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A Conversation With Jersey Banks, Co-Founder, Urban Cowboy · The Failure Gap

• Julie Williamson, Ph.D. (00:00.078) Hello and welcome to the Failure Gap, where we talk with leaders about closing the space between agreement and alignment. We love talking with interesting people and today we're joined by Jersey Banks. Jersey is the co-founder of Urban Cowboy Boutique Hotels and the Dive Motel. From surviving the pandemic to expanding and growing, Jersey has made a mark in the boutique hotel world, working with her partner to build a unique brand of Western Shake Week's luxury. With Urban Cowboy established in locations across the United States, Jersey is continuing to expand her own horizons in new and creative ways. Jersey, welcome to the Failure Gap. Thank you. Thank you for having me. Yeah, we're so glad to be able to talk with you today. You've done such interesting things in your life and I'm looking forward to hearing more about them. But before we get there, how about if you just give our listeners a little bit about yourself and your journey to leadership and where you are today? Absolutely. It was an interesting journey. I was a professional dancer. That's how I started my career in life from the age of three to my mid-twenties. And I moved to New York. That path took me to New York City to obviously pursue dance, my dance career. And I graduated from New School University with a degree in dance in 2008, which was like the height of the market crash. And there was no... There were no jobs for dancers or really anyone, right? And so I did what I called the New York hustle. I got into nightlife. I got into modeling. I got into like everything under the sun that you do just to make rent and dance quickly became something that fell by the wayside just because you couldn't, I couldn't survive doing it. And it's so rigorous and so intense. And eventually I talked to a friend and he was like, you know, He was a finance guy and he was like, you have no skills. Right. He's like, he's like, so you know what you can do with that real estate. So I was like, of course, look at my real estate license. And that's how I met my partner. And he was my managing director at the time. I did a few years of real estate, hated it, got out of it. And as I was getting out of it, we. Julie Williamson, Ph.D. (02:27.374) deepened our relationship, started dating. And he had just purchased a townhouse in Williamsburg, Brooklyn and was designing it to be like kind of his dream home. And he was like, you should run it. you Airbnb'd your apartment. Like you'd be perfect. Like we can have my friends stay there and like you can run this thing. And I was like, no, like I don't even think that's legal. Like that's like. That's not what I want to do. no. And he has the gift of gab, definitely. So he convinced me somehow he turned my no into a yes within a few months. And when I was like living in this townhouse in the basement, like cleaning rooms every day and hosting parties and people were coming to stay and eventually it just kind of turned into something that was bigger than what we had ever set out for it to be. We didn't have a name at the time. It was just a cute five bedroom bed and breakfast with a nice design. And this is, know, 2014. So this is kind of the height of Instagram, social media coming into play. Instagram was still instant. Influencers were just starting to happen. A lot of them were like photographers and models, because it was like content. you know, it was like who could make a beautiful picture? Those were your, your influencers. And we happened to have a space that was beautiful and very photogenic. And so they, you know, we had one photographer come stay with us and then that spawned a long lineage of photographers and creatives who ended up coming to stay with us. But, you know, at the beginning, we, didn't even have a way to take people's payments. Like I, you know, we had like someone's parents come stay and they were like, how do we pay you? And I was like, cash, I guess. You know, like, was like, what's a credit card machine? How do I get one? Like, yeah. There was no like square payments yet. Like none of that existed yet. And so, yeah, we started very, very humbly kind of, you know, we were disruptors at the time. Julie Williamson, Ph.D. (04:53.582) Airbnb was big, the hotel lobbies in New York were already trying to crack down on that. So we were right in that mix of disrupting the hospitality space. And then we had also a very unique hospitality style. And so that kind of spawned this interest in us. And New York Magazine came to stay and they were like, you need a name. Yeah, that would a good place to start to build a brand. Yeah, they were like, we can't write an article on you if you don't have a name. And we were like, for sure. And so many whiskies and late nights and thesaurus.com later, we found Urban Cowboy. And kind of as a joke, and like, between you and me, we hadn't seen the movie. So it wasn't really named after that. But we just thought we had this kind of Western Americana cowboy freedom pioneering spirit about us. And that's where the cowboy came in, but we were in the middle of Brooklyn, so we're urban. just, it made kind of sense. And yeah, now we are, we quickly expanded to Nashville. After that, just by listening to people who came to stay with us saying we should go there, Nashville became our first boutique property that wasn't, it was more of a hotel and less of a bed and breakfast. And then we did a lodge in the Catskills after that, which reopened