Hybrid Hospitality: How We're Merging the Best of Hotels and Short-term Rentals - Ryan Killeen, The Annex Hotel

Josiah: Ryan, I've been looking forward to talking with you for some time because I feel like, especially over the past year or two, I feel like I've heard more and more conversation just about this notion of, I don't know if you want to call it hybrid hospitality, but taking the best of short-term rentals, Airbnbs, service departments - that whole world - and then the best of hotels, where a lot of people experience hospitality and think of hospitality. You have a unique perspective on this because you worked at Airbnb, you worked at Sonder. You were early in these companies. You got to see how these companies at scale were built that I think are combining elements of this, you know, powered by technology. So maybe to kick us off, I'm curious as you reflect back on your time at Sonder, your time at Airbnb, what were some of your top takeaways from working at those places and how that shaped how you think about hospitality today?

Ryan: Absolutely. I think the element of newness was really exciting at both of those companies, both Airbnb and Sonder. I was much earlier at Sonder than I was at Airbnb, employee number 47, to get really specific. But Sonder would go from flatbook to Sonder, from basement units to full-blown commercial scale properties, properly zoned to compete with hotels. I think for me, it was realizing that the world I came from, which was traditional hospitality by way of Fairmont, was ready to be disrupted, for lack of a better explanation. Hospitality has a lot of consistent themes to it in terms of guest experience, cleanliness, delivering on X, Y, and Z, but there was still room for something else that wasn't available in the market. I feel like both Airbnb being a platform for short-term rental operators. and Sonder were really trying to take a run at providing something else to people or travelers and markets that wasn't readily available. I mean, BnBs have been around since the beginning of time. There's always been kind of back of the napkin or back of the phone book to get really old school places that you could book. But in terms of a commercial offering that was different from big box, I think those were two of the early disruptors there.

Josiah: I'm excited to get into some of the details of how, you know, kind of this does look and how it might look in the world of hospitality broadly. But to give our listeners a bit of context, can you tell us a little bit about your work today, where you're focused and what you're working on?

Ryan: Yeah, absolutely. Where I'm focused today is Annex. I'm all in figuratively and literally. Annex is, you referenced it at the beginning, hybrid hospitality. It really came about as a gap in the marketplace or came from a gap in the marketplace, which was there was big box brands and there was short-term rentals, commonly referred to as Airbnb. Annex blended both of those worlds into a singular product that has familiarity on both sides of the equation. I feel like my background has kind of led here. It's kind of a perfect pickings of things from each experience that I've had and now delivering that at the Annex.

Josiah: I love it. And I think I read somewhere that the Annex is taking the best of boutique hotels, Airbnb and cutting edge technology. I guess as you think across each of those elements, what are the best of each of those areas as you describe it and as you're delivering now at the Annex?

Ryan: Yeah, absolutely. Combining the best of both worlds really put us in an immediate position of connectivity. And what I mean by that is with short-term rentals and Airbnbs, you get these unique spaces that really feel like you're perhaps at your best friend's cool loft in New York or whatever it may be. And that's true. There is very unique experiences on. the Airbnb platform that aren't necessarily available in big box. With big box, sometimes it's a little bit stuffy. It's the same thing over and over again. You miss a little bit of that energy and newness. So with Annex, we've come up with this saying of creatives living comfortably. And what that really means is we have intentionally designed a space that is comfortable for people to come experience. And there's a lot of things that go into that, whether it be the actual brand itself, our culture, our partnerships, the kind of programming we have. But more importantly, it was designing a hospitality experience that, to your point, combined both of those worlds. So to get specific, when you come to the Annex, you're not going to see a front desk. Not because we think front desks are bad inherently, it's because you can facilitate a check-in ahead of time, before someone actually arrives. You're really collecting their credit card ID and a signature essentially saying, Hey, you are who you say you are. We want people to walk into the annex and immediately be met with hospitality. Hey, Josiah, welcome to the annex. Can I grab you a beverage? Would you like coffee or a beer? Like that's a very different arrival experience than having to line up at a front desk for the sake of it. And the comfort goes far beyond that. Being able to head straight to your room, you're able to text us. I mean, those are things that all of us do every day. That's how most of us communicate with each other, whether it's our friends, family, the e-commerce world. It's learning-less. You don't have to learn how to use a hotel phone. There's not a 55-page manual in the room to read. It's text us. It's kind of like texting with your friend, but we're also on-site 24-7 if you want to come have that in-person interaction. So that's a tidbit into what the blend of those worlds looks like.

