David Litwak:
Hello, everyone. Thanks for joining us today. This is how I got here Mozilla and focus wires podcast about innovators in travel and transportation. Today we’re joined by Caitlin Zeno Vaughn during from Portland Salle Porter and se was founded in 2015 by Caitlin and Deepak Srivastava, with a focus on building technology support local independent hotels. Thanks for joining us, Caitlin. Thanks for having me. So we’d like to start every one of these podcasts out the exact same way, which is to ask you how you got here.

Caitlin Zaino von During:
Yeah, so partner and sale was founded in 2015. I had been originally working for the United Nations traveling a ton staying in amazing hotels, and feeling like I was having these incredible experiences on property. And then when I would try to explore the city or connect with the property itself, I was really left feeling flat. They would give me like a printed piece of paper. They’re like, this is where you should go out to eat. So we thought, Man, isn’t there a way to sort of redefine the concierge For today’s traveler, I’m on my phone, my friends are on my phone. We’re all emailing a time. So that’s the premise of the idea originally with Porter and say, Let’s meet the modern traveler where they were. And then as we dove into hospitality, we were just blown away, like how much innovation had yet to come to the hospitality space. And we felt like hotels could really benefit from modern tech. And so we built over five years, different assets and tools to connect amazing hotels with this sort of modern traveler, a concierge app. But we’ll check in mobile check out keyless entry, authentic destination content to explore a city and then on top of that pre arrival ecommerce sort of experiences where a guess could really curate and create their own sort of bespoke stay. So we spent five years connecting hotel and traveler and then Coronavirus, hit and we sunset all of those products and today are really focusing on an e commerce platform. That allows consumers to bank incredible deals at the world’s very best hotels, and the only hitches that you either travel now or you travel anytime in the future for the next two years. So you bank up to 50% off. And the price is sort of a variable, your voucher is what it is. And you travel when you’re ready.

David Litwak:
Cool. Well, thanks for the summary there. So one of the reasons why I was interested in getting you on our podcast is because there’s not as much of a focus on the fact that there’s a huge long tail of small hotels out there. And recently, there has been more technology companies addressing that, how you can actually provide a good really good digital booking experience to these boutique hotels that maybe a Marriott can’t afford, maybe But Mary could afford but these guys can’t. And making it possible to have them actually compete with Expedia is of the world. I’d love for you to just like delve a little bit more into each of those tools you built up until grown right

Caitlin Zaino von During:
Well, that was it right? Like we saw that you had these amazing hotels, let’s take like Conservatorium in Amsterdam, right? Like, ADR was 600 plus a night. I mean, it’s a really, it’s a really upper upscale property. It’s an amazing property. And yet, that’s a really small collection or a collection of hotels where they were struggling to create digital products that would support their traveler, and yet that guest was coming in with the expectation that the hotel would have a whole suite of technology. I mean, if you can order your grocery stores on your phone, if you can do everything on your phone, why would you say the world’s best hotels and not being able to like engage with that property in a digital aspect? So for us, we were like, okay, so unless you’re a big brand, you’re not able to touch technology. And on top of it, we felt like hotels that were we’re doing it in a really clunky manner, because it’s hospitality. It’s like heads on beds, it’s not tech. And so we could come in and we can create something that really felt from a lifestyle perspective, aspirational and warm. And amazing, and yet had really incredible technology that was best in class to actually do what it was supposed to do from the hotel’s perspective, which was to provide the user with an incredible experience through technology, as they would any touch point. It was high touch high tech, and we really leaned on trying to empower but you can independent hotels to play at that level. Plus, you have like, online travel agencies that take tons of data, don’t share that with the hotel. And we were hearing hotels being like, you go outside of the lobby, it’s the black hole. We don’t know where you’re going, what you’re doing. So we also wanted to capture loads of data and be able to deliver that back to the hotels were like, we’re fighting for the hotels, we’re standing for the independent hotel to really meaningfully play in this space.

David Litwak:
So how did it go? So I mean, you pivoted a lot, you know, during Coronavirus, so it sounds like and I think this is often a problem with working with independent hotels. It’s like herding cats. Like everyone has a different you know preference. I’m guessing that might be one of the reasons why you pivoted. But I am curious.

