[00:02:43] Ben Wolff: They’re looking for something that’s more of a unique experience that inspires them that. Really draws them in and connects them also to the the local vibe as well. So we just think this whole idea of experiential stays. And another aspect of that too, we don’t think the modern traveler cares as much about, let’s say, onsite staff, for example, or a check-in desk.

[00:03:06] Ben Wolff: There’s things they don’t care about and things they do. High design architecture, Instagrammable, creating a story and a vibe, something that’s very unique and experiential. We think they care about all those things, like tech enablement is another one. But then things like having the same room no matter where they go, and the exact same amenity stack and the same bed, and we don’t think they care as much about those things.

[00:03:28] Ben Wolff: Or the turndown service or the check-in desk person or people like that. So, We’re really just trying to focus on what we think the modern traveler cares about and wants and sort of get rid of all the rest we are going to get. 

[00:03:40] Patrick Donley: I Want to definitely want to get into the different projects that you’ve done.

[00:03:43] Patrick Donley: ’cause they’re super fascinating. Yeah. They look like they’re from a cover of Dwell Magazine, but talk to me a little bit just about how the inspiration for all this came about. How did you get the passion to start to do this? 

[00:03:54] Ben Wolff: So, I mean I’ve always been interested in real estate, so there’s always been that aspect to me.

[00:03:59] Ben Wolff: I actually found out I forgot I had done this when I was a little kid. I did this like dream home project when I was like 10 or 11, basically working like an early version of CAD and creating this whole like dream house. So I think it’s been a bit in my blood and something I’ve just been interested in for a long time.

[00:04:15] Ben Wolff: Specifically unique stays and Airbnb, STR I can tell you. So I had built up an Airbnb management portfolio. We had some units that were, we were doing lease arbitrage. I had some units that I was just doing third party management for. I actually quit my software sales job in April of 2018 to build up that company full-time.

[00:04:37] Ben Wolff: And I built it from we had a handful, eight to 10 units or something like that under management, most of which we controlled the lease for. And I built that up to a couple hundred units and by the end of 2019, so scaled that, figured out how to build that operation offshore call center in the Philippines.

[00:04:55] Ben Wolff: Local ground teams that were third party contractors in every market that we had really good relationships with. I was doing the revenue management myself with some help from the Philippines offshore team as well. And then at some point in there I got married and I realized I couldn’t be on my phone dealing with guest BSS at my wedding.

[00:05:15] Ben Wolff: So I hired my first GM and it’s like the best, it was the best thing I ever did. And recently did that at my new company Oasis as well. And it’s always amazing to do that. So I started with short-term rental, Airbnb management, grew that company through 2019. Was that the company called Blink?

[00:05:33] Ben Wolff: It was, yeah. Blink Hospitality. Yep. With my partner in that endeavor was John Cole. And then Covid hit, and ironically enough, we were actually in the Philippines having this like yay rah event with our offshore team. It was the first time we’d gone over there, we got this big villa. And I think while we were there, Trump closed the border from like Europe flying into the US and just halted travel.

[00:05:57] Ben Wolff: Almost all of our bookings got canceled overnight. I mean, it was like a movie. It was insane. Were 

[00:06:02] Patrick Donley: you able to get back to the us or how long did it take you? 

[00:06:06] Ben Wolff: My it’s the sort of subject of my wife. I don’t, ’cause like when I was going over there I was like, oh, like there’s like one case in the Philippines.

[00:06:13] Ben Wolff: It’s fine. And it wasn’t fine after I got there, flew to Bora Kai, they like shut the border, or no, they closed the Mandila airport like the day. Two days after I flew to Boraca, which is this like really nice island beach in the Philippines. So then like me and my partner ended up flying to Bali and we were able to like get out from there, but it was like by the skin of my teeth and Ill-advised.

[00:06:36] Ben Wolff: So we, we made it back, but all of our bookings got decimated and. We just were trying to survive, right? We were just trying to get back to break even fill units, long term, get outta leases. I think we were doing it the right way with landlords, which they were scared to ’cause people weren’t paying. So we were able to come to some good kind of mutually beneficial situations where it’s like, okay, charge us half rent for the next year, or we figured out how to make it work.

[00:07:01] Ben Wolff: But around that time we also started thinking about what else can we do? What is actually working right now? And I had already been turned onto this whole idea of unique stays, glamping, alternative accommodations. I think, you know that guy you were talking about earlier, Jesse, my partner and revenue manager now in Oasi.

[00:07:18] Ben Wolff: He had his compound out in Joshua Tree. Had like a converted bus, an Airstream converted garage. He had a plane that was no longer in service, but it was just kinda like an art sculpture on the property. And I had seen this and I saw the numbers he was doing and it was pretty exciting.

[00:07:35] Ben Wolff: Me and my wife had done this RV trip around the Southwestern us. And just reconnected with the great outdoors and I feel like there was a lot of that going on. Obviously that accelerated during Covid. So it all just pushed me in this direction of what became Onera. So me and my partner John, decided to raise a real estate fund, so not get out of just doing management and actually get into real estate investing.

[00:07:59] Ben Wolff: Initially that was going to be more of a rental arbitrage fund with some kind of glamping mixed in. Then the glamping just became, it started doing so well that we decided to do more and more of that and really just focus on unique stays with our fund. So yeah, that all pushed me in the direction of building on, started looking at land in the Texas Hill country and yeah, we can get into more of that, but that’s what pushed me in that direction.

[00:08:27] Patrick Donley: Did you wind blink down? Did you had, what? 200 properties under management? Did you wind that down as you were starting up this new fund in Onera? 

[00:08:36] Ben Wolff: We didn’t wind it down. And largely, I mean, thankfully I had built a team that allowed me to be much more passive at that point. So my GM was largely running that with our offshore Philippines team.

[00:08:48] Ben Wolff: I had not spoken to I and irate guests since six months before my wedding, which was amazing. So yeah, that was pretty passive for me, and I could focus all my energy on the fund and building up Onera. 

