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What began as  friends laughing, playing games and being themselves became one of Trinidad and Tobago’s most joyful online movements.

Avril, KP and Shinzy of Cheerful Company join us for a lively and deeply personal conversation about their friendship, their contrasting personalities and the unexpected journey from casual TikTok videos to millions of views.

They share how messages from people struggling with depression inspired the name Cheerful Company, why faith remains at the centre of everything they do, the realities of turning viral content into a business, and how they balance their public personalities with life beyond the camera—including careers in policing.

It’s an episode filled with laughter, honesty, purpose and the unmistakable chemistry that has made Cheerful Company a source of sunshine for so many.

Like, share and subscribe for more meaningful Caribbean-rooted conversations.

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This week’s solo episode starts with an apology to the Mighty Conqueror after last week's search for the “wordiest” calypso — before Corie tells the story of being challenged to attend Lady Lava’s birthday Steam aboard the Harbour Master.

From figuring out what you’re actually supposed to wear to a Steam, to arriving at a boat ride at the correct Trinidadian time, trying to keep up with the younger generation, discovering new music and eventually learning that sometimes your body simply tells you when the party is over — it was an experience.

Then we get into some more serious business.

The new Venezuela–Trinidad and Tobago gas developments could represent a major opportunity for the country — but have we learned anything from our previous energy booms? Corie talks Dutch Disease, government spending, public-sector wages, diversification and why another energy windfall shouldn't simply mean going back to business as usual.

We also get into the new army-police posts, the Independence Day parade changes at the Queen’s Park Savannah, the way political tribalism shapes our reactions to almost everything, the ugliness of social-media comments surrounding tragedy, and Sharon Rowley rediscovering her passion for art in retirement.

Plus music and stories involving Lady Lava, Coutain, Christo, Jordan English, Voice and more.

It’s Steam Night Stories, economics, politics, music, ageing and Trinidad & Tobago being Trinidad & Tobago.

Tell me in the comments: what age do you officially become too old for Steam? 😂

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Born without arms, Veera Bhajan learned from childhood how quickly the world can define someone by what it believes they lack. But behind her remarkable academic achievements and successful legal career was a much deeper struggle involving survival, shame, depression and the pressure to continually prove her worth.

In this deeply personal conversation, Veera explains how achievement became connected to acceptance—and why she eventually realised that much of her life had become performative.

She takes us inside her childhood in Trinidad and Tobago, being rejected from preschool, learning to write and complete everyday tasks with her feet, excelling academically and becoming nationally recognised after placing among the country’s top students.

Veera also discusses the emotional cost of living in survival mode, the public dispute surrounding her appointment to the Equal Opportunity Tribunal and how that painful experience reopened wounds of rejection that stretched back to childhood.

Today, Veera is an attorney, trauma coach, yoga instructor and motivational speaker. Through therapy, meditation and yoga, she has learned to separate her identity from her achievements, disability and past experiences—and reconnect with the person beneath them all.

This conversation explores disability, childhood trauma, depression, healing, hustle culture, education, vulnerability, identity and what it truly means to live an authentic life.

If this conversation resonates with you, like the episode, share it with someone who needs it and subscribe to The Corie Sheppard Podcast.

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Apparently, Trinidad and Tobago has been having some trouble with words lately — so this week, we're putting our vocabulary to the test.

After somehow producing a 30,788-word conversation with KES, I go searching for some of the wordiest and best-written calypsos of all time, with classics from Relator, Mighty Spoiler, Lord Blakie, David Rudder, The Mighty Sparrow and more providing the soundtrack to the conversation.

But as always, the music leads us into some bigger discussions.

We revisit the debate surrounding the new police and army posts at Eddie Hart, and why supporting increased security shouldn't mean we stop asking questions about process and accountability.

I also respond to some of the feedback from last week's discussion about Emancipation and share my experience at Attillah Springer's Roots & Rights Emancipation Concert — an experience that made me think differently about the connection between Emancipation, the Canboulay Riots, culture, business and the enormous tourism potential of what we already have in Trinidad and Tobago.

Then there's Benjai.

His controversial social media post about Indians, soca and Emancipation — and his subsequent apology — leads into a wider conversation about race, division and why I refuse to believe that what we see online represents how most Trinidadians actually feel about one another.

We also get into the Caroni Bird Sanctuary, eco-tourism, the return of the Independence Day parade, the Queen's Park Savannah and why Trinidad and Tobago may have one renewable resource we'll never run out of:

Vibes.

And through it all, we celebrate the extraordinary ability of our calypsonians to use words — to tell stories, make us laugh, challenge society and somehow fit more lyrics into four minutes than I thought humanly possible.

This is not about having all the answers. It's about starting the conversation.

Tell me where you agree, where you disagree, and most importantly:

What is the wordiest calypso of all time?

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What takes someone from the Canadian military to Afghanistan, Sudan, Bangladesh, Egypt, Jordan and Algeria — and eventually to Carnival, J’ouvert, panyards and life in Trinidad and Tobago?

In this episode of The Corie Sheppard Podcast, we sit down with Michael Callan, High Commissioner of Canada to Trinidad and Tobago, for a wide-ranging conversation about diplomacy, conflict, culture and the experiences that have shaped his life.

Michael takes us inside his time in Kandahar, Afghanistan, where he worked as a civilian alongside the military in an increasingly dangerous environment. He reflects on the pressure of making decisions with real consequences, the conversations he had with his family about the possibility that he might not return home, and why one of the most difficult periods of his life was also one of his most rewarding.