Caitlin Zaino von During:
Yeah, I feel like herding cats is an understatement.

Look, we we took off pretty fast like 2015 we were piloting we were piloting an amazing hotels like so house. I don’t know why they were looking at us, but they did. And they gave us a shot. And we did amazing. We bought in 2016, a competitor called guests driven out of Montreal. That’s where we brought in our e commerce play. We they had a team of 50 and a huge warehouse in Montreal. We had what 10 people working for Porter in sale and we’ve doubled the revenue. We were driving on e commerce because they were doing like a whole spray and pray. Let’s sell bottomless sodas and we were like, nope, let’s sell upsells to luxury suites. Let’s sell big ticket items. Let’s go to hotels that have higher ad hours and higher average basket size. We’re going to get way more bang for our buck. And we did. And so through the e commerce platform and through the concierge app We were doing incredibly well and had a ton of growth. We’ve got great partnerships, folks like design hotels, what we saw in probably 2019 was a plateau that like, everyone was kind of over it, everyone was kind of over an app, everyone was kind of over the whole experience, hotels were being able to like, figure out how to do this in new ways. And so we were, we felt like we needed to move anyway. And we were in the process of building a very personalized recommendation engine. We were like, we’re going to build the Warby Parker for online travel booking, meaning it’s going to be hyper personalized super lifestyle, it’s going to focus on this next generation of travelers. We felt like travel, the next generation of travelers felt connected to a hotel tonight or an Airbnb, but they’re not they weren’t feeling connected to Expedia or even a tablet, right. So can we build that brand that would create that kind of trust and create a really cool tech experience that would allow you to not go to 38 booking sites before you make a choice? But to really hone in and almost like a dating site match the consumer with their very best hotel. We were booking that we were building that excuse me, and then Coronavirus hit. So we just like just completely stopped building that. Um, so it was it was great for a while. And then once we hit that plateau, we were like if we want to stay relevant and travel, we need to figure out essentially how we’re going to drive a volume of meaningful guests to these properties and frankly, make hotel sexy again, like why is Airbnb winning Airbnb? At the I think the product itself kind of sucks. Like I don’t want to sleep in some guy’s house I want I want to stay in a hotel hotels are awesome. So our whole thing was like we’re going to continue to fight for the hotel. They just need help in in creating meaningful technology for today’s guests.

David Litwak:
So it’s interesting, you mentioned Warby Parker and Warby Parker is known for a lot of things. But one of the biggest is brands and kind of this this new wave of you know, kind of CPG brands but it’s that I think it’s an impression you use immediately get it from your site you have these influencers and tastemakers on your website, your branding overall it does, I think ironically actually really embrace the reason why so many travel entrepreneurs get into travel as they think it’s going to be the Amsterdam Conservatorium experience, not the dealing with back end GDS is so you like, what I found interesting, like, was this focus of yours on the brand? And I thought that you know, like, it seemed like you were almost trying to put like a sort of Alliance on top of many of these independent hotels and and it reminded me of kind of some of the you see these Everyone’s so these alliances were people, they they band together mostly so that like they’re all independently owned, but they have some central system. Is that was that part of the angle as well?

Caitlin Zaino von During:
Oh, definitely. Totally. All of that. And that’s the thing like we wanted, if you’re doing if you’re working with these amazing hotels, you know, throwing around these names. The brand has to be there, right because they’re not even going to look at it if the hotel itself will not look at the product if it’s not representative of a brand that they can get behind the consumer, why you’re traveling and why you want to travel these amazing responses. It’s a lot of it is aspiration. It’s a home that’s better than yours, living a life that’s better than yours for a moment. So we really leaned into it has to be sexy, it has to be beautiful. It has to be author, aspirational. And then bring everyone together for sure. And sort of this Co Op collective experience, right like a small luxury hotels experience. But again, let’s contemporize it a little bit, a leading hotels of the world, but with that modern edge untwist So, we definitely felt like an especially post pandemic. Let’s bring these amazing hotels together in one collective let’s create this incredible brand offering let’s introduce all these hotels to new audiences open up new distribution streams and platforms and really have a powerful network effect globally of the world’s best hotels. So That was the strategy was interesting. Just for a second to lean into your point about the GDS. It was sort of a double edged sword and continues to be for us because we were so brand focused, that hotel’s them think it’s almost like we’re too pretty then they think that we’re not smart, right? They’ll be like, but and so we always have to back it up with like, Yes, we have some Nexus certification, I’m a data certification. Yes, we can connect to your PMS or we understand the POS system. And they don’t always believe like, we have the tech checks because we look so pretty. So we ended up having to go to battle with someone like a normal one or we used to historically, which feels like a very different product because it’s almost like they were no offense to nor one. They were boring, but they’re functional. They get it. You guys are pretty but you actually get it. I mean, we