[00:08:59] Patrick Donley: So I wanted to hear about that first acquisition. You said it was in Texas Hill Country. Talk to us about that, how you located it, what kind of the parameters you were looking at for land acquisition.

[00:09:11] Ben Wolff: Yeah, so it sort of started with. I want to find a market within a few hours driving distance of where I live, ideally closer to my first big development project. I wanted to be able to be there often. I think at the time I think my wife was pregnant or became pregnant, sort of in the middle of my search.

[00:09:29] Ben Wolff: So I knew I wanted to be a little closer to home, but still be able to have eyes on the projects. And I identified three markets really within like a couple hours of Austin that I was trying to find a market where these like studio or one bedroom units that were a little unique or very unique were doing these insane numbers, right?

[00:09:52] Ben Wolff: A zero or one bedroom couples unit was doing a hundred thousand a year or $150,000 a year or something like that. Those kind of numbers got me excited. Then also how cool was the unit? Like if the unit was just amazing, whatever. Then it felt like they had optimized. But if it, the unit was cool, but I thought I could do something even better, and they were already doing a hundred thousand dollars a year.

[00:10:15] Ben Wolff: I figured that there was additional revenue that I could create there. So that led me to Dripping Springs Fredericksburg in Wimberley. Fredericksburg was the highest performing one at the time. Or actually Fred’s free and wimberley were both like neck and neck for the highest performing.

[00:10:31] Ben Wolff: I think we got one property action under our contract in Dripping Springs. Initially we did due diligence on that. Probably spent 10 grand. Come to find out the deeded restrictions wouldn’t allow for it. So that was a good like learning experience, right? I mean, I was new and very green to development, so I didn’t, and haven’t made that mistake again, that’s like the first thing that we check and make sure of because owners will tell you whatever you want, whatever they think will sell the place, they’ll tell you.

[00:10:56] Ben Wolff: So you really gotta do your own research. And then it just became, I saw this property in Fredericksburg I really liked, but the guy was asking at the time, like probably. Two times what it was worth. You had it listed for like in the mid sixes and it was probably worth like three 50 at most, maybe four on the super high end.

[00:11:15] Ben Wolff: And then two months later I found a property two parcels down that was basically the same property, but. It was 375 and it had this big kind of ditch through the middle of it, which made it undesirable for a single family home or something like that, but allowed us to build units along the ditch.

[00:11:35] Ben Wolff: And long term, we might actually create like a little stream or something in there, but even as it is now, it’s a cool land feature. So we were able to turn a negative into a positive there. Was it almost like in a floodplain? Oh, there was a considerable amount of it that was in a floodplain as well, and those units were, we planned as treehouse units, so we elevated them.

[00:11:57] Ben Wolff: They were going to be treehouse units anyway, so it really worked. And then the one thing I do want to say, in terms of locking the place down, it’s all about speed when it comes to that, right? I mean, Zillow, realtor, off market, on market, whatever it is, maybe off market you have a little more time. But for something that’s on the market, both my Fredericksburg property, Wim property, I got under contract the day after it hit the market.

[00:12:21] Patrick Donley: So when you get it under contract, are you putting any contingencies on it or are you, I mean, you’ve gotta get some due diligence done. You can’t just go into it. 

[00:12:29] Ben Wolff: Yeah, usually of course, yeah. Usually we’ll get like a a 10 day option period or something like that. With Wimberley, I actually was able to negotiate more.

[00:12:38] Ben Wolff: I mean, I’ll ask for whatever I think I can get right? If I think I can get a month, two months and now I push more, we’re more established. I can say everything we’ve gotten under contract, we’ve closed on that didn’t have like deeded restrictions or something that was unworkable. That helps our case.

[00:12:55] Ben Wolff: So yeah, now I try to get 60, 90, something like that for a due diligence period. But usually you land somewhere in the 30 to 60 range. But my first property, I mean, I think it was 10 days, two weeks, something like that. 

[00:13:06] Patrick Donley: So that first property, I’m fascinated by this. What was the acreage? Did you have a plan drawn out or you’re limited to what the land offers, right?

[00:13:16] Patrick Donley: So it’s not like you can have a plan ready to roll. So talk to us about that. Like how, just how you planned the project. 

[00:13:23] Ben Wolff: We had some idea of unit types. We had that and we actually, we had that dripping Springs property that fell through. Part of that 10 grand was developing a site plan and thinking about unit types and all this kind of stuff, which a lot of that stuff doesn’t transfer, but some of it does, like unit types, for example.

[00:13:39] Ben Wolff: We could think about where they would fit on this new site. And just the process of working with the architect and designer I was working with was a lot quicker and more streamlined. He knew what I liked I knew how he was going to design things in the process, so that went quicker. But yeah, there’s definitely an element of what is the land calling for.

[00:13:57] Ben Wolff: I could definitely speak to that more at Wimberley as well. I mean, Fredericksburg is very much this bespoke. We were trying a whole bunch of different stuff. We didn’t really know what we were doing right, in all honesty. But we wanted to try a bunch of stuff and really blow people away with unique units.

[00:14:14] Ben Wolff: And the different options they had in terms of staying with us tents, tree house container, home dome, and part of it was just seeing what does the best, what’s the easiest to manage, what’s the biggest pain operationally, what’s the most expensive, least expensive? Just thinking about all those things. 

[00:14:34] Patrick Donley: So you had raised money to do all this, right?

[00:14:36] Patrick Donley: You had started a fund at that point, and I just am interested in how you did the capital stack, how you found investors, things like that. Can you go into that? 

[00:14:45] Ben Wolff: Yeah, so it’s a little more complicated than we just raised a fund. So this O Fredericksburg project and the whole landscape hotel glamping resort that I was going to do in the Texas Hill country, I actually just raised initially from friends and family, and then we decided we were going to raise a bigger, more legitimate real estate fund, and later on we actually rolled that project into the fund.

