Corie Sheppard Podcast

Episodes

• Judaline Cassidy: From Diego Martin to New York's Plumbing Union 01.06.2026 1h 33m

  Send us Fan Mail Judaline 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,...
• Wendy Fitzwilliam on Fame, Miss Universe, Motherhood & Why Trini's “Mash Up” Our Own 25.05.2026 1h 44m

  Send us Fan Mail Wendy 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 Mi...
• From Project Runway to Scaling a Luxury Brand from the Caribbean: Anya Ayoung-Chee’s Next Chapter 18.05.2026 1h 31m

  Send us Fan Mail Anya 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 t...
• The Woman Behind Machel Montano: Liz Montano’s Untold Story | CSP 12.05.2026 1h 49m

  Send us Fan Mail Elizabeth “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...
• Valmiki Maharaj on Carnival, Creativity & Building Cultural Experiences | The Corie Sheppard Podcast 11.05.2026 1h 40m

  Send us Fan Mail Valmiki 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 explo...
• Shaka Hislop on Prostate Cancer & Why Men Need to Get Tested 04.05.2026 1h 44m

  Send us Fan Mail Shaka 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 ...
• Coutain | Why Loyalty, Love & Peace Matter More Than Fame | The Corie Sheppard Podcast 27.04.2026 1h 45m

  Send us Fan Mail In 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 i...
• The Truth About the Entertainment Industry No One Tells You | Simon Baptiste 25.04.2026 1h 53m

  Send us Fan Mail Simon 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 t...
• Nailah Blackman: You Don’t Know My Story | Childhood, Legacy, Struggles & Stardom 20.04.2026 1h 40m

  Send us Fan Mail Nailah 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”Alw...
• Nigel Nicholson: The Man Behind Trinidad’s Top Media Talent | The Corie Sheppard Podcast 13.04.2026 1h 34m

  Send us Fan Mail Nigel Nicholson is one of the most influential voices behind media in Trinidad & Tobago — founder of Star Broadcasting and the man responsible for training some of the biggest personalities on radio today. In this episode, we go deep into the fundamentals of broadcasting that most people overlook — from why reading is the “miracle cure” for confidence, to the real skill of connecting with an audience, and why you can’t hide behind the music forever. We also reflect on m...
• Patrick “Mista Vybe” Gordon: From Kiskidee Karavan to Soca History | The Corie Sheppard Podcast 08.04.2026 1h 40m

  Send us Fan Mail Patrick “Mista Vybe” Gordon joins The Corie Sheppard Podcast for a deep dive into one of the most influential yet under-told journeys in Trinidad & Tobago’s music and cultural landscape. From his early days in Kiskidee Karavan and the Party Time era, to being a member of Black Mayl and working closely with $hel $hok, Mista Vybe shares firsthand insight into a generation that reshaped youth culture and music in the Caribbean. We explore: The origins and impact of Kiskidee ...
• Johnny Q: How I Built a Business Overnight With NO Experience 31.03.2026 1h 45m

  Send us Fan Mail Johnny Q is one of Trinidad & Tobago’s most iconic entrepreneurs — but his journey didn’t start in business. It started with DJing, sound systems, and figuring things out in real time. In this episode of The Corie Sheppard Podcast, we sit down with Johnny Q to unpack how he built multiple businesses across events, hardware, auto parts, and entertainment — often with zero experience. He shares the story of opening a hardware business overnight during COVID, the thinking be...
• Raising an Autistic Adult with Joy | Josie of Autistically Speaking | Corie Sheppard Podcast 23.03.2026 1h 8m

  Send us Fan Mail In this powerful and heartfelt conversation, Corie sits down with Josie, the creator of the growing social media platform Autistically Speaking, where she shares the real, unfiltered journey of raising her son Andre, a young adult on the autism spectrum. Originally from Sangre Grande, Josie has spent over two decades living abroad but remains deeply connected to Trinidad & Tobago and its culture. Through her page Autistically Speaking, she documents everyday life with And...
• DJ Bravo: The Mindset Behind the Champion | Corie Sheppard Podcast 16.03.2026 1h 52m

  Send us Fan Mail DJ Bravo: From Santa Cruz to Global Champion | The Corie Sheppard Podcast Dwayne “DJ Bravo” Bravo is one of the most iconic cricketers in the history of West Indies cricket and one of the most successful T20 players of all time. In this episode of The Corie Sheppard Podcast, Bravo reflects on his journey from growing up in Santa Cruz and playing cricket in Tranquillity to becoming a global champion on the biggest stages in world cricket. Bravo shares powerful stories about hi...
• Gervase Warner - Failures Forged a Leader | Corie Sheppard Podcast 13.03.2026 1h 45m

  Send us Fan Mail In this candid and wide-ranging conversation, former Massy Group CEO Gervase Warner reflects on the setbacks, risks, and defining decisions that shaped his journey from a struggling secondary school student to Harvard Business School, McKinsey partner, and one of the Caribbean’s most influential business leaders. Warner shares the lesser-known stories behind his path — academic rejection, early professional failures, and the unexpected gap-year experience that strengthened h...
• War Tunes And The Price Of Peace 04.03.2026 1h 43m

  Send us Fan Mail This episode is a sneak peek into the kind of conversations our Patreon community enjoys every week — deeper discussions, cultural analysis, and unfiltered reasoning about current events through a Caribbean lens. We explore: How global tensions can impact small nations like Trinidad & TobagoThe connection between oil, economics, and everyday life at homeKaiso as social commentary — from Lord Blakey to Bunji GarlinThe lasting message behind “nobody wins a war”The recent Ca...
• Jadel Legere: Tomboy to Pink Power | Soca Hustle & Building Her Empire | The Corie Sheppard Podcast 02.03.2026 1h 38m

  Send us Fan Mail In this powerful and deeply personal episode of The Corie Sheppard Podcast, we sit down with soca artist Jadel Legere for a raw conversation about resilience, reinvention, and building success on her own terms. Jade opens up about growing up in a strict religious household, struggling with identity and self-esteem, and how “pink” became a symbol of reclaiming the childhood she never had. From studying law and battling depression to singing in casinos and eventually touring in...
• Building Your Own Stage: Simi D Trini On Comedy, Courage, And Community 25.02.2026 1h 29m

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• Canaval 2026 Wrapup with Omari Ashby 20.02.2026 1h 28m

  Send us Fan Mail Carnival 2026 sparked big conversations — and Omari Ashby is not holding back. In this powerful and deeply cultural breakdown, Omari Ashby joins us to unpack the moments that defined the season: the Calypso Monarch controversy, the Helon broadcast incident, Road March debates, commentary competence, Panorama pride, and the evolving spirit of Juve and mas. We discuss: • The semifinal and final judging questions • Transparency, censorship, and protecting the art form • Why Terr...
• 3 Canal: Kings of J’Ouvert – Roger Roberts | The Voice & The Harmony 16.02.2026 1h 34m

  Send us Fan Mail In Part III of the 3 Canal: Kings of J’Ouvert trilogy, we sit with Roger Roberts — vocalist, producer, theatre practitioner, and one of the foundational voices behind 3 Canal’s sound and philosophy. From sweeping yards on J’Ouvert morning as a child to commanding Olympic stages with Peter Minshall, Roger reflects on a life shaped by ritual, resistance, and responsibility. This episode traces the journey behind the voice — from choir training and theatre with Derek Walcott to ...