Ask For An Answer

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 midlifeIf 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.

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 workIf 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.

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 complianceIf 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 soldJim Fielding🌐 jimfielding.comPodcast: Ask for an AnswerInstagram: jimfieldingnycLinkedIn: jimfielding

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 endureIf 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 FieldingInstagram: @jimfieldingLinkedIn: Jim FieldingConnect with Wadooah WaliWebsite: www.newcanvas.coInstagram / X / LinkedIn: @WadooahWaliNew Canvas: @newcanvasxr

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 futureIf you believe stories can still bring people together, this conversation will remind you why listening matters more than ever.

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 visibleThis 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

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 failuresChris’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 GlassInstagram: HerrglassConnect with Jim FieldingInstagram: jimfieldingofficialLinkedIn: jimfielding

It's the one thing on everybody's mind:A.I.Is it here to help? To destroy? With so many opinions and so much complexity, it can be hard to understand where this technology is going and what it actually does to help.Jim is joined this week by AI pioneer Scott Clendaniel to discuss this topic and better understand the opportunity it presents, and the drawbacks it may bring.Episode Highlights:0:00 - Intro0:34 - Episode beginning1:11 - Meet Scott Clendaniel5:52 - Scott’s journey, AI’s history14:47 - Generative AI’s future19:07 - Microsoft Co-Pilot and the problem it reveals24:58 - Should we be afraid?30:48 - The “return to office” push + AI34:30 - Anyone can use AI40:13 - Different tools and the problem w/ software50:31 - Scott's wisdom-drop53:31 - Episode wrap-upCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH SCOTT CLENDANIELLinkedIn: https://www.linkedin.com/in/tscottclendaniel/

Jim sits down with Brent Ridge (Beekman 1802 co-founder and author of Goat Wisdom) for a heart-forward chat about building a legacy brand, leading with kindness, and turning real community into real company culture. They get into the Beekman origin story (yes, the goats), why “kindness” became the brand’s north star, and practical lessons on partnerships, hiring, and storytelling in a three-second world.Episode Highlights:0:00 - Welcome and introduction to Brent3:25 - Why the book, why now?8:35 - Have you ever felt like you “arrived”?12:41 - Kindness, building brand14:41 - Brent’s first big order19:50 - What the firm (and product) has grown into now23:36 - Disney, company culture28:10 - Culture and attention in the era of social media36:19 - “Two heads are better than one”40:36 - 51% rule47:28 - Need for nature53:06 - Empathy54:13 - “What would you tell 25-year old Brent?”55:42 - Episode wrap-upCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH BRENT RIDGEWebsite: https://beekman1802.com/LinkedIn: https://www.linkedin.com/in/brent-ridge-md-0641791/

This week's episode features a trip down memory lane!Jim returns to Indiana University to sit down with student Joey Mora live and in front of the next generation of retail and fashion to discuss his journey, but more importantly: his success in the retail industry - how he got involved, and what informed him along the way that he was in the right place.Jim also dives into the specifics of his early career, including trips to Japan, living with a Danish family, and his big jump into the upper echelons of corporate leadership - and his newest chapter.Episode Highlights:(0:00) - Intro(0:37) - Episode beginning(2:31) - Meet Joey(5:45) - Getting into retail(12:32) - Travelling, fashion, where it takes you(16:20) - More on Joey and her work on campus(22:01) - This semester for Joey(32:54) - Advice you give to students starting their careers(39:44) - Staying true to yourself(55:49) - Wrap-upCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/

This week, on Jim Fielding and Friends, Jim is joined by Oana Leonte, the Founder & Editor-in-Chief at unmtchd. Her company is a media platform decoding the business of brand and translating cultural insight into systems that scale.Oana sits down with Jim to discuss the path less travelled: Leaving corporate (and your job + safety net).The reason? To achieve a balance in life that few get. The synchronicity between what you're doing, what you're good at, and what you like. Episode Highlights:0:00 – Welcome and introduction to Oana2:56 – How Jim and Oana met7:23 – Diving into “the journey”8:04 – Building your own brand10:12 – From “different” to Unmatched positioning13:22 – Hardest part of the transition16:48 – “Disney deprogramming” & imposter syndrome24:15 – Growing up (fast) as an entrepreneur26:39 – Multi-hyphenate authenticity vs titles35:03 – Biggest surprise of year one36:30 – Rediscovering self before strategy42:13 – Bad Bunny case study: roots → global demand51:30 – Wrapping up + contact Juana52:17 – Mic-drop advice: be faithful to your unmatched essence55:02 – Gratitude & sign-off57:11 – Outro + subscribe/reminderCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH OANA LEONTEWebsite: https://theunmtchd.com/LinkedIn: https://www.linkedin.com/in/oana-leonte

