Today's guest is Jerry Colonna, a leading executive coach who is also the co-founder and CEO of Reboot, the executive coaching and leadership development company, host of the Reboot Podcast, and author of REUNION: Leadership and the Longing to Belong and Reboot: Leadership and the Art of Growing Up.

Drawing on his wide variety of experiences, including his years as a partner with JPMorgan Partners and co-launching Flatiron Partners with Fred Wilson, Jerry shares how he helps clients design a more conscious life and make the changes needed to improve their performance and satisfaction. He explores how our willingness to look honestly at ourselves directly shapes our capacity to lead, to help others, and to be truly present.

Jerry reveals his approach to presence and self-trust, emphasizing that the deepest coaching (and leadership) doesn't come from mastering techniques or performative frameworks. It emerges when we drop the tactics entirely and lean into being fully with another person. He outlines how our unresolved "demons," if left unprocessed, get projected onto the people we lead and coach, and why anyone in a position of power carries a moral responsibility to do their own inner work first. Through candid stories, from his years in psychoanalysis to a vision quest that gave him the name "Holder of Stories of the Heart," Jerry shares his core belief that better humans make better leaders, and that self-inquiry and business results are not in opposition but must be pursued together.

Whether discussing the "hungry ghosts" left behind by disconnected ancestry, the difference between niceness and true kindness, or his own struggle with a harsh internal critic even at 63, Jerry offers a refreshing perspective on leadership that prioritizes authenticity and kinship over ego, control, and "dirty fuel" like fear of failure. The conversation culminates in a powerful reframe: rather than asking "who should I model myself after," the real work is asking who you choose to become, taking in wisdom from your elders while refusing to outsource your own identity to anyone else.

Lessons from the man who named our self-sabotage, on love, genius, and waking up.

Whether it's a marriage of 47 years or a single afternoon in an office, the biggest leaps in our lives often follow the smallest moments of awareness…

Gay Hendricks has spent more than 40 years as a leading voice in relationship transformation and body-mind therapies. With his wife, Dr. Kathlyn Hendricks, he's authored bestsellers including Conscious Loving, The Big Leap, and the recently released Your Big Leap Year. He's coached more than 800 executives at companies like Dell and Hewlett-Packard, and he calls himself, simply, "a cheerleader for wonder."

What he shared about upper limits, genius, and the art of living was deeply moving.

If you've ever wondered why things tend to fall apart right after they start going well, this conversation will serve as a well-rounded introduction.

Here are some of my favorite themes that we explored…

The universe teaches you with a feather first. The sledgehammer is optional.

Gay explained that life is constantly trying to teach us, gently, at first. If we're open and paying attention, the lesson arrives as a feather tickle. If we're closed off and defensive, it escalates until we can't ignore it anymore.

"If we're wide open to learning, we don't get sledgehammers, we get feather tickles."

The lesson doesn't change. Only the volume does. Whatever you're avoiding right now is getting louder, not going away.

Feeling good for too long is its own kind of threat.

Gay told me about the day he discovered what he calls the Upper Limit Problem. He'd just had an exhilarating lunch talking research with a colleague, dropped his six-year-old daughter at sleepaway camp that morning, and was sitting in his office feeling fantastic, when he suddenly became convinced she was lonely and miserable. He called the camp in a panic. The director told him she was outside happily playing soccer, and gently asked if it might be him, not his daughter, who was struggling with the separation.

That single moment cracked something open. We don't just resist pain. We resist too much good feeling, too, and we'll quietly manufacture a crisis just to bring ourselves back down to a level we believe we deserve.

Your genius zone isn't about being the best. It's about being unmistakably you.

Gay described four zones we all operate in: incompetence, competence, excellence, and genius. Most people get stuck in excellence, good enough to get promoted, praised, paid, but it's never quite enough, because excellence has no ceiling on what it demands of you. Genius is different. It's not about being better than everyone else; it's about doing the thing only you do, in the way only you do it.

