In this raw, honest, and deeply reflective conversation, Kevin Rice sits down with Deborah Palmer Keiser, global operator, supply-chain builder, fear-tamer, and now COO of Pair of Thieves, to explore the cost of ambition, the courage to repair, and the surprising ways our kids teach us to lead. Deborah spent three decades opening markets, fixing broken supply chains, and resurrecting brands across the world, from Gap and Williams-Sonoma to Victoria’s Secret, AllSaints, Boardriders, and Yeezy. She built a reputation as the operator companies call when it’s time to grow up and get serious. But behind the promotions, global travel, and relentless execution was a young daughter quietly taking inventory of all the moments her mom missed. The turning point came when seven-year-old Tilly asked to see the family’s bank balance, not because she cared about money, but because she wanted to know why her mom kept choosing work over her. That one question cracked Deborah open. It sparked a five-year process of repair, reconnection, and relearning how to sit still long enough to paint nails, draw pictures, and rebuild trust one quiet moment at a time. Deborah shares how being fully present with her daughter made her a better leader, more human, more honest, and more clear about her limits. She explains why becoming “truthfully unavailable” actually strengthened her teams, empowered emerging leaders, and deepened commitment across her orgs. And she reflects on what her daughter taught her about emotional articulation, empathy, and creating space for others to be fully themselves. Together, Kevin and Deborah explore what it means to raise a young artist in a world that pushes safe careers, why fearlessness can be both a gift and a trap, and how childhood instability shaped Deborah’s early beliefs about success, security, and motherhood. They talk about global cultures that integrate family into daily life, and what America gets wrong about excellence, work, and worth. This is a conversation about the long road back to connection, the humility of repair, and the kind of leadership that grows not from ambition, but from love. In this episode, you’ll learn: • Why a seven-year-old’s question about money became Deborah’s wake-up call • How to repair a parent–child relationship after years of distance • Why presence, not provision, is the foundation of trust at home • How becoming “unavailable” at work actually made Deborah a stronger leader • What global cultures teach us about integrating family into professional life • How fearlessness can morph into self-isolation and what breaks the cycle • Why dragging people uphill fails and how servant leadership changes everything • How childhood instability shaped Deborah’s early beliefs about success • What it means to raise a young artist in a world obsessed with productivity • Why taking your dream all the way is the antidote to lifelong regret Top Takeaways: • You can provide for your kids and still lose connection with them. Repair requires presence, not perfection. • Kids often tell the truth adults avoid. Listening to them takes courage, but it changes everything. • Leadership rooted in humanity invites teams to step up, not step back. • Your greatest strengths, fearlessness, independence, self-reliance, can become your greatest limits if left unchecked. • The stories we inherit from childhood quietly shape every decision we make as adults. • Openness builds trust. Pretending to “hold it all together” builds distance. • Culture is people. People stay (or leave) because of who you are, not what you produce. • Every path is hard. You might as well choose the one that makes you feel alive. • Taking your dreams seriously is an act of courage and self-respect—and the same is true for your kids. Abou... Chapters (00:00:00) - Introduction and Setting the Scene(00:03:56) - Deborah's Career Journey and Current Focus(00:09:52) - Parenting Insights and Evolving Relationships(00:17:47) - Lessons from Leadership and Work-Life Balance(00:29:27) - Cultural Perspectives on Work and Family(00:31:18) - Cultural Connections and Family Dynamics(00:35:58) - The Impact of Travel on Parenting(00:41:04) - Navigating Parenting and Personal Growth(00:45:45) - Supporting Creative Aspirations