a week before shutdown for the pandemic, before COVID, which was also a lovely time to be alive. And yeah, and then we just recently opened in Denver about a year ago. Yeah, well, congratulations on that. Trudging forward, yeah. Yeah, but definitely accidental hoteliers, know, not anything we planned to be just kind of kind of happened to us because people liked what we were doing. You know, we had space, we invited people into it and it worked. Yeah. Well, I also feel like you should go back to your friend in finance and say, you know, actually, I did have marketable skills because you knew how to design and you were creative. And I'm sure that your dance and modeling background. Julie Williamson, Ph.D. (07:12.714) enabled you to take advantage of the photographers who were there and to create a space that felt really different for people. Yeah, you know, we, I think, especially coming from a nightlife background as well, like, it's very exclusive industry. And you have to pay to play and like, it just wasn't that interesting, though, like none of the conversations you have in the club at 2am are that exciting. quite honestly. And so, know, the having space where you could have conversation with another creative or just another person who lived nearby. We had a lot of just our friends there all the time that really made the space and they made the conversation. They made it interesting. And that's like your first foyer into understanding that people are part of what fills a space, you know. Place in space, Yeah, place in space. You know, it's interesting you talk about it as an accident, but it's also the result of a willingness, right? And an openness on your part and your partner's part to say yes and to explore some things and to put some things at risk. I'm sure there was some risk taking involved here. Can you reflect at all on some of those moments where you felt like you did, you had to move from this is happening to this is intentional and we're gonna really try and make a go of this. What does that moment look like? So the moment we went to Nashville, expansion is kind of the thing. We got out of the bubble. We got out of the bubble and initially it made sense on paper because you're looking, you're saying, have five rooms, we make this amount of revenue. And if we did another one with more rooms, we'd make double that. But then you have to understand that understanding a key aspect of our business was us. And like the struggle to kind of duplicate yourself and or communicate a thing that is inherent in you. I built myself into that role. Julie Williamson, Ph.D. (09:37.45) over my entire existence of life. It's not anything anyone taught me. And as an entrepreneur who's starting this kind of idea with just one other person who shared that idea, you don't realize how hard it is to communicate that message, even though we had great marketing and like we had a good story and we knew how to tell our story, getting someone else to make it theirs. in a leadership role at a place far away that we wanted to feel like, you we wanted them to feel like they owned it the same way we felt like we owned it. And that's just not how that works, right? So, you know, we were green. were very, we were young and like didn't, you know, I was still in my twenties when we did this. So it's complex and complicated. And we had to roll through a few personalities and understanding of people. in these roles to like figure out what expansion really meant and how to like cement that for ourselves. As we were building a brand that also was taking on a new personality of being something intentional, right? Not just something that was happening in Brooklyn and it's now in Nashville and we're like opening a full service restaurant and bar and. you know, actually, and we have investors now and we have we have people to answer to and there's like all of these things on the line. We have mortgages and loans come in construction loans and like, you know, we're we we made a beautiful product and now we had to operate it and like understanding the operation and maintenance of that is with people in place that have to do it for you was a whole new experience, right? Because we couldn't just look at each other and be like, let's get it done. The basement's flooding. Get the buckets like you don't you know, like you don't. You don't have that. I think also that's where people can sit around and dream all they want. This is a great idea. We should totally do this. But what you're describing is the hard work that comes with it. If you really want to make that dream a reality, you got to roll up your sleeves and get to work. And I do think it's a little bit an outtake of the influencer age that things look easier than maybe they are. Right. It looks like, you got lucky or it was so Julie Williamson, Ph.D. (11:54.432) easy to do because it looks beautiful on Instagram. But the reality is behind all of that is a whole lot of work. It's a whole lot of work. Yeah. And I think it's very aspirational work because of the way things look, right? I think Instagram has made has made work look exciting and like you could have a new life and have a new identity. but it is still a grind, know, like it is still all of the, all of the steps you have to take and learn. It's a lot of learning really, you know, it's a huge learning curve. And I think we get asked a lot, you know, like, how do I do this? And it's like, do you really want to know? Are you sure? Right. And I think it's also, you know, do you want to do the work, right? Do you want to learn? I listen to you talk about