March 15, 2023

Increasing Last Minute Bookings through Flexible Availability, with Whimstay CEO David Weiss

In today’s episode, Alex and Annie chat with David Weiss, the CEO of Whimstay. He shares his background in vacation rentals and the global payments space and his journey to becoming Whimstay's CEO.

David discusses how last-minute bookings are their niche and that their goal is to increase incremental bookings while offering the best deals to travelers. He talks about the initiatives they have for this year like partnering with a technology company, intelligent pricing, and expanding into Europe.

Whimstay believes in flexibility and offers broad payment options, including their patented Split Pay option, to create superior experiences. Find out more about how David and Whimstay serve the needs of property owners and travelers in this episode of Alex & Annie: The Real Women of Vacation Rentals.


David: Superior experiences for both property owners and travelers
"Our mission really is to offer exclusive and unique discounts to travelers with a superior experience, but really just the property owners and managers attract incremental guests and generate incremental bookings. The core of that mission is the last-minute window."

In today’s episode, Alex and Annie chat with David Weiss, the CEO of Whimstay. He shares his background in vacation rentals and the global payments space and his journey to becoming Whimstay's CEO.

David discusses how last-minute bookings are their niche and that their goal is to increase incremental bookings while offering the best deals to travelers. He talks about the initiatives they have for this year like partnering with a technology company, intelligent pricing, and expanding into Europe.

Whimstay believes in flexibility and offers broad payment options, including their patented Split Pay option, to create superior experiences. Find out more about how David and Whimstay serve the needs of property owners and travelers in this episode of Alex & Annie: The Real Women of Vacation Rentals.


David: Superior experiences for both property owners and travelers

"Our mission really is to offer exclusive and unique discounts to travelers with a superior experience, but really just the property owners and managers attract incremental guests and generate incremental bookings. The core of that mission is the last-minute window."

David: Offer travelers the flexibility to pay how they want

"The aspect of flexibility, which for us which would also be inclusive of making it easier to cancel and book and change and extend even with the type of value proposition that we have, in addition to saying let's give the traveler however they want to pay for their vacation. Let's give them the flexibility to pay how they want."

Connect with David:

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[00:00:00] Welcome to Alex and Annie, the Real women of vacation rentals. With more than 35 years combined industry experience, Alex Hener and Annie Holcomb have teamed up to connect the dots between inspiration and opportunity. Seeking to find the ones. Story, idea, strategy, or decision that led to their guest big aha moment.

[00:00:22] Join them as they highlight the real stories behind the people and brands that have built vacation rentals into the $100 billion industry it is today. And now it's time to get real and have some fun with your hosts. Alex and Annie, welcome to Alex and Annie, the Real Women of Vacation Rentals. I'm Alex, and I'm a.

[00:00:44] And we for join today with David Weiss, who is the new c e o and on the board of directors for Wims Day. David, welcome to the show. I couldn't imagine literally kicking off my ear in a better way than, uh, than being on your show. So thanks for having me. Very excited to have you here and hear more about what's going on at Wims Day and just about your past and how you've gotten to, to where you are.

[00:01:07] But I guess that's probably a good place to begin. Um, can you tell us just a little bit of history before we start diving? Sure. Well, I spent 20 years in investment banking, uh, before I decided to get my first real job, uh, which was, uh, in the vacation rail space, which I'll talk about. But back to the banking, uh, experience, um, beyond capital raising and advising companies on buying and selling assets.

[00:01:33] I'd say the most relevant part of that journey that I've applied the last, uh, few years is I got a front row. And was an active participant. Um, and in many cases became, for lack of a better term, a trusted advisor to literally hundreds of CEOs and COOs and CFOs and boards of directors, and observed and learned along the way how they operated and scaled their businesses, how they acquired customers, how they marketed their products, how they entered into partner.

[00:02:02] How they expanded internationally. Um, all of this mistakes that they made along the way. Uh, many of the mistakes that they avoided, how they managed, um, every form of crisis from market crashes to nine 11 to a whole myriad of other, other things. Importantly how they, uh, let's say mentored and guided and motivated and incentivized and treated their people, their employees, and, um, set examples, uh, for them, good and bad examples.

[00:02:30] Uh, by the way, lots of good and lots of bad , uh, you know, over the years. And when I realized over that it, you know, I'm a little slow to come up the curve sometime, but after 20 years, I realized that I was, I was more like and more closely associated with this, with this set of this group of people. Group of operators at lots of different companies, at lots of different stages versus this other group of people and that I had thought to myself, I'd really like to try to do something like this and move into an operating role of some kind.

[00:02:57] And so I started taking calls and putting energy and vibe out there in the atmosphere and sort of a magical confluence of events led me tostone back in 2013. Which is a payment, uh, FinTech payments company, which at the time was focused on the vacation rental vertical, uh, and real estate vertical. Um, I ended up being president of the company.

[00:03:20] We tripled the size of the company. We doubled the size of the team. While I was there, we expanded into Europe. But for the purposes of this conversation, my experience there really couldn't have prepared me more for what I'm about to do and have been doing at Wims Day, which is to say the two.

[00:03:38] Experiences that I was responsible for there is, um, I worked with, uh, and led teams that built the end-to-end payments experience at vrbo, uh, which we grew to ultimately seven or 8 billion of processing volume. And what that meant was we onboarded ourselves close to a million property owners in North America and.

