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...
099: "Balancing Intuition and Iteration" (lessons from Chase Damiano)
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🧠Erik’s Take
In this reaction episode, Erik reflects on his conversation with Chase Damiano—COO turned systems thinker, father-first decision maker, and founder of Humans at Scale. What stood out most? Chase doesn’t just talk strategy—he tests it. Erik highlights how Chase treats business like a living lab, combining intention, iteration, and humanity into every decision. This episode zooms in on what it really means to lead with intentionality, how systems thinking plays out in the real world, and why experimentation might be the most underrated leadership muscle of all.
🎯 Top Insights from the Interview
- Treat your business like a laboratory — Chase runs experiments, not assumptions. Every major move, from coffee trikes to national distribution, was a test.
- Systems thinking as a leadership edge — With a background in systems engineering, Chase applied operational rigor to startups and service-based businesses alike.
- Intentionality isn’t just personal—it’s operational — Whether choosing where to live or what to launch, Chase methodically tests alignment with values.
- Values-driven decisions scale — From turning down a promising job to stay close to his son, to shaping his new company, Chase walks the talk.
- Even your best ideas are just hypotheses — From sales scripts to team culture, everything is a test—until feedback proves otherwise.
🧩 The Personal Layer
Erik shares how Chase’s lens of systems + intention got him thinking about his own decisions—especially around parenting, leadership, and product testing. There’s a quiet kind of boldness in how Chase lives: methodical, values-aligned, and open to pivoting. That balance between rigor and flexibility? Erik sees it as an antidote to stuck leadership.
🧰 From Insight to Action
- Ask yourself: “Am I treating this strategy like a test?”
- Revisit your personal or professional goals—are they aligned with your values or inherited assumptions?
- Design small feedback loops for your next big decision. What would it mean to test it before scaling it?
- Consider how empathy + systems thinking can coexist in your leadership style.
- Journal prompt: “Where am I stubborn where I should be curious?”
🗣️ Notable Quotes
“Our businesses are just experiments.”
“The more you can recognize you’re in the middle of a test, the easier it is to treat pushback as feedback.”
“You kind of have to know where you want to go in order to figure out the best path to get there.”
“Intentionality and systems thinking—what a deadly one-two punch.”
“Every interaction—product, sales, culture—it’s all a lab if you’re willing to see it that way.”
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