things like revenue and we're doubling our revenue and we have to get mortgages and contractors and loans, construction loans and things like that. That's not part of the picture, right? That's like the behind the scenes. Here's where we really do the grind to make sure that the vision can become a reality because visions don't just accidentally become realities. The opportunities might come up fortuitously. but you have to be willing to step into those opportunities with a lot of grit and determination. Yeah, I would say, know, definitely as an entrepreneur and especially in the hospitality space, which is a creative industry, no matter how you look at it, there's no roadmap. And you really have to bet on yourself and like fully believe it or like you just, you don't grow, you know, it's like, even if it's, even if you stay small and just do the one, you really have to like. you have to you have to own it, you know, you have to feed it. And you have to let it grow. You said something interesting as well a few minutes ago about you can't replicate yourself enough to grow, right. So you have to be able to bring other people into the story and make them a part of the story in a compelling way. I'm sure that's been challenging for you and your partner as you've expanded to different properties. Julie Williamson, Ph.D. (14:09.356) And you as a human can't be boots on the ground in four places at once. So there has to be a degree of trust, but also of imprinting people into the brand or making sure that they are representative of the brand. What does that look like for you as you've worked to build up these different properties in ways that are unique to the property, but consistent with the brand that you and your partner. have worked so hard to build? So, you know, our brand started as just us. And it's kind of, I would say as we grew it, it was kind of us telling our story. And it was like, I say the grand grew with us, it matured with us, you know, as we, you know, we started with properties that didn't allow kids when we opened the lodge, I was pregnant, all of a sudden we were like, Sure, kids can come. That's So each location is a new time stamp of basically our lives and ourselves. And bringing people into that story has been a big challenge. And I would say we didn't even understand. even after we opened Nashville and kind of got our footing with like a team that we felt was really great. You know, company culture was a term that didn't even come to us until probably the pandemic when we had to shut down and like, while we were opening the lodge and kind of like understanding this idea that like maybe we needed more than just a storyline to feed people that we needed to create some kind of container for them to exist in and like a real education system that was truly organized, know, the organization of managing people and giving them something that's purposeful for them and something to own is really important. You know, we're small. Our team has typically been two people to, at one point in our like, Julie Williamson, Ph.D. (16:26.046) riding the post pandemic wave that rose all the ships, it was seven, but that didn't last very long and it went quickly back down to like three. So, you know, the decision makers, there's not a lot of room for growth, you know, and it's a revolving door on the service level. so, you know, having company culture is like a real, it's actually crucial to having people be on board, which is also something that like I didn't... know how to do at all. You can have all the ideas. I'm like company culture means like, you're looking at like a company like Google and you're like, free snacks and like, right? I'm like, what does it mean? You know, like we have a holiday party. Like I don't, you know, it's a lot more than that. You know, it is the exam, especially when there's not a lot of room for growth. There's no, there's no ladder to climb. It's like, be a part of something that's bigger than you and love it every day and feel like there's a growth within your role. yeah, people an identity within your brand is... huge. How would you describe the company culture today? I would say that our company culture is, you know, each, so I would say each property is its own kind of microcosm. They all have their own climates. They all have, you know, one or two people in leadership that carry out our vision. And those people have typically been with us for many, many years and kind of understand, they fill the gap between lion who is Julie Williamson, Ph.D. (18:11.17) definitely the visionary of the brand. It's more so his baby and me who kind of translates that. And then they kind of act it out and like, it's artist do. And then they bring people up into that. it's kind of, but it's definitely like, would say, you know, we, we, we are less precious than we were in the beginning. And I think that's a huge step into company culture is like, it can't. with service, especially, with, you know, it's not just like, we're not selling a product that you can put out on a shelf that has a price tag on it that people come in and they look at it all on all four sides and say, I'll buy it. We're selling an experience. So you have to let people be themselves to a degree, to a barrier, and with it that fits within your brand standards and your values. And so I think and the expression of values and standards and, you know, carrying those out is a huge part of what our company culture is now, and especially on property and allowing people to really embody those and feel free to expand on them and elaborate because everything