[00:03:59] Uh, we, uh, uh, we offered a broad range of payment methods to travelers globally and ancillary services. We launched fraud prevention and chargeback protection. Mm-hmm. , um, uh, compliance services and licensing. We got licensed ourselves and I served on the board, so of our two regulated entities and at the same time in building that helping build that marketplace experience.

[00:04:21] I was working with and leading another set of teams who were already integrated into and, uh, integrated and were on the path to integrate into more vacation rental property management software companies. And through that channel, we onboarded four or 5,000 over the years, property manage, vacation rental, property management companies, uh, uh, and processed at the peak, you know, close to 5 billion in, in processing, you know, volume there.

[00:04:45] So amazing experience. Lot, lots to talk. Um, fast forwarding, you know, we, the company ran into a few different buzz saws all around the same time. Uh, which is we had the complete brilliant foresight, uh, in 2019 to sell our real estate business and double down on traveling. We literally closed at the end of 2019, heading into Oh my 2020.

[00:05:09] 20. Yeah. Great timing, . Yeah. Good timing. Good call. Dave. Um, uh, and, uh, Expedia was in the process of bringing payments in house. Uh, I was gonna change the economics of our business entirely in a material way, and then covid. and so, which was obviously difficult and crazy for everybody. We had somewhat of a triple whammy all happening at the same time.

[00:05:31] Um, and so a lot of learnings through that process. Um, I ended up spending a few years at two private equity companies focused on the travel tech space and the PropTech space. Half my time on investments in acquisitions in those areas, and half my time leading several operating initiative. At certain of those firms, um, certain of those firms, uh, portfolio companies, then a different set of magical events happened to sort of bring me to Wems Day.

[00:05:59] Um, and I won't go into all the details other than to say I was getting to know a person on a project completely having nothing to do with the company, uh, who happened to be a board member and an investor and advisor, and a close friend of Bens, uh, Ben Gem Shahi, the founder and c e o or c e o of until a couple days ago, um, of the com's.

[00:06:20] So weird to say. couple days. , the thought was that he was gonna intro, introduce the two of us together, and he just thought I could just help in some way, right? Where they were going and hiring people and professionalizing the operation and all those types of things. Um, and as we were joking before, we're, uh, we're somewhat opposites, but we just, in terms of lots of, well, lots of ways in which were opposite, but we just immediately hit it off in a very short amount of time.

[00:06:49] And we just began talking about the team and the people and the degree of difficulty and how are we gonna do this and how are we gonna grow it? And they had, he had a, he had a great. Idea. He has a really, really great, he had a really great group of people. He had built a strong product. The product market fit in terms of what Limay is doing is sort of undeniable.

[00:07:08] So that wasn't a really big hurdle in the, in the beginning. And one thing led to another and he offered me the chief operating officer role, which I started back in August, you know, September of, of last year. And the idea at the time was, You know, in the first, in the, in the next 18 to 24 months, and maybe it takes a little longer and maybe it's, uh, you know, a tad bit shorter, but you know, as long as you don't like completely mess the thing up, then there might be an opportunity to, to transition into the ceo, uh, C e O role.

[00:07:36] And it just, it all fast forwarded and. , you know, getting turned around in that wave, it just happened sooner than probably either one of us expected. And so I assume that role January 1st, and I just, I'm, I can't possibly overstate how excited I am for the team and what we're doing and what we're building, you know, heading into 2023.

[00:07:55] That's so amazing. And, and I, um, had, it's interesting you talk about Ben, one of the things that I learned about him and getting to know him is that he has. A very innate gift in finding people that are complimentary, but he just identifies something about an individual that he. Like, I guess nurture. He did that for me when he reached out to me and asked me to kind of be an advisor with ste.

[00:08:20] And it was interesting because when he had the advisory group together, like some of the people that he had on it, I looked at like, these are people I would never be in the same room with. I mean, their disciplines were different, but they were at a whole different level. But I think that Ben found something in me that he thought that he could pull out and, and help me, um, just.

[00:08:38] I guess help bring it out of me and like, and, and, and hone that skill a little more than, than I realized. And, and one, Ben is an amazing human being. Um, he is completely different than anybody that I've ever met because he is just very spiritual in a, in a very, um, Not normal sense of the word, um, but it, but a great way.

[00:08:58] And I think that he saw something in you that he knew was gonna be great to take the company to the next level. So I have no doubt that this, this transition for you is gonna be a great step for the entire group. I appreciate it was an instant connection for me. And I, you know, and he did a lot of that for me.

[00:09:14] I never thought, um, I, I had a pretty good idea I was gonna move into another operating role, but I never thought I was gonna do something this early stage. Yeah. And it just, like I said, we just developed a trust between the two of us, and he did see something in me in that regard. Um, and so it, it happened for me in a similar way, and I'm, I'm really grateful for it.

[00:09:32] And it happened a lot faster than you thought, too, you know? Sorry, my friends like, didn't you just like, But yeah, I mean, it all works out. And look, we're we, we got, we need to get a lot accomplished in a very short period of time. Yeah. And, and then again, he, he's just, he's Ben's unique in a lot of ways, and I think he recognized that we're, we're off to the same thing.

[00:09:52] We want the company to be successful. We wanna grow it. We wanna hire the right people and do the right things. And I think, you know, fortunately for, for me, but I think all of the shareholders of Wednesday, you recognize that this might be the, the, the best and fastest way, uh, forward to get to the objective that we're all trying to get.

