Podcast
Corie Sheppard Podcast
Hosted by Corie Sheppard · EN
The Corie Sheppard Podcast
A trusted space for honest, Caribbean-rooted conversations that connect generations, challenge norms, and celebrate culture through real stories and perspectives.
Hosted by Corie Sheppard-Babb, the podcast explores the lives, journeys, and ideas of the Caribbean’s most compelling voices—artists, entrepreneurs, cultural leaders, changemakers, and everyday people with powerful stories. Each episode goes beyond headlines and hype to uncover the values, history, humour, struggle, and brilliance that shape who we are.
Whether it’s music, business, creativity, identity, advocacy, or community, this podcast holds space for the kind of dialogue that inspires reflection, empowers expression, and preserves our legacy. It’s culture in conversation—unfiltered, intergenerational, and deeply Caribbean.
Listen, subscribe, and be part of the stories that move the region forward.
25episodes
Episodes
Newest firstAll episodes
Jaiga: How I Helped Build Soca's Biggest Stars | Corie Sheppard Podcast
Yesterday01:50:35Tap to summarizeSend us Fan MailJaiga joins us for one of the most revealing conversations ever recorded about the evolution of soca music, talent development, radio, entrepreneurship and mentorship in Trinidad & Tobago.From selling apples in the market as a teenager to becoming one of the most influential figures behind the scenes of Caribbean entertainment, Jaiga shares the stories that shaped his journey.We discuss the creation of Soca Star, the origins of Next Ten, discovering artists like Voice and Ding Dong before they became household names, building Radioactive, working alongside Machel Montano, Destra, Iwer George and Fay-Ann Lyons, and helping launch opportunities for the next generation of talent.Jaiga also opens up about personal growth, therapy, fatherhood, relationships, men's mental health, and why he believes vulnerability is one of a man's greatest strengths.In this episode:• The real story behind Soca Star• How Voice was discovered• Why Ding Dong lived in his mother's house• The creation of Next Ten• Building careers before social media• The hustle of selling apples in the market• Touring the world with Iwer George• How Action became a soca hit• Radioactive, Synergy TV and radio history• Entrepreneurship, sales and business lessons• Fatherhood, therapy and men's mental health• Why only 4 of 106 young men knew their fathers Whether you're a fan of soca, business, entrepreneurship, media, or personal development, this episode offers a rare look at the mindset and experiences behind one of Trinidad & Tobago's most influential cultural figures.#coriesheppardpodcast #Jaiga #Soca #TrinidadAndTobago #CaribbeanCulture
Transcribe →Judaline Cassidy: From Diego Martin to New York's Plumbing Union
1w ago01:33:43Tap to summarizeSend us Fan MailJudaline Cassidy's journey began in Diego Martin, Trinidad, where she grew up facing poverty, abandonment, and countless obstacles. Unable to afford university, she made a decision that would change the course of her life forever—she enrolled in plumbing at the John Donaldson Technical Institute.What followed was an extraordinary journey from Trinidad to New York City, where Judaline became one of the first women in her union, built a successful career in the skilled trades, and founded Tools & Tiaras, a nonprofit that empowers young girls through trade skills, confidence-building, and leadership development.In this episode, Judaline shares powerful stories about growing up without her parents, finding strength through her great-grandmother's guidance, overcoming discrimination as a Black immigrant woman in construction, and why she believes skilled trades can transform lives.We also discuss the importance of trade education, the future of work, the rise of AI, confidence, resilience, and why every young person should learn a skill that can take them anywhere in the world.Topics include:• Growing up in Diego Martin• John Donaldson Technical Institute• Life as a female plumber in New York• Becoming the first woman in her union• Trade school vs university• Building Tools & Tiaras• Confidence, grit and resilience• Women in construction and skilled trades• Entrepreneurship and leadership• Creating opportunities for the next generationJudaline's story is a powerful reminder that where you start does not determine where you finish.
Transcribe →Wendy Fitzwilliam on Fame, Miss Universe, Motherhood & Why Trini's “Mash Up” Our Own
2w ago01:44:18Tap to summarizeSend us Fan MailWendy Fitzwilliam joins The Corie Sheppard Podcast for one of her most open and revealing conversations ever.From winning Miss Universe and navigating global fame, to growing up in Trinidad, studying law, motherhood, media pressure, and the psychology of Caribbean success, Wendy reflects on the experiences that shaped her journey both publicly and privately.The conversation explores:The Reality Behind Miss UniverseCelebrity Culture And Media TrainingDonald Trump And The Miss Universe OrganizationTrinidad & Tobago’s Relationship With SuccessMachel Montano, Minshall, Brian Lara And National IdentityVulnerability, Motherhood And Her Book Letters to AilanBeing Underestimated As A WomanSocial Media, Fame And Public PerceptionWhy Trinidadians Often “Mash Up” Their Own PeopleAfrica, Ethiopia And IdentityFashion, Law And Personal ReinventionWendy also shares untold stories about Rihanna, Ricky Martin, Coolio, Bernie Mac, international media, and the pressure of representing Trinidad & Tobago on the world stage.This is a conversation about confidence, culture, reinvention, and what it really means to carry a country with you.