changes all the time. It's an industry you have to pivot in quite quickly. know, there's trends, there's, locale has a different kind of idea of what is important and what is priority. Like skiing is really important in Colorado and it's definitely not important in Nashville. So it's like, how do we, what is the market there? What is our client? And even though it's a giant family of products and homes where we like are encapsulating our customer, we want our staff to feel that what is important to them is important to us and that they can express it. because they are boots on the ground. What I'm hearing you walk through here, Jersey, is such an interesting articulation of what a more academic view of culture would support, which is that it's reciprocal. It's not one directional. So it's not you saying this is the culture that you need to have in each of these properties. It's really you being open as an owner, you and your partner. Julie Williamson, Ph.D. (20:34.412) to continuing to learn and grow with your colleagues who are boots on the ground and the properties saying these are things we need to adapt to. These are things we need to incorporate into what we do here that do fit within your vision of what you want Urban Cowboy to be all about. And I really love that that's such an organic expression for you in terms of how you go about nurturing the culture. that you would like to see in these different properties? Because I think a lot of people don't quite get that. It has to have that reciprocity in it in order to be successful over time. I would say you're spot on. I think in the beginning, that was kind of our whole hospitality model to begin with. It was about eliminating this kind of fourth wall between guest and host. Our service model was about connecting with people and not servitude to an extent, you know? And so that helps make community, it helps make a different kind of loyalty, you know, in a consumer. It is niche. And in a colleague. And in a colleague, yes. And so that translates, you know, can't have that be what you want someone to put out without having it be the thing that trickles down from the top in terms of how we interact with our employees is the same as how we interact with our guests. That's, you know, it should be the same on both sides. I think you just hit the nail on the head in terms of how do you successfully build culture, right? That's it. Don't expect people to put something out to your customers that they're not receiving inwardly from you as a leader or as an owner or whatever the model, business model happens to be. Exactly. Yeah, I think that's a really important point. So we go back to the idea of the failure gap and what do people agree is a good idea and what do they struggle to align to? I do think building culture is one of those things where a lot of people sort of give it lip service and they say, yeah, it's a good idea. We should have a strong culture. I'm never really sure what that means. But what I'm hearing you really dial into is this idea of culture is important because it actually makes you more replicable, if that's a word, right? So how do you help? Julie Williamson, Ph.D. (23:00.622) how do you expand and grow the brand without needing to be the person who is holding the culture in each location? And you do that by building this self-reinforcing model where you are listening and growing with your colleagues who are doing the work of delivery in the different sites. Yeah, exactly. my love one. When you think about what holds people back from... doing that or maybe aligning to leading in that way. What do you imagine makes that hard? What scares you about it maybe or what makes you nervous about it? I mean, we definitely failed at it in the beginning because we were, like I said, less precious with it now. We held it so close to the chest and we wanted people to act the same way that we act. And that isn't the same translation, right? It's not being like me. Yeah. They're not carbon copies, right? They're not. They're not carbon. Yeah. Not androids, but what do you call that when you replicate a clone? Is that a clone? Clones. And that's hard, you know, and it's also, like I said, it's an industry where there is a revolving door and we end up hiring a lot of young people because, people younger than ourselves, I'm still young. And, you know, so there's there's a cultural gap already just because we're hiring Gen Z. They're not millennials. We're kind of like at the end of that. And so they have a different way of thinking about things and definitely thinking about what work is. bridging that gap is hard. so, yeah, you can't expect people, have to leave enough of yourself in it that they understand your vision and your goal, but you can't expect them to be you. You have to allow them to be themselves. And that allowance needs boundaries, right? But it has to happen. And part of that allowance is like, you have to let them fail, which is hard when you're small, because you don't have a lot of buffer for failure. Julie Williamson, Ph.D. (25:24.726) Right. But in order for them to get the experience that you have, you have to let them fail a little and then like learn from their failures, which is like a big one. Yeah. That's scary. Can you give an example of where that has played out for you? So, I mean, you know, every time we open a property, it's a big lift. there's a lot on the line in terms of timing and getting things open, which is a struggle when you are doing construction and contractors are your best friends and your worst nightmares all at the same time, right? Because