[00:10:08] Yeah. What wish is what? , let's, let's dive into what that, what that objective is and, and what is the goal at this point. I know we had been on the show back, I think probably in February of 2021. And, you know, learned about his vision for it. And I think, like you said, there's definitely a good product fit in the market for the value of what Web State provides as an OTA that is different than a lot of them.

[00:10:31] But where do you, where what's gone on in the company and, and where do you see it going now forward? We'll start the show in just a minute, but first a word from our premier brand sponsor, Casa Go and co-sponsors Guest ranger and good neighbor tech. CASA's founder Steve Schwab has been quoted as saying you can only be a local in one place.

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[00:11:37] Good neighbor tech allows you to manage your properties remotely and intelligently, protecting your owners and your guests. Their smart wifi locks allow you to provide temporary access to home and garage from anywhere, and keep track of when guests and service providers are in the property. Good Neighbor Tech provides the ability for you to collect email addresses from all guests staying in a property, not just the one who booked the reservation.

[00:11:59] Every guest who connects to the internet will see your branded welcome page and be prompted to provide their email address in order to connect to the wifi. Visit casa Guest and good neighbor for more information. Well, there's a couple things. You know, I was really excited in, in, in the beginning with, uh, you know, as I said, you know, Ben, the team, the product, and identifying this place in the market, last minute bookings and serving in need that was clearly, um, something that property managers and property owners wanted, and at the same time, offering a really cool value proposition and experience for travelers.

[00:12:36] And as I got into it more deeply over the last couple months, you know, I would say, you know, our mission really is to offer exclusive and unique discounts to travelers with his superior experience, but really just for property owners and managers, attract incremental guests and generate incremental bookings.

[00:12:57] The core of that mission is the last minute window. But one of the things I, I came to a view relatively early on and, and lots going on, on traveler experience and property owner experience and conversion and everything. But what I came to the view of is that our value proposition and what we're building and our capabilities and new people coming in and new technologies and new efforts is our valuation.

[00:13:20] Our, our proposition applies to lots of different points in the booking cycle during the year, uh, which is to say, on the outside before the WIM State piece. I do believe, I also believe in the notion of an alternative channel to the larger sites that was more user friendly, that was less expensive, uh, and served a very specific purpose, specifically around occupancy rate and RevPAR.

[00:13:44] And if you think about what we do in our value proposition, which has been to date, filling nights in the last minute booking window, that might have gone unbook. This applies to me in shoulder seasons, in off seasons, in pre and post holiday periods in weekdays, leading into weekend get getaway destinations, um, and lots of other ways.

[00:14:06] And so we haven't really been public about sort of expanding the market opportunity and the mission and go to market strategy, but you'll hear more from us. , uh, uh, over the next, um, you know, over the next few months about that. Um, that takes really great people. We have folks in the building now. I'm really excited to say that between, as of yesterday, through the end of January, uh, we're gonna have six key new hires join the team.

[00:14:31] Um, uh, chief financial Officer, head of business development, chief customer Officer, um, uh, data science, uh, lead, uh, account manager. And so, More people. These are all people by the way I worked with in the past or never had one or two degrees of, of separation. There's some really interesting partnerships that are going to advance us towards those objectives of building.

[00:14:57] When I say like, we'll build, we're, we're in the process of building a real niche within a massive, massive vertical, and it's a really large niche of what it. But some of this stuff we won't be able to do on our own. So we entered into a partnership. Uh, a part of the thing, one of the things I was working on with Ben is a, with a really large technology company that just doing a number of different things, but just launched in December.

[00:15:18] It's a technology company that through what it is that we're doing together, We're gonna be able to attract an order of magnitude more traveler fingers to push booking buttons onto their platform than we ever would've been able to do on our own. So we have our own s e o and marketing paid efforts, and now we're working with the partner to raise the profile of Wims Day, attract more travelers to our platform and our properties, which might say our properties, our property management customers, properties.

[00:15:49] That's, you know, super. We're ha we're engaged and on the path or some developments around pricing and intelligent pricing and, and uh, uh, and search experience. And so the combination of those things, uh, are, we're just, you know, people say this, and it's kind of a vague term, but we're in the process of taking the company to the next level.

[00:16:09] That involves great people, great product, great go to market strategy, uh, and execution, maybe above all anything else. And, and that's what we'll be focused on at 2023. It's interesting. A lot of the, a lot of organizations that have started, especially after covid, I think, you know, that was a pivotal moment for the technology within, within our space.

[00:16:28] Um, but a lot of the companies that started it, it, it, um, The founders are still maybe in the driver's seat. And I think it's really telling for, Ben had a vision, but he knows in order to take it to the next level, he needed to bring somebody in with your experience and again, your skillset. And, um, I, I'm really curious because you've been kind of around the periphery of the, you know, travel for, for quite some time and specifically vacation rentals and then dealing with an m and a.

[00:16:55] What do you think, um, you know, 18, 24 months from now. What do you think the landscape looks like from, uh, niche travel, from vacation rentals and like the blurred lines between hotels and vacation rentals and then the technology overall? Do you think there's gonna continue to be some consolidation in that, you know, perhaps whims say, becomes part of something else, or, or you buy some technology or you buy some organizations.

[00:17:19] What do you think that might look? Well, at a high level, um, in looking out over, you know, that next couple years, um, there's certainly gonna be continued consolidation in the sector. Um, consolidation when it happens in really strong market environments is, is a slightly different flavor than consolidation that happens in.

