From 14-Year-Old Housekeeper to Ralph Lauren to CEO: What I've Learned in Hotel Management and Beyond - Sarah Eustis, Main Street Hospitality Group

Josiah: In this episode, Sarah shares her vision for creating hotels that serve as true community anchors, where police officers and corporate executives might share a beer at the same bar. You'll learn how she's built a company that thinks differently about hotel management, balancing creative innovation with operational excellence, and fostering meaningful connections between team members and guests alike. In this conversation, you'll hear us cover everything from the nuts and bolts of hotel ownership structures to the art of building lasting partnerships and Sarah's unique concept of dynamic stability that guides her leadership approach. If you want to jump to specific topics in the conversation, you can use the chapter markers in your podcast player or in the show notes. And just one last quick thing for context. If you're wondering about our changing background noise, we actually recorded this across a few different locations at the recent Independent Lodging Congress. You can find the funny story behind all of that in a quick clip that we posted on the Hospitality Daily LinkedIn page. But without further ado, let's get into it and learn from Sarah about how she's reimagining what hotel management can look like today. This is Hospitality Daily, the show that helps you stay informed and inspired each day by the most interesting people in hospitality. My name is Josiah Mackenzie, and my goal is to help you reconnect with why you work in this industry and get fired up to go out there, delight others, and reach your goals. Let's get started.

Sarah: Main Street Hospitality is our official name, and we are 10 years old this year. We're almost into adolescence, I like to say. So, we still have all of that excitement and energy and sort of curiosity and wonder in the company, which I love. Think of a 10-year-old, but a little bit more grounding and experience and capability and potential. So we're in an interesting phase right now and it's really exciting. So we currently operate eight hotels. We're growing to nine next year, 10 the following. We grow somewhat organically based on a lot of relationships that are strong and long-lasting. We are based in Stockbridge, Massachusetts, which I don't know if people know where that is ... Stockbridge is It's Norman Rockwell ground zero, right? Classic Americana. Classic Americana. It's about halfway between New York and Boston. It's on an important kind of revolutionary road. And at the corner of New York and Boston is a hotel called the Red Lion Inn, which has been there since 1773 and has been in my family for 55 years.

Josiah: Oh my gosh, wow.

Sarah: So that's where Main Street was born, on Main Street, in the sort of warm embrace of this incredible hotel where I grew up. And a lot of our values and sort of the way we think about hospitality comes from that place.

Josiah: Amazing. So I want to get into your personal story, but I want to talk just, I'm always trying to educate people about the different players in the ecosystem of hospitality. You know, your investors are owners in the real estate. You mentioned, you know, owning this property with your family. And then, you know, there's management companies and there's a lot of other players there. But my understanding is that you are engaged in a number of these areas, right, where you just mentioned owning, and then you're managing as well. So it seems that companies such as yours aren't necessarily just kind of in one of these buckets. You could do a number of things, and that's what you are doing.

Sarah: Thank you. I think I was saying to somebody earlier today at the conference, we don't fit perfectly in a box. which maybe is an asset and also a detriment. Because we do own some of our properties, we are investors in some of them, we are third-party partner managers of others, and we have participated in everything from multi-year historic conversions, new builds, we originate deals, we put people together, we have a circle of investors who have supported us and enjoy coming to projects with us if it's the right fit for them. So we are a bit of a bespoke shop, and I guess we sort of like it that way. And you do it all. But at the same time, Josiah, we've grown and we've sort of paid the tuition on different types of properties, on different types of projects, on unique markets that took a lot of study and analysis to figure out. And so we're certainly ready to use that tuition and do more of some of the things that we've cut our teeth on.

Josiah: I like it. I have not heard people talk about their experiences as tuition, but I like that. It's tuition. In our conversation yesterday, we were talking a little bit about kind of growth and doing this with good partners. You alluded to that just now. What makes a good partner? I feel like relationships are a theme that I'm hearing at this conference. It seems a theme in hospitality. Everyone says it. Not everyone does it well. What have you learned about kind of building these good partnerships to grow?

