From Solo Ventures to Team Management: Caleb Benoit’s Leadership Story
On this episode of Leadership LevelUp, Jeff Williamson sits down with Caleb Benoit, the innovative founder and owner of Connect Roasters. Benoit, an entrepreneur deeply rooted in his hometown of Bourbonnais, Illinois, discusses how his passion for quality coffee and community spurred the creation of his business.
Caleb Benoit, an impassioned entrepreneur based in Bourbonnais, Illinois, started Connect Roasters eight years ago. What began as a one-man operation sourcing and selling coffee soon grew into a comprehensive enterprise boasting its own roastery and a popular brick-and-mortar cafe. Caleb’s vision and tenacity have positioned Connect Roasters as a community favorite and a shining example of small business success.
In this insightful conversation, Caleb shares the pivotal moments that prompted the growth of his team, the challenges of managing a dual-operation business, and the crucial role of communication in effective leadership. From roasting coffee in-house to hiring baristas and expanding into full-scale fulfillment, Caleb opens up about the learning curves and leadership lessons he’s embraced along the way.
Listeners will gain an intimate look at the behind-the-scenes workings of a coffee business, the importance of developing standard operating procedures, and the fascinating art and science of coffee roasting. Caleb’s commitment to education is evident as he talks about the coffee classes Connect Roasters offers and his drive to share knowledge with coffee enthusiasts and the wider community.
Jeff and Caleb also explore the vital role of community development, emphasizing how local businesses and volunteering uplift a community. Caleb’s sincerity and dedication are infectious, making this episode a must-listen for aspiring leaders and coffee lovers alike.
Tune in to learn valuable leadership lessons, hear about the complexities of running a dual-faceted business, and get inspired by Caleb’s story of entrepreneurial growth and community involvement. Connect Roasters is more than just a coffee shop; it’s a testament to the power of vision, hard work, and the strength of community ties.
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To learn more about Connect Roasters, visit their website at connectroasters.com or follow them on social media. Caleb and his team are always ready to bring the best coffee experience to your next event or answer any coffee-related questions you might have.
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Meet The Guest

Caleb Benoit
Caleb Benoit is the founder and CEO of Connect Roasters, a mission-driven coffee company that operates a coffee roastery and brick-and-mortar cafe.
Connect’s mission and giveback model have funded tens of thousands of meals for people in need, both domestically and internationally, and its business partnerships include companies like Goose Island Beer Co. and the Chicago Cubs. Before founding Connect, Caleb worked in software and journalism, and he’s worked internationally in both Europe and Canada. He, his wife and their two children live in Kankakee, Ill.
About the Leadership LevelUp Podcast
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. Jeff, being a leader of leaders, has a vast knowledge of best practices and exercises to discover leadership traits. Brian shares stories with Jeff about the ups and downs of his leadership quest while talking to business and community leaders to discuss their personal leadership journey. Who influenced them? What do they do when they have a bad day? What gives them inspiration? Do french fries or tacos or ice cream make them feel better after a bad day? Through laughter and casual conversation, Brian and Jeff explore all aspects of good leadership.
Meet The Host

Dr. Jeff Williamson
Dr. Jeff Williamson is the Founder of Converge Group Inc. an executive coaching and people development practice. Prior to launching his business in 2017, he was a Dean, Executive Director, and Professor of Organizational Leadership serving in higher education for over 30 years.
He holds a bachelor’s, and master’s degree in Speech Communication, and a Doctor of Education degree (Ed.D.) in Educational Leadership and was a post-doctoral student at The Ohio State University, Fisher College of Business. He is the host of “Leadership LevelUp” podcast and is also a Gallup-certified Strengths Coach.
He regularly teaches and speaks to business and industry on topics such as: Personal Leadership, Leadership Paradigms, Leading Change, Discover Your Strengths, Building a Strengths-Based Organization, Coaching, Mentoring & Conflict Resolution.
Show Sponsor
Pathfinder: A full-service creative & marketing agency with a mission to provide strategic storytelling to our clients. There is no greater impact in this world than a story. Storytelling is how we learn, remember, and feel. The world has used storytelling since the beginning of time to entertain, teach, inspire, and innovate. Pathfinder’s mission is to provide strategic storytelling for our clients. How? Through inventive business services and pioneering campaigns that help organizations find their own path and carry out their vision.