[00:17:39] um, uh, economic environments that aren't as robust. One of the things I'm just excited about for, for wi during this period is that, you know, we operate, I mean, it was our first 2021 was really our first real, uh, year of operation, and we performed really well, and that was a period of people were renting nights that they weren't typically renting nights at, and ADRs were high and all this stuff, but we're going into a period now of any you, you know, depending upon your own crystal ball.

[00:18:06] Economic insecurity and recession or worse, and businesses like ours tend to outperform in those environments. Yes. And that is to say, um, uh, as long as you've got the right product and, and the right product, market fit and strategy, very specifically, companies who are offering value proposition inclusive of special deals in some way with a special experience tend to outperform because our, I was joking about this to myself the other day.

[00:18:33] Our, uh, Tata, our. Tangible addressable traveler audience is just bigger now. . Um, and so folks who might have taken the $500 vacation last year, uh, or whatever, a thousand dollars vacation, still want a nice place, but are gonna be more inclined to look at something like our type of service, which is the deal, and investigating more options about how to get the right place.

[00:18:56] Even. They took two vacations last year, but now they're gonna take one vacation this year and they want a great experience and they, they're, they're gonna want and or need a, a, a deal to kind of make that happen. I like the overall. I'm actually, when I'm asked about that piece of it, which wasn't your direct question, I'm excited about what we can do in this market opportunity that we're heading into now, given just the value proposition in what we're building, but it's really incumbent on, on getting this, uh, on getting this right and the execution part.

[00:19:27] We intend to build a business where we're going to, uh, get this point, uh, create a, a, a. I say a niche again, but a place in the overall market that other larger comp companies are gonna find Really interesting because one of the differentiators for us is we're just completely focused on vacational rentals and this, and this objective of just attracting incremental guests and incremental, uh, generating incremental bookings.

[00:19:57] And so, um, larger companies and private equity companies are gonna be looking to. Different types of businesses and different types of mm-hmm. different parts of the value chain to, because the economies of scales are lo, are, are, are really important in our business. And the capital intent city is quite large and.

[00:20:16] Apparently there's these vicious rumors out there that, you know, some of those larger sites have larger resources than we do and make more people than we do. . Some are even bold and brash to say they have more, you know, more recognized brand names than we do. But, uh, it's gonna take hardships more, you know, there's, we're gonna be more consolidation and we're probably in the end, maybe not in the period that you talked about, Annie.

[00:20:40] We're probably gonna be a part of that equation in some. Yeah. So that kind of leads to what my question, uh, all along has been. What, what is that pathway though? I mean, do you see yourselves also trying to become the brand that people, individual consumers know of, and when they, they're going on a last minute trip, they immediately think to go to Wednesday?

[00:21:01] Or is that kind of a lower priority to finding these different partnerships like you're alluding to and different ways to collaborate with other entities? To get the business and to get the bookings. I guess I, I guess the best way to answer that, um, Alex, from my standpoint is both are part of the plan.

[00:21:19] In the beginning. It's really important from my standpoint to focus on, uh, the partnerships, what we can do. We only have limited resources. Uh, it takes a lot of capital resources to build that, that brand. There's lots of other ways to do it. , we're gonna be, we're gonna be really effective given the size of our company on building that brand in a t in, in a, in, in a, in a way that is capital efficient, but we're also gonna leverage working with others to get us to a place faster than we might have otherwise.

[00:21:48] Mm-hmm. . And so I'd say it's sort of a, a two-prong strategy where we're gonna do all the things that we need to do in terms of driving the business and driving the. The most important thing for me is that we're delivering the value proposition because if we do actually deliver on the value proposition, create a great experiences for travelers and.

[00:22:07] Um, and, uh, become more recognized and more known and more pmcs and property managers and owners feel really good, uh, about what we're doing. Uh, then the rest kind of takes care of itself, uh, and the brand will follow. And we need the right people, as you know, maybe more than, uh, yeah, the most, uh, we need the right people to make that happen for us.

[00:22:27] And so we're, we're in the steps of evolving in all directions. Uh, you know, marketing and branding is one that we have a lot of work left to do. . Um, and it's gonna come, it's gonna come in the right sequencing of events. Uh, and the, the key thing now is that we just focus completely on the product and the experience and, uh, and making sure that puts us in a position to really do the branding and maybe larger branding work that we're gonna need to do, uh, a little bit down the line.

[00:22:57] Mm-hmm. . Yeah. I, I think that, um, you, you, you said something that my personal experience in the industry. Is that the OTAs have been able to get, gain a lot of ground whenever the economy is not being favorable. . Um, I was in property management for years and then I was with Expedia, um, and then I was at Channel Management and now I'm actually with, um, Marriott Homes and Villas.

[00:23:19] Um, so I, I see that cycle and I think you guys are, you're positioned in the right place at the right time, and I think the leadership changes is, is coming at the right time. There's no telling where you can go. And I think that it's going to be very important for property managers to, we talked a lot about it this last year with a lot of guests, but you know, in really diversifying the, the distribution that you're doing, it's not so much of just doing.

[00:23:44] Airbnb or V R B O or his feeder, it's, it's not just about using two of the big ones. You really need to have some of these ones to fill in the gaps and, and I think what you guys do at one State has always been appealing to me is that you're answering a problem. That a lot of managers just, they don't have the marketing dollars to be able to throw out their last minute to be able to grab the gas.

[00:24:05] They've already spent their, you know, they've already spent their marketing dollars. So you guys can kind of come in and, and be the hero in, in that scenario. So I think for this year I'm not as, um, I, I, for me, I, I don't personally think it's gonna be as bad as like people were anticipating it to be. I think it's gonna be, it'll be, uh, you know, not a whip on the radar.

