn from them. Um, but you know, the initial concept was somewhat stemmed from this road trip that, that my wife and I had done around the Southwestern U S we visited like a dozen.

Ben: We visited like a dozen national parks over a six week period for our honeymoon in late 2019. Um, and we had all of these gaffes and issues with the RV, you know, like some, the, the filtration system would break and we had to drive four hours to the nearest dealership because you know, typical maintenance shop couldn’t fix it or one of our outdoor exterior compartments, the latch broke off.

Ben: So our stuff like flew onto the highway, these things that like really took away from these incredible. beautiful landscapes and, you know, sunrises we were waking up to and sunsets we were going to bed to in this like beautiful, um, free camping land called BLM land, which is close to a lot of the national parks.

Ben: Um, so I wanted to provide that type of experience of just, you know, getting away in nature, beautiful landscapes without all the friction of the RV issues that we had. So to me, it was like, let’s do something more upscale. And, um, a little bit more refined and sort of taking away that friction. So you can just enjoy, you know, your morning expresso with the sunrise in this enchanted forest.

Ben: Um, like we, we kind of crafted at Onera Fredericksburg.

Gil: That’s awesome. That’s awesome. And now you, it sounds like you also do like the services arm as well, too, where you’re extending some of the things that you do personally for your own portfolio to others as well. Can you talk a little bit about kind of how, how you got into that?

Ben: Sure. Yeah. I mean, it evolved pretty organically. So, um, we designed Onera Fredericksburg to be like very unique. Kind of inspiring stays that would jump off the page, really just an Airbnb. Um, and then we quickly found out that we were missing a big opportunity with Instagram and we had influencers and creators reaching out to us saying, Hey, we want to showcase your property.

Ben: We want to come out and promote it with a collaboration post or a giveaway or something like that. And so. Ended up working with an influencer that was very persistent and had a pretty robust, engaged following. Uh, so I, I put up a direct booking site, you know, had her come out, we did a collab and she generated, you know, 10, 000 to 15, 000 in direct bookings on her first post.

Ben: For, for just a free collab and then did the same thing again, 30 days later. And that was kind of all the, the initial testing I needed to say, there’s something here and we need to do more of this. So, uh, hosted, I don’t know, at least a dozen influencers over those next six to eight months, um, and continue to host influencers and creators today.

Ben: But the big one that I really delved into more deeply in 2023, uh, three was Creating our own organic, highly engaging content. So early on, it was, you know, we were posting static photos and effectively influencers and creators were the only video, you know, real content we were putting out. Um, but in 2023, tried to work with an agency and that, that kind of fell somewhat flat.

Ben: Um, they just, you know, they weren’t investing in the content. As much as you know, what I thought was needed and that’s really like the special sauce of social media. It’s like if you put out good content, then your accounts do well and people want to book with you, whether that’s through influencers or through your own stuff.

Ben: Um, but if you don’t put out good content, it’s like you just kind of have an account. It doesn’t really move the needle. Um, so we invested heavily in building that team in house. Um, and that team today is, it’s more than half of a WASI. We have, um, Eight, soon to be nine people on our content and marketing team.

Ben: And that is, you know, full time videographers, editing team, copywriters, you know, who handle on screen text and captions, social media managers, you know, influencer recruiters and managers. So it’s this whole, you know, team and suite that we now leverage for our own properties. And we’ve had so much success at our own properties that other, uh, People in the Unique Stays space, Landscape Hotel space, Glamping Resort space have asked us to, to help them.

Ben: And we’ve, we’ve achieved some pretty amazing results for, for those types of clients in the past three to six months.

Gil: Yeah, so, so what’s, how much are you still relying on the OTAs now or, or how much is it kind of built on, on your direct bookings now?

Ben: We’re about 80 percent direct. And that’s always the goal that what we’re trying to get our clients to. So it’s like, how do we get them on a path to 80 percent plus? And, and that’s by the way, at At price parity, we’re not discounting. I know a lot of people do that, you know, five, 10 percent discount past summer, all of the discount onto the guest in our case.