they will placate you even if they don't know to keep the work going. you know, they do things wrong and you didn't express things clearly and you know, there's like a lot of artistic decisions that get made on their behalf that you don't agree with, et cetera. But when you have a team in place on the ground that's running a project for you, because you can't be there all the time, when you have projects in multiple locations, that's just how that works, you can't be there. And... with the experience that we have running a project is entirely different than what your team may have. And your team that's on the ground probably isn't a project manager when you're small like us. It's probably like your GM and like your whoever is gonna be opening. They're doing everything. It's probably whoever is gonna be actually opening the doors to that property, getting this like service model set up. And so the things that you need them to care about, they're not programmed necessarily to care about such as, you know, your construction budget versus like your opening budget versus, you know, like just having people that need to be multifaceted on a small team that just don't have those skill sets and allowing them to kind of take ownership over things and then kind of failing to communicate that they don't know what they don't know has been a struggle. And so, but that's it. They don't know what they don't know. They don't know how to... Julie Williamson, Ph.D. (27:52.738) had to the questions or, cause you know, it's beyond them. And sometimes it's beyond us too, even as owners and people who have all of the experience in doing that already, right? But so it's like, it's hard to not blame in those moments, you know, and like to hold, you know. to create real accountability in a situation like that. And like who, you to, cause you kill morale when you do that, right? Like you kill the morale of this opening excitement when you're like, well, it's your fault. We didn't do it on time and it's your fault that this thing isn't happening. And they're like, that's not me. It's not my job. know? Yeah. Yeah. It's hard. And I think what you're pointing at is that as a leader, we often say you have to hold people accountable. but then accountable can look really terrible if you come down hard on somebody and then you lose them or they check out or it damages the relationship, but you still have to do it. And I think the leaders that come at it with a sense of compassion, as well as allowance for the learning, while protecting the vision, that intersection of compassion, allowance and protection. It's very difficult, but I think if you can aim for that as a leader, sometimes you can land it. in the different things that you've been talking about, I'm hearing those threads coming through about wanting to show up for people with a degree of compassion for where they are and allowance for their learning, but at the same time, being able to be firm about protecting the vision that you have. Yeah, exactly. And you said it can damage the relationship and that's absolutely, for us it's been absolutely crucial to the way that we get properties open and a big part of the culture. We've had people that have been with us for a long time and when you're this small, there tends to be some gray area between employee and friendship and they're in close and especially if your brand is as Julie Williamson, Ph.D. (30:12.142) close to your life as it is to ours, it can feel very intimate. And so, yeah, those relationships are really precious. And so it's kind of like... when you start to discipline or hold people accountable, it can feel like you're not on their, it's not the friend side anymore, right? It's the boss side. And that is, that's a nice little tug of war. Yeah. Yeah. It's a delicate tug of war. Yeah. think, especially in these smaller businesses, like you said, I think that can be really, really tricky. And you want to hold on to both the friendship and the business relationship, but also, you know, equally committed to driving the business success. Exactly. Yeah. Yeah. This has been so interesting, Jersey, as we take a walk through your world of entrepreneurship and something as ambitious as standing up hotels across the United States. Like there is so much grittiness in that, right? Like you have to build things, you have to bring a vision to life. And the way that you are talking about bringing it to life with a culture and with a resonance for your colleagues as well as for your customers. I think that's really inspiring to hear you talk through and share your learnings with that. So I really appreciate hearing that story. Again, I think the age of Instagram, we're used to seeing the beautiful pictures of the hotel rooms and people staying there and everything else and getting a peek behind the curtain is absolutely... It's so interesting. I could talk to you probably for hours, but we don't have hours. What I would love to ask you is if someone is listening who is thinking to themselves, I'm an entrepreneur at heart. I really want to have my own business. want to stand up. I have a passion for something. I want to stand it up. And they're sitting with that agreement. They're like, yeah, this is a really good idea that I have, but they're having trouble really getting aligned and getting it done. Are there two, three things that you would say to them? Julie Williamson, Ph.D. (32:17.262) You know, just here's a way to get going. I would, oh wow. Okay. So I would say, know, there is no, um, again, there's no roadmap for sure. Don't look for a roadmap. That