Ask For An Answer

Jim Fielding
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ASK FOR AN ANSWER is more than a podcast—it’s a practice space for real leadership. Hosted by Jim Fielding, each episode features an honest, unscripted conversation with a leader facing a real challenge: a hard transition, a high-stakes decision, or a moment when the answers aren’t clear. Together, they work through it in real time with clarity, candor, and a growth mindset. This isn’t abstract theory or polished performance. It’s leadership as it actually happens: live, thoughtful, and grounded in shared insight. More than anything, ASK FOR AN ANSWER captures what it sounds like when leaders stop performing and start thinking—when they lower the armor, ask for help, and trust the process. If you believe leadership is a practice, not a pose, this podcast is for you.

  1. 5D AGO

    Leadership, Legacy, and Building an Iconic Brand (with Uncle Nearest CBO Katharine Jerkens) | #8

    What happens when an untold American legacy becomes a modern business movement and a masterclass in leadership, culture, and brand truth? In this episode of Ask for an Answer, Jim Fielding sits down with Katharine “Kate” Jerkens, Chief Business Officer of Uncle Nearest Premium Whiskey, to explore what it takes to build an iconic brand in uncertain times—without hiding behind “having all the answers.” Kate shares the inside story of Uncle Nearest’s rise, including the origin of the Nearest Green legacy (the first known African-American master distiller who taught Jack Daniel), the leadership realities of building distribution and culture in a white, male-dominated industry, and how COVID reshaped consumer behavior, team dynamics, and decision-making. This is a conversation about modern leadership, authentic storytelling, psychological safety, and the kind of long-game thinking that builds trust, not just revenue. In this episode, you’ll learn: The real origin story behind Uncle Nearest and why legacy-driven brands outperform “marketing-first” brandsWhat it’s like to lead as a woman executive in the spirits industry — and how to keep your edge without losing your humanityHow to navigate uncertainty (COVID, shifting consumer trends, cultural change) with curiosity instead of controlWhy psychological safety is the hidden driver of better decisions and stronger teamsA leadership reminder that applies everywhere: you can’t control the world, but you can control how you show up Mentioned in the episode: The Nearest Green story and the mission behind Uncle NearestThe Nearest Green Foundation and education legacyThe “HBCU Cocktail” initiative and HBCU Heroes Follow Katharine Jerkens / Uncle Nearest Instagram: @unclenearest Website: unclenearest.com Follow Jim Fielding / Ask for an Answer Instagram: @jimfielding Website: Podcast: Ask for an Answer If this episode sparked something for you, don’t just agree with it, try it: take one question into your next meeting and see what changes.

    59 min

  2. FEB 19

    The Long Way to Belonging with Gerardo Celasco | #7

    What if success doesn’t arrive all at once, but shows up quietly when you finally stop running from who you are? Actor Gerardo Celasco opens up about growing up between cultures, being “othered” in El Salvador, chasing an acting dream without a safety net, and enduring years of near-misses before landing career-defining roles like The Waterfront. In a deeply personal conversation with host Jim Fielding, Gerardo reflects on marriage, fatherhood, creative identity, and what it really means to stay the course when doubt never fully disappears. In this episode, you’ll hear about: Growing up between countries, cultures, and expectationsThe reality of chasing a creative dream without connectionsRedefining success, masculinity, and belonging at midlife If you’ve ever questioned your path, your timing, or whether it’s “too late,” this conversation is a reminder that your story is still unfolding and you’re exactly where you’re meant to be.

    1h 3m

  3. FEB 12

    Building Teams That Actually Work | #6

    What really happens when leaders stop playing it safe—and start trusting their people? In this live Los Angeles episode, Jim Fielding is joined by former direct reports Launi King, Elizabeth Litten Miller, and Erin Morris to unpack the real story behind building a high-performing team during a period of massive change at 20th Century Fox. From career pivots and creative freedom to empathy-driven leadership, they share what worked, what didn’t, and the lessons that still shape how they lead today. Together, they explore what it takes to create psychologically safe teams, earn trust in uncertain times, and lead humans—not just org charts. Key themes include: Leading with empathy instead of fearBuilding trust during change and uncertaintyRespecting creativity, fandom, and the people behind the work If you’re a leader—or aspiring to be one—this conversation is a powerful reminder that how you lead matters just as much as what you build.

    1h 9m

  4. FEB 5

    The Leadership Most Companies Miss with Matt Marcotte | #5

    What if the real competitive advantage in business isn’t technology, talent, or capital — but belief? In this kickoff episode of the 2026 Leading With Pride Book Club, Jim Fielding sits down with retail and leadership veteran Matt Marcotte to explore the ideas behind his book Built on Belief: Why Cultures of Commitment Are the Competitive Advantage. From Gap and Apple to Tory Burch and Salesforce, Matt shares how decades of leading through reinvention taught him one truth: companies win when their people truly believe in what they’re building. Together, Jim and Matt unpack what it really takes to build cultures where curiosity, trust, and human connection fuel growth — even in the most demanding, tech-driven industries. In this episode, you’ll hear about: Why curiosity beats certainty in great leadershipHow to build a North Star that aligns teams instead of siloing themWhat it takes to create cultures of commitment, not compliance If you’re ready to lead with more purpose, clarity, and courage, this conversation will change how you think about culture — and your role in shaping it. Matt Marcotte 🌐 m2collaborative.com 📘 Built on Belief — available wherever books are sold Jim Fielding 🌐 jimfielding.com Podcast: Ask for an Answer Instagram: jimfieldingnyc LinkedIn: jimfielding