[00:24:24] It'll definitely affect people and clearly, you know, we're seeing that with companies doing layoffs, but people are still gonna travel. I mean, that's one thing that I know to be true in my entire travel experience is that people will always travel. That's, it's just a God-given, right, that they expect to be able to do.

[00:24:38] They might delay when they do it and they might be looking for a deal. So you guys are very well positioned, I think, going into this. I heard a really interesting comparison on our just prediction for what travel in 2023 is gonna be like, basically, I can't remember the guy's name, but he's kind of a like, Um, he has a, a unique way of writing on things that it is pretty funny, but he said that the difference in 2023 is just gonna be that everyone buys, uh, one to two less Patagonia vests.

[00:25:06] not, not massive problems, but you know, if you really like your Patagonia vests, like you're kind of upset that you might not have. Got two new ones this year. Right. I mean, who knows? my one because seriously. Yeah, exactly. Exactly. It's not gonna be completely taken off the radar, but yeah, I, I think, you know, Annie, like you said this, we've definitely seen this, and I know in my previous experience, um, I, when there's, when it's not the best of years, people are looking for more channels, but their properties on, they're looking for more ways to be creative and form partner.

[00:25:36] and I will say in the, in the time that I've gotten to know everybody at Wednesday, you guys are very much focused on partnerships and really working with, um, your property managers and making sure that it's, it's gonna be a good fit for them. And it's just you're a pleasant OTA to work with. I do know that

[00:25:53] So I think you, you are poised for some good success in this coming year. Yeah, for sure. And, and the, the PMs that I've, I've met with recently kind of just vocalized that directly to us, which is helps, is like, look, look, we want another advantage here. And Booking doesn't charge a fee. Tr traveler. And, and Airbnb used to charge a fee to the.

[00:26:11] Traveler in Europe and now doesn't, and tripled the, tripled the booking fees to, to property managers in, in Europe. Uh, VRBO would never, uh, uh, charge a traveler fee up until the Expedia acquisition and mm-hmm. , uh, they probably would've done it anyway, but, uh, but it was done, um, uh, in consequence with, with them buying the company and Sure.

[00:26:30] Larger take rate and all those things. And so we fit in a really nice, uh, place for folks in trying to, trying to fill that, uh, trying to fill those. . Yeah. What, what are your thoughts are, or what are your thoughts on, in the past couple years, how things have changed with companies, like a firm that give travelers the ability to pay over time?

[00:26:47] I know that's a, that's a big initiative on VRBO now, but what, what are your thoughts on that? I think it's, uh, I, I don't, um, those are are very strong businesses that have added to the mix in terms of giving consumers the choice about how they want to do. It fits into the category of how they wanna do lots of things inclusive of paying for, uh, for travel and lots of other larger purchases.

[00:27:12] And so I think for us it's, it's um, uh, there's a broad myriad of alternative payment methods. We probably had a hundred different payment methods that we offered through the capstone channel. Affirm, and Buy now, pay later as one of 'em. It's important. Um, but I think we, for us in and of itself, um, I don't think it it really is going to affect our business other than to say we need to be able to offer the broadest range of payment methods.

[00:27:40] And so if you are, uh, if you're a traveler from the Netherlands or a few other countries in Europe, we wanna be able to offer, you know, the payment, the local payment methods that that traveler wants to use. And if someone wants to pay over time and has maxed out the credit card and wants that, Um, uh, we'll, we'll offer up, uh, the firm and we, we work with them now as well, but for us, it's much more that piece of the puzzle for us is a tool in this toolkit that we just wanna be able to offer the broadest range of services.

[00:28:08] And like a lot of your guests, particularly I would imagine in the, in the OTA and, and and marketplace spaces, we really are building on those core 10 minutes that people have talked about around flexibility in all, all measures, uh, and trust and safety, uh, and. And transparency. And that's part of the, the aspect of flexibility, which for us would be, which would also be inclusive of making it easier to cancel and book and change and extend, even with the type of value proposition that we have, in addition to saying, let's give the traveler however they wanna pay for the vacation.

[00:28:40] Let's, let's give them the, uh, the flexibility to pay how they want. Right. And I think the last time that we talked to Ben, that you had a patent pending. on one of the payment methods within Win Wims Day. Is that, has that gone through or where is that? Uh, it has, yeah, around two. Uh, we'll be talking more about that as, as well specifically, but there are sort of two features, uh, done in a specific way around split pay, uh mm-hmm around the ability for, uh, uh, for multiple travelers to pay for a trip.

[00:29:08] For vacation rental, in addition to the way in which we've constructed our own internal trip chat function of the ability to communicate within the app amongst different groups of parties. And so, um, excited about those two things. Gonna be a part of the value proposition, uh, as we move, uh, continue to be a part of the value proposition as we, as we move forward.

[00:29:27] Yeah. One thing I think that's really. Exciting about what you guys have is that you, that you're growing now, but you've, um, done a lot of really great things with the small team. I was very fortunate to meet eSSH that you're, um, head of for your product and development. And I mean, I don't know, I don't know when he sleeps, honestly, cuz it seems like he's got teams all around the world.

[00:29:48] He's, he's constantly doing integration, but I think that that's one thing that's really great about a small organization is that you can be scrappy and you can just do, you know, do all these things. And as you get larger it becomes harder to, to integrate. It becomes harder to move things because you've got too many people involved in the process.