Sarah: That's a great question. I don't think we actually talk about it enough. So I'm glad I'm glad you're hearing it around the conference. And it sounds it could be very like a Hallmark card sounding. So what is that really? And I will say, you know, we have had the privilege of working with a handful of longtime partners, long from 25 years that started with the previous generation of my family, to our amazing partners in Rhode Island, over five, six, seven years, to some relationships that didn't work out that well. Right? No, no hard feelings. But I think the way that we now, again, as we're growing, in the beginning, you're so opportunistic. You're like, hey, I'll do anything. And now that we are knowing, we have a better sense of ourselves, who we work well with. And for us, that is a good structured process, a clear shared understanding of the objectives of the project, transparency around the economics, as much as reasonable. A kind of communication style. I guess our communication style is pretty relentless in a good way, I hope. There is just no over-communication. I mean, it is constant. And I think our partners I don't really call them clients and they really are partners. They appreciate that. They feel in the know. They feel part of the process to the degree that's healthy. Because not all owners want to know everything that's going on in the operation.

Josiah: Does that just come down to the person? I'm trying to think about kind of, how do you think about tailoring communication? Because I imagine that more isn't always more necessarily. I imagine it's a little bit of kind of knowing what the person is looking for.

Sarah: We have good standards of the way we communicate, weekly reporting, and really solid, great financials and all that. And some partners want more, some want less, and we tailor to meet their needs. We work with asset managers, who we love, because they also help educate owners.

Josiah: That's a fresh take. I haven't heard that on this show. I love asset managers. They're my best friend. So I heard they educate owners.

Sarah: They educate owners. They help us be better at our jobs. I really believe that. when they're good asset managers.

Josiah: How are they? Are they sort of pushing on ideas?

Sarah: Let me think about it because we've worked with great people from Pinnacle and the group we're working with now, they're amazing, Fulcrum. What they do is they help to rationalize, to help the owner understand what is rational in the marketplace, in the underwriting of the project, in the expectation of the operator. And they create, and then, in turn, they hold us accountable in a way that is fluent in our language in order to get the best out of us so we're delivering for the betterment of the property and the value of the owner, who they represent, of course. But, what we've done over time is build really good relationships with our asset managers. I just find them to be great partners. I enjoy a project where there's a great asset manager on there.

Josiah: That's great. In the spirit of education, I'm actually writing a guide around how owners and investors should think about selecting a management company to work with. I wonder if we can speak a little bit about this, because I'm curious, I mean, you're an owner-investor yourself, so I think that's, we might touch on that. That's an interesting, we have to skip in the game. But I guess, you know, just thinking about it from a pure play investor who's looking for someone to manage their asset, what questions would you advise them asking, knowing that you're an owner-investor yourself? What should they be asking or looking for?

Sarah: Ah, well, there's such a range and it does depend on the project. If it's a small, bespoke, super personal, sort of patriotic project that you're doing because you're passionate about it, that's one avenue. If it is a bigger, more structured, multi-partner, cap-stack kind of project, that's a different one. Regardless, I would encourage first-time hotel developers, owners to absolutely consult with an asset manager. I keep the asset manager on forever or not. Number one, I highly recommend. Number two, I really think a deep development of your own business plan and your own expectations and your own goals for this project, financial, psychological, emotional, What impact are you trying to make? I'm serious. Is this a… Psychological and emotional.

Josiah: Psychological and emotional.

Sarah: I go to all the investment companies and nobody's talked about this. Well, that's a problem. Okay.

Josiah: Why is this important?

Sarah: Oh, my God. It's so important. So I think for people who want to do hotels, because they're kind of sexy and fun, especially independent ones. And they can be a great way to contribute to a community where you grew up. They can be a great way to honor your family heritage. They can be a great way to revive or re-upcycle an important building. And those are all really admirable reasons to do a boutique hotel. And they can also be a decent way to make money, right? So I think for an owner who is venturing in or is growing their hospitality portfolio development is to be, before you seek and go out into the market to look for a management company, to be very clear about what your own objectives are. And when I talk about emotion and psychological, I think we should recognize that it's in there. Do I want my community to feel proud of me? Do I have economic expectations that are X, Ys? Do I want to sit at the bar and just entertain in my place? Is this a legacy play for me?

