History

Samuel Kilgore’s Podcasting Journey: From Joy Rides to Deeper Conversations

Samuel Kilgore’s podcasting journey began behind the wheel with a show called “Joy Rides.” He’d pick up friends, creatives, and entrepreneurs, hit record, and cruise through town while diving into honest, spontaneous conversations. The car was more than transportation—it was a space where people let their guard down and shared real stories.

As time went on, Samuel noticed a pattern: his guests weren’t just talking about their work—they were unpacking their journeys, struggles, and what it really took to build something from scratch. That realization sparked the creation of “How to Entrepreneur,” a podcast focused on the people behind the business. It offered a closer look at the emotional and practical challenges of building a dream.

“How to Entrepreneur” moved online via Zoom to accommodate guests from all over. It was flexible and efficient—but something was missing. The magic of in-person connection, the nuance of body language, the unspoken energy that filled the gaps between words.

So Samuel built a studio.

The moment he brought guests into that physical space, everything changed. Conversations deepened. Stories unraveled more naturally. It became clear that the best storytelling happened face to face. The studio wasn’t just a recording room—it became a space for connection, reflection, and learning through people’s lived experiences.

Now, with shows like “Bears Don’t Fly,” Samuel continues to explore the human side of creativity, business, and life—one conversation at a time.