Kevin May:
did. That’s good. That’s great. Hi, Caitlin. It’s Kev here. Thanks so much for joining us. So I’m always interested in the origin stories with around companies there’s there’s often a very dark diverse way that David and I kind of tackle these interviews. I’m always quite interested in the kind of the makeup and how things came together. I mean, it’s, you said, the tech chops in your last answer there. And I’m kind of curious. I mean, your background is in the UN and you worked for the BBC for a while. And Deepak your co founder was Dropbox and more in the banking industry. Morgan Stanley. Right. So how, first of all, how did you two get together to form the business? And how did you get your tech chops so quickly in order to solve the problem that you you thought needed solving?

Caitlin Zaino von During:
Yeah. Right. Yeah, there was uncertainty in hospitality, like, you have to learn the discourse of hospitality. So it’s the tech side and the hospitality side, right. So we’ll want to put our team for sure. So I can talk about our CTO and our director of product. But for us, so I had a startup prior to Porter and sale called the urban grocer. It started as a blog turned into a content discovery platform. I then sold it as a television show to cooking channel. And it was all about like, Cool food trends that were intersecting with art and pop culture. And when I sold it to cooking channel, I was introduced to a woman that worked there. Her name was Momoko. And I was like, I’m looking for co founder on the urban grocer, because I want to sort of grow that into a business. It was a blog that kind of took off and I want to do something with it. And so her and I teamed up. And within two days of teaming up, we retired the urban grocer and actually pivoted to Porter and sail. And Momo and I worked together for about six months pretty hardcore. But she was moving to Tokyo, she moved to Tokyo, and in the process introduced me to her friend from college, which was Deepak and Deepak had all of the finance background at the time, we just needed to raise money. So we were like, I need someone that can think in that fashion. Like I knew content and I new technology because the urban grocer was a blog that I developed into a website then we can I mean this Since like 2010 when blogs were the thing, so I learned a lot I learned how to do it like it’s all WordPress but like I learned a lot in that process about creating technology that meaningfully engages a consumer that create you create editorial that has a depth of engagement to inspire or to lead to a transaction or an action. So a lot of that I learned during the era grosser Kibaki men, he helped us raise money. Then we just hired an awesome tech team. So our CTO, she has been in technology for like 20 years worked for a company that sold to Travelocity built company has built tech teams and companies that then exited. So she came with both a tech background obviously, that was pretty deep, but also within travel and even the OTC space. And then, our Director of Product was at MIT and Amazon. So we brought in the best tech talent that we could find or afford,

Kevin May:
was it through the CTO that you’ve got yourself? Connect your early kind of connections to the hotels as customers because you know coming in cold without any travel experience, if you didn’t have her forging those relationships with the hotels early on would argue been been quite a tough task, or did she help with that?

Caitlin Zaino von During:
She didn’t help with that. I’m a hustler. I did all of it. I don’t. Excellent. Yeah. I’m Momoko my first co founder was super connected. So she would like and Deepak By the way, also super connected Deepak if you’ve met him. I mean, David, you said this earlier, like you’ve met Deepak once, like you will be friends with him for the next 40 years. So we had sort of a breath of connections, and then I just went and sold the shit out of it as best they could with a prototype on an iPad. And that worked somehow. And that’s the thing that people were hot on. Check at the time because they were trying to put iPads in rooms and I was like, no one’s putting an iPod in your pocket. Put good tech on the phone. Don’t tell me where the boardroom is with an app. I don’t care where the boardroom is. Tell me Tell me something that’s going to solve a guest pain point. And so I created, we created that technology. And because of the brand, we’re able to get some early interest, and then grew that traction.