Josiah: This happens, and I'm glad you're bringing this up, though, because it feels like the motivations of owners or investors are as diverse as there are people. I feel like I've been kind of playing with this notion are like the best hotels just art projects or they're interested in your businesses too because I've met a lot of folks where it feels more of a legacy player it's like or I want to walk into this cool lobby and be saying I own the place which is maybe fine. Still, I've also ran into folks where they're making money, too, even though it's very cool and meaningful. Has that been your experience?

Sarah: Well, absolutely. And they should, right? My point is, and with the right management partner, you can do that. But the core message, I guess, I don't know, that I'm trying to articulate is that if those objectives are misaligned, even from the beginning, then oftentimes it can be detrimental to the project.

Josiah: I wonder if we can talk a little bit about your personal story because before this we were talking about how your family has owned this historic inn that's been around since the 1700s. You've owned it and your family's owned it for 50 plus years. So you at a young age you were kind of like growing up it sounds like in this environment of hospitality. What were some of your earliest memories of being in that environment?

Sarah: Oh gosh, well we, you know, it was, this was our modern family and so my father had married into this great family and it was always a big adventure. We would, I grew up outside of Philadelphia, we would come up to the Berkshires in the summer and vacations and even just as a child going to the Red Lion, it was like a, it was like a palace, right? You got dressed up, you were in your best behavior, there was kind of a sense of decorum that was really wonderful and we try to maintain to this day. And so as a very young child we were just there for special occasions and family dinners and whatnot. And then I started working there as a housekeeper when I was 14. You started working at 14? Oh yeah, as my children have done too.

Josiah: Did you volunteer? Were you on toll for this opportunity?

Sarah: No, no. It was just sort of what we did. Nobody was forcing anyone. But it was fun. You earned money. You learned how to work. You learned how to show up on time. And housekeeping is one of the noblest jobs in the hotel. And so I'm really glad that I have done it. And I make mean hospital corners, because we use very beautiful flat sheets.

Josiah: Incredible. But from a very young age, you're doing this. So did you view it back then, 14, 15, 16 years old? Was this just a job, or did you see long-term career potential for you at that age?

Sarah: I, you know, it was a, it was a job. Yeah. And it was sort of part of the culture of our family and it was fun and my friends were doing it. And I wasn't, I wasn't dreaming of a career in hospitality at that particular time. I was dreaming of a career in fashion.

Josiah: In fashion. Okay. Did you end up studying that? How'd that go?

Sarah: So I went, I come from a very interesting, amazing, crazy family, lots of creative people, business people, but I went to college and I studied fine art and art history. But I knew that I wanted to go into the fashion business, but I didn't go to design school specifically. I just, I don't know, I decided to get a liberal arts education. and just sort of self-trained and internships and stuff in New York, and as soon as I could get myself to New York City, I did. What was it about New York? Well, it was just where everything was happening, so. Yeah. And so after college, started working in New York and got myself a job at Ralph Lauren. At Ralph Lauren. Yeah, and that was, that started a 25-year Series of chapters and there was Ralph Lauren we we moved to California and I worked for the for Gap Inc Which is right across the bay from where we are right now, which is an unbelievable experience back to New York for 10 years at limited brands another stint at Ralph and then Paris for three years, but what was interesting about those chapters Josiah that you know, I reflect on they were all family businesses and They were huge corporations, but they were all family businesses. And the founder would show up every day and talk about why the company existed and what was important and what the values were. Some of their children were involved in the businesses and their relatives. And so I didn't realize it at the time, but that was actually really meaningful to me. So when we were considering coming back into our business, I don't know, it all started to make sense.

Josiah: I'm really interested in family business dynamics and founder-led companies. How would you describe what that looked like? I don't know if there's an individual that stands out during that time in fashion, but was there an individual that made a mark on you, and if so, how?

Sarah: One of my great mentors and someone who I really credit with so many days of my career was a gentleman named Andrew Mag. He wasn't involved in the family part of the business, but he was my boss at Benin Republic when I was a young sort of I was coming up, I was scrappy, working for Mickey Drexler, kind of in this really exciting environment at the time. And he saw something, I think, that he wanted to cultivate in me, and he did that in a great way, and then invited me to move back to New York to work at Limited Brands with him. And we were creating brands inside. We were in a sort of brand think tank inside a huge company that was quite structured and quite procedural, right? And so he just gave me this incredible opportunity. And then I kind of, you know, and then I took it on the road. So there've been a few people like that, but he was, he was, he was probably the most pivotal. And then he went on to run Burberry and do really interesting things. Wow. Yeah.