[00:15:05] Ben Wolff: So, and that was great for the fund because we had a project that was like six, eight months down the line. We were only a few months away from completion and cashflow, so it was good for the fund. We were able to give those original investors a stake in the fund and also like some interest, basically like high interest for the time loss from when they put money into when we closed the fund.

[00:15:27] Ben Wolff: So that’s how that piece worked. That was the equity. Then when it comes to the bank and lending, it was I called 20 local banks maybe more and I got 18 noss and one maybe. And one, yes. I mean, that’s just like, it’s just, I really feel like banking you, I had some track record to show for that definitely helped.

[00:15:47] Ben Wolff: Right? I had built up Blink. They loved that cash flow. Blink was a guarantor. So that was big. I mean, I didn’t really have much in the way of assets to speak of, so me being a guarantor didn’t mean that much. My partner John, had a little bit, still not a ton. I think Blink and the cashflow there was probably the, our biggest asset besides for just finding a commercial loan officer that really loved the product, believed in it was like, I want to take my wife here.

[00:16:13] Ben Wolff: I mean that, that’s what it was. Finding an advocate that was willing to go to bat for us and believed in the product at one of these local banks.

[00:16:20] Patrick Donley: So you hadn’t had any development experience at that point. Did you have a model that, like when you approached this commercial loan officer, like this is what we’re modeling it after, this is what we’re going to do, this is our vision.

[00:16:30] Patrick Donley: Because I can imagine it’d be hard to explain to a guy that’s like not done glamping or not done a unique stay. 

[00:16:38] Ben Wolff: We did. We definitely did. We had a nice package, a lot of pretty pictures, renderings we from our suppliers that had these kind of outta the box units, we were able to show those.

[00:16:48] Ben Wolff: And then we were working with this Custom Tree House Builder Artistry. 

[00:16:52] Patrick Donley: I love that name. It’s Artist Tree. Right. 

[00:16:55] Ben Wolff: Yeah, so, and they have this very high-end, beautiful custom tree house micro resort in Spicewood. They’ve actually had them for years now, and we were able to use some of those units as comps and also it lent credibility to us as well.

[00:17:11] Ben Wolff: Like, hey, These, the guys that are designing and building for us have already done this. These are their units they helped put together the package for us designed Monarch from scratch with my collaboration. Monarch was a collaborative effort. Spy Gloss. They already actually had out of the box.

[00:17:26] Ben Wolff: That’s like an artistry unit. 

[00:17:28] Patrick Donley: I. Can I just want to stop you there. Let’s take a step back ’cause I really want to go into Spyglass and Monarch. Those are two really unique properties. I love ’em. I love I 

[00:17:37] Patrick Donley: want to stay in Spy Glass, but talk to us a little bit about Spyglass first. Like, it’s a super unique design.

[00:17:43] Patrick Donley: It’s not just a box on stilts. 

[00:17:46] Ben Wolff: No. So Monarch actually came first and initially artistry. Artistry wasn’t really even offering up Spyglass. This was like an a product that they were going to. Basically to do this rev share deal with developers, and I don’t think that really panned out. And we ended up being the first spyglass and we were searching for another unit at some point along the line.

[00:18:05] Ben Wolff: I can’t remember why but we were searching for another unit and. We all agreed we wanted to do like a higher end, more luxury unit like Monarch, and they were like, Hey, we have Spyglass. I think it would fit really well in this part of the site. You know where it is. And the canopy perched up and focusing into a group of trees.

[00:18:25] Ben Wolff: It just feels super private. And I was like, I mean, it fits, it works. I loved the curved nature. I feel like that’s very unique. I think that’s very attractive. It’s got this kind of minimalistic. Elegance to it, right? It’s like a very elegant shape, especially the interior shot. One thing that I found later with Spyglass, actually differing from Monarch, it’s really photogenic from the interior.

[00:18:49] Ben Wolff: You’re able to get this shot straight through the unit with the hot tub out on the back, and it really just photographs really well from the interior. The exterior is actually more of a challenge with Spyglass and Monarch, the reverse.

[00:19:05] Ben Wolff: Get that straight through shot. The layout’s a little more awkward for that, but the exterior just sings right and sells it. So future sites, we’re actually trying to find a unit that’s got the best of both, but with Monarch, less so is Spyglass because they already had it outta the box. It’s very much a collaborative approach, right?

[00:19:22] Ben Wolff: Like I’ll have an with architects and designers in general artistry before and we worked with this guy, Adam Gates now, and he’s got a team in Barcelona as well. They, I have an idea. They have an idea. We riff on it it, it evolves, right? And we try to create this situation where the best idea wins, right?

[00:19:40] Ben Wolff: It’s this collaborative approach as opposed to like I’m the architect and all this ego wrapped into my design. So I really try to find architects and designers that are interested in collaboration and sort of egoless in the sense of, let’s let the best design win the most attractive, interesting design.

[00:19:59] Patrick Donley: So for our listeners that want to take a look at Spyglass or Monarch, how can they take a look? 

[00:20:04] Ben Wolff: So you can go to our website https://stayonera.com/ and then same spelling, @stayonera our Instagram. So you can check us out on Instagram as well. We’re really, as I’m sure you’ve seen, focusing a lot on our content machine on Instagram.

[00:20:20] Ben Wolff: So originally when opened, I was just listed on Airbnb. That was my bread and butter. That’s what I knew how to do. And we were having amazing results on Airbnb and we actually had our first influencer, found me on Airbnb, found us Stay Onera, and was just incessantly messaging us, right? Like, let me stay, let me do this post.

[00:20:42] Ben Wolff: And I wanted to do direct bookings and set an Instagram up, but it was on the back burner. 

[00:20:47] Patrick Donley: What is the cut that Airbnb takes? 

[00:20:50] Ben Wolff: So they take 3% from the host, but then they’re charging the guests like 12%. So net effective, it’s like 15. So it’s pretty considerable, similar to a lot of the other ones.