"What gets you to life fulfillment is spending time in your genius zone, which is where you're doing things that you really love to do and that you're extremely good at."

That distinction matters everywhere leadership, relationships, the way we spend our days. Competence and excellence will keep you employed. Only genius will keep you alive.

Whether it is the boardroom, or the bedroom…the most transformative lessons can come from the most unexpected places…

Colette Pervette has spent over two decades as a professional dominatrix and educator. She holds a PhD in education and her students call her an educatrix. What she shared about power, presence, and pleasure were deeply insightful.

If you’ve ever wanted to go deeper on bdsm, kink and power dynamics in general; this conversation will serve as a well-rounded introduction.

Here are some of my favorite themes that we explored…

The dom is subconscious. The sub is self-conscious.

Colette was explaining what it actually takes to hold the dominant role — and it has nothing to do with aggression or performance. It requires the complete removal of your own ego. The moment a dom becomes self-conscious, she explained, they've already lost the role. Their full awareness has to be on the other person.

"If for a moment you're self-conscious, you've lost the role, because you're supposed to be conscious of the sub."

Shame is where your power is hiding.

Colette described how her clients often arrive holding desires they are deeply ashamed of — things they've never said out loud. And the act of bringing those things into the open, of having them held without judgment, is often the most cathartic experience of their lives. The shame doesn't survive contact with expression.

Whatever truth you're not saying — it's costing you more than you think.

Power is trust, not force.

The most effective doms, Colette told me, aren't the most aggressive. They're the ones who have built the deepest trust — so completely that someone willingly surrenders their autonomy, confident their wellbeing is in good hands.

That's applicable to all forms of leadership. Authority without trust is coercion. Leadership without trust is just management. The room only follows you when they genuinely believe you're accountable to something larger than your own ego.

The most truly successful people I've ever worked with don't hold power through force. They hold it because people trust them — trust that they are seen, considered, and taken care of.

In this solo cast, I explore parenting through the archetype of being loving and firm, what it actually looks like to lead with a big heart while holding clear boundaries. I share a personal story about my son Hiro and a comedy routine he was working on, and how that moment became an unexpected lesson in restraint, trust, and leadership as a parent.

I talk about why allowing our kids to feel embarrassment is not something to protect them from, but something to honor as a natural part of self expression, creativity, and growth. We look at how rescuing too quickly can unintentionally undermine confidence, and how holding loving boundaries helps children build resilience and self trust.

I also reflect on the importance of honoring agreements in the parent child dynamic, and how consistency, clarity, and warmth work together to create safety. This episode is an invitation to practice parenting that is deeply compassionate and deeply grounded, without collapsing into permissiveness or control.

Key takeaways in the episode:

I didn’t bring Mastin Kipp on the show because Oprah called him a “thought leader for the next generation.” I brought him on because, when I reconnected with his work after years apart from it, I felt a new groundedness, a shift from motivational self-help and personal transformation, to something deeper…talking about the body, the nervous system, and real emotional wellbeing.

We start by diving into Mastin’s journey, from managing platinum-selling rock bands to pioneering Functional Life Coaching, and a series of synchronistic awakenings. His story is a reminder that no matter how much you achieve, if your system isn’t safe, you’ll keep crashing into the same wall.

There was one central teaching that will be especially valuable to those on the growth path: It’s not about being calm all the time. The real gift is how fast you return to baseline after life knocks you sideways.

If you’re craving real change, in leadership, love, business, or your inner world, this episode will interest you. We cover science, somatics, the “dirty fuel” of entrepreneurship, and the art of spotting your hidden trauma by noticing the thing you complain about most.

What if the “long game” of leadership isn’t about knowing the perfect playbook or chasing the next quick fix, but about the discipline to choose, practice, and recommit, week after week, for years on end? What if the most profound growth you’ll ever experience as a founder or leader is not a moment of sudden insight, but the slow compounding of self-awareness, responsibility, and everyday choices over decades?