Josiah: It sounds like a really interesting opportunity. And I'm thinking a lot about brand these days. I feel like, you know, we're at this event where there's all these sessions talking about essentially how do we get a sense of what's going on? How do you identify needs? How do you, you know, address them? What did you learn in the world of fashion when you were creating these brands that you've brought into the world of hospitality?

Sarah: Well, it's good. I think about that sometimes. It's so natural to me, but I try to articulate it. For example, just before I arrived at Limited Brands, it was a company that was based on massive runs of production of one item in 50 colors in China that were well-crafted but affordable, and they put it in a store and sold it. That was pretty much it in the 80s. as I got there and as we were creating, we realized the consumer needed a story. It wasn't just a store full of stuff that was going to continue to inspire them. So they needed a story. So whatever, creating a capsule of a little collection that made sense, that was coordinated by color, that had a point of view, that had balance to it. Do you know what I mean? And that was like a radical concept at the time. And so when you think about hotels, and when I came back into my family's business and thought, okay, am I qualified to do this? I'd never run a hotel company. I had no idea what I was doing. But this experience in these extraordinary, where Ralph Lauren at the other end of the spectrum, was such a strong brand, that if we didn't understand it, or we kind of felt like we needed some kind of focus group or brand book, Ralph himself would look at us and say, then you just really don't get it. And you shouldn't be here. Okay. So I was, I was working at both of these, in both ends of the spectrum. Cause he, he showed up every day to make sure that everybody kind of understood through osmosis. Like if you're paying attention, you understand what this brand is about.

Josiah: So I brought… Sorry to jump in there, but I just, I have to, I'm just dying to, was there an interact, are you able to share a story of kind of an interaction with them? Cause I've known some of these characters outside of the world of fashion, but that they just are the brand and they kind of just get really frustrated when people don't say

Sarah: Yeah, when people are trying to operationalize the brand, they're like, why are you doing it? Well, there is a funny story that I do recall. I worked in the womenswear part of the business, and then I went away, spent 10 years at Limited Brands, and then came back to Ralph Lauren in the menswear division. And we were building a new collection. We were working on a kind of strategic plan around how to grow the business. It's a public company and, you know, it's a big deal. And we had gone out and done a full competitive shop of like all Tommy Hilfiger shirts and all Brooks Brothers shirts and all, you know, we're talking about stripes and I mean, yeah. So we did this whole shop and we were so proud of the work that we had done. We just like put it all together strategically. Here's the pricing structure. Here's who's got these stripes. Here's who's got these checks. We should be in this, you know, if we're going to differentiate, we should be over here. We did this whole presentation and Ralph was like, I don't understand why you did all this. He said, I don't care what Tommy Hilfiger is doing. I don't care what Brooks Brothers is doing. I know what we do, and what we do is us, and you follow me. We are going here, and I really don't care about the rest of this stuff. My whole team was like, okay, you got to be kidding me. But I misjudged it, right? Now, we should run the business strategically and thoughtfully. in partnership with Ralph. He knows where we're going. We need to make sure it makes sense in Macy's, right? But it was really funny because he just he's like, why? So I think there are and there are hoteliers like that who I love and admire. who are not looking to crowdsource their next concept, and they're not looking, you know, the brand book, even though I really cherish a good brand book, because it helps keep everybody aligned, and it helps sort of cascade the story in a way that is communicable and operationalizable.

Josiah: That sounds very sophisticated. Please, yeah. That's like a Harvard Business School term. But I'm curious how you think about this now, because you're running a company. You have such an interesting collection of properties. And it feels like a lot of lifestyle hospitality has been very ego-driven and founder-driven, or whatever you want to call it. It can be. It can be. But you observe this, and now you're in the position of running a company. How do you think about that, all those experiences now, running the company that you are?