Transcribe →From Project Runway to Scaling a Luxury Brand from the Caribbean: Anya Ayoung-Chee’s Next Chapter
3w ago01:31:15Tap to summarizeSend us Fan MailAnya Ayoung-Chee joins The Corie Sheppard Podcast for one of her most open and reflective conversations yet. From winning Project Runway with almost no formal sewing experience to navigating public scandal, entrepreneurship, motherhood, AI, Caribbean identity, and rebuilding her fashion brand — this episode explores the mindset behind one of Trinidad & Tobago’s most recognizable creative entrepreneurs.Anya speaks candidly about grief after losing her brother Pilar, the turning points that shaped her life, and how those experiences pushed her toward fashion and entrepreneurship. She also breaks down the realities of the fashion industry, the future of AI in creativity, Caribbean identity in design, and why she believes Caribbean creators can lead globally instead of following trends.The conversation also dives into:Winning Project Runway against experienced designersThe pressure and editing behind reality TVCaribbean fashion identity and post-colonial cultureAI, vibe coding, and the future of creative businessEntrepreneurship, impact, and building sustainable businessesNavigating public scrutiny and personal growthMusic, Xigon, sound clash culture, and creativityMotherhood, reinvention, and purposeA powerful conversation about resilience, audacity, creativity, and evolving into your next chapter.#coriesheppardpodcast #AnyaAyoungChee #ProjectRunway #Fashion #AI #CaribbeanCulture #Entrepreneurship
Transcribe →The Woman Behind Machel Montano: Liz Montano’s Untold Story | CSP
4w ago01:49:30Tap to summarizeSend us Fan MailElizabeth “Lady” Montano joins The Corie Sheppard Podcast for a powerful conversation about motherhood, legacy, discipline, culture, business, and the journey behind one of the Caribbean’s most influential families.Known by many as the mother and longtime manager of Machel Montano, Lady Montano shares the untold stories behind Machel’s early career, the sacrifices made as parents, and the core values that shaped both Machel and Marcus Montano into the men they are today.The conversation explores:Discovering Machel Montano’s talent at age 5Raising two highly successful sons in completely different fieldsMarcus Montano’s journey to becoming a senior airline captain and pilot trainerThe story behind “Too Young To Soca”Managing Machel Montano for decadesBuilding Ecstatic, Monk Music & the Montano brandParenting, discipline & raising successful childrenThe importance of preserving Caribbean cultureSoca’s evolution and innovation over the decadesCollaborations with legends like Sparrow, Kitchener, Superblue & David RudderCreating businesses beyond music, including chocolate, hospitality & cultural preservationMental health, criticism, resilience & handling public pressureWhy Lady Montano believes parenting shapes societyLady Montano also reflects on her own career as an educator and guidance counsellor, her philosophy on leadership, and why legacy must be intentionally built and documented for future generations.“It’s not the teachers. It’s not the church. It’s not the community. It’s the parents.”
Transcribe →Valmiki Maharaj on Carnival, Creativity & Building Cultural Experiences | The Corie Sheppard Podcast
4w ago01:40:48Tap to summarizeSend us Fan MailValmiki Maharaj — Creative Director of The Lost Tribe, Director of TRIBE, and head of Ultimate Events — joins The Corie Sheppard Podcast for a deep conversation on creativity, Carnival, culture, and the business of building unforgettable experiences.From redefining modern mas to coordinating IShowSpeed’s viral Trinidad IRL stream, Valmiki shares the vision, pressure, and innovation behind some of Trinidad & Tobago’s most impactful cultural moments.The conversation explores:• The evolution of TRIBE and The Lost Tribe• Creativity, storytelling, and experiential design• The future of Carnival and preserving authenticity• The business behind large-scale events• Coordinating global productions and viral moments• Youth culture, identity, and Trinidad’s global image• Leadership, resilience, and purpose-driven workA powerful discussion on culture, innovation, and the responsibility of shaping experiences that represent Trinidad & Tobago to the world.#coriesheppardpodcast #ValmikiMaharaj #TRIBE #TheLostTribe #Carnival #TrinidadAndTobago #Podcast #Culture
Transcribe →Shaka Hislop on Prostate Cancer & Why Men Need to Get Tested
May 401:44:04Tap to summarizeSend us Fan MailShaka Hislop joins us for one of the most powerful conversations we’ve ever had.From representing Trinidad & Tobago at the 2006 FIFA World Cup to building a career at the highest levels of English football and broadcasting, Shaka reflects on legacy, pressure, and purpose.But this episode goes deeper.Shaka opens up about his prostate cancer diagnosis, the reality of having no symptoms, and how a routine test may have saved his life. He shares the emotional challenge of telling his children, the mindset he adopted to fight, and why more Caribbean men need to take their health seriously.We also get into:His response to the Trinidad & Tobago FA President’s comments on Dwight YorkeThe realities behind World Cup qualificationLife in the Premier League and the pressure of elite footballParenting, identity, and representing Trinidad & Tobago on the world stageThis is a conversation about football — but more importantly, it’s about life.