Kevin May:
It’s interesting you it’s what you’re saying about the kind of the hotel requirements even in those early days, you know, a lot of it was about content and providing a nice concierge service. But was there already a pressure on Actually, this concierge service also needs to make some money as well. So we’re thinking about ancillary revenue and things like that, or was that a secondary part of it? Do you think?

Caitlin Zaino von During:
It definitely happened? It was secondary, but so when we first launched it was like, I was still talking to consumers in 2014 2015. Like early days, pre launch, I was literally having conversations with the concierge. Now who, who has a concierge? I mean, it’s not it’s not there in the same way. Um, but then we were, we did well, and we would say to hotels, you know, your average guest is in the app for 30 minutes. What would you Do if you had 30 minutes to talk to your guests? What are you telling them?

Kevin May:
So just on that 30 minutes is that per day or per length of stay, because that’s an incredible step,

Caitlin Zaino von During:
per length of stay. So it was usually a half days, they would go back in four or five times and spend 567 minutes a session.

Kevin May:
Let’s do that. Okay,

that still seems quite a lot though them but a good a good opportunity to do all those other kinds of things that that you ordinarily would have to deal with at the desk, or as you say, with the concierge, right?

Caitlin Zaino von During:
Well, this is it exactly. So like, I remember saying that to a large hospitality brand was in a meeting and they kind of scoff at that. And they’re like, the only reason somebody spent 30 minutes in our app is if they leave it open on accident. So like, we we got it. We knew how to solve the guest pain point. We weren’t telling them. You know, here’s stupid information you don’t need. We were telling them information that they were eating up so we had an opportunity to then sell them something But in early days, we weren’t selling them anything we were just engaging. And so we thought the hotels would be really down for all the data that we had, but they just didn’t know what to do with it. So that’s where the guests driven acquisition became really important, because that was all right now I’ve got their attention. Now we need to get them to purchase. And so through the test driven acquisition, we added on this sort of pre arrival component, but that was also pretty game changing for us because it didn’t, it necessitated linking hooking into the PMS. So now we were getting guest records every morning and able to convert them to pre arrival, and then on top of it to the full app experience. So that really was pretty game changing for us. And we were able to own sort of that entire guest journey post booking.

David Litwak:
So I want to just go back to something you said you said you guys reached a plateau as I think the word you use. So he said people like our hotels were kind of over it. Could you elaborate on that a little bit? And I have a couple follow up questions, but

Caitlin Zaino von During:
it was interesting. Because the I guess like this, the sexiness or the appeal of the modern con Sears was sort of like there now you the whole I think novelty and why we first came about of connecting the hotel and guests they were finding other ways to do that even through like an Instagram right like different ways of connecting with their consumer that they were having success with. And so they were asking all of a sudden for check in and check out which was great except that every government has a different regulation for security at a hotel, let’s say or every hotel has a different set of criteria to do keyless entry. Everybody wants to kill a century we built keyless entry, but no, the hotels didn’t use it and the guests and music so like they’re all of a sudden they’re like, okay, now what we want from technology is all this functionality. But at the end of the day because hotel software systems are so closed and because the hotels are still so operationally human driven. It became really hard to actually have meaningful technical replaced some of that function. And so they thought that they wanted it and we would build it, but it wouldn’t really work. And so it became we lost sort of product market fit, I think in 2019, which made it harder for us to sell meaningfully, right? Because we were driving revenue. Yeah, but the revenue wasn’t game changing. And we had technology gap, but the technology wasn’t game changing. And then we could, we could build out new systems and products, but they were expensive and consumers weren’t using them. So it became a really tough proposition for us to figure out like, what is the future of travel? And so we’re big believers of like the future is what you the best way to predict the future is to invent it. So we were like, forget the hotel, can’t listen to them anymore. We have to go back to the 2015 mentality of hotels don’t get it let’s see the future for them and build something that will fundamentally have an impact and that will be on like filling rooms but with a meaningful guests and extend the lifetime value. That gas through the different mechanisms and learnings and product suite that we had. So that’s kind of where we were going. We were trying to figure out how do you connect to the new guest experience and define the future of travel.

