When the Young Presidents’ Organization asked me to champion a Father‑Preteen Daughter retreat, I agreed— partly because my own 11‑year‑old, Krupa, still thinks hanging out with Dad is cool. I wanted an experience that let high‑performing CEOs remember what compounds over time: trust, not EBITDA.

It took several months, lots of emails, and more than a few late-evening Zooms to craft a program worthy of 31 families. Devil’s Thumb Ranch—8,000 Colorado acres of pure Rocky‑Mountain oxygen—became our classroom.

I knew we were onto something special. But I underestimated the profound impact it would have—not just on the 31 fathers and daughters who joined us at Devil's Thumb Ranch in Colorado, but on my own understanding of what it means to lead with heart.The year-long planning process taught me that true leadership isn't just about optimizing systems or conquering markets—it's about creating spaces where authentic connection can flourish. Every detail required a different kind of strategic thinking. This wasn't about efficiency; it was about intentionality.

I want to thank Meghna Kothari, Georgia York from YPO for partnering with me closely to making this happen.

The Setting: Devil's Thumb Ranch - Where Magic Happens

Nestled in Colorado's Rocky Mountains, Devil's Thumb Ranch provided the perfect backdrop with its blend of rustic charm and sophisticated comfort. The property's Broad Axe Barn became our central gathering place, while the Timber House served as both welcome reception venue and later as the sanctuary for daughters' hair and makeup sessions.

Each activity was carefully sequenced to deepen connection. We began with daughters introducing their fathers (not the other way around), moved through shared adventures like whitewater rafting and ziplines, and culminated with Hollywood-themed dinners and love letter exchanges under the stars. The progression from structured activities to free-flowing connection was intentional—by the final evening, fathers and daughters weren't following a schedule, they were creating their own moments of authentic relationship.

Redefining Success Through a Father's Eyes

One of the most powerful moments came during our session on "Redefining Success" with Cathy and Todd Adams from Zen Parenting. The revelation was refreshing to learn that true measure of success in parenting is measuring our relationship in moments of presence and understanding.

This has helped me in my business transactions. Success isn't just about building something that outlasts you—it's about being fully present for the people who matter most while you're building it.

The Art of Holding Space

Perhaps the most challenging lesson was learning to "hold space" for my daughter's emotions without immediately jumping into problem-solving mode. As leaders, we're wired to fix, optimize, and execute. But parenting—especially parenting a daughter—requires a different skill set entirely.

The concept of LUFU (Listen Until Fully Understood) became a game-changer. Instead of my typical rapid-fire questioning or 30-second solution delivery, I learned to sit with Krupa's experiences, validate her feelings, and resist the urge to turn every conversation into a teachable moment.

Above the Line vs. Below the Line Leadership

One framework that resonated deeply was the concept of operating "above the line" versus "below the line." Above the line means being open, curious, and eager to learn. Below the line means being closed, defensive, and needing to be right.

In business, I've built my reputation on having the answers, on decisive action, on clear direction. But with Krupa, I discovered that admitting my mistakes and sharing my struggles actually strengthened our bond. When I told her about my own failures and imperfections, she didn't see weakness—she saw authenticity.

The Power of Intentional Connection

The retreat taught me that event management at this level isn't about logistics—it's about emotional architecture. Every transition, every timing decision, every space we chose was designed to facilitate deeper relationships between fathers and daughters. From the icebreaker activities where daughters introduced their fathers, to the shared adventures that created equal vulnerability, to the final love letter exchange under Colorado stars.

Lessons in Vulnerability and Modeling

Cathy Adams’ lesson reminded us that parenting is 60% modeling and 30% the energy with which we deliver our words. Our daughters are watching how we treat other women, how we handle stress, how we respond to conflict. They're learning about relationships not from what we say, but from what we do.

This hit me particularly well when I realized that Krupa has been observing my approach to life and business. While that mindset has served me well professionally, I needed to model a different way of being in our relationship—one that prioritized connection over correction, discussion over discipline.

The Grief of Growth

One of the most profound insights was learning to grieve the loss of who our daughters used to be as they grow into who they're becoming. The little girl who used to hang on my every word is supposed to push away, to take the lead, to challenge my authority. This isn't rebellion—it's healthy development.

Instead of fighting this natural progression, I'm learning to celebrate it. When Krupa takes the lead in choosing our activities or expressing her opinions, I'm practicing stepping back and trusting her judgment. The hierarchy has changed, and that's exactly as it should be.

Creating Asynchronous Connection

In our hyperconnected world, I've discovered the power of asynchronous communication with Krupa. Sometimes the most important conversations happen through Post-it notes on her pillow or shared playlists of her favorite music. These small gestures create a connection without the pressure of immediate response or the risk of her seeing my disappointment in real-time.

Moving Forward: The Ongoing Journey

As I write this, Krupa and I are preparing to join Toastmasters together—another opportunity to learn and grow side by side. The retreat at Devil's Thumb Ranch wasn't a destination; it was a beginning. Every day presents new opportunities to practice these lessons, to choose connection over conquest, to lead with both strength and tenderness.

To my fellow YPO members and leaders reading this: the greatest ROI you'll ever generate isn't measured in quarterly reports. It's measured in the quality of your relationships with the people who matter most. The same strategic thinking that makes us successful in business can create profound transformation in our roles as fathers—if we're willing to expand our definition of what success actually means.

True legacy isn't just about building systems that outlive you—it's about modeling the kind of human being you want your children to become.

The year of planning was challenging, yes. But the lifetime of deeper connection with my daughter? That's the kind of return on investment that truly matters.

This retreat was made possible through the incredible support of YPO and the expertise of Cathy and Todd Adams from Zen Parenting. To the 30 other fathers who joined me on this journey: thank you for your vulnerability, your commitment, and your willingness to grow alongside your daughters

How Championing the YPO Father-Daughter Retreat Helped My Understanding of Compassionate Leadership