Blake Collazzo is a PR operations and culture lead, community connector, and longtime collaborator on Jim’s book, brand, and podcast. Jim and Blake trace the genesis of their collaboration and their first intro via Joanne Martino, unpack a wild personal-assistant story that ended at a Ramada, talk vitality vs. stagnation, and get candid about coming out, “inviting in,” and showing up for the LGBTQ+ community. They also cover a practical mindset that can do wonders for your day to day experience..Episode Highlights:0:00 - Welcome and introduction to Blake2:32 - From book launch to brand and podcast6:10 - Vitality over stagnation and lessons from Jim’s dad8:32 - The 1% assistant story and the Ramada pivot14:17 - The 2015 epiphany and 2016 move to LA18:23 - Coming out at 19 and “inviting in”27:40 - Representation, safe spaces, authentic leadership28:11 - Control the controllable, leave space for the possibleCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH BLAKE COLLAZOLinkedIn: https://www.linkedin.com/in/blakecollazo/

Brian Tran is a multi-hyphenate founder, designer, and community builder whose journey runs from Houston to Pandora, Kleiner Perkins, and an eight-year startup ride focused on LGBTQ+ connection. Jim and Brian unpack coming out at 13, landing a first VC check in 15 minutes, surviving pivots (including web3), the painful decision to shut down—and the hopeful next chapter: SE / “sector,” a platform creating intergenerational connections for LGBTQ+ industry leaders.Episode Highlights:0:00 - Introduction0:36 - Meet Brian Tran—founder, designer, connector2:20 - Houston roots & coming out at 136:36 - Why he builds LGBTQ+ community products7:05 - How Jim & Brian met; authenticity, connection, community9:13 - College pivots: journalism → film theory → entrepreneurship14:26 - First roles: Pandora product design → Kleiner Perkins (VC)16:50 - What VC taught him (scale, stakes, networks)18:20 - Side app to funded venture19:52 - The 15-minute pitch that landed the first check21:29 - Angel investing 101: what investors really back24:10 - Eight years of pivots30:13 - Why the web3 chapter was the toughest31:54 - 2025 return to hospitality; real-estate hurdles33:34 - Building a membership without a space; sponsor headwinds; shutdown35:08 - Founder reality: failure, resilience, learning39:03 - The next chapter: SE/“sector” for LGBTQ+ leaders41:57 - Mentorship as a two-way street44:02 - Closing & where to find BrianCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/

Dr. Jon Paul is fighting “the good fight” – which is even more important now, more than ever.Dr. Paul’s new book, “Black. Fat. Femme: Revealing the Power of Visibly Queer Voices (in Media) and Learning to Love Yourself” is a guide to standing at the intersection of multiple identities, communities, and causes shapes people and how they see the world.Jim sits down with Dr. Jon to explore his journey in creating this book, the influences he sought and most importantly: his lived experience which informed the book.Episode Highlights:0:00 - Introduction1:20 - The Dr. Jon Paul story7:58 - What has surprised you the most?12:30 - Influences in the book and on Jon18:56 - Sometimes you need to say what needs to be said29:11 - RuPaul’s Drag Race44:19 - Final thoughtsCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH DR. JON PAULWebsite: https://www.doctorjonpaul.com/LinkedIn: https://www.instagram.com/doctorjonpaul/?hl=en

In this special episode of Jim Fielding and Friends, Jim is joined by a close friend – Chris Glass!Chris is the Global Director of Diversity, Equity and Inclusion at Soho House & Co and is responsible for lead strategy and execution of DEI initiatives across the company's +40 Houses and +100K members.Chris joins Jim to catch-up and discuss recent events and how a changing political environment challenges him in both his career and in his life.On a lighter note, Chris shares his unique experience of being an ex-pat living in Germany and what he found in Europe that he couldn’t state-side.Lastly, there are the gold nuggets, the insights that only years of doing it ‘right’ (and wrong) can inform. Jim and Chris explore why you should live life in ‘1 year terms’, the importance of finding what works for you and why designing your life to your exact standards SHOULD be the standard, not the dream.Episode Highlights:0:00 - Introduction0:38 - Episode beginning3:13 - What Chris does4:18 - Commitment to DEI in 20257:38 - “Do you feel pushback in your job?”9:26 - How Chris’ job has changed13:45 - Living and working abroad as an American16:22 - Chris’ “moment”19:13 - Thinking about your life in ‘1 year terms’24:40 - “There is no one way for everyone”30:27 - What locations are left on Chris’ bucket list?36:26 - What does Chris see for the next year?44:40 - Episode wrap-upCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH CHRIS GLASSLinkedIn: https://www.linkedin.com/in/chris-glass-29295/Instagram: https://www.instagram.com/herrglass/