This episode of What’s the Big Idea features Rand Stagen, seasoned entrepreneur, founding member and former board chair of the Conscious Leadership community, and for more than twenty-five years, the driving force behind the Stagen Leadership Academy.

Widely known for his insistence that culture and leadership can’t be separated, and for helping organizations play the “infinite game,” Rand brings decades of experience in guiding high-performing teams, family businesses, and visionary founders beyond short-term tactics to something deeper, stickier, and far more meaningful.

Andrew sets the stage for an organic, candid conversation that cuts to the core of what makes responsible leadership both liberating and daunting. The two dive into Rand’s own journey, from a clueless 23-year-old publisher thrown into the fire, to a leader deeply shaped by years of coaching and reflection, and unpack the difference between traditional training (short, episodic, skill-based) and the kind of long-term development that actually transforms capacity, character, and results.

Inside this episode, Rand lays out foundational frameworks and practices, delivered with humility, hard-won stories, and a deep respect for paradox. He challenges Fortune 50 CEOs (and every ambitious founder) to grapple with the tension between short-term fires and the decades-long arc of impact, revealing why the real work isn’t about saying “yes” to every shiny opportunity but about developing the discernment to say “yes” to your deepest priorities, over and over.

You’ll walk away with practical insights, including:

Why does this conversation matter right now? Because in a noisy, high-velocity world, the leaders who thrive aren’t the ones with the fastest answers, but with the deepest roots, the ones who can steward themselves and their teams through both turbulence and triumph, with clarity, humility, and rigor. For founders, CEOs, or anyone aspiring to lead with more relational integrity and long-term impact, this episode is a compass for building not just better organizations, but better humans.

Settle in for a wise, grounded, and refreshingly candid conversation. Let Rand and Andrew remind you: transformation isn’t a sprint; it’s a compounding journey of daily responsibility. Listen in, and remember, what you practice today becomes who you (and your company) will be in ten, twenty, even fifty years.

After climbing the “success mountain” of Princeton, Forbes 30 Under 30, a successful exit to SalesForce, Scott found himself cracked open by a spiritual awakening that forced him to build a bridge between rapid inner growth and a life of high achievement. Today, that bridge looks like writing, a vibrant online community, and honest conversations about integrating self-realization with contribution, prosperity, and adventure.

When I was a lost 21-year-old with no idea what I wanted to do with my life, service saved me. I didn’t know where to find fulfillment or a sustainable, financially viable career, but I remembered the joy of supporting young people with disabilities to play sports in college. My dad said simply, “Why don’t you just do more of that?” With nothing else to hang on to, I took his advice and started my first nonprofit, Dreams for Kids DC.

Running that organization, I realized that marginalized communities—like folks with disabilities—are often only seen as recipients of service, not as people who can give. We evolved our programs so that the kids we served also had opportunities to serve others, showing them they were capable of contribution.

For me, service has always been one of the most direct pathways to purpose. That’s why I’m so excited to have Dan Doty on the podcast today. Dan is a founder of Everyman, one of the men’s work facilitators I respect most in the world, and an excellent father, husband, and deeply good man who genuinely cares about people. He’s in it for the right reasons.

After helping bring on the second wave of men’s work with Everyman, Dan has launched a new initiative called Manpower, which brings men together around community-driven service projects nationwide. I felt so aligned with his mission that I joined as an inaugural board member to help in a small way.

This conversation dives into men’s work, the loneliness epidemic, and the power of finding purpose through giving back.

Here’s what you’ll take away:

Why listen, and why now? Because the loneliness and confusion facing so many men isn’t just abstract, it’s showing up in rising suicide rates, isolation, and a hunger for leadership that actually serves. For founders, leaders, and anyone working on themselves, this episode is a reminder: fulfillment, and real growth, don't happen in isolation. The real medicine might just be found, together, in the service of others.

Tune in for a wise, grounded, and deeply hopeful conversation. Let Dan and Andrew remind you: it’s not just about “doing the work,” it’s about getting to work, side by side, building the world (and the selves) we most want to see.