Transcribe →Coutain | Why Loyalty, Love & Peace Matter More Than Fame | The Corie Sheppard Podcast
Apr 2701:45:29Tap to summarizeSend us Fan MailIn this episode of The Corie Sheppard Podcast, we sit down with Coutain for a deeply personal and powerful conversation about pain, purpose, love, and the journey behind his music.Coutain shares his story growing up in Sangre Grande, shaped by family, faith, the block, and the cultural influence of calypso, reggae, and Caribbean music. He reflects on the lessons from his grandparents, the importance of discipline, and how early life experiences helped shape his mindset and identity. The conversation takes an emotional turn as he opens up about loss, grief, and the passing of his cousin Shanna, whose belief in him became a turning point in his decision to pursue music seriously. Coutain also breaks down his creative journey—from experimenting with music, finding his sound, and building a team, to working with key collaborators who helped refine his artistry and push him toward a professional career. A major theme throughout the episode is intentional living—in music, relationships, and life. He speaks candidly about loyalty, honesty, and why his personal relationship inspires his music, as well as his commitment to creating songs that go beyond surface-level themes and stand the test of time. The episode also explores:The evolution of soca and bridging genresRespecting the legacy of artists like Sparrow and KitchenerBuilding a unique sound and creative identityThe discipline required to succeed in musicWhy he’s focused on peace, purpose, and life after musicThis is more than a music conversation — it’s a story about growth, self-awareness, and choosing a different path.Coutain is a Trinidadian artist whose music blends soca, dancehall, reggae, and calypso influences, shaped by his upbringing in Sangre Grande and a strong foundation in family, faith, and culture. His work is driven by intention—focusing on storytelling, relationships, and creating music with lasting impact rather than just momentary success.Key Themes / Topics (for platforms like YouTube chapters or Spotify)Growing up in Sangre Grande & family influenceFaith, discipline, and life lessonsLoss, grief, and turning pain into purposeFinding his sound and entering the music industryLoyalty, love, and relationship valuesThe meaning behind his musicBuilding a legacy in soca and Caribbean musicLife after music and long-term vision
Transcribe →The Truth About the Entertainment Industry No One Tells You | Simon Baptiste
Apr 2501:53:37Tap to summarizeSend us Fan MailSimon Baptiste, founder of Question Mark Entertainment, joins The Corie Sheppard Podcast for a deep dive into the business of entertainment, global ambition, and the realities behind building a career in the industry.With over 25 years of experience, Simon shares how he went from Trinidad to working in Los Angeles, producing films, managing artists, and bringing international talent to the Caribbean. He breaks down the power of relationships, spotting opportunity, and the “angles” that helped him open doors most people never even see.The conversation explores the evolution of Trinidad & Tobago’s entertainment industry, the challenges facing soca music globally, and why Caribbean creatives must think beyond local markets. Simon also speaks candidly about artist management, navigating difficult personalities, and the unseen work that goes into building successful careers.This episode is a masterclass in vision, resilience, and thinking global from a small island.In this episode:How Simon Baptiste built Question Mark EntertainmentBreaking into Hollywood and the global entertainment industryThe business of events, film, and artist managementWhy Caribbean talent struggles to scale globallyThe realities behind managing artists and building brandsThe future of soca music and entertainment#coriesheppardpodcast
Transcribe →Nailah Blackman: You Don’t Know My Story | Childhood, Legacy, Struggles & Stardom
Apr 2001:40:09Tap to summarizeSend us Fan MailNailah Blackman joins us on The Corie Sheppard Podcast for one of her most open and revealing conversations yet.Known for her powerful voice and stage presence, Nailah shares the real story behind her journey — from her unique upbringing to becoming one of the Caribbean’s leading artists.In this episode, we explore:Her grandfather’s influence and living off the landGrowing up differently and developing discipline earlyDoing competitions while being “against competition”Always believing she was destined for greatnessThe moments that shaped her identity as an artistThe challenges, pressure, and emotional struggles behind the scenesWhat it really takes to build a career in musicThis is a conversation about legacy, resilience, identity, and purpose — beyond the spotlight.#coriesheppardpodcast #nailahblackman #soca #trinidadandtobago #caribbeanculture #musicindustry #artistjourney #podcast #caribbeanmusic #storytelling
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