Corie Sheppard Podcast

Send us a text [https://www.buzzsprout.com/twilio/text_messages/1725191/open_sms] Cindy-Ann Boisson | Comedy, Honesty & Owning the Trini Accent This week on The Corie Sheppard Podcast, comedian Cindy-Ann Boisson joins me for a hilarious and powerful conversation about the craft of stand-up, surviving the grind, and staying authentic. We talk about her upcoming comedy competition Punched Up, why repeating jokes is part of the art form, and the balance between silence and punchlines. Cindy-Ann shares raw stories—from almost being assaulted in Florida and escaping by diving out of a moving car, to navigating U.S. comedy clubs with her unapologetic Trini accent. We get into what makes Caribbean audiences unique, why she insists on “no intermission” shows, and her Red Woman Tour that’s taking Caribbean stand-up to stages across North America. This episode blends sharp humour with deep honesty about tragedy, time, gender bias in comedy, and the challenge of creating space for Caribbean women on international stages. Click the link in my bio for the full episode. #coriesheppardpodcast #cindyannboisson #standupcomedy #trinicomedy #culture 0:00 [https://www.buzzsprout.com/admin/1725191/dashboard#] Welcome and Introduction to Cindy-Ann 15:25 [https://www.buzzsprout.com/admin/1725191/dashboard#] Punched Up: Creating a Stand-Up Comedy Competition 30:12 [https://www.buzzsprout.com/admin/1725191/dashboard#] The Art of Working Out Jokes and Stage Presence 45:20 [https://www.buzzsprout.com/admin/1725191/dashboard#] Embracing Cultural Identity in Comedy 1:02:35 [https://www.buzzsprout.com/admin/1725191/dashboard#] From Tragedy to Comedy: Personal Storytelling 1:19:18 [https://www.buzzsprout.com/admin/1725191/dashboard#] Comedy Career Beginnings and Development 1:30:56 [https://www.buzzsprout.com/admin/1725191/dashboard#] Gender Barriers in Comedy 1:38:27 [https://www.buzzsprout.com/admin/1725191/dashboard#] Comedy Inspirations and Mount Rushmore

Send us a text [https://www.buzzsprout.com/twilio/text_messages/1725191/open_sms] We sit down with Stacey Sobers — calypsonian, actor, and entrepreneur — for an inspiring conversation on music, resilience, and community. Stacey shares her journey from growing up in Chaguanas to starring in Queen of the Road - Calypso Rose: The Musical, the untold story behind “Let Me Know When You’re Coming,” and the moment that shifted her from soca to calypso. We talk about women in kaiso, mentorship, and the realities of competition at Skinner Park and the Savannah, her 2018 Calypso Queen win, and how she’s building her own sold-out concert brand Crackers & Cheese. This episode is about more than music — it’s about gratitude, perseverance, and creating space for the next generation. Click the link in my bio for the full episode. #coriesheppardpodcast 00:00 – Intro 01:00 – Queen of the Road Calypso Rose musical 03:00 – Butterflies & nerves 04:20 – Exhaustion & rest 06:30 – Cast & band dynamics 07:12 – Learning lyrics 11:02 – “Let Me Know When You’re Coming” 13:20 – From soca to kaiso 20:00 – Party Time & early shows 21:05 – Family & Marlon Asher 23:00 – Competitions begin 24:30 – Voice training at COSTAATT 28:12 – Turning point after tragedy 31:20 – Winning Calypso Queen 36:10 – Challenges for women 43:00 – Skinner Park vs. Savannah 49:20 – Competing until 50 56:08 – “Respect the Tribe” 1:06:25 – Mentors & spiritual support 1:09:16 – Husband as manager 1:14:10 – Crackers & Cheese brand 1:18:14 – Pan at the centre 1:19:56 – Building sustainable shows 1:22:16 – Café Blue as hub 1:25:20 – Advice to young women 1:27:10 – Kaiso call & response 1:28:59 – Closing & Crackers & Cheese plug

Send us a text [https://www.buzzsprout.com/twilio/text_messages/1725191/open_sms] Kit Israel | From Kan Kan to Folklore, Calypso with a K, and the Future of Caribbean Music Kit Israel of AdvoKit Productions joins The Corie Sheppard Podcast for a deep dive into the music, culture, and vision that drive his work. The son of legendary musician and producer Roger Israel, Kit brings both heritage and innovation to the table — combining his degree in Mathematics with his passion for sound to approach music as both science and art. As the producer behind the Kan Kan Riddim, the Folklore Riddim (Hello by Kes, Catching Feelings by Nadia Batson), and hits like Buss Head (Machel & Bunji), Ola (Olatunji), Drink & Party (Ding Dong), Take Me Home (Freetown Collective), and Anxiety (Patrice Roberts), Kit has shaped defining moments in modern soca and calypso. We talk about his creative philosophy, why he chooses to “bust” new artists instead of relying only on the A-list, the business lessons behind owning your masters, and his bold cultural vision for “Calypso with a K.” This episode blends artistry, business, and legacy — a must-listen for anyone invested in the future of Caribbean music.

Send us a text [https://www.buzzsprout.com/twilio/text_messages/1725191/open_sms] Kwesi “Hoppy” Hopkinson has been a driving force in Trinidad & Tobago’s entertainment and media landscape for decades. From his teenage years building Radioactive and Players Inc, to shaping the party culture with iconic events like Soca Picnic, to creating platforms such as Scorch Magazine, Scorch Radio, Island E-Tickets, and now Scorch TV — Hoppy’s story is one of vision, branding, and resilience. In this episode, we talk about: * The early days of sound clashes, dubplates, and rivalries with Jugglers and others * How branding and identity (yellow crates, yellow cars, iconic logos) made Radioactive unforgettable * The entrepreneurial leap from radio personality to media owner * The birth of Scorch and why ownership mattered more than titles * His role in providing space for young DJs, artists, and creatives to grow * The evolution from magazine to radio to TV and the future of Caribbean entertainment

Send us a text [https://www.buzzsprout.com/twilio/text_messages/1725191/open_sms] Marc Jardine: From Fatima Days to the Helm of RBC In this episode, Corie sits down with Marc Jardine, Managing Director and VP of Commercial Banking at RBC Royal Bank Trinidad and Tobago. They reflect on their shared Fatima College roots, school days, and the importance of mentorship and fatherhood. Marc opens up about his unexpected career path—from dreams of ornithology to finance, agriculture, and now banking leadership. The conversation dives into life lessons from Fatima, his experiences studying at Morehouse, the realities of oil and gas and agriculture, and how those shaped his approach to business and leadership. Marc also discusses the changing face of banking in Trinidad and Tobago, the role of SMEs, the challenges of foreign exchange, and the importance of balancing technology with personal connection. Beyond banking, Marc shares candid thoughts on fatherhood, giving back, sustainability, and why beach cleanups, youth mentorship, and personal discipline (yes, even sharpening knives) keep him grounded. This is a conversation about roots, responsibility, and reshaping what leadership can look like in Trinidad and Tobago.