    50 min

  5. JAN 29

    Building Futures Outside the Box with Wadooah Wali | #4

    What happens when curiosity, courage, and otherness collide into a life of impact? In this Los Angeles Sessions episode of Ask For An Answer, Jim Fielding sits down with pioneering media strategist and XR visionary Wadooah Wali for a deeply human conversation about identity, creativity, and carving a non-linear career path. From growing up feeling “othered” in Gainesville, Florida, to riding the front lines of tech, digital media, and immersive storytelling, Wadooah shares how following curiosity rather than titles led her to reshape the future of entertainment. Together, Jim and Wadooah explore what it really means to live authentically in your work, why careers are rarely linear, and how representation and storytelling can quite literally save lives. This episode is a powerful reminder that growth comes from risk, purpose comes from community, and your story matters more than you think. In this episode, you’ll hear about: Embracing “otherness” as a leadership superpowerWhy curiosity and side hustles shape the most meaningful careersThe importance of representation, community, and telling stories that endure If you’ve ever felt different, uncertain, or called toward something bigger, this conversation will remind you that you’re exactly where you’re supposed to be. Connect with Jim Fielding Instagram: @jimfielding LinkedIn: Jim Fielding Connect with Wadooah Wali Website: www.newcanvas.co Instagram / X / LinkedIn: @WadooahWali New Canvas: @newcanvasxr

    56 min

  6. JAN 22

    Inside America’s Real Conversations with Jeremy Hobson | #3

    What happens when a lifelong radio obsessive builds a show that lets everyday Americans talk back to the news? From sneaking off to summer camp and calling into radio stations as a kid to hosting national programs on NPR and launching The Middle, Jeremy Hobson shares how curiosity, storytelling, and Midwestern values shaped a career built on listening. Along the way, he reveals why live, unscripted conversations may be exactly what our fractured media landscape needs right now. In this episode, you’ll hear: Why The Middle is redefining what civil discourse sounds likeHow growing up in a professor’s household shaped Jeremy’s voice and valuesWhat real people across the country are saying about the economy, media, and the future If you believe stories can still bring people together, this conversation will remind you why listening matters more than ever.

    1h 2m

  7. JAN 15

    Why Community Still Matters with Jorge Valencia | #2

    What does it take to protect hope when the world feels increasingly hostile? In this powerful episode of Ask For An Answer, host Jim Fielding sits down with Jorge Valencia, CEO of the Point Foundation and former Executive Director of The Trevor Project, for a deeply personal and timely conversation about LGBTQ+ leadership, resilience, and responsibility. Jorge shares how education, mentorship, and community can quite literally save lives—especially during moments of cultural backlash, political change, and isolation. In this conversation, you’ll hear about: Why scholarships are only the beginning—and community is the real impactHow LGBTQ youth are navigating education, safety, and identity in a post-COVID worldWhat history teaches us about resilience, resistance, and the power of staying visible This episode is a reminder that hope isn’t passive—it’s built through action, mentorship, and showing up for the next generation when they need it most. Learn more, support scholars, or get involved: 👉 https://pointfoundation.org

    55 min

  8. JAN 8

    The Power of Asking for an Answer with Chris Glass | #1

    Some years give us answers — but as Chris Glass reminds us, some years ask questions that transform who we become. In this conversation, Jim Fielding sits down with Chris Glass, Global Director of Diversity, Equity & Inclusion at Soho House, to explore the humanity behind leadership, identity, and personal evolution. From navigating DEI in a shifting global landscape to returning to the U.S. after decades abroad, Chris shares how curiosity, humility, and service shape the way he moves through the world. Together, they unpack the idea of “asking for an answer” — a grounded practice of stepping back, seeking perspective, and letting growth lead. Key Themes: Why leaders don’t need all the answers — and shouldn’t pretend toHow living abroad reshapes identity, belonging, and the idea of “home”The changing DEI landscape and how to lead with agility and humanityTurning challenges into lessons instead of failures Chris’s story is an invitation to slow down, stay curious, and trust that every chapter — even the messy ones — is here to teach us something meaningful. Connect with Chris Glass Instagram: Herrglass Connect with Jim Fielding Instagram: jimfieldingofficial LinkedIn: jimfielding

    52 min
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About

ASK FOR AN ANSWER is more than a podcast—it’s a practice space for real leadership. Hosted by Jim Fielding, each episode features an honest, unscripted conversation with a leader facing a real challenge: a hard transition, a high-stakes decision, or a moment when the answers aren’t clear. Together, they work through it in real time with clarity, candor, and a growth mindset. This isn’t abstract theory or polished performance. It’s leadership as it actually happens: live, thoughtful, and grounded in shared insight. More than anything, ASK FOR AN ANSWER captures what it sounds like when leaders stop performing and start thinking—when they lower the armor, ask for help, and trust the process. If you believe leadership is a practice, not a pose, this podcast is for you.

Information

  • Creator
    Jim Fielding
  • Years Active
    2025 - 2026
  • Episodes
    25
  • Rating
    Clean
  • Copyright
    © 691291
  • Show Website
    Ask For An Answer