Ben: I mean, we’re investing pretty heavily in content in, in the, this storytelling, the, this engaging, you know, well produced content. And so, you know, we need to realize. That, um, the Delta between like what, you know, Airbnb fees would get, for example, and what we’re getting direct. So we, we priced the same across both and we’re effectively capturing, call it about 13 to 14%, um, because either way you’re going to have to pay a payment processing fee so that remaining, you know, fee from the OTA is going straight to our bottom line.

Gil: Yeah, I got it. So it’s less. It’s more so that you’re taking basically the fees that Airbnb would take and actually putting that towards marketing dollars for your own, your own direct booking engine.

Ben: And there, and there’s still savings. It’s not like it’s one to one, right? We wouldn’t necessarily do it. It was one to one, but you know, there’s still savings. And you’re more heavily investing oftentimes, like upfront in years one and maybe two, and then it even can go down from there, uh, in terms of spend, especially with influencers.

Ben: Like once you’ve built. Your account up and you, you’ve sort of tapped the local audience. You don’t have to rely as much on influencers. And once you have a massive library of your own content, you know, there’s less shoots that are required. Um, so that, that number does go down and you own the customer, right.

Ben: From beginning to end, you own their full experience. Um, you know, you, you get them into your funnel, you can retarget them, you know, try to get them to be repeat guests and all that. Um, and. You know, we find that the guests that we reach on Instagram and social media more broadly are much less price sensitive than an OTA guest, right?

Ben: And OTA guest is looking at a whole bunch of myriad of options with a different price points and they’re trying, what they’re solving for is value. Right. They want the most value for their money. Whereas a guest of ours that sees a reel on Instagram is emotionally charged by what we’re putting out. And, and it’s sort of in this mode of like, I have to have it.

Ben: And the pricing becomes much less relevant as long as they can afford it.

Gil: Got it. Do you see that also raising your ADRs because of that then?

Ben: We do. We have higher ADR, uh, direct than, um, on Airbnb and it’s not because we price higher. It’s just because those people are buying higher demand days, longer stays, you know, more weekend days, farther out, things like that.

Gil: That’s interesting. What have kind of, you now worked with dozens, if not hundreds of influencers at this point, what was some of the biggest learnings as you kind of evolved into kind of where you’re at right now?

Ben: Yeah. So it’s, it’s all about the right influencers. It’s, it’s not. Necessarily, you know, the biggest following, um, we’ve worked with people that were TV stars, for example, with like millions of followers that didn’t move the needle at all because they had no authority in the space. Maybe no authority in the local market.

Ben: And then we worked with other players that. You know, micro influencers, for example, like 10, 20, 30, 000 followers that actually drove value. You know, we got some followers from them. We got, you know, thousands in bookings. And then there’s kind of the upper echelon of influencers that we’ve kind of found in pretty much every market in Texas.

Ben: There’s like. You know, a handful of them in central Texas that are really, really good and just drive a ton of value. And usually those are paid. All the other micro influencers is comp stay and you know, it’s typically free. Um, but those really, really good ones are going to charge anywhere from like 1500 to 3, 500 per collab.

Ben: Um, but you know, you’ll see a bump of 10, 15, even upwards of like 30 or 40, 30 or 40, 000 in direct bookings. So the ROI is, is there and justifies it.

Gil: Well, you’re telling me that you have a 10 X, 10 X ROI on, on some of these micro influencers.

Ben: The better ones. Well, the better one. So I would say the micro influencers, I mean, the micro influencers, the micro influencers, it’s right. Cause we’re typically not paying them anything. If you want to account for the cost of cleaning and maybe the, the, you know, um, opportunity cost of the stay then like, I’m sure it’s 10 X.

Ben: But what’s really interesting is the ones that you can pay 1500 to 3, 500 and generate, you know, 10 to 40, 000 in bookings. That’s what’s really interesting. And yes, those influencers, some of the best in market, we typically see anywhere from a seven to 10 plus return on investment

Gil: And why do you think those influencers work so, so effectively?

