The Art of Gathering
I Want Her Shoes Podcast
In this episode of 'I Want Her Shoes,' host Anna Aniston sits down with Cynthia O'Keefe and Simon Serp-Ressi, the visionary partners behind
Key takeaways
- Great hospitality is not about service alone—it's about creating a sense of belonging.
- Unforgettable spaces are built on human connection, culture, and community rather than just architecture or design.
Main topics
- Hospitality as human connection
- Entrepreneurship and partnership in business
Notable quotes
"Great hospitality isn't just about service. It's about creating a sense of belonging."
Conclusion
Cynthia and Simon's story illustrates that true success lies not in physical spaces
Transcript preview
Speaker 2 (0:00) Hi there, this is your friend Anna. And the question that I've been getting the most from all of my friends is what are we wearing? This age-old question isn't just about choosing an outfit. It's about choosing how we present ourselves to the world. I created the I Want Her Shoes podcast to dive deep into what it means to dress with intention, whether you're heading to a council meeting or just having a casual day out with your family. Join the conversation as we explore the power of personal style and the decisions that shape our public personas. Put on your favorite pair of shoes and step into my closet. Welcome back to the I Want Her Shoes podcast, where we explore ambition, creativity, reinvention, and the people building lives with intention. I'm your host, Anna Aniston. And today's episode is a little different because today I'm welcoming not one guest, but two. Yay. And together they built something that's become one of Miami's most extraordinary cultural destinations. And when people think about hospitality, they often think about restaurants, hotels, beautiful interiors, great food. But today's guests remind us that most memorable places aren't built with furniture. They're built with a feeling, with culture, with community, with the people in those places, right? And the Moore Miami opened just a couple years ago, 2024. It's a real new space where hospitality, design, architecture, art, and cultural... really intersect and come together and bring those amazing people together. And Simon Serp-Ressi joined The More in 2025, right? To help steer the club into its next chapter and really shape the evolution of what it has become today, Speaker 3 (1:54) which Speaker 2 (1:54) is a really cool destination. And alongside him is his beautiful wife, Cynthia O'Keefe, who is a creative director of The More and founder of O'Keefe Hospitality, entrepreneur, advisor, investor, and someone who has spent decades helping organizations Organizations create extraordinary experiences, which are so important. And together, they're not just building beautiful spaces. They're creating places where people have unforgettable experiences and where ideas begin, where businesses are born. where artists are discovered, and where communities grow, which is really important because I have a community. So the more places we have for community, the better. And today we're talking about entrepreneurship, hospitality, creativity, leadership, partnership, design style, and what it really takes to build places people never want to leave, right? Nice to have you guys here. Thank you. Speaker 3 (2:45) And Speaker 2 (2:45) before we dive in, let's start from the beginning. How did you guys meet? Oh, wow. Yes. Well, Speaker 3 (2:55) first of all, thank you so much for having us. And what I'm loving about our space right now is all the gorgeous fashion. I found this in New York City. That's exactly where we met. I moved there straight out of high school. Made it my home for many years. And that is where I ended up meeting my husband. Just Speaker 1 (3:13) 2001. Wow. So Speaker 2 (3:17) it's been a while. We Speaker 1 (3:19) just celebrated our Speaker 2 (3:20) 20... Well, Speaker 1 (3:21) we Speaker 2 (3:21) have an issue. Speaker 1 (3:22) We're Speaker 3 (3:23) really busy people and sometimes we forget. Are we together 21 years? 23 years? And what's the barometer? Is it when we met, doing business together? I feel like it's when you go on your first Speaker 2 (3:36) date. Or Speaker 3 (3:36) no, when you actually commit to each other. Well, it's funny. How do we actually look at this? That's a good segue into your next moment. Probably. Yes, we were actually, it was more Speaker 1 (3:47) business before. It was in New York City, Cornelia Street, a restaurant, Palma. It's still there, actually. It's still there. That's where we ultimately met, yeah. Speaker 2 (3:57) I love that. See how distinct this memory is. And then after meeting, at what point did you realize you could actually build something together? I Speaker 3 (4:06) will admit our connection really was business. He had just come from Switzerland. He had some pretty big goals. And at that point, I'd been in the New York hospitality scene for a while. As soon as I met him, I'm like, hmm, what's going on? what project are you working on? And does this work with Speaker 1 (4:24) what I'm doing? So that was... I