[00:20:59] Ben Wolff: VRBO is even a little less, I think all in booking.com is the same or more. So it’s considerable and I just didn’t realize the power and to some extent the ease. Of building this direct booking engine through social, if you have a highly Instagrammable unique products, right? So you need the product that fits the platform in that marketing strategy.

[00:21:21] Ben Wolff: Like if we just had run of the mill town homes or basic apartments, then, I mean, there’s almost nothing you can do, right? You need a unique product that’s going to sell that way. So this influencer kept hitting me up and it was this thing where I was like, yeah, whatever. Yeah, whatever. And I think it made her like, want it more, right?

[00:21:36] Ben Wolff: Like, I want to be the first person to showcase this product, this new project in central Texas that’s super unique. So finally, I said yes, and she was super helpful and super valuable. She didn’t charge me anything ’cause I was not willing to do that at that time. Now I’m open to that and we’ve had her back and are happy to pay her ’cause we know the value that’s generated.

[00:21:55] Ben Wolff: But first time around was not willing to do that. We just did a comp stay, right? She got to stay, she got loads of content. We did a giveaway with her via Instagram and that’s like right when I got the initial Instagram engine going. So got our Instagram page up. I was doing it myself. Didn’t really know what I was doing, was just posting photos that we had and we had good photos.

[00:22:18] Ben Wolff: We’ve since moved to really focusing on video because that’s, that has a way better chance of going viral. But at the time, just posting photos. She did a giveaway. We probably picked up, I don’t know, five to 8,000 followers just from her giveaway. And in that first month we did like 10,000 indirect bookings with one of her posts.

[00:22:40] Ben Wolff: And then the following month we did like, I think it was like 30,000 indirect bookings also largely tied to another post that she did. So I mean, the returns were just unbelievable, right? For giving up one comp night, which. Maybe the expected value on that night is 200 bucks or 250 bucks, some random weeknight in February, right?

[00:23:00] Patrick Donley: So at that point, it sounded like Instagram came first. You’re now on Twitter. That’s where you and I connected. Talk to us a little bit about just your social media strategy. We had mentioned Isaac French and he does a fantastic job in marketing. What’s this place called? Live Oak Lake.

[00:23:14] Patrick Donley: Yeah. So talk to us a little bit more about just your strategy in general in how you’re going about creating the content, creating the videos, creating Instagrammable moments that you can put out there. 

[00:23:26] Ben Wolff: So we tried to outsource this stuff. Okay. We’ve tried a number of agencies both for my Twitter, for LinkedIn, for on’s, Instagram, spirit of Sophia’s Instagram.

[00:23:37] Ben Wolff: And we’ve just found that no one’s going to do it like us, right? I mean, there’s an element of that, which I wish there was an agency that I knew of that we could hire that would take it off our plate, but it has forced us. To build this amazing internal team. So we have producers, editors people that help with storyboarding.

[00:23:55] Ben Wolff: We have, you obviously like copywriters and shooters, right? We have this whole team, some of which contracts, some of which full-time and how we’re able to perform relative to like when I was just goofing around myself. And then even when we had the agency is, it’s remarkable the difference when we really focus on creating this.

[00:24:16] Ben Wolff: Highly engaging, well thought out with strong hooks, right? Videos that have a, have subtlety and nuance to them and really like evoke emotion from our audience and inspire our audience to book. And you’re getting these guests that are inspired so they’re willing to pay more, right? They’re less price sensitive and they’re also we’re cutting out the O T A fees.

[00:24:42] Ben Wolff: There’s no booking platform fees. Say, explain what O T A fees are. Online travel agency, so that’s Airbnb, booking.com, any of these we just call those O T A fees. So what Airbnb’s charging 12% to the guests and 3% to the host. We’re able to capture, let’s say, 80, 90% of that margin. We try to create price parody on our website and Airbnb we’ll shave a percentage or two off on the website, but generally website bookings are getting driven from Instagram and that ironically enough that.

[00:25:13] Ben Wolff: Audience is willing to pay more than Airbnb. Airbnb, a lot of times is price shopping. Some of those guests are aspirational and just want the most unique, exciting stay, but they’re comparing them against a bunch of other stays. Somebody goes to our Instagram page, then goes directly to our website.

[00:25:29] Ben Wolff: They’re only comparing us to us. 

[00:25:32] Patrick Donley: So talk to me about the staff at, on, how are you guys managing all this? You mentioned a little bit about the online media, social media stuff, but talk to us more broadly in, in terms of the staff that you have there. 

[00:25:43] Ben Wolff: Yeah, of course. So we have an onsite manager at On who’s amazing.

[00:25:48] Ben Wolff: He actually he worked at Under Canvas at one point, so he’s got quite a bit of experience in this space. And yeah, he handles any, like on the ground issues that we need. Then I have an offshore team in the Philippines. And I now have a dedicated team just for on, so there’s a, I mean, that’s not true on Spear Sophia and a few of our other, like higher end homes, so more of the sort of higher end product line that we have.

[00:26:12] Ben Wolff: I have a dedicated team of five folks that are really just cream of the crop. In the Philippines? Yeah, in the Philippines. And we have a very robust hiring process to make sure that we’re really getting the cream of the crop and it’s proven out. 

[00:26:25] Patrick Donley: Are you using an agency to find overseas talent or do you, how do you go about doing that?

[00:26:31] Ben Wolff: So, I used to do it all myself through Upwork and then I had my GM and other members of my team recruiting via Upwork as well. Upwork’s gotten very crowded and competitive. It’s harder and harder to attract talent and identify talent at decent rates. So, went on a limb and saw, I think Nick Huber posted about Support Shepherd his company, that helped source folks from over there.

[00:26:54] Ben Wolff: And we ended up working with them. So our last hire we did through Support Shepherd, the other members of the team were all through Upwork or referrals. I’ve had a lot of luck with referrals, so if I find one good person on Upwork, they’ll refer other people that they’ve worked with in other jobs or folks that they know are good.