Ben: because they’re really good. They, they, they put out really good content. And the, their audience trusts them, right? Like there’s this inherent trust and genuineness and like, they’re actually in market. They actually care about this stuff. You know, some of these influencers, um, and they actually like to be called creators.

Ben: So let’s say creators, um, there are some of like my harshest critics, right? Like, you know, they’ll give amazing feedback, tell us how we can improve. You know, I’m, I’m always like, Trying to make sure that everything’s as perfect as possible for some of these creators because they’re, they’re so discerning and they’re, they’re as much, if not more about their followers than they are about you as a host, that’s your, your client, right?

Ben: Um, because they know if, if they sort of abandon or degrade the trust with their user base, then, then they can’t drive the same engagement. So they want to make sure that. Every property that they’re repping and posting about, et cetera, is actually worthy of going and is, is actually a value add to their, um, audience.

Gil: Got it. 

Gil: Got it. So, so when you’re working with a new client, that’s probably in a different market with a different influencer base, like how do you search and find the right influencer to work with? Silence.

Ben: is the audience and really what that comes down to is like, what kind of authority do you have in the travel space typically is, is what we’re looking for. Um, and then what’s your engagement. So travel influencers are obvious foodie influencers are also typically good because they’re still in hospitality and and if you’re trusting somebody when it comes to a restaurant, you may, You know, uh, expand that until something like a hotel or something like an Airbnb or a stay.

Ben: So we see decent crossover there. Um, but like a TV star or a fitness influencer or something like that might not be the best fit, you know, wellness, for example, could be one. That was good. It just depends on what their content is. You want to look to, is the content more about. The person or the property, right?

Ben: Or the product that they’re, they’re showing off, right? If it’s more like, look at me, me, me. Typically, we see less conversion from that than we do if it’s somebody who’s really showcasing the stay. Um, and you know, one of the top performing influencers in our area. You almost never see her face on camera and in her reels, you might see, you know, the back of her head or her walking or a friend of hers, but they’re not the, what I call primary character of the video.

Ben: Um, the primary character is the stay is the experience that they’re trying to show off and showcase. So that’s on the authority side. And then when it comes to engagement, you know, you don’t want somebody with a million followers that’s consistently pumping out, you know, 10 view videos, right? That’s pretty low engagement for, for, um, you know, somebody that is, is consistently putting out content.

Ben: I mean, we’re looking for. Usually minimum of 5 percent engagement. Um, and we might go as low as like two to 3 percent if it’s a lower demand day and it’s just a comp stay or something like that. But for somebody who we’re paying, you know, thousands of dollars, we want to see them have 5 percent plus engagement and also be a targeted authority in travel.

Gil: I got it. I suspect that because your properties are so unique, um, so kind of one of a kind that is a lot easier for you to market those and really bring in the right influences and also bring in the right engagements. Do you find this as applicable to folks that do not have unique stays?

Ben: No, I don’t. Um, so I, I think you do need to have something that, that is going to be engaging, is going to be highly shareable. Um, You know, it doesn’t have to be a tree house. It doesn’t have to be this crazy design stay or these amazing views. You know, we just took on this client in, uh, Indio that has a massive lazy river in the backyard and it’s this 10 bedroom compound.

Ben: So there’s something there that’s shareable, that’s unique, that kind of pops off the page that we think is going to do very well and play very well on social. So. You do need something with your property that is Instagrammable, right? If it’s a normal house, you got to add this insane deck with kind of, you know, lofted tree deck options and hot tubs and saunas.

Ben: You got to do something that’s going to bring people in and make your property really stand out. Um, so I think that’s a part of it. Um, You can try to do it with things like creating characters or personas, um, using humor. You know, I think Ryan air is a good example of that, that I, that I often use where, you know, the product isn’t that Instagramable or interesting, but they have built this whole like persona that, that really relies a lot on humor to create the engagement.

Ben: So you need some sort of shtick that’s going to pull people in and keep them engaged.

