This week marks a huge milestone — 150 episodes of Outside The Circle! We’re celebrating with an inspiring conversation with Bobbii Jacobs, founder & CEO of Wildflower Entertainment Group and the visionary behind Heartland, the event that raised over $100,000 in 22 minutes to support mental health resources for farmers and ranchers.

Bobbi shares her journey through the ever-changing music industry, from driving Matchbox Twenty across the country to mentoring new artists finding their sound and purpose. It’s an episode packed with heart, hustle, and hope for the future of country music.

Tune in now for a mix of real talk, big lessons, and behind-the-scenes stories from one of the industry’s true connectors.