Listen in. The next big idea may start right down the block, with a pair of gloves and a group of guys, ready to serve.

What if business could be as human, and as messy, as life itself? What if being an ethical leader wasn’t about hitting some mythical state of perfection, but rather about showing up, getting a little lost, and finding your values again and again along the way?

On this episode of What’s the Big Idea, Andrew sits down with David Gelles, New York Times reporter, bestselling author, and one of the most thoughtful chroniclers of modern leadership and capitalism. If you’ve grappled with questions about doing “good business” or wondered whether it’s really possible to put planet and people on equal footing with profit, David’s the guy you want in your corner. His latest book, Dirtbag Billionaire, tells the wild and often contradictory story of Yvon Chouinard, founder of Patagonia, who not only built a world-class company on his own weird, gritty values, but ultimately gave the whole thing away.

This episode goes way deeper than another pat case study in “purpose-driven business.” Andrew and David push into the real questions: What does it actually look like to build a values-driven company while wrestling with your own imperfections? Can you succeed in capitalism without losing your integrity? And why is holding steady to your purpose so hard, and so necessary, right now?

Here’s what you’ll take away:

Why does this matter? Because for founders, leaders, and anyone wanting to build something that endures and honors their deepest values, the path is rarely black-and-white. In a time when corporate activism, mission-washing, and burnout all mix together, it’s deeply heartening, and genuinely useful, to see that “doing it right” is mostly about staying present to your own messiness, learning as you go, and never mistaking profit for purpose.

If you want frameworks, real stories, and the unvarnished truth about leading with integrity in modern business, you’ll find all that and more here.

Listen in for a conversation that’s thoughtful, honest, and rooted in the idea that being an ethical leader is less about being a saint and more about coming back, again and again, to what matters most.

How do we turn love and intimacy into a living practice, one that transforms how we lead, connect, and show up in our romantic relationships?

On this episode of What’s the Big Idea, Andrew sits down with John Wineland, celebrated teacher, author, and guide to all things relationship, intimacy, and embodied masculine leadership. John is known for his transformative workshops and years of study with David Deida, as well as for helping thousands of people move past cliché ideas about intimacy toward something much deeper, kinder, and truly life-changing.

If you are curious about sacred intimacy, tantra, or what it means to lead from the heart, John brings these sometimes mystified topics down to earth. He clarifies that sacred intimacy isn’t a fixed state , but the practice of allowing the divine - love, consciousness, presence, to flow through your relationships. Drawing on stories from his own journey and decades working with men, women, and couples, John shares a toolkit for both cultivating connection and facing its challenges.

Here’s what you’ll take away from this conversation:

The Four Pillars of Sacred Intimacy: John introduces the central framework that has guided his work: intimacy (our shared humanity), devotion to the field of love, sexual polarity (understanding and honoring difference), and the commitment to deep personal work. Each is a cornerstone, and together they become the supports for a relationship not just to survive, but to thrive.

Making Love Safe and Alive with Ritual and Repair: Learn how simple weekly rituals like “temple nights” or structured praise sessions can shift a partnership from transactional to transformational. The episode outlines approaches for regular check-ins and explains why honest repair work is foundational to trust and emotional safety.

Nervous System Mastery for Modern Life: For men in particular, John goes deep on the value of cultivating embodied presence, emotional regulation, and clear intention. These are the building blocks not only of romantic connection, but also of authentic leadership and executive presence. You’ll hear concrete practices around structure, breath, and nervous system co-regulation.

Practical Intimacy Habits Anyone Can Try: From co-breathing with your partner, to establishing rituals of praise and play, to crisp strategies for moving through the storms of conflict, John offers tools that you can start using today.

Why does this matter now? In an era of chronic busyness, digital distraction, and surface-level connection, our ability to create depth and safety in our most important relationships is a fundamental skill.

Listen in for a conversation that’s both wise and immediately useful, blending frameworks, real stories, and the kind of honest reminders we all need.