David Litwak:
So it’s funny that reminds me about like, you know, mozilo, we aggregate different forms of ground transportation. And before Uber, there was taxi magic and taxi magic tried to work with individual taxi companies, and they gave them tracking software, because they said they wanted the tracking software, when you use the tracking software, a lot of what you’re saying actually reminds me, like the whole thing only really worked actually, when they wholesale throughout all this relationship and decided to rebuild it from the ground up. And I think of almost like, the equivalent in your industry is like a saunder or something like that. It goes like oh, you know, you don’t want to adopt keyless entry. Well, we’re forcing you to that keyless entry, because there’s no one at the front who is going to do it. And it forces that and mozilo is that different philosophy, I think maybe something more aligned with yours or we’ve realized, okay, we need to know exactly where we can make someone do something we want them to do and where it’s just not going to work. It sounds like you guys came to that conclusion is like these guys are independent, they’re not going to really conform to certain things we need them to do. So let’s change strategy. And I’m curious, like, if you have any recommendations for people who want to work with independent hotels on, you know, like, what they need to avoid, and what are those underlying dynamics that you kind of didn’t understand that you do now?

Caitlin Zaino von During:
Yeah, definitely. I think, oh, man, it’s important to realize how desperate the industry is, like every hotel, especially at the independent level will operate differently. It’s different systems and software’s I mean, like 80% of hotels will use opera but then there’s protel. Then there’s regional, like HMS RMS like so. You really didn’t like Impala that started about in the UK, but they’re trying to create sort of a black box that connects with all that like, that’s sort of where you want to be. You don’t want to try and play at the ground level super micro like hotel over hotel because you can’t like because of how different it is. You have to Almost look at it a macro level view and how do you the way that we see it is how do you productize something rather than go project by project. Because if you fall into a trap where you’re trying to build something for hotels, and you end up listening to every hotel and building for that hotel, you’re just an agency. And so when you think about scale, you can’t scale in the industry, unless you go macro and find solutions that can be applied within the context and leaning into the consideration that everyone operates differently. Like you have to accept that as the reality the condition with what you’re working in and not make your company like rely on conformity. You have to build the conformity into the company. Does that make sense?

David Litwak:
Yeah, no, no, absolutely. I think you need to like figure out where that line is, you know, between overly customization and saying okay, well, this country this system, this PMS system, this that for, you know, like literally your first 10 clients, all of you to build something awesome. For everyone, and you can’t get a startup off the ground like that. No, I got it. Yeah. I’m also fascinated by this pivot though, because it sounds like you guys made the right decision. But the fascinating part to me isn’t even necessarily the business side, but the emotional choice to throw out something you’ve been working on for five years. And I see this consistently with startup founders ride their failing business into the ground for 10 years and because it is making some money and and yeah, like, I’m curious, how did you deal with that psychologically?

Caitlin Zaino von During:
I think Okay, so first, like complete acknowledgement of the major public health loss and economic loss of the of the pandemic, but we were in many ways saved by that environment that we had an opportunity then within that environment to throw everything out like we could have. What we were trying to do before was slowly sunset those products while building out a new product with a very Limited team. And that became very, very hard to maintain what the pandemic kind of allowed us to do is hotel stopped, like, everything stopped. And while that was scary, that gave us a moment to do something new because there was all of a sudden no expectation. hotels were dealing with their own shit like everybody was trying to pay their mortgage. So our moment I mean, from the from the time that travel halted till we launched this product was 10 days. I mean, it was I mean, we launched the product, we decided to launch it in 48 hours had launched it, like 48 hours later launched it, but the sort of steps of with with which we realized hotels are shutting down hotels are now hospitals, like travel is stopped. All of that sort of happened in in very fast succession. And then we realized I think our company is dead. And so we need to rebuild a new company. And we were able to rebuild a new company because we had this moment where nobody was paying attention or wanted us anyway. And so we got lucky. Because we, because we did what we always tried to do, which is really solve the problem. And so we’re like, okay, hotels can’t pay their mortgages, and they need to bring cash in. But nobody can come into the door. So how do you sell a hotel room when the hotel is closed, and that was hotel credits, you just sell it later. And you incentivize the guests to purchase travel in an unpredictable environment by giving them a massive discount on something that’s never discounted. So you can save the world’s best hotel and save 35% 50%. But you have to buy it now. And you have to pay it now. And it’s non refundable. Now, in the environment where no one can travel, there’s a major virus in the world is ending. So we got consumers to do that. We drove over $115,000 in sales in like an eight week period, while hotels were closed during an economic downturn, because consumers still had a desire to travel and they knew they would Travel again, they just weren’t going to do it right now. And so in doing that we solved a major problem for hotels because they were closed. And we represented the only cash flow for many hotels in April and May like the only cash flow. And we went from three hotels that we launched with to 100 hotels in less than 90 days where it took us about 18 months for the same growth in our old business in the legacy product.