We also trace his journey through international development and diplomacy — from Bangladesh and Sudan to Egypt, Jordan and his time as Canada’s Ambassador to Algeria — and explore what years spent around conflict taught him about people, institutions, leadership and the things human beings have in common.

Then the conversation comes home to Trinidad and Tobago.

Michael talks about discovering the country beyond the diplomatic bubble: exploring Tobago, visiting panyards, experiencing Canboulay, playing mas with The Lost Tribe, taking part in J’ouvert and even learning to make callaloo.

We also explore the centuries-old connections between Canada and Trinidad and Tobago, from trade and migration to Carnival, Caribana, the Caribbean diaspora and even the extraordinary journey of leatherback turtles between our two countries.

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What if the biggest thing dividing Trinidad and Tobago isn't race, politics or religion—but the way we choose to treat each other?

This week, I reflect on the response to our Dominic Hadeed interview before exploring the conversations that dominated the Emancipation weekend. From the Indian High Commission controversy and the Emancipation Village to politics, identity and national discourse, one question kept coming back:

Why do we so often extend grace to strangers, yet struggle to show that same grace to our own people?

Along the way, we discuss:

• The response to the Dominic Hadeed interview
• Emancipation, identity and national pride
• The Indian High Commission controversy
• The Emancipation Village experience
• Politics, race and public discourse
• Why supporting culture also means supporting business
• What it means to build a country where everyone belongs

These weekly conversations aren't about telling you what to think. They're about slowing down, looking beyond the headlines and making sense of the issues shaping Trinidad and Tobago.

I'd love to hear your thoughts in the comments.

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Fresh off the Roots, Rock, Soca Tour, Kes joins The Corie Sheppard Podcast for one of his most personal and insightful conversations to date.
Known for timeless hits and electrifying performances, Kes reflects on the journey behind the music, the responsibility of representing the Caribbean on the global stage, and why introducing new audiences to Soca has become his mission.

In this episode, we discuss:

The vision behind the Roots, Rock, Soca Tour
Taking Soca to audiences around the world
The stories behind some of his biggest songs
Family, fatherhood and staying grounded
Creativity, longevity and purpose
The future of Caribbean music
Whether you've followed Kes from the beginning or you're just discovering his music, this conversation offers a rare look at the person behind one of the Caribbean's most influential artists.

This episode is brought to you in partnership with the new Lucozade Sport Ice Kick by Jude Bellingham. With refreshing lemon and lime flavour, plus carbohydrates and electrolytes to help hydrate, fuel and restore during and after exercise, it's the perfect companion for active lifestyles. Available for a limited time only. Thanks to Lucozade Sport for partnering with us on this episode.

🎧 Listen on Spotify, Apple Podcasts and wherever you get your podcasts.

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From building one of Trinidad and Tobago's most recognised brands to developing a philosophy centred on solving problems, Dominic Hadeed shares the ideas that have shaped his approach to business, leadership and life.

In this conversation, Dominic explains why success is often the absence of failure, why every entrepreneur must define their end game before chasing it, and how learning to embrace honest feedback can transform both business and personal growth.

We discuss Blue Waters, entrepreneurship, leadership, company culture, problem solving, Trinidad and Tobago's business environment, the future of Caribbean enterprise and the lessons Dominic believes every leader should learn.

Editor's Note: This interview was recorded before the recent events involving Dominic Hadeed and members of his family. Those events are not discussed during this interview. At the time of publication, Mr Hadeed and his wife had been released after their Preventive Detention Orders were revoked. This conversation is presented as it was originally recorded.

If you enjoyed this episode, subscribe for more conversations with the Caribbean's most influential leaders, entrepreneurs, creatives and changemakers.

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Vaughnette Bigford is one of Trinidad & Tobago's most celebrated performers, but behind the sold-out concerts and standing ovations was a deeply personal journey through depression, perimenopause, identity and rebuilding her life.

In this powerful conversation, Vaughnette opens up about the hardest year of her life, why she believes more women need to speak openly about menopause, the devastating closure of Petrotrin, building her own brand without waiting for opportunities, and how studying at Berklee changed the way she viewed Caribbean music forever.

She also reflects on entrepreneurship, confidence, parenting, community, jazz, calypso and why finding your authentic voice matters more than trying to become someone else.

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Cro Cro is one of Trinidad & Tobago's most influential calypsonians, and in this episode of The Corie Sheppard Podcast he reflects on a career built on fearless social commentary, political criticism and some of the most memorable songs in calypso history.

From Common Entrance and Apology to Nobody Ain't Gonna Know , Breastfed and Pass the Ball, Cro Cro explains the stories behind his biggest hits, why he wrote them and the public reaction they created.

He also shares his views on the current state of calypso, why he believes social commentary is disappearing from the competition, why he stopped competing in the Calypso Monarch, and why he believes calypso was born to challenge power rather than avoid controversy. The conversation explores judging, TUCO, political commentary, censorship, freedom of expression and whether today's calypsonians are still willing to speak truth to authority.

Beyond the controversy, Cro Cro opens up about his songwriting process, learning from legends like Sparrow and Shadow, his early years in the tents, the discipline behind his stage performances, and what it takes to write songs that stand the test of time. He also discusses Machel Montano, Kurt Allen, Orlando Octave, the People's Choice award, and why he has never compromised his writing to satisfy judges or public opinion.

Whether you've followed Cro Cro throughout his career or you're discovering his music for the first time, this conversation offers a rare insight into one of calypso's greatest writers and performers, and the philosophy that has defined his career.

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