Gil: Got it. Got it. Um, and I remember when we chatted and one of our other like kind of walking talks, you talked a little bit about, uh, for some folks, even storytelling can kind of go a long way and kind of the journey there. Can you talk a little bit about that here?

Ben: Yeah, of course. So, you know, I think that relates to the whole building and public side of things as well, where even if it’s maybe like your more typical, well amenitized home, you can make it engaging by showing somebody the journey from purchasing or building, you know, as it may be renovating kind of like the, the struggle and challenge associated with that.

Ben: And then ultimately the final product and overcoming those challenges. That’s, that’s pretty much what a story is, right? It’s some sort of like. Some sort of conflict and challenge and then ultimately overcoming that. And that’s, that creates a very engaging story that, that people can buy into. Um, so it’s a way to build an audience and build a fan base, even before you open a short term rental.

Ben: I think there’s, there’s a lot of examples of that. Devin Lurup is probably the most kind of famous, big example of that. I think amassed a million followers, uh, over, you know, creating his container homestay and showing the whole build process and, and really building it. In public the entire way. Another component of storytelling that I want to speak to.

Ben: And I think storytelling really permeates through all of this, right? When we’re creating engaging content, it’s about creating a story. It’s not going to be as robust of a challenge or conflict as maybe Devin had when he was, you know, trying to cut out windows on his container home and, you know, You know, uh, trying to make sure they didn’t fall on the other contract workers, but you can still create that tension and conflict with the entry walk up to a unit or, you know, walking out and down around into like a hot tub area, or you can still create some of that, you know, um, challenging conflict and then like the, wow, amazing moment at the end.

Ben: Um, so there’s ways to do that, you know, with, with any, any real four year property. And then the big thing is. We, we really try to avoid making our content feel like it’s an ad and advertisement people, people pay a lot of money to avoid ads nowadays. And they kind of are repelled and repulsed by them. So the more something can feel organic and genuine, and even in, and even in some cases like less produced, um, it can perform better on social media.

Ben: So you don’t want to just stick to these like overly cinematic. Kind of slow pan hero shots because it feels like an ad. You want to have a mix of those with more, you know, UGC feeling raw content.

Gil: so you spent a lot of efforts, um, on kind of the social media side, you mentioned a little bit about retargeting. Um, what are some of the things that you do kind of outside of social media to really drive up to that 80, 85 percent direct booking rate?

Ben: Yeah. So email is a big one. I mean, we’re, we’re pulling in. Um, usually we have a pop up on our direct booking websites that helps to capture emails. Um, and that’ll bring anywhere from a couple hundred to even upwards of a thousand emails a week that we’re adding to our list. We’re sending out a newsletter on a weekly basis that, you know, is hopefully adding value, talking about what’s going on in the local region, maybe talking about new properties.

Ben: We’re opening, um, new experiences we’re offering, things like that. Um, so we can kind of farm that over time and remind people about us. Um, so there there’s that. And then there’s also, you know, all of our a hundred thousand plus followers on social media. Who were putting out reels and stories and all that on a weekly basis, kind of keeping us top of mind.

Ben: So even if, you know, they might’ve followed us last year and not gotten around to it or not had the money or whatever to come stay with us, but we’re, we’re continually reminding them every week and we’re popping up in their feed. So when they think about that next getaway, we’re top of mind.

Gil: Do you guys do any ads as well?

Ben: So minimal ads at this point, um, we we’ve, we’ve played with it a little bit. I mean, we are good on the content side, so that gives us a leg up when it comes to paid media, so we can repurpose a proven good piece of content into an ad or into like a, you know, just a boosted post. And we’ve done some of that.

Ben: We’ve definitely seen, you know, had some success there, but. There’s always issues with tracking and booking engines. And, you know, we, we’ve talked a lot about this. We actually shifted our booking engine in the name of trying to get better tracking so that we could have, you know, better, um, information when it came to creating ads and trying to, you know, get better performance there.

