EP 45: Iteration and the Art of Building Connection with Félix Medina

Episode 45: Iteration and the Art of Building Connection with Félix Medina

Hosted by Katelyn Calhoun

This week on Crafted Connections, I’m joined by my longtime friend and collaborator Félix Medina for a wide-ranging, honest conversation about identity, entrepreneurship, and what it really means to build meaningful connections with other humans.

Félix and I have known each other for nearly a decade, and this conversation reflects that depth of history. We talk openly about his upbringing in a border town—growing up not just bilingual but bicultural—and how those early experiences shaped his curiosity, adaptability, and love for people. His story is a powerful reminder of how environment and exposure quietly influence the paths we’re drawn toward.

From there, we dive into entrepreneurship as both a creative and spiritual journey. Félix shares what it’s been like to build, sell, and experiment with multiple ventures over time—learning through iteration, missteps, and reflection. We talk about the myth of stability, the tension between freedom and security, and why both traditional employment and entrepreneurship can feel misaligned depending on who you are.

A recurring theme throughout this episode is experience—the idea that every interaction, meeting, and conversation is an opportunity to create something meaningful, even if it doesn’t lead to a sale or a concrete outcome. We explore curiosity as a practice, daydreaming as a creative tool, and why real connection often matters more than optimization.

This episode is thoughtful, funny, and deeply human—a reminder that growth isn’t linear, identity is fluid, and the best work often comes from staying open, iterative, and willing to learn in public.

What You’ll Hear in This Episode:

🌍 Growing up bicultural and how that shaped Félix’s worldview
 🧠 Entrepreneurship as a creative and spiritual practice
 🔁 Why iteration—not perfection—is the real growth strategy
 🤝 Seeing every interaction as an opportunity to create an experience
 🎭 How curiosity, daydreaming, and play fuel innovation
 ⚖️ The tension between freedom and stability in work and life
 🧭 Why entrepreneurship isn’t for everyone—and neither is traditional employment
 🔥 Staying aligned with your “flavor,” even when it risks rejection
 💬 The power of presence, listening, and human-to-human connection

Connect with Félix:

📍 Website: https://www.elcapdm.com/

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Join the Conversation:

📲 Instagram: @CraftedConnectionsPod
📬 DM me your thoughts or guest suggestions. I love hearing what resonates.

Crafted Connections is lovingly produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.

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Keep creating, keep connecting.