Josiah: How did you go about designing that experience? I'm always curious how hospitality providers end up providing the experience they do. Was it based on your own personal travel experiences? Did you have a customer archetype that you were creating around? How did you decide to do everything that you're doing today?

Ryan: Yeah, I really think it comes from a gap in the market and less the story of being locked outside with the frozen keys at the Airbnb or a 45-minute lineup when there's two people in line at a hotel. It was re-imagining the way that hospitality could be experienced for travelers seeking something that is not readily that was kind of challenging all parts of hospitality. What do you actually need in the room? Do you need a TV or is an iPad Pro with Netflix sufficient? What do people want to do when they're actually in the room? Should we splurge on having 500 things that people are most likely not going to use or should we splurge on an extremely comfortable bed and a record player to add that home element? Same principles were applied to the, let's call it task-oriented portion of it from a guest experience. How do we change check-in? Why does check-in operate the way that it does today? So it was really just looking at every single aspect of a hotel operation or a traditional hotel operation, taking what travelers were asking for and kind of commercializing that for lack of a better explanation, but really doing that through the lens of brand too, which is really important at Annex.

Josiah: It's interesting to kind of think about that. And I'm curious, what have you seen the impact of this? You've been open a number of years now, I think of both. Anything that comes to mind in terms of kind of like how this has landed with travelers, with your guests?

Ryan: Yeah, it's really nice to see the feedback. Very rarely in hospitality, you get certain types of validation. There's a lot of it. on the customer side of things, whether it's a good review or a bad review, but just the type of feedback that we receive. It was so great. The rooms were clean. I really felt like I was at home. The record players in the room were so cool. I had great coffee from Jason in the morning downstairs. I got some great recommendations on what to do in the city that night. So it's really, it's validating when your guests, your customers through reviews kind of articulate what it is that you've built as a brand. So I'd say that's been a really fun moment. And then there's the lighter-hearted moments that are fun when you see, I mean, you build a brand for a certain demographic, everyone ends up interacting with it for the most part. And you see the elderly parents who have come and successfully checked in on their phone because it's pretty straightforward to do. They enter the room, you see them having coffee the next morning, calling their kids, telling them how proud they are and how cool they feel for doing something like that. So it's a lot of little things.

Josiah: So it feels like there's a lot of people attempting to provide this sort of hospitality now. I've seen sort of a groundswell of, you know, whether you call it hybrid hospitality or something else, there's a lot of people interested in this or are seeking to provide it. I think you have this really interesting perspective because you've been in this category of hospitality for a number of years at some of the leading companies in the space. Then, you know, now you're chief operating officer here at the Annex. So I feel like you have a perspective on this area that few have. And so I'm curious for you, has anything surprised you or stood out to you as you've been building this business and kind of watched people interact with it?

Ryan: It's a great question. I think things that have surprised me is how many brands, big or small, are trying to focus on this hyper-localality. And it's really interesting to see the bigger players in the space take a run at it because it's not as simple as just taking the big version of what you have and putting it in less rooms. There's something about our brand in Annex that is different and that's a very generalist term, but it's the newness of the products, it's the partnerships, it's the programming, it's operating in a city that continuously evolves and changes often and us being able to keep up with that and not only keep up with it, but partner with the people contributing to the fabric and bring that into our space. So to answer your question, what's really surprised me is seeing the big box attempt at it. And then most recently is seeing the amount of short-term rental operators jump into the end quotations boutique hotel space because multifamily is being given the big no-no as a space for hospitality to happen, for commercial bookings to happen. So there's a lot of change happening right now in the space.

Josiah: I'm really interested in what you said there around partnerships and programming, because those are easy to talk about, really hard to do well. And it's a lot of work, but it's a lot of work. But if you do it well, I feel like it does create a really differentiated guest experience. And so I'm curious how you think about finding, forming and producing these partnerships and the programming that you have at the property.