[00:27:11] Ben Wolff: But yeah, our latest hires from Support Shepherd, and she’s awesome. She’s really great, I will say. So they have a great policy where if you’re not happy with your hire, they’ll go out and find another one. And we had this scenario where this, we have this robust interviewing process, four interviews or something, did a bunch of tests.

[00:27:29] Ben Wolff: And this girl interviewed great and she, we thought she was going to be fantastic. I was super excited about her. And on day one, it was just very clear that she wasn’t a team player. From the manager of that team was like I’m sorry, she’s. She’s not flexible with her schedule. She’s like basically just telling me how it’s going to go.

[00:27:49] Ben Wolff: And I’ve learned over the years hire slow, fire fast. If we made a mistake and she interviewed well and it wasn’t going to work out, just cut her loose right away. So that’s what we did. We told Support Shepherd, they got us another number of candidates and within a month we had a another rockstar who has proven out to be great.

[00:28:07] Patrick Donley: I think Nick is, I think he hired his first three people from Support Shepherd and they were all fantastic. And I’ve got an episode of, with Nick coming out next week actually. So, and he goes into all the different companies he, that he’s up to lately. So he’s got a lot going on. So I wanted to backtrack a little bit and talk about some of your career steps.

[00:28:26] Patrick Donley: You’ve had a really interesting career progression and it seems like you’re not afraid to like make a 90 degree turn, do something completely outside of the box for somebody like that’s early in their career. I just wanted to hear how you go about pursuing a dream or pursuing what maybe could be called a calling.

[00:28:43] Patrick Donley: There’s a lot of people that are probably just stuck in, I think I heard a stat yesterday that 80% of people just don’t like their careers, don’t like their jobs. So can you talk a little bit about how you’ve gone about finding work that’s right for you, pursuing and having the confidence to pursue the things that you’ve done?

[00:29:01] Ben Wolff: Yeah. Happy to. I talk to my wife about this sometimes. It’s like, I think I have this view. I’m willing to take risks clearly. And part of my philosophy is worst case scenario, I’ll go get a job, right? I feel like I’m employable. I’ve been able to get jobs before. And I believe that if I fall flat on my face, I can go get a job, right?

[00:29:22] Ben Wolff: So that, that’s like if my worst case, I think about worst case scenario. And the worst case scenario is not that bad. And realistically what’ll happen is I’ll get a job I’ll do well in it for a few years, and then I’ll get the itch and I’ll try and start something else, right? That’s just part of my makeup, right?

[00:29:35] Ben Wolff: I’m going to be restless if I’m working for somebody else for too long. I think that having that perspective, and look, I’ve gotten my butt handed to me a few times, so I know what that’s like. I’ve, I know what it’s like to fall flat on my face, and I’ve developed a bit of resilience, which I think helps to alleviate some of that fear that might be associated with getting stuck in a job.

[00:29:58] Ben Wolff: And look, when it comes to a calling, if you would’ve asked me that three years ago, I would’ve said, I don’t, I mean, I might not have been honest about it, but I didn’t feel like what I was doing was my calling. I didn’t think Airbnb management and building up this. Lease arbitrage company like it. It wasn’t my calling, but it made good money and I was scaling the operation and it was interesting enough, and I thought that over the course, maybe I would find something that was more of my calling and that ended up happening Right with Onera.

[00:30:26] Ben Wolff: I do certainly believe that unique stays providing a one of a kind experience. I have found something that I truly love and I am so grateful for that because there was a long time I was like, I don’t know if I’m ever going to find that, which I think most people feel right. I definitely was there and I also, there was a lot of time I knew I wanted to be an entrepreneur and start my own thing, but I didn’t think I was creative enough.

[00:30:48] Ben Wolff: Right. This limiting belief. I’m a good executor. I’m really good at having a sense of urgency and pushing things forward and being responsible for a wide set of functions and whatnot, and developing people and all that. But I didn’t think I was creative enough.

[00:31:05] Ben Wolff: But I did think that I could stop talent and I could stop what is interesting and help refine it and make it even better. And that’s what I’ve done with on and future developments, right? I work with creatives, so I have architects and designers and all these folks that I collaborate with.

[00:31:20] Ben Wolff: In order to create these amazing spaces. And then again, it’s about not being afraid to ask a bank for millions of dollars to build tree houses or it’s just, you really have to get past that idea and that really, that fear. 

[00:31:35] Patrick Donley: Did you have any books or podcasts or mentors early on that have influenced you during this course of your entrepreneurial life?

[00:31:44] Ben Wolff: So my dad gave me, and I read super early How to Win Friends and Influence People. I don’t remember like specific chapters or anything like that, but I do remember, and I was like a teenager, I think. I do think it started me on this quest of learning how to work well with others, right? And to persuade people and.

[00:32:03] Ben Wolff: Be likable, I think is important and I think parlayed into charisma and being also being genuine. I think that’s an element, like a genuineness and being able to establish trust is something that is a, it’s a big part of who I am. I’m able to leverage that. I mean, not even consciously, but just subconsciously I’m able to leverage that into building relationships really quickly, getting a bank to trust me that I’m going to build this $5 million micro treehouse resort and it’s going to do super well.

[00:32:36] Ben Wolff: So yeah, I think that book really helped get me on the path. In terms of people, I mean, certainly Jesse, my partner and co-founder now, I mean, I used to work for him, so he got me into the whole Airbnb game. He had an Airbnb short-term rental management company called Sensay back in like, I think they started around maybe 20 12, 20 13, something like that.

[00:32:57] Ben Wolff: And I worked for him in 2014. Helped do some business development, helped to launch a boutique hotel that they had purchased in San Francisco. He saw potential in me early. I mean, I was in my mid twenties, right? He was late thirties, CEO founder of this company. And we always stayed in touch and remained friends and did some trips together and stuff like that.

[00:33:20] Ben Wolff: And I always, first of all, he got me into this Airbnb space in general. And then I think I mentioned he had this compound in Joshua Tree that got my wheels churning around unique stays and glamping and all the rest. It’s funny, you talk to him, he’ll tell you that. Like, I took what he was doing and took it to the nth degree.