In this special episode of Jim Fielding and Friends, Jim is joined by fellow author Bruce Brackett!Bruce W. Brackett is a social media personality, author, entrepreneur, self-taught visual artist, and international motivational speaker. His book, “How to Breathe While Suffocating: A Story Of Overcoming Addiction, Recovering From Trauma and Healing My Soul” published by Wiley is now available everywhere books are sold.Bruce sits down with Jim to discuss his new book and explore what he is looking to achieve with his story. They also dive into the experiences within the book and how Bruce began his journey in sobriety and more broadly, his journey to helping others in similar situations.Additionally, they discuss the mechanical experience of writing a book (and the challenges therein), how Bruce got the idea (and got started) and most importantly: the biggest lessons from the book and why you should read it.Episode Highlights:0:00 - Introduction0:39 - Episode beginning, intro to Bruce Brackett4:27 - More about Bruce10:24 - “Did you always plan on writing a book?”13:37 - How long it took Bruce to write the book25:20 - “Did you see yourself becoming an author?”30:22 - [After the book release] “What’s been the biggest surprise?”41:43 - Biggest lessons from the book48:06 - Closing thoughts and where you can find BruceCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH BRUCE BRACKETTWebsite: https://www.bwbart.com/Instagram: BWB.PositivityX: BWB.Positivity

In this special episode of Jim Fielding and Friends, Jim reconnects with one of his closest friends of over 40 years, Paul Caine, President of Endeavor’s IMG Events and On Location. What starts as a walk down memory lane quickly becomes a masterclass in leadership, entrepreneurship, and the power of relationships.Paul shares what it’s really like to run some of the world’s biggest events, from the Olympics and Super Bowl to exclusive music festivals and global culinary showcases. As the driving force behind On Location, he offers a behind-the-scenes look at how they create once-in-a-lifetime experiences for fans and brands alike.Jim and Paul also reflect on their college days at Indiana University, where they co-founded a fraternity that would shape their leadership styles and values for decades to come. It’s a full-circle moment filled with laughter, perspective, and a few lessons learned along the way.Episode Highlights:0:00 - Introduction1:12 - How Paul and Jim met2:41 - More about Paul6:01 - What made Paul want to start his own fraternity16:28 - What Paul is doing now24:48 - Paul’s foundation28:47 - Talking “On Location”42:26 - “I’m driven by time”45:55 - Paul’s one big piece of advice and closing thoughtsCONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH PAUL CAINELinkedIn: https://www.linkedin.com/in/pcaine/Foundation Website: https://griffincaresfoundation.org/On Location: https://onlocationexp.com/

This week, Jim sits down with legendary executive Mindy Grossman, Partner at The Consello Group and former CEO of WW (formerly Weight Watchers), to talk about what it really means to lead with purpose.Mindy shares the bold decisions that defined her career, from walking away from law school to diving headfirst into the fashion industry in New York City, and how trusting her gut led her to helm some of the world’s most iconic brands.In this episode, Jim and Mindy dive into why modern leadership requires vulnerability and empathy, the current state of retail, (really) building culture and more!This conversation is part masterclass, part motivational playbook  and a rare look into the mindset of a true visionary.Episode Highlights:0:00 - Introduction2:13 - Meet Mindy9:03 - Two important things (for young people)10:24 - Risk taking12:11 - Mindy’s favorite role19:32 - Culture22:10 - The “Barbeque Effect”25:27 - “Talking up” to the customer35:05 - How does Mindy describe herself?39:07 - Today’s marketplace: What are you saying to clients?42:12 - Mindy’s mantra45:15 - Episode wrap-upABOUT JIM FIELDINGJim Fielding began his career on the department store floor, where he discovered a deep passion for face-to-face interaction and customer experience. That early spark launched a career spanning over 30 years in senior executive roles at some of the world’s most iconic retail and media brands, including Gap, Disney Stores, Claire’s, DreamWorks, and 20th Century Fox. Throughout his leadership journey, Jim became widely recognized for his commitment to developing talent and building inclusive, people-first cultures—believing that individuals perform at their best when they can bring their whole, authentic selves to work.Today, Jim’s full-time focus is on sharing the lessons he’s learned. Through speaking engagements, coaching, writing, advocacy, and community building, he inspires leaders and organizations to create spaces where everyone feels safe, supported, and empowered to thrive.CONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH MINDY GROSSMANLinkedIn: https://www.linkedin.com/in/mindy-grossman/Website: https://consello.com/

