All Episodes 159: Caleb Benoit | Brewing Connection: Coffee, Business & Family
159: Caleb Benoit | Brewing Connection: Coffee, Business & Family
Caleb Benoit is the founder of Connect Coffee, a roaster and café built around one idea: coffee should connect people, not just caffeinate them. As a small business owner raising two young kids, Caleb knows firsthand the discipline it takes to balance entrepreneurship with family life. In this episode of The Prestigious Initiative, Chris and Caleb sit down for a candid conversation about building a purpose-driven brand, cultivating resilience as an entrepreneur, and keeping relationships at the center while navigating the demands of growth. From sourcing and roasting to community-building and parenting, Caleb’s story is equal parts practical wisdom and heart. Whether you’re an entrepreneur, coffee lover, or someone striving to balance ambition with family, this episode will give you both fuel and perspective.
Building a Legacy, Not Just a Business: How Purpose, Persistence, and Connection Fuel Real Success
Every moment tests you. Every action defines you.
That’s the core of what we explore here on The Prestigious Initiative. It’s not about hustle for hustle’s sake; it’s about forging a life and a legacy of impact. And recently, I had a powerful conversation that embodied this very principle.
My guest was my friend, Caleb Benoit, founder of Connect Coffee—a roaster and cafe built not just on quality beans, but on the pillars of community, quality, and genuine connection. Caleb isn't just an entrepreneur; he's a husband and a dad of two young kids, living the daily dance of building a business while building a family.
Our discussion was a raw and insightful blend of entrepreneurship, craftsmanship, and life wisdom. We dug into what it really takes to build a small business rooted in purpose, how to navigate growth without losing your soul, and why the elusive "balance" isn't about perfection—it's about persistence.
The Spark: From Mission Trip to Mission-Driven Business
For many, a business idea starts with a market gap or a personal passion. For Caleb, the spark was profoundly purpose-driven. He shared with me how trips to the Dominican Republic and Haiti for short-term mission work were eye-opening.
"It kind of lit a fire under me," he said in our talk. "I was kind of in this career transition... I want to be able to look back and say that I'm proud of the work that I did and that I did something that benefited other people."
This conviction led him to coffee—a product grown primarily in the developing world and consumed globally. Connect Coffee was born with a built-in give-back program. A portion of every sale funds community development projects in the very regions that produce their beans. As Caleb explained, this creates a tangible connection between your morning cup and the hands that cultivated it, something he feels is often forgotten in our daily ritual.
Faith, Values, and Walking the Line
Naturally, with such a origin story, I had to ask: does this personal faith directly translate into a "Christian business"?
Caleb’s answer was nuanced and reflective, a lesson for any purpose-driven founder. "My ultimate motivation is certainly faith-driven... [But] I don't know that that explicitly flushes itself out in the business," he shared.
He spoke about the challenge of walking that line, choosing to let values like integrity, service, and connection—values you might call Christian—guide the business's actions, rather than making faith an overt marketing tool. "Maybe for us, it's a little more subtle or less overt," he noted, mentioning they serve churches but also a diverse community. It’s a reminder that your core can guide you without needing to be plastered on the window.
Connection: It’s in the Name and In Everything They Do
“Connect” isn’t just a clever name; it’s the operational and spiritual heartbeat of the company. Caleb sees this play out on multiple levels:
In the Cafe: It’s a physical space where friends catch up, deals are made, and students find respite. Coffee is the universal social lubricant.
With Origin: They strive for direct trade relationships, connecting drinkers to the farmers. "We can be connected. We can know some of those folks who are responsible for this thing that we love," Caleb emphasized.
Through Education: They host tastings and classes, because Caleb believes in the power of knowledge. "One of the most gratifying things for me... is to convey some of what I've learned to our customers."
This trifecta turns a transaction into a relationship and a commodity into a story.
The Real Talk: Work-Life "Balance" is a Myth. Try Integration.
As we delved deeper, we hit on a topic every entrepreneur and parent grapples with. I pushed back on the classic term "work-life balance," arguing that for a leader, complete separation is impossible—and perhaps undesirable.
Caleb agreed. "It's not possible to keep work out of home 100% and vice versa... By the strict definition of it, it is impossible, especially as a business owner."
He described the "background processing" that always runs—the part of your brain thinking about business even when you're playing with your kids. The goal isn't to shut it off (those shower ideas can be golden!), but to manage it. His perspective shifted after having children, giving him more empathy and helping realign his priorities in a healthier way.