Kevin May:
Now, what’s interesting, you know, and it’s it’s a really interesting story, what you did so quickly, the reasons why you did it and those kinds of things, but you would have had existing partnerships with hotels for using the old product. So talk us through kind of the unraveling of that because you’ve gone from something else or was or was it kind of slowly on the decline anyway and you things just kind of naturally came to an end? That’s the first question so answer that I’ve gotten another one for years.

Caitlin Zaino von During:
It’s been slowly come to an end. That’s where like, we got this reprieve when the virus happened because we were like, man, we have to keep on servicing these clients. But we know we need to shift our product. And so when they when guests coming in, we were like, there’s no guests coming in. So let’s shut everything off. And at first, we said, we’re going to pause all we’re going to defer all of your fees. Like because they’d be paid, we get a commission off of a part of a transaction or whatever. So or, like people pay us aspi hotels or pay a SAS fee for the concierge product. So we were like defer your fees until June. And then three days later, we had to send out another message because hotels just shut down and we were like, all all, all fees are just paused. And then we had to send another message like a day later that said, The product is shut down. So it wasn’t it wasn’t slow because nobody was coming. So nobody was using it. And we just said we can’t continue to serve as a product that no one is using. Everything is sunset until further notice. And then we only started to open up As our hotels only started to open up from our client base over the past two or three weeks, and we only let our hotel clients know, on Friday, like this past Friday that we weren’t re engaged, we weren’t building out the new product. That wasn’t gonna continue. It was officially retired. So it was a pretty quick process overall, but we felt like we have the potential to make more money with this product for those partners. So we didn’t feel bad because if you’re making $100,000 over a year with our old product, you could at least make that with the new product, if not more,

Kevin May:
or you’re not tempted. If in a couple of months time or your hotel customers come back and say, Oh, we really missed the concierge thing. Can you resurrect it? Is that something that you might have to reconsider doing because the demand is there because presumably it was a good product before and they will want to carry on using it. Now that they’ve got great occupancy from the other products of yours that they’re using.

Caitlin Zaino von During:
Totally tempted. And I think like you were saying, like, we’ll have a product go for 10 years like, and if I just looked at the app the other day, I was like, it’s so pretty, like it’s such a, they love it so much. And then you look at like the unit economics and the how much account management it took and how we were, you know, the margins were so thin. So if that is less tempting, when we look at, we had to terminate, we had a team of 20. Now we have a team of six, including to two co founders, so really just float for full time staff, plus, Deepak and I, and we’re making more money moving faster, growing faster, having higher margins, faster, better customer acquisition, like from a pure business perspective, this is a better business. But it’s it is hard to let go of, of the work that we had done. What’s even more hard is reading all the articles that who tells when everything to be contactless and we were doing that and that’s it. Like what moneymaker was supposed to be. And so it is hard to know. Not go after that opportunity.

Kevin May:
Yeah. I mean, it’s it’s a fascinating story kailyn I mean, you within the space of five, nearly six years or whatever, you know, you’ve, you’ve launched the business you’ve pivoted, and you’ve gone through and you’re you’re soldiering through this crisis at the moment, if we can just go back a couple of years to another, you know, another important milestone in any kind of startups life, which is an acquisition when you bought guests driven in late 2016, early 2017. That’s right. I remember I remember writing about it, I’m just looking at the story I read all those years ago. And, you know, how did you how did you kind of approach that acquisition? How did it come about?

