EP 38: SOLO – End of Beginning – The Story of Saying Goodbye to My First Company

Episode 38: SOLO – End of Beginning – The Story of Saying Goodbye to My First Company
Hosted by Katelyn Calhoun

This week’s Crafted Connections is a solo episode — one that’s both tender and transformative.

In honor of National Entrepreneur Day, I’m sharing the full story behind closing my first company, Teardrop Pictures, and what it means to finally say goodbye.

For eight years, Teardrop was my creative home. It was where I grew up as a filmmaker, storyteller, and entrepreneur — learning hard lessons, building community, and creating work I’m deeply proud of. But when it came time to evolve into Calhoun Creative Consulting, I realized I never gave myself space to truly close that chapter.

So I took a trip back to Indianapolis — to the coffee shops, breweries, and streets where it all began — to honor that season, celebrate what it gave me, and let it go with gratitude.

This episode is about endings, beginnings, and everything in between. It’s about the courage to release what no longer fits and the grace to see how far you’ve come.

If you’ve ever outgrown something you once loved — a business, a dream, a version of yourself — this story is for you.

What You’ll Hear in This Episode:
🎬 The story of starting Teardrop Pictures as a 24-year-old filmmaker
💡 Lessons learned from eight years of entrepreneurship, growth, and failure
🏙 Returning to Indianapolis to find closure and reflection
💭 The power of letting go and redefining success
🌱 Why endings aren’t failures — they’re fertile ground for what comes next

Need Help Shaping a Story That Actually Feels Like You?
Book a Story Strategy Session.

At Calhoun Creative Consulting, we help individuals and teams clarify their message, uncover what matters most, and share stories that resonate. Whether you’re reworking your brand, launching something new, or just feeling foggy about how to talk to your people — this is where clarity starts.

🎥 Book your session and use code PODCAST for 25% off:
https://katelyncalhoun.as.me/story-strategy-session

Join the Conversation:
📲 Instagram: @CraftedConnectionsPod

📬 DM us your reflections, stories, or goodbyes you’ve been meaning to say.

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.