"It's one of those things where you need to be monitored and managed. Well, yeah, I don't know that I've got it figured out."
This honest admission is where true growth happens. Success here isn't a perfect score; it's persistent, daily negotiation.
Defining Success Beyond the Bottom Line
So, how does a founder like Caleb measure success? The financials have to work, but the true metric is legacy.
"One way to measure success is... what has the business done outside of generating revenue for those who are a part of it?" he said.
He pointed to their give-back model, which during the pandemic expanded to help fund tens of thousands of meals through the Greater Chicago Food Depository. "It's that kind of stuff that I point to and say, 'This is the stuff that is really success.'"
It’s a powerful lesson: build your business to be a vehicle for impact, and the financial success becomes part of a larger, more meaningful story.
The Engine Room: Systems are Your Salvation
When you’re juggling a roastery, a cafe, a family, and community work, chaos is the enemy. Caleb’s antidote? Systems.
"I've learned to think in terms of systems... Everything needs a system, whether it's paying bills or managing inventory or even stuff at home with the kids."
He gave a simple example: a checklist for their mobile espresso cart events. This basic system eliminated pre-event anxiety and ensured consistency. It’s a microcosm of a larger truth: consistency in your product, your service, and your community presence relies on repeatable, systematized processes. It’s the discipline that sets the stage for freedom and growth.
A Standout Quote for Every Entrepreneur
From our conversation, one line from Caleb perfectly encapsulates the entrepreneurial journey, especially for those with a family:
"Balance isn't about perfection. It's about persistence."
Let that sink in. It’s not about getting it right every day. It’s about showing up, every day, and continuing to navigate the beautiful, messy integration of your passions, your responsibilities, and your purpose.
Final Wisdom: Count the Cost
Towards the end of our talk, Caleb shared the advice he gives to eager students: count the cost.
"Entrepreneurship gets romanticized... but it's not all sunshine and rainbows... Not everyone is wired to start their own business."
He doesn’t say this to discourage, but to ground. There is immense upside in being a vital part of a team without carrying the ultimate weight. It’s a sobering, necessary message in a culture obsessed with startup glory.
My Final Thoughts
My conversation with Caleb Benoit was a masterclass in building with purpose. He showed us that:
Purpose is your compass, guiding you from spark to sustainable action.
Connection is your currency, enriching every stakeholder from farmer to customer.
Persistence is your practice, the daily grind that makes balance possible.
Systems are your scaffold, allowing you to build higher without collapsing.
Legacy is your measure, ensuring what you build echoes beyond the balance sheet.
Connect Coffee is more than a cafe; it’s a case study in mindful entrepreneurship. You can find them at ConnectRoasters.com or @ConnectRoasters on social media, and if you’re near Bourbonnais, Illinois, experience the connection firsthand.
Remember, what you build matters. And who you build it for matters more.
Join us weekly for deep, unfiltered conversations about personal development, leadership, productivity, and excellence. Each episode is crafted to help you take initiative and unlock your full potential — both personally and professionally
Ralph Velasco returns to The Prestigious Initiative to share stories and lessons from his new book, Bucket Lists for Travel: Places to Go Before Your Knees Give Out! — a celebration of adventure, aging well, and embracing life while you can. As a travel photographer, entrepreneur, and storyteller, Ralph has spent decades exploring the world and helping others do the same. In this conversation, Chris and Ralph dive into what “mindful travel” really means, why curiosity is the ultimate business skill, and how entrepreneurs can stay passionate while building careers that allow freedom and purpose. With humor, heart, and practical insight, Ralph proves that adventure doesn’t end when your knees start to ache — it evolves. This episode is for anyone ready to explore more — in the world, in their work, and within themselves.
Randall Ian Thames spent 35 years navigating corporate boardrooms—from C-suite to senior roles at the world’s top consulting firms. Now, through his Inspirit Institute and the “Discover–Develop–Display™” framework, Randall helps leaders find their hidden “superpower,” ignite inner purpose, and produce inevitable outcomes in their careers and lives. In this episode of The Prestigious Initiative, Chris and Randall dig into how to build leadership from the inside out, why purpose fuels sustainable progress, and how every leader can rise—not just to the role, but beyond. Expect practical tools, philosophical depth, and stories that will make you rewrite what you thought success looked like.
Made with Bullet