Caitlin Zaino von During:
Um, they emailed us and like guess driven emails and I’m sure they were emailing everyone. Um, you know, and so they reached out to us and Deepak you had mentioned work for Morgan Stanley. Luckily, he worked at m&a for Morgan Stanley, and so Deepak could run 1000 m&a is not 1000. But that was what he did, right? And so I got it and I was like, oh, man, they’re a competitor and they’re for sale. This is really wild. What, like, we should have a conversation, if nothing else just to do a market check and see what’s up. And Tupac was like, No, no, I think we can do it, and was able to, like persevere through that entire acquisition. And he really is the architect behind all of it. We got really lucky. I think everybody else, they had a few different folks that were looking at it and those folks ended up not following through. There were some, you know, when you kind of dug beneath the surface of that company, there was a lot of great stuff. And there was a lot of baggage that came along with it, as you know, any company that’s been around for a long time. So we gave them a price that accounted for that baggage and we were able to move quickly and we paid all cash and so it’s sort of like, you know, are we going to get a mortgage or are we going to give Do a briefcase of cash and that briefcase, kind of like did the talking for us, even if it was lower than the price would have been? had we done some sort of like, you know, founder staying on equity and cash, we were just like, this is the cash and you could have it next week. And so that was the deal that they took. Now, I mean,

Kevin May:
the how I got here podcast is very much about the origin stories and the backstories to people’s kind of businesses and their kind of personal history as entrepreneurs. But given the the timeliness of what you’ve just done, which is pivoted in the midst of this crisis, and you’ve scaled back to six people, I mean, it can you give us a sense of how you see the next kind of six months to a year kind of shaping out for you just because, you know, it’s just an interesting part of what you’ve had to do in such a short space of time.

Caitlin Zaino von During:
Yeah, I mean, we’re pretty we’re probably bullish about it. We’re excited about it. I mean, I don’t know if it’s clear through this conversation, but Deepak and I are very resilient co founders that really look to find as much opportunity from down moments as possible and really thrive. In fact, in that environment, for better or worse, we actually thrive in chaos and in crisis. So this is this perfectly suits us. We’re like, very happy to be here in this moment. And we want to grow it and we think that there’s an opportunity to define the future of travel. For what 15 years 10 years travel was on this explosive growth. Hotels would not have looked at this kind of offer in February of 2020. And now we’re filling an innate need for them to bring cash in the door. And there are not a lot of options to do so. We’re quick or scrappy. We’re agile, we’re fast, we’re effective. We’re offering so much against a larger company or even a startup that has more people that’s just a little slower to move. So for us We’re moving as fast as possible. We’re super data driven, we’re really trying to focus on meaningful outcomes for the properties. And we feel like we can redefine the future of travel that the future of travel has to be flexible, that even if people are confident that they see a light at the end of the tunnel, that in fact, this is a very unpredictable virus and an unpredictable environment. And so we have to build for the downside scenario. We want to build a travel company that that also thinks about social consciousness, and the impact travel has had on the pandemic and climate change. So, you know, we talked about how we were already moving, trying to build a product for a next generation of travelers, we actually think this is it and the moment has been brought to us and so we want to use this to redefine how people book travel given ultimate flexibility, smart choices about travel and awakening and awareness of travel impact, and really, basically offline than world’s best hotels at revolutionary prices while building a company that does something for good.

David Litwak:
So it’s interesting you said, you talked about the future travel reminded me of the interview we just did with the founder of inspir Auto. And he actually said that they whether this, you know, the Coronavirus, a lot better than anyone else in the travel industry because they’re membership based. And I like I have another business that I won’t go into. But I’ll tell you a little about the origin story in that we actually once tried to get Bars and Nightclubs to start membership programs. And we definitely had, you know, a moment here where we rolled our eyes and you know, once this, once this virus hit, it was like, you know, these guys were very transaction based, they weren’t loyalty based. We tried to introduce instead, there’s value to you guys and having you know, people come back and back and maybe give them some drink discounts and take a membership fee. And no one was really interested. So we pivoted away from that business and, and I see a lot of kind of similarities, just from its burrata lesson from my own lessons, you know, and my life hospitality it seems like almost like what you’re saying is when you say it should be flexible. It almost seems like you might be alluding to a membership program. Is that the future of what you’re looking at? Because like, right now obviously Coronavirus will pass right like at some point people won’t have as big of a need to, to sell that. So how are you planning on transitioning into the future?