[00:33:37] Ben Wolff: Right? He had a converted bus and a garage and all this stuff and then I went and created Monarch, right? It was like 10 steps removed from what he was doing. But then he came to on and saw what I was doing and was just like, Man, your biggest mistake was you didn’t do more, right? You didn’t build more, I think, joking, right?

[00:33:53] Ben Wolff: I mean I was limited from a resource standpoint, but yeah. And then, I mean, he’s the best that I know and the best that a lot of really credible folks in our space know for revenue management, pricing optimization. He’s a math and expected value whizz, and I knew how much value that was going to bring to our business.

[00:34:12] Ben Wolff: So I paid a lot. Equity in salary to, to get him on board. And he’s one of the best I know at getting up to speed on something really quickly. So going zero to 85, 90 and then becoming the best at something. He’s really good and process oriented when it comes to that.

[00:34:30] Ben Wolff: And he’s actually the one driving and sort of leading a lot of the engine of our social team right now. And I know he’s already gone from our best performing video reel without collaborators was. Probably like 10,000 views or something. And now we have multiple videos with two, 250,000 views and we’ve only been doing it for a couple months.

[00:34:50] Ben Wolff: So he’s just if I can let him go off and figure stuff out and I handle everything else, and help build the team and lead the vision, have this big vision that we’re driving towards and allow him to innovate. It’s a really good balanced setup we have. 

[00:35:09] Patrick Donley: I wanted to hear what part of all this you enjoy the most, like the visioning strategy part of it, the architectural part of creating the actual properties themselves, managing the staff, building the company.

[00:35:21] Patrick Donley: What part of it are you enjoying the most? 

[00:35:25] Ben Wolff: So there is something about development that’s really special to me. Seeing a piece of raw dirt land and being able to envision what that can become. Then turning it into that thing is very exciting to me and empowering and it’s just super cool and the various stages along the way, right?

[00:35:44] Ben Wolff: So like finding that perfect piece of land that I go and I’m like, this is it. I’ve seen 20 other places I’m depressed that I’m not going to find the one and that I find the one right. And I just know. That’s super exciting. And then the initial concepting, right? Like walking the site with architects and designers and figuring out what we’re going to do.

[00:36:05] Ben Wolff: Letting the land speak to us a little bit, like what makes sense where, and then iterating on the concepts. So then it’s like concept deck. Oh wow, this is the site plan. These are the kind of units that we’re actually going to do that are going to blow people away. And then it’s the like clearing, okay, this is where the units are going to go.

[00:36:21] Ben Wolff: This was just like a forest. Now I can start to see where they’re going to go. Then it’s ground up the utilities and infrastructure isn’t all that exciting to me. Right. But once we’re ground up and can actually see the unit where it’s going and then the finished products, I mean it’s there’s not much like it.

[00:36:38] Ben Wolff: And then so the stuff on development side, on the other side of things, I mean, look, I love building the organization that we have and really trying to only attract top tier talent because one thing that I’ve found is that, The best way to piss off an A player is surround him with C players, right? So really trying to make sure we only have a players around us, which is really hard.

[00:36:59] Ben Wolff: It’s super easy to get discouraged and be like, I’m just, I’m not going to find the right person. Let’s just fill the gap with whoever we need to. And it’s just, you’re doing yourself and your team a disservice. So trying to craft the organization our mission values and really development of people internally, that’s exciting to me too.

[00:37:19] Patrick Donley: You’ve got a project underway now. Can you talk about that? I think it’s 28 units. It’s a mix. I wanted to hear more about your next project that you guys are up to. 

[00:37:29] Ben Wolff: I can, yeah. And this was really the property I was talking about when I said this is it. When I saw the land, I mean, oh, near Fredericksburg.

[00:37:36] Ben Wolff: I loved, it’s half a mile from Main Street. It’s in this little forest that looks off the bean path. It’s on a on a creek that’s really beautiful and nice and serene. But the Wimberley property is, Breathtaking. I mean, it’s pushed on top of a hill, couple miles from Wimberley Square, which is a really cool vibey, hippy dippy, nature focused town in central Texas.

[00:38:00] Ben Wolff: Really cool views. They have a lot of water features like Blue Hole Jacob’s. Well, there’s a number of these kind of water feature natural water feature attractions, and Cypress Creek runs through the main town of Wimberley. So you have all these restaurants and stuff. Cypress trees that are massive and hundreds of years old.

[00:38:18] Ben Wolff: It’s super cool and not something you would think would be in Texas, but it is and it’s super cool. So found this piece of land that just has these views that go on for, I mean I have to find out the exact number ’cause I just throw stuff out there, but it’s gotta be a hundred miles, right? It’s it, they go on for a long time and there’s a lot of topography change.

[00:38:37] Ben Wolff: So it just creates a lot of drama with the view as well. And they’re west facing. So you got these like incredible sunsets on top of it. So I mean, I saw this land. I was actually with my wife who was pregnant and my mother-in-law. Like I said, I got under contract the next day, got close with the owners, found out they were selling this five acre parcel up top and they owned 14 acres down below and found out they were like interested in maybe selling that and figured out a way to.

[00:39:06] Ben Wolff: Pull that away as well and get a better price per acre actually on the whole thing by buying the whole kit and caboodle and doing a much bigger project than I thought I was going to do. I thought we were going to do 10 units on the, on that little five acre parcel. And turns out we’re doing 28 units on a 20 acre parcel within Event Barn and this beautiful Infinity Edge pool and all facing these killer views and the five acre sort of top parcel with some of the best views.

[00:39:34] Ben Wolff: We’re doing very similar units to spyglass. They’re a little bigger decks on the end, but still hot tip on the end, that kind of tubular shape and kind of poking out from the side of the hill with all these trees interspersed. So it’s a really good unit for the land there because there’s not a ton of land.