What if retail wasn’t a fallback plan, but a power move?This week, Jim is joined by Ron Thurston, bestselling author, keynote speaker, and fierce advocate for the people who keep retail running.In this episode, Ron’s not just talking shop. He’s reframing the conversation entirely as they dive deep into the real value of retail work and why it deserves more respect, more pride, and a brighter future in the age of A.I.From stocking shelves to leading global brands like Gap and Apple, Ron has seen it all. His newest book, Human Pride, builds on that lived experience and delivers a bold message: Your career doesn’t have to be linear to be meaningful. And your skills are more powerful than you think.Whether you’re just starting out or decades in, this conversation is a celebration of work that’s often overlooked but never irrelevant.Episode Highlights:0:00 - Introduction1:54 - “How do we know each other?”4:06 - Ron talks his book and what “pride” means to him12:51 - Talking about “Human Pride”20:46 - Jobs and A.I.29:52 - Careers in retail31:03 - “Retail is detail”, GAP’s renaissance33:30 - Transferable skills (and how to market them)36:31 - Don’t be afraid of new tech40:09 - Stores reflecting consumers40:33 - Episode wrap-upABOUT JIM FIELDINGJim Fielding began his career on the department store floor, where he discovered a deep passion for face-to-face interaction and customer experience. That early spark launched a career spanning over 30 years in senior executive roles at some of the world’s most iconic retail and media brands, including Gap, Disney Stores, Claire’s, DreamWorks, and 20th Century Fox. Throughout his leadership journey, Jim became widely recognized for his commitment to developing talent and building inclusive, people-first cultures—believing that individuals perform at their best when they can bring their whole, authentic selves to work.Today, Jim’s full-time focus is on sharing the lessons he’s learned. Through speaking engagements, coaching, writing, advocacy, and community building, he inspires leaders and organizations to create spaces where everyone feels safe, supported, and empowered to thrive.CONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/CONNECT WITH RON THURSTONLinkedIn: https://www.linkedin.com/in/rthurston/Check out Ron’s Book: https://www.amazon.com/Retail-Pride-Celebrating-Accidental-Career/dp/1544515928

What happens when a kid from Philadelphia’s inner city, armed with nothing but ambition and a guitar, transforms into a Grammy‑nominated songwriter behind P!nk’s anthems and Beyoncé’s ballads? Billy Mann knows.Welcome back to Jim Fielding and Friends!This week, Jim is joined by Billy, a music industry heavyweight whose name you may not know, but whose work you've certainly heard.Billy’s journey isn’t just about hits or fame it’s a roadmap of resilience, reinvention, and real-world pursuit of purpose. Whether you’re an aspiring creator or simply curious about success, this conversation goes beyond the spotlight into the roots of creativity.Episode Highlights:0:00 - Introduction1:45 - Intro to Billy Mann8:05 - “What was the first hit?”10:56 - Working with others, or solo?12:15 - “How do you describe yourself?”13:57 - Which song represents you best?18:30 - Billy’s favorite collaborators 20:38 - Writing with Grayson Chance, “Brown Paper Bag”26:58 - Getting what you want out of life, fulfillment34:46 - Comparmentalization (for better or worse)42:22 - Using survivor’s guilt44:25 - Being tribalized46:24 - Billy’s “Golden Mantra”50:08 - Billy talks Chosen FamilyABOUT JIM FIELDINGJim Fielding began his career on the department store floor, where he discovered a deep passion for face-to-face interaction and customer experience. That early spark launched a career spanning over 30 years in senior executive roles at some of the world’s most iconic retail and media brands, including Gap, Disney Stores, Claire’s, DreamWorks, and 20th Century Fox. Throughout his leadership journey, Jim became widely recognized for his commitment to developing talent and building inclusive, people-first cultures—believing that individuals perform at their best when they can bring their whole, authentic selves to work.Today, Jim’s full-time focus is on sharing the lessons he’s learned. Through speaking engagements, coaching, writing, advocacy, and community building, he inspires leaders and organizations to create spaces where everyone feels safe, supported, and empowered to thrive.CONNECT WITH JIM FIELDINGLinkedIn: https://www.linkedin.com/in/jimfielding/Website: https://www.hijimfielding.com/