Ben: And, uh, And in the name of better tracking, we actually ended up with worse conversions and a worse booking site. Um, so now we’re potentially reverting back and having to just deal with the, the limited tracking or do more custom work to get better tracking. So it’s a whole rabbit hole and it’s not as easy as like a Shopify, right?

Ben: Where you’re, when you’re doing like more of a typical e commerce product, that’s really built. And for tracking, um, typically we’re not seeing that with vacation rentals or with, you know, independent hotels. It’s, it’s much harder to get true attribution and true conversion data.

Gil: Yeah, I definitely want to talk a little bit about kind of the things that you were trying to strive towards and what was like the stumbling blocks along the way.

Ben: Yeah. Yeah. So on the, on the ad side of things, I mean, we’ve, You know, I’m not going to get too, too much into the technical details of that, but I will tell you that we have, we’ve done boosted posts, which as you know, it’s like the targeting isn’t going to be as robust. Like you just can’t do as much with a boosted post.

Ben: You’re kind of just trying to get broader reach with a piece of content that’s already done pretty well. And we’ve had success with that. Like we’ve turned a video that, you know, had. Maybe it would have had half a million, uh, views into like 2 million from boosting it with like not that much dollars. So we’ll get, you know, more followers.

Ben: We’ll get, you know, maybe some conversions, but again, it’s hard, at least with the booking engines that we’ve had, it’s been very hard to track actual revenue and actual bookings. Um, we can track traffic, guesstimate. You know, with our conversion rate, how much we’re, you know, what our return is, what our row as is, but it’s, it’s hard.

Ben: It’s not, you know, this, uh, organic post or this specific boosted post produced this much revenue. Um, and we’ve run some ad campaigns, but run into the same issue with the booking engine. So we’re, we’re working through that now. And frankly, like it hasn’t been solved yet. I just talked to a new ad agency today.

Ben: That’s, you know, supposedly had a lot of success. They mentioned the same thing, like even, you know, for them, um, they’ve won awards in the space and done really well, but like even they sometimes are doing it based on traffic and then having to kind of, you know, use, uh, estimations to get to actual conversions looking at, you know, broader conversion rates.

Ben: So there’s not an easy solve. Um, I think we need a Shopify for direct bookings. I know we’ve talked about this quite a bit. I know you’ve been working on that, but, um, I haven’t seen anything that’s like. Truly delivering on it yet, but, but we haven’t tried your product yet either. So we’d love to hear your thoughts on it too.

Gil: yeah, I think one of the challenges that I see is that. And we’re, we’re trying to peel away from some of this right now is that at least in like the STR side, a lot of the PMSs that we use, or we partner with, they’ll have booking widgets, basically that you can plop in there, uh, which is really good to stand up a site.

Gil: And you can even build your site off of like Wix some of those things. But as you mentioned, you lose a lot of trackability because of that, because what you’re happening is like, Part of the traffic is actually going through the website that you know, yep. Uh, and then the other, the other side is on the PMS side and you really don’t have a great way to tie the two back together.

Gil: And if you’re talking about someone that’s lining on your homepage, for instance, and then they’re going through clicking to the property detail page and going through the booking flow. We actually have no way of knowing, uh, kind of out of the box. If they’ve actually converted, and it sounds like you’ve actually tried to do this a few times over and you’re still having some of these challenges as well, too.

Gil: So like, there’s like no easy solve for some of these things.

Ben: have yet to find somebody in the space that has been able to like, in a very simple way, explain to me how it’s actually working on their side. And most people it’s kind of like throw the hands up. We’re, we’re doing the best we can with attribution, but it’s, it’s not perfect. And like, we, the honest answer is we don’t know.

Ben: And there’s a lot of guessing.

Gil: Yeah, we tried on our side. We do this with one of some of our like PMS partners is that we’ll do like cross domain, uh, tracking as well, too. So what we ended up doing is With some of our PMS partners, we will actually tell them back basically the ID of the person that’s visiting the site. They’ll store on their side and they’re, they’re sending the tracking events back with that ID.