Ryan: Absolutely. Well, I wish I could take all the credit for it. Fully joking. We've got an incredible team around us. There's a lot of brain power that has gone into creating the Annex lens, so much so that we were able to bring on Daniel Caesar, a Grammy award-winning artist, into the mix. And again, it's not a celebrity endorsement. It's someone who connected with our brand and actually likes the experience, that home feeling that we've created, and ensuring that we're able to deliver that throughout multiple facets. When it comes to the actual partnerships themselves, community is a huge thing for us. And community, again, is a broad stroke. And I think the term is thrown around very loosely. It's like, what does that mean? A hotel, yes, there's rooms to it, but there's also common space in which people can kind of come together. And for us, we see ourselves as a bit of an incubator where we're able to form partnerships with various different communities in Toronto and bring them into one space. So when you're coming as a patron, you're almost experiencing something for the first time every time you come. There's your staples in the city and we're always going to drive people to those spots for food and beverage, but we're very excited that part of our brand is actually the newness and the constant change. There's a lot of consistencies when it comes to what you can expect walking through the front door. You know something interesting is going to be happening or relevant, but again, it's trying a lot of new things once, sometimes twice, sometimes three times. I mean, we work with experts. We work with people who are the best at what they do. If we're going to go out and do a coffee shop, like we have, we're not going to try and start that from the ground up because there's someone who's been doing that for five to 10 years. She's way better. So we're going to go to them, we're going to connect them, we're going to try and bring them into the space. Similarly, when it comes to programming, we have great partnerships. We've got a run club that starts from the hotel. We don't create the run club, we partner those two gentlemen in Toronto. Pete and Lucas who are incredible. They started off with a small little run group of three people. There's upwards of 70 people now that start off on Saturday and Sunday mornings at the hotel. We do chess club with a guy named Taylor Harrison, and last week, we had the number two and number four players in the world through a chess.com partnership through that nightcap event. So it's kind of tapping into people who are doing the best version of what it is in the city.

Josiah: Across these different collaborations, I'm curious how the relationship works. Is it something where you kind of pay them to provide these services? Is it more about providing space and access and an audience? Does it vary person to person, program to program, or how does that play out?

Ryan: Yeah, I think it really varies person to person. I mean, on something a little more transactional like coffee, obviously we're going to be purchasing beans and stuff. But again, truthfully from a local roaster, that experience is going to be different than just going to your run of the mill coffee shop. On the programming side of things, I think that the monetary benefit for all parties is kind of the obvious byproduct of doing something really well. You don't start programming with how much money can we make in mind, you start programming with What does the city resonate with right now? What's in what's relevant? And how do we make it that happen in our space on kind of the biggest scale that it can exist or format? So I think we see ourselves as more of a space for, for people to come together and for different types of programming to happen. And then from there, the rest kind of just falls in place.

Josiah: I feel like to do this well on a personal level as hospitality providers, we need to stay connected to our cities or neighborhoods and get a sense of what's going on. I'm curious for you personally, how do you do that? How do you stay dialed into what's going on in Toronto?

Ryan: I couldn't agree with you more. It's everything. Locality is huge. I mean, it helps that our hotel is in a residential neighborhood, so that immediately creates a bit of a homey feeling to it. It's a number of things. So it's ensuring that you're staying connected with the community, again, in various ways, whether that's giving back, whether it's charitable, whether it's philanthropic, whether it's nightlife, it's cultural, it's being on the mark and being genuine about it. It's not trying to force anything. It's ensuring that you're actually nurturing the relationships that you've formed and being a part of the community. A lot of our are kind of recommendations and stuff for us pushing people to things outside of our physical location. We want you to feel at home when you're at the annex and enjoy all the comforts that you would have at home. But at the same time, if you happen to pop down to the the lobby, let's say on a Thursday night and there's programming taking place. Well, whether it's a coffee club or a chess night, we're then going to recommend that you actually go see this out in the wild as we'll refer to it in the various neighborhoods that these kind of programs are born from. So that's how I'd say we stay connected.

Josiah: That's great. So we talked a lot about the guest experience, that side of the hospitality business. Of course, there's all of the back of house operational component, right? You're chief operating officer in this business. You know, I'm curious, you've worked at these technology-empowered companies, some of the biggest, right? Airbnb, Sonder, now you're building Annex. How do you think about the use of technology within this business now?