think we had, if I may, we had the actual possibility to create multiple times. something on a business level and we got more engaged on a business level first. I mean, there was always an attraction, clearly, but it was actually on a business level we were engaged first. And I was in New York and then now many, many years after with the more we have again, that opportunity, that possibility to create something special from a business level. He Speaker 3 (4:49) was opening up a space on the Lower East Side. You know, I was a Manhattan girl through and through. And at the time I was working independent restaurants on the kind of like across from Lincoln Center, so Upper West Side-ish. And when I heard that he was creating on the Lower East Side, I was like, okay, what are these concepts? What are you doing? That was an early conversation. Speaker 2 (5:08) Love that. And working with your spouse sounds amazing and also incredibly challenging at the same time. Speaker 1 (5:19) How Speaker 2 (5:19) do you guys divide your responsibilities? Like, is there somebody that has certain strengths, like, versus the, you know, like, so it just Speaker 3 (5:27) goes. Yes. And that is it. It wasn't so much of a division where it was a, hey, we're both really passionate about this. And which one are we going to do? We just. had, I think, natural skill sets that we were developing and we were gravitating toward, you know, our entrepreneurial game was strong Speaker 1 (5:44) early on. We were like... And Speaker 3 (5:46) I Speaker 1 (5:46) think also, I mean, the thing is in New York, so we had twice the ability to create something special, we believe. In New York, it was much more intuitive, I think. So the strength of yours, the strength of me, we kind of found our kind of grounds how to... work with each other. Now, at the more, it's a little bit different because I have a different role and it was also a different timing that we got on board. So that was a little bit more structured, I think, than the initial New York time. For sure. Speaker 3 (6:09) Like now in this day and age, we have very specific roles and goals. But challenging things for me is when I do need to speak with him about business is having to wait to get on his calendar. So Speaker 1 (6:22) I'm Speaker 2 (6:22) like, that Speaker 3 (6:23) feels odd, but I have to do it. You Speaker 2 (6:25) can't carry that into your person. Speaker 1 (6:29) You'd think it would, but no. And it mixes, I think, a little bit. Especially if we go quite often. If it's Speaker 2 (6:35) an emergency, yeah. We go quite often for a morning walk at the beach. Yeah, we do a morning ritual. That is Speaker 1 (6:40) quite kind of like digestion and exchange with each other. We try not to inundate too Speaker 3 (6:46) much Speaker 1 (6:47) work Speaker 3 (6:47) stuff, but it Speaker 1 (6:47) happens. It happens. What is Speaker 2 (6:49) one thing that Cynthia does better than anyone? Speaker 1 (6:52) What is one thing that's... She's the absolute total package from an intelligence, but also a very emotionally intelligent person. Has extremely the finger on the pulse of what the zeitgeist is and is able to convert that into the business. I think that's a very kind of a superpower of yours. Speaker 2 (7:08) That's awesome. That's a great answer. And I was going to ask you about his superpower as well. He can fall asleep easily. I'm so envious of this. Speaker 3 (7:22) but no i said that off the cuff but that is actually a byproduct of of his actual superpower which is i have never in my life met anyone who can compartmentalize so beautifully and i cannot do that it is very challenging for me to separate where do this i'm learning yeah i feel like i don't have Speaker 2 (7:44) to do it i mean some days are better Speaker 3 (7:47) than others And his ability to compartmentalize allows him really to excel in different areas. I respect it. And he can fall asleep early. Thank you. Thank you. Because Speaker 2 (7:59) he can turn off all those things. They're like, okay, I'm out for a second. Phenomenal, babe. Truly. And what is one thing that absolutely drives you crazy about the other one? Speaker 1 (8:10) About the other one? Yes. Do you want to go first? Mm-hmm. Speaker 1 (8:15) I think Speaker 3 (8:16) it's also the thing that I love about him. It's his steadfastness. You have this unshakable quality. Okay. While that can be great in some circumstances, others... Frustrating. It's not the Speaker 1 (8:34) first time Speaker 3 (8:34) that Speaker 1 (8:34) I hear that, by the way. And Speaker 3 (8:36) I'm working on it. But do you need to? You might not be the problem, just so we're clear. I mean, you know, I got that part, but yeah. Speaker 1 (8:45) Okay, my turn. Well, actually, it's Speaker 3 (8:47) a Speaker 1 (8:47) little bit similar. I actually enjoy that the input that you give, but occasionally it drives me crazy. My attention span is super short and moving very fast. And if there's something that you want to go more into depth and explain, I'm like, okay. Let's go. She's like, wait. Speaker 2 (9:03) And she's like, no, no, Speaker