67. Jerry Colonna: How Ancestral Wisdom & Radical Self-Inquiry Can Transform Your Leadership Journey

67. Jerry Colonna: How Ancestral Wisdom & Radical Self-Inquiry Can Transform Your Leadership Journey

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.

66. Gay Hendricks: The Art of Living and Unlocking Your Zone of Genius

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.

65. Collette Pervette: Lessons on kink, BDSM and power dynamics from a world class dominatrix

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.

64. Loving and Firm - Parenting With a Big Heart and Clear Boundaries (solo cast)

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:   1. Parenting works best for me when I’m embodying both love and firmness at the same time. Big heart, clear spine. 2. Clear boundaries actually help kids relax. When expectations are consistent, they feel safer and more understood. 3. Honoring agreements matters. When kids see that what we say actually happens, trust deepens quickly. 4. Embarrassment isn’t something I try to eliminate. It can be a healthy part of self expression and being seen. 5. I want my kids to know that trying and failing is not a problem, it is how growth actually works. 6. One of my jobs as a parent is helping my kids assign meaning to hard or awkward experiences, so those moments build confidence instead of shame. 7. Kids are constantly forming beliefs about who they are, and our responses play a huge role in shaping that self identity. 8. Creativity requires room for mistakes. If perfection is the goal, expression shuts down. 9. When I parent from loving and firm, things actually get simpler. Fewer power struggles, more clarity, more connection.

Loving and Firm - Parenting With a Big Heart and Clear Boundaries (Solo-Cast)

In this solo episode, I’m sharing a story about embodying the parenting archetype of loving and firm. It’s been one of the most helpful lessons I’ve learned in being a dad that I’ve been able to apply across my life, in how I lead and how I connect with humans. The story starts at my ex-wife Miki’s annual birthday celebration. Our son Hiro had crushed his first comedy set the night before. But night two? That’s where things got interesting. After our buddy Ben Gleib, a professional comedian, killed on stage, Hiro gets up, starts to improvise, and begins talking back to Miki in a way that didn’t feel good in the system. Miki turns to me and says, “Andy, help.” I raised my voice, not to scold, but so Hiro would hear me. Then I offer him two objective choices: continue the routine he worked so hard on, or go off script again and be done. He opts in to doing the rehearsed routine. About 30 seconds later, he goes off script again. So I stand up, take the mic, and walk him out. Here’s the thing. Even though he’s incredibly upset, what he doesn’t do is question me. Because he knows that when I tell him I’m going to do something, I do it. When we make agreements, I honor them 100% of the time. This isn’t about me getting what I want. It’s about Hiro’s nervous system and development. It removes this layer of anxiety where he feels like he needs to second-guess or push me. Then we get into the meaning-making part. I share a vulnerable story about being eight years old, doing long division with my dad. He gave me this surprised look when I couldn’t figure something out, and in that single moment, I developed this limiting belief that I was bad at math. Because I was bad at math, I thought I was stupid. I held that story in many ways until my late twenties. This age of seven to nine is where kids’ abstract thinking is coming online, they are starting to develop their sense of self. So when these charged moments happen, they’re layering in their own meaning about who they are. That’s why I’m so intentional about helping Hiro engineer the meaning he takes from these experiences. The lessons: (1) When we make an agreement, we honor it. And (2) It’s okay to try and mess up. It’s always better to try and mess up than not to try at all. Can we relate to embarrassment not as something to avoid, but as a healthy byproduct of radical self-expression? This story is a living example of how powerful it is to hold the line of loving and firm. It’s not about getting your kids to do what you want, it’s about providing them with a deep reassurance and calm because they know what is.