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I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
I Have Some Questions...
098: "Knowing When to Delegate Vs. When to Develop a Skill" ft. Chase Damiano
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In this episode, Erik sits down with Chase Damiano, former COO of Commonwealth Joe and founder of Human at Scale, for a conversation about structured experimentation, leadership evolution, and building a life—and a business—you actually want. From nitro cold brew to nervous system regulation, this conversation traverses tactical operations, deep self-inquiry, and how we unlock team performance by letting go of control.
👤 About the Guest
Chase Damiano is a leadership strategist, executive coach, and the founder of Human at Scale, an operations consultancy helping accounting firms run better businesses—without the owner being the bottleneck. Formerly the COO of Commonwealth Joe, Chase helped scale the company into the nation's largest provider of nitro cold brew coffee in offices before stepping away to build a life aligned with his values. Today, he helps leaders build organizations that run smoothly, grow intentionally, and free them to work on what matters most.
🧭 Conversation Highlights
- How Chase helped transform a small family coffee roaster into a national cold brew distributor
- The real cost of being a “down-and-in” founder and how Chase broke the cycle
- Why leadership starts with confronting your own discomfort, not fixing others
- Behind the scenes of building Human at Scale and choosing the accounting space
- The pivotal moment Chase realized his “lead by authority” style was stifling growth
- The power of structured experimentation in business—and in life
💡 Key Takeaways
- Leadership bottlenecks aren’t always obvious—but they often show up in your calendar, your team’s hesitation, and your stress levels.
- Experiments beat assumptions. Chase’s journey—from relocating his life to building multiple companies—proves that structured risk can lead to powerful clarity.
- Coaching changes everything. Chase’s transformation began with the humility to ask for help and the right coach to unlock his potential.
- Process matters, but people more so. Scaling responsibly isn’t just about SOPs—it’s about empowering people to own their roles with clarity and context.
- Doing the uncomfortable work is the signal. Whether it’s selling, letting go, or confronting your own patterns, discomfort is often the compass.
❓ Questions That Mattered
- What’s the earliest moment you embraced personal agency and responsibility?
- How do we balance vision-setting with responsiveness to reality?
- How can founders know when to delegate versus when to develop a skill?
- What makes organizational context and alignment more than just job titles?
- How do we avoid “creative avoidance” while still honoring our genius?
🗣️ Notable Quotes
“We are the conscious creators of everything going on in our lives—whether we like it or not.” — Chase
“Most decisions are reversible. That truth frees you to act.” — Chase
“I was unconsciously holding down the potential of the entire organization.” — Chase
“Contextualized alignment—when people really see how they fit—is what unlocks action.” — Erik
“Leadership isn't about talent. It's about helping other people rise in theirs.” — Chase
🔗 Links & Resources