Gil: And that allows us to basically say like, this is the same person that started. on the booking web page. And this is the person that started the checkout page and married them two together. But it’s still pretty difficult. Like if someone has cookies turned off or whatnot, like you actually start to lose some of that traceability there.

Gil: Um, what we started to move towards kind of like back to like your Shopify for, for short term rentals, like that’s exactly like the, the inspiration that I have for this company is really to create A really well performing direct booking site, but also a platform that allows you to extend into that as well, too.

Gil: But one of the things that we’re trying to do is actually not use any of the widgets altogether. So we’re actually integrating back into the payment providers ourselves on on the back end side of things, where most folks will kind of like drop off and they say, this is the PMS his job now at this point, but you’re like starting from the homepage all the way to the very end on one platform, it’s a lot more work on our side to make that possible.

Gil: But when you’re talking about high conversion, being able to figure out and test certain things and see what works, if you don’t really know what the start state and what the end state is. You’re not going to be able to know, like, whether or not you’re moving the right needle. Um, so it’s probably going to be a long project for us, but we’re, we’re really like keen to work with the PMS partners so I can remove, remove the, kind of the reliance on just the widgets itself and the checkout flows.

Ben: Look, I mean, if you guys can solve it and crack it, I mean, you definitely have a customer over here. I’m sure there’s plenty of people out there too, that are, you know, focused on and trying to drive direct bookings that have experienced the same pain. I mean, I’ve heard this pain from not just vacation rental folks, but.

Ben: All the independent hoteliers out there, right? I mean, you have the big brands have have, you know, tons of dollars to throw it tech. And, you know, they’ve kind of got it dialed in, but it’s all custom. Whereas if you’re a smaller independent hotel, same thing as a vacation rental, you typically don’t have the resources to do all the custom work required to get good tracking.

Ben: Um, and You know, to improve your conversion. So what we care about as operators, you know, obviously is conversion and tracking. Um, so if you can kind of solve those two things, then I think you’ll have a, a very loyal, happy customer base.

Gil: Yeah, I hadn’t thought that much about hotels, uh, quite until I had our walking conversation. Um, and you got me thinking about like, should we have a arm of our product that is like geared towards more hotels where the temples are a little bit different, but because like, for instance, like hotels, you have more rooms rather

Ben: Room type. Yep.

Gil: Exactly. Exactly. Rather than unique, like property addresses and so on. So the way that you do, you display the properties and how you make search available is a little bit different. Um, but yeah, you got me, you definitely got me thinking.

Ben: that’s the primary thing. I mean, I think the other one is, um, which may be crossing over into PMS land, but, um, you know, cleaning fees versus not kind of how you bake in fees, whether you can do like, you know, set dollar additions that kind of reflect in the full price, as well as percentage differences across channels.

Ben: It’s things like that, that may differ a little bit between vacation rentals and hotels as well. Um, but yeah, I think there’s a really big market on both sides. So, um, yeah.

Gil: That that side I’m actually a little bit less concerned on because with all of our PMS partners, we try not to store the rates and do the calculations on our side because there’s actually a lot of math that goes into it and a lot of rules and logic that goes into it. So anytime someone starts a search for available properties or they start the checkout flow, we actually call the APIs dynamically.

Gil: Um, and it allows us to get the freshest data and make sure that we’re like not booking a date or a stay that’s already taken up. Yeah. I definitely hear you on that. Yeah. I, I’d be happy to, to collaborate a little bit more once we kind of get through this next few phases. We’re, we’re working on, we’ve been working on some, some big things recently, which we actually just,

Gil: Um, and yeah, we’re trying to figure out like, where do we spend a good chunk of our time? The Q4, Q1 of next year.

Ben: Nice. And I’ll just tell you in terms of PMSs and folks that would, you know, matter to us from an integration standpoint, uh, I would say cloud beds on the hotel side, host away on the STR side and, um, track to some extent on the STR and hotel side. So those are the ones that like either our clients are using or we’re using.