[00:39:51] Ben Wolff: So we needed narrow units and we also need had to figure out how to create privacy with those kind of narrow shooted units. So the spyglass or similar unit made a lot of sense. Then down below we have a new unit type that we’re calling the greenhouse, which is similar to walnut, if you’ve seen that on the ERO site.

[00:40:09] Ben Wolff: It’s similar to a container home, but it’s not a container home, a box, and it’s just has these floor to ceiling, massive windows in the front, tons of glass facing this amazing view generous deck out that window and sliding doors with a hot tub all facing this view. And then there’s a vegetated rooftop deck.

[00:40:28] Ben Wolff: On the top of the unit, so it blends into the hillside, is the goal, right? We’re going to have this natural kind of prairie grass and various native Texas grasses that are going to grow on the roof, 

[00:40:39] Patrick Donley: I think. Who’s the Treehouse guy? Pete, do you know the Treehouse master? Do you know that show? 

[00:40:44] Ben Wolff: I do know the show.

[00:40:46] Ben Wolff: I don’t know the guy’s name. 

[00:40:48] Patrick Donley: I’m blanking on his name, but he had a project, a tree house that he did with a live living roof that looked pretty fun to do with the watering system up there and everything. 

[00:40:56] Ben Wolff: So, We’re going to, so water is a big issue in central Texas, so we’re really trying to be very conscious, doing native as much as possible and trying to minimize the irrigation requirements that we’re going to need.

[00:41:08] Patrick Donley: Is artistry involved in this one? 

[00:41:11] Ben Wolff: They are involved in this one. They helped a lot of the concepting and initial, and we have some other local architects they’re really more so in California these days, so we’re working with some more local architects on. Stage that we’re at now, which is really like construction administration and more of the brass tacks of getting the thing built.

[00:41:28] Ben Wolff: And it’s cool. I mean, we’re foundations are poured, we’re getting framed up. I mean, you can see what this thing’s going to be. 

[00:41:36] Patrick Donley: Are you posting this stuff on Twitter? 

[00:41:39] Ben Wolff: Not yet, but we will be posting it on Twitter. I actually have our new lead producer who’s also a videographer, is coming to Central Text next week, and we’re going to do a few hours out there and we’re to shoot .

[00:41:54] Patrick Donley: Absolutely. I mean, I think there’s so many people on real estate Twitter that would be fascinated by this and love to follow the progress. I had Antonio Botero on Erra. She’s out in Park City, Utah. I don’t know if you follow her on Twitter, she’s great, but she’s building her dream house out in Park City and just documenting the whole thing on Twitter and it’s just fun to follow her, like the stages of it.

[00:42:14] Patrick Donley: And I think something similar with this in Wimberly would be awesome too. 

[00:42:20] Ben Wolff: Totally agree. I mean we’ve been talking about it and it’s just a matter of like getting out there, shooting and putting it out. 

[00:42:26] Patrick Donley: So talk to me a little bit more. You’ve also got a place in Palm Springs called the Spirit of Sophia.

[00:42:32] Patrick Donley: Talk to us about that project, what that was like to do. 

[00:42:36] Ben Wolff: Sure. So Spirit of Sophia is another asset in the real estate fund that I raised with John and the whole idea around Spirit Sophia. Is boutique hotel renovation. So we bought an existing boutique hotel that was vanilla, right?

[00:42:53] Ben Wolff: I mean, it was everything was white. It was Spanish revival, Mediterranean style. It had pretty good bones, but there wasn’t a whole lot of pizazz. And we basically just tried to go as vibey, Instagramable and fun as we possibly could with that property. And I will say too, I mean, I hired a great designer who actually works on our social team now as well, and Jesse was living out in Southern California, so he’s, he was helping a lot with that project.

[00:43:21] Ben Wolff: As well. And thankfully on, I mean I was involved in every little step along the way. Thankfully with fear to Sophia, I was able to have my team really bring that to life and just be a checkpoint along the way, which was really awesome. Thinking about how we scale this, like how we do more of these projects and really churn them out.

[00:43:41] Ben Wolff: So yeah, the idea with spirit of Sophia was how do we bring it to life? And also it’s a 23 bedroom, but there’s two sides. So there’s an 11 bedroom side and a 12 bedroom side, so you can rent it as like a big group. And then we also thought we could rent individual rooms as well. Came to find out that renting to the big groups was the more profitable and higher margin and less operational headache than doing 11 individual check-ins and checkouts.

[00:44:08] Ben Wolff: Different guests. So we leaned into that and we really targeted the amenity stack around that, like right. We turned the lobby into more of a dining room kitchen. We turned what was the spa into like a three bedroom villa with a living room. We created these beautiful outdoor dining spaces and this big green turf area, which is super Instagramable with like this cozy nook with a bunch of mirrors in the back.

[00:44:34] Ben Wolff: Just tried to make it as attractive from a design standpoint and really like fun and vibey as we could. We call it the Palm Springest experience in all of Palm Springs, right? And that’s like our running joke, right? We just tried to lean into the rainbows and the the turf and the twinkle lights and all this kind of stuff.

[00:44:54] Ben Wolff: And it has this beautiful backdrop of the mountains. So you get these amazing photos, but you’re right in the heart of Palm Springs, which is part of the beauty of Palm Springs, right? It’s that. You have this beautiful mid-century architecture. You have these amazing mountains behind you, and you also have these like cool hip shops and restaurants and all these fun things to do, right?

[00:45:12] Ben Wolff: Downtown and golf courses all around. 

[00:45:14] Patrick Donley: And golf courses, right? Yes. So like an average day, is you’re most of your focus on Wimberly right now, or are you thinking bigger picture? Like what’s the next project? Where are we headed with this? Talk to us just about an average day for you. 

[00:45:28] Ben Wolff: Yeah, so I’m definitely managing a lot of things, but I have really good people around me.

[00:45:33] Ben Wolff: I feel as well supported as I ever have in my career, and some of that comes down to I’m not willing to skimm. On the people that I hire, I will pay more for better people. My GC today, I know he’s a little more expensive. I mean he’s more expensive than the first GC that I hired, but the first GC that I hired came in 50% over budget.