[00:30:04] I've seen that personally over my career in the larger, sometimes larger organization. It takes longer to get things done, but you guys have just done a lot of really great things. And so, um, Ben was super excited about telling us about that, uh, the, the split pay program. And I'm curious cuz I, I feel like, um, back to the payment part of it, When I was, I think it was when I was at Expedia, I learned a lot about the different payment models around the country.

[00:30:26] And it was, I think it's Brazil, like that's, they, they are kind of the, the model country for, that's the way they do everything. And it's not so much split pay, but it's like they do everything in installments and they'll buy something as small as a toaster. Um, but they're vacation. So that was something that I think Expedia did, you know, tried to integrate in, in allowing people to do that.

[00:30:46] But there's so many different payment. Types that are out there right now. And the one that comes to mind that's just been in the, you know, the news as of late is, is the Bitcoin. Like, how do you, you know, how do you decide whether you want to go into something that's unknown like that? I mean, I guess it's not as unknown as it was a year ago, but that's, I mean, know from a, from a payment perspective, from, you know, Syntec, like how do you decide what you're gonna do and what you're gonna integrate with and offer to the consumer?

[00:31:15] We have a lot of problems that we're working on and challenges of, of kind of at our stage. And so, um, the first thing for me, honestly, without even sort of joking, is like I need to be able to fully understand the payment method and how it works and how we manage not just the payment of it, but the chargeback and the refund.

[00:31:33] And it happens at different times. Cause we gotta need space where we're not just paying for. With a pair of jeans, the record, and that could get returned, but the money flows back and forth, come in different forms and maybe there's a thousand dollars refund that the owner decides to do on the, on the 2000, in the $10,000 stay and.

[00:31:51] and all of those things. And so I would say on that one specifically, uh, we're probably going to wa continue to watch and observe how that plays out. Uh, and probably won't be a part of our mix, just given the magnitude of, of other, uh, uh, I'd say more important things that we need to focus on outside of the crypto part of the equation, which may, may factor in at some point in time.

[00:32:12] But, um, I think we got, you know, plenty on our plate now. To, to deal with on and including other payment methods by the way. And so, you know, making sure that a Brazilian traveler is able to book the way they wanna book in, you know, for a whims day and in Myrtle Beach or wherever is really important. Um, but, uh, what we're probably, uh, a few ways, uh, a few years away from really thinking hard about that piece of it again, only because there's so much more, you know, for us to do.

[00:32:38] Now, how do property managers connect to you? Are you connected to all the major softwares? So like streamline track, I mean, all guesty, all all the major ones? Yeah, all the. Hundred percent of our inventory right now is sourced through those channels. And so we're integrated into, uh, there's a few stragglers out there that we are aren't, but well, we're gonna get those done in the first half of the year.

[00:33:00] There's 13 or 14 now that we're, uh, we're integrated into, and, you know, we've got properties in, in, uh, in Canada and Mexico as well. And we're gonna be launching in, in Europe sometime in, in 2023 through, through some, uh, European partners on the software side of the thing. But yeah, that's a hundred percent of our inventory comes through that channel today.

[00:33:20] Okay, great. Do you see yourselves offering, I've seen some channels, um, offer sort of a, a self-serve model to, for like individual owners that have a unit or two. Are you gonna be offering anything like that? We, we, um, We'll, probably we, we are, uh, we, yes, this is a short answer, , and so there's lots of cool things that we're working on, on the roadmap, and it's a really big market opportunity.

[00:33:45] And back to the mission statement, we wanna serve not just the property management companies that, you know, uh, we just spoke about with Alex, uh, that are integrated into all those softwares, but any property. Who wants and needs that value proposition, which is, I wanna fail Knight, I wanna, I wanna attract more guests, incremental bookings.

[00:34:06] I don't wanna pave this or that fee to HomeAway or to to vrbo or to, or to Airbnb. Uh, so the short answer is, uh, along the journey of what it is that we're doing, uh, we wanna be able to serve both property management companies and the millions and millions of property owners around the country. . Uh, and there's several initiatives sort of in the works now in order for us to be able to do that.

[00:34:30] Thank you. You've talked, uh, or you've mentioned a few times now about how important the people are that you have on the team to make all of this happen. Yeah. And I know Ben talked a lot about that too, and you can tell he's definitely somebody that really leads from the hard as probably set that up as the future of what the company will continue to be under your leadership.

[00:34:48] But tell us a little bit about the culture and how important that is. In your experience that you've learned from these other companies you've worked with, you know, how do you continue to grow that culture within Wim State to make it just the best place for people to work and be proud of Passion and ity, , and you have those two things and everybody kind of drinking outta the same goblet, then you're kind of, you got the makings of a really special team you met, you know, uh, Annie mentioned, you know, k.

[00:35:18] I'm not sure if he falls into the personnel category, cuz I think he's actually like a side ward. And so the way in which he works and, and, and the dedication and what he's put towards this effort. And one of the things I was just really pleasantly surprised about, there was a lot of that in the building outside of Ben, where there was a collection.

[00:35:36] Uh, and it's hard, it's a hard thing to get, to get right in the beginning because it's the beginning and it's risky and blah, blah. There are a number of people across, uh, the platform who fall into that category. And the folks, those six key new hires that we're bringing into the, uh, fold over the next month or so, these are all per people who used to work, uh, for me, or there's one or two degrees of separation.

