I Want Her Shoes Podcast | Episode 82 | The Art of Gathering

with Cynthia O’Keefe & Simon Sorpresi

What transforms a beautiful building into a place people never want to leave?

This week on I Want Her Shoes Podcast, host Anna Anisin welcomes Cynthia O’Keefe and Simon Sorpresi, the creative and entrepreneurial duo behind The Moore Miami—a destination where hospitality, art, design, business, and culture come together under one roof.

Together, Cynthia and Simon have built more than a remarkable venue.They’ve created a space where ideas are exchanged, relationships are formed, artists are celebrated, and community comes to life.

In this conversation, Anna explores what it takes to build meaningful experiences, lead as partners in business and life, and create environments that people remember long after they’ve left. Because great hospitality isn’t just about service. It’s about creating a sense of belonging.

👠 Key Moments

  • How Cynthia and Simon built a business—and a life—together
  • The vision behind The Moore Miami
  • Why hospitality is really about human connection
  • Lessons from decades of entrepreneurship and leadership
  • What makes unforgettable spaces unforgettable
  • The future of luxury, culture, and experiential hospitality
  • How AI may change hospitality—and what should always remain human
  • The role of style, architecture, and design in shaping experience
  • Building a lasting legacy through community
  • The stories behind the shoes they brought to the podcast

This episode is a celebration of creativity, partnership, and the people who understand that the most meaningful experiences aren’t manufactured—they’re thoughtfully designed.

🎧 Listen now and discover why the greatest luxury isn’t a beautiful space—it’s how that space makes you feel.

Adding a chic twist to each episode, the ‘I Want Her Shoes Podcast’ is recorded in Anna’s stunning personal closet, strategically located near the vibrant Miami Design District. This unique setting not only provides a visually captivating backdrop but also embodies the spirit of fashion and innovation that the area is known for. 

📺 Watch the episodes on YouTube to get a glimpse of this one-of-a-kind Miami closet—it’s definitely worth the view!  https://www.youtube.com/@IWantHerShoesPodcast

Follow us for more updates:

The Moore: mooremiami.com 

IWHS Pod Instagram: https://www.instagram.com/iwanthershoespodcast/

IWHS Pod Website: https://iwanthershoes.com/ 

Cynthia’s Instagram: https://www.instagram.com/cynthia_okeefe

Simon’s LI: https://www.linkedin.com/in/simon-sorpresi-3504a922/