[00:45:54] Ben Wolff: And I know my guy now is going to gimme a number that he’s going to hit or come under. And I trust him to the nth degree. We have a weekly meeting out there. He brings stuff to me that he needs to, but I don’t have to micromanage him at all. Right. I know he’s going to figure it out. So as much as I can trying to put people like that around me my partner, Jesse, that I mentioned, like he’s sort of leading and helping build this social machine and checking in with me along the way.

[00:46:18] Ben Wolff: I mean, right now we’re building this new department, so we’re talking. More than usual hour and a half a day. A lot in a lot of cases. Trying to figure out the best path forward and how we’re going to roll this out. But, sorry, when we’re not building up a new department, we may only talk 20, 30 minutes a day.

[00:46:36] Patrick Donley: That new department is social media related. 

[00:46:39] Ben Wolff: Exactly. Yeah. Social media, so content creation, working with influencers and collaborators, so continuing to build that network and recruit them and manage them and all that. And then just the social media management, right? Posting and captions and community engagement, all that kind of stuff.

[00:46:55] Ben Wolff: So yeah we’re doing that for ourselves, honing it for ourselves. We do have third party clients already, and we are. At the stage where we can really bring on additional third party clients and we think blow it outta the water for them really perform. And that kind of gets into this full service revenue management approach that we’re taking.

[00:47:14] Ben Wolff: So it’s this like holistic revenue management approach and revenue growth approach. So it’s pricing optimization, guest experience, and customer service. And then you layer social on top of that. The content creation engaging videos that have the chance to go viral, and then social media influencers to help grow the audience.

[00:47:36] Ben Wolff: It’s this like perfect storm of, I mean, we can bump you from where you’re at, 10, 15, 20, 20 5%, sometimes more. And we only, we try to only work with third party clients. That are willing to invest in their products, right? Like they want to be one of one in their market. They’re willing to invest in that.

[00:47:53] Ben Wolff: We don’t want to work with clients that are like skimping and trying to cut corners and offer like a value product because it doesn’t serve us, it doesn’t serve them. It’s not best suited for social and it’s not best suited for our model. 

[00:48:06] Patrick Donley: So are you doing active outreach then for these third party people or are they approaching you?

[00:48:11] Ben Wolff: Right now they’re approaching us. It’s all inbound and we sort of talks about, I have my hands full with ero, Wimberley, ero, Fredericksburg, continuing to build out this team work with my various departments and make sure the machine is sort of running the way it should be, building out systems and processes so we can scale.

[00:48:28] Ben Wolff: We’ve done a lot of that. So we’re definitely able to bring on a number of quality targeted clients, but we’re not quite at the point of like, I want to do a bunch of outbound and I just believe in this strategy of pull a little more than push, right? If I can, if what I say resonates with people and the type of products we have resonates with people, I’m hoping that will attract.

[00:48:50] Ben Wolff: And so far it has attract like-minded folks that, that want to deliver a higher end, unique one-on-one experience. Like I’m not getting a lot of people that are like, oh, I’m throwing up tents in the backyard. Will you help me price them? It’s not really the audience. I mean, I talk a lot about spend more to make more, right?

[00:49:05] Ben Wolff: Not had a cost cut. 

[00:49:07] Patrick Donley: So where do you see the unique stays market going in the next three to five, 

[00:49:11] Ben Wolff: 10 years? So I definitely believe that there’s still room in this kind of higher end piece of the market. I think there’s some more inventory coming out there, but the space is glutted with this mid-tier products, right?

[00:49:27] Ben Wolff: Most of the big brands are, in my opinion, mid-tier auto camp under canvas getaways, even like more of a value product. I still think there’s a lot of room on that top tier, and I think people are willing to pay. I mean, we’ve seen that, right? Like our top performing units cost us more, but I mean, it’s paying for itself in less than a year, right?

[00:49:46] Ben Wolff: The additional cost. So it just makes sense to spend more and do it higher end and better. I also think that, as I said earlier, if you’re a traveler and you have the option to stay at a four star, maybe even a five star chain hotel or stay at. This one of a kind tree house at ona. Yeah. You have to go off property to, to eat dinner, but maybe you like that anyway.

[00:50:12] Ben Wolff: I just think that people are going to choose that option that’s more experiential. You feel like you’re getting so much more for your money in a different way than a traditional hotel. 

[00:50:21] Patrick Donley: I love hearing about these stories. This is really great stuff that you’re up to and I really admire all that that you’ve created so far and looking forward to seeing what’s on your future horizon.

[00:50:31] Ben Wolff: Thank you, Patrick. Appreciate it. Loved chopping it up. Hopefully you got some good stuff. 

[00:50:35] Patrick Donley: Yeah, this is great Ben. So for our listeners that just wanted to learn more about you, learn more about on, get in contact with you, what’s the best way for them to do that? 

[00:50:44] Ben Wolff: Yeah, so you follow me on Twitter @uniquestaysguy .

[00:50:45] Ben Wolff: Feel free to, to follow me. You’ll hear me talk on about a lot of the stuff that, that we started to touch on in this podcast. Welcome to dmm me as well. You can find me on LinkedIn. Just search Ben Wolff on. I should pop right up. And you can reach out to me that way as well. And certainly follow us at Stay Onera, at Spirit of Sophia, on Instagram.

[00:51:04] Ben Wolff: We’re, I think we’re pumping out some really cool stuff. And if you want to come stay with us, you’re in the area. I think we, we offer a pretty one of a kind experience. 

[00:51:12] Patrick Donley: Absolutely. I’ll put show notes to all the websites and everything so people can find that easily. Ben, thanks a lot for your time.

[00:51:18] Patrick Donley: I really appreciate it. 

[00:51:19] Ben Wolff: Thank you. Appreciate it. 

[00:51:21] Patrick Donley: Okay folks, that’s all I had for today’s episode. I hope you enjoyed the show and I’ll see you back here real soon.

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