Sarah: Yeah, I think all of your last question, all of that served me, even though I might not have known it at the time. I try to reflect on my role in the company, frankly, and I have so many talented people who work with me. When I came back to this business and tried to think about how we were going to grow it thoughtfully, rationally, intentionally. I knew I needed a lot of people who were much smarter and more experienced in this particular industry and just had parts of their brain that are different than mine. So I've been spending 10 years really cultivating that team, and I feel very blessed to have the people I do. And I think about myself as, at this point, I check in with them at the beginning of each week to make sure they tell me what they think I should be doing this week. I'm in charge of brand, overall brand integrity. I'm in charge of ultimately client relationships and partner relationships. Like if something's going south, I get on the phone with the partner, right? I'm in charge of our five-year plan and our growth strategy and being here at the conferences and being out in front and cultivating new projects with the right people. So I've got like three things that I really need to do. And, you know, I harness a lot of what I learned working with both a very volume process, kind of, how can I put this, sort of very systemized business like Limited Brands, to one that was very creative and a lot of movement and dynamic kind of thinking, like Ralph Lauren. And what I'm trying to do with Main Street, and there are moments when you hit it, and then there are other moments where you're, you know, not all the way there, is create this culture of what I'm calling dynamic stability. Dynamic stability. Yeah. Tell me more about that. So dynamic stability is a very cool concept. My team, like, rolls their eyes because they're so sick of hearing me talk about it. But I do anyway. And it came from a book called The Creative Priority that I recommend to everyone. And it was written by a guy named Jerry Hirshberg, who was the head designer for Nissan for many, many years and created this unbelievable, like Google before Google kind of creative workspace in La Jolla, California, inside and in the service of a very conservative Japanese company. So he wrote a book about this whole experience and these tenants and sort of foundational concepts that he developed and used. And I still use them a lot. And one of them is called Dynamic Stability. And what it represents, if you think about it visually, it's kind of a rectangle with a wavy line on top of it. And in the rectangle, in the box, if you will, are the things that are foundational to you as a person, your family, your company, whatever you want to apply this concept to. And they are repeatable actions. They are things that people can count on. There are things that, you know, your values, your systems, your SOPs, not that they'll never change, but if they are going to change, it's a big deal because they're in the box, right? This kind of operational structured box. The wavy line on top is the creativity and the dynamic nature of what we're doing and movement and change, which is inevitable. and how we respond to all of that, and we don't get too stuck in the box, which can happen. And there may be companies, hospitality, retail, who are looking for the computer to tell them what to buy next year, or so programmatic that they can't get out of their own way, right? And other companies, and I've worked in both. that have no process and no foundational kind of operating system. And so they're constantly on the wavy line, and that's not sustainable either.

Josiah: How did you operationalize that? Because I like a good framework. And then I'm curious how then you took this from a theory or a construct into the business.

Sarah: Well, I think it'd be better to interview one of my team to see if it actually works.

Josiah: I might take you up on that. I love talking to people, but anyway.

Sarah: See if I'm actually talking any sense. But we talk about it all the time. And so, for example, in this last phase of Main Street, let's say since COVID, we've had a lot of growth, but maybe not enough systemization of how we're doing what we're doing so that we can effectively take it to the next project. So last year, we sat down and we said, we've got to build the box. And here are the kinds of things that have to go into the box. So inside the company, if you say the box, people know what you're talking about. And we've now done that and it takes so much discipline. You'd be amazed.

Josiah: Can you share some of the things in the box? What are we talking about?

Sarah: Oh my God. I mean, the things in the box are obviously all of our employment processes and how we manage people from a legal and administrative standpoint and what is non-negotiable and what are the SOPs that the properties have to abide by and sort of, as well as in the box, something like what we call the Main Street 10. The Main Street 10, which is essentially our people charter, which we built. And we crowdsourced that with the organization and said, how do you want to feel at work? How do we want our people to feel at work? And what are the 10 kind of commandments and commitments that we're going to make to create those conditions for people? and we did it together and we published it and it's called the Main Street 10. And so that's in the box, right? We're not changing that because somebody feels like it, right? So in the box are all of our systems that really drive the company that we are dedicated to, that we are refining. In the box are the kinds of meetings and structures and reporting that we do. It doesn't mean that we wouldn't refine that and tweak it, Josiah. But once it's in the box, it's kind of like it's in the operating system.

