Leadership Lessons from Judge Frank Caprio: Why Empathy is the Real Power Move
¡Conectemos!
Hello Humans,
Today I want to share a little bit about an amazing human I read about. Some people think leadership is about being the toughest person in the room. Move fast, drive results, push harder than everyone else. But after reading about Judge Frank Caprio's legacy and living through my own journey building 787 Coffee from a single farm to 30+ locations, I've learned something profound: the true mark of leadership isn't in how hard you push, but in how deeply you connect.
Let me share what these two very different worlds—a Providence courtroom and coffee shops, taught me about what it means to lead with your heart.
Two Masterclasses in Human Connection
When I first read about Judge Caprio's show Caught in Providence, I was struck by something that felt familiar. He didn't just hear cases—he heard humans. The single mom choosing between groceries and a parking ticket. The student juggling jobs and dreams. The father rushing his sick son to the doctor.
Watching him, I realized this was exactly what I’ve been creating at 787 Coffee. When I developed what I call the "Infinity Leadership Methodology"—training eight individuals intensively, then having them mentor another eight, creating an expanding network of leaders, I wasn't just building a management structure. I was multiplying human connections.
Both Judge Caprio and I understood something that most leaders miss: you don't scale impact by treating people like numbers. You scale by multiplying human connections.
-Let’s do this.
From One Farm to 30+ Shops: How Connection Built an Empire
When I started 787 Coffee, I had one simple belief: every human who walked through our doors—whether as an employee or customer—deserved to feel seen, valued, and empowered. That wasn't just good ethics; it became our competitive advantage.
My "You Got This" philosophy isn't just a tagline—it's how I approach every leadership decision. Just like Judge Caprio saw potential in people others had written off, I see potential in every barista, every manager, every person who joins our team.
Here's what I learned about scaling culture without losing soul:
Lesson 1: Quality Mentorship Over Mass Management
Early in building 787 Coffee, I made a choice that seemed counterintuitive. Instead of trying to manage every detail across locations, I focused intensively on developing a core group of eight leaders. These weren't just managers—they were people I poured into, teaching them not just coffee operations but emotional intelligence, team-building, and the art of seeing people first.
Judge Caprio didn't rush through cases, and I don't rush through developing leaders. Sustainable growth comes from depth.
Lesson 2: Teach Leaders to Teach
The magic happens when your leaders become developers of other leaders. In my Infinity system, each leader I mentor becomes responsible for mentoring others. This creates what I call a "leadership multiplication effect"—a culture of empowerment and self-reliance that grows exponentially.
When you walk into any of our 30+ locations today, you're not just getting coffee from an employee. You're experiencing the result of a leader who was developed by another leader, who was developed by another leader, tracing back to this core philosophy of human connection.
Lesson 3: Influence Over Control
Trying to control every detail across multiple locations kills culture faster than any external threat. Instead, I focus on influencing through empowerment. Each trained leader brings their unique approach while staying true to our core values.
Judge Caprio didn't control outcomes, he influenced them through compassion. I don't control every coffee shop detail, I influence culture through empowerment.
My Challenge to You
Judge Caprio once said: "I'd rather go overboard with compassion than overboard with punishment."
I've built my entire business proving this philosophy creates empires. Through our leadership network, we've built a resilient organization ready for continued sustainable growth.
So here's my challenge: the next time you're facing a tough leadership decision—pause. Remember Judge Caprio's compassion. Think about what "You Got This" really means for your people. And choose human connection.
Because I've learned that empathy isn't just the greatest power move a leader can make—it's the only move that builds something lasting.
Leadership isn't confined to business. It's a mindset that applies to every part of life. Leaders are those who recognize that things can be better, who can break down complex challenges, and who guide their teams toward solutions with empathy and clarity.
That's not just how I built 787 Coffee. That's how I believe every leader should approach their legacy.
Let's get to work. 💯
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