Caitlin Zaino von During:
Yeah, definitely. I think there’s something interesting about a membership model. We definitely think we need to just not to use this word, but really disrupt you know, how we think about booking travel or accessing, you know, accessing these amazing hotels. And I think there is something to be said about membership, there is something we saw a lot of loyal consumers purchase from hotel brands that they knew and that they wanted to survive, because consumers would write messages when they made a booking through hotel credits, the program that we launched, so they would say things like, I love you guys. I’m rooting for you. I can’t wait to come back and they would throw down 2000 bucks in order to support that hotel. And so We definitely think that there’s an opportunity to create loyalty to this network, right? Going back to that network, that network question. So is there a modern slh model or leading hotels with a world model that you can look at here that kind of plays into best in class technology and modern travel priorities and expectations and needs. And even if the environment changes where there is more predictability post pandemic? Don’t consumers want to have greater flexibility, we believe that travel is going to be at least in the near term, near term being two years at least, guest centric. It was hotel centric for a very long time, just like airlines where all these fees are piled on. And now guests are the ones that are like wait, you want me to spend with you, you need to incentivize me to have my loyalty and to spend with you. So we absolutely think that there’s an opportunity to lean into all of those sorts of consumer behavior changes and to build a company that reflects that and Ultimately, during a time of crisis, consumer behavior changes, and it has this time. So let’s know what that changes and build for that. So that that’s a lot where we are thinking about thinking about that consumer thinking about membership, thinking about loyalty. If we can get that consumer or member to behave in a meaningful way, then we’re delivering value to hotels. And if you’re looking at hotels operating at 40 50% occupancy for the next 12 to 24 months, that’s still very well below where they were, what they need. And so they’re going to continue to have to rely on innovative creative models for bringing cash in the door. And if we’re one of those models, driving the equivalent of 10 20% of room nights booked, that’s that’s an addictive thing. And that’s going to be hard for them to walk away from even as the landscape normalizes.

Kevin May:
So, before we just sign off for the end of the episode, I’ve got a question really, that’s just kind of satisfy my own curiosity, right? I mean, what’s the what’s the origin of the name, Porter and sail because, you know, on first glance, maybe people would have thought this is something to do with the maritime part of the industry by virtue of the word sail and it’s but it is not the most obvious. I would perhaps perchance say that it’s, you know, it’s not the most obvious name for either a hotel tech company or a hotel booking company. What’s the What’s the story behind the kailyn?

Caitlin Zaino von During:
It’s funny because actually, sometimes I get like spam from from maritime stuff.

Like rent cheer, ya

know, the point of it, actually, you know, Momoko, my first co founder and I, we thought of the name, we wanted it to flex like, okay, when we first thought of Porter in sale, Google Glass was really big and hotels were literally like, what did you do kokubo class. And so we were really excited. For that technology could was fickle and was going to evolve quickly. So we didn’t want to name that was specific to an app or mobile, we needed to get out of that. And we wanted to build a company that was aspirational that was brand led that was lifestyle LED. So for us, Porter kind of like leaned back into the old school concierge reporter, rather, that would open the door for the hotel, start the experience, and sale for us was exploring and being out in the world and wanderlust. So we felt like it was ambiguously up market, it reflected aspiration. And we could do whatever, we could start selling cookbooks and it was still work but it just it flexed enough for us to be able to change the business, which I’m glad for because we weren’t yes driven where then if we end up changing, you’re stuck with this name. That’s to a really specific model. So that’s that’s sort of where it came from.

Kevin May:
Okay, great. So a very warm Thank you, from David and I to Caitlin zone of on doing thanks so much for joining us today. Lin,

Caitlin Zaino von During:
thanks. Thanks very much for everything.

Kevin May:
Okay, so thank you everybody for tuning in. This is another episode of how I got here. These are mosey on focus wise, weekly podcast where we talk to the entrepreneurs, and those behind innovation in travel and transportation. As always, you can find us if you’re not a subscriber already, on all the usual platforms, Spotify, Amazon, Google podcast, leave us a nice review, give us a rating. We always like to see your feedback. But most importantly, thanks as always, for tuning in. This was how I got here, and we’ll see you next time. Thanks a lot.

Transcribed by https://otter.ai

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