Josiah: We don't need to keep revisiting.

Sarah: Yeah, and if we do a 3.0 upgrade, that's fine, but we'll reissue the operating system. Does that make sense?

Josiah: It makes a lot of sense. And then, so interesting, so that's in the box, and then can you tell me a little bit more about kind of what's on top there? The wavy lines. The wavy lines. The squiggly lines.

Sarah: Yeah. Well, it's great, and a new project is very squiggly, right? We're getting to know the new partner. We are figuring out the market, if it's not one that we've worked in before. In the box, we have a critical path process that helps us stay grounded, like step one, step two, step three. How do we ramp up a new property, take it over, make sure it's operationalized? That's in the box, but just the Bringing on a new property, you're gonna think I'm crazy, but it's like inviting a new child into your family, right? There's so many different elements. And that child is like, it might be like a blended family, right? That child has different DNA. It's like, how do I get this child into our culture and get it harmonized with our culture, right? And that is squiggly for a while, and then it gets more established and it sort of gets in the mugs. But I also love starting, you know, in the meetings on Tuesday we have a great executive session every week and we have an agenda, we have a rhythm, but every once in a while we're like, you know what, we need to spend some time up here on some topics that are a little looser and maybe less defined and squishy and complicated and so.

Josiah: I like it. I appreciated chatting with you yesterday because you were talking about some of the things that were going through your head as we were at this conference. One of the things that you said you want to make sure we touch on in the conversation is how you think about responsible growth. I wonder if it's probably connected to what you've just described, but it's interesting to me because I'm a marketer by training. I feel like I just growth, growth, growth. More is always better sometimes at these conferences. I want to talk about scale and growth. But you said something to the effect of responsible growth. I can't remember the exact phrasing. I wonder if you could share a little bit more about how you think about that. What is responsible growth? How do you think about growth, I guess, in general?

Sarah: That's good. Thank you for asking because we think about it all the time. I think we are now, and I'll be very honest about the fact that we've had growth in Chapter 1 of Main Street from 2014 to 2020. We've had some attrition too from projects that either term was finished or the property sold or whatever. The growth in our 1.0 was opportunistic. Not in a negative way, but we're like, hey, we'll try that. Why not? Learning about what the ROI is on our time, how we need to build our services model to support different types of property. And it was a lot of trial and error. The growth in 2.0, which I would say kind of post-COVID to now, has been with trusted partners, has been on projects that are so accretive to our portfolio and are totally on mission. And they've been, it's been sort of one each year, right? We're ready to do more than that because now we've got it, the box is stronger. And so we've got capacity, we're ready. So the last year, we have been in some very interesting conversations with amazing people about potentially partnering, about potentially joint, kind of M&A style discussions that were exciting because we're thinking, wait, maybe we can grow faster. to scale. And for us, scale is not 100 hotels, Josiah, but somewhere between 10 and 100, right?

Josiah: Okay, but it's more. People keep telling me this word scale. Why is scale interesting to you? Like, what are the upsides or interesting?

Sarah: The reason that scale is important, because even though we're 10 years old, we're profitable, but we are I want to make sure that I have a really good foundation and that we're building value in the organization and providing career pathways for people. And we're still, again, I still feel like we're kind of in that pre-adolescent phase. And I see us getting to young adulthood is kind of what I think scale would be, right? So we're not too big and stuck in where our effectiveness is diluted or that our brand or kind of, you know, personally, I love to go to all of our hotels. And I am mindful of being able to do that and have a personal connection to each one. And so scale for us, you know, might look like 20 or 30. I don't even want to put that number out there because it's arbitrary to some degree. That makes a lot of sense. But I think, and you asked me about scale.

Josiah: I lost my train of thought a little bit. I'm just kind of like curious, you know, why does that matter? I wonder if, you know, kind of, I feel like people keep telling me about like the people and the culture kind of within Main Street Hospitality is really different. And, you know, you've seen a lot of different businesses, a lot of different hospitality business. I'm curious if there's an element of the culture, kind of how you think about people that you think is different from what others in the industry do. And I'd love to do like a little deep dive into that. Does anything come to mind in that regard? I do.