[00:36:00] We, we all have a similar d n A. Um, I worked in multiple, multiple environments. Where I did not enjoy the people part of the experience and things often just didn't work purely due to even at great companies, just great products cuz people, issues got in the way of all types, uh, up and down. Uh, that's probably not worth getting getting into, but we've got the, making sea of a really special culture and it, it, it's, uh, it's, it's further, um, yeah, uh, you know, it's further.

[00:36:34] Or it's, it elevates by just the virtue of people, uh, people's actions and how they talk to each other and how they work and their work habits and how they treat each other. Um, and so it's gonna be really, really important to us and really important to me that we keep this thing that Ben started in place, which is amazing.

[00:36:56] People who having great talent and capability to do marketing and engineering and Zillows. And all of those different things, but they really, uh, I, we want them to fit the mold of, like, this, these are the people that we're gonna link arms to. We're gonna be in a foxhole. The degree of difficulty, as you guys know, is really, really high for what we're doing.

[00:37:15] Mm-hmm. and, uh, and the ability to work through crisis, crisis after crisis after stuff breaking after this and this and that is, it takes a certain type of person with a certain type of dna. To, to really thrive and just wanna be a, a part of something like that. So it's a really, really important thing to me that we're gonna try to continue to get right, uh, because, uh, one outta necessity.

[00:37:39] But just because, because I've had experience with such bad experiences in the past and other types of businesses that, okay, now I have the opportunity to have more influence around making sure that we've got the right people and the right culture in the building who do things the right. Yeah. Yeah, I know in my new role at casa, I've really gotten to see, to see how important culture is, and I've never worked in a company like this that values it as much as they do.

[00:38:05] And it's such an, it's such a difference. I mean, you just, the, the interactions that you have with people and. Just like you said, the passion. When people are passionate about what they do, they're gonna take ownership of what they do, and it's, you know, it just, it, it builds something bigger than, than who you are individually.

[00:38:21] And it just, it builds that teamwork mentality and it's, it's hard to describe. I think that's the hardest thing about culture is you can't just describe what it is. It is a feeling. And that's where a lot of companies just get it wrong because they say, okay, this is what we say is important to us and these are our values and this is our mission statement.

[00:38:39] And that's what it is. But it's not about the words on a paper, it's, it's how about how you make people feel that they're valued and that they're part of contributing to this and. that, yeah, there's, this is a complex business, whether you're on the property management side or the software side, that services us.

[00:38:54] There's a lot of moving parts and a lot of things that are constantly evolving and changing, and you've gotta have those people that are passionate about it that are gonna be able to stick through that, but Oh, totally. It sounds like, it sounds like you have . Oh, totally. Well, none of the words. I totally agree.

[00:39:07] And like, uh, have religion. Regardless of what I say and regardless of what I put down on paper, you just have to be in the room. It's the only description one, whether Yeah, you got it right or close to right, or, or your version of right. Without sort of being at a strategy session or the drinks party or the interview process or whatever to really get it, uh, and have any type of authentic view of like, okay, this is a unique culture, and, and, uh, I can, I can see how these, these folks.

[00:39:38] Yeah. Yeah. I did wanna ask you, um, cuz I think it's, the culture is really important. Um, but as an ota one of the things that I think OTAs have struggled from is that perception of the guest and being able to control the kind of guest that comes through, but also controlling. We're vetting out the property so that guests are getting, you know, you can deliver on the expectation from the guest side.

[00:40:01] So there's been a lot of talk about some of the channels out there that just let anybody and everybody list their units and, you know, and, and kind of going back to if you're gonna bring on smaller groups or, you know, not. I would say not professionally. What would we consider professional management companies?

[00:40:17] How do you guys see that ability to scale? Because again, there is so much riding or, or, or resting in that large space of individual owners. There's a lot of units that sit out there in terms of inventory and some markets bigger than others, but there are a lot harder to sort of, um, get them to. An understanding of standards and deliverable expectations to the guests.

[00:40:39] So how do you see the Wednesday's role in that helping professionalize some of those managers as you scale? Well, it's just one of those unique, uh, uh, you know, I go back to my capstone experience because again, after buildings, because we didn't ha in when we first started with Herbo, we didn't have the systems and the technology and the people in place to manage a million property owners.

[00:41:03] and we really didn't even have all of that in place on the soft integrated software, property management company business because within our four or 5,000 property manager customers, there are a lot of properties within that, within that space. And so one of the useful things that I've brought to, I'd like to think I brought to the table here is we be, we built a cross functions, a whole series.

[00:41:25] Protections and checks and vendors and, uh, technology improvements and enhancements and communications. And for us, it's really both sides of the transaction. It's, it's doing what you're, you're saying, Annie, which is, which is, um, giving some level of comfort to guests that they're saying in a safe place.

[00:41:43] That these are, um, uh, that the, these are, you know, legitimate, not just legitimate, but great experienced ratings, reviews, properties and, and partner. . It's equally as a point for us that we're doing the same with with guests because in much so than in, for me in vacation rentals, it's far more common, I would say, than in hotels to say, look, I'd rather, I'd much rather maybe have my house on rented if I don't feel like completely good about the guests that's gonna stay in it.

[00:42:14] And so, mm-hmm. , we're, we are, we've got more work to do. But I think part of. , uh, the historical context I have is, is the types of partners who we need to work with and the technology that we need to build and the services we need to have to really protect both sides of the transaction, which is making sure that we have good travelers and making sure that we have good property managers and property owners.