might be job one, right? Don't look for a roadmap. think the less plan you have, the better. Like it's going to be a work in progress and you're going to have to shift. In the beginning, you're going to have to shift at every single moment to see what works. And you have to like actually do a lot of listening. You have to like take a step and listen what to what comes back at you. But if you really believe it's a good idea, just go for it. You know, like it's kind of that simple. You have to just do it. Make it. Make it. Make it happen. however that needs to happen, know, however that, because the worst thing that's going to happen is that you're going to fail and you're going to learn something, right? So like, um, it, and hopefully it doesn't get too big before it fails, right? Like it doesn't get out of, don't, you know, you don't want to hurt anyone in the process. Um, but including yourself, including yourself, but yes, I would say just take that first step. Um, and if it feels like an, active expression, don't definitely don't hold back, know, expression is one of the more risky things that we do as entrepreneurs, right? Because there's always some self in there. And I would say definitely don't hold back in that aspect of it, you know, put yourself out there and listen again, like that's a huge one. Listen to the feedback, listen to what comes back. We would not have expanded if we hadn't heard people saying, go to Nashville. You know, we listened, we were like, Oh, they'll give us money if we go to Nashville, 100 % in, you know, like, who cares about what we had ideas about, like, we're going, right, you know, I love that idea of listening, because I think and also the other thing that I'm hearing from you is learning, listening and learning are two things if you are sitting on a really good idea, and you want to get going on it. Julie Williamson, Ph.D. (34:36.704) Listening to that feedback and also be willing to learn along the way you don't have to have it all figured out before you get started I think Jersey. I don't know about you, but I see that that right there that mindset holds people back I don't have it all figured out so I can't get started. You're like you can't figure it all out if you don't get started Yeah, you will overwhelm yourself trying to answer a question that has not been asked yet, you know Yeah, it's all work in progress. I feel like if somebody had asked you 10 years ago, what are the details that I need to know about a construction loan? You would have been like, I have no idea. You didn't need to know that. You didn't need to know that to get started. You just needed to get started. And then that became something that you learned along the way. Exactly. Like I said, like I didn't know what a credit card processing machine was when we opened. I, I didn't, I, you just do it. You just say, cut. Come take part in this thing and and see what people say Figure it out and then figure it out quickly. Yeah Yeah, yeah, in yourself to figure it out You know if you if you have a good idea and you believe that you can figure it out as you go You can yeah, I always like to remind people that optimism is not thinking that things are easy But it's believing in your ability to do hard things and so you can be optimistic about yourself and your ability to do hard things And there will be some hard moments standing up a business, but you can find your way through it, especially if you are open to listening and to learning as you go. Yes, absolutely. Yeah, yeah. Jersey, we asked one final question of everybody. If you could get any group in your life, whether it's a community, maybe your colleagues, someone with your family or the world at large, whatever space you wanna pick to get aligned and do something together. What would you like to see people come together to do? Let's see, I would love if people could get aligned. that's a good one. I would love it if... Julie Williamson, Ph.D. (36:53.61) So I have this thing with old bathtubs and I love an old cloth tub and I really wish people could get aligned around not using the like shower curtains and then to like when there's like a shower old cloth combination, like can we get aligned around figuring out like a hard glass solution that's like easy to clean and just more functional, less like gross, it doesn't like cling to you while you're standing in the shower and like, like a couple inches of water. Like, I would really love that. Like I don't understand why it doesn't exist. And it really should. Yeah. Yeah. Let's fix that. I agree. Let's fix that problem. Give the glass can be so beautiful, but it is hard to clean. And so then you've got that trade off. my gosh. Yeah, I'm a big functionality person. And I just don't understand the function of using two shower curtains to circle a cloth at time. All right, we're gonna put that out there in the world and see if someone can solve that for a Jersey. She would love a better solution for her cloth at time. Thank you so much. I really enjoyed this conversation. It's been great to hear about your journey and entrepreneurship. Good luck with the brand and the expansions that I know that you have coming up. And we'll look forward to hearing more and more about Urban Cowboy and other things that you have underway. as we go forward. Any final words for our listeners? No, I just, I wish you all luck in your entrepreneurial adventures. Yeah. Thanks for that. And thanks to you to all of our listeners. Just a reminder, if you like this episode, to share it with your friends and we will see you next time on the Failure Gap.