Sarah: I have my little card that everybody carries around that has our mission and values on it, which helps keep me honest. I don't know. I mean, I don't know if we're doing anything. I feel pretentious in saying, well, you know, we're doing it better than anybody else. I really don't think that's true. I think what we're doing is doubling down on what we believe in and other, you know, and whether everybody believes in it, it's okay. That's our thing. Which is, you know, this idea that, and I have this amazing head of people and culture who joined us a little over a year ago who has helped me bring this to life. But we started with a purpose statement, Josiah, which was creating places that enable people to connect in meaningful ways. And that was over 10 years ago. And it wasn't like be the best hospitality company ever or grow brands. It was just this idea of creating the conditions through design, through obviously thoughtful and intentional hospitality, through kindness, through charitable assumptions, through that we could create the conditions for our people as well as for our guests where really meaningful connections could happen. And what I see is that that happens in our team. And listen, we've had amazing people who've been with us in chapter one, but maybe not chapter two. We have amazing people in chapter two who may or may not be with us in chapter three, right? So we've certainly had turnover. I don't mean to suggest that we haven't. And we've invited some people into the company that maybe weren't a good fit over time, and it was better for them to be somewhere else. So I really… We are not magical in the way that we're doing anything, but I appreciate when people reflect back to me this vibe that either working at Main Street or working with Main Street is a really satisfying experience for those reasons. We put a lot of trust in our people. We invest enormously in relationships. We are kind of relentlessly transparent. Do you know what I mean? If someone in the organization is having a problem, if they are struggling with whatever it is, we apply a lot of resources to making sure that they not only can be accountable for their feelings and get it out and get it dealt with, but that they feel there's a real support network for them within the scope of work and outside of work. So there may be some of those things that people appreciate.

Josiah: I like that a lot, and I love that North Star guiding mission, because for me, this is what is most compelling about hospitality is that environment where people can connect. I feel that is going to become only more valuable with time. And I think from what you described, it seems this opportunity for, you know, staff to connect with each other, guests to connect with each other, staff and guests to connect. As you kind of think about all these interactions, you touched on design, all these different elements, are there some Aspects that you are kind of most excited about or proud of that you've it could be designers can be something else that I guess you've done something within the business to foster those connections and

Sarah: Well, I think, you know, I'm so proud of each of our properties. We invest a lot of heart and soul and blood and sweat and all of that, and so many of our colleagues do. I think one of the most interesting and I think satisfying, I'll highlight two projects, and they're very different, and they're on the ends of the spectrum from a luxury and economy standpoint. And those two are Canoe Place Inn, which we opened in the Hamptons two years ago, and Hotel Downstreet, which is in North Adams, Massachusetts, that we converted and formally opened a year ago, even though it stayed open during the renovation. So Canoe Place is, both of them are transformative projects. Both of them are placemaking kind of high community impact projects. Both of them have this responsibility to be sort of the heartbeat of their communities, right?

Josiah: So when you describe that, the kind of the opportunity you saw with both of them is this is going to be more than just a business that the value to folks that interact with it will be within the four walls. There's some part of the fabric of a broader environment. And why is that important?

Sarah: Well, I believe it's important because as we, as even Eric Jafari and I were talking about yesterday, that this whole idea of self-actualization, that may or may not be an overt and super conscious objective of a person when they're coming to a hotel, right? Oh, I'm going to go to a canoe place and actualize myself. It's not that. But the fact that they can come and have a really tactile high character high quality experience where they they have They care for themselves. They have a great sleep. They have great food and PS There's incredible programming going on at the hotel that feeds their soul and feeds their brain I like that we're doing both of that. And Scott Williams, our CMO, has helped me enormously in developing those programs.

Josiah: So for me, this is more interesting because I feel like everyone talks about experience in a hospitality, and I find it's too broad of a concept. But I think what I'm hearing from you is almost this kind of transformative element, and it could be on a micro level. But essentially, you're going to the hotel to do something, even if that is a weekend getaway. But you kind of have this thing that you're hoping to achieve. And it's almost like how you make self-actualization practical. It's like you're going to be different after you've left it. But experience feels too vague to me. I don't know if you feel that way.