[00:42:36] We've got more work to do, but I think we've got a good path forward on that. Uh, cuz we had to build it all for scratch for the most part over the seven or eight years I was at Capstone. It's, that's so important as it plays into, um, you know, very hot topic within the industry regulations. And I think, you know, that the channels are even need to make sure that they are taking a look at not just the gas, but also that the properties that they're listing.

[00:43:03] Because I think, I don't know that we've had as much in, in the us I've seen, um, a, a good friend of ours and, uh, of the show, um, Chris Mogan with I. You know, he's very passionate about making sure that properties are certified and that managers are certified because he's seen firsthand some of the things in Europe where people have spent their entire life savings to go run a villa and get there, and there's no villa.

[00:43:26] You know? And so it, it's just mind boggling that there are people that do this, but again, there's always, there's a bad apple in every bunch. And it's just, you know, us as an industry trying to make sure that we can get those bad apples out, whether it be a bad manager, um, or, or, you know, a bad guess. We wanna work together on.

[00:43:43] Yeah, for sure. The, you know, the regulatory piece is, is so important. I'm really, uh, happy to be associated with. With the ver advocacy part, but also just as a pavement company. Again, the former experience, the fact of going through and getting licensed ourselves and being, uh, uh, being, uh, at the, not at the mercy, but we had a very significant burden even given the size of the former company, uh, to be licensed in North America and Europe.

[00:44:05] And it meant, it meant needing to put in controls into the business that we wouldn't have had to otherwise had we not been licensed. . And so the combination of those two things, I, I completely agree. Um, particularly for us. , you know, we, if we get that one wrong, we, we, it's gonna be really difficult for a company like ours.

[00:44:24] And so we even be more, uh, everybody needs to be super prepared for it and be thoughtful about how they deal with it. But for smaller companies, maybe even more so, because, you know, most people know who Airbnb is, apparently. Mm-hmm. , uh, uh, and and, and Expedia and those great businesses. Um, and maybe they're less.

[00:44:42] With us. So, so it's really important for us to get that one right. Uh, but it's, but I also understand the degree of difficulty in that one specifically cuz it's, it's hard to do and, uh, there are a lot of humans out there. Yeah. Well, it looks like, and it sounds like it's gonna be a really exciting year for Wims Day and certainly for, for you to be part of this journey.

[00:45:01] Now it's only been a few months and it sounds like you've already made a lot of progress and I'm just going in a great direction. We very much appreciate you coming to, to meet with us today and being able to learn more about the process and what's, what's coming up. So excited to watch the Journey

[00:45:17] Thank you so much for having me. I real, I really appreciate it. Yeah. Oh, you're on mute. Congratulations on your new role, David. That's really exciting. So, you're just a few days into being c e o. Any big, any big movement that you gotta, any big announcements that you need to make in the next couple of weeks that you wanna tell us what I'll get out on this, might as well get it out now.

[00:45:40] Uh, well, I, I. The short answer is there's gonna be some great ones, and I'd say look out for a really cool partnership announcement. Look out for some real, a really great new hire announcement, uh, and look out for some really cool stuff around this sort of broadened market opportunity around expanding the mission beyond just the last minute booking window to these other, uh, other parts of the calendar where we think we, uh, there's a, there's a reason for whims day to exist in those points, uh, and the calendar during the year as well.

[00:46:09] Awesome. Sounds exciting. Yeah, I know. I, I can't wait to hear what the partnership is. That's really cool. Yeah, we'll look forward to seeing that on LinkedIn here soon. , no problem with the mute thing. Uh, Annie, I have my best conversations with myself. , right. Oh, David, if anybody wants to get in touch with you, what's the best way for them to reach you?

[00:46:28] Uh, David dot Weiss, w e i s s wim Uh, LinkedIn, or, um, uh, those are the two best, uh, the two best. Okay, great. And if anybody wants to contact Annie and I, you can go to Alex and annie If you're enjoying the show, we'd love to hear from you. We'd love getting, um, reviews and comments and just, um, connecting with our audience.

[00:46:50] So you can do that right on the website or whichever app that you listen to podcasts on. And until next time, thank you everybody for tuning in. Thanks. Take care. Thanks.

David WeissProfile Photo

David Weiss


David Weiss joined Whimstay in August 2022 as Chief Operating Officer, and he was recently appointed Chief Executive Officer and member of Whimstay’s Board of Directors effective January 1, 2023. Prior to Whimstay, Weiss worked at Reverence Capital Partners and Aquiline Capital Partners, advising on Travel Tech and Prop Tech M&A, in addition to leading operational initiatives for certain of the firms’ portfolio companies. Prior to that, Weiss served as President of Yapstone from 2013 through June 2020, a leading fintech/payments company focused on the Travel and Real Estate sectors that scaled from $60m in revenue to over $150m in revenue during his tenure. At Yapstone, Weiss led teams that built and operated Vrbo’s end-to-end payments experience, grew global volume to $8 billion, onboarded and provided payouts, including faster payouts, to roughly 1 million Vrbo property owners in North America and Europe, offered payment methods and ancillary services to travelers worldwide, and in addition, launched fraud prevention, chargeback management, compliance, and licensing services. Weiss also led teams that established integrations with most of the major vacation rental software companies and processed over $5 billion in annual payments volume for leading vacation rental property management companies in North America and Europe.

Prior to Yapstone, Weiss spent 20 years in investment banking covering several sectors including Travel Tech, Prop Tech, and Sustainability, advising CEO’s, COO’s, CFO’s, boards of directors, as well as private equity and venture capital firms, on a broad range of capital raising, M&A, and strategic advisory engagements.