Corie Sheppard Podcast

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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, 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 generation

Judaline's story is a powerful reminder that where you start does not determine where you finish.

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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 Universe
• Celebrity Culture And Media Training
• Donald Trump And The Miss Universe Organization
• Trinidad & Tobago’s Relationship With Success
• Machel Montano, Minshall, Brian Lara And National Identity
• Vulnerability, Motherhood And Her Book Letters to Ailan
• Being Underestimated As A Woman
• Social Media, Fame And Public Perception
• Why Trinidadians Often “Mash Up” Their Own People
• Africa, Ethiopia And Identity
• Fashion, Law And Personal Reinvention

Wendy 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.

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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 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 designers
• The pressure and editing behind reality TV
• Caribbean fashion identity and post-colonial culture
• AI, vibe coding, and the future of creative business
• Entrepreneurship, impact, and building sustainable businesses
• Navigating public scrutiny and personal growth
• Music, Xigon, sound clash culture, and creativity
• Motherhood, reinvention, and purpose

A powerful conversation about resilience, audacity, creativity, and evolving into your next chapter.

#coriesheppardpodcast #AnyaAyoungChee #ProjectRunway #Fashion #AI #CaribbeanCulture #Entrepreneurship

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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 conversation explores:

• Discovering Machel Montano’s talent at age 5
• Raising two highly successful sons in completely different fields
• Marcus Montano’s journey to becoming a senior airline captain and pilot trainer
• The story behind “Too Young To Soca”
• Managing Machel Montano for decades
• Building Ecstatic, Monk Music & the Montano brand
• Parenting, discipline & raising successful children
• The importance of preserving Caribbean culture
• Soca’s evolution and innovation over the decades
• Collaborations with legends like Sparrow, Kitchener, Superblue & David Rudder
• Creating businesses beyond music, including chocolate, hospitality & cultural preservation
• Mental health, criticism, resilience & handling public pressure
• Why Lady Montano believes parenting shapes society

Lady 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.”

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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 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 work

A 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

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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 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 Yorke
• The realities behind World Cup qualification
• Life in the Premier League and the pressure of elite football
• Parenting, identity, and representing Trinidad & Tobago on the world stage

This is a conversation about football — but more importantly, it’s about life.

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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 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 genres
• Respecting the legacy of artists like Sparrow and Kitchener
• Building a unique sound and creative identity
• The discipline required to succeed in music
• Why he’s focused on peace, purpose, and life after music

This 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 influence
• Faith, discipline, and life lessons
• Loss, grief, and turning pain into purpose
• Finding his sound and entering the music industry
• Loyalty, love, and relationship values
• The meaning behind his music
• Building a legacy in soca and Caribbean music
• Life after music and long-term vision

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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 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 Entertainment
• Breaking into Hollywood and the global entertainment industry
• The business of events, film, and artist management
• Why Caribbean talent struggles to scale globally
• The realities behind managing artists and building brands
• The future of soca music and entertainment

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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 land
• Growing up differently and developing discipline early
• Doing competitions while being “against competition”
• Always believing she was destined for greatness
• The moments that shaped her identity as an artist
• The challenges, pressure, and emotional struggles behind the scenes
• What it really takes to build a career in music

This 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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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 my own journey through his program — from struggling with nerves and public speaking to building The Corie Sheppard Podcast — and the lessons that still shape how I approach every interview today.

This conversation is about more than radio. It’s about discipline, preparation, authenticity, and what it really takes to build a voice that people want to listen to.

Topics include:

The real fundamentals of great broadcasting

Why reading improves confidence, vocabulary, and delivery

How to make guests comfortable in interviews

The importance of authenticity and performance

The evolution of radio vs podcasting

What young media talent gets wrong today

Behind-the-scenes of building media careers

Whether you’re into radio, podcasting, content creation, or public speaking — this episode is a masterclass.

👉 Click the link in my bio for the full episode

#coriesheppardpodcast #trinidadpodcast #media #broadcasting #podcasttips #caribbeanculture #communication