Sarah: It's starting to get overused. I do agree. And so what is it? Well, you know, our focus is on the idea that Either you come explicitly for a musical performance, or a political talk, or an interesting film that is going on, or you happen to be staying there and, oh my god, look what's happening downstairs in this great room. And it creates a feeling of exploration within the hotel. a kind of I think a deeper adoption of the place so you might have come for something but then you bring your family back again for something different and we have found that even beyond like having a great spa or having a sound bath place or having a cocktail mixing thing which is great I don't know, this dimension of sort of learning, participating, and we really program in different, you know, looking at art, being part of an art opening. I don't know, this cultural programming is something that we believe strongly in, and that is a big part of all of our hotels. And I love seeing it at the different ends of the spectrum, right? With a very high-end consumer. And even what I love about these two hotels, when you asked me, you know, Why are they both important? Seeing how people engage with, you know, people in Hampton Bay is walking into a canoe place and say, oh, I have so many memories of this place from the 80s. Oh, my God. You know, that is when we get really happy. That's going to feel so good. And then in North Adams, you know, people seeing their city, which has been pretty, you know, it's been had a 25 year comeback from sleeping for a long time. Right. Those kinds of cities coming into the hotel and being like, this is awesome and being grateful that there's positive momentum in their place. And I just gotta say, I think that's what brings me the most satisfaction in what we do.

Josiah: Well, I think you may have answered my question, I think, because I always, I want to do this little PSA of why shouldn't you work in hospitality? You built this great career in fashion. It feels like there's this canvas that you can do so much with. Is that, am I putting words in your mouth or is that sort of like, yeah.

Sarah: And I get super excited and my team has to sometimes help me like calm down because we do need to do the right projects that are right for our scale of business at the moment. But what I love about all of our properties, and if you poke around and look at them, They all do that, and I want to do more in each of those kind of, you know, that sort of affordable, but really cool. Not that it's, I mean, we'd be open to doing soft brands. It's not about not being a brand in kind of an aggressive way, but I don't think you have as much flexibility to do what you want to do if you're branded. So I love that. And then these beautiful destination boutique hotels that are so inextricably linked with their place. that I just think they're just fun to work on. And then this idea of luxury property, but that is actually really accessible. So what I love about Canoe Place when I go in there, what makes me happy is, you know, the policemen having a beer and enjoying a burger and sitting right next to some really swanky person from New York. And I love that. And that is when I think people learn from each other and our places actually become, without being overly prescriptive or preachy or whatever, they become places where, A, intergenerational life can happen where younger people are learning from older people and in between. and people with different points of view can sit at a beer, and then maybe they can talk about their differences in a more civilized fashion. This is great.

Josiah: You're a pro, because I feel like… I'm trying to be relevant. You're reading my mind. We're in a political cycle, and I'm asking all my guests to talk about, is there something about hospitality that can bring us together? And I feel like you read my mind, because it seems like this is what you're seeing. Because people have strong political beliefs, but I feel like when they get together in a hotel or restaurant, I feel those sort of fade into the background and it's more human to human.

Sarah: I don't know if you're seeing this, but I mean, listen, I you know, we are we are our the doors of our hotels, for the most part, are never locked. Like when you think about that, like it's not residential, it's not commercial real estate, it is hospitality and usually the front door is never locked. The red line in the door has never been locked in 250 years. So the point is like anybody can walk in. Now that might make people feel vulnerable, I don't know in this day and age, but anybody can walk in and we welcome it. And as long as you're operating within the culture and the sort of decorum of our place, You bring your whole self into the property, and you bring your beliefs into the property, and you bring your, you know, and I've seen some great discourse happen at the bar is a great place for it. Because everyone's a little, I mean it can get a little dicey, but like basically people are relaxed. They're there in a context of enjoying themselves for the most part. And so it's not a bad place for the lobby at the Red Line Inn. I mean, it has been a hub for gathering and communication and hopefully human understanding for, you know, 250 years. Porches are great for that, too. Sitting on a porch and sitting in a rocking chair is a good place.

Josiah: It's great. So, thank you so much for taking the time. Thank you for your flexibility, everybody. Sarah is an absolute legend. I'm a homeless podcaster. So, we'll start a GoFundMe for that. The itinerant podcaster.