Ben: And so, um, if, if there was integrations with them, with your direct booking engine, and you solved a lot of our issues, I think that, like I said, we’d be a, uh, a willing participant.

Gil: Yeah. 

Gil: Yeah. We don’t have cloud beds in track yet, but we definitely, we’re, we’re, we’re good partners with the host away. Um, well maybe, maybe we’ll talk a little bit more, more about that. Um, then I usually end the, Uh, our series with, uh, two questions that I like to ask hosts, um, one is a mindset question.

Gil: The other one’s an action question, uh, on the mindset one first, what’s that one piece of mindset advice that you would give to someone that’s starting something completely new?

Ben: I mean, I think it’s kind of obvious you got to be okay being a beginner, right. And just soaking up that information and, you know, being okay to fail and iterate. Right. You know, the, the, the more you’re failing upfront, you’re still learning, right. It’s not, it’s not necessarily a negative. Um, so it takes grit and sort of a curiosity that like every failure is a learning.

Ben: Um, so I think that’s, that’s a big piece, right. It’s just being okay, being a beginner and then paying for expertise. You know, I’ve. There’s been so many times where I’ve hired an agency or a consultant or someone like that, and sometimes it works out longterm and sometimes it’s just a great, you know, crash course for, for a few months while we’re trying to get up to speed.

Ben: So, um, I think being willing to, uh, to pay for expertise and being okay to, to be a beginner and being curious and not afraid to fail.

Gil: That’s awesome. That’s awesome. All right. Uh, on the action question, what’s that one big, like tactical takeaway that you want folks to, to get from, from the show?

Ben: Design stuff that’s well made for social, and then you can really optimize by producing really good content and driving bookings direct. So I think, you know, Gail, you had a good point. Like, will this work for more commodity product? And I think it’s really hard. So design stuff that’s not commodity commodity products, right?

Ben: It’s going to show better on Airbnb and whether that’s amenities or design or landscape location, whatever it is. You need your property to stand out.

Gil: That’s awesome. 

Gil: Um, well, Ben, what projects are you working on right now that you want to engage with our listeners on?

Ben: Yeah. So a Wasi, our services company is, is rapidly exploding given our success on the marketing and social and driving bookings, direct side of things. So, you know, we’re, we’re growing that business. We’re scaling that team. Um, so if anybody is, you know, uh, uh, creative out there on that side of things, understands, you know, content, uh, videography, you know, Copywriting, anything along those lines that certainly reach out, we’re always building the team and the same thing when it comes to.

Ben: Customers. If you have a unique stay property, a landscape hotel, a highly unique vacation rental, you know, reach out. We’d love to, to market and we, we do management as well. So if somebody’s in need of more than just the marketing side, we have a management division. Um, and outside of a Wasi, um, I’m working on my next landscape hotel development.

Ben: Um, it’s in very early stages. So. Looking for investors, partners, you know, people like that. So if you like Onera, if you like experiential hospitality and are interested in real estate investing and development, uh, you can reach out on that front. Happy to explore.

Gil: Awesome. 

Gil: Well, Ben, where can folks get ahold of you if they’re interested in working with you partnering with you?

Ben: Yeah. So I’m pretty active on LinkedIn. Uh, so you can find me Ben Wolff, two Fs on there. I post a lot of educational content. If you just kind of want to try to pick my brain via LinkedIn, um, have a newsletter as well, where we’re, you know, putting out educational content every week. Okay. Um, and then we just started kind of getting going with my personal Instagram.

Ben: So it’s, it’s not as robust as LinkedIn yet, but there’s a lot of good stuff on there. It’s just, you know, my account’s not as big yet. Um, so that’s a, at I am Ben Wolff, two Fs on Instagram.

Gil: Awesome. Well, Ben, it was really good to have you on the show. Uh, definitely an expert in social media, social media marketing as well too. So I’m really delighted to be able to pick your brain, uh, for our listeners here today. I appreciate it.

Ben: Thanks Gil.

Gil: All right. Thanks. Bye.