From Solo Ventures to Team Management: Caleb Benoit's Leadership Story Artwork

Leadership LevelUp

Being a boss and a leader are very different. A boss tells you what to do and a leader partners with you in the process. Our hosts, Brian Prairie and Dr. Jeff Williamson, explore leadership from different ends of the spectrum. Jeff has been exploring leadership and guiding leaders for 30 years. Brian, new to leadership, keeps asking himself what makes a good leader, as his role continually evolves at the marketing firm, Pathfinder. He and Jeff talk to leaders about their guiding principles and inspirations in a quest to look at leadership in all its forms.

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Leadership LevelUp

From Solo Ventures to Team Management: Caleb Benoit's Leadership Story

March 17, 2025 • Dr. Jeff Williamson • Season 9 • Episode 63

Today we are excited to reconnect with Caleb Benoit, the founder and owner of Connect Roasters, based in Bourbonnais, Illinois.

In this episode, Caleb shares the journey of transforming his business from a one-man operation into a thriving enterprise with a cafe and a dedicated team. He opens up about the challenges and rewards of leadership, especially the importance of communication as his team grew. "You become focused more outward. Everything cannot live inside of my head," Caleb reflects, emphasizing the shift in mindset from solo-preneur to CEO.

We explore the intricacies of the coffee industry, from the roasting process to community engagement through educational courses and events. Caleb reveals the excitement of tasting sessions and how Connect Roasters is more than just a cafe – it's a hub for learning and connection.

Finally, the episode delves into the balance Caleb strikes between running his business and uplifting the local community, inspiring fellow entrepreneurs and community supporters alike. Whether you're a coffee enthusiast or business leader, Caleb's experiences offer valuable perspectives on growth and community leadership.

So grab your favorite brew and join us for an episode rich in insights, local flavor, and the spirit of entrepreneurship. Don't forget to subscribe for more conversations that inspire and elevate.