Ryan: We like to refer to our business as technology-enabled. We're not using tech to replace the guest experience. We're using it to enhance it. We touched on it a little bit earlier, but we're using it to replace a lot of the task oriented work that comes along with traditional hourly staff so that they're able to actually interact with our guests and create an experience. When we think of tech, we think of how do we make our operation more efficient on the backend so that our focus can be on the guests themselves. So tech has come a long way in the last five, six years. We're just starting to see in the last 12 to 24 months serious venture capital be injected into the space. There was a time where it was very bootstrappy and things broke all the time and it's come a long, long way. We have some great technology partners that we work with and it amazes me how quickly their own products are evolving and making us better on the backend.

Josiah: Well, it's great. And I think it does start with the vision of what is the experience you want to provide your guests, but also your team members. And I think, you know, and getting to know you and your work, you've you care about both of those deeply. And that you have kind of this end state that you're building towards. And it seems the technology is the enabler of that. It's not necessarily, oh, we have this new tech feature that's going to change our brand vision. Right. It's like this is an enabler. Is that fair to say?

Ryan: I think that's fair to say. I mean, as you're seeing, tech is going to be the expectation of most travelers in the next several years. You're looking at the biggest companies in the world adopting technology or even like the keyless access, little things like that. It takes them a long time to roll things out that have been in the boutique space for a while now. Brand and technology for us are really, they're being built alongside brand for us kind of takes precedent. We make sure that technology flows into that in a way that works with our experience and kind of how people interact with their business, both on the guest and, and kind of back inside.

Josiah: you actually started your career in hospitality working in housekeeping. And I wonder if we could talk a little bit about housekeeping, because I feel like it's not part of the conversation as much as it should be. It's integral to that guest experience we all enjoy, right? It has to be done every day. But I'm curious how that early experience for you personally, you know, in your career has shaped now you running operations for the company, how you think about housekeeping and that whole kind of like back of house world of making sure that your property is clean and efficient, but also providing good experience for the people that are cleaning that. How are you thinking about housekeeping these days?

Ryan: I think about housekeeping, I think more than most people do, and probably an unhealthy amount at times. I still find myself walking down the hallway and running my fingers over the top of local art and things like that. But no, starting off in housekeeping gives you perspective, right? You're at the ground level, you're delivering a function of the business that is quite often seen as a line item, and you understand the hard work that goes into that. without a clean room and kind of being repeated every single day. It's pretty tough for everything else to make sense. So when I started my housekeeping career, that was my introduction to hospitality. I was working alongside a multitude of different nationalities and women well into their 40s and 50s who were running circles around me and could devour plates twice as high as mine at lunchtime. But it's giving people a purpose and explaining why it is that they're doing what they're doing. We never look at a function of our business, like cleaning is just, Hey, we need to clean the rooms because it's like, well, why are we actually cleaning? We're cleaning the rooms because we want people to experience all of the purposeful things that we've placed in the room, like record players and products and things of that nature. But in order to do that at a bare minimum, that space needs to be clean. And there's varying levels of cleanliness, as you know, traveling around and whatnot. So for us, it's making them feel appreciated. going above and beyond when we have the opportunity to involve them in other conversations that aren't just specific to housekeeping and getting them to buy into that bigger picture, which is culture for us.

Josiah: That's great. I mean, culture drives so much, right? It's culture, it's the people that provide hospitality. That's what makes these businesses possible, right? And so even when you think about a tech-empowered hybrid hospitality offering, people are still the foundation of that. And it's cool that you've thought about that. Backup House, you've thought about it from a guest-facing programming perspective as well. Ryan, where can people go to learn about the Annex and then also to follow you in your work?

Ryan: Absolutely.  @AnnexHotels on Instagram is a great spot to follow us and kind of follow along with all the things we've talked about brand and programming today. Annex.com is our website. Obviously you're able to book rooms there, but kind of check out more about what we have going on on a rotating basis. And then for me personally, LinkedIn is probably the platform that I'm most active on.

Josiah: Amazing. Well, thanks for joining us, Ryan. I learned a lot and love what you're building.

Ryan: Thank you so much.